Organic compound and organic light-emitting device

Abstract

To provide an organic compound that realizes good light emission properties and durability properties when used in an organic light-emitting element.SOLUTION: An organic compound is represented by the general formula [1]. In the formula, R1 to R21 are each independently selected from among a hydrogen atom, a deuterium atom, a halogen atom and a substituent; and R9 and R19 are optionally bonded together, where, if R9 and R19 are bonded together, the bonding is selected from among direct bonding, bonding via an oxygen atom or sulfur atom, and bonding via CR20R21.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] An organic light-emitting device (hereinafter sometimes referred to as an "organic electroluminescence device" or "organic EL device") is an electronic device having a 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 device emits light. Recent advances in organic light-emitting devices have been remarkable, including low driving voltage, diverse emission wavelengths, high-speed response, and the possibility of thinning and reducing the weight of light-emitting devices. Incidentally, there has been active research to date into compounds suitable for organic light-emitting devices. This is because, in order to provide high-performance organic light-emitting devices, it is important to create compounds that have excellent light-emitting and life characteristics. As an example of a compound having a xanthone moiety that has been created so far, Patent Document 1 describes the following compound 1-A. Furthermore, Patent Document 2 describes the following compound 1-B.

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

[0004] [Patent Document 1] International Publication No. 2006 / 114966 Pamphlet [Patent Document 2] International Publication No. 2015 / 002213 Brochure Summary of the Invention [Problem to be solved by the invention]

[0005] The inventors have investigated and found that, as will be described later, the above compounds 1-A and 1-B have small T1 energy (triplet energy), and therefore, when used in an organic light-emitting element, the luminous efficiency of the element is low and there is room for improvement in durability characteristics. An object of the present invention is to provide an organic compound that, when used in an organic light-emitting device, exhibits excellent light-emitting properties and durability, and to provide an organic light-emitting device using the organic compound. [Means for solving the problem]

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

[0007] [ka] In the above formula [1], R1 to R 19 are each independently selected from a hydrogen atom, a deuterium 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 heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, and a cyano group; R and R 19 may be bonded. R9 and R 19 When bonded, it can be a direct bond, a bond via an oxygen atom, a bond via a sulfur atom, or CR 20 R 21 The bond is selected from bonds via R 20 , R 21 are each independently selected from the R1 to R 19 is the same as X1 and X2 each independently represent an oxygen atom, a sulfur atom, or a CR 20 R 21 , or a single bond and X 1 and X 2 If one of the bonds is a single bond, the other is an oxygen atom, a sulfur atom, or a CR 20 C 21 Either: Ar represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group. n is 1 or 2 Represents the integer vinegar. m represents an integer of 1 or more and 4 or less. When the alkyl group, alkoxy group, amino group, aryloxy group, heteroaryloxy group, silyl group, aromatic hydrocarbon group, or heterocyclic group has a substituent, the substituent may be any of fluorine, chlorine, bromine, iodine, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, tertiary butyl group, methoxy group, ethoxy group, propoxy group, dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, ditolylamino group, phenoxy group, phenyl group, biphenyl group, pyridyl group, pyrrolyl group, cyano group, and deuterium atom. [Effects of the Invention]

[0008] According to the present invention, an organic compound having a high T1 energy and excellent stability as a compound can be provided, and by using such an organic compound, an organic light-emitting device having excellent light-emitting properties and life characteristics can be provided. [Brief explanation of the drawings]

[0009] [Figure 1] FIG. 2 is a diagram comparing the planarity of the electron-donating site of the organic compound of the present invention with that of a comparative compound. [Figure 2] FIG. 1 is a diagram comparing the HOMO and LUMO distributions of an organic compound of the present invention and a comparative compound. [Figure 3] FIG. 1 is a diagram comparing the planarity of the electron-donating moiety of the organic compounds of the present invention. [Figure 4] 1A is a schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the present invention, and FIG. 1B is a schematic cross-sectional view showing an example of a display device using an organic light-emitting element according to one embodiment of the present invention. [Figure 5] 1A is a schematic diagram of an image forming apparatus according to one embodiment of the present invention, and FIGS. 1B and 1C are schematic diagrams showing a configuration in which a plurality of light-emitting units of an exposure light source are arranged on a long substrate. [Figure 6] 1 is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention. [Figure 7] 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 8] 1A is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention, and FIG. 1B is a schematic diagram illustrating an example of a foldable display device. [Figure 9] 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 10] 1A and 1B are schematic diagrams illustrating an example of a wearable device according to an embodiment of the present invention, each of which has an imaging device; DETAILED DESCRIPTION OF THE INVENTION

[0010] The organic compound of the present invention is an organic compound represented by the following general formula [1].

[0011] [ka]

[0012] In the above formula [1], R1 to R 19 are each independently selected from a hydrogen atom, a deuterium 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 heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, and a cyano group; R and R 19 may be bonded. R9 and R 19 When bonded, it can be a direct bond, a bond via an oxygen atom, a bond via a sulfur atom, or CR 20 R 21 The bond is selected from bonds via R 20 , R 21 are each independently selected from the R1 to R 19 is the same as X1 and X2 each independently represent an oxygen atom, a sulfur atom, or a CR 20 R 21 or a single bond. Ar represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group. n represents an integer of 0 to 2, and when n is 0, any one of R1 to R8 and R9 to R 19 Either of these bonds directly. m represents an integer of 1 or more and 4 or less.

[0013] R1 to R 21 The halogen atom, alkyl group, alkoxy group, amino group, aryloxy group, heteroaryloxy group, silyl group, aromatic hydrocarbon group, and heterocyclic group represented by the following formula will be specifically described. Examples of halogen atoms include, but are not limited to, fluorine, chlorine, bromine, and iodine.

[0014] Examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a secondary butyl group, an octyl group, a cyclohexyl group, a 1-adamantyl group, and a 2-adamantyl group.

[0015] Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy, 2-ethyl-octyloxy, and benzyloxy groups.

[0016] Examples of the amino group include, but are not limited to, an N-methylamino group, an N-ethylamino group, an N,N-dimethylamino group, an N,N-diethylamino group, an N-methyl-N-ethylamino group, an N-benzylamino group, an N-methyl-N-benzylamino group, an N,N-dibenzylamino group, an anilino group, an N,N-diphenylamino group, an N,N-dinaphthylamino group, an N,N-difluorenylamino group, an N-phenyl-N-tolylamino group, an N,N-ditolylamino group, an N-methyl-N-phenylamino group, an N,N-dianisolylamino group, an N-mesityl-N-phenylamino group, an N,N-dimesitylamino group, an N-phenyl-N-(4-tert-butylphenyl)amino group, an N-phenyl-N-(4-trifluoromethylphenyl)amino group, and an N-piperidyl group.

[0017] Examples of the aryloxy group and heteroaryloxy group include, but are not limited to, a phenoxy group and a thienyloxy group.

[0018] Examples of the silyl group include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0019] Examples of aromatic hydrocarbon groups include, but are not limited to, phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, fluoranthenyl, and triphenylenyl groups.

[0020] Examples of heterocyclic groups include, but are not limited to, pyridyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, carbazolyl, acridinyl, phenanthrolyl, dibenzofuranyl, and dibenzothiophenyl groups.

[0021] Examples of the substituent that the alkyl group, alkoxy group, amino group, aryloxy group, heteroaryloxy group, silyl group, aromatic hydrocarbon group, and heterocyclic group may further have include halogen atoms such as fluorine, chlorine, bromine, and iodine; alkyl groups such as methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, and tertiary butyl group; alkoxy groups such as methoxy group, ethoxy group, and propoxy group; amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, and ditolylamino group; aryloxy groups such as a phenoxy group, aromatic hydrocarbon groups such as a phenyl group and a biphenyl group, Examples include, but are not limited to, heterocyclic groups such as pyridyl and pyrrolyl groups, cyano groups, and deuterium atoms.

[0022] Next, a method for synthesizing the organic compound according to this embodiment will be described. The organic compound according to this embodiment can be synthesized, for example, according to the reaction scheme shown below.

[0023] [ka]

[0024] Various compounds can be obtained by appropriately changing the compounds shown in (a) to (h) above. This embodiment is not limited to the above synthesis scheme, and various synthesis schemes and reagents can be used. The synthesis method will be described in detail in the Examples.

[0025] Next, the properties of the organic compound according to this embodiment will be described. The organic compound according to this embodiment has the following characteristics (1) to (4), and therefore has a large T1 energy (triplet energy) and is a compound with excellent stability as a compound. Furthermore, by using this organic compound, it is possible to provide an organic light-emitting device with excellent luminous efficiency and device durability. (1) The electron-donating moiety is a triphenylamine-bridged structure, and is not bonded to the xanthone skeleton, which is the electron-withdrawing moiety, via a nitrogen atom, resulting in a high T1 energy. (2) The electron-donating site has a structure in which the phenyl groups of triphenylamine are crosslinked at two or more points, resulting in high bond stability. (3) The electron donating site has a structure in which triphenylamine is crosslinked, and therefore the planarity of the electron donating site is low. (4) The electron-donating and electron-withdrawing moieties have separate HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital), making them useful as bipolar hosts.

[0026] The above features (1) to (4) will be explained below. (1) The electron-donating moiety is a triphenylamine-bridged structure, and is not bonded to the xanthone skeleton, which is the electron-withdrawing moiety, via a nitrogen atom, resulting in a high T1 energy. In inventing the organic compound of this embodiment, the inventors focused on the structure of the electron-donating moiety and the electron-withdrawing moiety. Specifically, the organic compound of this embodiment has a triphenylamine-bridged structure as the electron-donating moiety and a xanthone skeleton as the electron-withdrawing moiety. This results in a high T1 (triplet energy). This is because the presence of an electron-donating moiety and an electron-withdrawing moiety in the molecule leads to an excited state associated with a CT (charge transfer) transition, resulting in a high T1 energy.

