Organic compound and organic light-emitting device

Abstract

To provide an organic compound that has high chemical stability and can be suitable as a material for an organic light-emitting device.SOLUTION: An organic compound is represented by a general formula [1] where R1 to R14 are each independently selected from a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an amino group, an aromatic hydrocarbon group, a heterocyclic group, an aryloxy group, a heteroaryloxy group, a silyl group, and a cyano group, provided that at least one of R1 to R4 and R8 to R11 is an amino group or an amino group-containing group, and X is oxygen, sulfur, selenium, tellurium, or a CR15R16 group.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. In order to improve the efficiency of light-emitting elements, elements using highly efficient materials such as phosphorescent materials and delayed fluorescent materials can be mentioned. Patent Document 1 describes the following compound A-1, and Patent Document 2 describes the following compound A-2.

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

[0004] [Patent Document 1] Korean Patent Publication No. 2012-070468 [Patent Document 2] International Publication No. 2017 / 017205 Summary of the Invention [Problem to be solved by the invention]

[0005] However, when compound A-1 described in Patent Document 1 is used in an organic light-emitting device, there is a problem with luminous efficiency, and when compound A-2 described in Patent Document 2 is used in an organic light-emitting device, there is a problem with driving durability. The present invention has been made to solve the above problems, and an object of the present invention is to provide an organic compound having high chemical stability and suitable for use as a material for an organic light-emitting device. Another object of the present invention is to provide an organic light-emitting device having excellent luminous efficiency and driving durability. [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 general formula [1], R1 to R4 are each a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted Phenyl Groups, substituted or unsubstituted Dibenzothiophenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted triazyl group R to R are independently selected from a group consisting of a silyl group and a silyl group; 11 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted Phenyl R5 to R7, R are independently selected from a group consisting of a silyl group and a silyl group. 12 ~R 14 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted Phenyl Groups, substituted or unsubstituted Dibenzothiophenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted triazyl group basis , Shi Lil Base The R6 and R7, and the R 12 and the above R 13 may be bonded to each other to form a ring structure. 11One of the groups is a substituted or unsubstituted amino group. The groups bonded to the nitrogen atoms of the substituted or unsubstituted amino groups may be bonded to each other to form a ring structure. X is oxygen, sulfur, selenium, tellurium, Cr 15 R 16 R represents one of the groups. 15 ~R 16 is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted Phenyl Groups, substituted or unsubstituted Dibenzothiophenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted triazyl group basis , Shi Lil Base Each of them is independently selected. [Effects of the Invention]

[0008] The organic compound according to the present invention has excellent chemical stability and light-emitting properties, and therefore, when used in an organic light-emitting device, it is possible to provide an organic light-emitting device having excellent light-emitting efficiency and driving durability. [Brief explanation of the drawings]

[0009] [Figure 1] FIG. 1 is a diagram showing the distribution of HOMO and LUMO electron orbitals. [Figure 2] FIG. 1 illustrates the planarity of a molecule. [Figure 3] FIG. 1 illustrates the planarity of a molecule. [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] 1 is a schematic diagram illustrating an example of a display device according to an embodiment of the present invention. [Figure 6] 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 7] 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 8] (a) A schematic diagram showing an example of a lighting device according to an embodiment of the present invention. (b) A schematic diagram showing an example of an automobile having a vehicle lamp according to an embodiment of the present invention. [Figure 9] (a) A schematic diagram showing an example of a wearable device according to an embodiment of the present invention. (b) A schematic diagram showing another example of a wearable device according to an embodiment of the present invention. [Figure 10] (a) A schematic diagram representing an example of an image forming apparatus according to an embodiment of the present invention. (b) A schematic diagram representing an example of an exposure light source of an image forming apparatus according to an embodiment of the present invention.

Embodiments for Carrying Out the Invention

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

[0011]

Chemical Formula

[0012] <R1 to R 14 > R1 to R 14 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a silyl group, and a cyano group. R6 and R7, R 12 and R 13 may be bonded to each other to form a ring structure. However, at least one of R1 to R4, R8 to R 11 is a substituted or unsubstituted amino group or a group having a substituted or unsubstituted amino group. The groups bonded to the nitrogen atom of the substituted or unsubstituted amino group may be bonded to each other to form a ring structure.

[0013] 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. The alkyl group is preferably an alkyl group having 1 to 10 carbon atoms.

[0015] Examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy, 2-ethyl-octyloxy, and benzyloxy groups. Preferred alkoxy groups have 1 to 10 carbon atoms.

[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, an N-piperidyl group, a carbazolyl group, and an acridyl group.

[0017] The amino group may have any of the following structures: In the following structural formulas, * indicates the bonding position.

[0018] [ka]

[0019] Among these, amino groups having any of the following structures are preferred: In the following structural formulas, * indicates the bonding position.

[0020] [ka]

[0021] Examples of aromatic hydrocarbon groups include, but are not limited to, phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, anthranyl, perylenyl, chrysenyl, and fluoranthenyl groups. Preferred aromatic hydrocarbon groups have 6 to 60 carbon atoms.

[0022] Examples of heterocyclic groups include, but are not limited to, pyridyl, pyrimidyl, pyrazyl, triazyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, carbazolyl, acridinyl, and phenanthrolyl groups. Preferred heterocyclic groups are those having 3 to 60 carbon atoms.

[0023] Examples of the aryloxy group include, but are not limited to, a phenoxy group and a naphthoxy group.

[0024] Examples of heteroaryloxy groups include, but are not limited to, furanyloxy groups and thienyloxy groups.

[0025] Examples of the silyl group include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0026] Examples of substituents that may be further possessed by the alkyl group, alkoxy group, amino group, aromatic hydrocarbon group, heterocyclic group, aryloxy group, and heteroaryloxy group include, but are not limited to, alkyl groups such as methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, and tertiary butyl group, aralkyl groups such as benzyl group, aromatic hydrocarbon groups such as phenyl group, biphenyl group, and naphthyl group, heterocyclic groups such as pyridyl group, pyrrolyl group, pyrazyl group, and triazyl group, amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, and ditolylamino group, alkoxy groups such as methoxy group, ethoxy group, and propoxy group, aryloxy groups such as phenoxy group, halogen atoms such as fluorine, chlorine, bromine, and iodine, and cyano group. In addition, groups bonded to nitrogen atoms of the amino groups that may be further possessed may be bonded to each other to form a ring structure.

[0027] R6 to R7, R 12 ~R 13 is preferably not a hydrogen atom. 11 At least one of R1 to R5 and R2 is preferably a substituted or unsubstituted amino group or a group having a substituted or unsubstituted amino group, and more preferably a substituted or unsubstituted amino group. 14 is preferably any one of a hydrogen atom, a substituted or unsubstituted alkyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrazyl group, a triazyl group, fluorine, and a cyano group.

[0028] <x> X is oxygen, sulfur, selenium, tellurium, Cr 15 R 16 Preferably, X is selected from oxygen and sulfur.

[0029] R 15 ~R 16 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryloxy group, a silyl group, and a cyano group.

