WO2023063112A1 - 有機化合物及び有機発光素子 - Google Patents

有機化合物及び有機発光素子 Download PDF

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WO2023063112A1
WO2023063112A1 PCT/JP2022/036681 JP2022036681W WO2023063112A1 WO 2023063112 A1 WO2023063112 A1 WO 2023063112A1 JP 2022036681 W JP2022036681 W JP 2022036681W WO 2023063112 A1 WO2023063112 A1 WO 2023063112A1
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light
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compound
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French (fr)
Japanese (ja)
Inventor
直樹 山田
淳 鎌谷
洋伸 岩脇
博揮 大類
洋祐 西出
広和 宮下
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Canon Inc
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Canon Inc
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Priority to CN202280068882.8A priority Critical patent/CN118103381A/zh
Priority to KR1020247009439A priority patent/KR20240052790A/ko
Priority to EP22880808.5A priority patent/EP4417615A4/en
Publication of WO2023063112A1 publication Critical patent/WO2023063112A1/ja
Priority to US18/629,268 priority patent/US20240298516A1/en
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Definitions

  • the organic compound of the present invention is characterized by being represented by the following general formula [1].
  • heterocyclic group a heterocyclic group having 3 or more and 27 or less carbon atoms is preferable.
  • specific examples of the substituent which the alkyl group, alkoxy group, silyl group, aryl group, and heterocyclic group may further have include those described for R 3 , but are limited to these. not to be
  • halogen atom, alkyl group, alkoxy group, silyl group, aryl group and heterocyclic group represented by R 20 to R 29 are the same as those described for R 3 , but these is not limited to As the alkyl group, an alkyl group having 1 to 10 carbon atoms is preferable. As the alkoxy group, an alkoxy group having 1 or more and 10 or less carbon atoms is preferable. As the aryl group, an aryl group having 6 or more and 30 or less carbon atoms is preferable.
  • the organic compound of this embodiment is preferably represented by the following general formula [10].
  • the organic compound of this embodiment has the following features.
  • (1-1) By having a benzofluorene ring as a ligand, the degree of orientation of the complex is high and the emission quantum yield is high.
  • (1-2) It has a low sublimation temperature and is difficult to decompose during sublimation purification.
  • (1-3) By having a benzofluorene ring as a ligand, the hole transport property is high.
  • the compound of this embodiment has a benzofluorene ring as a ligand. Condensation of one more benzene ring than the fluorene ring of the ligand of the comparative compound is thought to increase the transition dipole moment and improve the emission quantum yield.
  • Comparative Compound 3 has a high sublimation temperature and is decomposed by sublimation purification. It is considered that the sublimation temperature increased significantly due to the increase in the molecular weight due to further condensation of the benzene rings, the increase in the planarity of the ligand, and the increase in the stacking property between the complexes.
  • compound 1 suppressed the stacking property between the complexes to some extent and had a low sublimation temperature. Therefore, even if sublimation purification is performed, decomposition does not readily occur. Purification by sublimation can increase the purity, so the use of compound 1 can increase the luminous efficiency and driving durability of the organic light-emitting device. Therefore, compound 1 is superior to comparative compound 3 in luminous efficiency when used in a light-emitting layer in an organic light-emitting device.
  • the hydrogen of the pyridine ring repels R 1 and R 2 of the benzofluorene rings on both sides, especially the alkyl group, so the dihedral angle between the pyridine ring and the benzofluorene ring is fixed, and the rotational energy of the two rings is very high. , and the rotation of the bond between the pyridine ring and the benzofluorene ring is suppressed. As a result, the oscillation mode of the emission spectrum due to rotation control is suppressed, the half width of the emission spectrum is reduced, and the color purity is high.
  • Sublimability is improved when at least one of R 3 and R 20 to R 29 is a tertiary alkyl group.
  • the organic compound of the present embodiment has the above-mentioned characteristics due to having a benzofluorene ring as a ligand. Specifically, there are cases where the temperature during sublimation purification is high, and where the complex is partially decomposed after sublimation purification. Therefore, at least one of R 3 and R 20 to R 29 is preferably a tertiary alkyl group. This suppresses molecular stacking between the complexes and lowers the sublimation temperature.
  • a larger value for the bond dissociation energy indicates a stronger bond, and a smaller value indicates a weaker bond.
  • the carbon-hydrogen bond at the benzylic position is a weak bond. This is because when the hydrogen atom at the benzylic position is eliminated to form a radical, the radical is stabilized by resonance with the ⁇ electrons with the adjacent benzene ring. Therefore, the carbon-hydrogen bond at the benzylic position is a weak bond. That is, when the molecular structure does not have a structure such as a benzyl group, the resulting compound is less likely to break the carbon-hydrogen bond, which is preferable.
  • the organic compound of this embodiment has a high hole-transport property because it has a benzofluorene ring as a ligand.
  • the reason for this is thought to be that the benzofluorene rings of the ligands are likely to overlap each other, and the structure facilitates hole hopping between the ligands. Therefore, it is more preferable that the ring A side, that is, at least one of R 20 to R 29 is a tertiary alkyl group so as not to reduce the overlapping of benzofluorene rings.
  • An example compound belonging to Group E is a compound having two ligands in which a pyridine ring is attached to the 9-position of a benzofluorene ring. Since the compound has two benzofluorene rings with high planarity, the hole mobility is high and the degree of orientation of the compound is high, so that the light extraction of the light-emitting element is improved. Moreover, compared with compounds having a ligand in which a pyridine ring is bonded to the 10th or 8th position of a benzofluorene ring, the emission wavelength is longer.