[0027] Table 1 shows a comparison of the T1 (triplet energy) of Exemplary Compound A4, an organic compound of the present embodiment, with Comparative Compounds 1 and 2. Comparative Compound 1 is Compound 1-A described in Patent Document 1. Comparative Compound 2 has a structure similar to Compound 1-B described in Patent Document 2. Compound 1-B has phenoxazine bonded to the 3- and 6-positions of xanthone, whereas Comparative Compound 2 has a structure in which phenoxazine is bonded to the 2- and 7-positions of xanthone. Compound 1-B and Comparative Compound 2 are considered to have equivalent T1 energies. The T1 energy was measured using a Hitachi "F-4500" by photoluminescence (PL) measurement of a diluted toluene container at 77 K and an excitation wavelength of 350 nm, and calculated from the peak wavelength on the short wavelength side of the emission spectrum.

[0028] [Table 1]

[0029] As shown in Table 1, the T1 of Example Compound A4 was 457 nm. On the other hand, the T1 of Comparative Compound 1 was 475 nm, and the T1 of Comparative Compound 2 was 511 nm. From the above, it can be seen that Example Compound A4 has a higher T1 energy. This is considered as follows.

[0030] In the case of comparative compounds 1 and 2, the electron donating moiety is bonded to the xanthone skeleton via an N atom, which is thought to enhance the CT property between the electron donating moiety and the electron withdrawing moiety and result in a low T1 energy. In contrast, the organic compound of the present embodiment represented by general formula [1] has a structure in which the electron donating moiety is bonded to the xanthone skeleton via at least one phenyl group, which allows the CT property between the electron donating moiety and the electron withdrawing moiety to be maintained at an appropriate level, resulting in a high T1 energy.

[0031] Here, the effect of a high T1 energy on an organic light-emitting device will be described. A phosphorescent light-emitting device is an organic light-emitting device that uses T1 energy for light emission. The host material for the emitting layer of an organic light-emitting device and the peripheral layers in contact with the emitting layer must have a T1 energy greater than that of the phosphorescent material that emits phosphorescence. Therefore, when the organic compound of this embodiment is used in a phosphorescent light-emitting device, particularly when used as a host material for the emitting layer, the organic compound of this embodiment has a high T1 energy, and therefore can provide highly efficient device characteristics.

[0032] In addition, in the delayed fluorescence element, the S1 energy is used for light emission by reverse intersystem crossing, and in order to induce reverse intersystem crossing, the T1 energy is sufficiently high, and the difference between the S1 energy and the T1 energy must be small. Therefore, when the organic compound of this embodiment is used in a delayed fluorescence element, particularly when used as the light-emitting material of the light-emitting layer, the organic compound of this embodiment has a high T1 energy, and therefore can be expected to exhibit highly efficient element characteristics.

[0033] (2) The electron donating site has a structure in which triphenylamine is crosslinked, resulting in high bond stability. In developing the organic compound of this embodiment, the inventors focused on the bond stability of the electron donating moiety. Specifically, the organic compound of this embodiment has a crosslinked structure between the phenyl groups of the triphenylamine. This provides high bond stability as an organic compound.

[0034] Table 2 shows the results of comparing the bond distances of Example Compound B4, an organic compound of this embodiment, with Comparative Compounds 1 and 2. It can be said that the shorter the bond distance, the higher the bond stability. In Table 2, the bond indicated by a is the bond with the longest bond distance in the molecule.

[0035] [Table 2]

[0036] As shown in Table 2, it can be seen that the C-N bond between the electron-donating moiety and the electron-withdrawing moiety has the longest bond distance in Comparative Compounds 1 and 2. In contrast, it can be seen that the C-N bond at the electron-donating moiety in the organic compound of this embodiment has a short bond distance because triphenylamine has a crosslinked structure. Therefore, it can be said that the bond stability is high.

[0037] In addition, the presence of a crosslinked structure has the following effect. In the cases of Comparative Compounds 1 and 2, when bond cleavage occurs in a C-N bond with low bond stability, disproportionation causes a transition to a different structure, i.e., decomposition progresses. On the other hand, in the case of the organic compound of this embodiment, even when bond cleavage occurs in a C-N bond, the presence of a crosslinked structure increases the probability of recombination, making it possible to suppress decomposition.

[0038] [ka]

[0039] [ka]

[0040] From the above, it can be seen that the organic compound of this embodiment has high stability of the bonds that form the molecular structure. Due to the high bond stability, molecular decomposition is unlikely to occur, and therefore, an organic light-emitting element using the organic compound of this embodiment has excellent durability.

[0041] The bond distances were evaluated using molecular orbital calculations. The molecular orbital calculation method used was the density functional theory (DFT), which is currently widely used. The functional was B3LYP, and the basis set was 6-31G. *It is also a smooth-flowing waveguide called Gaussian09(Gaussian09, RevisionC.01,MJFrisch,GWTrucks,HBSchlegel,GEScuse ria, MARobb,JRCheeseman,G.Scalmani,V.Barone,B.Mennucci,GAPetersson,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.) In addition, a comprehensive overview of the structural integrity of the system is presented.

[0042] (3) The electron donating site has a structure in which triphenylamine is crosslinked, and therefore the planarity of the electron donating site is low. In inventing the organic compound of this embodiment, the inventors focused on the planarity of the electron-donating moiety. Specifically, in the organic compound of this embodiment, the xanthone skeleton, which is the electron-withdrawing moiety, has a highly planar structure, so it is preferable that the electron-donating moiety have low planarity. This is because high planarity in both the electron-donating moiety and the electron-withdrawing moiety increases crystallinity. In other words, this promotes molecular packing, in which molecules overlap each other, which deteriorates film properties, and is therefore undesirable. Since the organic compound of this embodiment has low planarity in the electron-donating moiety, molecular packing can be suppressed, making it less likely to crystallize and more amorphous.

[0043] Here, high amorphousness, i.e., good film properties, are preferable when used in organic light-emitting devices. This is because high amorphousness makes it difficult for grain boundaries, trap levels, and quenchers to be generated due to microcrystallization even during device operation, thereby maintaining good carrier transport properties and highly efficient light-emitting characteristics. As a result, it is possible to provide organic light-emitting devices with excellent durability and efficiency.

[0044] Here, the planarity of the electron donating moiety (the dotted circle in the table) of Example Compound B1, which is an organic compound of this embodiment, and Comparative Compound 1 is compared, and the results are shown in Figure 1. As shown in Figure 1, the electron donating moiety of Comparative Compound 1 has a carbazole skeleton, and therefore has high planarity. In contrast, in the case of Example Compound B1, the electron donating moiety is triphenylamine having a crosslinked structure, and therefore it can be seen that the planarity is reduced due to steric repulsion of the phenyl group. As described above, the organic compound of this embodiment has excellent filmability, and therefore can provide an organic light-emitting device with excellent durability and efficiency.

[0045] (4) The electron-donating and electron-withdrawing moieties have separate HOMO and LUMO regions, making them useful as bipolar hosts. In developing the organic compound of this embodiment, the inventors focused on the charge separation between the HOMO and LUMO. Specifically, in the organic compound of this embodiment, the HOMO is localized in the bridged triphenylamine, which is the electron-donating moiety, and the LUMO is localized in the xanthone skeleton, which is the electron-withdrawing moiety. This makes the compound useful as a bipolar host. This is because triphenylamine is generally electron-donating and therefore stable against oxidation but unstable against reduction. In other words, it is unstable with respect to electrons. In other words, it is preferable that the LUMO molecular orbital does not extend to the triphenylamine. On the other hand, the xanthone skeleton is electron-withdrawing and therefore stable against reduction but unstable against oxidation. In other words, it is unstable with respect to holes. In other words, it is preferable that the HOMO molecular orbital does not extend to the xanthone skeleton. In short, it is preferable that the HOMO is localized in the electron-donating moiety and the LUMO is localized in the electron-withdrawing moiety.

[0046] Here, the results of comparing the HOMO and LUMO distributions of the organic compound of this embodiment and the comparative compound are shown in Figure 2. In Figure 2, the organic compound of this embodiment has a HOMO localized at the bridged triphenylamine, which is the electron-donating moiety, and a LUMO localized at the xanthone, which is the electron-withdrawing moiety. Therefore, it can be said to be a functionally separated bipolar host. On the other hand, in the case of comparative compound 1, the HOMO is distributed all the way to the xanthone moiety, making it unsuitable as a bipolar host.

[0047] The evaluation of the light-emitting characteristics and life characteristics of the organic compound of this embodiment, listed as the characteristics (1) to (4), will be described in more detail in the examples to be described later.

[0048] Furthermore, the organic compound of this embodiment can be particularly suitably used in an organic light-emitting device when it further has the following characteristics. (5) In the general formula [1], at least one of X1 and X2 is CR 20 R 21 It is a compound in which (6) In the general formula [1], at least one of X1 and X2 is a compound containing an oxygen atom or a sulfur atom. (7) In the general formula [1], m=1, and the triphenylamine skeleton is bonded to any one of R2, R3, R6, and R7 of the xanthone skeleton. These features will be explained below.

[0049] (5) At least one of X1 and X2 is CR 20 R 21 It is a compound in which In the organic compound of this embodiment, at least one of X1 and X2 is CR 20 R 21 is preferable. This is because the structure has a substituent in the direction perpendicular to the in-plane direction of the electron donating moiety, which can particularly prevent the electron donating moieties from overlapping with each other. Here, in FIG. 3, the planarity of the electron donating moiety of the organic compound of this embodiment is compared. In FIG. 3, the planarity of the electron donating moiety is compared by the dihedral angle of benzene shown by a and b. Example compound A4 has a dihedral angle of 41°, while the dihedral angle of example compound B1 is 33°. From the above, it can be seen that example compound A4 has lower planarity of the crosslinked triphenylamine. In addition, CR 20 R 21 (In the case of example compound A4, R 20 , R 21 The electron donating moiety has a substituent group perpendicular to the in-plane direction of the electron donating moiety. As a result, planar molecular packing can be more effectively suppressed.

