Heterocyclic compound and organic light-emitting element containing same

Abstract

The present disclosure provides, as a heterocyclic compound which has high horizontal orientation of a light-emitting material and high luminous efficiency, a heterocyclic compound that is represented by general formula (1) and has a calculated dipole moment value of 2.80 or more. In general formula (1), CYn is a group that is represented by general formula (2a) or (2b). Ra, Rb, and Rc each represent a plurality of substituents at each carbon atom that constitutes each ring structure, and R11 to R14, R21 to R26, Ra, Rb, and Rc each represent a hydrogen atom, deuterium or a substituent.

Description

Heterocyclic compound and organic light-emitting device containing the same

[0001] The present invention relates to a heterocyclic compound having high horizontal alignment and high luminous efficiency, an organic light-emitting element having the same, and a device or apparatus having the organic light-emitting element.

[0002] An organic light-emitting device (also called an organic electroluminescent device or organic EL device) is an electronic device that has a first electrode, a second electrode, and an organic compound layer disposed between these electrodes. By injecting electrons and holes from this pair of electrodes, charges move through the organic compound layer and recombine in the light-emitting layer containing a light-emitting organic compound. This recombination generates excitons, and the organic light-emitting device emits light when the excitons return to the ground state. Organic light-emitting devices are characterized by low driving voltage, a wide range of emission wavelengths, fast response, and the potential for thin and lightweight light-emitting devices, and are the subject of active research.

[0003] When an organic compound is electrically excited, as in an organic light-emitting device, it is known that a singlet excited state and a triplet excited state are generated in a ratio of 1:3 (25%:75%). Light emission from the singlet excited state is observed as fluorescence, and light emission from the triplet excited state is observed as phosphorescence. However, because phosphorescence is not typically observed at room temperature, the internal quantum efficiency of fluorescent materials is limited to 25%. However, organometallic complexes using heavy atoms such as iridium and platinum can convert the singlet excited state to the triplet excited state (heavy atom effect), achieving an internal quantum efficiency of 100%. Therefore, organic light-emitting devices using phosphorescence are theoretically expected to have approximately four times the luminous efficiency of organic light-emitting devices using fluorescence.

[0004] When using such phosphorescent materials, the light-emitting layer is formed by doping a few percent of the phosphorescent material into another organic compound to suppress quenching due to concentration quenching of the light-emitting material and triplet-triplet annihilation. The matrix compound into which the phosphorescent material is doped is called a host material. Therefore, since the majority of the light-emitting layer is made up of the host material, the host material of the light-emitting layer, which serves as the recombination region of electrons and holes, is required to have various physical properties, such as excellent hole and electron transport properties, high molecular stability, and a higher triplet excited state than the light-emitting material.

[0005] As organic compound host materials that have been created so far, Patent Document 1 describes the following compound A, and Patent Document 2 describes the following compound B.

[0006]

[0007] JP-T-2012-526833 A JP-A-2011-201869

[0008] Compound A described in Patent Document 1 is a molecule with high robustness and excellent horizontal alignment, but there is room for improvement in the carrier transport property when used as a host material, the horizontal alignment property of the light-emitting material, which is determined by the interaction with the light-emitting material (guest material) and the horizontal alignment property of the host material. Compound B described in Patent Document 2 has better carrier transport property than Compound A, but there is room for improvement in the horizontal alignment property of the light-emitting material.

[0009] To further improve the efficiency of organic light-emitting devices using phosphorescent materials, it is important to control not only the molecular robustness and carrier transport properties but also the interaction with the light-emitting material and the resulting horizontal alignment.

[0010] The present invention has been made in view of the above-mentioned problems, and an object of the present invention is to provide a heterocyclic compound that improves the horizontal alignment of a light-emitting material by utilizing the interaction between the heterocyclic compound and the light-emitting material, and that has high light-emitting efficiency when used as a host material.

[0011] The present invention provides a heterocyclic compound represented by the following general formula [1], which has a calculated permanent dipole moment of 2.80 or more.

[0012]

[0013] In the general formula [1], CYn is a group represented by the following general formula [2a] or [2b].

[0014]

[0015] In the general formulae [1], [2a] and [2b], R ａ , R ｂ , R ｃ represents a plurality of substituents at each carbon atom constituting each ring structure, and R１１ ~R １４ , R ２１ ~R ２６ , R ａ , R ｂ , R ｃ are each independently selected from a hydrogen atom, deuterium, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, an amino group, a cyano group, and a silyl group, m is an integer of 1 to 10, X is CRR', SiRR', S, SO, SO ２ ,NR,O,Se,PRR',PO,SeO ２ wherein R and R' are each independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a halogen atom; a carbon atom forming a ring structure may be bonded to a carbon atom adjacent to the carbon atom forming the ring structure to form a further ring structure; * represents a bonding position between general formula [1] and general formula [2a] or [2b].

[0016] The organic light-emitting device of the present invention is an organic light-emitting device having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, wherein the organic compound layer contains the heterocyclic compound of the present invention.

[0017] According to the present invention, a heterocyclic compound having a high horizontal alignment property of a light-emitting material and high luminous efficiency can be provided, and an organic light-emitting element having excellent luminous properties, as well as various devices and equipment having the organic light-emitting element, can be provided.

[0018] FIG. 1 is a schematic cross-sectional view showing an example of a pixel of a display device according to one embodiment of the present invention. FIG. 2 is a schematic cross-sectional view of an example of a display device using an organic light-emitting element according to one embodiment of the present invention. FIG. 3 is a schematic view showing an example of a display device according to one embodiment of the present invention. FIG. 4 is a schematic view showing an example of an imaging device according to one embodiment of the present invention. FIG. 5 is a schematic view showing an example of an electronic device according to one embodiment of the present invention. FIG. 6 is a schematic view showing an example of a display device according to one embodiment of the present invention. FIG. 7 is a schematic view showing an example of a bendable display device. FIG. 8 is a schematic view showing an example of an illumination device according to one embodiment of the present invention. FIG. 9 is a schematic view showing an example of an automobile having a vehicle lamp according to one embodiment of the present invention. FIG. 10 is a schematic view showing an example of a wearable device according to one embodiment of the present invention. FIG. 11 is a schematic view showing an example of a wearable device according to one embodiment of the present invention, having an imaging device. FIG. 12 is a schematic view showing an example of an image forming apparatus according to one embodiment of the present invention. FIG. 13 is a schematic view of an exposure light source of an image forming apparatus according to one embodiment of the present invention.

[0019] Hereinafter, embodiments of the present invention will be described. The present invention is not limited to the following description, and it will be readily understood by those skilled in the art that various changes can be made in form and detail without departing from the spirit and scope of the present invention. In other words, the present invention should not be interpreted as being limited by the following description.

[0020] [Heterocyclic Compound] The heterocyclic compound of the present invention is represented by the following general formula [1] and has a calculated permanent dipole moment of 2.80 or more.

[0021]

[0022] In the general formula [1], CYn is a group represented by the following general formula [2a] or [2b].

[0023]

[0024] In the general formulae [1], [2a] and [2b], R ａ , R ｂ , R ｃ represents a plurality of substituents at each carbon atom constituting each ring structure, and R １１ ~R１４ , R ２１ ~R ２６ , R ａ , R ｂ , R ｃ are each independently selected from a hydrogen atom, deuterium, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, an amino group, a cyano group, and a silyl group.

[0025] In particular, R ２１ is preferably an alkyl group having 1 to 4 carbon atoms, and when it is a methyl group having 1 carbon atom, the interaction energy with the light-emitting material becomes large, and the high horizontal alignment property of the heterocyclic compound also improves the horizontal alignment property of the light-emitting material, which is preferable, thereby increasing the light extraction efficiency of the organic light-emitting element. ２１ However, when the group is a cyano group or a trifluoromethyl group, the electron transport property is improved, and therefore it is an effective means for controlling the carrier balance in the light-emitting layer.

[0026] m is an integer of 1 to 10, preferably 1.