[0030] R 15 ~R 16 Specific examples of the halogen atom, alkyl group, alkoxy group, amino group, aromatic hydrocarbon group, heterocyclic group, aryloxy group, heteroaryloxy group, and silyl group represented by the formula (I) include R1 to R2. 14 Examples of substituents that may be further introduced by the alkyl group, alkoxy group, and heteroaryloxy group include, but are not limited to, those described above. The alkyl group is preferably an alkyl group having 1 to 10 carbon atoms. The alkoxy group is preferably an alkoxy group having 1 to 10 carbon atoms. The aromatic hydrocarbon group is preferably an aromatic hydrocarbon group having 6 to 60 carbon atoms. The heterocyclic group is preferably a heterocyclic group having 3 to 60 carbon atoms. Specific examples of substituents that may be further introduced by the alkyl group, alkoxy group, amino group, aromatic hydrocarbon group, heterocyclic group, aryloxy group, and heteroaryloxy group include R1 to R2. 14 Examples of the above-described examples include, but are not limited to, those described above.

[0031] 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.

[0032] [ka]

[0033] Here, by appropriately changing the compounds shown in (a) to (c) above, the compound represented by the general formula [1] can be obtained. However, the synthesis method is not limited to these.

[0034] Next, the organic compound according to this embodiment has the following characteristics, and therefore, when used in an organic light-emitting device, it provides an organic light-emitting device with high light emission efficiency and excellent driving durability. Note that the basic skeleton in this embodiment is the R1 to R2 of the compound represented by general formula [1]. 14 are all hydrogen atoms, and X is CR 12 R 13 In the case of a group, further R 12 ~R 13 is a skeleton in which all atoms are hydrogen atoms. (1) As a basic skeleton, it has a structure in which an electron-withdrawing carbonyl group is bonded to a tetrahydroanthracene skeleton while forming a ring structure, and further has R1 to R4, R8 to R 11 At least one of the groups is an electron-donating amino group or a group having an electron-donating amino group, so that the energy gap between S1 and T1 is small. (2) The basic structure is a tetrahydroanthracene skeleton to which an electron-withdrawing carbonyl group is bonded in a ring structure, resulting in a deep HOMO (highest occupied molecular orbital). (3) The basic structure is a tetrahydroanthracene skeleton to which an electron-withdrawing carbonyl group is bonded in a ring structure, resulting in high planarity and excellent carrier transport properties.

[0035] The above features (1) to (3) will be explained below. (1) As a basic skeleton, it has a structure in which an electron-withdrawing carbonyl group is bonded to a tetrahydroanthracene skeleton while forming a ring structure, and further has R1 to R4, R8 to R 11 At least one of the groups is an electron-donating amino group or a group having an electron-donating amino group, so that the energy gap between S1 and T1 is small.

[0036] In creating the organic compound represented by the general formula [1], the present inventors focused on the electron distribution of the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) of the compound.

[0037] 1, in the exemplary compounds B-1, B-2, and D-1 of this embodiment, the portion occupying the HOMO electron orbital distribution and the portion occupying the LUMO electron orbital distribution are separated. In other words, it can be seen that there are few portions occupying both the HOMO and the LUMO.

[0038] This results in a smaller overlap integral and a smaller energy difference between the excited singlet state (S1) and the excited triplet state (T1). Specifically, the energy gaps between S1 and T1 of B-1, B-2, and D-1 are small, at 0.14 eV, 0.21 eV, and 0.22 eV, respectively. On the other hand, the energy gap between S1 and T1 of Comparative Compound 1 is large, at 0.47 eV.

[0039] The above-mentioned feature is that the compound has a structure in which an electron-withdrawing carbonyl group is bonded to a tetrahydroanthracene skeleton as a basic skeleton while forming a ring structure, and further has R1 to R4, R8 to R 11 At least one of the effects is due to the presence of an electron-donating amino group or a group having an electron-donating amino group. On the other hand, in the case of a structure without an amino group, such as comparative compound 1, the overlap between the part occupying the HOMO electron orbital distribution and the part occupying the LUMO electron orbital distribution is large. This results in a large energy gap between S1 and T1. Note that comparative compound 1 is compound A-1 described in Patent Document 1.

[0040] The above calculation results were visualized using molecular orbital calculations. The calculation method used for molecular orbital calculations was the density functional theory (DFT), which is currently widely used. The functional used 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.)

[0041] As described above, the compound of this embodiment is characterized by a small energy difference between S1 and T1. Therefore, by using the compound of this embodiment in the light-emitting layer of an organic light-emitting device, a highly efficient light-emitting device can be provided. This is because the small energy difference between S1 and T1 allows excitons generated in a 1:3 ratio of singlet excitons and triplet excitons to be used in delayed fluorescence emission, in which triplet excitons that are normally thermally deactivated emit light from the singlet excited state. A small difference between S1 and T1 is advantageous for converting triplet excitons to the singlet excited state, since this reduces the energy barrier. Therefore, the compound of this embodiment, which has a small energy difference between S1 and T1, facilitates the conversion of triplet excitons to the singlet excited state, thereby providing a highly efficient light-emitting device.

[0042] (2) The basic structure is a tetrahydroanthracene skeleton to which an electron-withdrawing carbonyl group is bonded in a ring structure, resulting in a deep HOMO (highest occupied molecular orbital).

[0043] The compound of this embodiment has a fused polycyclic structure in which an electron-withdrawing carbonyl group is bonded to a tetrahydroanthracene skeleton to form a ring structure. By having such a fused polycyclic structure as an electron-withdrawing moiety, the HOMO and LUMO levels become deeper (farther from the vacuum level).

[0044] Here, a deep HOMO means that the material is resistant to oxidation, i.e., has high oxidation stability. Therefore, the material itself is resistant to deterioration by oxygen and moisture. In general, organic light-emitting devices are devices that are susceptible to deterioration by oxygen and moisture, and therefore, materials used for organic light-emitting devices are preferably highly oxidatively stable.

[0045] Table 1 compares the HOMO energies of compounds B-1 and B-2 of this embodiment with those of comparative compound 2. Comparative compound 2 is compound A-2 described in Patent Document 2. As shown in Table 1, the HOMOs of the compounds of this embodiment are deep (far from the vacuum level) at -6.19 eV and -5.36 eV. Therefore, these materials are considered to have high oxidation stability. This is thought to be due to the structure in which electron-withdrawing carbonyl groups are bonded while forming a ring structure. On the other hand, the HOMO of comparative compound 2 is shallow at -4.10 eV, making it a material with low oxidation stability. Comparative compound 2 also has electron-withdrawing carbonyl groups, but does not form a ring structure, which is thought to be why its HOMO energy is shallow.

[0046] As described above, by using the compound of this embodiment, which has excellent oxidation stability, in an organic light-emitting element, it is possible to exhibit better driving durability.

[0047] [Table 1]

[0048] (3) The basic structure is a tetrahydroanthracene skeleton to which an electron-withdrawing carbonyl group is bonded in a ring structure, resulting in high planarity and excellent carrier transport properties.

[0049] The compound of this embodiment has a fused polycyclic structure in which five six-membered rings are fused in a plane, with electron-withdrawing carbonyl groups bonded to a tetrahydroanthracene skeleton to form a ring structure. Therefore, the moieties of this fused polycyclic structure tend to overlap with each other.

[0050] As described in the above feature (1), the LUMO distribution of the compound of this embodiment is localized in this fused polycyclic structure (a structure in which an electron-withdrawing carbonyl group is bonded to a tetrahydroanthracene skeleton while forming a ring structure).

[0051] Generally, carrier transport in organic light-emitting devices involves hole carriers being transported by hopping conduction via the HOMO of the organic material, and electron carriers being transported by hopping conduction via the LUMO. In the compound of this embodiment, as shown in FIG. 1, the LUMO moiety is in a highly planar fused polycyclic structure, which strengthens the overlap between the LUMOs and facilitates hopping conduction of electron carriers via the LUMO. In other words, the compound of this embodiment is a material with excellent carrier transport ability, and when used in an organic light-emitting device, it enables low-voltage operation, reduces unnecessary carrier traps, and reduces charge concentration, thereby providing an organic light-emitting device with excellent durability.