  • Exemplary compounds belonging to the F group are compounds having two ligands in which a pyridine ring is bonded to the 8-position of the benzofluorene ring. Since the compound has two benzofluorene rings with high planarity, the hole mobility is high and the degree of orientation of the compound is high, so that the light extraction of the light-emitting element is improved. Since it has a broader emission spectrum than a compound having a ligand in which a pyridine ring is bonded to the 10-position of a benzofluorene ring, it can be used as a dopant for yellow-green light emission or yellow light emission for a two-color white light-emitting device.
  • Exemplary compounds belonging to Group G are compounds having one ligand in which a pyridine ring is bonded to the 10-position of a benzofluorene ring. Since the molecular weight of the complex is small, the sublimation temperature and vapor deposition temperature are low. Also, as described in (1-4), the half width of the emission spectrum is narrow.
  • An example compound belonging to the H group is a compound having one ligand in which a pyridine ring is bonded to the 9-position of a benzofluorene ring. Since the molecular weight of the complex is small, the sublimation temperature and vapor deposition temperature are low. Moreover, compared with compounds having a ligand in which a pyridine ring is bonded to the 10th or 8th position of a benzofluorene ring, the emission wavelength is longer.
  • Exemplary compounds belonging to Group I are compounds having one ligand in which a pyridine ring is bonded to the 8-position of a benzofluorene ring. Since one benzofluorene ring with high planarity is included, the hole mobility is high and the degree of orientation of the compound is high, so that the light extraction of the light-emitting element is improved. Since it has a broader emission spectrum than a compound having a ligand in which a pyridine ring is bonded to the 10-position of a benzofluorene ring, it can be used as a dopant for yellow-green light emission or yellow light emission for a two-color white light-emitting device.
  • An example compound belonging to J group is a compound having three ligands in which a pyridine ring is bonded to a benzofluorene ring. Since the compound has three benzofluorene rings with high planarity, the hole mobility is high and the degree of orientation of the compound is high, so that the light extraction of the light-emitting element is improved.
  • Exemplary compounds belonging to groups K and L are compounds having ligands in which a pyrimidine ring, an oxazole ring, or a thiazole ring is bonded to a benzofluorene ring.
  • a pyrimidine ring with a strong electron-withdrawing property it becomes a compound with a low LUMO (lowest unoccupied molecular orbital) level (far from the vacuum level). Therefore, when it is used as a light-emitting dopant in the light-emitting layer, it tends to trap electrons and has excellent balance between injection and movement of electrons and holes in the light-emitting layer.
  • the organic light-emitting device of this embodiment has at least a first electrode, a second electrode, and an organic compound layer disposed between these electrodes.
  • the first and second electrodes may be anodes and cathodes, respectively.
  • the organic compound layer may be a single layer or a multi-layer laminate as long as it has a light-emitting layer.
  • the organic compound layer includes, in addition to the light emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole/exciton blocking layer, an electron transport layer, an electron It may have an injection layer or the like.
  • the light-emitting layer may be a single layer, or may be a laminate composed of a plurality of layers.
  • the organic compound layers contains the organic compound of the present embodiment.
  • the organic compound according to the present embodiment can be any of the light emitting layer, the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole/exciton blocking layer, the electron transport layer, the electron injection layer, and the like. contained in The organic compound according to this embodiment is preferably contained in the light-emitting layer.
  • the light-emitting layer when the organic compound according to this embodiment is contained in the light-emitting layer, the light-emitting layer may be a layer composed only of the organic compound according to this embodiment. A layer composed of such an organic compound and another compound may also be used.
  • the organic compound according to the present embodiment is the first compound (hereinafter referred to as "host” or “host material”) or as a second compound (hereinafter sometimes referred to as “guest (dopant)” or “guest (dopant) material”). It may also be used as a third compound (hereinafter sometimes referred to as "assist” or “assist material”) that can be contained in the light-emitting layer.
  • the host is a compound that has the largest mass ratio among the compounds that constitute the light-emitting layer.
  • a guest is a compound having a mass ratio smaller than that of a host among the compounds constituting the light-emitting layer, and is a compound responsible for main light emission.
  • the assist material has a smaller mass ratio than the host among the compounds constituting the light-emitting layer, and has a function of assisting carrier injection and transportation of electrons and holes.
  • the concentration of the guest in the organic light-emitting device according to this embodiment is preferably 0.01% by mass or more and 30% by mass or less, and more preferably 2% by mass or more and 20% by mass or less with respect to the entire light-emitting layer. is more preferred.
  • the concentration of the assist material in the organic light-emitting device according to the present embodiment is preferably 0.1% by mass or more and 45% by mass or less, more preferably 5% by mass or more and 40% by mass or less, relative to the entire light-emitting layer. preferable.
  • the present inventors conducted various studies and found that when the organic compound according to the present embodiment is used as a host, guest, or assisting material for the light-emitting layer, particularly as a guest for the light-emitting layer, light output with high efficiency and high brightness can be obtained.
  • the inventors have found that a device can be obtained that exhibits excellent durability and has extremely high durability. Further, the present inventors have found that, when used as an assist material for the light-emitting layer, a device can be obtained that exhibits a highly efficient and highly luminous light output and has extremely high durability.
  • the light-emitting layer may be a single layer or multiple layers, and may contain multiple light-emitting materials.
  • the film formation method is vapor deposition or coating film formation. The details of this will be described in detail in the examples that will be described later.
  • the organic compound according to this embodiment can be used as a constituent material of an organic compound layer other than the light-emitting layer that constitutes the organic light-emitting device of this embodiment. Specifically, it may be used as a constituent material for an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, a hole blocking layer, and the like.