[0050] (6) At least one of X1 and X2 is a compound containing an oxygen atom or a sulfur atom. The organic compound of this embodiment preferably contains an oxygen atom or a sulfur atom at the crosslinking site of triphenylamine. The abundant unshared electron pairs possessed by these atoms can enhance charge transport properties, making this compound particularly easy to adjust the carrier balance. In other words, this compound is useful as a bipolar host, and is therefore particularly suitable as a host material for the light-emitting layer.

[0051] (7) In the general formula [1], m=1, and the triphenylamine skeleton is bonded to any one of R2, R3, R6, and R7 of the xanthone skeleton. In the organic compound of this embodiment, in the general formula [1], m=1 is preferably satisfied, because when m=1, the compound becomes useful as a bipolar host.

[0052] Here, the HOMO and LUMO distributions of exemplary compounds A4 and A19 are compared as shown in Table 3. Example compound A4 has m = 1, while example compound A19 has m = 2. In the case of example compound A19, the LUMO is localized in the xanthone skeleton, making it difficult to transfer electrons to adjacent molecules via the LUMO. This is because the LUMO is localized in the xanthone skeleton, and the electron-donating moieties on both ends cover this LUMO, inhibiting carrier transfer between LUMOs. As a result, the electron transport performance is slightly reduced, leaving room for improvement as a bipolar host.

[0053] On the other hand, Example Compound A4 has only one electron donating site and does not cover the LUMO localized in the xanthone skeleton, so it does not inhibit electron transfer between LUMOs, maintaining good electron transport properties and making it useful as a bipolar host.

[0054] [Table 3]

[0055] Furthermore, it is preferable that the triphenylamine skeleton is bonded to any of R2, R3, R6, and R7 of the xanthone skeleton. This is because bonding at these substitution positions results in a shorter bond distance. A shorter bond distance means higher bond stability, which is preferable because the compound is stable.

[0056] Specific examples of the organic compound of this embodiment are shown below, but this embodiment is not limited to these.

[0057] [ka]

[0058] [ka]

[0059] [ka]

[0060] [ka]

[0061] [ka]

[0062] [ka]

[0063] Among the above exemplary compounds, the exemplary compounds belonging to group A are those in which at least one of X1 and X2 is CR 20 R 21 These compounds are compounds in which CR 20 R 21 Since the compound has a substituent at the position perpendicular to the in-plane direction of the electron donating moiety, it is possible to particularly prevent the electron donating moieties from overlapping with each other. Therefore, the compound has particularly excellent amorphous properties.

[0064] Among the above exemplary compounds, the exemplary compounds belonging to Group B are compounds in which at least one of X1 and X2 contains an oxygen atom or a sulfur atom. These compounds contain an oxygen atom or a sulfur atom in the electron donating site, and therefore the abundant unshared electron pairs possessed by these atoms can enhance charge transport properties, making them particularly easy to adjust the carrier balance.

[0065] Furthermore, the compound of this embodiment is preferably used in the light-emitting layer of the organic light-emitting device under the following conditions. (6) The compound of this embodiment is used as a host material in an amount of 50% by mass or more and 99% by mass or less in the light-emitting layer. (7) The compound of this embodiment is used as an assist material in an amount of 10% by mass or more and 49% by mass or less in the light-emitting layer. (8) The light-emitting material mixed with the compound of this embodiment in the light-emitting layer is a phosphorescent material having a fused ring consisting of at least three rings in the ligand.

[0066] The above conditions will be explained below. (6) The compound of this embodiment is used as a host material in an amount of 50% by mass or more and 99% by mass or less in the light-emitting layer. The organic compound of this embodiment is highly amorphous and therefore suitable as a host material for the light-emitting layer, and is preferably used in an amount of 50% by mass or more. Even when used in an amount of 99% by mass, the compound is difficult to crystallize, and therefore exhibits excellent properties.

[0067] This is due to the structural characteristics of the organic compound of this embodiment. The organic compound of this embodiment is characterized by a structure in which triphenylamine is crosslinked so that the planarity of the electron-donating moiety is reduced. Therefore, the compound is less likely to aggregate, and even when the organic light-emitting device is driven, crystal grain boundaries associated with molecular aggregation are less likely to occur, making it possible to provide a light-emitting device with excellent characteristics. Furthermore, since the compound is composed of an electron-donating moiety and an electron-withdrawing moiety, it has bipolar properties. Therefore, it is useful as a bipolar host.

[0068] (7) The compound of this embodiment is used as an assist material in an amount of 10% by mass or more and 49% by mass or less in the light-emitting layer. When the organic compound of this embodiment is used in the light-emitting layer, it may be used as an assist material from the viewpoint of improving the film properties of the light-emitting layer. When used as an assist material, it can be used in an amount of 10% by mass or more and 49% by mass or less. Furthermore, by taking advantage of the bipolarity that is a characteristic of the organic compound of this embodiment, it can also be used as a hole-trapping assist or an electron-trapping assist.

[0069] As described in (6) above, when the organic compound of this embodiment is used as a host material in the light-emitting layer, it is preferably used in an amount of 50% by mass to 99% by mass. Therefore, it can be said that the organic compound of this embodiment is preferably used as a host material or an assist material in the light-emitting layer in an amount of 10% by mass to 99% by mass.

[0070] (8) The light-emitting material mixed with the compound of this embodiment in the light-emitting layer is a phosphorescent material having a fused ring consisting of at least three rings in the ligand. The organic compound of this embodiment is a compound having a triphenylamine-crosslinked structure and a xanthone skeleton. Therefore, the phosphorescent material used together with the organic compound of this embodiment as an emitting layer preferably has a structure in which the π-conjugation of the ligand is extended. More specifically, the ligand preferably has a fused ring structure consisting of three or more rings. This is because, like the host material, the highly planar structure allows highly planar portions to approach each other through interaction. More specifically, the planar portions of the host material and the ligands of the organometallic complex are more likely to approach each other. This is expected to shorten the intermolecular distance between the host material and the organometallic complex.

[0071] It is known that triplet energy used in phosphorescent light-emitting devices undergoes energy transfer via the Dexter mechanism. The Dexter mechanism involves energy transfer through molecular contact. That is, by shortening the intermolecular distance between the host material and the guest material, energy transfer from the host material to the guest material is efficient.

[0072] In this embodiment, by using a highly planar organometallic complex having a ligand structure with fused rings consisting of three or more rings, the intermolecular distance of the host material, which is the organic compound of this embodiment, is shortened, and energy transfer from the host to the organometallic complex occurs more efficiently, thereby providing a highly efficient organic light-emitting device.

[0073] Here, the highly planar fused ring structure of the ligand, which is composed of three or more rings, refers to triphenylene, phenanthrene, fluorene, benzofluorene, dibenzofuran, dibenzothiophene, benzoisoquinoline, and naphthoisoquinoline. In other words, by using an organometallic complex having at least one of these structures as a ligand as a light-emitting material, the organic compound of this embodiment can provide a light-emitting device with higher efficiency. More specifically, it is a compound represented by the following general formula [2].

[0074] Ir(L) m (L') n (L”) r [2] In the above formula [2], L, L', and L" each represent a different bidentate ligand.

[0075] m is selected from an integer of 1 or more and 3 or less, and n and r are each independently selected from an integer of 0 or more and 2 or less, provided that m+n+r=3.

[0076] Substructure Ir(L) m are represented by the following general formulas [Ir-1] to [Ir-11].

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[0079] In the above formulas [Ir-1] to [Ir-11], Ar1 and Ar2 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, p and q represent integers of 0 to 4, and X is selected from an oxygen atom, a sulfur atom, a substituted or unsubstituted carbon atom, and a substituted or unsubstituted nitrogen atom.

[0080] The L may further have a deuterium atom, a fluorine atom, a substituted or unsubstituted alkyl group, a deuterium-substituted alkyl group, an alkoxy group, a substituted or unsubstituted silyl group, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0081] Specific examples of organometallic complexes that can be suitably used with the compounds of this embodiment are shown below, but the present embodiment is not limited to these.

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[0098] Among the above organometallic complexes, the exemplary compounds belonging to the AA and BB groups are compounds having at least a phenanthrene ring in the ligand of the Ir complex, and therefore, the fused ring constituting the ligand is formed of an SP2 hybrid orbital, making these compounds particularly stable.

[0099] Among the above organometallic complexes, the exemplary compounds belonging to the CC group are compounds having at least a triphenylene ring in the ligand of the Ir complex, and therefore, the fused ring constituting the ligand is formed of an SP2 hybrid orbital, making these compounds particularly stable.

[0100] Among the above organometallic complexes, the exemplary compounds belonging to the DD group are compounds having at least a dibenzofuran ring or a dibenzothiophene ring in the ligand of the Ir complex. Therefore, these compounds contain oxygen atoms and sulfur atoms in the fused rings constituting the ligand, and the abundant unshared electron pairs possessed by these atoms can enhance the charge transport property, making them particularly easy to adjust the carrier balance.

[0101] Among the above-mentioned organometallic complexes, the exemplary compounds belonging to the EE group and the GG group are compounds having at least a benzofluorene ring in the ligand of the Ir complex. Therefore, these compounds have a substituent at the 9-position of the fluorene, and therefore have a substituent in the direction perpendicular to the in-plane direction of the fluorene ring, which can particularly prevent the overlapping of fused rings. Therefore, these compounds have particularly excellent sublimation properties.

[0102] Among the above organometallic complexes, the exemplary compounds belonging to the HH group are compounds having at least a benzoisoquinoline ring in the ligand of the Ir complex. Therefore, these compounds have extended π-conjugation of the heterocyclic ring constituting the ligand, and are compounds that promote interaction with the host.

[0103] Among the above organometallic complexes, the exemplary compounds belonging to Group II are compounds having at least a naphthoisoquinoline ring in the ligand of the Ir complex, and therefore these compounds have extended π-conjugation of the heterocyclic ring constituting the ligand, which promotes interaction with the host.