[0052] Here, in FIG. 2, the planarity of the carbonyl group and the benzene ring bonded thereto between compound B-3 of this embodiment and comparative compound 2 is compared (the dotted line in FIG. 2). As shown in FIG. 2, the planarity of the fused polycyclic structure in which the LUMO of the compound of this embodiment is localized is high, and the dihedral angle is small at 0.1°. Therefore, it can be said that this material has excellent carrier transport ability. On the other hand, the dihedral angle of comparative compound 2 is large at 30.4°, and therefore has low planarity. As a result, the intermolecular distance at the LUMO site increases, resulting in a decrease in carrier transport ability.

[0053] As described above, by using the compound of this embodiment, which has excellent carrier transport ability, in an organic light-emitting element, it is possible to exhibit better driving durability.

[0054] Furthermore, it is preferable that the organic compound satisfies the following conditions (4) to (7).

[0055] (4) R6 to R7 and R 12 ~R 13 is not a hydrogen atom.

[0056] This is because, when this condition is satisfied, the planarity of the fused polycyclic structure containing the electron-withdrawing carbonyl group is improved, which makes it easier for the moieties of the fused polycyclic structure to overlap with each other, thereby improving the carrier transport ability of the compound of this embodiment, as described in the above feature (3).

[0057] Here, in Figure 3, the planarity of the benzene ring in the tetrahydroanthracene skeleton is compared between Compounds B-1 and B-3 of this embodiment (the dotted line in Figure 3). As shown in Figure 3, the dihedral angles of Compound B-1 and Compound B-3 are 0.7° and 36.1°, respectively. This indicates that Compound B-1 has higher planarity than Compound B-3, and is therefore a material with superior carrier transport ability.

[0058] (5)R8 to R 11 At least one of the groups is an amino group or a group having an amino group.

[0059] This is because, when this condition is satisfied, the distance between the electron-withdrawing carbonyl group and the electron-donating amino group in the basic skeleton increases, improving the separation of the HOMO and LUMO electron orbital distributions described in the above characteristic (1).

[0060] This reduces the energy gap between S1 and T1. Specifically, as shown in FIG. 1, the energy gaps between S1 and T1 of Exemplary Compound B-1 and Exemplary Compound B-2 are 0.14 eV and 0.21 eV, respectively. 11 It can be seen that Example Compound B-1 having an amino group at any one of R1 to R4 has a smaller energy gap between S1 and T1 than Example Compound B-2 having an amino group at any one of R1 to R4. This is advantageous for reverse intersystem crossing, increases delayed fluorescence emission, and provides a highly efficient light-emitting device.

[0061] Furthermore, when this condition is satisfied, the HOMO energy becomes deeper (farther from the vacuum level). Specifically, as shown in Table 1, the HOMO energies of Exemplary Compound B-1 and Exemplary Compound B-2 are −6.19 eV and −5.36 eV, respectively. From this, R8 to R 11 It can be seen that Example Compound B-1 having an amino group at any one of R1 to R4 has a deeper HOMO energy than Example Compound B-2 having an amino group at any one of R1 to R4. Therefore, as described in the above characteristic (2), the material has high oxidation stability, and therefore a device having excellent driving durability can be provided.

[0062] (6)R8 to R 11 At least one of the groups is an amino group having any of the following structures (* indicates the bonding position):

[0063] [ka]

[0064] This is because, when this condition is satisfied, the molecular planarity of the amino group where the HOMO is localized is improved, and as explained in the above characteristic (3), the hole transport ability by hopping conduction via the HOMO is improved. As a result, the material has excellent carrier transport ability for both holes and electrons, which is advantageous for the driving voltage and driving durability of organic light-emitting devices.

[0065] R8 to R 11 It is more preferable that at least one of the groups is an amino group having any of the following structures (* indicates the bonding position):

[0066] [ka]

[0067] (7) X is selected from oxygen and sulfur.

[0068] This is because, when this condition is satisfied, the energy gap between S1 and T1 becomes small, which is advantageous for reverse intersystem crossing, as explained in the above characteristic (1), and increases delayed fluorescence emission, making it possible to provide a highly efficient light-emitting element.

[0069] Specifically, as shown in Figure 1, the energy gaps S1 and T1 of Example Compound B-1 and Example Compound D-1 are 0.14 eV and 0.22 eV, respectively. This shows that Example Compound B-1, in which X is oxygen, has a smaller energy gap S1 and T1 than Example Compound D-1, in which X is C(Me)2. As a result, this is advantageous for reverse intersystem crossing, which increases delayed fluorescence emission and is advantageous for improving the efficiency of organic light-emitting devices.

[0070] Furthermore, the compound of this embodiment is preferably used in the light-emitting layer of an organic light-emitting device, and in that case, it has the following characteristics. (8) By mixing the compound of this embodiment with a host material in the light-emitting layer, the compound of this embodiment is more likely to cause exciton recombination, providing a highly efficient light-emitting device. (9) By mixing the compound of this embodiment with a host material in the light-emitting layer and further including a light-emitting material, a light-emitting device with high efficiency and high color purity can be provided. (10) When the light-emitting material is a hydrocarbon compound, a light-emitting device with high efficiency and excellent durability can be provided.

[0071] The above features (8) to (10) will be explained below. (8) By mixing the compound of this embodiment with a host material in the light-emitting layer, the compound of this embodiment is more likely to cause exciton recombination, providing a highly efficient light-emitting device.

[0072] The compound of this embodiment has an electron-withdrawing carbonyl group and an electron-donating amino group. Therefore, when the compound is mixed with a host material in the light-emitting layer of an organic light-emitting device, the LUMO of the compound of this embodiment is at a lower level (farther from the vacuum level) than the host material, and the HOMO of the compound of this embodiment is at a higher level (closer to the vacuum level) than the host material.

[0073] Therefore, electrons and holes supplied from the transport layer are trapped in the emissive layer by the compound of this embodiment, and exciton recombination occurs. As described in the above feature (1), the compound of this embodiment has a small energy difference between S1 and T1, which allows for efficient delayed fluorescence emission in the emissive layer and allows for a greater number of triplet excitons to be utilized for emission. This effect is particularly pronounced when the host material is a hydrocarbon compound, as the energy difference between the HOMO and LUMO of the host and the compound of this embodiment becomes larger, making it easier to trap electrons and holes. A hydrocarbon compound is a compound composed only of carbon and hydrogen.

[0074] (9) By mixing the compound of this embodiment with a host material in the light-emitting layer and further including a light-emitting material, a light-emitting device with high efficiency and high color purity can be provided.

[0075] Light-emitting devices with even higher efficiency and color purity can be provided by mixing the compound of this embodiment with a host material in the light-emitting layer and further doping it with a light-emitting material with a high luminescence quantum yield or a light-emitting material with a spectrum suitable for achieving high color purity. In this case, the compound of this embodiment must be present in the light-emitting layer at a concentration sufficient to preferentially trap electrons and holes, in order to facilitate exciton recombination. This concentration is preferably 0.01% by mass to 20% by mass, and more preferably 1% by mass to 15% by mass. On the other hand, a lower doping concentration of the light-emitting material is preferable because it is less susceptible to concentration quenching and changes in the emission spectrum due to molecular interactions. Therefore, it is preferable to dope the light-emitting layer with a light-emitting material other than the compound of this embodiment. The doping concentration of the light-emitting material is preferably 0.1% by mass to 45% by mass, and more preferably 1% by mass to 30% by mass. These features make it possible to provide light-emitting devices with high efficiency and high color purity.

