Organic compound and organic light emitting element

Abstract

An organic compound of the present disclosure is represented by a general formula (1). In the general formula (1), R1 to R19 are each a hydrogen atom or any substituent. Ar1 is an aromatic hydrocarbon ring, a heteroaromatic ring, or a combination thereof. Each of the aromatic hydrocarbon ring and the heteroaromatic ring may have a substituent. Ar2 is a hydrogen atom, a deuterium atom, an aromatic hydrocarbon ring, or a combination of aromatic hydrocarbon rings. Each of the aromatic hydrocarbon ring and the heteroaromatic ring may have a substituent. n represents 0 or 1.

Description

Organic compounds and organic light-emitting devices

[0001] This invention relates to organic compounds and organic light-emitting devices using the same.

[0002] An organic light-emitting element (hereinafter sometimes referred to as an "organic electroluminescent element" or "organic EL element") is an electronic element having a pair of electrodes and an organic compound layer placed between these electrodes. By injecting electrons and holes from this pair of electrodes, excitons of the light-emitting organic compound in the organic compound layer are generated, and when these excitons return to the ground state, the organic light-emitting element emits light.

[0003] Recent advances in organic light-emitting devices are remarkable, enabling low drive voltage, diverse emission wavelengths, fast response times, and miniaturization and weight reduction of light-emitting devices.

[0004] As for compounds created to date, compound 1-a is described in Patent Document 1. Also, compound 2-a is described in Patent Document 2.

[0005]

[0006] Chinese Patent Application Publication No. 114478588, Specification, Japanese Patent Publication No. 2014-214148

[0007] However, compound 1-a described in Patent Document 1 had high molecular symmetry, which meant there was room for improvement in terms of luminescence efficiency. Similarly, compound 2-a described in Patent Document 2 also had room for improvement in terms of luminescence efficiency.

[0008] Therefore, the present invention has been made in view of the above problems, and its purpose is to provide an organic compound with excellent luminescence efficiency.

[0009] The organic compound according to the present invention is characterized by being represented by general formula (1).

[0010]

[0011] In general formula (1), R １ ~R １９Each of these is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, and a cyano group.

[0012] Ar １ This is an aromatic hydrocarbon ring, a heteroaromatic ring, or a combination thereof. The aromatic hydrocarbon ring and the heteroaromatic ring may have substituents.

[0013] Ar ２ This is a hydrogen atom, a deuterium atom, an aromatic hydrocarbon ring, or a combination of aromatic hydrocarbon rings. The aromatic hydrocarbon ring and the heteroaromatic ring may have substituents.

[0014] n is either 0 or 1.

[0015] According to the present invention, it is possible to provide an organic compound with excellent luminescence efficiency.

[0016] This is a schematic cross-sectional view showing an example of a pixel in a display device according to one embodiment of the present invention. This is a schematic cross-sectional view showing an example of a display device using an organic EL element according to one embodiment of the present invention. This is a schematic diagram showing an example of a display device according to one embodiment of the present invention. This is a schematic diagram showing an example of an imaging device according to one embodiment of the present invention. This is a schematic diagram showing an example of an electronic device according to one embodiment of the present invention. This is a schematic diagram showing an example of a display device according to one embodiment of the present invention. This is a schematic diagram showing an example of a foldable display device. This is a schematic diagram showing an example of a lighting device according to one embodiment of the present invention. This is a schematic diagram showing an example of an automobile having vehicle lighting fixtures according to one embodiment of the present invention. This is a schematic diagram showing an example of an automobile having vehicle lighting fixtures and a display unit according to one embodiment of the present invention. This is a schematic diagram showing an example of a wearable device according to one embodiment of the present invention. This is a schematic diagram showing an example of a wearable device according to one embodiment of the present invention, with an imaging device. This is a schematic diagram showing an example of an image forming apparatus according to one embodiment of the present invention. This is a schematic diagram showing an example of an exposure light source for an image forming apparatus according to one embodiment of the present invention. This is a schematic diagram showing an example of an exposure light source for an image forming apparatus according to one embodiment of the present invention. These are the HOMO orbital distributions and LUMO orbital distributions of exemplary compounds A7 and A17.

[0017] In this specification, halogen atoms include, but are not limited to, fluorine, chlorine, bromine, iodine, astatine, and tennessine.

[0018] The alkyl group may be an alkyl group having 1 to 20 carbon atoms, or an alkyl group having 1 to 10 carbon atoms. Specifically, examples include, but are not limited to, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, secondary butyl group, octyl group, cyclohexyl group, tert-pentyl group, 3-methylpentan-3-yl group, 1-adamantyl group, and 2-adamantyl group.

[0019] The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms. Specifically, examples include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, an isopropyl group, a tertiary hydroxy group, a 2-ethyl octyloxy group, a benzyloxy group, etc.

[0020] A silyl group is a group in which a silicon atom has a substituent. The substituent may be a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The substituted or unsubstituted alkyl group on the silicon atom may be a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. The substituted or unsubstituted aryl group on the silicon atom may be a substituted or unsubstituted aryl group having 6 to 10 carbon atoms. The silyl group may be a trialkylsilyl group or a triarylsilyl group. Specifically, examples include, but are not limited to, a trimethylsilyl group and a triphenylsilyl group.

[0021] The aryl group may be an aryl group having 6 to 20 carbon atoms, an aryl group having 6 to 18 carbon atoms, or an aryl group having 6 to 12 carbon atoms. Specifically, examples include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthrenyl, triphenylenyl, indenyl, terphenyl, fluorenyl, pyrenyl, anthranyl, perilenyl, chrysenyl, and fluoranthenyl groups.

[0022] The heteroaryl group may be a heteroaryl group having 3 to 24 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, or a heteroaryl group having 3 to 12 carbon atoms. Specifically, examples include, but are not limited to, pyridyl, pyrimidyl, pyrazyl, triazyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, carbazolyl, acridinyl, and phenanthrolyl groups.

[0023] The amino group may be a substituted amino group substituted with an alkyl group or an aryl group, and may be a substituted amino group substituted with an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms. Specifically, examples include, but are not limited to, N-methylamino group, N-ethylamino group, N,N-dimethylamino group, N,N-diethylamino group, N-methyl-N-ethylamino group, N-benzylamino group, N-methyl-N-benzylamino group, N,N-dibenzyloamino group, anilino group, N,N-diphenylamino group, N,N-dinaphthylamino group, N,N-difluorenylamino group, N-phenyl-N-tolylamino group, N,N-ditolylamino group, N-methyl-N-phenylamino group, N,N-dianisorylamino group, N-mesityl-N-phenylamino group, N,N-dimesitylamino group, N-phenyl-N-(4-tert-butylphenyl)amino group, N-phenyl-N-(4-trifluoromethylphenyl)amino group, N-piperidyl group, etc.

[0024] Examples of aryloxy groups include, but are not limited to, phenoxy groups.

[0025] Examples of heteroaryloxy groups include, but are not limited to, thienyloxy groups.

[0026] Examples of substituents that the alkyl, alkoxy, amino, aryloxy, silyl, aryl, heteroaryl, and heteroaryloxy groups may further have include, but are not limited to, deuterium, alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl groups, aralkyl groups such as benzyl groups, aryl groups such as phenyl and biphenyl groups, heterocyclic groups such as pyridyl and pyrrolyl groups, amino groups such as dimethylamino, diethylamino, dibenzylamino, diphenylamino, and ditolylamino groups, alkoxy groups such as methoxy, ethoxy, and propoxy groups, aryloxy groups such as phenoxy groups, halogen atoms such as fluorine, chlorine, bromine, and iodine, and cyano groups.

[0027] (1) Organic Compounds The organic compound according to the present invention is an organic compound represented by general formula (1).

[0028]

[0029] In general formula (1), R １ ~R １９ Each of these is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, and a cyano group.

[0030] Ar １ This is an aromatic hydrocarbon ring, a heteroaromatic ring, or a combination thereof. The aromatic hydrocarbon ring and the heteroaromatic ring may have substituents.

[0031] Ar ２It is a hydrogen atom, a deuterium atom, an aromatic hydrocarbon ring, or a combination of aromatic hydrocarbon rings. The aromatic hydrocarbon ring and the heteroaromatic ring may have substituents.

[0032] n is 0 or 1.

[0033] <R １ to R １９ > R １ to R １９ may each independently be selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 4 carbon atoms, and a trimethylsilyl group. Specifically, R １ to R １９ may each independently be selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a CD ３ group, an iso - propyl group, a tert - butyl group, a cyclohexyl group, a methoxy group, and a trimethylsilyl group.

[0034] Also, R ３ and R ６ may be a hydrogen atom, R １ to R １９ may be a hydrogen atom, and R １ to R １９ may be a deuterium atom.

[0035] Here, when at least one of R １ to R １７ is a substituent other than a hydrogen atom, at least one of R ３ [[ID=4」]] R ５ R ６ R １２ or R １６ may be a substituent, and at least one of R ３ and R ５ R ６ or R " １２ and R １６ may be substituents.

[0036] " Also, Ar １ is bonded by any of R １１ to R １９ but R １３ R１６ , or R １９ It is preferable that they be bonded in one of the following ways, R １９ It is even more preferable to join them with Ar. Here, for example, Ar １ R １９ To combine with R １９ Ar is bonded to the carbon atom. １ This refers to a direct bond between the two, specifically, to being represented by the general formula (1-2). The organic compound according to this embodiment is preferably represented by the general formula (1-2).

[0037]

[0038] <Ar １ > The organic compound according to the present invention is Ar １ When it has (n is 1), Ar １ This may be an aromatic hydrocarbon ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 15 carbon atoms, or a combination thereof.

[0039] Also, Ar １ This may be an aromatic hydrocarbon ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 15 carbon atoms, a combination of an aromatic hydrocarbon ring having 6 to 10 carbon atoms and a heteroaromatic ring having 3 to 9 carbon atoms, a combination of an aromatic hydrocarbon ring having 6 to 10 carbon atoms and an aromatic hydrocarbon ring having 6 to 10 carbon atoms, or a combination of a heteroaromatic ring having 3 to 9 carbon atoms and a heteroaromatic ring having 3 to 9 carbon atoms. Specifically, this may be a benzene ring, a phenanthrene ring, a triphenylene ring, a chrysene ring, a spirofluorene ring, a fluorene ring, a pyridine ring, a thiophene ring, a furan ring, a dibenzofuran ring, a dibenzothiophene ring, a quinoline ring, a combination of two benzene rings (biphenyl group), a combination of a naphthalene ring and a benzene ring, a combination of two thiophene rings, a combination of a benzene ring and a pyridine ring, a combination of a benzene ring and an oxazole ring, or a combination of a benzene ring and a thiazole ring.