[0027] X is CRR', SiRR', S, SO, SO ２ ,NR,O,Se,PRR',PO,SeO ２ wherein R and R' are each independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a halogen atom. Preferably, R is O, S, Se, or NR. In the case of O or S, the highest occupied molecular orbital (HOMO) of the heterocyclic compound becomes shallower, thereby improving hole injection and transport properties, and more preferably S.

[0028] The carbon atoms forming the ring structure may be bonded to the carbon atoms adjacent to the carbon atom to form a further ring structure. When the carbon atoms are bonded to each other to form a ring structure, the ring structure may be an alicyclic structure, an aromatic ring, or a heterocyclic ring. The number of fused rings constituting the ring structure may be 1 to 3, and is preferably 1.

[0029] * indicates the bonding position between general formula [1] and general formula [2a] or [2b].

[0030] The above CYn is preferably represented by the above general formula [2b].

[0031] The heterocyclic compound of the present invention is preferably a compound having a structure represented by the following general formula [3], since it can achieve excellent horizontal alignment and high luminous efficiency compared to a compound having a ring structure at another position. １１ ~R １４ , R ２１ ~R ２６ represents R in the general formulas [1], [2a], and [2b]. １１ ~R １４ , ２１ ~R ２６ is the same as R in the general formula [3] ３１ ~R ３４ is R in the general formula [1] １１ ~R １７ and X in the general formula [3] is the same as X in the general formula [1].

[0032]

[0033] Hereinafter, R in the general formulas [1], [2a], [2b], and [3] １１ ~R １４ , R ２１ ~R ２６ , R ３１ ~R ３４ , R ａ , R ｂ , R ｃ The halogen atoms, alkyl groups, aryl groups, heterocyclic groups, alkoxy groups, aryloxy groups, amino groups, and silyl groups exemplified as R and R' will be explained below.

[0034] The halogen atom includes, but is not limited to, fluorine, chlorine, bromine, iodine, etc., and among these, a fluorine atom is preferred.

[0035] Examples of the alkyl group include alkyl groups having from 1 to 10 carbon atoms, more preferably from 1 to 8 carbon atoms, and even more preferably from 1 to 4 carbon atoms. Specific examples include, but are not limited to, a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, a t-butyl group, a s-butyl group, an octyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, and a 2-adamantyl group.

[0036] The aryl group may be an aryl group having from 6 to 18 carbon atoms, such as a phenyl group, a naphthyl group, an indenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a phenanthryl group, or a triphenylenyl group.

[0037] Examples of the heterocyclic group include heterocyclic groups having 3 to 15 carbon atoms. The heterocyclic group may have nitrogen, sulfur, or oxygen as a heteroatom. Specific examples include pyridyl, pyrazyl, pyrimidyl, triazyl, imidazolyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, carbazolyl, acridinyl, phenanthrolyl, furanyl, thiophenyl, dibenzofuranyl, and dibenzothiophenyl groups, but are not limited thereto.

[0038] Examples of the alkoxy group include alkoxy groups having from 1 to 10 carbon atoms, more preferably from 1 to 6 carbon atoms, and even more preferably from 1 to 4 carbon atoms. Specific examples include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, a 2-ethyl-hexyloxy group, and a benzyloxy group.

[0039] Examples of the aryloxy group include, but are not limited to, a phenoxy group.

[0040] The amino group may be unsubstituted or substituted with an alkyl group, an aryl group, or an amino group. The alkyl group, aryl group, and amino group may have a halogen atom as a substituent. The aryl group and amino group may have an alkyl group as a substituent. The alkyl groups substituted in the amino group may be bonded to each other to form a ring. Specific examples 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-t-butylphenyl)amino group, an N-phenyl-N-(4-trifluoromethylphenyl)amino group, and an N-piperidyl group.

[0041] Examples of the silyl group include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0042] The alkyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group, and amino group may have a deuterium atom, a halogen atom, or a heterocyclic group as a substituent. Examples of alkyl groups having a deuterium atom as a substituent include -CD ３ , -CD ２ CH ３ , -CD ２ CD ３ Examples of halogen atoms include, but are not limited to, fluorine, chlorine, and bromine, with fluorine atoms being preferred, and trifluoride methyl groups (—CF ３ ), a pentafluoroethyl group (—C ２ F ５ ) are listed.

[0043] The alkyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group, and amino group may have a heterocyclic group, amino group, or aryl group as a substituent. The heterocyclic group may have 3 to 9 carbon atoms. The heterocyclic group may have nitrogen, sulfur, or oxygen as a heteroatom. More specifically, it may be a pyridyl group or a pyrrolyl group. The amino group may have an alkyl group or an aryl group, and the alkyl groups may be bonded to each other to form a ring. More specifically, it may be a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, or a ditolylamino group. The aryl group may have 6 to 12 carbon atoms. More specifically, it may be a phenyl group, a biphenyl group, or a naphthyl group.

[0044] The alkyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group, and amino group may have, as a substituent, an aralkyl group such as a benzyl group, an alkoxy group such as a methoxy group, an ethoxy group, or a propoxy group, an aryloxy group such as a phenoxy group, or a cyano group.

[0045] The amino group, aryl group, heterocyclic group, and aryloxy group may have an alkyl group as a substituent. The alkyl group may have 1 to 10 carbon atoms. More specifically, the alkyl group may be a methyl group, an ethyl group, a normal propyl group, an isopropyl group, a normal butyl group, or a t-butyl group. The substituent is not limited to these.

[0046] The heterocyclic compound of the present invention, when used as a host material in the light-emitting layer of an organic light-emitting device, not only exhibits high horizontal alignment of the host material relative to the substrate, but also improves the horizontal alignment of the light-emitting material due to the interaction between the host material and the light-emitting material, thereby improving the luminous efficiency of the organic light-emitting device. Here, the molecular orientation of the host material in the light-emitting layer of the organic light-emitting device refers to the ring structure of the host material being aligned horizontally relative to the substrate surface of the organic light-emitting device. Furthermore, the molecular orientation of the light-emitting material refers to the transition dipole moment of the light-emitting material doped into the host material being aligned horizontally relative to the substrate surface of the organic light-emitting device. Since the light emission direction from the light-emitting material is primarily perpendicular to the transition dipole moment of the molecule, when the light-emitting material exhibits high horizontal alignment, light loss due to the substrate mode, waveguide mode, and surface plasmon polariton mode is reduced, improving the outcoupling mode (light extraction efficiency).

[0047] The horizontal alignment of the emissive molecules is determined by the horizontal alignment of the host material, which accounts for the majority of the emissive layer, and its interaction with the host. Host molecules have a ring structure and generally possess a permanent dipole moment, but their permanent dipole moment and ring structure tend to be oriented parallel to the substrate surface. Many fluorescent materials have the same permanent and transition dipole moments, which align with the host's permanent dipole moment. Therefore, when the host molecules have a high horizontal alignment, the transition dipole moment of the emissive material is also parallel to the substrate, improving light extraction efficiency. On the other hand, organometallic complexes that exhibit phosphorescence have their permanent and transition dipole moments orthogonal to each other. Therefore, when the permanent dipole moment of the emissive molecule is large, the emissive molecule will be oriented so that its permanent dipole moment is aligned with the permanent dipole moments of the numerous host molecules surrounding it. This results in the emissive molecule's permanent dipole moment being parallel to the substrate surface, resulting in poor horizontal alignment. On the other hand, when the permanent dipole moment of the luminescent molecule is small, the luminescent molecule is oriented so that the ring structure of the host molecule and the ring structure of the luminescent molecule are parallel. Therefore, in a luminescent material with a small permanent dipole moment and a transition dipole moment in the direction of a fused ring structure, the transition dipole moment of the luminescent material also aligns horizontally with the substrate surface due to interaction with the ring structure of the host material, thereby improving the luminous efficiency. Therefore, when the host molecule-guest molecule interaction is strong and the orientation of the host molecule is high, the orientation of the guest molecule also increases, so a strong interaction force is preferable. In particular, it is preferable for the guest molecule to have a highly planar fused polycyclic moiety or a heteroatom, as this strengthens the host molecule-guest molecule interaction.