[0076] (10) When the light-emitting material is a hydrocarbon compound, a light-emitting device with high efficiency and excellent durability can be provided.

[0077] Since the compound of this embodiment has a carbonyl group with strong electron-withdrawing properties, the doped light-emitting material described in the above feature (9) is preferably a light-emitting material that does not have an amino group, which is an electron-donating group, and is preferably a compound made of a hydrocarbon. The reason for this is that a light-emitting material having an amino group may interact with the carbonyl group of the compound of this embodiment in the light-emitting layer, resulting in a decrease in light-emitting efficiency due to exciplex formation, or a change in the light-emitting spectrum of the light-emitting material, which may deteriorate the color purity of the light-emitting element.

[0078] Furthermore, light-emitting materials with amino groups have a low ionization potential, making them susceptible to oxidation and resulting in poor device durability. Therefore, hydrocarbon compounds are preferred as light-emitting materials, and fused polycyclic compounds with five-membered rings are even more preferred. This is because their higher ionization potential makes them less susceptible to oxidation. Hydrocarbon compounds are compounds composed only of carbon and hydrogen.

[0079] As described above, by mixing the compound of this embodiment with a host material in the light-emitting layer, an organic light-emitting device with high light emission efficiency can be obtained. In this case, the light-emitting material may be the compound of this embodiment, or an additional light-emitting material may be mixed and the compound of this embodiment may function as an assist material. By using a light-emitting material with good color purity, an organic light-emitting device with high efficiency and high color purity can be obtained. Furthermore, when the host material is a hydrocarbon compound, the compound of this embodiment tends to trap electrons and holes, which is highly effective in increasing efficiency, and is therefore preferred.

[0080] Specific examples of organic compounds according to this embodiment are shown below (B-16, 22, 23, 24, C-13,14,15,18,19,20, D-10,14, 27,28, E-5, 6, 7, and 8 are reference examples. However, the present invention is not limited to these.

[0081] [ka]

[0082] [ka]

[0083] [ka]

[0084] [ka]

[0085] Compounds in which X is oxygen belong to Group B. When X is oxygen, the fused polycyclic structure of the electron-withdrawing moiety is less susceptible to chemical reactions such as oxidation, providing chemically stable compounds.

[0086] Compounds belonging to Group C are compounds in which X is sulfur. When X is sulfur, the fused polycyclic structure of the electron-withdrawing moiety has an abundance of unshared electron pairs, resulting in a compound with superior carrier transport ability.

[0087] Those belonging to group D are those where X is CR 15 R 16 The compound is X is CR 15 R 16 This results in excellent reduction of molecular association, making the compound less susceptible to concentration quenching.

[0088] Compounds belonging to group E are those in which X is selenium or tellurium. Selenium and tellurium have d orbitals and are metallic elements, so compounds belonging to group E have high carrier mobility.

[0089] <Organic light-emitting element> Next, the organic light-emitting device of this embodiment will be described.

[0090] The organic light-emitting element 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 element of this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers, as long as it has a light-emitting layer. 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.

[0091] In the organic light-emitting device of this embodiment, the organic compound according to this embodiment is contained in at least one of the organic compound layers. Specifically, the organic compound according to this embodiment is contained in any of the above-mentioned light-emitting layer, hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole / exciton blocking layer, electron transport layer, electron injection layer, etc. The organic compound according to this embodiment is preferably contained in the light-emitting layer. The light-emitting layer can emit green or red light, but the emitted color is not limited thereto.

[0092] 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 with a mass ratio smaller than that of the host among the compounds constituting the light-emitting layer, and is a compound that is mainly responsible for light emission. Furthermore, the assist material is a compound with a mass ratio smaller than that of the host among the compounds constituting the light-emitting layer, and assists the light emission of the guest.

[0093] 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 0.01% by mass to 20% by mass, and more preferably 1% by mass to 15% by mass, based on the total mass of the light-emitting layer. 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 0.1% by mass to 45% by mass, and more preferably 1% by mass to 30% by mass, based on the total mass of the light-emitting layer.

[0094] Furthermore, when the organic compound according to this embodiment is used as a guest in the light-emitting layer, it is preferable to use a material having a higher LUMO than the organic compound according to this embodiment (a material having a LUMO closer to the vacuum level) as the host. This is because the organic compound according to this embodiment has a low LUMO, and by using a material having a higher LUMO than the organic compound according to this embodiment as the host, the organic compound according to this embodiment can receive more electrons supplied to the host in the light-emitting layer.

[0095] Furthermore, when the organic compound according to this embodiment is used as an assist material in the light-emitting layer, it is preferable to use a material with a higher LUMO than the organic compound according to this embodiment (a material with a LUMO closer to the vacuum level) as a guest. This is because the organic compound according to this embodiment has a low LUMO. Therefore, by using a material with a higher LUMO than the organic compound according to this embodiment as the guest light-emitting material, the organic compound according to this embodiment receives more electrons supplied to the host of the light-emitting layer, and the assist material is responsible for exciton recombination. As a result, energy can be efficiently transferred to the guest light-emitting material.

[0096] The present inventors have conducted various studies and found that when the organic compound according to this embodiment is used as a host, guest, or assist material in the light-emitting layer, particularly as a guest in the light-emitting layer, a device exhibiting high-efficiency, high-brightness light output and extremely high durability can be obtained. Furthermore, when the organic compound is used as an assist material in the light-emitting layer, a device exhibiting high-efficiency, high-brightness light output and extremely high durability can be obtained. The light-emitting layer may be a single layer or multiple layers, and may contain multiple light-emitting materials. A multiple layer may mean a stack of a light-emitting layer and another light-emitting layer, or a stack of multiple light-emitting layers with an intermediate layer stacked between them. Tandem or stacked elements are also possible. In these cases, the emitted light color of the organic light-emitting element is not limited to a single color. More specifically, it may be white or a neutral color. Furthermore, the film formation method is performed by vapor deposition or coating. Details of this will be explained in detail in the examples below.

[0097] The organic compound according to this embodiment can be used as a constituent material of an organic compound layer other than the light-emitting layer that constitutes the organic light-emitting device of this embodiment, specifically, 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.

[0098] In addition to the organic compound according to this embodiment, conventionally known low-molecular-weight and high-molecular-weight hole-injecting or hole-transporting compounds, host compounds, light-emitting compounds, electron-injecting or electron-transporting compounds, etc. may also be used together as needed. Examples of these compounds are listed below.

[0099] 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.

[0100] [ka]

[0101] Among the hole transport materials listed above, HT16 to HT18 can reduce the driving voltage when used in a layer in contact with the anode. HT16 is widely used in organic light-emitting devices. HT2, HT3, HT4, HT5, HT6, HT10, and HT12 may be used in an organic compound layer adjacent to HT16. Furthermore, multiple materials may be used in one organic compound layer.

[0102] Examples of light-emitting materials that are primarily involved in light-emitting function include organic compounds represented by general formula [1], 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 listed below, but of course, they are not limited to these.

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[0105] The luminescent material is preferably a hydrocarbon compound, as this prevents a decrease in luminous efficiency due to exciplex formation and a deterioration in color purity due to changes in the luminescent spectrum of the luminescent material. Hydrocarbon compounds are compounds composed only of carbon and hydrogen, and examples of these include BD7, BD8, GD5 to GD9, and RD1. The luminescent material is even more preferably a fused polycyclic ring containing a five-membered ring, as this has a high ionization potential, making it less susceptible to oxidation and providing an element with a long, durable lifespan. Examples of these include BD7, BD8, GD5 to GD9, and RD1.

