Boron compound and organic light-emitting device comprising same

Abstract

The present specification relates to a boron compound represented by chemical formula 1 and an organic light-emitting device comprising same, and provides a boron compound having excellent color purity due to a narrow full width at half maximum, and an organic light emitting device comprising same.

Description

Boron compounds and organic light-emitting devices containing the same

[0001] The present disclosure relates to a boron compound and an organic light-emitting device comprising the same, and more particularly, to a compound having excellent color purity or a compound having excellent color purity while exhibiting thermally activated delayed fluorescence (TADF) characteristics, and an organic light-emitting device comprising the same.

[0002] Organic light emitting diodes (OLEDs) are devices that utilize organic light emitting diodes (OLEDs) to create a device that emits light when electrical energy is applied. These devices utilize organic light emitting diodes (AEDs) by interposing an organic material between the anode and the cathode. These devices typically include multiple organic layers to enhance efficiency and stability, and are typically composed of a hole injection layer (HIL), a hole transport layer (HTL), an emitting layer (EL), an electron transport layer (ETL), and an electron injection layer (EIL).

[0003] Materials used as organic layers can be classified into light-emitting materials and charge transport materials according to their functions, and the light-emitting materials can be classified into fluorescent materials that utilize the fluorescence phenomenon derived from the singlet excited state of electrons and phosphorescent materials that utilize the phosphorescence phenomenon derived from the triplet excited state according to the light-emitting mechanism.

[0004] Furthermore, luminescent materials can be categorized into blue, green, and red luminescent materials based on their emission color. Phosphorescent materials for colors other than blue have been developed and are being used industrially. However, while high efficiency can be achieved using phosphorescent materials utilizing heavy metals, the heavy metals required to realize phosphorescence cause charge transfer between the metal and the organic material, limiting their wide half-width. Therefore, efforts are needed to reduce the half-width for both blue and green materials.

[0005] Delayed fluorescent materials must have a small overlap between the Highest Occupied Molecular Orbital (HOMO) and the Lowest Unoccupied Molecular Orbital (LUMO) to minimize the energy difference between singlets and triplet atoms. To achieve this, a donor-acceptor structure is commonly used, which allows for intramolecular charge transfer. However, when compounds with conventional donor-acceptor structures are applied as delayed fluorescent materials, the emission wavelength shifts to the long wavelength region, and the emission spectrum is broad, resulting in reduced color purity.

[0006] To overcome these shortcomings, MR-TADF materials that exhibit multi-resonance (MR) effects and delayed fluorescence (TADF) characteristics are being extensively studied. The chemical formula a below is 'CzBN', a structure widely used as MR-TADF.

[0007] [chemical formula a]

[0008]

[0009] While the conventional donor-acceptor structure delayed fluorescent material reduced the HOMO and LUMO overlap by donor and acceptor unit units, MR-TADF separated the HOMO and LUMO overlap by rigid intramolecular atomic units, and in addition, when the molecule is excited by light or electricity, the degree of molecular distortion is almost zero, so it can obtain a narrow half-width characteristic. However, in the case of the conventional MR-TADF, there is a disadvantage that the flat molecular structure in which the ring structure is firmly bound easily causes intermolecular packing, which shifts to a longer wavelength when in a thin film state compared to a solution state or the half-width characteristic broadens, resulting in poor color purity. For example, in the case of the above chemical formula a, in the solution state, it showed a blue emission of 473 nm and a half width of 25 nm, but in the film state doped with 1% mCBP, it shifted to a 12 nm longer wavelength (485 nm) due to agglomeration, and the blue purity decreased, and in the case of a neat film, it emitted green light with weak single molecule emission at 502 nm and strong eximer emission at 570 nm.

[0010] The present specification is intended to solve the problems of the prior art described above, and one purpose of the present specification is to provide a boron compound having excellent color purity.

[0011] Another object of the present specification is to provide an organic light-emitting device comprising a compound having excellent color purity.

[0012] Another object of the present specification is to provide a delayed fluorescence or phosphorescent photosensitive superfluorescent device exhibiting high efficiency and high color purity characteristics by using a compound having excellent color purity.