[0048] <Calculation of horizontal alignment of host material> The horizontal alignment of a host material can be predicted from the host material's three-dimensional structure, molecular weight, and permanent dipole moment. Disk-shaped and rod-shaped molecules are more likely to align horizontally due to their own weight than spherical molecules, and molecules with larger molecular weights are more likely to align horizontally than small molecules. Furthermore, host materials with a large permanent dipole moment have strong dipole-dipole interactions, so host materials stack together and align horizontally to the substrate.

[0049] The transition dipole moment and orientation parameter S of the fluorescent material represented by the general formula [1] can be calculated and predicted by the following formula: S=0.676x １ +0.525x ２ -0.0420x ３ -0.000479x ４ -0.41 where x １ is the x-coordinate value in the PMI (Principal Moments of Inertia) plot of the fluorescent material, x ２ are the y-coordinate values ​​in the principal moment of inertia plot, and are indices that represent the three-dimensional structure of the molecule, respectively. ３ is the permanent dipole moment, x ４ is the molecular weight.

[0050] The x- and y-coordinate values ​​of the principal moments of inertia are determined by normalizing the three principal moments of inertia I1, I2, and I3 (I1<I2<I3) with the largest principal moment of inertia (I1 / I3, I2 / I3).

[0051] The calculation procedure is as follows: The molecular structure and dipole moment of the electronic ground state are calculated using the electronic state calculation software Gaussian 16. ＊ Revision C.01. In this case, the density functional theory is adopted as the quantum chemical calculation method, and the function is B3LYP and the basis function is 6-31G. ＊was used. Also, the molecular structure obtained from the above calculations was used for the calculations of I1, I2, and I3, and RDKit 2022.03.5, which is descriptor calculation software, was used. Gaussian 16 Revision C.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gompertz, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasagawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery Jr., J. E. Peralta, F. Oglialoro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cami, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, and D. J. Fox, Gaussian Inc., Wallingford CT (2019).

[0052] Here, the calculated permanent dipole moment of the molecule is preferably 2.80 or more and 4.00 or less, and more preferably 2.80 or more and 3.80 or less, because if the permanent dipole moment is too large, the molecules will aggregate and the luminous efficiency will decrease.

[0053] <Calculation of Interaction Energy Between Host Material and Light-Emitting Material (Guest Material)> The interaction energy between a host material such as a heterocyclic compound and a phosphorescent material, i.e., the change in free energy (PMF: Potential of Mean Force), was calculated using the umbrella sampling method of molecular dynamics calculation software GROMACS 2019.6 (Copyright (c) 2001-2018, The GROMACS development team at Uppsala University, Stockholm University and the Royal Institute of Technology, Sweden). In the umbrella sampling method, relative coordinates are taken in the Z-axis direction for two types of molecules, and a pseudo-stable state is created by adding a bias potential, and the potential is calculated. This calculation is performed multiple times while changing the relative distance between the two molecules. Then, the influence of the bias potential is removed using the WHAM (Weighted Histogram Analysis Method), and the difference between the minimum and maximum energy states from the obtained PMF is taken as the interaction energy.

[0054]

[0055] The above chemical structure is the exemplary compound (13) described later, and in the general formula [1], CYn is the general formula [2a], m is 1, X is a sulfur atom, and R １１ ~R １４ , R ２１ ~R ２６ , R ａ , R ｂ , R ｃ In other words, the exemplary compound (13) has a molecular structure in which X is a sulfur atom and R １１ ~R １４ , R２１ ~R ２６ , R ３１ ~R ３４ are all hydrogen atoms. Here, the permanent dipole moment and orientation parameter S were calculated for Compound A and Compound B described in Patent Documents 1 and 2, and for the exemplary compound (13) according to the present invention, which will be described later. Table 1 shows the results of the calculation of the permanent dipole moment and the degree of molecular orientation calculated from the orientation parameter S. The degree of molecular orientation is expressed as 100% when the permanent dipole moment of each molecule is horizontal to the substrate, and 0% when it is vertical (random is 66.7%).

[0056]

[0057] Similarly, the permanent dipole moment and orientation parameter S were calculated for Compound C, Compound D, and Exemplary Compounds (14) and (156), and the degree of molecular orientation of the molecules was calculated. The results are shown in Table 2.

[0058]

[0059] As shown in Table 1, the molecular orientation degree of exemplary compound (13) is 82.1%, which is higher than the molecular orientation degree of compound A (80.6%) and the molecular orientation degree of compound B (74.7%). Furthermore, as shown in Table 2, the molecular orientation degree of compound C is 75.1%, which indicates that the molecular orientation degree of exemplary compound (13) is higher. As described above, molecular weight is also involved in calculating the orientation parameter S, and compound D, which has one more phenylene than compound B, also has an increased molecular weight, resulting in an improved molecular orientation degree. However, exemplary compound (156), which has the same molecular weight, has a molecular orientation degree of 84.1%, which indicates superior orientation. As described above, comparisons between compounds B and C, exemplary compound (13), and exemplary compound D and exemplary compound (156), which have the same molecular weight, reveal that the quinazoline skeleton having a nitrogen atom on the outer side in the heterocyclic compound of the present invention increases the permanent dipole moment of the heterocyclic compound and improves the molecular orientation degree.

[0060] Next, the interaction energies of the luminescent materials RD-10 and RD-11 described below were calculated for each of Exemplary Compound (13), Exemplary Compound (14), Compound A, and Compound E. The results are shown in Table 3. Both RD-10 and RD-11 are organometallic compounds having a benzoisoquinoline skeleton in the ligand. RD-11 has a trifluoromethyl group, which is a polar group, in the benzoisoquinoline moiety, while RD-10 is an organometallic compound that does not have a polar group in the unsubstituted benzoisoquinoline moiety.

[0061]

[0062] As shown in Table 3, it can be seen that exemplary compounds (13) and (14) have higher interaction energies with RD-10 and RD-11 than compound A. Furthermore, exemplary compounds (13) and (14) have higher interaction energies with RD-11, which has a polar group, than RD-10, which does not have a polar group. ２１ It was found that exemplary compound (14), which has a methyl group at , has a stronger interaction with RD-10 and RD-11 than exemplary compound (13). Compound E is a heterocyclic compound having a quinazoline skeleton, like exemplary compounds (13) and (14), but it was found that it has a smaller interaction energy with RD10 and RD-11 (particularly RD-10).

[0063] From the above, it was found that heterocyclic compounds having a quinazoline skeleton in which the nitrogen atom faces outward, such as exemplary compound (13) and exemplary compound (14), have a strong interaction with guest materials and contribute to excellent horizontal alignment of the guest materials.

[0064] Specific structural formulae of the heterocyclic compound according to the present invention are shown below, but the heterocyclic compound according to the present invention is not limited to these.

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078] The above-mentioned exemplified compounds are examples of heterocyclic compounds represented by the general formula [1]. Among the exemplified compounds, the organic compound group in which X is a sulfur atom, an oxygen atom, or NR improves hole transportability in addition to electron transportability due to the quinazoline skeleton, and therefore can reduce the driving voltage of the device. ２１ By providing an electron-withdrawing group such as a cyano group, a fluoro group, or a trifluoromethyl group to the compound, the electron transport property can be further improved. Furthermore, by providing the number of phenylenes, m, in the general formula [1] as 1 and by providing an appropriate alkyl group as a substituent, the compound can be suitably used as a compound with excellent vapor deposition properties. In the case of a coating-type device, a larger m results in better horizontal alignment and improved luminous efficiency. Furthermore, by providing an appropriate alkyl group as a substituent, the compound can be suitably used as a compound with excellent solubility and horizontal alignment properties.