[0106] Examples of the light-emitting layer host or light-emitting assist material contained in the light-emitting layer include aromatic hydrocarbon compounds or derivatives thereof, as well as carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organoaluminum complexes such as tris(8-quinolinolato)aluminum, and organic beryllium complexes. Specific examples of compounds used as the light-emitting layer host or light-emitting assist material contained in the light-emitting layer are shown below, but the present invention is not limited to these.

[0107] [ka]

[0108] When the host material is a hydrocarbon compound, the compound of this embodiment is more likely to trap electrons and holes, which is preferable because it has a significant effect of improving efficiency. Hydrocarbon compounds are compounds composed only of carbon and hydrogen, and correspond to EM1 to EM12 and EM16 to EM27.

[0109] The electron transport material can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light-emitting layer, and is selected taking into consideration the balance with the hole mobility of the hole transport material. Examples of materials having electron transport properties include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, and fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron transport materials are also suitable for use in hole-blocking layers. Specific examples of compounds used as electron transport materials are shown below, but of course, the present invention is not limited to these.

[0110] [ka]

[0111] The electron injection material can be selected from those that allow easy electron injection from the cathode, taking into consideration the balance with hole injection properties, etc. Organic compounds include n-type dopants and reducing dopants. Examples include compounds containing alkali metals such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fulvalene derivatives, and acridine derivatives.

[0112] <Configuration of organic light-emitting element> The organic light-emitting element is provided by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode on a substrate. A protective layer, a color filter, a microlens, etc. may be provided on the second electrode. When a color filter is provided, a planarizing layer may be provided between the color filter and the protective layer. The planarizing layer may be made of an acrylic resin, etc. The same applies when a planarizing layer is provided between the color filter and the microlens.

[0113] [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.

[0114] [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.

[0115] 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.

[0116] 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.

[0117] 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.

[0118] 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.

[0119] 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.

[0120] [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.

[0121] The organic compound layers (hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) constituting the organic light emitting device according to one embodiment of the present invention are formed by the method shown below.

[0122] The organic compound layer constituting the organic light-emitting device according to one embodiment of the present invention can be formed by dry processes such as vacuum deposition, ionization deposition, sputtering, plasma, etc. Alternatively to the 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 (for example, spin coating, dipping, casting, LB method, inkjet method, etc.).

[0123] Here, when a layer is formed by a vacuum deposition method or a solution coating method, crystallization is unlikely to occur and the layer has excellent stability over time. When a film is formed by a coating method, the film can be formed by combining with an appropriate binder resin.

[0124] Examples of the binder resin include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0125] These binder resins may be used singly or in combination as homopolymers or copolymers, and may further contain known additives such as plasticizers, antioxidants, and ultraviolet absorbers, if necessary.

[0126] [Protective layer] A protective layer may be provided on the second electrode. For example, by adhering glass with a moisture absorbent on the second electrode, the infiltration of water and other contaminants into the organic compound layer can be reduced, thereby reducing the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the second electrode to reduce the infiltration of water and other contaminants into the organic compound layer. For example, after forming the second electrode, the second electrode may be transferred to another chamber without breaking the vacuum, and a 2 μm-thick silicon nitride film may be formed by CVD to serve as a protective layer. A protective layer may be provided using atomic layer deposition (ALD) after the CVD film formation. The material of the film formed by ALD is not limited, and may be silicon nitride, silicon oxide, aluminum oxide, or the like. Silicon nitride may be further formed on the film formed by ALD by CVD. The film formed by ALD may have a thickness smaller than that of the film formed by CVD. Specifically, the thickness may be 50% or less, or even 10% or less.

[0127] [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.

[0128] [Planarization layer] A planarization layer may be provided between the color filter and the protective layer. The planarization layer is provided for the purpose of reducing the unevenness of the underlying layer. It may also be called a material resin layer without limiting its purpose. The planarization layer may be composed of an organic compound, and may be either a low molecular weight or a high molecular weight, but a high molecular weight is preferred.

[0129] The planarizing layer may be provided above or below the color filter, and may be made of the same or different materials, such as polyvinyl carbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicone resin, and urea resin.

[0130] [Microlens] The organic light-emitting element or 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 intended to increase the amount of light extracted from the organic light-emitting element or organic light-emitting device or 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 vertex of the microlens is the point of contact between this tangent and the hemisphere. 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 vertex of the microlens is the point of contact between this tangent and the semicircle.

[0131] 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.

[0132] [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.

[0133] [Pixel circuit] An organic light-emitting device having an organic light-emitting element may have a pixel circuit connected to the organic light-emitting element. The pixel circuit may be an active matrix type that controls the emission of the first light-emitting element and the second light-emitting element independently. The active matrix type circuit may be voltage-programmed or current-programmed. The drive circuit has a pixel circuit for each pixel. The pixel circuit may have a light-emitting element, a transistor that controls the emission brightness of the light-emitting element, a transistor that controls the emission timing, a capacitor that holds the gate voltage of the transistor that controls the emission brightness, and a transistor for connecting to GND without going through the light-emitting element.

[0134] The magnitude of the drive current may be determined according to the size of the light-emitting area. Specifically, when the first light-emitting element and the second light-emitting element are caused to emit light with the same luminance, the current value passed through the first light-emitting element may be smaller than the current value passed through the second light-emitting element. This is because the required current may be small due to the small light-emitting area.

[0135] [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.

[0136] A pixel emits light from an area called a pixel aperture. This area is the same as the first area. The pixel aperture may be 15 μm or less, or 5 μm or more. More specifically, it may be 11 μm, 9.5 μm, 7.4 μm, 6.4 μm, etc. The distance between subpixels may be 10 μm or less, more specifically, it may be 8 μm, 7.4 μm, or 6.4 μm.

[0137] 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.

[0138] <Uses of the organic light-emitting device according to this embodiment> 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.

[0139] 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.

[0140] 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.

[0141] Next, a 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).

[0142] 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 the light emitted from the sub-pixels. The emitted light 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 edge of the first electrode 2, an organic compound layer 4 covering the first electrode 2 and the insulating layer 3, a transparent electrode serving as a second electrode 5, a protective layer 6, and a color filter 7.

[0143] A transistor and a capacitor element may be disposed below or inside the interlayer insulating layer 1. The transistor and the first electrode 2 may be electrically connected via a contact hole or the like (not shown). 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 contacts the organic compound layer 4 and becomes a light-emitting region.

[0144] 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 . The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode. 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.

[0145] The color filters 7 are divided into 7R, 7G, and 7B depending on their colors. The color filters 7 may be formed on a planarization film (not shown). A resin protective layer (not shown) may be provided on the color filters 7. The color filters 7 may be formed on a protective layer 6. Alternatively, the color filters 7 may be provided on an opposing substrate such as a glass substrate and then bonded thereto.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] In the display device 100 of FIG. 4(b), transistors are used as switching elements, but other switching elements may be used instead.

[0150] 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 an insulating surface of a substrate. Examples of active layers include single-crystal silicon, amorphous silicon, microcrystalline silicon, and other non-single-crystal silicon, as well as non-single-crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Thin-film transistors are also called TFT elements.

[0151] 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.

[0152] 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. Note that the switching element according to this embodiment is not limited to a TFT, and may 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 in 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.

[0153] 5 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.

[0154] 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.

[0155] 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.

[0156] 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.

[0157] 6(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.

[0158] 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.

[0159] 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.