[0040] Also, Ar １This may be an aromatic hydrocarbon ring having 6 to 25 carbon atoms, a heteroaromatic ring having 3 to 12 carbon atoms, a combination of an aromatic hydrocarbon ring having 6 to 10 carbon atoms and a heteroaromatic ring having 3 to 5 carbon atoms, a combination of an aromatic hydrocarbon ring having 6 to 10 carbon atoms and an aromatic hydrocarbon ring having 6 to 10 carbon atoms, or a combination of a heteroaromatic ring having 3 to 5 carbon atoms and a heteroaromatic ring having 3 to 5 carbon atoms.

[0041] Also, Ar １ This may be an aromatic hydrocarbon ring having 5 to 15 carbon atoms or a heteroaromatic ring having 3 to 12 carbon atoms. Specifically, it may be a benzene ring, a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, or a fluorene ring, and is preferably a benzene ring, a dibenzofuran ring, a dibenzothiophene ring, or a fluorene ring.

[0042] Ar １ If the substituent has substituents, the substituent may be a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, or a cyano group. Preferably, it is a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms, and more preferably, it is a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 10 carbon atoms. Specifically, it is preferably one or more methyl groups or phenyl groups, and more preferably, it is one or more methyl groups.

[0043] Ar １ is, sp ３ The number of carbon atoms is less than sp ２ A large number of carbon atoms is preferable, sp ２ It is more preferable that it consists only of carbon. Furthermore, Ar １ If the benzene ring is included, it is preferable that the benzene ring has bonding positions with the indolocarbazole ring and the pyrene ring at the meta or para position, and it is even more preferable that it has bonding positions with the indolocarbazole ring and the pyrene ring at the para position.

[0044] <Ar ２ > Ar ２ This may be an aromatic hydrocarbon ring having 6 to 30 carbon atoms, an aromatic hydrocarbon ring having 6 to 18 carbon atoms, or an aromatic hydrocarbon ring having 6 to 15 carbon atoms. Specifically, it may be a benzene ring, a naphthalene ring, a spirofluorene ring, a chrysene ring, a triphenylene ring, or a fluorene ring, and may be a benzene ring, a triphenylene ring, or a fluorene ring. Also, Ar ２ This may be a benzene ring, or a combination of benzene rings (biphenyl group).

[0045] Ar ２ When is an aromatic hydrocarbon ring, the aromatic hydrocarbon ring may have substituents. The substituents may be a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms. Specifically, a deuterium atom, a phenyl group, a phenyl group having a deuterium atom, a naphthyl group, a phenyl group having a tert-butyl group, one or more methyl groups, one or more iso-propyl groups, a tert-butyl group, a tert-butyl group having a deuterium atom, a triphenylene group, a cyclohexyl group, or CD ３ It may be a phenyl group having a group.

[0046] Also, Ar ２ This may be a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms. Specifically, it may be a deuterium atom, a phenyl group, a naphthyl group, a phenyl group having an alkyl group having 1 to 4 carbon atoms, one or more methyl groups, a tert-butyl group having a deuterium atom, a triphenylene group, or a triphenylene group having a phenyl group.

[0047] Also, Ar ２This may be a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms. Specifically, it may be a deuterium atom, a phenyl group, a phenyl group having a tert-butyl group, one or more methyl groups, or a triphenylene group.

[0048] Also, Ar ２ This may be a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, or a phenyl group having an alkyl group having 3 or 4 carbon atoms. Specifically, it may be a phenyl group having a deuterium atom, one or more methyl groups, or a tert-butyl group.

[0049] Also, Ar ２ It does not need to have substituents.

[0050] <n> n is 0 or 1, and it is preferable that n is 0. In other words, it is preferable that the indolocarbazole skeleton and the pyrene skeleton are directly bonded.

[0051] The following describes the structure of the organic compound according to this embodiment. (1-1) Because it has an indolocarbazole skeleton and a pyrene skeleton, the permanent dipole moment of the molecule is improved.

[0052] The following provides a detailed explanation of this configuration.

[0053] (1-1) The organic compound according to this embodiment has an indolocarbazole skeleton and a pyrene skeleton, which increases the permanent dipole moment of the molecule, and therefore has excellent luminescence efficiency.

[0054] The organic compound according to this embodiment has a pyrene skeleton, with one end being an indolocarbazole skeleton which is a heteroaromatic ring, and the other end being a combination of a hydrogen atom, a deuterium atom, an aromatic hydrocarbon ring, or an aromatic hydrocarbon ring. Therefore, the entire molecule has a structure in which one end is an indolocarbazole skeleton which is a heteroaromatic ring, and the other end is a hydrocarbon. In this way, the organic compound according to this embodiment exhibits excellent luminescence efficiency because polarization occurs within the molecule, resulting in a high permanent dipole moment.

[0055] Table 1 shows schematic diagrams of the quench with respect to the charge within the light-emitting element when using exemplary compound A9, an organic compound according to this embodiment, and comparative example compound 1-a. Here, the luminous efficiency is a relative value when the luminous efficiency of the organic compound of comparative example 1 is set to 1.0.

[0056]

[0057] In example compound A9, an organic compound according to this embodiment shown in Table 1, when an exciton is generated at the center of the molecule, electrons (anions) and holes (cations) approaching the molecule move towards the δ+ and δ- regions, respectively. As a result, since the exciton is located in a region far from the electrons and holes, the deactivation (quenching) of the exciton by electrons and holes can be suppressed, and an organic light-emitting element with excellent luminescence efficiency can be provided.

[0058] Here, we will explain the effect of increasing the distance between the location where excitons are generated and the location where electrons or holes approach. If an exciton approaches an electron or hole within a certain distance before it transitions to the ground state, the exciton quenches, reducing its luminescence efficiency. Therefore, to suppress exciton quenching, it is necessary to increase the distance between the location where excitons are generated and the location where electrons or holes approach the molecule. In the organic compound according to this embodiment, the intramolecular polarization is large, so electrons or holes approach a location far from the center of the molecule. As a result, the exciton generated at the center of the molecule moves away from the electron or hole, thus suppressing exciton quenching.

[0059] On the other hand, compound 1-a has low intramolecular polarization, and when an exciton is generated at the center of the molecule, electrons and holes are more likely to approach that exciton. Therefore, it is a compound that is more prone to quenching compared to the organic compound according to this embodiment. For this reason, it is thought that the organic light-emitting device using compound 1-a showed a low luminescence efficiency.

[0060] The organic compound according to this embodiment preferably has a permanent dipole moment of 0.4 or more, and more preferably 0.5 or more. Furthermore, the organic compound according to this embodiment may have a permanent dipole moment of 1.0 or less, 0.8 or less, or 0.7 or less.

[0061] The permanent dipole moments in Table 1 were calculated using molecular orbital calculations. The molecular orbital calculation method used was the widely used density functional theory (DFT). The functional was B3LYP, and the basis set was 6-31G. ＊Thanks for watching, it's a nice place to stayるfingernail nine(fingernail nine,six THIS 01, 100,000,000 THIS, CHASE, CHASE Yes, ROCKS, ROCKS feelings ,ShanaShana,ShaShanaSay,MYS The smile, the smile, the smile The smile, the smile, the snake snowflake, snowflake, snow Yes, scientists, scientists, THIS, THIS IS, THIS IS, THIS. The snow, the smile, the smile, THIS IS YOU, YOU, YOU ANNAI, THIS THING, THIS THING snow,20,000,000,000 Thanks, smile, CHAN,D FAMILIES, POPE, SHYS Emotional, scientific, scientific Yes, I love you, I love you FASHIONS,DASHATHING,WAYS Thanks, smile, smile,. THIS, THIS IS YOUR LIFE, THIS THIS, THIS IS, THIS IS, THIS, THIS IS YOUR LIFE, THIS THIS IS YOUR FAVORITE, YOUR FAVORITE, ASHABITA,ACHARIS,CHARAS Yes, I love it, I love it CHARIGHTY, CHATHARIC EXPERIENCE, ANOTHER THINGS, THIS THINGS, THIS smile, smile, smile It is, scientific, scientific AND YOUTH, THIS THINGS, THIS FAIR, THIS, THIS, THIS IS YOUR LIFE THIS,20100) is the best place to stay Thanks for watching, it's a nice smile.

[0062] One of the ingredients is a slightly less expensive scent with a slightly less expensive scent.

[0063] Furthermore, the organic compound according to this embodiment has the following configuration: (1-2) Intermolecular stacking is suppressed because the molecule has an asymmetric structure; (1-3) It is bonded to the nitrogen atom of indolocarbazole at the meta position with pyrene.

[0064] The following describes these configurations.

[0065] (1-2) Intermolecular stacking is suppressed because the molecule has an asymmetric structure. Because the organic compound according to this embodiment has an asymmetric structure, intermolecular stacking can be suppressed. Therefore, the organic compound according to this embodiment is less likely to crystallize in the film, and as a result, it can exhibit excellent luminescence efficiency.

[0066] Here, we will explain the effects of using an organic compound that is difficult to crystallize. By using an organic compound that is difficult to crystallize, the film quality becomes more uniform. When an organic compound is difficult to crystallize, the formation of grain boundaries, trap levels, and quenchers associated with minute crystals is less likely to occur, and energy transfer from the host material to the guest material becomes easier. As a result of easier energy transfer, an organic light-emitting element with excellent luminescence efficiency can be provided. In other words, by suppressing energy transfer to quenchers, an organic light-emitting element with excellent luminescence efficiency can be provided. Therefore, the organic compound according to this embodiment has excellent luminescence efficiency.

[0067] Furthermore, because the organic compound is less prone to crystallization, it is possible to reduce the quenchers generated by the decomposition or intermolecular reactions of excited molecules. As a result, it is possible to provide an organic light-emitting element with excellent durability. Therefore, the organic compound according to this embodiment also has excellent durability.

[0068] On the other hand, compound 1-a has a highly symmetrical structure because the pyrene skeleton is sandwiched between two indolocarbazole skeletons. As a result, compound 1-a is prone to crystallization, which leads to low luminescence efficiency and poor durability.

[0069] Table 2 shows the glass transition temperature (Tg) and permanent dipole moment of the organic compound and compound 1-a according to this embodiment, as well as the luminous efficiency ratio and durability ratio of the organic light-emitting device using the organic compound and compound 1-a according to this embodiment. The luminous efficiency ratio is calculated at a current density of 100 mA / cm². ２ The external quantum efficiency (EQE) was measured and is shown as a ratio when the efficiency of the device in Comparative Example 1 is set to 1.0. The durability ratio is calculated using a current density of 100 mA / cm². ２ A continuous operation test was conducted, and the brightness was measured after 100 hours. The results are shown as a ratio when the brightness of the element in Comparative Example 1 is set to 1.0.

[0070]

[0071] Table 2 shows that the Tg of the exemplary organic compound according to this embodiment was 130°C or higher, while the Tg of comparative example compound 1-a was undetectable. This is thought to be because the organic compound according to this embodiment has an asymmetric molecular structure, making it difficult for the organic compound to crystallize. As a result, the luminous efficiency ratio and durability of the organic light-emitting device using the organic compound according to this embodiment were superior to those of the organic light-emitting device using compound 1-a.