[0013] According to one aspect, a boron compound represented by the following chemical formula 1 is provided.

[0014] [Chemical Formula 1]

[0015]

[0016] In the above chemical formula 1, R1 to R 10 are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted arylheteroarylamino group, R6 and R7 may be adjacent to each other and connected to each other in a ring, R8 and R9 may be adjacent to each other and connected to each other in a ring, and at least one of R1 to R3 is represented by the following chemical formula 2.

[0017] [Chemical Formula 2]

[0018]

[0019] In the above chemical formula 2, R 11 and R 12 are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted arylheteroarylamino group, and R 11 and R 12 At least one of them is not hydrogen or deuterium, n1 and n2 are each independently an integer from 1 to 4, and Y1 and Y2 are each independently hydrogen, deuterium, or an alkyl group, or are bonded to each other to form a ring.

[0020] In one embodiment, the boron compound may be represented by any one of the following chemical formulae 1-1 to 1-68.

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034] In one embodiment, the emission spectrum of the boron compound may have a peak at 450 to 600 nm.

[0035] In one embodiment, the half-width of the boron compound may be 40 nm or less.

[0036] In one embodiment, the energy difference between the singlet and triplet of the boron compound may be 0.20 eV or less.

[0037] In one embodiment, the photoluminescence quantum yield (PLQY) of the boron compound may be 90% or greater.

[0038] According to another aspect, an organic light-emitting device is provided, comprising: a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers interposed between the first electrode and the second electrode; wherein at least one of the organic layers comprises one or more of the aforementioned boron compounds.

[0039] In one embodiment, the first electrode is an anode, the second electrode is a cathode, and the organic layer may include: a light-emitting layer including at least one of the aforementioned boron compounds; a hole transport region interposed between the first electrode and the light-emitting layer and including at least one of a hole injection layer, a hole transport layer, and an electron blocking layer; and an electron transport region interposed between the light-emitting layer and the second electrode and including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.

[0040] In one embodiment, the organic layer may include an emitting layer comprising one or more host compounds; a delayed fluorescent compound or a phosphorescent compound; and the boron compound described above.

[0041] In one embodiment, the maximum external quantum efficiency (EQE) of the organic light-emitting device may be 15% or greater.

[0042] A boron compound according to one aspect of the present specification exhibits multiple resonance effects and can exhibit excellent color purity due to a narrow half-width.

[0043] An organic light-emitting device according to another aspect of the present specification can exhibit excellent color purity by including the aforementioned boron compound.

[0044] According to another aspect of the present disclosure, an organic light-emitting device is a delayed fluorescent or phosphorescent photosensitive superfluorescent device including a compound having a narrow half-width, excellent color purity, and a small energy difference between a singlet and a triplet, and can exhibit high efficiency and high color purity characteristics.

[0045] It should be understood that the effects of one aspect of this specification are not limited to the effects described above, but include all effects that can be inferred from the detailed description or claims of this specification.

[0046] Figure 1 shows the UV-Vis absorption spectrum and room temperature photoluminescence (RTPL) spectrum of compound 1-8 according to one embodiment of the present specification.

[0047] FIG. 2 shows the UV-Vis absorption spectrum and room temperature photoluminescence (RTPL) spectrum of compound 1-39 according to one embodiment of the present specification.

[0048] FIG. 3 shows the room temperature photoluminescence (RTPL) spectrum and low temperature photoluminescence (LTPL) spectrum of compound 1-8 according to one embodiment of the present specification.

[0049] FIG. 4 shows the electroluminescence spectrum of a delayed fluorescent device comprising compound 1-8 (BpIC-DPA) or compound 1-39 (BpIC-Cz) according to one embodiment of the present disclosure.

[0050] FIG. 5 shows the electroluminescence spectra of a phosphorescent organic light-emitting device (PHOLED) that does not contain a boron compound and a phosphorescent photosensitive superfluorescent device containing compound 1-8 (BpIC-DPA) or compound 1-39 (BpIC-Cz) according to an embodiment of the present disclosure.