[0160] FIG. 6(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 unlock the device, etc. 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.

[0161] FIG. 7 is a schematic diagram illustrating an example of a display device according to this embodiment. FIG. 7(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 includes 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. 7(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.

[0162] FIG. 7(b) is a schematic diagram illustrating another example of a display device according to this embodiment. The display device 1310 in FIG. 7(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.

[0163] FIG. 8(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 for illumination purposes, etc., 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 device. If necessary, a cover may be provided on the outermost surface.

[0164] 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.

[0165] 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.

[0166] 8(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.

[0167] 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.

[0168] 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.

[0169] 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.

[0170] An application example of the display device of each of the above-described embodiments will be described with reference to Fig. 9. 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.

[0171] Fig. 9(a) is a schematic diagram showing an example of a wearable device according to an embodiment of the present invention. Using Fig. 9(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.

[0172] 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.

[0173] FIG. 9(b) is a schematic diagram showing another example of a wearable device according to an embodiment of the present invention. Using FIG. 9(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. 9(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 also controls the operation of the imaging device and the display device.

[0174] 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.

[0175] 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.

[0176] 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.

[0177] Note that AI may be used to determine the first field of view area and areas 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 an 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 an external device, it is transmitted to the display device via communication.

[0178] 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.

[0179] FIG. 10(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. The exposure light source 28 includes the organic light-emitting element according to this embodiment. The developing unit 31 includes toner and the like. The charging unit 30 charges the photoconductor 27. The transfer unit 32 transfers the developed image to a recording medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fixing unit 35 fixes the image formed on the recording medium 34.

[0180] 10(b) and 10(c) are diagrams showing an exposure light source 28 and are schematic diagrams illustrating a state in which multiple light-emitting units 36 are arranged on a long substrate. Arrow 37 indicates the direction parallel to the axis of the photoconductor, which represents the column direction in which the organic light-emitting elements 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. 10(b) shows a configuration in which the light-emitting units 36 are arranged along the long axis direction of the photoconductor 27. FIG. 10(c) shows a different configuration from FIG. 10(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. In the first column, multiple light-emitting units 36 are arranged at intervals. In the second column, light-emitting units 36 are located at positions corresponding to the intervals between the light-emitting units 36 in the first column. In other words, multiple light-emitting units 36 are also arranged at intervals in the row direction. The arrangement in FIG. 10(c) can also be described as a grid arrangement, a houndstooth arrangement, or a checkerboard pattern.

[0181] 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]

[0182] The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

[0183] [Example 1 (Synthesis of Exemplary Compound B-1)] Exemplary compound B-1 was synthesized according to the following scheme.

[0184] [ka]

[0185] (1) Synthesis of compound m-3 The following reagents and solvents were placed in a 100 ml recovery flask. Compound m-1: 1.8g (5.4mmol) Compound m-2: 0.7g (5.7mmol) Potassium carbonate: 1.1g (8.2mmol) DMF: 20 ml The reaction solution was then heated and stirred at 100°C for 7 hours under a nitrogen stream. After the reaction was completed, 100 ml of water was added and the mixture was filtered. The resulting solid was purified by silica gel column chromatography (toluene:ethyl acetate mixture) to obtain 1.9 g of m-3 (yield: 79%).

[0186] (2) Synthesis of compound m-4 The following reagents and solvents were placed in a 300 ml recovery flask. Compound m-3: 1.8g (4.2mmol) 6M sodium hydroxide solution: 90ml Ethanol: 90ml The reaction solution was then heated under reflux and stirred for 7 hours under a nitrogen stream. After the reaction was completed, concentrated hydrochloric acid was slowly added dropwise under a nitrogen stream at 0°C to create an acidic condition, and the precipitated solid was filtered. The resulting solid was dispersed and washed with 100 ml of water for 1 hour, and then filtered to obtain 1.7 g of m-4 (yield: 93%).

[0187] (3) Synthesis of compound m-5 The following reagents and solvents were placed in a 100 ml recovery flask. Compound m-4: 1.7g (3.8mmol) Sulfuric acid: 20ml Next, the reaction solution was stirred at 80°C for 7 hours under a nitrogen stream. After that, it was cooled to room temperature, poured into ice water, and filtered. The obtained solid was dispersed and washed with 100 ml of water for 1 hour, and then filtered to obtain a solid. The obtained solid was purified by silica gel column chromatography (chlorobenzene:ethyl acetate mixture) to obtain 1.3 g of m-5 (yield: 83%).

[0188] (4) Synthesis of Compound B-1 The following reagents and solvents were placed in a 200 ml recovery flask. Compound m-5: 1.3g (3.0mmol) Compound m-6: 0.6g (3.6mmol) Sodium tert-butyloxide: 0.86 g (9.0 mmol) Pd(dba)2: 170mg xphos: 430 mg Orthoxylene: 65ml The reaction solution was then heated and stirred at 140°C for 5 hours under a nitrogen stream. After the reaction was completed, the mixture was filtered through Celite and concentrated to dryness. The resulting solid was purified by silica gel column chromatography (toluene:ethyl acetate mixture) to obtain 0.9 g of B-1 (yield: 58%).

[0189] Exemplary Compound B-1 was subjected to mass spectrometry using MALDI-TOF-MS (Autoflex LRF, manufactured by Bruker). [MALDI-TOF-MS] Measured value: m / z=519 Calculated value: C 37 H 29 NO2=519

[0190] [Examples 2 to 6 (Synthesis of Exemplary Compounds)] As shown in Table 2, the exemplary compounds shown in Examples 2 to 6 were synthesized in the same manner as in Example 1, except that raw material m-1 in Example 1 was replaced with raw material 1, raw material m-2 with raw material 2, and raw material m-6 with raw material 3. The actual measured values ​​(m / z) of the mass spectrometry results measured in the same manner as in Example 1 are also shown.

[0191] [Table 2]

[0192] [Example 7 (Synthesis of Exemplary Compound D-7)] Exemplary compound D-7 was synthesized according to the following scheme.

[0193] [ka]

[0194] (1) Synthesis of compound m-9 The following reagents and solvents were placed in a 2000 ml recovery flask. Compound m-7: 20.0g (84.6mmol) Compound m-8: 21.1g (93.1mmol) Methylene chloride: 1000 ml Next, the reaction solution was stirred at 0°C for 1 hour under a nitrogen stream, and 16.9 g (126.9 mmol) of aluminum chloride was slowly added thereto. The temperature was then slowly raised to room temperature, and stirring was continued at room temperature for 8 hours. After completion of the reaction, the reaction solution was slowly poured into ice water, and an extraction operation was performed. The organic layer was concentrated to dryness, and the resulting solid was purified by silica gel column chromatography (toluene:ethyl acetate mixture), yielding 17.6 g (yield: 45%) of compound m-9.

[0195] (2) Synthesis of compound m-10 The following reagents and solvents were placed in a 500 ml recovery flask. Compound m-9: 16.0g (34.5mmol) Ethanol: 320ml Next, the reaction solution was stirred at 0°C for 1 hour under a nitrogen stream, and 1.5 g of sodium borohydride was slowly added thereto. The temperature was then slowly raised to room temperature, and stirring was continued at room temperature for 8 hours. After the reaction was completed, dilute hydrochloric acid was added at 0°C to neutralize the solution. An extraction operation was performed using methylene chloride, and the organic layer was concentrated to dryness. The resulting solid was purified by silica gel column chromatography (toluene:ethyl acetate mixture), yielding 12.9 g of m-10 (yield: 80%).