  • the compound represented by the general formula [1] When the compound represented by the general formula [1] is contained in the light-emitting layer, it has the following characteristics. (2-1) By including the compound represented by the general formula [1] as a guest material in the light-emitting layer, the interaction with the host material is strong and energy transfer is easy. (2-2) The effect of (2-1) above promotes transport hopping of holes between the guest and the host, thereby improving the hole transportability in the light-emitting layer.
  • the compound represented by the general formula [1] has, as a ligand, a benzofluorene ring, which is a condensed polycyclic ring composed of a hydrocarbon in which four rings are condensed.
  • the host material is preferably a hydrocarbon, more preferably a condensed polycyclic compound. Since the compound represented by the general formula [1] has a condensed ring structure with low polarity and aromaticity in the ligand, a hydrocarbon, preferably a condensed polycyclic group, is also introduced into the host. This facilitates ⁇ interaction between ligands of the host and guest, thereby facilitating energy transfer from the host.
  • the triplet energy used in the phosphorescent light-emitting device undergoes energy transfer by the Dexter mechanism.
  • energy transfer is performed by contact between molecules. That is, by shortening the intermolecular distance between the host material and the guest material, energy is efficiently transferred from the host material to the guest material.
  • the compound represented by the general formula [1] has a condensed ring structure with low polarity and aromaticity in the ligand. Therefore, a hydrocarbon, preferably a hydrocarbon condensed ring structure is introduced into the host to facilitate ⁇ interaction between the ligands of the host and the guest, thereby facilitating energy transfer from the host.
  • the above effect is that triplet excitons generated in the host material are quickly consumed for light emission, resulting in an organic light emitting device with high light emission efficiency.
  • the organic light-emitting device since it is possible to reduce the deterioration of the material due to the high-energy triplet excited state caused by the further excitation of the triplet excitons that are not used for light emission, the organic light-emitting device has excellent driving durability.
  • the effect of (2-1) above promotes transport hopping of holes between the guest and the host, thereby improving the hole transportability in the light-emitting layer.
  • the iridium complex represented by the general formula [1] has a HOMO (highest occupied molecular orbital) level that is low (close to the vacuum level) due to having a benzofluorene ring in the ligand, so the HOMO level is lower than that of the host material. .
  • Holes injected from the hole transport layer are transported by the host material, and the holes are transported while repeating trapping and detrapping between the iridium complex (guest) and the host. At that time, it is preferable that the host material and the iridium complex have similar skeletons.
  • an organic light-emitting device in which the voltage rise in the light-emitting layer is suppressed and the drive durability is excellent at a low voltage.
  • the organic light-emitting device of this embodiment preferably has the following characteristics.
  • the light-emitting layer contains an assist material, and the LUMO level of the assist material is lower than the LUMO level of the host material (further from the vacuum level). This confines both electron and hole carriers in the light-emitting layer, providing a highly efficient device.
  • the effect of (2-3) above is to reduce the injection of carriers through the light-emitting layer into the adjacent transport layer, and to reduce deterioration of the transport layer. offer.
  • the light-emitting layer contains an assist material, and the LUMO level of the assist material is lower than the LUMO level of the host material (further from the vacuum level).
  • the iridium complex of the present embodiment promotes the injection of holes into the light-emitting layer, it is preferable to increase the efficiency by injecting electrons and holes into the light-emitting layer in a well-balanced manner. It is preferable to promote Hydrocarbon compounds preferred as host materials tend to have broad bandgaps.
  • the LUMO level is large (close to the vacuum level), and electrons may be difficult to be injected from the electron transport layer or the hole blocking layer. Therefore, in order to facilitate the injection of electrons into the light-emitting layer, it is preferable to further include an assist material. Also, the LUMO level of the assist material is preferably lower than the LUMO level of the host material. This improves the injectability of both holes and electrons into the light-emitting layer, thereby maintaining carrier balance in the light-emitting layer and providing a highly efficient light-emitting device.
  • the effect of (2-3) above is to reduce the injection of carriers through the light-emitting layer into the adjacent transport layer, and to reduce deterioration of the transport layer.
  • the iridium complex of this embodiment promotes the hole injection property in the light-emitting layer as described above, and the effect of confining holes in the light-emitting layer by hole trapping is exhibited. . This reduces the injection of holes from the light-emitting layer into the hole blocking layer and the electron transporting layer, and reduces deterioration of the hole blocking layer and the electron transporting layer due to the holes.
  • the assist material which has a lower LUMO level than the host material, promotes electron injection and exhibits the effect of confining electrons in the light-emitting layer by electron trapping. This reduces the injection of electrons from the light-emitting layer into the electron blocking layer and the hole transport layer, and reduces deterioration of the electron blocking layer and the hole transport layer due to electrons.
  • the host material is a hydrocarbon.
  • the host material preferably has higher T 1 (lowest triplet excitation energy) than the iridium complex represented by general formula [1].
  • T1 of the host material is preferably 2.2 eV or more, more preferably 2.5 eV or more.
  • the host material is preferably a condensed polycyclic compound in order to enhance the interaction with the benzofluorene ring of the ligand of the iridium complex.
  • the condensed polycyclic group having T 1 of 2.2 eV or more includes, for example, fluoranthene, benzo[e]pyrene, benzo[g]chrysene, benzo[c]chrysene, coronene, benzofluorene, chrysene, picene , naphthalene, phenanthrene, triphenylene, and fluorene, and chrysene, picene, naphthalene, phenanthrene, triphenylene, and fluorene having a T1 of 2.5 eV or more are preferred.