[0072] (1-3) The organic compound according to this embodiment, which is bonded to the nitrogen atom of indolocarbazole at the meta position with pyrene, has a low HOMO (far from the vacuum level) due to the bond with pyrene at the meta position with respect to the nitrogen atom of indolocarbazole, and therefore exhibits excellent durability.

[0073] In a benzene ring having a carbon-nitrogen bond, the electron-donating ability of the meta position to the nitrogen atom is smaller than that of the para position. Therefore, when a substituent is present at the meta position to the nitrogen atom, the HOMO is lower compared to when the substituent is present at the para position. As a result, the organic compound according to this embodiment has excellent oxidation stability and thus excellent durability.

[0074] Table 3 shows the HOMO and endurance ratios of example compound A9 and compounds 2-a and 2-b.

[0075]

[0076] Table 3 shows that the HOMO of example compound A9 was lower than that of compounds 2-a and 2-b. This is thought to be because example compound A9 has pyrene bonded to the meta position relative to the nitrogen atom of indolocarbazole, resulting in a lower HOMO value.

[0077] Therefore, the organic compound according to this embodiment has a low HOMO and is an organic compound with excellent oxidative stability.

[0078] As described above, the organic compound according to this embodiment has the configurations of (1-1) and (1-2), and therefore is an organic compound with excellent luminescence efficiency. Furthermore, the organic compound according to this embodiment has the configurations of (1-2) and (1-3), and therefore is an organic compound with excellent durability.

[0079] Furthermore, the organic compound according to this embodiment preferably has the following configuration. These configurations may be present individually or in multiples. (1-4) A single bond that can freely rotate is sp ２ In general formula (1) (1-5), which consists of carbon-carbon bonds, Ar １ and Ar ２ (1-6) The organic compound according to this embodiment is used together with a luminescent material consisting only of hydrocarbons. (1-7) The hole block layer (HBL) is made of a compound consisting only of hydrocarbons.

[0080] The following describes these features.

[0081] (1-4) A single bond that can rotate freely is sp ２ The organic compound according to this embodiment, which consists of carbon-carbon bonds, is preferable because the freely rotatable single bonds consist of sp2 carbon-carbon bonds, resulting in high bond energy and improved durability.

[0082] In this specification, a freely rotatable single bond refers to a bond between unit A and unit B that is not ring-fused, where unit A and unit B are represented as "A-B". Units A and B may be atoms such as carbon atoms or nitrogen atoms, or molecules such as benzene or carbazole.

[0083] In organic light-emitting devices, the organic compound layer, particularly the compounds in the light-emitting layer, repeatedly transitions between the ground state and the excited state during the light emission process. This process involves vigorous molecular stretching, rotation, and other dynamic movements. If there are sites where bonds are easily dissociated, these bonds can break, releasing some of the compound. Since the release of a portion of the compound alters its structure, organic light-emitting devices using compounds with easily dissociated sites tend to have lower durability. Furthermore, when such compounds are used in organic light-emitting devices, the released portions act as quenchers, reducing luminescence efficiency. Therefore, molecules with structures that are less prone to bond dissociation and release exhibit superior durability and luminescence efficiency.

[0084] In this embodiment, all freely rotating single bonds are sp ２ Because the compound consists of carbon-carbon bonds, liberation due to bond cleavage is less likely to occur, resulting in an organic compound with superior durability and luminous efficiency. Therefore, when the organic compound according to this embodiment is used in the organic compound layer of an organic light-emitting device, an organic light-emitting device with superior durability and luminous efficiency can be obtained.

[0085] (1-5) In general formula (1), Ar １ and Ar ２ In this embodiment, the organic compound is either a phenyl group or a biphenyl group, or n is 0, and in general formula (1), Ar １ and Ar ２ The presence of a phenyl group, a biphenyl group, or n=0 increases the π-conjugated region within the entire molecule, resulting in faster electron mobility and suppressed exciton quenching. As a result, it is preferable to have an organic compound with superior luminescence efficiency and durability.

[0086] Figure 8 shows the HOMO and LUMO orbital distributions of example compounds A9 and A17. From Figure 8, it can be seen that the HOMO and LUMO orbitals of example compounds A9 and A17 are distributed in the region indicated by the dotted line in Figure 8. Therefore, Ar １ and Ar ２When is a phenyl group or a biphenyl group, or when n is 0, regions where HOMO and LUMO are not distributed within the molecule are less likely to be formed, and therefore the carrier mobility tends to be high. Therefore, in the organic compound according to this embodiment, Ar １ and Ar ２ The organic compound is obtained when n is a phenyl group or a biphenyl group, or when n is 0, resulting in an organic compound with superior luminescence efficiency and durability. The organic compound according to this embodiment is Ar ２ It is more preferable that n is a phenyl group or a biphenyl group, or that n is 0.

[0087] (1-6) When the organic compound according to this embodiment is used in an organic light-emitting device, it is preferable that the organic compound layer of the organic light-emitting device has the organic compound according to this embodiment and a light-emitting material whose basic skeleton is composed solely of hydrocarbons. Specifically, it is preferable that the light-emitting layer in the organic compound layer has the organic compound according to this embodiment and a light-emitting material whose basic skeleton is composed solely of hydrocarbons. Details of the configuration of the organic light-emitting device will be described later.

[0088] Here, the basic skeleton of the luminescent material refers to the skeleton with the largest number of rings constituting the fused ring structure among the fused ring structures of the luminescent material. For example, if the luminescent material consists of a pyrene skeleton (4 rings) and a perylene skeleton (5 rings), the perylene skeleton becomes the basic skeleton. The basic skeleton may have substituents, and these substituents include a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted amino group, or a cyano group. Among these, it is preferable that the substituents be a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted amino group, or a cyano group; more preferably a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; and even more preferably a deuterium atom, an alkyl group, or an aryl group.

[0089] In the organic light-emitting element according to this embodiment, the low polarization of the light-emitting material makes it less likely to interact with the host material compared to the case where the polarization of the light-emitting material is high. As a result, the effect of improving the luminescence efficiency by the host material as described above can be obtained more effectively. For this reason, it is preferable that the light-emitting material according to this embodiment consists only of hydrocarbons as its basic skeleton, and it is more preferable that the basic skeleton and the substituents on the basic skeleton consist only of hydrocarbons.

[0090] (1-7) When an organic light-emitting device using an organic compound according to this embodiment, in which the hole blocking layer (HBL) is a compound consisting solely of hydrocarbons, has an organic compound layer comprising an HBL and a light-emitting layer, it is preferable that the material constituting the HBL is a light-emitting material consisting solely of hydrocarbons. Specifically, it is preferable that the HBL in the organic compound layer is made of a material whose basic skeleton consists solely of hydrocarbons (the material constituting the HBL). In this case, it is preferable that the HBL and the light-emitting layer are adjacent to each other. Details of the configuration of the organic light-emitting device will be described later.

[0091] Here, the basic skeleton of the material constituting the HBL refers to the skeleton with the largest number of rings constituting the fused ring structure among the fused ring structures possessed by the material constituting the HBL. For example, if the material constituting the HBL consists of a pyrene skeleton (4 rings) and a perylene skeleton (5 rings), the perylene skeleton becomes the basic skeleton. The basic skeleton may have substituents, and these substituents include a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryloxy group, a substituted or unsubstituted amino group, or a cyano group. Among these, it is preferable that the substituent is a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted amino group, or a cyano group; more preferably that it is a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group; and even more preferably that it is a deuterium atom, an alkyl group, or an aryl group.

[0092] In the organic light-emitting element according to this embodiment, the small polarization of the material constituting the HBL makes it less likely to interact with the host material of the light-emitting layer compared to the case where the polarization of the material constituting the HBL is large. As a result, the effect of improving the luminescence efficiency by the host material as described above can be obtained more effectively. For this reason, it is preferable that the material constituting the HBL according to this embodiment consists only of hydrocarbons as its basic skeleton, and it is more preferable that the basic skeleton and the substituents on the basic skeleton consist only of hydrocarbons.

[0093] Specific examples of organic compounds according to this embodiment are shown below. However, this embodiment is not limited to these examples.

[0094]

[0095]

[0096]

[0097] The example compounds belonging to group A are those whose entire molecule is sp ２ It is a compound composed of carbon atoms. Therefore, among the organic compounds according to this embodiment, it is an organic compound with particularly excellent durability.

[0098] Examples of compounds belonging to group B include Ar １ Ar ３ , and Ar ５ This compound has a heteroaromatic ring. Therefore, charge transport properties are improved, and in particular, organic light-emitting devices with low voltages can be obtained.

[0099] The exemplary compounds belonging to group C are compounds having an alkyl group, a silyl group, or a spirofluorene ring. Therefore, the organic compounds according to this embodiment are bulky and can reduce intermolecular stacking, making them organic compounds with particularly excellent luminescence efficiency.

[0100] (2) Organic Light-Emitting Device Next, an organic light-emitting device according to one embodiment of the present invention will be described. The organic light-emitting device according to one embodiment of the present invention has 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. In the organic light-emitting device according to this embodiment, the organic compound layer may be a single layer or a laminate consisting of multiple layers, provided that it has a light-emitting layer. The organic compound according to the present invention may be contained in the organic compound layer, and preferably it is contained in the light-emitting layer. Here, if the organic compound layer is a laminate consisting of multiple layers, the organic compound layer may have 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., in addition to the light-emitting layer. The light-emitting layer may be a single layer or a laminate consisting of multiple layers. If there are multiple light-emitting layers, a charge generation layer may be provided between the light-emitting layers. The charge generation layer may be composed of a compound whose LUMO (Lowest Unoccupied Molecular Orbital) energy level is lower than the HOMO energy level of the hole transport layer, and the LUMO energy level of the charge generation layer may be lower than the HOMO energy level of the hole transport layer. Here, the HOMO and LUMO energy levels of the organic compound layer may be those of the organic compound with the largest weight ratio in the organic compound layer.

[0101] Specific element configurations of the organic light-emitting element according to this embodiment include multilayer element configurations in which electrode layers and organic compound layers shown in (1) to (6) below are sequentially stacked on a substrate. (1) Anode / light-emitting layer / cathode (2) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode (3) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode (4) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode (5) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode (6) Anode / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0102] However, these examples of element configurations are merely very basic and are not limited to them. For example, a variety of layer configurations can be adopted, such as providing an insulating layer, adhesive layer, or interference layer at the interface between the electrode and the organic compound layer, having an electron transport layer or hole transport layer composed of two layers with different ionization potentials, or having a light-emitting layer composed of two layers of different light-emitting materials.