[0196] (3) Synthesis of compound m-11 The following reagents and solvents were placed in a 200 ml recovery flask. Compound m-10: 12.0g (25.8mmol) Methanol: 360 ml Sulfuric acid: 3.6ml Next, the reaction solution was heated and stirred at 70°C for 5 hours under a nitrogen stream. After the reaction was completed, the reaction solution was slowly poured into ice water, and methylene chloride was added to perform an extraction operation. The organic layer was concentrated to dryness, and the resulting solid was purified by silica gel column chromatography (toluene:ethyl acetate mixture) to obtain 8.4 g of m-11 (yield: 68%).

[0197] (4) Synthesis of compound m-12 The following reagents and solvents were placed in a 1000 ml recovery flask. Compound m-11: 8.0g (16.7mmol) Tetrahydrofuran: 160 ml Next, the reaction solution was stirred at -10°C for 1 hour under a nitrogen stream, and 27.8 ml of methylmagnesium chloride (3.0 M tetrahydrofuran solution) was slowly added thereto and stirred for 1 hour. The temperature was then slowly raised to room temperature and the mixture was stirred at room temperature for 3 hours. After the reaction was completed, a saturated aqueous ammonium chloride solution was added at 0°C. Methylene chloride was further added and an extraction operation was performed. The organic layer was concentrated to dryness, and the resulting solid was purified by silica gel column chromatography (toluene:ethyl acetate mixture) to obtain 6.8 g of m-12 (yield: 85%).

[0198] (5) Synthesis of compound m-13 The following reagents and solvents were placed in a 200 ml recovery flask. Compound m-12: 6.0g (12.5mmol) Methylene chloride: 60 ml Next, the reaction solution was stirred at -10°C for 1 hour under a nitrogen stream, and a solution consisting of 4.7 g of boron tribromide and 30 ml of methylene chloride was slowly added thereto and stirred for 1 hour. The temperature was then slowly raised to room temperature and the mixture was stirred at room temperature for 3 hours. After the reaction was completed, distilled water was added at 0°C. Further methylene chloride was added and an extraction operation was performed. The organic layer was concentrated to dryness, and the resulting solid was purified by silica gel column chromatography (toluene:ethyl acetate mixture) to obtain 3.9 g of m-13 (yield: 67%).

[0199] (6) Synthesis of compound m-14 The following reagents and solvents were placed in a 200 ml recovery flask. Compound m-13: 3.5g (7.6mmol) Methylene chloride: 35 ml Trifluoroacetic acid: 90 ml Manganese dioxide: 730mg Next, the reaction solution was heated and stirred at 40°C for 5 hours under a nitrogen stream. After the reaction was completed, the mixture was filtered and further filtered and washed with methylene chloride. Distilled water was added to the obtained filtrate, and a liquid separation operation was performed. The organic layer was concentrated to dryness, and the obtained solid was purified by silica gel column chromatography (toluene:ethyl acetate mixture) to obtain 2.6 g of m-14 (yield: 76%).

[0200] (7) Synthesis of Compound D-7 The following reagents and solvents were placed in a 200 ml recovery flask. Compound m-14: 1.5g (3.0mmol) Compound m-15: 0.6g (3.9mmol) Sodium tert-butyloxide: 0.94g (9.8mmol) Pd(dba)2: 190mg xphos: 470mg Orthoxylene: 75ml The reaction solution was then heated and stirred at 140°C for 5 hours under a nitrogen stream. After the reaction was completed, the mixture was filtered through Celite and concentrated to dryness. The resulting solid was purified by silica gel column chromatography (toluene:ethyl acetate mixture) to obtain 0.9 g of a yellow solid D-7 (yield: 48%).

[0201] Mass spectrometry was carried out on Exemplary Compound D-7 in the same manner as in Example 1. [MALDI-TOF-MS] Measured value: m / z=545 Calculated value: C 40 H 36 NO=545

[0202] [Examples 8 to 11 (Synthesis of Exemplary Compounds)] As shown in Table 3, the exemplary compounds shown in Examples 8 to 11 were synthesized in the same manner as in Example 7, except that raw material m-7 in Example 7 was replaced with raw material 1, raw material m-8 with raw material 2, and raw material m-15 with raw material 3. In Example 11, phenylmagnesium bromide was used instead of methylmagnesium chloride as the Grignard reagent in step (4). The actual measured values ​​(m / z) of the mass spectrometry results measured in the same manner as in Example 7 are also shown.

[0203] [Table 3]

[0204] Example 12 (Synthesis of Exemplary Compound C-17) Exemplary compound C-17 was synthesized according to the following scheme.

[0205] [ka]

[0206] (1) Synthesis of compound m-18 The following reagents and solvents were placed in a 500 ml recovery flask. Compound m-16: 5.0g (12.7mmol) Cesium carbonate: 5.0 g (10.1 mmol) DMF: 150ml Next, the reaction solution was heated and stirred at 70°C for 1 hour under a nitrogen stream. A mixture of 1.7 g of m-17 and 150 ml of DMF was slowly added dropwise to this reaction solution, and the mixture was stirred for another 1 hour. After that, it was cooled to room temperature, and ethyl acetate and distilled water were added to carry out an extraction operation. The obtained organic layer was concentrated to dryness. The obtained solid was purified by silica gel column chromatography (toluene:heptane mixture), and 3.2 g of m-18 was obtained (yield: 52%).

[0207] (2) Synthesis of compound m-19 The following reagents and solvents were placed in a 100 ml recovery flask. Compound m-18: 3.0g (6.2mmol) Sulfuric acid: 30ml Next, the reaction solution was stirred at 80°C for 7 hours under a nitrogen stream. After that, it was cooled to room temperature, poured into ice water, and filtered. The resulting solid was dispersed and washed with 100 ml of water for 1 hour, and then filtered to obtain a solid. The resulting solid was purified by silica gel column chromatography (chlorobenzene:ethyl acetate mixture) to obtain 1.9 g of m-19 (yield: 70%).

[0208] (3) Synthesis of compound C-17 The following reagents and solvents were placed in a 200 ml recovery flask. Compound m-19: 1.5g (3.0mmol) Compound m-20: 0.7g (3.6mmol) Sodium tert-butyloxide: 0.96 g (9.0 mmol) Pd(dba)2: 190mg xphos: 480mg Orthoxylene: 75ml The reaction solution was then heated and stirred at 140°C for 5 hours under a nitrogen stream. After the reaction was completed, the mixture was filtered through Celite and concentrated to dryness. The resulting solid was purified by silica gel column chromatography (toluene:ethyl acetate mixture) to obtain 1.1 g of C-17 (yield: 62%).

[0209] Mass spectrometry was carried out on Exemplary Compound C-17 in the same manner as in Example 1. [MALDI-TOF-MS] Measured value: m / z=535 Calculated value: C 37 H 29 NOS=535

[0210] [Examples 13 and 14 (Synthesis of Exemplary Compounds)] As shown in Table 4, the exemplary compounds shown in Examples 13 and 14 were synthesized in the same manner as in Example 12, except that raw material m-16 in Example 12 was replaced with raw material 1, raw material m-17 with raw material 2, and raw material m-20 with raw material 3. The actual measured values ​​(m / z) of the mass spectrometry results measured in the same manner as in Example 12 are also shown.

[0211] [Table 4]

[0212] [Example 15] In this example, a bottom-emission organic EL device was fabricated in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode were sequentially formed on a substrate.

[0213] 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 steps. Next, vacuum deposition was performed by resistance heating in a vacuum chamber to successively form the organic compound layer and electrode layer shown in Table 5 on the ITO substrate. At this time, the electrode area of ​​the opposing electrode (metal electrode layer, cathode) was set to 3 mm2. 2 The "% ratio" in Table 5 is a mass ratio.