  • the host material preferably has the following characteristics. (3-1) having at least one of chrysene ring, picene ring, phenanthrene ring, triphenylene ring and fluorene ring in the skeleton; (3-2) SP does not have 3 carbons.
  • the compound of this embodiment has a benzofluorene skeleton as a ligand.
  • a benzofluorene skeleton has a highly planar structure.
  • the host material preferably has a highly planar structure. This is because having a structure with high planarity allows regions with high planarity to approach each other through interaction.
  • the structure with high planarity includes, for example, a structure containing three or more condensed polycyclic rings, such as a chrysene ring, a picene ring, a phenanthrene ring, which are condensed polycyclic rings with T 1 of 2.5 eV or more,
  • a structure that is a hydrocarbon such as a triphenylene ring or a fluorene ring and contains a condensed polycyclic ring is preferable.
  • the compound of the present embodiment is a compound characterized by improving the interaction and emission properties by improving the distance from the host material.
  • the distance from the iridium complex which is the guest material, can be shortened by using a material that does not have SP3 carbon.
  • Exemplary compounds of the host compound are compounds having at least one of a triphenylene ring, a naphthalene ring, a phenanthrene ring, a chrysene ring, and a fluorene ring in the skeleton and having no SP 3 carbon. Therefore, since these compounds can be closer to the compound of the present embodiment, the interaction is strong, and they are host materials capable of favorable energy transfer to the compound of the present embodiment.
  • compounds having a triphenylene ring in the skeleton have high planarity and are particularly preferred.
  • the light-emitting layer preferably further contains an assist material.
  • the assist material is preferably a compound partially having one of the following structures.
  • X' represents either an oxygen atom, a sulfur atom, or a substituted or unsubstituted carbon atom.
  • the above structure is effective because it has electron-withdrawing properties and can reduce the LUMO level of the assist material.
  • the iridium complex represented by the general formula [1] has a high HOMO level and thus tends to trap holes easily, whereas it has a high LUMO level and tends to not easily trap electrons. Therefore, by including an assist material with a low LUMO level in the light-emitting layer, electrons are trapped in the light-emitting layer to provide an element with an appropriate carrier balance, thereby providing a high-efficiency, long-life element.
  • halogen atoms include, but are not limited to, fluorine, chlorine, bromine, and iodine.
  • alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy, 2-ethyl-octyloxy, and benzyloxy groups.
  • aryloxy groups include, but are not limited to, phenoxy groups, naphthoxy groups, and the like.
  • heteroaryloxy groups include, but are not limited to, furanyloxy groups and thienyloxy groups.
  • aryl groups include phenyl, naphthyl, indenyl, biphenyl, terphenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, anthranyl, perylenyl, chrysenyl, and fluoranthenyl groups. Examples include, but are not limited to.
  • heterocyclic groups include pyridyl, pyrimidyl, pyrazyl, triazyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, Carbazolyl group, acridinyl group, phenanthrolyl group and the like can be mentioned, but not limited to these.
  • silyl group examples include, but are not limited to, a trimethylsilyl group, a triphenylsilyl group, and the like.
  • amino groups include 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-dibenzylamino 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-dianisolylamino group, N-mesityl-N-phenylamino group, N,N-dimesitylamino group, N-phenyl-N-(4-tertiarybutylphenyl)amino group, N-
  • substituents that the alkyl group, alkoxy group, aryloxy group, heteroaryloxy group, aryl group, heterocyclic group, silyl group, and amino group may further have include deuterium, methyl group, and ethyl group.
  • Alkyl groups such as normal propyl group, isopropyl group, normal butyl group and tertiary butyl group, aralkyl groups such as benzyl group, aryl groups such as phenyl group and biphenyl group, heterocyclic groups such as pyridyl group and pyrrolyl group, dimethyl Amino groups such as amino group, diethylamino group, dibenzylamino group, diphenylamino group and ditolylamino group, alkoxy groups such as methoxy group, ethoxy group and propoxy group, aryloxy groups such as phenoxy group, fluorine, chlorine, bromine and iodine Halogen atoms such as, cyano groups, etc., but are not limited to these.
  • the light-emitting device of the present embodiment includes, if necessary, conventionally known low-molecular-weight and high-molecular-weight hole-injecting compounds or hole-transporting compounds, host compounds, and light-emitting compounds.
  • An electron-injecting compound, an electron-transporting compound, or the like can be used together. Examples of these compounds are given below.
  • HT16 to HT18 can reduce the driving voltage by using them in the layer in contact with the anode.
  • HT16 is widely used in organic light emitting devices.
  • HT2 to HT6, HT10, and HT12 may be used for the organic compound layer adjacent to HT16. Further, a plurality of materials may be used for one organic compound layer.
  • light-emitting dopants include condensed ring compounds (eg, fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.), quinacridone derivatives, coumarin derivatives, stilbene derivatives, tris(8-quinolinolato)aluminum.
  • condensed ring compounds eg, fluorene derivatives, naphthalene derivatives, pyrene derivatives, perylene derivatives, tetracene derivatives, anthracene derivatives, rubrene, etc.
  • quinacridone derivatives eg, coumarin derivatives, stilbene derivatives, tris(8-quinolinolato)aluminum.
  • organoaluminum complexes such as poly(phenylenevinylene) derivatives, poly(fluorene) derivatives, and poly(phenylene) derivatives.
  • specific examples of the compound used as the light-emitting material are shown below, but are of course not limited to these.