[0051] Hereinafter, aspects of this specification will be described with reference to the attached drawings. However, the contents of this specification may be implemented in various different forms and are therefore not limited to the embodiments described herein. Furthermore, in the drawings, irrelevant parts have been omitted to clearly illustrate aspects of this specification, and similar parts have been designated with similar drawing reference numerals throughout the specification.

[0052] Throughout the specification, when a part is said to be "connected" to another part, this includes not only "directly connected" but also "indirectly connected" with other elements intervening. Furthermore, when a part is said to "include" a component, this does not exclude other components, but rather implies that the other components may be included, unless otherwise specifically stated.

[0053] When a range of numerical values ​​is stated herein, unless the specific range is otherwise specified, the values ​​have the precision of the significant figures provided according to the standard rules in chemistry for significant figures. For example, the number 10 includes the range of 5.0 to 14.9, and the number 10.0 includes the range of 9.50 to 10.49.

[0054] Hereinafter, one embodiment of the present specification will be described in detail with reference to the attached drawings.

[0055] boron compounds

[0056] A boron compound according to one aspect of the present specification is represented by the following chemical formula 1.

[0057] [Chemical Formula 1]

[0058]

[0059] In the above chemical formula 1, R1 to R 10are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted arylheteroarylamino group, R6 and R7 may be adjacent to each other and connected to each other in a ring, R8 and R9 may be adjacent to each other and connected to each other in a ring, and at least one of R1 to R3 is represented by the following chemical formula 2.

[0060] [Chemical Formula 2]

[0061]

[0062] In the above chemical formula 2, R 11 and R 12 are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted arylheteroarylamino group, and R 11 and R 12 At least one of them is not hydrogen or deuterium, n1 and n2 are each independently an integer from 1 to 4, and Y1 and Y2 are each independently hydrogen, deuterium, or an alkyl group, or are bonded to each other to form a ring.

[0063] The term 'alkyl group' used in this specification refers to a group having 1 to 60 carbon atoms (C1 to C 60) can mean a straight or branched alkyl group. An unsubstituted alkyl group means an alkyl group composed only of carbon and hydrogen, and a substituted alkyl group means that at least one of the carbons constituting the alkyl group is replaced with an atom other than carbon. Such substituted atoms include, but are not limited to, nitrogen, sulfur, oxygen, silicon, and halogen elements.

[0064] The term 'cycloalkyl group' used in this specification refers to a group having 3 to 60 carbon atoms (C3~C 60 ) may mean an alkyl group including at least one cyclic structure. An unsubstituted cycloalkyl group means an alkyl group composed only of carbon and hydrogen, and a substituted cycloalkyl group means one in which at least one of the carbons constituting the cycloalkyl group is replaced with an atom other than carbon. Such substituted atoms include, but are not limited to, nitrogen, sulfur, oxygen, silicon, and halogen elements.

[0065] The term 'alkoxy group' used in this specification refers to a group having 1 to 60 carbon atoms (C1 to C 60 ) may mean that oxygen is bonded to the terminal of a straight or branched alkyl group. An unsubstituted alkoxy group means that oxygen is bonded to the terminal of an alkyl group composed only of carbon and hydrogen, and a substituted alkoxy group means that at least one of the carbons constituting the alkoxy group is replaced with an atom other than carbon. Such substituted atoms include, but are not limited to, nitrogen, sulfur, oxygen, silicon, and halogen elements.

[0066] The term 'silyl group' used in this specification refers to a group having 1 to 60 carbon atoms (C1 to C 60) may mean that silicon is bonded to the terminal of a straight or branched alkyl group. An unsubstituted silyl group means that silicon is bonded to the terminal of an alkyl group composed only of carbon and hydrogen, and a substituted silyl group means that at least one of the carbons constituting the silyl group is replaced with an atom other than carbon. Such substituted atoms include, but are not limited to, nitrogen, sulfur, oxygen, silicon, and halogen elements.