[0103] In the device configurations shown in (1) to (6) above, configuration (6) is preferred because it has both an electron blocking layer and a hole blocking layer. In other words, in configuration (6) which has both an electron blocking layer and a hole blocking layer, both hole and electron carriers can be reliably confined within the light-emitting layer, resulting in an organic light-emitting element with no carrier leakage and high light-emitting efficiency.

[0104] The method of extracting light from the light-emitting layer (device configuration) can be either a so-called bottom emission method, where light is extracted from the electrode on the substrate side, or a so-called top emission method, where light is extracted from the opposite side of the substrate. A double-sided extraction method, where light is extracted from both the substrate side and the opposite side of the substrate, can also be employed.

[0105] Here, the HOMO energy level and LUMO energy level are described as "higher" the closer they are to the vacuum level. When the LUMO energy level of the charge generation layer is lower than the HOMO energy level of the hole transport layer, it means that the LUMO energy level of the charge generation layer is further from the vacuum level than the HOMO energy level of the hole transport layer.

[0106] In this specification, the HOMO energy level and the LUMO energy level can be calculated using molecular orbital calculations.

[0107] In this specification, the HOMO energy level and LUMO energy level can also be calculated using the ionization potential and band gap. The HOMO energy level can be estimated by measuring the ionization potential. The ionization potential can be measured using a measuring device such as AC-3 after dissolving the compound to be measured in a solvent such as toluene or after creating a vapor-deposited film of the compound on a substrate such as glass. The band gap can be measured by dissolving the compound to be measured in a solvent such as toluene and irradiating it with excitation light. The band gap can be measured by measuring the absorption edge of the absorption spectrum of the excitation light. Alternatively, the compound to be measured can be vapor-deposited on a substrate such as glass and the vapor-deposited film can be irradiated with excitation light. The measurement can be performed by measuring the absorption edge of the absorption spectrum of the vapor-deposited film that absorbs the excitation light.

[0108] The LUMO energy level can be calculated using the band gap and ionization potential. By subtracting the ionization potential from the band gap, the LUMO energy level can be estimated.

[0109] The LUMO energy level can also be estimated from the reduction potential. For example, the one-electron reduction potential can be estimated using cyclic volmetry (CV) measurement. CV measurement is performed, for example, in a 0.1 M tetrabutylammonium perchlorate DMF solution, with an Ag / Ag reference electrode. ＋ The measurement can be performed using Pt as the counter electrode and glassy carbon as the working electrode. The LUMO energy level can be estimated by adding the difference between the reduction potential of the obtained compound and the reduction potential of ferrocene, which is -4.8 eV.

[0110] In an organic light-emitting element according to one embodiment of the present invention, if the organic compound according to the present invention is included in the light-emitting layer, the light-emitting layer may consist only of the organic compound according to the present invention, or it may consist of the organic compound according to the present invention and other compounds. Here, if the light-emitting layer is a layer consisting of the organic compound according to the present invention and other compounds, the organic compound according to the present invention may be used as a host material for the light-emitting layer, or as a guest material. It may also be used as an assist material that can be included in the light-emitting layer. Here, the host material is also called the "host" or "first compound," and is the compound with the largest mass ratio among the compounds constituting the light-emitting layer. The guest material is also called the "guest," "dopant material," "dopant," or "third compound," and is a compound with a smaller mass ratio than the host among the compounds constituting the light-emitting layer, and is the compound that is primarily responsible for light emission. For this reason, the guest material is sometimes also called the light-emitting material. The assist material is also called the "assist" or "second compound," and is a compound with a smaller mass ratio than the host material among the compounds constituting the light-emitting layer, and assists the light emission of the guest material. The assist material is also called the second host.

[0111] Here, let S1(H) be the lowest singlet excitation energy of the host material, S1(D) be the lowest singlet excitation energy of the guest material, and S1(A) be the lowest singlet excitation energy of the assist material. The guest material may be considered to be an organic compound according to the present invention. In this case, it is preferable that the organic light-emitting element according to this embodiment satisfies S1(H) > S1(D) or S1(H) > S1(A) > S1(D). By satisfying the above relationship between the lowest singlet excitation energy of the compound included in the organic light-emitting element according to this embodiment, excitons can be efficiently transferred to the guest material, resulting in an organic light-emitting element with superior luminescence efficiency.

[0112] When the organic compound according to the present invention is used as a host material for the light-emitting layer, the concentration of the host material may be 50% by mass or more and less than 99% by mass relative to the entire light-emitting layer, preferably 50% by mass or more and 98% by mass or less, more preferably 50% by mass or more and 95% by mass or less, and even more preferably 50% by mass or more and 90% by mass or less.

[0113] When the light-emitting layer further comprises an assisting material, the assisting material may be 1% by mass or more and less than 50% by mass of the entire light-emitting layer, and is preferably 10% by mass or more and less than 50% by mass. The guest may be 0.01% by mass or more and 20% by mass or less, and is preferably 0.01% by mass or more and 5% by mass or less.

[0114] The inventors have conducted various studies and found that when the organic compound according to the present invention is used as a host material or guest material for the light-emitting layer, particularly as a guest material for the light-emitting layer, a device can be obtained that exhibits high efficiency, high brightness, and extremely high durability. This light-emitting layer may be a single layer or a multi-layer, and it is also possible to mix the light emission with the blue light emission of this embodiment by including a light-emitting material having another light emission color. A multi-layer means a state in which one light-emitting layer and another light-emitting layer are stacked. In this case, the light emission color of the organic light-emitting element is not limited to blue. More specifically, it may be white or an intermediate color. In the case of white, the other light-emitting layer emits a color other than blue, i.e., red or green. Furthermore, the film is formed by vapor deposition or coating. Details of this will be explained in detail in the examples described later.

[0115] The organic compound according to the present invention can be used as a constituent material for organic compound layers other than the light-emitting layer constituting the organic light-emitting device according to this embodiment. Specifically, it may be used as a constituent material for electron transport layers, electron injection layers, hole transport layers, hole injection layers, hole blocking layers, etc. In this case, the light-emitting color of the organic light-emitting device is not limited to blue. More specifically, it may be white light or an intermediate color.

[0116] (3) Other Compounds In addition to the organic compounds according to the present invention, conventionally known low-molecular-weight and high-molecular-weight hole-injection compounds or hole-transport compounds, host materials, luminescent compounds, electron-injection compounds or electron-transport compounds, etc., can be used together as needed. Examples of these compounds are listed below.

[0117] As hole-implantation transport materials, materials with high hole mobility are preferred to facilitate hole injection from the anode and to transport the injected holes to the light-emitting layer. Furthermore, materials with a high glass transition temperature are preferred to reduce film quality degradation such as crystallization in organic light-emitting devices. Examples of low-molecular-weight and high-molecular-weight materials with hole-implantation transport properties include triarylamine derivatives, arylcarbazole derivatives, phenylenediamine derivatives, stilbene derivatives, phthalocyanine derivatives, porphyrin derivatives, poly(vinylcarbazole), poly(thiophene), and other conductive polymers. Moreover, the above-mentioned hole-implantation transport materials are also suitably used in electron-blocking layers. Specific examples of compounds used as hole-implantation transport materials are shown below, but are not limited to these.

[0118]

[0119] Guest materials primarily involved in luminescence include organic compounds represented by general formula [1], as well as fused ring compounds (e.g., fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, organoaluminum complexes such as tris(8-quinolinolate)aluminum, iridium complexes, platinum complexes, rhenium complexes, copper complexes, europium complexes, ruthenium complexes, and polymer derivatives such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives. Specific examples of compounds used as luminescent materials are shown below, but are not limited to these.

[0120]

[0121]

[0122] Examples of host or assist materials included in the luminescent layer include aromatic hydrocarbon compounds or their derivatives, as well as carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organoaluminum complexes such as tris(8-quinolinolate)aluminum, and organoberylium complexes. Specific examples of compounds used as luminescent layer hosts or luminescence assist materials are shown below, but are not limited to these.

[0123]

[0124] Among EM1 to EM40, the host material may be a hydrocarbon compound having a condensed polycyclic hydrocarbon group. Specifically, these are EM1 to EM12 and EM16 to EM27.

[0125] As electron-transporting materials, any material capable of transporting electrons injected from the cathode to the light-emitting layer can be arbitrarily selected, taking into consideration the balance with the hole mobility of the hole-transporting material. Examples of materials with electron-transporting properties include oxadiazole 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 suitably used in the hole-blocking layer. Specific examples of compounds used as electron-transporting materials are shown below, but are of course not limited to these.

[0126]

[0127] Electron-injectable materials can be arbitrarily selected from those that allow for easy electron injection from the cathode, taking into consideration the balance with hole injection properties. Organic compounds include n-type dopants and reducing dopants. Examples include alkali metal compounds such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fluvalene derivatives, and acridine derivatives.

[0128] (4) Configuration of the Organic Light-Emitting Device The following describes the components that make up the organic light-emitting device of this embodiment.

[0129] An organic light-emitting element is provided on a substrate by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode. A protective layer, a color filter, a microlens, etc., may be provided on the second electrode. If a color filter is provided, a planarization layer may be provided between it and the protective layer. The planarization layer can be made of acrylic resin or the like. The same applies when a planarization layer is provided between the color filter and the microlens.

[0130] [Substrate] Examples of substrates include quartz, glass, silicon wafers, resins, and metals. Switching elements such as transistors and wiring may be provided on the substrate, and an insulating layer may be provided on top of them. The insulating layer can be made of any material that allows for the formation of contact holes so that wiring can be formed between it and the first electrode, and that ensures insulation from wiring that is not connected. For example, resins such as polyimide, silicon oxide, and silicon nitride can be used.

[0131] [Electrodes] A pair of electrodes can be used. The pair of electrodes consists of a first electrode and a second electrode. Specifically, 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 the higher potential is the anode, and the other is the cathode. Alternatively, the electrode that supplies holes to the light-emitting layer may be the anode, and the electrode that supplies electrons may be the cathode.

[0132] The anode material should ideally have a high work function. For example, elemental metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten, or mixtures containing these, or alloys combining them, as well as metal oxides such as tin oxide, zinc oxide, indium oxide, tin-indium oxide (ITO), and zinc-indium oxide can be used. Conductive polymers such as polyaniline, polypyrrole, and polythiophene can also be used.

[0133] These electrode materials may be used individually or in combination of two or more types. Furthermore, the anode may consist of a single layer or multiple layers.

[0134] When used as a reflective electrode, materials such as chromium, aluminum, silver, titanium, tungsten, molybdenum, or alloys or laminates thereof can be used. These materials can also function as reflective films without serving as electrodes. Furthermore, when used as a transparent electrode, oxide transparent conductive layers such as indium tin oxide (ITO) or indium zinc oxide can be used, but are not limited to these. Photolithography techniques can be used to form the electrodes.

[0135] 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 elemental metals or mixtures containing aluminum, titanium, manganese, silver, lead, and chromium. Alternatively, alloys combining these elemental metals can also 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 may be used individually or in combination of two or more. The cathode may also be 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 important as long as silver aggregation is reduced. For example, the ratio of silver to other metals may be 1:1, 3:1, etc.