  • the luminescent material is a hydrocarbon compound
  • a hydrocarbon compound is a compound composed only of carbon and hydrogen, and corresponds to BD7, BD8, GD5 to GD9, RD1.
  • the light-emitting material is a condensed polycyclic ring containing a five-membered ring, it is more preferable because it has a high ionization potential, is resistant to oxidation, and provides an element with a long life.
  • BD7, BD8, GD5 to GD9, RD1 correspond.
  • Examples of the host material or assist material include aromatic hydrocarbon compounds or derivatives thereof, carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, organic aluminum complexes such as tris(8-quinolinolato)aluminum, and organic beryllium complexes. be done. Specific examples of the compound are shown below, but are of course not limited to these.
  • a hydrocarbon compound is a compound composed only of carbon and hydrogen, and corresponds to EM1 to EM12 and EM16 to EM27.
  • the electron-transporting material can be arbitrarily selected from those capable of transporting electrons injected from the cathode to the light-emitting layer, and is selected in consideration of the balance with the hole mobility of the hole-transporting material.
  • Materials having electron transport properties include oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, quinoxaline derivatives, phenanthroline derivatives, organoaluminum complexes, condensed ring compounds (e.g., fluorene derivatives, naphthalene derivatives, chrysene derivatives, anthracene derivatives, etc.).
  • the above electron-transporting materials are also suitably used for the hole blocking layer. Specific examples of the compound that can be used as the electron-transporting material are shown below, but are of course not limited to these.
  • the electron-injecting material can be arbitrarily selected from those that allow electrons to be easily injected from the cathode, and is selected in consideration of the balance with the hole-injecting property.
  • Organic compounds also include n-type dopants and reducing dopants. Examples thereof include compounds containing alkali metals such as lithium fluoride, lithium complexes such as lithium quinolinol, benzimidazolidene derivatives, imidazolidene derivatives, fulvalene derivatives and acridine derivatives.
  • An organic light-emitting device is provided by forming an insulating layer, a first electrode, an organic compound layer, and a second electrode on a substrate.
  • a protective layer, color filters, microlenses, etc. may be provided over the second electrode.
  • a planarization layer may be provided between it and the protective layer.
  • the planarizing layer can be made of acrylic resin or the like. The same applies to the case where a flattening layer is provided between the color filter and the microlens.
  • substrates examples include quartz, glass, silicon wafers, resins, and metals.
  • a switching element such as a transistor and wiring may be provided on the substrate, and an insulating layer may be provided thereon. Any material can be used for the insulating layer as long as a contact hole can be formed between the insulating layer and the first electrode, and insulation from unconnected wiring can be ensured.
  • a resin such as polyimide, silicon oxide, silicon nitride, or the like can be used.
  • a pair of electrodes can be used as the electrodes.
  • the pair of electrodes may be a first electrode and a second electrode, respectively an anode and a cathode.
  • the electrode with the higher potential is the anode, and the other is the cathode. It can also be said that the electrode that supplies holes to the light-emitting layer is the anode, and the electrode that supplies electrons is the cathode.
  • a material with a work function that is as large as possible is good for the constituent material of the anode.
  • simple metals such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, tungsten, mixtures containing these, or alloys combining these, tin oxide, zinc oxide, indium oxide, tin oxide Metal oxides such as indium (ITO) and zinc indium oxide can be used.
  • Conductive polymers such as polyaniline, polypyrrole and polythiophene can also be used.
  • the anode may be composed of a single layer, or may be composed of a plurality of layers.
  • Photolithography technology can be used to form the electrodes.
  • a material with a small work function is preferable as a constituent material of the cathode.
  • alkali metals such as lithium, alkaline earth metals such as calcium, simple metals such as aluminum, titanium, manganese, silver, lead, and chromium, or mixtures thereof may be used.
  • alloys obtained by combining these simple metals can also be used.
  • magnesium-silver, aluminum-lithium, aluminum-magnesium, silver-copper, zinc-silver and the like can be used.
  • Metal oxides such as indium tin oxide (ITO) can also be used. These electrode materials may be used singly or in combination of two or more.
  • the organic compound layer may be formed of a single layer or multiple layers. When it has multiple layers, it may be called a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, or an electron injection layer, depending on its function.
  • the organic compound layer is mainly composed of organic compounds, but may contain inorganic atoms and inorganic compounds. For example, it may have copper, lithium, magnesium, aluminum, iridium, platinum, molybdenum, zinc, and the like.
  • the organic compound layer may be arranged between the first electrode and the second electrode, and may be arranged in contact with the first electrode and the second electrode.
  • a protective layer may be provided over the second electrode. For example, by adhering glass provided with a desiccant on the second electrode, it is possible to reduce the penetration of water or the like into the organic compound layer, thereby reducing the occurrence of display defects.
  • a passivation film such as silicon nitride may be provided on the second electrode to reduce penetration of water or the like into the organic compound layer.
  • a protective layer may be provided using an atomic deposition method (ALD method) after film formation by the CVD method.
  • the material of the film formed by the ALD method is not limited, but may be silicon nitride, silicon oxide, aluminum oxide, or the like. Silicon nitride may be further formed by CVD on the film formed by ALD.
  • a film formed by the ALD method may have a smaller film thickness than a film formed by the CVD method. Specifically, it may be 50% or less, further 10% or less.
  • a color filter may be provided on the protective layer.
  • a color filter considering the size of the organic light-emitting element may be provided on another substrate and then bonded to the substrate provided with the organic light-emitting element.
  • a color filter may be patterned.
  • the color filters may be composed of polymers.
  • a planarization layer may be provided between the color filter and the protective layer.