[0079] In all of the above organic compounds, the quinazoline skeleton with the nitrogen atom facing outward contributes to a large permanent dipole moment, interaction with the guest material, and horizontal alignment, thereby achieving high horizontal alignment of the transition dipole moment of the guest material relative to the substrate and exhibiting high luminous efficiency in the organic light-emitting device.

[0080] [Organic Light-Emitting Element] The organic light-emitting element of the present invention has at least a first electrode, a second electrode, and an organic compound layer disposed between these electrodes. One of the first electrode and the second electrode is an anode and the other is a cathode.

[0081] <Organic Compound Layer> In the organic light-emitting device of the present invention, the organic compound layer may be a single layer or a laminate consisting of multiple layers, as long as it has a light-emitting layer. Here, when the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have, in addition to the light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole / exciton blocking layer, an electron transport layer, an electron injection layer, etc. Furthermore, the light-emitting layer may be a single layer or a laminate consisting of multiple layers.

[0082] The organic compound layer is mainly composed of an organic compound, but may also contain inorganic atoms or inorganic compounds, such as copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, or zinc. The organic compound layer may be disposed between the first electrode and the second electrode and in contact with the first electrode and the second electrode.

[0083] The organic compound layer can be formed by a dry process such as vacuum deposition, ionization deposition, sputtering, plasma, etc. Alternatively to the dry process, a wet process can be used in which the organic compound is dissolved in an appropriate solvent and a layer is formed by a known coating method (e.g., spin coating, dipping, casting, LB method, inkjet method, etc.).

[0084] 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.

[0085] 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.

[0086] 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.

[0087] In the organic light-emitting device of the present invention, at least one of the organic compound layers contains the heterocyclic compound of the present invention. Specifically, the heterocyclic compound of the present invention is contained in any of the above-mentioned light-emitting layer, hole-injection layer, hole-transport layer, electron-blocking layer, hole / exciton-blocking layer, electron-transport layer, electron-injection layer, etc., and is preferably contained in the light-emitting layer.

[0088] In the organic light-emitting device of the present invention, when the heterocyclic compound of the present invention is contained in the light-emitting layer, the light-emitting layer may be a layer consisting of only the heterocyclic compound of the present invention, or may be a layer consisting of an organometallic complex, other light-emitting materials, or other compounds. In this case, the heterocyclic compound of the present invention may be a sole host material in the light-emitting layer, or may be an light-emitting layer consisting of other host materials and assist materials.

[0089] Here, the other light-emitting material refers to a material that emits fluorescence, thermally activated delayed fluorescence, or phosphorescence. The host material is a matrix compound having a larger mass ratio than the light-emitting material and assist material that constitute the light-emitting layer, and the assist material is a compound that, among the compounds that constitute the light-emitting layer, has a mass ratio smaller than that of the host and assists the emission of the guest. When the host material is referred to as the first organic compound and the assist material is referred to as the second organic compound, the first organic compound has a higher minimum excited singlet energy and a lower minimum excited triplet energy than the organometallic complex and the thermally activated delayed fluorescent material. The lowest excited triplet energy of the second organic compound may be higher than the lowest excited triplet energy of the organometallic complex and the thermally activated delayed fluorescent material, but lower than the lowest excited triplet energy of the first organic compound.

[0090] When the heterocyclic compound of the present invention is used as a host material or an assist material in the light-emitting layer, the concentration thereof is preferably from 10.0% by mass to 99.9% by mass, more preferably from 25.0% by mass to 99.5% by mass, based on the total mass of the light-emitting layer.

[0091] The present inventors have conducted various studies and found that when the heterocyclic compound of the present invention is used as a host material or assist material for the light-emitting layer, particularly as a host material for the light-emitting layer, a device exhibiting high efficiency and high luminance light output and extremely high durability can be obtained. This light-emitting layer may be a single layer or multiple layers, and it is also possible to mix colors by including a light-emitting material having another light-emitting color. Multiple layers refer to a state in which the light-emitting layer is stacked with another light-emitting layer. In this case, the light-emitting color of the organic light-emitting device is not limited to red, green, or blue. More specifically, it may be white or a neutral color. In the case of white, for example, if one light-emitting layer emits red light, the other light-emitting layer emits a color other than red, i.e., blue or green. Furthermore, the film formation method is performed by vapor deposition or coating film formation.

[0092] When the light-emitting layer is formed by coating, a light-emitting ink composition containing the heterocyclic compound of the present invention, a light-emitting material, and a solvent can be prepared and used. Details will be described in detail in the examples below.

[0093] When the organic heterocyclic compound according to this embodiment is contained in the light-emitting layer, a first organic compound layer different from the light-emitting layer may be provided between the light-emitting layer and the second electrode. The first organic compound layer preferably has a higher minimum excited triplet energy than the light-emitting layer. Furthermore, a second organic compound layer different from the light-emitting layer may be provided between the light-emitting layer and the first electrode. The second organic compound layer preferably has a higher minimum excited triplet energy than the light-emitting layer.

[0094] The organic heterocyclic compound according to this embodiment can be used as a constituent material of an organic compound layer other than the light-emitting layer constituting the organic light-emitting device of this embodiment. Specifically, it may be used as a constituent material of an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, etc. In this case, the emission color of the organic light-emitting device is not limited to red, blue, or green. More specifically, it may emit white light or an intermediate color.

[0095] In addition to the heterocyclic compound of the present invention, 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.

[0096] As the hole injection transport material, a material with high hole mobility is preferred so that it can easily inject holes from the anode and transport the injected holes to the light-emitting layer. Furthermore, a material with a high glass transition temperature is preferred to suppress 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 shown below, but of course, are not limited to these.

[0097]

[0098] Among the hole-transporting 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 elements. 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.

[0099] Examples of light-emitting materials mainly involved in light-emitting function include fused ring compounds (for example, 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.

[0100] Specific examples of compounds that can be used as light-emitting materials are shown below, but the present invention is not limited to these.

[0101]

[0102]

[0103] When the light-emitting material is an organometallic complex such as an iridium complex or a platinum complex, which allows for the observation of phosphorescence, or a thermally activated delayed fluorescence material, which allows for the upconversion of triplet excitons to singlet excitons and the observation of fluorescence, it is preferable because it can emit light more efficiently than ordinary fluorescent light-emitting materials, and organometallic complexes such as an iridium complex or a platinum complex, which have high molecular stability, are more preferable.

[0104] Among the above-mentioned exemplary compounds, the iridium complexes from which phosphorescence can be observed are BD9, GD10 to GD15, and RD3 to RD11.

[0105] In addition to the heterocyclic compound of the present invention, examples of the host material or the light-emitting assist material that may be contained in the light-emitting layer include aromatic hydrocarbon compounds or derivatives thereof, as well as carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organic aluminum complexes such as tris(8-quinolinolato)aluminum, organic beryllium complexes, and organic iridium complexes.

[0106] Specific examples of compounds that can be used as the host material or the light-emitting assist material in the light-emitting layer other than the heterocyclic compound of the present invention are shown below, but the present invention is not limited to these.

[0107]

[0108] When the host material contains a heteroatom in the molecule, the electron and hole transport properties are improved, and the effect of improving efficiency is significant, which is preferable. A heteroatom is an atom other than carbon and hydrogen contained in the molecule, and compounds containing such an atom include EM27 to EM32 among the above-mentioned exemplary compounds. The heterocyclic compound of the present invention has excellent electron transport properties, and therefore is preferable for low voltage and high efficiency when combined with a host material and an assist material having hole transport properties. In the case of a red light-emitting element using a red light-emitting material, it is preferable to use an organometallic complex such as GD10 to GD15 as an assist material, because it can achieve high efficiency by efficient energy transfer to the red light-emitting material.

[0109] The electron transporting material can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light-emitting layer, and is selected in consideration of the balance with the hole mobility of the hole transporting material. Examples of materials having electron transporting properties include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, and fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.). Furthermore, the above electron transporting materials are also suitable for use in hole-blocking layers.