[0067] The term 'amine group' used in this specification refers to a group having 1 to 60 carbon atoms (C1 to C 60 ) may mean that nitrogen is bonded to the terminal of a straight or branched alkyl group. An unsubstituted amine group means that nitrogen is bonded to the terminal of an alkyl group composed only of carbon and hydrogen, and a substituted amine group means that at least one of the carbons constituting the amine group is replaced with an atom other than carbon. Such substituted atoms include, but are not limited to, nitrogen, sulfur, oxygen, silicon, and halogen elements.

[0068] The term 'aryl group' used in this specification refers to a group having 6 to 60 carbon atoms (C6 to C 60 ) may mean a functional group including at least one aromatic compound structure. An unsubstituted aryl group means an aryl group composed only of carbon and hydrogen, and a substituted aryl group means that at least one carbon among the carbons constituting the aryl group that does not constitute an aromatic compound structure is replaced with another atom. Such substituted atoms include, but are not limited to, nitrogen, sulfur, oxygen, silicon, and halogen elements.

[0069] The term 'heteroaryl group' as used herein refers to a heteroaryl group having 1 to 60 carbon atoms (C1 to C10) containing at least one aromatic compound structure in which at least one carbon is replaced by another atom. 60) can mean a functional group. An unsubstituted heteroaryl group means a functional group in which a substituted aromatic compound structure is connected only with carbon and hydrogen, and a substituted heteroaryl group means a functional group in which a substituted aromatic compound structure is connected with a structure containing at least one atom other than carbon and hydrogen. Such atoms other than carbon and hydrogen include, but are not limited to, nitrogen, sulfur, oxygen, silicon, and halogen elements.

[0070] The term 'diarylamino group' as used herein may refer to a functional group in which two aryl groups are bonded to a nitrogen atom. An unsubstituted diarylamino group means that both of the aryl groups are unsubstituted, and a substituted diarylamino group means that at least one of the two aryl groups is substituted.

[0071] The term 'diheteroarylamino group' used herein may refer to a functional group in which both aryl groups of the diarylamino group are changed to heteroaryl groups. An unsubstituted diheteroarylamino group means that both heteroaryl groups are unsubstituted, and a substituted diheteroarylamino group means that at least one of the two heteroaryl groups is substituted.

[0072] The term 'arylheteroarylamino group' used herein may refer to a functional group in which one of the aryl groups among the diarylamino groups is a heteroaryl group. An unsubstituted arylheteroarylamino group means that both the heteroaryl group and the aryl group are unsubstituted, and a substituted arylheteroarylamino group means that at least one of the aryl group and the heteroaryl group is substituted.

[0073] The above R6 and R7 may be separate, unconnected substituents, or may be adjacent to each other and connected to a ring.

[0074] The above R8 and R9 may be separate, unconnected substituents, or may be adjacent to each other and connected to a ring.

[0075] The term 'jointly connected to each other by a ring' as used herein means that two substituents are bonded to adjacent positions of a benzene ring, and the two adjacent substituents are bonded to each other to form a ring together with the benzene ring to which they are bonded.

[0076] The above R6 and R7 are adjacent to each other and are O, S, CR 13 R 14 , or NR 15 can be linked into a ring through .

[0077] The above R8 and R9 are adjacent to each other and are O, S, CR 16 R 17 , or NR 18 can be linked into a ring through .

[0078] The above R 13 Inland R 18 may each independently be hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted arylheteroarylamino group.

[0079] The above R 13 and R 14 may be separate, unconnected substituents, or may be adjacent to each other and connected to each other in a ring.

[0080] The above R 16 and R 17 may be separate, unconnected substituents, or may be adjacent to each other and connected to each other in a ring.

[0081] The term 'forming a ring by mutual bonding' used in this specification means that the carbon to which Y1 is bonded and the carbon to which Y2 is bonded are bonded to form a heterocyclic structure including a nitrogen atom.

[0082] Fluorescent materials only utilize singlet energy, resulting in a loss of 75% of the triplet energy. To address this, attempts have been made to develop organic light-emitting devices using phosphorescent materials that induce intersystem crossing (ISC) from singlets to triplets. However, conventional phosphorescent materials suffer from a problem in that their electroluminescence spectrum broadens due to the method of luminescence generated through charge transfer between heavy metals and organic compounds.