  • the planarization layer is provided for the purpose of reducing unevenness of the underlying layer. Without limiting its purpose, it may also be referred to as a material resin layer.
  • the planarization layer may be composed of an organic compound, and may be a low-molecular or high-molecular compound, preferably a high-molecular compound.
  • the planarization layer may be provided above and below the color filter, and the constituent materials thereof may be the same or different.
  • Specific examples include polyvinylcarbazole resin, polycarbonate resin, polyester resin, ABS resin, acrylic resin, polyimide resin, phenol resin, epoxy resin, silicon resin, urea resin, and the like.
  • An organic light-emitting element or organic light-emitting device may have an optical member such as a microlens on its light emitting side.
  • the microlenses may be made of acrylic resin, epoxy resin, or the like.
  • the purpose of the microlens may be to increase the amount of light extracted from the organic light-emitting element or organic light-emitting device and to control the direction of the extracted light.
  • the microlens may have a hemispherical shape.
  • a counter substrate may be provided over the planarization layer.
  • the counter substrate is called the counter substrate because it is provided at a position corresponding to the substrate described above.
  • the constituent material of the counter substrate may be the same as that of the aforementioned substrate.
  • the opposing substrate may be the second substrate when the substrate described above is the first substrate.
  • the pixels can take a known arrangement form in a plan view.
  • it may be a stripe arrangement, a delta arrangement, a pentile arrangement, or a Bayer arrangement.
  • the shape of the sub-pixel in plan view may take any known shape.
  • a rectangle, a square such as a rhombus, a hexagon, and the like Of course, if it is not an exact figure but has a shape close to a rectangle, it is included in the rectangle.
  • a combination of sub-pixel shapes and pixel arrays can be used.
  • 2A and 2B are cross-sectional schematic diagrams showing an example of a display device having an organic light-emitting element and a transistor connected to the organic light-emitting element.
  • a transistor is an example of an active device.
  • the transistors may be thin film transistors (TFTs).
  • the protective layer 6 reduces penetration of moisture into the organic compound layer 4 .
  • the protective layer 6 is shown as one layer, it may be multiple layers. Each layer may have an inorganic compound layer and an organic compound layer.
  • the method of electrical connection between the electrodes (anode 21, cathode 23) included in the organic light-emitting element 26 and the electrodes (source electrode 17, drain electrode 16) included in the TFT 18 is limited to the mode shown in FIG. 2B. isn't it. In other words, either the anode 21 or the cathode 23 and either the source electrode 17 or the drain electrode 16 of the TFT 18 may be electrically connected.
  • TFT refers to a thin film transistor.
  • the organic compound layer 22 may be multiple layers.
  • a first protective layer 24 and a second protective layer 25 are provided on the cathode 23 to reduce deterioration of the organic light-emitting element 26 .
  • transistors are used as switching elements in the display device 100 of FIG. 2B, other switching elements may be used instead.
  • FIG. 3 is a schematic diagram showing an example of the display device according to this embodiment.
  • Display device 1000 may have touch panel 1003 , display panel 1005 , frame 1006 , circuit board 1007 , and battery 1008 between upper cover 1001 and lower cover 1009 .
  • the touch panel 1003 and display panel 1005 are connected to flexible printed circuits FPC 1002 and 1004 .
  • Transistors are printed on the circuit board 1007 .
  • the battery 1008 may not be provided if the display device is not a portable device, or may be provided at another position even if the display device is a portable device.
  • the display device may have color filters having red, green, and blue.
  • the color filters may be arranged in a delta arrangement of said red, green and blue.
  • the display device may be used in the display section of a mobile terminal. In that case, it may have both a display function and an operation function.
  • Mobile terminals include mobile phones such as smart phones, tablets, head-mounted displays, and the like.
  • a display device using the organic light-emitting device of this embodiment Since the best time to take an image is a short amount of time, it is better to display the information as soon as possible. Therefore, it is preferable to use a display device using the organic light-emitting device of this embodiment. This is because the organic light emitting device has a high response speed.
  • a display device using an organic light-emitting element can be used more preferably than these devices and a liquid crystal display device, which require a high display speed.
  • the imaging device 1100 has an optical unit (not shown).
  • the optical unit has a plurality of lenses and forms an image on the imaging device housed in the housing 1104 .
  • the multiple lenses can be focused by adjusting their relative positions. This operation can also be performed automatically.
  • An imaging device may be called a photoelectric conversion device.
  • the photoelectric conversion device can include, as an imaging method, a method of detecting a difference from a previous image, a method of extracting from an image that is always recorded, and the like, instead of sequentially imaging.
  • FIG. 5A and 5B are schematic diagrams showing an example of the display device according to the present embodiment.
  • FIG. 5A shows a display device such as a television monitor or a PC monitor.
  • a display device 1300 has a frame 1301 and a display portion 1302 .
  • the light-emitting element according to this embodiment may be used for the display portion 1302 .
  • It has a frame 1301 and a base 1303 that supports the display portion 1302 .
  • the base 1303 is not limited to the form of FIG. 5A.
  • the lower side of the frame 1301 may also serve as the base.
  • the frame 1301 and the display portion 1302 may be curved. Its radius of curvature may be between 5000 mm and 6000 mm.
  • FIG. 5B is a schematic diagram showing another example of the display device according to this embodiment.
  • a display device 1310 in FIG. 5B is configured to be foldable, and is a so-called foldable display device.
  • the display device 1310 has a first display portion 1311 , a second display portion 1312 , a housing 1313 and a bending point 1314 .
  • the first display portion 1311 and the second display portion 1312 may have the light emitting element according to this embodiment.