[0104] <Organic light-emitting element> Next, the organic light-emitting device of this embodiment will be described. The organic light-emitting device of this embodiment has at least a pair of electrodes, an anode and a cathode, and an organic compound layer disposed between these electrodes. In the organic light-emitting device of this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers, as long as it has a light-emitting layer. Here, when the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have, in addition to the light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole / exciton blocking layer, an electron transport layer, an electron injection layer, etc. Furthermore, the light-emitting layer may be a single layer or a laminate consisting of multiple layers.

[0105] In the organic light-emitting device of this embodiment, at least one of the organic compound layers contains the organic compound of this embodiment. Specifically, the organic compound of this embodiment is contained in any of the above-mentioned light-emitting layer, hole injection layer, hole transport layer, electron blocking layer, hole / exciton blocking layer, electron transport layer, electron injection layer, etc. The organic compound of this embodiment is preferably contained in the light-emitting layer.

[0106] 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 solely of 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 or a guest of the light-emitting layer. It may also be used as an assist material that can be contained in the light-emitting layer. Here, the host is the compound with the largest mass ratio among the compounds constituting the light-emitting layer. Furthermore, the guest is a compound that is smaller in mass ratio than the host among the compounds constituting the light-emitting layer and is responsible for the main emission of light. Furthermore, the assist material is a compound that is smaller in mass 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.

[0107] When the organic compound according to this embodiment is used as a host in the light-emitting layer, the concentration of the host is preferably 50% by mass or more and 99% by mass or less, and more preferably 70% by mass or more and 99% by mass or less, based on the total mass of the light-emitting layer.

[0108] Furthermore, when the organic compound according to this embodiment is used as an assist material in the light-emitting layer, the concentration of the assist material is preferably 10% by mass or more and 49% by mass or less, and more preferably 15% by mass or more and 35% by mass or less, based on the total mass of the light-emitting layer.

[0109] Furthermore, 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 1% by mass or more and 20% by mass or less, and more preferably 5% by mass or more and 15% by mass or less, based on the total mass of the light-emitting layer.

[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 assist material for the light-emitting layer, particularly as a host for the light-emitting layer, a device exhibiting high efficiency and high luminance light output and extremely high durability can be obtained. This light-emitting layer may be a single layer or multiple layers. The light-emitting color of this embodiment is green, and a mixed color can be achieved by including a light-emitting material having another light-emitting color. "Multiple layers" refers to a state in which a first light-emitting layer and another light-emitting layer are stacked. The first light-emitting layer and the second light-emitting layer may emit different colors. Furthermore, the light-emitting color of the organic light-emitting device is not limited to green. More specifically, white light may be emitted, or an intermediate color may be emitted. In the case of white light emission, the second light-emitting layer emits a color other than green, i.e., blue or red. Furthermore, the film formation method is performed by vapor deposition or coating film formation. Details of this will be explained in detail in the examples below.

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

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

[0113] As the hole injection and transport material, a material with high hole mobility is preferred so that holes can be easily injected from the anode and the injected holes can be transported to the light-emitting layer. Furthermore, a material with a high glass transition temperature is preferred to reduce deterioration of film quality, such as crystallization, in organic light-emitting devices. Examples of low-molecular-weight and high-molecular-weight materials with hole injection and transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Furthermore, the above-mentioned hole injection and transport materials are also suitable for use in electron blocking layers. Specific examples of compounds that can be used as hole injection and transport materials are listed below, but the present invention is not limited to these. Specific examples of compounds that can be used as hole injecting and transporting materials are shown below, but the present invention is not limited to these.

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[0115] Examples of light-emitting materials mainly involved in light-emitting function include organic compounds represented by general formulas [1r-1] to [Ir-11], as well as 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. Specific examples of compounds that can be used as light-emitting materials are shown below, but the present invention is not limited to these.

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[0118] Examples of the emission layer host or emission assist material contained in the emission layer include, in addition to the organic compound of this embodiment represented by general formula [1], aromatic hydrocarbon compounds or derivatives thereof, carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, and organic beryllium complexes.

[0119] In particular, in the light-emitting layer containing the organic compound of this embodiment and the phosphorescent material, a third component, such as an assist material, is preferably a material having a carbazole skeleton, a material having an azine ring in its skeleton, or a material having a xanthone skeleton, because these materials have high electron-donating and electron-withdrawing properties and therefore facilitate adjustment of the HOMO level and LUMO level.

[0120] The organic compound of this embodiment is a compound in which an electron-donating moiety consisting of a crosslinked triphenylamine is bonded to an electron-withdrawing moiety consisting of a xanthone skeleton. Therefore, it is useful as a bipolar host, but it is preferable to add an assist material depending on the carrier balance of the entire device. Therefore, materials having the above skeleton that can adjust the HOMO level and LUMO level are particularly preferable as assist materials. When these assist materials are combined with the organic compound of this embodiment, a good carrier balance can be achieved.

[0121] Specific examples of compounds that can be used as the light-emitting layer host or light-emitting assist material contained in the light-emitting layer are shown below, but the present invention is not limited to these. Among the specific examples below, materials having a carbazole skeleton that are preferred as assist materials are EM32 to EM38. Materials having an azine ring in the skeleton that are preferred as assist materials are EM35 to EM40. Materials having a xanthone skeleton that are preferred as assist materials are EM28 and EM30.

[0122] [ka]

[0123] 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 taking into consideration the balance with the hole mobility of the hole transporting material, etc. Examples of materials having electron transport properties include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, and fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron transporting materials are also suitable for use in hole-blocking layers. Specific examples of compounds that can be used as electron transporting materials are shown below, but the present invention is not limited to these.

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[0125] [Configuration of organic light-emitting element] The organic light-emitting element is provided by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode on a substrate. A protective layer, a color filter, a microlens, etc. may be provided on the cathode. When a color filter is provided, a planarizing layer may be provided between the protective layer. The planarizing layer may be made of acrylic resin or the like. The same applies when a planarizing layer is provided between the color filter and the microlens.

[0126] [substrate] Examples of the substrate include quartz, glass, a silicon wafer, a resin, and a metal. Furthermore, the substrate may be provided with a switching element such as a transistor and wiring, and an insulating layer thereon. Any material can be used for the insulating layer, as long as it allows for the formation of a contact hole so that wiring can be formed between the first electrode and the insulating layer, and ensures insulation from wiring that is not connected. For example, resins such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0127] [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.

[0128] The anode material should have as high a work function as possible. Examples include simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, mixtures containing these metals, alloys of these metals, and metal oxides such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and zinc indium oxide. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0129] These electrode materials may be used alone or in combination of two or more. The anode may be composed of one layer or multiple layers.

[0130] When used as a reflective electrode, for example, chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used. The above materials can also function as a reflective film without functioning as an electrode. When used as a transparent electrode, transparent conductive oxide layers such as indium tin oxide (ITO) and indium zinc oxide can be used, but are not limited to these. Photolithography techniques can be used to form the electrode.

[0131] On the other hand, materials with a low work function are preferred for the cathode. Examples include alkali metals such as lithium, alkaline earth metals such as calcium, and metals such as aluminum, titanium, manganese, silver, lead, and chromium, as well as mixtures containing these metals. Alternatively, alloys combining these metals can be used. For example, magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, and zinc-silver can be used. Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials can be used alone or in combination. The cathode can have either a single-layer or multi-layer structure. Among these, silver is preferred, and a silver alloy is even more preferred to reduce silver aggregation. The alloy ratio is not critical as long as silver aggregation can be reduced. For example, the silver:other metal ratio can be 1:1, 3:1, or the like.

[0132] The cathode may be a top-emission element using an oxide conductive layer such as ITO, or a bottom-emission element using a reflective electrode such as aluminum (Al), and is not particularly limited. The method for forming the cathode is not particularly limited, but DC and AC sputtering methods are more preferred because they provide good film coverage and make it easier to reduce resistance.

[0133] [Organic compound layer] The organic compound layer may be formed as a single layer or as multiple layers. When multiple layers are included, they may be called hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, or electron injection layer depending on their functions. The organic compound layer is mainly composed of organic compounds but may also contain inorganic atoms or inorganic compounds. For example, the organic compound layer may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, or the like. The organic compound layer may be disposed between the first electrode and the second electrode, or may be disposed in contact with the first electrode and the second electrode.

[0134] [Protective layer] A protective layer may be provided on the cathode. For example, by adhering glass with a moisture absorbent on the cathode, the intrusion of water and other contaminants into the organic compound layer can be reduced, thereby reducing the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the cathode to reduce the intrusion of water and other contaminants into the organic compound layer. For example, after forming the cathode, the cathode may be transferred to another chamber without breaking the vacuum, and a 2 μm-thick silicon nitride film may be formed by CVD to serve as a protective layer. A protective layer may be provided using atomic layer deposition (ALD) after the CVD film formation. The material of the film formed by ALD is not limited, and may be silicon nitride, silicon oxide, aluminum oxide, or the like. Silicon nitride may be further formed on the film formed by ALD by CVD. The film formed by ALD may have a thickness smaller than that of the film formed by CVD. Specifically, the thickness may be 50% or less, or even 10% or less.

[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 a separate substrate and then bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer described above using photolithography technology. The color filter may be made of a polymer.

[0136] [Planarization layer] A planarization layer may be provided between the color filter and the protective layer. The planarization layer is provided for the purpose of reducing unevenness of the underlying layer. It may also be called a material resin layer without limiting its purpose. The planarization layer may be composed of an organic compound, and may be low molecular weight or high molecular weight, but is preferably high molecular weight. The planarization layers may be provided above and below the color filter, and may be made of the same or different materials. Specific examples include polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, and urea resin.

[0137] [Microlens] The organic light-emitting device may have an optical component such as a microlens on its light-emitting side. The microlens may be made of acrylic resin, epoxy resin, or the like. The microlens may be used to increase the amount of light extracted from the organic light-emitting device and to control the direction of the extracted light. The microlens may have a hemispherical shape. When the microlens has a hemispherical shape, among the tangents to the hemisphere, there is a tangent that is parallel to the insulating layer, and the point of contact between this tangent and the hemisphere is the vertex of the microlens. The vertex of the microlens can be determined in the same way in any cross-sectional view. In other words, among the tangents to the semicircle of the microlens in the cross-sectional view, there is a tangent that is parallel to the insulating layer, and the point of contact between this tangent and the semicircle is the vertex of the microlens.