[0110] Specific examples of compounds that can be used as electron transporting materials are shown below, but the present invention is not limited to these.

[0111]

[0112] The electron injection material can be arbitrarily selected from those that can easily inject electrons from the cathode, and is selected in consideration of the balance with hole injection properties, etc. Examples of 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. Furthermore, the electron injection material can be used in combination with the above-mentioned electron transport material.

[0113] In general, an 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 protective layer. The planarizing layer may be made of acrylic resin or the like. The same applies when a planarizing layer is provided between the color filter and the microlens. Below, each component of an organic light-emitting element other than the organic compound layer will be described.

[0114] <Substrate> Examples of the substrate include quartz, glass, silicon wafer, resin, and metal. Furthermore, the substrate may be provided with a switching element such as a transistor and wiring, and an insulating layer thereon. The insulating layer may be made of any material as long as it can form a contact hole so that wiring can be formed between the first electrode and the insulating layer, and can ensure insulation from wiring that is not connected. For example, resins such as polyimide, silicon oxide, silicon nitride, etc. can be used.

[0115] <Electrodes> 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.

[0116] The anode material should preferably have as large a work function as possible. Examples of such materials 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.

[0117] 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.

[0118] 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 technology can be used to form the electrode.

[0119] 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.

[0120] 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 preferable because they provide good film coverage and make it easier to reduce resistance.

[0121] <Protective Layer> A protective layer may be provided on the second electrode. For example, by adhering glass with a moisture absorbent to the second electrode, the intrusion of water and other contaminants into the organic compound layer can be reduced, thereby reducing the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the second electrode to reduce the intrusion 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, it may be 50% or less, or even 10% or less.

[0122] <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 the substrate on which the organic light-emitting element is provided may be bonded to the color filter. Alternatively, a color filter may be patterned on the protective layer described above using photolithography technology. The color filter may be made of a polymer.

[0123] <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.

[0124] 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.

[0125] <Microlenses> An organic light-emitting element or an organic light-emitting device having an organic light-emitting element 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 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 the 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 the tangent and the semicircle.

[0126] 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.

[0127] <Counter Substrate> An counter substrate may be provided on the planarization layer. The counter substrate is called the counter substrate because it is provided at a position corresponding to the aforementioned substrate. The constituent material of the counter substrate may be the same as that of the aforementioned substrate. When the aforementioned substrate is defined as the first substrate, the counter substrate may be the second substrate.

[0128] <Pixel Circuit> The organic light-emitting device 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 a plurality of organic light-emitting elements 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 an organic light-emitting element, a transistor that controls the emission brightness of the organic 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.

[0129] The organic light-emitting device has a display area and a peripheral area arranged around the display area. The display area has pixel circuits, and the peripheral area has a display control circuit. The mobility of transistors constituting the pixel circuits may be lower than the mobility of transistors constituting the display control circuit.

[0130] The slope of the current-voltage characteristics of the transistors that make up the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistors that make up the display control circuit. The slope of the current-voltage characteristics can be measured by the so-called Vg-Ig characteristics.

[0131] The transistors that make up the pixel circuit are transistors that are connected to the organic light-emitting element.

[0132] Pixels An organic light-emitting device has a plurality of pixels. Each pixel has sub-pixels that emit different colors. The sub-pixels may emit, for example, RGB colors.

[0133] A pixel has an area, also called a pixel aperture, that emits light. 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.

[0134] The distance between subpixels may be 10 μm or less, specifically 8 μm, 7.4 μm, or 6.4 μm. The pixels may have a known arrangement in plan view. For example, they may have a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement. The shape of the subpixels in plan view may be any known shape. For example, they may have a rectangle, a quadrangle such as a diamond, or a hexagon. 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.

[0135] The organic light-emitting device of the present invention can be used as a component of a display device or a lighting device, and can also be used as an exposure light source for an electrophotographic image forming device, a backlight for a liquid crystal display device, a light-emitting device having a white light source and a color filter, etc.

[0136] 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 the display unit.

[0137] 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.

[0138] Next, the display device according to this embodiment will be described with reference to the drawings.

[0139] 1A and 1B are cross-sectional views 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).

[0140] 1A shows an example of a pixel, which is a component of the display device according to this embodiment, where 8 is an organic light-emitting element. The pixel has sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B based on the light emitted from the sub-pixels. The emitted colors may be distinguished by the wavelength of light emitted from the light-emitting layer, or the light emitted from the sub-pixels may be selectively transmitted or color-converted using a color filter or the like. Each sub-pixel has a first electrode 2, which is a reflective electrode, 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 5, a protective layer 6, and a color filter 7.

[0141] A transistor and a capacitor 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).

[0142] 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 of the first electrode 2 where the insulating layer 3 is not disposed contacts the organic compound layer 4 and becomes a light-emitting region.

[0143] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0144] The protective layer 6 reduces the penetration of moisture into the organic compound layer. Although the protective layer is illustrated as being one layer, it may be multiple layers. 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 may be formed on a planarization film (not shown). A resin protective layer (not shown) may be provided on the color filters. The color filters may be formed on a protective layer 6. Alternatively, the color filters may be provided on an opposing substrate such as a glass substrate and then bonded thereto.

[0146] 1B shows 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. A gate electrode 13, a gate insulating film 14, and a semiconductor layer 15 of the TFT 18 are disposed on the insulating layer 12. The TFT 18 also includes the semiconductor layer 15, 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 between the electrodes (anode, cathode) included in the organic light-emitting element 26 and the electrodes (source electrode, drain electrode) included in the TFT is not limited to the mode shown in Fig. 1B. In other words, it is sufficient that either the anode or the cathode is electrically connected to either the source electrode or the drain electrode of the TFT. TFT stands for thin film transistor.

[0148] 1B, 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 of FIG. 1B, a transistor is used as the switching element, but other switching elements may be used instead.

[0150] Also, the transistor used in the display device of FIG. 1B is not limited to a transistor using a single crystal silicon wafer, and a thin film transistor having an active layer on the insulating surface of the substrate may also be used. Examples of the active layer include non-single crystal silicon such as single crystal silicon, amorphous silicon, and microcrystalline silicon, and non-single crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Note that the thin film transistor is also called a TFT element.

[0151] The transistor included in the display device of FIG. 1B may be formed in a substrate such as a Si substrate. Here, forming in the substrate means manufacturing a transistor by processing the substrate itself such as a Si substrate. That is, having a transistor in the substrate can also be regarded as the substrate and the transistor being integrally formed.

[0152] The organic light-emitting element according to this embodiment has its emission luminance controlled by a TFT, which is an example of a switching element, and an image can be displayed by the emission luminance of each organic light-emitting element provided on a plurality of planes. Note that the switching element according to this embodiment is not limited to a TFT, and may be a transistor formed of low-temperature polysilicon or an active matrix driver formed on a substrate such as a Si substrate. "On the substrate" can also mean "in the substrate". Whether to provide a transistor in the substrate or use a TFT is selected according to the size of the display portion. For example, if the size is about 0.5 inches, it is preferable to provide an organic light-emitting element on a Si substrate.

[0153] 2 is a schematic diagram showing an example of a display device according to this embodiment. The display device 1000 may have a touch panel 1003, a display panel 1005, a frame 1006, a circuit board 1007, and a battery 1008 between an upper cover 1001 and a lower cover 1009. Flexible printed circuits FPCs 1002 and 1004 are connected to the touch panel 1003 and the display panel 1005. 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, and the red, green, and blue colors may be arranged in a delta configuration in the color filters.

[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 in 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] 3A is a schematic diagram illustrating an example of an imaging device according to this embodiment. The imaging device 1100 may include a viewfinder 1101, a rear display 1102, an operation unit 1103, and a housing 1104. The viewfinder 1101 may include 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 quickly as possible. Therefore, it is preferable to use a display device using organic light-emitting elements, because organic light-emitting elements have a fast response speed. A display device using organic light-emitting elements 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 may include an imaging method that detects the difference from the previous image, or a method of cutting out an image that is constantly being recorded.