  • the first display portion 1311 and the second display portion 1312 may be a seamless display device.
  • the first display portion 1311 and the second display portion 1312 can be separated at a bending point.
  • the first display unit 1311 and the second display unit 1312 may display different images, or the first and second display units may display one image.
  • FIG. 6A is a schematic diagram showing an example of the lighting device according to this embodiment.
  • the illumination device 1400 may have a housing 1401 , a light source 1402 , a circuit board 1403 , an optical filter 1404 that transmits light emitted by the light source 1402 , and a light diffusion section 1405 .
  • the light source 1402 may comprise an organic light emitting device according to this embodiment.
  • Optical filter 1404 may be a filter that enhances the color rendering of the light source.
  • the light diffusing portion 1405 can effectively diffuse light from a light source such as light-up and deliver the light over a wide range.
  • the optical filter 1404 and the light diffusion section 1405 may be provided on the light emission side of the illumination. If necessary, a cover may be provided on the outermost part.
  • FIG. 6B is a schematic diagram of an automobile, which is an example of a moving object according to this embodiment.
  • the automobile has a tail lamp, which is an example of a lamp.
  • the automobile 1500 may have a tail lamp 1501, and may be configured to turn on the tail lamp when a brake operation or the like is performed.
  • the tail lamp 1501 may have the organic light emitting device according to this embodiment.
  • the tail lamp 1501 may have a protective member that protects the organic light emitting elements.
  • the protective member may be made of any material as long as it has a certain degree of strength and is transparent, but is preferably made of polycarbonate or the like. A furandicarboxylic acid derivative, an acrylonitrile derivative, or the like may be mixed with the polycarbonate.
  • a car 1500 may have a body 1503 and a window 1502 attached thereto.
  • 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 comprise an organic light emitting device according to the present embodiments.
  • the constituent materials such as the electrodes of the organic light-emitting element are made of transparent members.
  • a mobile object may be a ship, an aircraft, a drone, or the like.
  • the moving body may have a body and a lamp provided on the body.
  • the lighting device may emit light to indicate the position of the aircraft.
  • the lamp has the organic light-emitting element according to this embodiment.
  • FIG. 7A is a schematic diagram showing an example of a wearable device according to one embodiment of the present invention. Glasses 1600 (smart glasses) according to one application example will be described with reference to FIG. 7A.
  • An imaging device 1602 such as a CMOS sensor or SPAD is provided on the surface side of lenses 1601 of spectacles 1600 . Further, the display device of each embodiment described above is provided on the rear surface side of the lens 1601 .
  • the spectacles 1600 further include a control device 1603 .
  • the control device 1603 functions as a power source that supplies power to the imaging device 1602 and the display device. Also, the control device 1603 controls operations of the imaging device 1602 and the display device.
  • the lens 1601 is formed with an optical system for condensing light onto the imaging device 1602 .
  • FIG. 7B is a schematic diagram showing another example of the wearable device according to one embodiment of the present invention.
  • Glasses 1610 (smart glasses) according to one application example will be described with reference to FIG. 7B.
  • the glasses 1610 have a control device 1612, and the control device 1612 is equipped with an imaging device corresponding to the imaging device 1602 in FIG. 7A and a display device.
  • An imaging device in the control device 1612 and an optical system for projecting light emitted from the display device are formed in the lens 1611 , and an image is projected onto the lens 1611 .
  • the control device 1612 functions as a power source that supplies power to the imaging device and the display device, and controls the operation of the imaging device and the display device.
  • the control device 1612 may have a line-of-sight detection unit that detects the line of sight of the wearer. Infrared rays may be used for line-of-sight detection.
  • the infrared light emitting section emits infrared light to the eyeballs of the user who is gazing at the displayed image.
  • a captured image of the eyeball is obtained by detecting reflected light of the emitted infrared light from the eyeball by an imaging unit having a light receiving element.
  • a reduction means for reducing light from the infrared light emitting section to the display section in plan view deterioration in image quality is reduced.
  • the line of sight of the user with respect to the display image is detected from the captured image of the eye obtained by imaging the infrared light.
  • any known method can be applied to line-of-sight detection using captured images of eyeballs.
  • a line-of-sight detection method based on a Purkinje image obtained by reflection of irradiation light on the cornea.
  • line-of-sight detection processing based on the pupillary corneal reflection method is performed.
  • the user's line of sight is detected by calculating a line-of-sight vector representing the orientation (rotational angle) of the eyeball based on the pupil image and the Purkinje image included in the captured image of the eyeball using the pupillary corneal reflection method.
  • a display device may have an imaging device having a light-receiving element, and may control a display image of the display device based on user's line-of-sight information from the imaging device. Specifically, the display device determines, based on the line-of-sight information, a first visual field area that the user gazes at, and a second visual field area other than the first visual field area. The first viewing area and the second viewing area may be determined by the control device of the display device, or may be determined by an external control device. In the display area of the display device, the display resolution of the first viewing area may be controlled to be higher than the display resolution of the second viewing area. That is, the resolution of the second viewing area may be lower than that of the first viewing area.
  • the display area has a first display area and a second display area different from the first display area. is determined.
  • the first viewing area and the second viewing area may be determined by the control device of the display device, or may be determined by an external control device.
  • the resolution of areas with high priority may be controlled to be higher than the resolution of areas other than areas with high priority. That is, the resolution of areas with relatively low priority may be lowered.
  • AI may be used to determine the first field of view area and areas with high priority.
  • the AI is a model configured to estimate the angle of the line of sight from the eyeball image and the distance to the object ahead of the line of sight, using the image of the eyeball and the direction in which the eyeball of the image was actually viewed as training data. It's okay.