[0136] 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 using DC and AC sputtering methods is more preferable because it provides good film coverage and makes it easier to reduce resistance.

[0137] [Organic Compound Layer] The organic compound layer may be formed as a single layer or as multiple layers. If there are multiple layers, they may be called a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport layer, or an electron injection layer, depending on their function. The organic compound layer is mainly composed of organic compounds, but may also contain inorganic atoms and inorganic compounds. For example, it may contain copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, etc. The organic compound layer may be placed between the first electrode and the second electrode, or it may be placed in contact with the first electrode and the second electrode.

[0138] The organic compound layers constituting the organic light-emitting element according to this embodiment (hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, etc.) are formed by the method shown below.

[0139] The organic compound layer constituting the organic light-emitting element according to this embodiment can be formed using a dry process such as vacuum deposition, ionization deposition, sputtering, or plasma deposition. Alternatively, instead of a dry process, a wet process can be used in which the layer is formed by dissolving the compound in a suitable solvent and applying a known coating method (e.g., spin coating, dipping, casting, LB method, inkjet method, etc.).

[0140] By forming layers using methods such as vacuum deposition or solution coating, crystallization is less likely to occur, resulting in excellent stability over time. Furthermore, when forming films using coating methods, it is possible to combine the film with an appropriate binder resin.

[0141] Examples of the binder resins mentioned above include, but are not limited to, polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, and urea resin.

[0142] Furthermore, these binder resins may be used individually as homopolymers or copolymers, or as a mixture of two or more types. Additionally, known additives such as plasticizers, antioxidants, and UV absorbers may be used in combination as needed.

[0143] [Protective Layer] A protective layer may be provided on the cathode. For example, by bonding glass with a desiccant to the cathode, the intrusion of water and other substances into the organic compound layer can be reduced, thereby reducing the occurrence of display defects. In another embodiment, a passivation film such as silicon nitride may be provided on the cathode to reduce the intrusion of water and other substances into the organic compound layer. For example, after forming the cathode, the material may be transported to another chamber without breaking the vacuum, and a silicon nitride film with a thickness of 2 μm may be formed by CVD to serve as a protective layer. A protective layer may also be provided using atomic deposition (ALD) after the film formation by CVD. The material of the film formed by ALD is not limited, but may be silicon nitride, silicon oxide, aluminum oxide, etc. Silicon nitride may be further formed by CVD on the film formed by ALD. The film formed by ALD may have a thinner film thickness than the film formed by CVD. Specifically, the film thickness of the film formed by the ALD method may be 50% or less, and even 10% or less, of the film thickness of the film formed by the CVD method.

[0144] [Color Filter] A color filter may be provided on top of the protective layer. For example, a color filter that takes into account the size of the organic light-emitting element may be provided on a separate substrate and bonded to the substrate on which the organic light-emitting element is provided, or a color filter may be patterned on the protective layer as described above using photolithography technology. The color filter may be made of polymer.

[0145] [Planarizing Layer] A planarizing layer may be provided between the color filter and the protective layer. The planarizing layer is provided for the purpose of reducing the unevenness of the layer below. It may also be called a material resin layer without limiting its purpose. The planarizing layer may be composed of an organic compound, and may be low molecular weight or high molecular weight, but high molecular weight is preferred.

[0146] The planarization layer may be provided above or below the color filter, and its constituent materials may be the same or different. Specifically, examples include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenolic resin, epoxy resin, silicone resin, urea resin, etc.

[0147] [Microlens] The organic light-emitting element according to this embodiment may have an optical element such as a microlens on the light-emitting side. The microlens may be made of acrylic resin, epoxy resin, etc. The microlens may be used to increase the amount of light extracted from the organic light-emitting element and to control the direction of the extracted light. The microlens may have a hemispherical shape. If it has a hemispherical shape, among the tangents that are tangent to the hemisphere, there is a tangent that is parallel to the insulating layer, and the point of contact between that tangent and the hemisphere is the vertex of the microlens. The vertex of the microlens can be similarly determined in any cross-sectional view. That is, among the tangents that are tangent to the semicircle of the microlens in the cross-sectional view, there is a tangent that is parallel to the insulating layer, and the point of contact between that tangent and the semicircle is the vertex of the microlens.

[0148] Furthermore, the midpoint of a microlens can also be defined. In the cross-section of a microlens, a line segment can be imagined from the point where one arc shape begins to the point where another arc shape begins, and the midpoint of this line segment can be called the midpoint of the microlens. The cross-section used to determine the vertices and midpoints may be a cross-section perpendicular to the insulating layer.

[0149] [Opposite Substrate] An opposite substrate may be provided on the planarization layer. The opposite substrate is called an opposite substrate because it is provided in a position corresponding to the aforementioned substrate. The constituent material of the opposite substrate may be the same as that of the aforementioned substrate. The opposite substrate may be the second substrate if the aforementioned substrate is the first substrate.

[0150] [Pixel Circuit] The light-emitting device may have a pixel circuit connected to a light-emitting element. The pixel circuit may be an active-matrix type that independently controls the emission of light from a first light-emitting element and a second light-emitting element. 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 include a light-emitting element, a transistor that controls the emission brightness of the light-emitting element, a transistor that controls the emission timing, a capacitor that holds the gate voltage of the transistor that controls the emission brightness, and a transistor for connecting to GND without going through the light-emitting element.

[0151] The light-emitting device has a display area and a peripheral area arranged around the display area. The display area has a pixel circuit, and the peripheral area has a display control circuit. The mobility of the transistors constituting the pixel circuit may be smaller than the mobility of the transistors constituting the display control circuit.

[0152] The slope of the current-voltage characteristics of the transistors constituting the pixel circuit may be smaller than the slope of the current-voltage characteristics of the transistors constituting the display control circuit. The slope of the current-voltage characteristics can be measured using the so-called Vg-Ig characteristic.

[0153] The transistors that make up the pixel circuit are transistors connected to light-emitting elements, such as the first light-emitting element.

[0154] [Pixels] The organic light-emitting device has a plurality of pixels. Each pixel has sub-pixels that emit different colors from the others. The sub-pixels may each have, for example, RGB emission colors.

[0155] A pixel emits light in a region also called the pixel aperture. This region is the same as the first region. 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.

[0156] The distance between subpixels may be 10 μm or less, specifically 8 μm, 7.4 μm, or 6.4 μm.

[0157] Pixels can take on known arrangements in a plan view. For example, they may be in a stripe arrangement, delta arrangement, pentile arrangement, or Bayer arrangement. The shape of subpixels in a plan view may be any known shape. For example, rectangles, rhombuses, hexagons, etc. Of course, even if it is not a precise shape, if it is close to a rectangle, it is included in the category of rectangles. The shape of subpixels and the pixel arrangement can be used in combination.

[0158] (5) Applications of the Organic Light-Emitting Device According to This Embodiment The organic light-emitting device according to this embodiment can be used as a component of an image display device, a display device, a lighting device, etc. Other applications include a display unit for an image display device having a display unit and a housing on which the display unit is provided, an exposure light source for an electrophotographic image forming apparatus, a backlight for a liquid crystal display device, and a light-emitting device having a color filter in a white light source.

[0159] The display device may also be an image information processing device that has an image input unit for receiving image information from an area CCD, linear CCD, memory card, etc., an information processing unit for processing the input information, and displays the input image on the display unit.

[0160] Furthermore, the display unit of the imaging device or inkjet printer may have a touch panel function. The driving method for this touch panel function may be infrared, capacitive, resistive, or electromagnetic induction, and is not particularly limited. The display device may also be used as the display unit of a multifunction printer.

[0161] Next, the display device according to this embodiment will be described with reference to the drawings.

[0162] Figures 1A and 1B are schematic cross-sectional diagrams showing an example of a display device having an organic light-emitting element and a transistor connected to this organic light-emitting element. The transistor is an example of an active element. The transistor may also be a thin-film transistor (TFT).

[0163] Figure 1A shows an example of a pixel, which is a component of the display device according to this embodiment. The pixel has sub-pixels 10. The sub-pixels are divided into 10R, 10G, and 10B based on their light emission. The light emission color may be distinguished by the wavelength emitted from the light-emitting layer, or the light emitted from the sub-pixel may be selectively transmitted or color-converted by a color filter or the like. Each sub-pixel has a reflective electrode 2 which is a first electrode, an insulating layer 3 covering the end of the reflective electrode 2, an organic compound layer 4 covering the first electrode and the insulating layer, a transparent electrode 5, a protective layer 6, and a color filter 7 on an interlayer insulating layer 1.

[0164] The interlayer insulating layer 1 may have transistors and capacitive elements arranged in the layer below or inside it. The transistor and the first electrode may be electrically connected via a contact hole or the like (not shown).

[0165] The insulating layer 3 is also called a bank or pixel separation layer. It covers the edge of the first electrode and is arranged to surround the first electrode. The portion without the insulating layer is in contact with the organic compound layer 4 and becomes the light-emitting region.

[0166] The organic compound layer 4 includes a hole injection layer 41, a hole transport layer 42, a first light-emitting layer 43, a second light-emitting layer 44, and an electron transport layer 45.

[0167] The second electrode 5 may be a transparent electrode, a reflective electrode, or a semi-transparent electrode.

[0168] The protective layer 6 reduces the penetration of moisture into the organic compound layer. Although the protective layer is shown as a single layer, it may consist of multiple layers. Each layer may contain an inorganic compound layer and an organic compound layer.

[0169] The color filters 7 are classified into 7R, 7G, and 7B according to their color. The color filters may be formed on a planarization film (not shown). The color filters may also have a resin protective layer (not shown). Alternatively, the color filters may be formed on a protective layer 6, or they may be bonded together after being placed on an opposing substrate such as a glass substrate.

[0170] Figure 1B shows a display device 100 which includes an organic light-emitting element 26 and a TFT 18 as an example of a transistor. A substrate 11 made of glass, silicon, or the like is provided, with an insulating layer 12 on top of it. An active element 18 such as a TFT is placed on the insulating layer, and the gate electrode 13, gate insulating film 14, and semiconductor layer 15 of the active element are arranged therein. The active element 18 is also composed of a semiconductor layer 15, a drain electrode 16, and a source electrode 17. An insulating film 19 is provided on top of the active element 18. The anode 21 and the source electrode 17 that constitute the organic light-emitting element 26 are connected via a contact hole 20 provided in the insulating film.

[0171] Note that the method of 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 configuration shown in Figure 1B. In other words, it is sufficient for either the anode or cathode to be electrically connected to either the TFT source electrode or the drain electrode. TFT refers to a thin-film transistor.

[0172] In the display device 100 shown in Figure 1B, the organic compound layer is depicted as a single layer, but the organic compound layer 22 may consist of multiple layers. A first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce the degradation of the organic light-emitting element.