[0160] FIG. 3B 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 may be a biometric recognition unit that recognizes a fingerprint to perform operations such as unlocking. An electronic device having a communication unit can also be called a communication device. The electronic device 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. Examples of the electronic device include a smartphone and a laptop computer.

[0161] 4A and 4B are schematic diagrams illustrating an example of a display device according to this embodiment. FIG. 4A illustrates a display device such as a television monitor or a PC monitor. The display device 1300 includes a frame 1301, a display unit 1302, and a base 1303 that supports the display unit 1302. The light-emitting device according to this embodiment is used for the display unit 1302. The frame 1301 and the base 1303 are not limited to the configuration shown in FIG. 4A . 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. 4B is a schematic diagram illustrating another example of a display device according to the present embodiment. The display device 1310 in FIG. 4B 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 each have a light-emitting device according to the present 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] 4A is a schematic diagram illustrating an example of an illumination device according to this embodiment. The illumination device 1400 includes a housing 1401, a light source 1402, a circuit board 1403, an optical filter 1404, and a light diffusion unit 1405. The light source includes 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 1402. The light diffusion unit 1405 can effectively diffuse light from the light source 1402, such as for illumination, and deliver the light over a wide area. The optical filter 1404 and the light diffusion unit 1405 may be provided on the light emission side of the illumination device. If necessary, a cover may be provided on the outermost surface.

[0164] The lighting device 1400 is, for example, a device that illuminates a room. The lighting device 1400 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 1400 may have an organic light-emitting element of the present invention and a power supply circuit connected thereto. The power supply circuit is a circuit that converts AC voltage into DC voltage. Furthermore, white has a color temperature of 4200K, and daylight white has a color temperature of 5000K. The lighting device 1400 may have a color filter.

[0165] Furthermore, the lighting device 1400 according to this embodiment may have a heat dissipation unit. The heat dissipation unit dissipates heat from within the device to the outside, and examples of the heat dissipation unit include metal with a high specific heat, liquid silicon, and the like.

[0166] 5B is a schematic diagram of an automobile 1500, which is an example of a moving body according to this embodiment. The automobile 1500 has tail lamps 1501, which are an example of a lighting device. The automobile 1500 may have tail lamps 1501 that are turned on when braking or the like is performed.

[0167] The tail lamp 1501 includes the organic light-emitting element according to this embodiment. The tail lamp may include a protective member for protecting the organic EL element. The protective member may be made of any material as long as it has a certain degree of strength and is transparent, but it is preferably made of polycarbonate or the like. Polycarbonate may also 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 1500. The transparent display has the 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] 6A and 6B , application examples of the display devices according to the above-described embodiments will be described. The display device can be applied to systems that can be worn as wearable devices, such as smart glasses, HMDs, and smart contact lenses. The image capturing and display device used in such application examples includes an image capturing device capable of photoelectrically converting visible light and a display device capable of emitting visible light.

[0171] 6A illustrates glasses 1600 (smart glasses) according to one application example. An imaging device 1602 such as a CMOS sensor or a SPAD is provided on the front side of a lens 1601 of the glasses 1600. Furthermore, a display device according to any of the above-described 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 according to each embodiment. 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. 6B illustrates glasses 1610 (smart glasses) according to one application example. The glasses 1610 include a control device 1612, which is equipped with an imaging device corresponding to the imaging device 1602 and a display device. A lens 1611 includes an optical system for projecting light emitted from the imaging device and the display device within the control device 1612, and an image is projected onto the lens 1611. The control device 1612 functions as a power source for supplying power to the imaging device and the display device, and controls the operation of the imaging device and the display device. The control device may also include a gaze detection unit for detecting the wearer's gaze. Infrared light may be used for gaze detection. The infrared light emitter emits infrared light toward the eyeball of a user gazing at a displayed image. An imaging unit with a light-receiving element detects the reflected light of the emitted infrared light from the eyeball, thereby obtaining an image of the eyeball. By including a reduction unit for reducing light from the infrared light emitter to the display unit in a planar view, degradation of image quality is reduced.

[0174] The gaze of the user relative to the displayed image is detected from an image of the eyeball obtained by capturing infrared light. Any known method can be used for gaze detection using an image of the eyeball. One example is a gaze detection method based on the Purkinje image formed by reflection of irradiated light on the cornea.

[0175] More specifically, gaze detection processing is performed based on the pupil-corneal reflex method, which calculates a gaze vector representing the direction (rotation angle) of the eyeball based on the pupil image and Purkinje image included in the captured image of the eyeball, thereby detecting the user's gaze.

[0176] A display device according to an embodiment of the present invention may have an imaging device having a light receiving element, and may control the image displayed on the display device based on information about the user's line of sight from the imaging device.

[0177] 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.

[0178] 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.

[0179] 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 the image of the eyeball, using as training data an image of the eyeball and the direction in which the eyeball in the image was actually looking. The AI ​​program may be included in the display device, the imaging device, or an external device. If included in the external device, it is transmitted to the display device via communication.

[0180] 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.

[0181] 7A 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 of the present invention. 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.

[0182] 7B and 7C are diagrams showing the 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 is a direction parallel to the axis of the photoconductor and 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. 7B shows a configuration in which the light-emitting units 36 are arranged along the long axis of the photoconductor 27. FIG. 7C shows a configuration different from that shown in FIG. 7B, 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, the light-emitting units 36 are located at positions corresponding to the intervals between the light-emitting units 36 in the first column. That is, multiple light-emitting units 36 are also arranged at intervals in the row direction. 7C can be rephrased as, for example, a grid-like arrangement, a houndstooth arrangement, or a checkerboard pattern. As described above, by using a device using the organic light-emitting element according to this embodiment, it is possible to achieve a display with good image quality and stability even over a long period of time.

[0183] Examples will be described below by giving examples of synthesis of the heterocyclic compound of the present invention and examples of fabrication of an organic light-emitting device, but the present invention is not limited to these examples.

[0184] Example 1 Exemplary compound (13) was synthesized via the following route.

[0185]

[0186] Each step in the above pathway is described in detail below.

[0187] Synthesis of Intermediate 1

[0188]

[0189] 5-Bromopyridine (23.7 g, 150 mmol), 2-bromophenylboronic acid (30.0 g, 150 mmol), tripotassium phosphate (79.6 g, 375 mmol), and anhydrous 1,4-dioxane (400 ml) were added to a 300 ml four-neck flask, and nitrogen bubbling was performed for 1 hour. Tetrakistriphenylphosphine palladium (5.0 g, 4.33 mmol) was then added, and the mixture was heated to reflux. After 22 hours, the reaction was monitored by TLC (developing solvent: n-hexane / ethyl acetate = 2 / 1). Consumption of the raw materials was confirmed, so the reaction solution was returned to room temperature. The solvent was then concentrated, and the insoluble matter was removed by filtration through Celite using heated toluene. The resulting filtrate was concentrated. The brown, transparent viscous mass obtained after concentration solidified after 20 hours. The product was then purified by silica gel column chromatography (diameter 5 cm, silica gel 200 cc, crude 35.5 g, developing solvent: n-hexane / ethyl acetate = 4 / 1 to 2 / 1), concentrated, and dried to obtain 27.85 g (79%) of a light brown solid. １ The analysis was carried out by H-NMR, MS, and TLC.

[0190] １ H-NMR (400MHz, CDCl ３ ) δ9.25 (s, 1H), 8.84 (s, 2H), 7.75-7.73 (m, 1H), 7.46 (td, J = 7.5, 1.1Hz, 1H), 7.35-7.31 (m, 2H) ppm; MS: m / z 237 [M] ＋ Rf=0.23 (n-hexane:ethyl acetate=2:1).