[0138] It is also possible to define the midpoint of a microlens. In the cross section of the microlens, a line segment is imagined from the point where an arc shape ends to the point where another arc shape ends, and the midpoint of this line segment can be called the midpoint of the microlens. The cross section for determining the vertex and midpoint may be a cross section perpendicular to the insulating layer.

[0139] [Counter substrate] An opposing substrate may be provided on the planarization layer. The opposing substrate is called an opposing substrate because it is provided at a position corresponding to the aforementioned substrate. The constituent material of the opposing substrate may be the same as that of the aforementioned substrate. When the aforementioned substrate is defined as a first substrate, the opposing substrate may be a second substrate.

[0140] [Organic compound 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 of this embodiment are formed by the method shown below.

[0141] The organic compound layer can be formed by dry processes such as vacuum deposition, ionization deposition, sputtering, and plasma. Instead of a dry process, a wet process can be used in which the compound is dissolved in an appropriate solvent and a layer is formed by a known coating method (e.g., spin coating, dipping, casting, LB method, inkjet method, etc.). Forming a layer by vacuum deposition or solution coating, etc., makes it less likely to crystallize and provides excellent stability over time. When forming a film by a coating method, a film can also be formed by combining it with an appropriate binder resin.

[0142] Examples of the binder resin include, but are not limited to, polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, and urea resin. These binder resins may be used singly or in combination as homopolymers or copolymers. If necessary, known additives such as plasticizers, antioxidants, and ultraviolet absorbers may be used in combination.

[0143] [Pixel circuit] The light-emitting device may have a pixel circuit connected to the light-emitting element. The pixel circuit may be an active matrix type that controls the emission of the first light-emitting element and the second light-emitting element independently. The active matrix type circuit may be voltage-programmed or current-programmed. The drive circuit has a pixel circuit for each pixel. The pixel circuit may have a light-emitting element, a transistor that controls the emission brightness of the light-emitting element, a transistor that controls the emission timing, a capacitor that holds the gate voltage of the transistor that controls the emission brightness, and a transistor for connecting to GND without going through the light-emitting element.

[0144] The light-emitting device has a display area and a peripheral area arranged around the display area. The display area has a pixel circuit, and the peripheral area has a display control circuit. The mobility of a transistor constituting the pixel circuit may be smaller than the mobility of a transistor constituting the display control circuit. The slope of the current-voltage characteristics of the transistor constituting the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistor constituting the display control circuit. The slope of the current-voltage characteristics can be measured by the so-called Vg-Ig characteristics. The transistor constituting the pixel circuit is a transistor connected to a light-emitting element, such as a first light-emitting element.

[0145] [Pixels] An organic light emitting device having an organic light emitting element may have a plurality of pixels, each of which has sub-pixels that emit different colors, for example, RGB colors.

[0146] A pixel has an area, also called a pixel opening, that emits light. This area is the same as the first area. The pixel opening may be 15 μm or less, or 5 μm or more. More specifically, it may be 11 μm, 9.5 μm, 7.4 μm, 6.4 μm, etc. The distance between subpixels may be 10 μm or less, more specifically, it may be 8 μm, 7.4 μm, or 6.4 μm.

[0147] The pixels may be arranged in a known manner in a plan view. For example, they may be in a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement. The shape of the subpixels in a plan view may be any known shape. For example, they may be rectangular, quadrilaterals such as diamonds, or hexagons. Of course, a shape that is close to a rectangle, rather than an exact shape, is included in the rectangle. The shape of the subpixels and the pixel arrangement may be used in combination.

[0148] <Applications of organic light-emitting devices> The organic light-emitting device according to this embodiment can be used as a component of a display device or a lighting device, and can also be used as an exposure light source for an electrophotographic image forming device, a backlight for a liquid crystal display device, or a light-emitting device having a white light source and a color filter.

[0149] The display device may be an image information processing device that has an image input unit that inputs image information from an area CCD, a linear CCD, a memory card, etc., has 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, at least one of which may have the organic light-emitting element of this embodiment and a transistor connected to the organic light-emitting element.

[0150] The display unit of the imaging device or inkjet printer may have a touch panel function. The driving method of this touch panel function may be an infrared method, a capacitance method, a resistive film method, or an electromagnetic induction method, and is not particularly limited. The display device may also be used in the display unit of a multifunction printer.

[0151] Next, the display device according to this embodiment will be described with reference to the drawings. Fig. 4 is a cross-sectional view showing an example of a display device having an organic light-emitting element and a transistor connected to the organic light-emitting element. The transistor is an example of an active element. The transistor may be a thin film transistor (TFT).

[0152] FIG. 4(a) shows an example of a pixel, which is a component of the display device according to this embodiment. The pixel includes sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B based on their light emission. The emitted colors may be distinguished by the wavelength of light emitted from the light-emitting layer, or the light emitted from the sub-pixels may be selectively transmitted or color-converted using a color filter or the like. Each sub-pixel 10 includes a reflective electrode serving as a first electrode 2 on an interlayer insulating layer 1, an insulating layer 3 covering the edges of the first electrode 2, an organic compound layer 4 covering the first electrode 2 and the insulating layer 3, a transparent electrode serving as a second electrode 5, a protective layer 6, and a color filter 7.

[0153] A transistor and a capacitor may be disposed below or inside the interlayer insulating layer 1. The transistor and the first electrode may be electrically connected via a contact hole or the like (not shown).

[0154] The insulating layer 3 is also called a bank or a pixel separation film. It covers the edges of the first electrode 2 and is disposed to surround the first electrode 2. The portion where the insulating layer 3 is not disposed is in contact with the organic compound layer 4 and becomes a light-emitting region.

[0155] The organic compound layer 4 includes a hole injection layer 41 , a hole transport layer 42 , a first light-emitting layer 43 , a second light-emitting layer 44 , and an electron transport layer 45 .

[0156] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0157] The protective layer 6 reduces the penetration of moisture into the organic compound layer 4. Although the protective layer 6 is illustrated as being one layer, it may be multiple layers, and each layer may be an inorganic compound layer and an organic compound layer.

[0158] The color filters 7 are divided into 7R, 7G, and 7B depending on their colors. The color filters 7 may be formed on a planarization film (not shown). A resin protective layer (not shown) may be provided on the color filters 7. The color filters 7 may be formed on the protective layer 6. Alternatively, the color filters 7 may be provided on an opposing substrate such as a glass substrate and then bonded thereto.

[0159] The display device 100 in FIG. 4(b) has an organic light-emitting element 26 and a TFT 18 as an example of a transistor. A substrate 11 made of glass, silicon, or the like is provided with an insulating layer 12 on top of it. An active element such as the TFT 18 is disposed on the insulating layer 12, and a gate electrode 13, a gate insulating film 14, and a semiconductor layer 15 of the active element are disposed on top of it. The TFT 18 also comprises a drain electrode 16 and a source electrode 17. An insulating film 19 is provided on top of the TFT 18. An anode 21 constituting the organic light-emitting element 26 and the source electrode 17 are connected via a contact hole 20 provided in the insulating film 19.

[0160] The electrical connection method between the electrodes (anode 21, cathode 23) included in the organic light-emitting element 26 and the electrodes (source electrode 17, drain electrode 16) included in the TFT 18 is not limited to the embodiment shown in Fig. 4(b). In other words, it is sufficient that either the anode 21 or the cathode 23 is electrically connected to either the source electrode 17 or the drain electrode 16 of the TFT 18. TFT stands for thin film transistor.

[0161] 4(b), the organic compound layer 22 is illustrated as a single layer, but may be a multi-layer organic compound layer 22. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce deterioration of the organic light-emitting element 26.

[0162] In the display device 100 of FIG. 4(b), transistors are used as switching elements, but other switching elements may be used instead.

[0163] The transistors used in the display device 100 of Fig. 4(b) are not limited to transistors using single-crystal silicon wafers, but may also be thin-film transistors having an active layer on the insulating surface of a substrate. Examples of active layers include non-single-crystal silicon such as single-crystal silicon, amorphous silicon, and microcrystalline silicon, and non-single-crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Thin-film transistors are also called TFT elements.

[0164] The transistors included in the display device 100 of Fig. 4(b) may be formed within a substrate such as a Si substrate. Here, "formed within a substrate" means that the substrate itself, such as a Si substrate, is processed to form the transistors. In other words, having a transistor within a substrate can be seen as the substrate and the transistor being formed integrally.

[0165] The organic light-emitting element according to this embodiment has its emission brightness controlled by a TFT, which is an example of a switching element. By providing multiple organic light-emitting elements on a surface, an image can be displayed based on the emission brightness of each element. The switching element according to this embodiment is not limited to a TFT, but may also be a transistor formed from low-temperature polysilicon or an active matrix driver formed on a substrate such as a Si substrate. "On the substrate" can also be referred to as "inside the substrate." Whether to provide a transistor within the substrate or to use a TFT is determined by the size of the display unit. For example, for a display size of about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0166] FIG. 5(a) is a schematic diagram showing an example of an image forming apparatus according to one embodiment of the present invention. The image forming apparatus 40 is an electrophotographic image forming apparatus and includes a photoconductor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fixing unit 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoconductor 27 (on the photoconductor). The exposure light source 28 includes an organic light-emitting element according to this embodiment. The developing unit 31 includes toner and the like. The charging unit 30 charges the photoconductor 27. The transfer unit 32 transfers the developed image to a recording medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fixing unit 35 fixes the image formed on the recording medium 34.