[0214] [Table 5]

[0215] The device characteristics were measured and evaluated. The initial light-emitting characteristics were green light emission with a maximum external quantum efficiency (EQE) of 5.6%. Specifically, the current-voltage characteristics were measured using a Hewlett-Packard 4140B microcurrent meter, and the light-emitting brightness was measured using a Topcon BM7. Furthermore, the device was measured at a current density of 50 mA / cm. 2 A continuous driving test was conducted at 100°C, and the time until the brightness degradation rate reached 5% (LT95) was measured, which was 110 hours.

[0216] [Examples 16 to 20] An organic light-emitting device was produced in the same manner as in Example 15, except that the compounds in Example 15 were appropriately changed to those shown in Table 6. The characteristics of the obtained device were measured and evaluated in the same manner as in Example 15. The measurement results are shown in Table 6.

[0217] [Table 6]

[0218] [Example 21] An organic light-emitting device was produced in the same manner as in Example 15, except that the organic compound layer and electrode layer shown in Table 7 were successively formed. In Table 7, "ratio %" denotes a mass ratio.

[0219] [Table 7]

[0220] The device characteristics were measured and evaluated in the same manner as in Example 15. As the initial light-emitting characteristics, green light emission with a maximum external quantum efficiency (EQE) of 6.4% was obtained. Furthermore, at a current density of 50 mA / cm 2 A continuous driving test was conducted at 1000 rpm, and the time (LT95) until the brightness degradation rate reached 5% was measured, which was 143 hours.

[0221] [Examples 22 to 39, Comparative Examples 1 and 2 (Example 30 is a reference example) ] An organic light-emitting device was produced in the same manner as in Example 21, except that the compounds used in Example 21 were appropriately changed to those shown in Table 8. 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 8. Comparative compound 1 and comparative compound 2 are comparative compound 1 shown in Figure 1, Table 1, and comparative compound 2 shown in Figure 2, respectively.

[0222] [Table 8]

[0223] As shown in Table 8, the maximum external quantum efficiency (EQE) of Comparative Example 1 was low, at 4.0 or less. This is because the difference between S1 and T1 of Comparative Compound 1 was large, resulting in the absence of luminescence components due to delayed fluorescence. On the other hand, the devices of Examples 22 to 39 exhibited highly efficient luminescence. This is because the compound of this embodiment has a structure in which an electron-withdrawing carbonyl group is bonded while forming a ring structure, and has an electron-donating amino group, thereby reducing the difference between S1 and T1 and enabling the use of luminescence due to delayed fluorescence. Furthermore, the 5% degradation life of Comparative Example 2 was 50 hours, indicating poor durability. This is thought to be due to the shallow HOMO energy of Comparative Compound 2 (close to the vacuum level) and low oxidative stability. On the other hand, the devices of Examples 22 to 39 exhibited good durability, with a 5% degradation life of 100 hours or more. The compounds of this embodiment have deep HOMO energy (far from the vacuum level) and high oxidative stability, which is thought to be the reason for their excellent durability. [Explanation of symbols]

[0224] 1: interlayer insulating layer, 2: first electrode, 3: insulating layer, 4: organic compound layer, 5: second electrode, 6: protective layer, 7: color filter, 10: subpixel, 11: substrate, 12: insulating layer, 13: gate electrode, 14: gate insulating film, 15: semiconductor layer, 16: drain electrode, 17: source electrode, 18: TFT, 19: insulating film, 20: contact hole, 21: anode, 22: organic compound layer, 23: cathode, 24: first protective layer, 25: second protective layer, 26: organic light-emitting element, 100: display device< / x>

Claims

1. An organic compound represented by the following general formula [1]: 【Chemistry 1】 In the general formula [1], R 1 ~R 4 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triazyl group, and a silyl group; R 8 ~R 11 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted phenyl group, and a silyl group. 5 ~R 7 , R 12 ~R 14 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triazyl group, and a silyl group. 6 and the above R 7 , the R 12 and the above R 13 may be bonded to each other to form a ring structure. 1 ~R 4 , the R 8 ~R 11 One of the groups is a substituted or unsubstituted amino group. The groups bonded to the nitrogen atoms of the substituted or unsubstituted amino groups may be bonded to each other to form a ring structure. X is oxygen, sulfur, selenium, tellurium, Cr 15 R 16 R represents any one of the groups. 15 ~R 16 are each independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triazyl group, and a silyl group.

2. The R 6 ~R 7 , the R 12 ~R 13 The organic compound according to claim 1, wherein is not a hydrogen atom.

3. The R 8 ~R 11 3. The organic compound according to claim 1, wherein one of the groups is a substituted or unsubstituted amino group.

4. The R 8 ~R 11 4. The organic compound according to claim 1, wherein one of the groups is an amino group having any one of the following structures: 【Chemistry 2】 (* indicates the bond position.)

5. The R 8 ~R 11 5. The organic compound according to claim 4, wherein one of the groups is an amino group having any one of the following structures: 【Transformation 3】 (* indicates the bond position.)

6. 6. The organic compound according to claim 1, wherein X is selected from oxygen and sulfur.

7. The R 5 , R 14 7. The organic compound according to claim 1, wherein is any one of a hydrogen atom, a substituted or unsubstituted alkyl group, a phenyl group, a triazyl group, and fluorine.

8. The R 1 ~R 4 8. The organic compound according to claim 1, wherein is any one of a hydrogen atom, a substituted or unsubstituted alkyl group, a phenyl group, a triazyl group, and fluorine.

9. The R 1 ~R 4 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted triazyl group, and a silyl group; R 8 ~R 11 are each independently selected from a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted phenyl group, and a silyl group.

10. The R 2 is a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted triazyl group, 1 , R 3 , and R 4 2. The organic compound according to claim 1, wherein each of the groups is independently selected from a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, and a silyl group.

11. 11. The organic compound according to claim 10, wherein R2 is a substituted or unsubstituted triazyl group.

12. an anode and a cathode, an organic compound layer disposed between the anode and the cathode, 12. An organic light-emitting device, wherein at least one of the organic compound layers comprises the organic compound according to claim 1.

13. The organic light-emitting element according to claim 12, wherein the layer containing the organic compound is a light-emitting layer.

14. The organic light-emitting device according to claim 13 , wherein the light-emitting layer further comprises a host material.

15. The organic light-emitting device according to claim 14, wherein the host material is a hydrocarbon compound.

16. The organic light-emitting device according to claim 14 or 15, wherein the light-emitting layer further comprises a light-emitting material.

17. 17. The organic light-emitting device according to claim 16, wherein the light-emitting material is a hydrocarbon compound.

18. 18. The organic light-emitting device according to claim 13, wherein the light-emitting layer emits green or red light.

19. 19. 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 12 and an active element connected to the organic light-emitting element.

20. 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 12 .

21. 19. An electronic device comprising: a display unit having the organic light-emitting element according to claim 12; a housing in which the display unit is provided; and a communication unit provided in the housing and communicating with an external device.

22. 19. A lighting device comprising: a light source having the organic light-emitting element according to claim 12; and a light diffusion section or an optical filter that transmits light emitted by the light source.

23. A moving body comprising: a lighting fixture having the organic light-emitting element according to any one of claims 12 to 18; and a body on which the lighting fixture is provided.

24. An exposure light source for an electrophotographic image forming apparatus, comprising the organic light-emitting element according to claim 12 .

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