[0191] Synthesis of Intermediate 2

[0192]

[0193] ​In a 500 ml four-neck flask, intermediate 2 (27.0 g, 115 mmol), 3-chlorophenylboronic acid (21.9 g, 140 mmol), and then tripotassium phosphate (61.0 g, 288 mmol) were completely dissolved in distilled water (145 ml) to prepare a 2 M tripotassium phosphate aqueous solution. The prepared aqueous solution was then added to the system, and nitrogen bubbling was performed for 1 hour. Next, tetrakistriphenylphosphine palladium (5.00 g, 4.33 mmol) was added, and the mixture was heated to reflux. After 22 hours, the reaction was monitored by TLC (developing solvent: toluene / ethyl acetate = 5 / 1). Consumption of the raw materials was confirmed, so the reaction solution was returned to room temperature. Next, the mixture was separated (extracted with ethyl acetate, washed with distilled water), and dehydrated over anhydrous magnesium sulfate. The product was then purified by silica gel column chromatography (diameter 8 cm, silica gel 700 cc, crude 42.5 g, developing solvent: toluene / ethyl acetate = 1 / 0 to 0 / 1), concentrated, and dried to obtain 33.8 g (110%) of a brown, transparent viscous substance containing the solvent. １ The analysis was carried out by H-NMR, MS, and TLC.

[0194] １ H-NMR (400MHz, DMSO-d ６ ) δ9.07 (s, 1H), 8.55 (s, 2H), 7.57 (q, J=2.6Hz, 3H), 7.53-7.49 (m, 1H), 7.39-7. 30 (m, 2H), 7.25 (t, J = 1.8Hz, 1H), 7.05 (dt, J = 7.6, 1.5Hz, 1H) ppm; MS: m / z 267 [M] ＋ Rf = 0.20 (toluene:ethyl acetate = 5:1).

[0195] Synthesis of Intermediate 3

[0196]

[0197] ​Intermediate 3 (2.67 g, 10.0 mmol), iron(III) chloride (6.65 g, 40 mmol), sulfuric acid (0.53 ml, 10.0 ml), and dehydrated chloroform (100 ml) were added to a 300 ml four-neck flask and stirred at room temperature. After 22 hours, the reaction was monitored by TLC (developing solvent: toluene / ethyl acetate = 4 / 1). As a result, the consumption of the raw materials was confirmed, and the reaction solution was returned to room temperature. Next, separation (extraction using chloroform, washing using distilled water) and dehydration using anhydrous magnesium sulfate were performed. Next, the product was purified by removing the starting material (developing solvent: chloroform / methanol = 9 / 1), concentrated, and dried to obtain 1.80 g (68%) of a light brown solid. The target product was identified as follows: １ The analysis was carried out by H-NMR, MS, and TLC.

[0198] １ H-NMR (400MHz, CDCl ３ ) δ9.25 (s, 1H), 8.84 (s, 2H), 7.75-7.73 (m, 1H), 7.46 (td, J = 7.5, 1.1Hz, 1H), 7.35-7.31 (m, 2H) ppm; MS: m / z 265 [M] ＋ Rf = 0.35 (toluene:ethyl acetate = 2:1).

[0199] Synthesis of Intermediate 4

[0200]

[0201] ​Intermediate 3 (5.29 g, 20.0 mmol), bis-pinacolatodiboron (7.62 g, 30.0 mmol), potassium acetate (5.89 g, 60.0 mmol), and dehydrated 1,4-dioxane (150 ml) were added to a 300 ml four-neck flask, and nitrogen bubbling was performed for 1 hour. Next, palladium acetate (0.22 g, 1.0 mmol) and 2-dicyclohexylphosphino-2,6-dimethoxybiphenyl (S-Phos) (0.82 g, 2.0 mmol) were added, and the mixture was heated to reflux. After 22 hours, the reaction was monitored by TLC (developing solvent: toluene / ethyl acetate = 3 / 1). Consumption of the raw materials was confirmed, and the reaction solution was then returned to room temperature. Next, the solvent was concentrated, and then insoluble matter was removed by Celite filtration using ethyl acetate. The residue was purified by silica gel column chromatography (diameter 6 cm, silica gel 300 cc, developing solvent: toluene / ethyl acetate = 3 / 1), concentrated, and dried to obtain 4.27 g (61%) of a light brown solid. １ The analysis was carried out by H-NMR, MS, and TLC.

[0202] １ H-NMR (400MHz, CDCl ３ ) δ10.01 (s, 1H), 9.48 (s, 1H), 9.29 (d, J=8.2Hz, 1H), 9.12 (s, 1H), 8.85 (d, J=7.2Hz, 1H), 8. 68-8.66 (m, 1H), 8.18 (d, J = 8.2Hz, 1H), 7.80-7.72 (m, 2H), 1.44 (s, 12H) ppm; MS: m / z 357 [M] ＋ Rf = 0.30 (toluene:ethyl acetate = 3:1).

[0203] Synthesis of Intermediate 5

[0204]

[0205] ​1-Bromo-4-iodobenzene (13.64 g, 48.2 mmol), dibenzothiophene-4-boronic acid (10.00 g, 43.8 mmol), and (6) anhydrous tetrahydrofuran (100 ml) were added to a 200 ml four-neck flask. Potassium carbonate (6.05 g, 43.8 mmol) was then completely dissolved in distilled water (22 ml) to prepare a 2 M potassium carbonate aqueous solution. The prepared aqueous solution was then added to the system, and nitrogen bubbling was performed for 1 hour. Tetrakistriphenylphosphine palladium (2.53 g, 2.19 mmol) was then added, and the mixture was heated to reflux. After 22 hours, the reaction was monitored by TLC (developing solvent: n-hexane / dichloromethane = 3 / 1). Consumption of the raw materials was confirmed, so the reaction solution was returned to room temperature. The mixture was then separated (extracted with dichloromethane, washed with distilled water), dehydrated with anhydrous magnesium sulfate, and filtered through Celite to remove the insoluble matter. The crude product was then removed using heated toluene, concentrated, and dried to obtain 16.47 g. The product was then purified by silica gel column chromatography (diameter 8 cm, silica gel 900 cc, developing solvent: n-hexane / dichloromethane = 19 / 1 to 9 / 1), concentrated, and dried to obtain 9.10 g (63%) of a brown, transparent viscous material. The target product was identified as follows: １ The analysis was carried out by H-NMR, MS, and TLC.

[0206] １ H-NMR (400MHz, CDCl ３ ) δ 8.21-8.16 (m, 2H), 7.88-7.82 (m, 2H), 7.71-7.68 (m, 1H), 7.59-7.54 (m, 2H), 7.51-7.45 (m, 3H), 7.39 (t, J=7.9 Hz, 1H) ppm; MS: m / z 338 [M]+; Rf=0.25 (n-hexane:dichloromethane=9:1).

[0207] Synthesis of Exemplary Compound (13)

[0208]

[0209] ​In a 500 ml four-neck flask, intermediate 4 (2.14 g, 6.0 mmol), intermediate 5 (2.04 g, 6.0 mmol), and anhydrous 1,4-dioxane (60 ml) were added. Then, tripotassium phosphate (3.82 g, 18 mmol) was completely dissolved in distilled water (40 ml) to prepare a 1.35 M aqueous solution of tripotassium phosphate. The prepared aqueous solution was then added to the system, and nitrogen bubbling was performed for 1 hour. Next, trisdibenzylideneacetonepalladium (55 mg, 0.06 mmol) and 2-dicyclohexylphosphino-2,6-dimethoxybiphenyl (50 mg, 0.12 mmol) were added, and the mixture was heated to reflux. After 22 hours, the reaction was monitored by TLC (developing solvent: toluene / ethyl acetate = 3 / 1). Consumption of the raw materials was confirmed, so the reaction solution was returned to room temperature. The mixture was then separated (extracted with dichloromethane, washed with distilled water), and dehydrated over anhydrous magnesium sulfate. The product was then purified by silica gel column chromatography (diameter 6 cm, silica gel 300 cc, developing solvent: toluene / ethyl acetate = 3 / 1), concentrated, and dried to obtain 2.17 g (74%) of a white solid. １ The purity was measured by H-NMR, MS, TLC, and elemental analysis, and was confirmed to be 99.9%.