[0167] 5(b) and 5(c) are schematic diagrams showing an exposure light source 28, each illustrating a plurality of light-emitting units 36, each of which is an organic light-emitting element according to this embodiment, arranged on a long substrate. Arrow 37 indicates the direction parallel to the axis of the photoconductor 27, representing the column direction in which the light-emitting units 36 are arranged. This column direction is the same as the axis direction about which the photoconductor 27 rotates. This direction can also be referred to as the long axis direction of the photoconductor 27. FIG. 5(b) shows a configuration in which the light-emitting units 36 are arranged along the long axis direction of the photoconductor 27. FIG. 5(c) shows a different configuration from FIG. 5(b), in which the light-emitting units 36 are arranged alternately in the column direction in the first and second columns. The first and second columns are arranged at different positions in the row direction. The first column includes multiple light-emitting units 36 spaced apart. The second column includes light-emitting units 36 at positions corresponding to the spacing between the light-emitting units 36 in the first column. That is, the light-emitting units 36 are also arranged at intervals in the row direction. The arrangement in Fig. 5(c) can also be described as a grid-like arrangement, a houndstooth arrangement, or a checkerboard pattern.

[0168] 6 is a schematic diagram illustrating an example of a display device according to this embodiment. The display device 1000 may include a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. The touch panel 1003 and the display panel 1005 are connected by flexible printed circuits FPCs 1002 and 1004. Transistors are printed on the circuit board 1007. The battery 1008 may not be provided if the display device is not a portable device, and may be provided in a different position even if the display device is a portable device.

[0169] The display device according to this embodiment may have color filters having red, green, and blue colors, which may be arranged in a delta arrangement.

[0170] The display device according to the present embodiment may be used as a display unit of a mobile terminal. In this case, the display device may have both a display function and an operation function. Examples of the mobile terminal include a mobile phone such as a smartphone, a tablet, and a head-mounted display.

[0171] The display device according to this embodiment may be used as a display unit of an imaging device having an optical unit with a plurality of lenses and an imaging element that receives light that has passed through the optical unit. The imaging device may have a display unit that displays information acquired by the imaging element. The display unit may be a display unit exposed to the outside of the imaging device or a display unit disposed within a viewfinder. The imaging device may be a digital camera or a digital video camera.

[0172] 7(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 speed at which the subject is moving, the possibility that the subject will be blocked by an obstruction, and the like.

[0173] Since the optimum timing for capturing an image is very short, it is better to display information as soon as possible. Therefore, it is preferable to use a display device using the organic light-emitting element of this embodiment. This is because the organic light-emitting element has a fast response speed. A display device using the organic light-emitting element can be used more preferably than a liquid crystal display device, which requires a high display speed.

[0174] The imaging device 1100 has an optical section (not shown). The optical section has multiple lenses, which form an image on an imaging element housed in a housing 1104. The focus of the multiple lenses can be adjusted by adjusting their relative positions. This operation can also be performed automatically. The imaging device may also be called a photoelectric conversion device. Instead of sequentially capturing images, the photoelectric conversion device can include an imaging method that detects the difference from the previous image, or a method of cutting out an image from a constantly recorded image, etc.

[0175] FIG. 7(b) is a schematic diagram illustrating an example of an electronic device according to this embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type reaction unit. The operation unit 1202 may be a biometric recognition unit that recognizes a fingerprint to perform operations such as unlocking. An electronic device having a communication unit can also be called a communication device. The electronic device 1200 may further have a camera function by including a lens and an image sensor. An image captured by the camera function is displayed on the display unit 1201. Examples of the electronic device 1200 include a smartphone and a laptop computer.

[0176] FIG. 8 is a schematic diagram illustrating an example of a display device according to this embodiment. FIG. 8(a) illustrates a display device such as a television monitor or a PC monitor. The display device 1300 has a frame 1301 and a display unit 1302. The display unit 1302 may use a light-emitting element according to this embodiment. The display device 1300 has the frame 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in FIG. 8(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.

[0177] FIG. 8(b) is a schematic diagram illustrating another example of a display device according to this embodiment. The display device 1310 in FIG. 8(b) is configured to be bendable, and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may include light-emitting elements according to this embodiment. The first display unit 1311 and the second display unit 1312 may be a single, seamless display unit. The first display unit 1311 and the second display unit 1312 can be separated by the bending point. The first display unit 1311 and the second display unit 1312 may each display different images, or the first and second display units may display a single image.

[0178] FIG. 9(a) is a schematic diagram illustrating an example of a lighting device according to this embodiment. The lighting device 1400 may include a housing 1401, a light source 1402, a circuit board 1403, an optical filter 1404 that transmits light emitted by the light source 1402, and a light diffusion unit 1405. The light source 1402 may include an organic light-emitting element according to this embodiment. The optical filter 1404 may be a filter that improves the color rendering of the light source. The light diffusion unit 1405 can effectively diffuse light from the light source, such as for illumination, and deliver the light over a wide area. The optical filter 1404 and the light diffusion unit 1405 may be provided on the light emission side of the lighting. If necessary, a cover may be provided on the outermost part.

[0179] The lighting device is, for example, a device that illuminates a room. The lighting device may emit white, daylight white, or any other color from blue to red. It may have a dimming circuit that dims these colors. 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 to DC voltage. Furthermore, white has a color temperature of 4200K, and daylight white has a color temperature of 5000K. The lighting device may have a color filter.

[0180] The lighting device according to this embodiment may also include a heat dissipation unit, which dissipates heat from within the device to the outside, and may be made of a material such as a metal with a high specific heat capacity or liquid silicon.

[0181] 9(b) is a schematic diagram of an automobile, which is an example of a moving body according to this embodiment. The automobile has tail lamps, which are an example of lighting fixtures. The automobile 1500 has tail lamps 1501, and may be configured to turn on the tail lamps when braking or the like is performed.

[0182] The tail lamp 1501 may include an organic light-emitting element according to this embodiment. The tail lamp 1501 may include a protective member for protecting the organic light-emitting element. The protective member may be made of any material as long as it has a certain degree of strength and is transparent, but is preferably made of polycarbonate or the like. Polycarbonate may be mixed with a furandicarboxylic acid derivative, an acrylonitrile derivative, or the like.

[0183] The automobile 1500 may have a body 1503 and a window 1502 attached thereto. The window 1502 may be a transparent display as long as it is not a window for checking the front and rear of the automobile. The transparent display may have an organic light-emitting element according to this embodiment. In this case, the constituent materials of the electrodes and the like of the organic light-emitting element are made of transparent materials.

[0184] The moving body according to this embodiment may be a ship, an aircraft, a drone, or the like. The moving body may have a body and a lighting device provided on the body. The lighting device may emit light to indicate the position of the body. The lighting device has the organic light-emitting element according to this embodiment.

[0185] An application example of the display device of each of the above-described embodiments will be described with reference to Fig. 10. The display device can be applied to a system that can be attached as a wearable device, such as smart glasses, an HMD, or a smart contact lens. An image capturing and displaying device used in such an application example includes an image capturing device capable of photoelectrically converting visible light and a displaying device capable of emitting visible light.

[0186] Fig. 10(a) is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention. Using Fig. 10(a), glasses 1600 (smart glasses) according to one application example will be described. An imaging device 1602 such as a CMOS sensor or SPAD is provided on the front side of a lens 1601 of the glasses 1600. In addition, a display device according to each of the above-mentioned embodiments is provided on the back side of the lens 1601.

[0187] The glasses 1600 further include a control device 1603. The control device 1603 functions as a power source that supplies power to the image capture device 1602 and the display device. The control device 1603 also controls the operations of the image capture device 1602 and the display device. The lens 1601 is formed with an optical system for focusing light onto the image capture device 1602.

[0188] FIG. 10(b) is a schematic diagram showing another example of a wearable device according to an embodiment of the present invention. Using FIG. 10(b), glasses 1610 (smart glasses) according to one application example will be described. The glasses 1610 have a control device 1612, which is equipped with an imaging device corresponding to the imaging device 1602 in FIG. 10(a) and a display device. A lens 1611 is formed with an optical system for projecting light emitted from the imaging device in the control device 1612 and the display device, and an image is projected onto the lens 1611. The control device 1612 functions as a power source that supplies power to the imaging device and the display device, and controls the operation of the imaging device and the display device.

[0189] The control device 1612 may include a gaze detection unit that detects the wearer's gaze. The gaze detection may use infrared light. The infrared light emitter emits infrared light toward the eyeball of the user gazing at the display image. An imaging unit with a light-receiving element detects the reflected infrared light from the eyeball, thereby obtaining a captured image of the eyeball. A reduction unit that reduces light from the infrared light emitter to the display unit in a planar view reduces degradation of image quality. The user's gaze toward the displayed image is detected from the captured image of the eyeball obtained by capturing infrared light. Any known method can be applied to gaze detection using the captured image of the eyeball. As an example, a gaze detection method based on a Purkinje image formed by reflection of irradiated light on the cornea can be used. More specifically, gaze detection processing based on the pupil-corneal reflex method is performed. Using the pupil-corneal reflex method, a gaze vector representing the orientation (rotation angle) of the eyeball is calculated based on the image of the pupil and the Purkinje image included in the captured image of the eyeball, thereby detecting the user's gaze.

[0190] A display device according to one embodiment of the present invention may include an imaging device having a light receiving element, and may control the display image of the display device based on user line-of-sight information from the imaging device. Specifically, the display device determines a first field of view area where the user gazes and a second field of view area other than the first field of view area based on the line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be determined by an external control device and received. In the display area of ​​the display device, the display resolution of the first field of view area may be controlled to be higher than the display resolution of the second field of view area. In other words, the resolution of the second field of view area may be lower than that of the first field of view area.

[0191] The display area includes a first display area and a second display area different from the first display area, and a high-priority area is determined from the first display area and the second display area based on line-of-sight information. The first field of view area and the second field of view area may be determined by a control device of the display device, or may be determined by an external control device and received. The resolution of the high-priority area may be controlled to be higher than the resolution of areas other than the high-priority area. In other words, the resolution of an area with a relatively low priority may be lowered.