[0173] In the display device 100 shown in Figure 1B, a transistor is used as the switching element, but other switching elements may be used instead.

[0174] Furthermore, the transistor used in the display device 100 in Figure 1B is not limited to a transistor using a single-crystal silicon wafer, but may also be a thin-film transistor having an active layer on an insulating surface of the substrate. Examples of active layers include non-single-crystal silicon such as single-crystal silicon, amorphous silicon, and microcrystalline silicon, and non-single-crystal oxide semiconductors such as indium zinc oxide and indium gallium zinc oxide. Thin-film transistors are also called TFT elements.

[0175] The transistors included in the display device 100 in Figure 1B may be formed within a substrate such as a Si substrate. Here, "formed within a substrate" means that the transistors are manufactured by processing the substrate itself, such as a Si substrate. In other words, having transistors within a substrate can be seen as the substrate and transistors being formed as a single unit.

[0176] The organic light-emitting element according to this embodiment has its luminescence controlled by a TFT, which is an example of a switching element, and by providing multiple organic light-emitting elements on the surface, an image can be displayed according to the luminescence of each element. The switching element according to this embodiment is not limited to a TFT, but may also be a transistor made of low-temperature polysilicon, or an active matrix driver formed on a substrate such as a Si substrate. "On the substrate" can also mean "within the substrate." Whether to provide a transistor within the substrate or to use a TFT is selected depending on the size of the display area; for example, if the size is about 0.5 inches, it is preferable to provide the organic light-emitting element on a Si substrate.

[0177] Figure 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. The display panel 1005 may have an organic light-emitting element according to this embodiment. Flexible printed circuits FPCs 1002 and 1004 are connected to the touch panel 1003 and the display panel 1005, respectively. Transistors are printed on the circuit board 1007. The battery 1008 does not need to be provided if the display device is not a portable device, or it may be provided in a different location even if it is a portable device.

[0178] The display device according to this embodiment may have a color filter having red, green, and blue colors. The color filter may have the red, green, and blue colors arranged in a delta array.

[0179] The display device according to this embodiment may be used in the display unit of a mobile terminal. In that case, it may have both display and operation functions. Examples of mobile terminals include smartphones and other mobile phones, tablets, and head-mounted displays.

[0180] The display device according to this embodiment may be used in the display unit of an imaging device having an image sensor that receives light. The imaging device may have a display unit that displays information acquired by the image sensor. The display unit may be an external display unit or a display unit located inside the viewfinder. The imaging device may be a digital camera or a digital video camera.

[0181] Figure 3A is a schematic diagram showing 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 and the rear display 1102 may have organic light-emitting elements according to this embodiment. In that case, the viewfinder 1101 and the rear display 1102 may display not only the image to be captured, but also environmental information, imaging instructions, etc. Environmental information may include the intensity of ambient light, the direction of ambient light, the speed at which the subject is moving, the possibility of the subject being obscured by an obstacle, etc.

[0182] Since the optimal timing for imaging is very short, it is best to display the information as quickly as possible. Therefore, it is preferable to use a display device using the organic light-emitting element according to this embodiment, because organic light-emitting elements have a fast response speed.

[0183] The imaging device 1100 may further include an optical section (not shown). The lenses in the optical section may be one or more, and they form an image on the image sensor housed in the housing 1104. The focus can be adjusted by adjusting the relative positions of the multiple lenses. This operation can also be performed automatically. The imaging device may also be called a photoelectric converter. The photoelectric converter may not capture images sequentially, but may include methods of capturing images such as detecting the difference from the previous image or extracting from an image that is always being recorded.

[0184] Figure 3B is a schematic diagram showing an example of an electronic device according to this embodiment. The electronic device 1200 has a display unit 1201, an operation unit 1202, and a housing 1203. The housing 1203 may have a circuit, a printed circuit board having the circuit, a battery, and a communication unit. The operation unit 1202 may be a button or a touch panel type response unit. The operation unit may also be a biometric recognition unit that recognizes fingerprints to unlock or otherwise perform actions. 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. Images captured by the camera function are displayed on the display unit. Examples of electronic devices include smartphones and laptop computers.

[0185] Figures 4A and 4B are schematic diagrams showing an example of a display device according to this embodiment. Figure 4A is a display device such as a television monitor or a PC monitor. The display device 1300 has a housing 1301 and a display unit 1302. An organic light-emitting element according to this embodiment may be used in the display unit 1302.

[0186] The display device 1300 may have a housing 1301 and a base 1303 that supports the display unit 1302. The base 1303 is not limited to the form shown in Figure 4A. The lower edge of the housing 1301 may also serve as the base.

[0187] Furthermore, the housing 1301 and the display unit 1302 may be curved. Their radius of curvature may be between 5000 mm and 6000 mm.

[0188] Figure 4B is a schematic diagram showing another example of a display device according to this embodiment. The display device 1310 in Figure 4B is configured to be foldable and is a so-called foldable display device. The display device 1310 has a first display unit 1311, a second display unit 1312, a housing 1313, and a bending point 1314. The first display unit 1311 and the second display unit 1312 may have organic light-emitting elements according to this embodiment. The first display unit 1311 and the second display unit 1312 may be a single display device without seams. The first display unit 1311 and the second display unit 1312 can be separated by a bending point. The first display unit 1311 and the second display unit 1312 may each display different images, or the first and second display units may together display a single image.

[0189] Figure 5A is a schematic diagram showing an example of a lighting device according to this embodiment. The lighting device 1400 may have a housing 1401, a light source 1402, and a circuit board 1403. The light source 1402 may have an organic light-emitting element according to this embodiment. The lighting device 1400 may have an optical film 1404 to improve the color rendering of the light source. The lighting device 1400 may also have a light diffusion section 1405 to effectively diffuse the light from the light source. The lighting device 1400 having a light diffusion section 1405 allows light to be delivered over a wide area. The optical film 1404 and the light diffusion section 1405 may be provided on the light-emitting side of the lighting. A cover may be provided on the outermost part as needed.

[0190] The lighting device is, for example, a device for illuminating a room. The lighting device may emit white light, daylight white light, or any other color from blue to red. The lighting device according to this embodiment may have a dimming circuit for adjusting the brightness of these colors. The lighting device according to this embodiment may also have a power supply circuit connected to the organic light-emitting element according to this embodiment. The power supply circuit may be a circuit that converts AC voltage to DC voltage. White is defined as a color temperature of 4200K, and daylight white is defined as a color temperature of 5000K. The lighting device according to this embodiment may further have a color filter.

[0191] Furthermore, the lighting device according to this embodiment may have a heat dissipation section. The heat dissipation section releases heat from inside the device to the outside, and examples include metals, ceramics, and the like with high thermal conductivity.

[0192] Figure 5B is a schematic diagram of an automobile, which is an example of a mobile body according to this embodiment. The automobile has a taillight, which is an example of a lighting device. The automobile 1500 has a taillight 1501 and a body 1503, and the taillight may illuminate when the brakes are applied or the like. The body 1503 may also be called the machine body. The automobile 1500 may have a window 1502 attached to the body 1503.

[0193] The tail lamp 1501 may have an organic light-emitting element according to this embodiment. The tail lamp may have a protective member to protect the light source. The protective member has a reasonably high strength and can be made of any transparent material, but it is preferably made of polycarbonate or the like. A frangic acid derivative, an acrylonitrile derivative, or the like may be mixed with the polycarbonate.

[0194] The window 1502 may be a transparent display if it is not a window for checking the front and rear of the automobile. The transparent display may have an organic light-emitting element according to this embodiment. In this case, the constituent materials such as electrodes of the organic light-emitting element according to the present invention are made of transparent material.

[0195] Furthermore, as shown in Figure 5C, the automobile 1500 includes a steering wheel 1504 for controlling the direction of movement of the moving body, a display unit 1505 mounted on the vehicle body 1503 for displaying a map, the position of the moving body, the direction of turns, etc. The display unit 1505 may also have an organic light-emitting element according to this embodiment.

[0196] The mobile body according to this embodiment includes a drive force generating unit that generates a driving force mainly used for the movement of the mobile body, and one or both of a rotating body mainly used for the movement of the mobile body. The drive force generating unit may be an engine, a motor, etc. The rotating body may be a tire, a wheel, a ship's propeller, etc. Specifically, it may be a bicycle, an automobile, a train, a ship, an aircraft, a drone, etc. The mobile body may have a body and a light fixture or display unit provided on the body. The light fixture may emit light to indicate the position of the body.

[0197] Referencing Figures 6A and 6B, examples of applications of the display devices of each embodiment described above will be explained. The display device can be applied to systems that can be worn as wearable devices, such as smart glasses, head-mounted displays, and smart contact lenses. A display device that can be used in a wearable device may have an imaging device capable of photoelectric conversion of visible light and a display device capable of emitting visible light.

[0198] Figures 6A and 6B are schematic diagrams showing an example of eyeglasses (smart glasses) according to this embodiment. The eyeglasses 1600 (smart glasses) will be described using Figure 6A. The eyeglasses 1600 has a display unit on the back side of the lens 1601. The display unit may have an organic light-emitting element according to the present invention. Furthermore, an imaging device 1602 such as a CMOS sensor or SPAD may be provided on the front side of the lens 1601.

[0199] The eyeglasses 1600 further include a control device 1603. The control device 1603 functions as a power supply that provides power to the imaging device 1602 and the display unit. The control device 1603 also controls the operation of the imaging device 1602 and the display unit. The lens 1601 has an optical system formed therein for focusing light from the imaging device 1602 and the display unit.

[0200] Figure 6B will be used to describe the eyeglasses 1610 (smart glasses). The eyeglasses 1610 have a control device 1612, and the control device 1612 is equipped with a display device having an organic light-emitting element according to the present invention. The control device 1612 may further have an imaging device corresponding to an imaging device 1602. An optical system for projecting light emitted from the control device 1612 is formed in the lens 1611, and an image is projected onto the lens 1611. The control device 1612 functions as a power supply that supplies power to the imaging device and the display device, and also controls the operation of the imaging device and the display device. The control device may have a gaze detection unit that detects the wearer's gaze. Gaze detection may use infrared light. The infrared light-emitting unit emits infrared light towards the eyeball of the user who is gazing at the displayed image. An image of the eyeball is obtained by detecting the reflected light from the eyeball of the emitted infrared light with an imaging unit having a light-receiving element. By having a reduction means that reduces the light from the infrared light-emitting unit to the display unit in planar view, the deterioration of image quality is reduced.

[0201] The control device 1612 detects the user's gaze toward the displayed image from the image of the eyeball obtained by imaging with infrared light. Any known method can be applied to gaze detection using the image of the eyeball. For example, a gaze detection method based on the Purkinje image obtained by the reflection of the irradiated light from the cornea can be used.