[0210] １ H-NMR (400MHz, CDCl ３ ) δ9.97 (s, 1H), 9.48-9.45 (m, 1H), 9.41-9.35 (m, 1H), 8.88 (d, J = 1.8Hz, 1H), 8.77-8.73 (m, 1H), 8.67-8.63 (m, 1H), 8.25-8.19 (m , 3H), 8.08 (dd, J=8.6, 1.8Hz, 1H), 7.90-7.82 (m, 3H), 7.78-7.69 (m, 3H), 7.66-7.59 (m, 2H), 7.52-7.46 (m, 2H) ppm; MS: m / z 489 [M] ＋ Rf = 0.28 (toluene:ethyl acetate = 3:1).

[0211] The synthesized exemplary compound (13) was purified by sublimation to obtain exemplary compound (13) with a purity of 99.9%.

[0212] (Examples 2 and 3) 2.0 x 10 －５ ​Under a vacuum of 10 Pa, a 30 nm mixed film was formed by vapor deposition on a synthetic quartz substrate, using the exemplary compound (13) obtained in Example 1 as the host material and RD-11 and RD-10 as guest materials (light-emitting materials). The guest doping concentration was 4% by mass. The formed film was sealed in a sealed tube in a glove box (nitrogen environment) to prevent contact with oxygen and moisture, and used as a sample for molecular orientation evaluation. The molecular orientation of the guest material was measured for the prepared sample using a molecular orientation property measurement device. The degree of molecular orientation (%) of the transition dipole moment of the guest material relative to the substrate was calculated from the order parameter S obtained from the measurement. As a result, the exemplary compound (13): 4% by mass RD-11 showed a molecular orientation degree of 95%, and the exemplary compound (13): 4% by mass RD-10 showed a molecular orientation degree of 92%.

[0213] Compounds A and B shown in Table 1 and compound E shown in Table 3 were synthesized in the same manner as in Example 1, and films were formed in the same manner as in Example 2. Molecular orientation measurements were performed on guest materials RD-11 and RD-10, respectively. The results are shown in Table 4.

[0214] Examples 4 to 11 Exemplary Compound (14), Exemplary Compound (194), Exemplary Compound (61), and Exemplary Compound (156) were synthesized in the same manner as in Example 1, and the molecular orientation of each of the guest materials RD-11 and RD-10 was measured in the same manner as in Example 2. The results are shown in Table 4.

[0215]

[0216] As shown in Table 4, when a heterocyclic compound according to the present invention containing a quinazoline skeleton with a nitrogen atom facing outward was used as a host material, the degree of molecular orientation of the guest material (light-emitting material) was found to be improved. In particular, the degree of molecular orientation of a guest material having a polar group in the ligand was found to be higher than that of a guest material having no polar group in the ligand.

[0217] As described above, the heterocyclic compound according to the present invention has a strong horizontal alignment property and strong interaction with a guest material when used as a host, and can improve the horizontal alignment property of the guest material.

[0218] The present invention is not limited to the above-described embodiments, and various modifications and variations can be made without departing from the spirit and scope of the present invention. Therefore, the following claims are appended to apprise the public of the scope of the present invention.

[0219] This application claims priority based on Japanese Patent Application No. 2023-217622, ​​filed December 25, 2023, the entire contents of which are incorporated herein by reference.

[0220] 2, 21 First electrode 8, 26 Organic light-emitting element 5, 23 Second electrode 18 Transistor 27 Photosensitive member 28 Exposure light source 1200 Electronic device 1201, 1302, 1311, 1312 Display unit 1203 Housing 1300, 1310 Display device 1400 Illumination device 1402 Light source 1404 Optical filter 1405 Light diffusion unit

Claims

1. A heterocyclic compound represented by the following general formula [1], characterized in that the calculated value of the dipole moment is 2.80 or more. (In the general formula [1], CYn is a group represented by the following general formula [2a] or [2b]. In the general formulas [1], [2a], and [2b], R ａ , R ｂ , R ｃ represent a plurality of substituents at each carbon atom constituting each ring structure, and R １１ to R １４ , R ２１ to R ２６ , R ａ , R ｂ , R ｃ are each independently selected from a hydrogen atom, deuterium, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, an amino group, a cyano group, and a silyl group; m is an integer from 1 to 10; X is CRR', SiRR', S, SO, SO ２ , NR, O, Se, PRR', PO, SeO ２ ; the R and the R' are each independently selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a halogen atom; the carbon atoms forming the ring structure may be bonded to adjacent carbon atoms to further form a ring structure; and * represents the bonding position between the general formula [1] and the general formula [2a] or [2b].) 2. The heterocyclic compound according to claim 1, wherein X is S.

3. The said R １１ to R １４ , R ２１ to R ２６ , R ａ , R ｂ , R ｃ The heterocyclic compound according to claim 1, wherein all of R 4. The above R ２１ The heterocyclic compound according to claim 1, wherein R is a methyl group.

5. The heterocyclic compound according to claim 1, wherein m is 1.

6. The heterocyclic compound according to claim 5, wherein CYn is represented by the general formula [2a].

7. The heterocyclic compound according to claim 6, which is represented by the following general formula [3]. (In the general formula [3], R ３１ to R ３４ are each independently selected from a hydrogen atom, deuterium, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, an amino group, a cyano group, and a silyl group.) 8. The R ３１ to R ３４ wherein all of them are hydrogen atoms, and the heterocyclic compound according to claim 7.

9. The heterocyclic compound according to claim 1, wherein the molecular orientation degree of the molecules of the light-emitting material when used as a host material for the light-emitting layer of an organic light-emitting device is 90% or more.

10. A light-emitting ink composition comprising the heterocyclic compound according to any one of claims 1 to 9, a light-emitting material, and a solvent.

11. An organic light-emitting device having a first electrode, a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, wherein the organic compound layer has the heterocyclic compound according to any one of claims 1 to 9.

12. The organic light-emitting device according to claim 11, wherein the organic compound layer has a light-emitting layer, and the light-emitting layer further has the heterocyclic compound and a light-emitting compound having a lowest excited singlet energy smaller than that of the heterocyclic compound.

13. The organic light-emitting device according to claim 12, wherein the light-emitting layer contains an organic compound different from the heterocyclic compound, and the organic compound has a lowest excited triplet energy smaller than that of the heterocyclic compound and larger than that of the light-emitting compound.

14. The organic light-emitting device according to claim 12, wherein the organic compound layer has a first organic compound layer between the light-emitting layer and the second electrode, and the lowest excited triplet energy of the first organic compound layer is higher than that of the light-emitting layer.

15. The organic light-emitting device according to claim 14, wherein the first organic compound layer is composed of a hydrocarbon compound.

16. The organic light-emitting device according to claim 12, wherein the organic compound layer has a second organic compound layer between the light-emitting layer and the first electrode, and the lowest excited triplet energy of the second organic compound layer is higher than that of the light-emitting layer.

17. The organic light-emitting device according to claim 16, wherein the second organic compound layer is composed of a hydrocarbon compound.

18. A display device having a plurality of pixels, wherein at least one of the plurality of pixels has the organic light-emitting element according to claim 11 and a transistor connected to the organic light-emitting element.

19. An imaging device having an optical unit having a plurality of lenses, an imaging element that receives light that has passed through the optical unit, and a display unit that displays an image captured by the imaging element, wherein the display unit has the organic light-emitting element according to claim 11.

20. An electronic device having a display unit having the organic light-emitting element according to claim 11, a housing in which the display unit is provided, and a communication unit provided in the housing and communicating with the outside.

21. A lighting device having a light source having the organic light-emitting element according to claim 11 and a light diffusing unit or an optical filter that transmits light emitted by the light source.

22. A moving body having a lighting fixture having the organic light-emitting element according to claim 11 and a body in which the lighting fixture is provided.

Images