  • the AI program may be possessed by the display device, the imaging device, or the external device. If the external device has it, it is communicated to the display device via communication.
  • display control When display control is performed based on visual recognition detection, it can be preferably applied to smart glasses that further have an imaging device that captures an image of the outside. Smart glasses can display captured external information in real time.
  • FIG. 8A is a schematic diagram showing an example of an image forming apparatus according to an embodiment of the invention.
  • the image forming apparatus 40 is an electrophotographic image forming apparatus, and includes a photoreceptor 27 , an exposure light source 28 , a charging section 30 , a developing section 31 , a transfer device 32 , a conveying roller 33 and a fixing device 35 .
  • Light 29 is emitted from an exposure light source 28 to form an electrostatic latent image on the surface of the photoreceptor 27 .
  • This exposure light source 28 has the organic light emitting device according to this embodiment.
  • the development unit 31 has toner and the like.
  • the charging section 30 charges the photoreceptor 27 .
  • a transfer device 32 transfers the developed image to a recording medium 34 .
  • a transport roller 33 transports the recording medium 34 .
  • the recording medium 34 is, for example, paper.
  • a fixing device 35 fixes the image formed on the recording medium 34 .
  • FIGS. 8B and 8C are diagrams showing the exposure light source 28, and are schematic diagrams showing how a plurality of light emitting units 36 are arranged on an elongated substrate.
  • An arrow 37 is parallel to the axis of the photoreceptor and represents the column direction in which the organic light emitting elements are arranged.
  • the row direction is the same as the direction of the axis around which the photoreceptor 27 rotates. This direction can also be called the longitudinal direction of the photoreceptor 27 .
  • FIG. 8B shows a form in which the light emitting section 36 is arranged along the longitudinal direction of the photoreceptor 27 .
  • FIG. 8C is a form different from FIG.
  • reaction solution was cooled to ⁇ 78° C., and 16.0 ml (25.0 mmol) of n-BuLi (hexane solution 1.56 M) was added dropwise. After stirring for 30 minutes, ZnCl 2 (2-methyltetrahydrofuran solution 2.0 M)) (15.0 mL, 30.0 mmol.) was added and stirred for 15 minutes. Thereafter, the reaction solution was returned to room temperature, f-2 of 2.27 g (20.0 mmol) and Pd(PPh 3 ) 4 of 578 mg were added and heated with stirring at 80° C. for 18 hours. After completion of the reaction, the mixture was extracted with toluene, and the organic layer was concentrated to dryness. The obtained solid was purified by silica gel column chromatography (toluene:ethyl acetate mixture) to obtain 0.77 g of transparent solid (f-3) (yield: 12%).
  • Example 30 (synthesis of exemplary compound D-16)]
  • Exemplary compound D-16 was synthesized according to the following scheme.
  • Intermediate f-4 was synthesized in the same manner as in Example 1 using starting material f-3.
  • Examples 31 to 35 (synthesis of exemplary compounds)
  • Table 8 the exemplary compounds shown in Examples 31 to 35 were exemplified in the same manner as in Example 30 except that the raw material f-3 in Example 30 was changed to the raw material 1 and the raw material f-7 was changed to the raw material 2.
  • a compound was synthesized.
  • m/z which is the actual measurement result of mass spectrometry measured in the same manner as in Example 30, is shown.
  • an ITO electrode (anode) was formed by forming a film of ITO on a glass substrate and subjecting it to desired patterning. At this time, the film thickness of the ITO electrode was set to 100 nm. The substrate on which the ITO electrodes were formed in this manner was used as an ITO substrate in the following steps. Next, vacuum deposition was performed by resistance heating in a vacuum chamber at 1.3 ⁇ 10 ⁇ 4 Pa to continuously form organic compound layers and electrode layers shown in Table 10 on the ITO substrate. At this time, the electrode area of the facing electrodes (metal electrode layer, cathode) was set to 3 mm 2 .
  • the characteristics of the obtained device were measured and evaluated.
  • the efficiency of the light emitting device was 66 cd/A.
  • a continuous driving test was performed at a current density of 50 mA/cm 2 to measure the time when the luminance deterioration rate reached 5%.
  • the time required for the luminance deterioration rate to reach 5% is shown as a ratio when the time in this example is set to 1.0.
  • the measuring device specifically measured the current-voltage characteristics with a Hewlett-Packard Micro Ammeter 4140B, and the luminance was measured with a Topcon BM7.
  • Example 41 to 47 An organic light-emitting device was produced in the same manner as in Example 40, except that the materials shown in Table 11 were changed as appropriate.
  • Compound Q-2-1 is the following compound.
  • Example 40 The obtained element was evaluated in the same manner as in Example 40.
  • the time required for the luminance deterioration rate to reach 5% is shown as a ratio when the time for Example 40 is set to 1.0.
  • Table 11 shows the measurement results.
  • Example 49 The resulting device was evaluated in the same manner as in Example 40.
  • the efficiency of the light emitting device was 66 cd/A.
  • the time required for the luminance deterioration rate to reach 5% is indicated by the ratio when the time in this example is set to 1.0.
  • Example 49 to 56 An organic light-emitting device was produced in the same manner as in Example 48, except that the materials shown in Table 13 were changed as appropriate. The resulting device was evaluated in the same manner as in Example 48. The time when the luminance deterioration rate reaches 5% is indicated by the ratio when the time when the luminance deterioration rate of Example 48 reaches 5% is set to 1.0. Table 13 shows the measurement results.

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