[0202] More specifically, gaze detection processing is performed based on the pupil-corneal reflection method. Using the pupil-corneal reflection method, a gaze vector representing the orientation (rotation angle) of the eyeball is produced based on the pupil image and Purkinje image contained in the captured image of the eyeball, thereby detecting the user's gaze.

[0203] The display device according to this embodiment includes an imaging device having a light-receiving element, and may control the display image of the display device based on the user's gaze information from the imaging device.

[0204] Specifically, the display device determines a first field of view that the user is fixated on, and a second field of view other than the first field of view, based on gaze information. The first and second field of view may be determined by the display device's control unit, or they may be determined by an external control unit and received by the display device. Within the display area of ​​the display device, the display resolution of the first field of view may be controlled to be higher than that of the second field of view. In other words, the resolution of the second field of view may be lower than that of the first field of view.

[0205] Furthermore, the display area has a first field of view and a second field of view different from the first field of view, and based on gaze information, a higher priority area is determined from the first and second field of view. The first and second field of view areas may be determined by the control device of the display device, or they may be determined by an external control device and received. The resolution of the higher priority area may be controlled to be higher than the resolution of the areas other than the higher priority area. In other words, the resolution of areas with relatively lower priority may be set lower.

[0206] AI may be used to determine the first field of view and the field of view with higher priority. The AI ​​may be a model configured to estimate the angle of line of sight and the distance to the target object at the end of the line of sight from the image of the eye, using the image of the eye and the direction the eye was actually looking in the image as training data. The AI ​​may be provided by the display device, the imaging device, or an external device. If the external device has the AI, it can preferably be applied to smart glasses that further have an imaging device for capturing images of the outside. The smart glasses can display the captured external information in real time.

[0207] Figure 7A is a schematic diagram showing an example of an image forming apparatus according to this embodiment. The image forming apparatus 40 is an electrophotographic image forming apparatus and includes a photoreceptor 27, an exposure light source 28, a charging unit 30, a developing unit 31, a transfer unit 32, a transport roller 33, and a fuser 35. Light 29 is irradiated from the exposure light source 28, and an electrostatic latent image is formed on the surface of the photoreceptor 27. This exposure light source 28 may have an organic light-emitting element according to this embodiment. The developing unit 31 has toner or the like. The charging unit 30 charges the photoreceptor 27. The transfer unit 32 transfers the developed image to a storage medium 34. The transport roller 33 transports the recording medium 34. The recording medium 34 is, for example, paper. The fuser 35 fixes the image formed on the recording medium 34.

[0208] Figures 7B and 7C are diagrams showing the exposure light source 28, schematic diagrams showing how multiple light-emitting units 36 are arranged on a long substrate. Arrows 37 indicate the direction of the column in which the organic light-emitting elements are arranged. This column direction is the same as the direction of the axis in which the photoreceptor 27 rotates. This direction can also be called the long axis direction of the photoreceptor 27. Figure 7B shows a configuration in which the light-emitting units 36 are arranged along the long axis direction of the photoreceptor 27. Figure 7C shows a different configuration from Figure 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 with intervals between them. In the second column, light-emitting units 36 are located at positions corresponding to the intervals between the light-emitting units 36 in the first column. That is, multiple light-emitting units 36 are also arranged with intervals between them in the row direction. The arrangement in Figure 7C can also be described as a grid pattern, a houndstooth pattern, or a checkerboard pattern.

[0209] As described above, by using the device employing the organic light-emitting element according to this embodiment, it becomes possible to display images with good quality and stable display even for extended periods.

[0210] The present invention will be described below with reference to examples. However, the present invention is not limited to these examples.

[0211] [Example 1 (Synthesis of Exemplary Compound A1)]

[0212]

[0213] (1-1) Synthesis of Intermediate G3100 mL eggplant flask was charged with the following reagents and solvents.Compound G1: 1.00 g (2.72 mmol)Compound G2: 979 mg (2.72 mmol)PdCl ２ (PPh ３ ) ２ : 57 mg (0.08 mmol)K ２ CO ３ : 1.88 g (13.6 mmol)Toluene: 30 mLEthanol: 10 mLWater: 10 mL

[0214] Next, the reaction solution was heated to 90 °C under a nitrogen stream and stirred at this temperature (90 °C) for 5 hours. After completion of the reaction, methanol was added and filtration was performed to obtain a crude product as the filtrate. This was purified by silica gel column chromatography (heptane: toluene) to obtain 439 mg (yield: 31%) of Intermediate G3.

[0215] (1-2) Synthesis of Exemplary Compound A1100 mL eggplant flask was charged with the following reagents and solvents.Compound G3: 400 mg (0.7​​​​​​​​[MALDI-TOF-MS] Measured value: m / z = 517 Calculated value: C ４０ H ２３ N = 517

[0219] [Examples 2 to 17 (Synthesis of Exemplary Compounds)] Exemplary compounds were synthesized in the same manner as in Example 1, except that raw material G1 was replaced with raw material 1, raw material G2 with raw material 2, and raw material G4 with raw material 3. Raw materials 1 to 3 for each example are shown in Table 4. Also, the measured values ​​(m / z) of the mass spectrometry results, measured in the same manner as in Example 1, are shown in Table 4.

[0220]

[0221]

[0222] [Example 18 (Fabrication of Organic Light-Emitting Device)] In this example, a blue organic light-emitting device with a bottom emission structure was fabricated, in which an anode, hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, and cathode were sequentially formed on a substrate. Table 5 shows the device configuration.

[0223] A 40 nm thick Ti film was deposited on a glass substrate using sputtering, and the pattern was created using photolithography to form the anode. The electrode area of ​​the anode was 3 mm². ２ I made it so that it would look like that. Then I washed it.

[0224] Next, the electrode-equipped substrate prepared above is attached to the vacuum deposition apparatus (manufactured by ULVAC), and after preparing for the deposition of the deposition material, 1.33 × 10 －４ Pa(1 × 10) －６ The chamber was evacuated to Torr. Afterward, the chamber was UV / ozone cleaned. Then, each layer was fabricated according to the layer configuration shown in Table 5 below. The substrate was then transferred to a glove box and sealed with a glass cap containing a desiccant in a nitrogen atmosphere to obtain an organic light-emitting element. In Table 5, "%" represents "mass%".

[0225]

[0226] The characteristics of the obtained elements were measured and evaluated. The current density of the light-emitting element was 100 mA / cm². ２The external quantum efficiency (EQE) was 5%. Furthermore, the current density was 100 mA / cm². ２ A continuous operation test was conducted, and the time at which the brightness degradation rate reached 5% was measured. When the time at which the brightness degradation rate reached 5% in Comparative Example 1 was set to 1.0, the brightness degradation rate ratio in this embodiment was 1.4.

[0227] In this embodiment, the measuring device specifically measured the current-voltage characteristics with a Hewlett-Packard 4140B micro-ammeter, and the luminous intensity with a Topcon BM7.

[0228] (Examples 19 to 37, Comparative Examples 1 to 3) Organic light-emitting devices were fabricated in the same manner as in Example 18, except that the composition of the organic compound layer was changed as shown in Table 6, and their characteristics were evaluated. In the table, "%" represents "mass%".

[0229] The luminous efficiency ratio is calculated based on a current density of 100 mA / cm². ２ The external quantum efficiency (EQE) was measured and is shown as a ratio when the efficiency of the device in Comparative Example 1 is set to 1.0. The device durability ratio is given by a current density of 100 mA / cm². ２ A continuous operation test was conducted, and the brightness was measured after 100 hours. The results are shown as a ratio with the brightness of the element in Comparative Example 1 set to 1.0. The results are shown in Table 6.

[0230]

[0231]

[0232] Table 6 shows that the organic light-emitting device using the organic compound according to the present invention exhibited superior luminous efficiency and durability compared to the organic light-emitting device of the comparative example. This is thought to be because the organic compound according to the present invention has the configurations described in (1-1) and (1-2) above.

[0233] Furthermore, Example 23 is an organic light-emitting element with particularly excellent durability, and Examples 26, 27, 36, and 37 are organic light-emitting elements with particularly excellent luminous efficiency. Since all of these organic light-emitting elements have the configurations of (1-4), (1-5), and (1-6), they are considered to have particularly excellent durability or luminous efficiency.

[0234] Based on the above, the organic compound according to the present invention is an organic compound with excellent luminescence efficiency and durability.

[0235] Furthermore, the present invention can also take the following configuration.

[0236] (Composition 1) An organic compound characterized by being represented by general formula (1).

[0237]

[0238] In general formula (1), R １ ~R １９ Each of these is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, and a cyano group.

[0239] Ar １ This is an aromatic hydrocarbon ring, a heteroaromatic ring, or a combination thereof. The aromatic hydrocarbon ring and the heteroaromatic ring may have substituents.

[0240] Ar ２ This is a hydrogen atom, a deuterium atom, an aromatic hydrocarbon ring, or a combination of aromatic hydrocarbon rings. The aromatic hydrocarbon ring and the heteroaromatic ring may have substituents.

[0241] n is either 0 or 1.

[0242] (Configuration 2) The organic compound according to Configuration 1, characterized in that the permanent dipole moment of the organic compound is 0.4 or more.

[0243] (Construction 3) In general formula (1), Ar １ R １９ An organic compound according to configuration 1 or 2, characterized by being bonded by [a specific mechanism].

[0244] (Configuration 4) An organic compound according to any one of Configurations 1 to 3, characterized in that n is 0 in general formula (1).

[0245] (Construction 5) In general formula (1), Ar １An organic compound according to any one of configurations 1 to 4, characterized in that is an aromatic hydrocarbon ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 15 carbon atoms, or a combination thereof.

[0246] (Composition 6) In general formula (1), Ar １ An organic compound according to any one of configurations 1 to 5, characterized in that one of the members is an aromatic hydrocarbon ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 15 carbon atoms, a combination of an aromatic hydrocarbon ring having 6 to 10 carbon atoms and a heteroaromatic ring having 3 to 9 carbon atoms, a combination of an aromatic hydrocarbon ring having 6 to 10 carbon atoms and an aromatic hydrocarbon ring having 6 to 10 carbon atoms, or a combination of a heteroaromatic ring having 3 to 9 carbon atoms and a heteroaromatic ring having 3 to 9 carbon atoms.

[0247] (Composition 7) In general formula (1), Ar １ The organic compound according to any one of configurations 1 to 6, characterized in that is an aromatic hydrocarbon ring having 6 to 15 carbon atoms, or a heteroaromatic ring having 3 to 12 carbon atoms.

[0248] (Construction 8) In general formula (1), Ar １ An organic compound according to any one of configurations 1 to 7, characterized in that the ring is a benzene ring, a fluorene ring, a pyridine ring, a dibenzofuran ring, or a dibenzothiophene ring.

[0249] (Configuration 9) Ar １ An organic compound according to any one of the configurations 1 to 8, characterized in that it consists only of sp2 carbon atoms.