[0192] Note that AI may be used to determine the first field of view area or the area with high priority. The AI ​​may be a model configured to estimate the angle of gaze and the distance to an object in the line of sight from the image of the eyeball, using as training data an image of the eyeball and the direction in which the eyeball in the image was actually looking. The AI ​​program may be included in the display device, the imaging device, or an external device. If included in the external device, it is transmitted to the display device via communication.

[0193] When display control is performed based on visual recognition detection, the smart glasses can be preferably applied to smart glasses that further include an imaging device for capturing images of the outside world. The smart glasses can display captured external information in real time.

[0194] As described above, by using a device using the organic light-emitting element according to this embodiment, it is possible to provide a stable display with good image quality even over a long period of time. [Example]

[0195] The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

[0196] [Example 1 (Synthesis of Exemplary Compound A4)] [ka]

[0197] (1) Synthesis of compound m-3 The following reagents and solvents were placed in a 200 ml recovery flask. Compound m-1: 5.0g (27.3mmol) Compound m-2: 7.5g (30.0mmol) Copper: 1.7g (27.3mmol) Potassium carbonate: 3.8g (27.3mmol) Sodium sulfate: 3.9 g (27.3 mmol) Nitrobenzene: 100ml Next, this reaction solution was heated and stirred under nitrogen at 220 °C for 7 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and ethyl acetate was added to the resulting residue. After washing with an aqueous ammonium chloride solution, the organic layer was concentrated under reduced pressure to obtain a crude product. Next, this crude product was purified by silica gel column chromatography (chloroform), yielding 7.5 g (yield: 78%) of compound m-3 as a white solid.

[0198] (2) Synthesis of compound m-5 The following reagents and solvents were placed in a 200 ml recovery flask. Compound m-3: 5.0g (14.2mmol) Dehydrated tetrahydrofuran: 150 ml Next, 42.6 ml (42.6 mmol) of a 1.0 M methylmagnesium bromide solution (tetrahydrofuran) represented by m-4 above was added dropwise to this reaction solution at an internal temperature of 0°C under nitrogen. The reaction solution was then warmed to room temperature and stirred at this temperature (room temperature) for 5 hours. After completion of the reaction, toluene was added to the reaction solution, which was then washed with saturated brine. The organic layer was concentrated under reduced pressure to obtain a crude product. The crude product was then purified by silica gel column chromatography (chloroform) to obtain 4.1 g (yield 82%) of compound m-5.

[0199] (3) Synthesis of compound m-6 The following reagents and solvents were placed in a 200 ml recovery flask. Compound m-5: 4.0g (11.4mmol) Polyphosphate: 35ml Next, this reaction solution was heated and stirred at 205°C under nitrogen for 2 hours. After the reaction was completed, the reaction solution was allowed to cool. Next, toluene was added to the reaction solution, and the mixture was neutralized and washed with aqueous sodium carbonate solution. The organic layer was then concentrated under reduced pressure to obtain a crude product. Next, this crude product was purified by column chromatography (NH gel) to obtain 1.0 g of compound m-6 (yield 27%).

[0200] (4) Synthesis of compound m-7 The following reagents and solvents were placed in a 200 ml recovery flask. Compound m-6: 1.0g (3.0mmol) Bis(pinacolato)diboron: 0.9g (3.6mmol) Bis(dibenzylideneacetone)palladium(0): 0.3 g (0.6 mmol) 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos): 0.5g (1.2mmol) Potassium acetate: 0.9 g (9.0 mmol) Dehydrated 1,4-dioxane: 50 ml Next, this reaction solution was heated and stirred at 125°C under nitrogen for 7 hours. After the reaction was completed, the reaction solution was allowed to cool. Next, toluene was added to the reaction solution, and the mixture was washed with saturated saline. The organic layer was then concentrated to obtain a crude product. Next, this crude product was purified by column chromatography (chloroform) to obtain 0.9 g of compound m-7 (yield 72%).

[0201] (3) Synthesis of Compound A4 The following reagents and solvents were placed in a 200 ml recovery flask. Compound m-7: 0.9g (2.1mmol) Compound m-8: 0.8g (2.5mmol) Bis(dibenzylideneacetone)palladium(0): 0.2 g (0.4 mmol) 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos): 0.4g (0.8mmol) Potassium phosphate: 1.4g (6.3mmol) Toluene: 50 ml H2O: 5ml The reaction solution was then heated under reflux under a nitrogen stream and stirred 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:heptane) and then recrystallized from toluene / heptane to obtain 0.8 g (yield: 65%) of exemplary compound A4 as a pale yellow solid.

[0202] The obtained exemplary compound A4 was subjected to mass spectrometry using MALDI-TOF-MS (Bruker Autoflex LRF). 40 H 27 The calculated value obtained from NO3 was 569, while the measured value (m / z) was 569, which agreed.

[0203] [Examples 2 to 10 (Synthesis of Exemplary Compounds)] The exemplary compounds of Examples 2 to 10 shown in Table 4 were synthesized in the same manner as in Example 1, except that compounds m-1, m-2, and m-8 in Example 1 were replaced with the compounds shown in Table 4. The actual measured values ​​(m / z) of the mass spectrometry results measured in the same manner as in Example 1 are also shown.

[0204] [Table 4]

[0205] Example 11 (Synthesis of Exemplary Compound B6) [ka]

[0206] (1) Synthesis of compound n-3 The following reagents and solvents were placed in a 500 ml recovery flask. Compound n-1: 10.0g (61.1mmol) Compound n-2: 34.3g (183.4mmol) Copper: 11.6g (183.4mmol) Potassium carbonate: 25.4g (183.4mmol) Sodium sulfate: 8.61 g (183.4 mmol) Nitrobenzene: 200ml Next, this reaction solution was heated and stirred under nitrogen at 220°C for 7 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and ethyl acetate was added to the resulting residue. After washing with an aqueous ammonium chloride solution, the organic layer was concentrated under reduced pressure to obtain a crude product. Next, this crude product was purified by column chromatography (chloroform) to obtain 16.8 g (yield: 73%) of compound n-3 as a brownish-white solid.

[0207] (2) Synthesis of compound n-4 The following reagents and solvents were placed in a 200 ml recovery flask. Compound n-3: 15.0g (39.9mmol) Pyridine hydrochloride: 220g The reaction solution was then heated under reflux under a nitrogen atmosphere and stirred 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:heptane) and recrystallized from toluene / heptane to obtain 11.2 g (yield: 81%) of compound n-4 as a white solid.

[0208] (3) Synthesis of compound n-5 The following reagents and solvents were placed in a 500 ml recovery flask. Compound n-4: 10.0g (28.8mol) Potassium carbonate: 11.9g (86.3mmol) N,N-dimethylformamide: 300 ml Next, this reaction solution was heated under reflux and stirred under nitrogen for 7 hours. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and ethyl acetate was added to the resulting residue. After washing with an aqueous ammonium chloride solution, the organic layer was concentrated under reduced pressure to obtain a crude product. Next, this crude product was purified by column chromatography (chloroform) to obtain 6.0 g (yield: 68%) of compound n-5 as a white solid.

[0209] (4) Synthesis of compound n-6 The following reagents and solvents were placed in a 500 ml recovery flask. Compound n-5: 5.0g (16.2mmol) Bis(pinacolato)diboron: 4.9g (19.5mmol) Bis(dibenzylideneacetone)palladium(0): 1.8 g (3.2 mmol) 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos): 2.7g (6.5mmol) Potassium acetate: 4.8g (48.7mmol) Dehydrated 1,4-dioxane: 250 ml Next, this reaction solution was heated and stirred at 125°C under nitrogen for 7 hours. After the reaction was completed, the reaction solution was allowed to cool. Next, toluene was added to the reaction solution, and the mixture was washed with saturated saline, and then the organic layer was concentrated to obtain a crude product. Next, this crude product was purified by column chromatography (chloroform) to obtain 4.5 g of compound n-6 ​​(yield 65%).

[0210] (5) Synthesis of Compound B4 The following reagents and solvents were placed in a 200 ml recovery flask. Compound n-6: 1.0g (2.5mmol) Compound n-7: 1.0g (2.5mmol) Bis(dibenzylideneacetone)palladium(0): 0.3 g (0.5 mmol) 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos): 0.4g (1.0mmol) Potassium phosphate: 1.6g (0.8mmol) Toluene: 50 ml H2O: 5ml The reaction solution was then heated under reflux under a nitrogen stream and stirred 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:heptane) and then recrystallized from toluene / heptane to obtain 0.7 g (yield: 61%) of exemplary compound B4 as a pale yellow solid.

[0211] The obtained exemplary compound B6 was subjected to mass spectrometry in the same manner as in Example 1. As a result, C 31 H 17 The calculated value obtained from NO4 was 467, while the measured value (m / z) was 467, which agreed.

[0212] [Examples 12 to 20 (Synthesis of Exemplary Compounds)] The exemplary compounds of Examples 12 to 20 shown in Table 5 were synthesized in the same manner as in Example 11, except that compounds n-5 and n-7 in Example 11 were replaced with the compounds shown in Table 5. The actual measured values ​​(m / z) of the mass spectrometry results measured in the same manner as in Example 11 are also shown.

[0213] [Table 5]

[0214] [Comparative Examples 1 and 2 (Synthesis of Comparative Compounds)] According to the following synthesis scheme, organic compounds, comparative compounds 1 and 2, were synthesized. Comparative compound 1 is a compound described in Patent Document 1, and comparative compound 2 is an analogous compound to the compound described in Patent Document 2.

[0215] [ka]

[0216] (1) Synthesis of comparative compound 1 The following reagents and solvents were placed in a 200 ml recovery flask. Compound p-1: 1.0g (2.8mmol) Compound p-2: 1.2g (7.1mmol) Pd(dba)2: 0.3g xphos:0.5g tBuONa: 0.7 g (7.1 mmol) Xylene: 50 ml The reaction solution was then heated under reflux under a nitrogen stream and stirred 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:heptane) and recrystallized from toluene / heptane to obtain 0.7 g (yield: 45%) of comparative compound 1 as a white solid.

[0217] The obtained comparative compound 1 was subjected to mass spectrometry in the same manner as in Example 1. 37 H 22 The calculated value obtained from N2O2 was 526, and the measured value (m / z) was 526, which agreed.

[0218] (1) Synthesis of comparative compound 2 The following reagents and solvents were placed in a 200 ml recovery flask. Compound p-3: 1.0g (2.8mmol) Compound p-2: 1.3g (7.1mmol) Pd(dba)2: 0.3g xphos:0.5g tBuONa: 0.7 g (7.1 mmol) Xylene: 50 ml The reaction solution was then heated under reflux under a nitrogen stream and stirred for 6 hours. After the reaction was completed, water was added to separate the solution, which was then dissolved in chloroform. The resulting solution was purified by column chromatography (chloroform:heptane) and recrystallized from toluene / heptane to obtain 0.9 g (yield: 55%) of comparative compound 2 as a white solid.

[0219] The obtained comparative compound 2 was subjected to mass spectrometry in the same manner as in Example 1. 37 H 22 The calculated value obtained from N2O4 was 558, and the measured value (m / z) was 558, which agreed.

[0220] [Example 21] An organic light-emitting device with a bottom emission structure was fabricated by sequentially forming 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 on a substrate.

[0221] First, an ITO film was formed on a glass substrate and then patterned as desired 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 the ITO substrate in the following process. Next, a 1.33 × 10 -4 Vacuum deposition was performed by resistance heating in a vacuum chamber at 100 Pa to successively form the organic compound layer and electrode layer shown in Table 6 on the ITO substrate. At this time, the electrode area of ​​the opposing electrode (metal electrode layer, cathode) was 3 mm 2 It was made to be like this.

[0222] [Table 6]

[0223] The properties of the obtained organic light-emitting device were measured and evaluated. The maximum emission wavelength of the light-emitting device was 522 nm, and the maximum external quantum efficiency (EQE) was 13%. Furthermore, at a current density of 100 mA / cm 2 A continuous driving test was conducted at 100°C, and the time (LT95) at which the luminance degradation rate reached 5% was measured. When the LT95 of Comparative Example 1 was taken as 1.0, the luminance degradation rate ratio of this example (LT95 of Example 21 / LT95 of Comparative Example 1) was 1.4. As for the measuring equipment, the current-voltage characteristics were measured using a microcurrent meter "4140B" manufactured by Hewlett-Packard, and the luminance was measured using a "BM7" manufactured by Topcon Corporation.

[0224] [Examples 22 to 38, Comparative Examples 3 and 4] An organic light-emitting device was produced in the same manner as in Example 21, except that the compounds were appropriately changed to those shown in Table 7. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 21. The measurement results are shown in Table 7.

[0225] [Table 7]

[0226] As can be seen from Table 7, the maximum external quantum efficiencies (EQE) of Comparative Examples 3 and 4 were 8% and 5%, respectively, and the light-emitting device of this embodiment had a higher luminous efficiency. This is because the exemplary compound of this embodiment has a smaller T1 energy. Furthermore, the light-emitting device of this embodiment had a longer life. This is because the exemplary compound of this embodiment has better film properties and bonding stability. From the above, by using the exemplary compound of this embodiment, it is possible to provide a device that is highly efficient and has excellent durability characteristics.

[0227] [Example 39] An organic light-emitting device was produced in the same manner as in Example 21, except that the organic compound layer and the electrode layer shown in Table 8 were successively formed.

[0228] [Table 8]

[0229] The characteristics of the obtained organic light-emitting device were measured and evaluated in the same manner as in Example 21. The light-emitting device emitted green light, and the maximum external quantum efficiency (EQE) was 18%. Furthermore, when a continuous driving test was carried out in the same manner as in Example 21, the luminance degradation rate ratio of Example 39 was 2.5, where LT95 of Comparative Example 3 was 1.0.

[0230] [Examples 40 to 63] An organic light-emitting device was produced in the same manner as in Example 39, except that the compounds were appropriately changed to those shown in Table 9. The characteristics of the obtained light-emitting device were measured and evaluated in the same manner as in Example 39. The measurement results are shown in Table 9.

[0231] [Table 9] [Explanation of symbols]

[0232] 2: first electrode, 4, 22: organic compound layer, 5: second electrode, 21: anode, 23: cathode, 26: organic light-emitting element, 28: exposure light source, 40: image forming apparatus, 100: display device, 1201, 1302, 1311, 1312: display unit, 1404: optical filter, 1045: light diffusion unit, 1601: lens

Claims

1. An organic compound represented by the following general formula [1]: 【Chemistry 1】 In the above formula [1], R 1 ~R 19 are each independently selected from a hydrogen atom, a deuterium 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 heteroaryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, and a cyano group; R 9 and R 19 may be bonded. 9 and R 19 is bonded, it is a direct bond, a bond via an oxygen atom, a bond via a sulfur atom, CR 20 R 21 The bond is selected from bonds via R 20 , R 21 are each independently the R 1 ~R 19 is the same as X 1 , X 2 are each independently an oxygen atom, a sulfur atom, or CR 20 R 21 or a single bond, and when one of X 1 and X 2 is a single bond, the other is an oxygen atom, a sulfur atom, or CR 20 C 21 . Ar represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group. n represents an integer of 1 or 2. m represents an integer of 1 or more and 4 or less. When the alkyl group, alkoxy group, amino group, aryloxy group, heteroaryloxy group, silyl group, aromatic hydrocarbon group, or heterocyclic group has a substituent, the substituent may be any of fluorine, chlorine, bromine, iodine, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, tertiary butyl group, methoxy group, ethoxy group, propoxy group, dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, ditolylamino group, phenoxy group, phenyl group, biphenyl group, pyridyl group, pyrrolyl group, cyano group, and deuterium atom.

2. The m is 1, and the R to R 19 and any one of the above R 2 , R 3 , R 6 , R 7 The organic compound according to claim 1, characterized in that any one of the following is bonded.

3. The X 1 , X 2 At least one of the following is CR 20 R 21 3. The organic compound according to claim 1, wherein

4. The X 1 , X 2 4. The organic compound according to claim 1, wherein at least one of the groups is an oxygen atom or a sulfur atom.

5. 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 contains the organic compound according to claim 1 .

6. 6. The organic light-emitting element according to claim 5, wherein at least one of the organic compound layers is a light-emitting layer.

7. 7. The organic light-emitting element according to claim 6, wherein the light-emitting layer contains a phosphorescent material, and the organic compound is contained in the light-emitting layer in an amount of 10% by mass to 99% by mass.

8. 8. The organic light-emitting element according to claim 7, wherein the organic compound is contained as a host material in the light-emitting layer in an amount of 50% by mass to 99% by mass.

9. 8. The organic light-emitting element according to claim 7, wherein the organic compound is contained as an assist material in the light-emitting layer in an amount of 10% by mass to 49% by mass.

10. 10. The organic light-emitting element according to claim 7, wherein the phosphorescent material is an organometallic complex having a ligand having at least three or more fused rings.

11. The organic light-emitting device according to claim 10, wherein the organometallic complex is represented by the following general formula [2]: Ir(L) m (L') n (L”) r [2] In the above formula [2], L, L', and L" each represent a different bidentate ligand. m is selected from an integer of 1 or more and 3 or less, and n and r are each independently selected from an integer of 0 or more and 2 or less, provided that m+n+r=3. The Ir(L) m is represented by any one of the following general formulas [Ir-1] to [Ir-11]. 【Chemistry 2】 【Transformation 3】 In the above formulas [Ir-1] to [Ir-11], Ar 1 , Ar 2 are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, p and q are integers of 0 to 4, and X is selected from an oxygen atom, a sulfur atom, or a carbon atom optionally substituted with any of an alkyl group, CD3, CF3, and a phenyl group. The L may further have a deuterium atom, a fluorine atom, a substituted or unsubstituted alkyl group, a deuterium-substituted alkyl group, an alkoxy group, a silyl group, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. When the alkyl group, aryl group, or heterocyclic group has a substituent, the substituent may be any of fluorine, chlorine, bromine, iodine, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a tertiary butyl group, a methoxy group, an ethoxy group, a propoxy group, a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, a ditolylamino group, a phenoxy group, a phenyl group, a biphenyl group, a pyridyl group, a pyrrolyl group, a cyano group, and a deuterium atom.

12. 12. The organic light-emitting element according to claim 7, wherein the light-emitting layer contains the organic compound, the phosphorescent material, and a third component different from the organic compound and the phosphorescent material.

13. The organic light-emitting element according to claim 12 , wherein the third component has at least a carbazole skeleton.

14. The organic light-emitting device according to claim 12, wherein the third component has at least an azine ring in its skeleton.

15. The organic light-emitting device according to claim 12 , wherein the third component has at least a xanthone skeleton.

16. 16. The organic light-emitting device according to claim 6, further comprising a second light-emitting layer disposed by stacking the light-emitting layer as a first light-emitting layer, wherein the second light-emitting layer emits light of a color different from the light color emitted by the first light-emitting layer.

17. 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 5 and a transistor connected to the organic light-emitting element.

18. 17. An image forming apparatus having a photosensitive member, a light source that exposes the photosensitive member, and a developing unit that develops a latent image formed on the photosensitive member by the light source, wherein the light source is an exposure light source for an electrophotographic image forming apparatus that uses the organic light-emitting element according to claim 5.

19. an optical unit having a plurality of lenses, an image pickup element that receives light that has passed through the optical unit, and a display unit that displays an image picked up by the image pickup element; The photoelectric conversion device, wherein the display section comprises the organic light-emitting element according to claim 5 .

20. 17. An electronic device comprising: a display unit having the organic light-emitting element according to claim 5; a housing in which the display unit is provided; and a communication unit provided in the housing and communicating with an external device.

21. 17. A lighting device comprising: a light source having the organic light-emitting element according to claim 5; and a light diffusion section or an optical filter that transmits light emitted by the light source.

22. A moving body comprising: a lamp having the organic light-emitting element according to claim 5; and a body on which the lamp is provided.

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