[0250] (Configuration 10) In general formula (1), Ar ２ An organic compound according to any one of the configurations 1 to 9, characterized in that the ring has 6 or more carbon atoms and 30 or fewer carbon atoms.

[0251] (Configuration 11) In general formula (1), Ar ２The organic compound according to any one of configurations 1 to 10, characterized in that is a benzene ring, a naphthalene ring, a fluorene ring, a triphenylene ring, a chrysene ring, a spirofluorene ring, or a combination thereof.

[0252] (Configuration 12) In general formula (1), Ar ２ An organic compound according to any one of configurations 1 to 11, characterized in that the ring is a benzene ring, a triphenylene ring, or a fluorene ring.

[0253] (Configuration 13) In general formula (1), Ar ２ The organic compound according to any one of configurations 1 to 12, characterized in that the substituent having is a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

[0254] (Configuration 14) In general formula (1), Ar ２ The organic compound according to any one of configurations 1 to 13, characterized in that the substituent having is a methyl group, a tert-butyl group, a tert-butyl group having deuterium, a phenyl group, a phenyl group having an alkyl group having 1 to 4 carbon atoms, a naphthyl group, or a triphenylene group.

[0255] (Configuration 15) In general formula (1), Ar ２ The organic compound according to any one of configurations 1 to 14, characterized in that the substituent possessed is a methyl group or a phenyl group having a tert-butyl group.

[0256] (Configuration 16) In general formula (1), R ３ and R ６ An organic compound according to any one of configurations 1 to 15, characterized in that the atom is a hydrogen atom.

[0257] (Configuration 17) An organic light-emitting element having a first electrode and a second electrode, and an organic compound layer disposed between the first electrode and the second electrode, wherein the organic compound layer has an organic compound as described in any of Configurations 1 to 16.

[0258] (Configuration 18) The organic light-emitting element according to Configuration 17, wherein the organic compound layer has a light-emitting layer, and the light-emitting layer has the organic compound.

[0259] (Configuration 19) The organic light-emitting element according to Configuration 18, wherein the light-emitting layer further comprises a first compound, and the lowest singlet excitation energy of the first compound is higher than the lowest singlet excitation energy of the organic compound.

[0260] (Configuration 20) The organic light-emitting element according to Configuration 19, wherein the light-emitting layer further comprises a second compound, and the lowest singlet excitation energy of the second compound is higher than the lowest singlet excitation energy of the organic compound and lower than the lowest singlet excitation energy of the second compound.

[0261] (Configuration 21) A display device having a plurality of pixels, wherein at least one of the plurality of pixels has an organic light-emitting element as described in any of Configurations 17 to 20 and a transistor connected to the organic light-emitting element.

[0262] (Configuration 22) A photoelectric conversion device comprising an image sensor that receives light and a display unit that displays an image captured by the image sensor, wherein the display unit has an organic light-emitting element as described in any of Configurations 17 to 20.

[0263] (Configuration 23) An image display device characterized by comprising a display unit having an organic light-emitting element as described in any of Configurations 17 to 20, and a housing on which the display unit is provided.

[0264] (Configuration 24) An electronic device comprising: a display unit having an organic light-emitting element as described in any of Configurations 17 to 20; a housing on which the display unit is provided; and a communication unit provided in the housing for communicating with the outside.

[0265] (Configuration 25) A wearable device comprising: a display unit having an organic light-emitting element as described in any of Configurations 17 to 20; an optical system for focusing light from the display unit; and a control device for controlling the display of the display unit.

[0266] (Configuration 26) A lighting device characterized by comprising a light source having an organic light-emitting element as described in any of Configurations 17 to 20, and a housing on which the light source is provided.

[0267] (Configuration 27) A mobile body characterized by having a light fixture having an organic light-emitting element as described in any of Configurations 17 to 20, and a body on which the light fixture is provided.

[0268] The present invention is not limited to the embodiments described above, and various modifications and variations are possible without departing from the spirit and scope of the invention. Accordingly, the following claims are attached to make the scope of the invention public.

[0269] This application claims priority based on Japanese Patent Application No. 2025-023999, filed on 18 February 2025, and all of its contents are incorporated herein by reference.

[0270] 1 Interlayer insulating layer 2 Reflective electrode 3 Insulating layer 4 Organic compound layer 5 Transparent electrode 6 Protective layer 7 Color filter 10 Sub-pixel 11 Substrate 12 Insulating layer 13 Gate electrode 14 Gate insulating film 15 Semiconductor layer 16 Drain electrode 17 Source electrode 18 Thin film transistor 19 Insulating film 20 Contact hole 21 Lower electrode 22 Organic compound layer 23 Upper electrode 24 First protective layer 25 Second protective layer 26 Organic light-emitting element 27 Photoreceptor 28 Exposure light source 29 Light 30 Charging unit 31 Developing unit 32 Transfer unit 33 Transport unit 34 Recording medium 35 Fixing unit 36 ​​Light-emitting unit 37 First direction parallel to the long axis of the photoreceptor 40 Image forming apparatus 100 Display device 1000 Display device 1001 Upper cover 1002 Flexible printed circuit board 1003 Touch panel 1004 Flexible printed circuit board 1005 Display panel 1006 Frame 1007 Circuit board 1008 Battery 1009 Lower cover 1100 Imaging device 1101 Viewfinder 1102 Rear display 1103 Operation unit 1104 Housing 1200 Electronic equipment 1201 Display unit 1202 Operation unit 1203 Housing 1300 Display device 1301 Frame 1302 Display unit 1303 Base 1310 Display device 1311 First display unit 1312 Second display unit 1313 Housing 1314 Bending point 1400 Lighting device 1401 Housing 1402 Light source 1403 Circuit board 1404 Optical film 1405 Light diffusion unit 1500 Automobile 1501 Taillight 1502 Window 1503 Body 1600 Smart Glasses 1601 Lens 1602 Imaging Device 1603 Control Device 1610 Smart Glasses 1611 Lens 1612 Control Device

Claims

1. An organic compound represented by general formula (1). In general formula (1), R １ ~R １９ Each is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, and a cyano group. １ is an aromatic hydrocarbon ring, a heteroaromatic ring, or a combination thereof. The aromatic hydrocarbon ring and the heteroaromatic ring may have substituents. Ar ２ n is a hydrogen atom, a deuterium atom, an aromatic hydrocarbon ring, or a combination of aromatic hydrocarbon rings. The aromatic hydrocarbon ring and the heteroaromatic ring may have substituents. n is 0 or 1.

2. The organic compound according to claim 1, wherein the permanent dipole moment of the organic compound is 0.4 or more.

3. In general formula (1), Ar １ R １９ The organic compound according to claim 1, which is bonded by [a certain mechanism].

4. The organic compound according to claim 1, wherein n is 0 in general formula (1).

5. In general formula (1), Ar １ The organic compound according to claim 1, wherein is an aromatic hydrocarbon ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 15 carbon atoms, or a combination thereof.

6. In general formula (1), Ar １ The organic compound according to claim 1, wherein is an aromatic hydrocarbon ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 15 carbon atoms, a combination of an aromatic hydrocarbon ring having 6 to 10 carbon atoms and a heteroaromatic ring having 3 to 9 carbon atoms, a combination of an aromatic hydrocarbon ring having 6 to 10 carbon atoms and an aromatic hydrocarbon ring having 6 to 10 carbon atoms, or a combination of a heteroaromatic ring having 3 to 9 carbon atoms and a heteroaromatic ring having 3 to 9 carbon atoms.

7. In the general formula (1), Ar １ The organic compound according to claim 1, wherein is an aromatic hydrocarbon ring having 6 to 15 carbon atoms or a heteroaromatic ring having 3 to 12 carbon atoms.

8. In general formula (1), Ar １ The organic compound according to claim 1, wherein is a benzene ring, a fluorene ring, a pyridine ring, a dibenzofuran ring, or a dibenzothiophene ring.

9. Ar １ The organic compound according to claim 1, wherein the carbon atom consists only of sp2 carbon atoms.

10. In general formula (1), Ar ２ The organic compound according to claim 1, wherein the ring is an aromatic hydrocarbon ring having 6 or more carbon atoms and 30 or fewer carbon atoms.

11. In general formula (1), Ar ２ The organic compound according to claim 1, wherein is a benzene ring, a naphthalene ring, a fluorene ring, a triphenylene ring, a chrysene ring, a spirofluorene ring, or a combination thereof.

12. In general formula (1), Ar ２ The organic compound according to claim 1, wherein is a benzene ring, a triphenylene ring, or a fluorene ring.

13. In general formula (1), Ar ２ The organic compound according to claim 1, wherein the substituent having is a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

14. In general formula (1), Ar ２ The organic compound according to claim 1, wherein the substituent having is a methyl group, a tert-butyl group, a tert-butyl group having deuterium, a phenyl group, a phenyl group having an alkyl group having 1 to 4 carbon atoms, a naphthyl group, or a triphenylene group.

15. In general formula (1), Ar ２ The organic compound according to claim 1, wherein the substituent possessed is a methyl group or a phenyl group having a tert-butyl group.

16. In general formula (1), R ３ and R ６ The organic compound according to claim 1, wherein is a hydrogen atom.

17. An organic light-emitting element 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 organic compound described in claim 1.

18. The organic light-emitting element according to claim 17, wherein the organic compound layer has a light-emitting layer, and the light-emitting layer has the organic compound.

19. The organic light-emitting element according to claim 18, wherein the light-emitting layer further comprises a first compound, and the lowest singlet excitation energy of the first compound is higher than the lowest singlet excitation energy of the organic compound.

20. The organic light-emitting element according to claim 19, wherein the light-emitting layer further comprises a second compound, the lowest singlet excitation energy of the second compound being higher than the lowest singlet excitation energy of the organic compound and lower than the lowest singlet excitation energy of the second compound.

21. A display device having a plurality of pixels, wherein at least one of the plurality of pixels is an organic light-emitting element according to any one of claims 17 to 20, and a transistor connected to the organic light-emitting element.

22. A photoelectric conversion device comprising an image sensor that receives light and a display unit that displays an image captured by the image sensor, wherein the display unit has an organic light-emitting element as described in any one of claims 17 to 20.

23. An image display device comprising a display unit having an organic light-emitting element according to any one of claims 17 to 20, and a housing on which the display unit is provided.

24. An electronic device comprising: a display unit having an organic light-emitting element as described in any one of claims 17 to 20; a housing on which the display unit is provided; and a communication unit provided in the housing for communicating with the outside.

25. A wearable device comprising: a display unit having an organic light-emitting element as described in any one of claims 17 to 20; an optical system for focusing light from the display unit; and a control device for controlling the display of the display unit.

26. A lighting device comprising a light source having an organic light-emitting element according to any one of claims 17 to 20, and a housing on which the light source is provided.

27. A mobile body comprising a lamp having an organic light-emitting element according to any one of claims 17 to 20, and a body on which the lamp is provided.

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