[0083] Unlike conventional fluorescence, which uses only the energy of the singlet and loses 75% of the energy of the triplet, delayed fluorescence can utilize the energy of both the triplet and the singlet by designing the molecule to have a small energy difference between the singlet and the triplet, and inducing the phenomenon of reverse inter-system crossing (RISC) from the triplet to the singlet using only thermal energy at room temperature. Therefore, unlike phosphorescent materials, triplets can be utilized without heavy metal substances, so the material efficiency is higher than that of fluorescent materials, and fluorescence emission can be realized via the triplet.

[0084] Conventional delayed fluorescent materials have a problem in that the donor unit and the acceptor unit are separated, and the connection between them is not fixed, so the electroluminescence spectrum is broadened due to molecular motion such as rotation and vibration.

[0085] On the other hand, the boron compound may include a multiple resonance structure in which the HOMO and LUMO are separated through a structure in which electron-deficient atoms and electron-rich atoms are alternately arranged. The multiple resonance structure has little overlap between the HOMO and LUMO, so that the reverse intersystem transition is easy with thermal energy at room temperature, and thus delayed fluorescence characteristics can be realized, and at the same time, a narrow half-width can be formed, so that excellent color purity can be realized.

[0086] For example, since a boron atom is relatively electron-poor, the carbon of the benzene ring directly connected to it may have an activated HOMO, and since a nitrogen atom is relatively electron-rich, the carbon of the benzene ring directly connected to it may have an activated LUMO. That is, the benzene ring connected to the boron atom may have a resonance structure in which HOMO-LUMO are repeated, and the benzene ring connected to the nitrogen atom may have a resonance structure in which LUMO-HOMO are repeated and are mutually arranged. The boron compound may form multiple resonance structures through the opposite resonance effect by alternating the mutually arranged resonance structures.

[0087] The above boron compound has a tightly fixed boron-nitrogen cycle structure, exhibiting a small Stokes shift characteristic, and thus can realize high color purity with a narrow half-width. In addition, the above boron compound can further improve luminescence efficiency by isolating only the HOMO-LUMO resonance form.

[0088] The above boron compound may include a structure derived from indolocarbazole or a structure in which benzofuran, benzothiophene, or benzofluorene is linked to carbazole. The above boron compound may include multiple resonance structures to maximize the multi-resonance effect, thereby breaking up the flat structure of 'CzBN' and increasing color purity.

[0089] The above boron compound may be a boron compound for an organic light-emitting device. When the light-emitting layer of the organic light-emitting device is formed with the above boron compound, a delayed fluorescent dopant or a phosphorescent dopant, and a host, the entire energy of the singlet can be transferred to the fluorescent dopant, thereby realizing higher efficiency than a conventional fluorescent dopant device and simultaneously high color purity characteristics of the fluorescent dopant. In this specification, this is referred to as a delayed fluorescent photosensitive or phosphorescent photosensitive superfluorescent device.

[0090] The above boron compound can control the luminescence color by including a substituent represented by chemical formula 2 in at least one of R1 to R3, and can increase the color purity by breaking the flat structure of 'CzBN' by giving a three-dimensional effect.

[0091] The above boron compound may be represented by any one of the following chemical formulas 1-1 to 1-68, but is not limited thereto.

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] The emission spectrum of the above boron compound may have a peak at 450 to 600 nm. For example, the peak may be at 450 nm, 460 nm, 470 nm, 480 nm, 490 nm, 500 nm, 510 nm, 520 nm, 530 nm, 540 nm, 550 nm, 560 nm, 570 nm, 580 nm, 590 nm, 600 nm, or a range between any two of these values. For example, the above boron compound may emit green light at about 490 to 570 nm.

[0106] The half-width of the above boron compound may be 40 nm or less. For example, it may be 40 nm, 35 nm, 30 nm, 25 nm, 20 nm, 15 nm, 10 nm, or a range between any two of these values. The smaller the half-width of the boron compound, the better the color purity can be realized.

[0107] The energy difference between the singlet and triplet of the above boron compound (ΔE st ) may be 0.20 eV or less. For example, it may be 0.20 eV, 0.15 eV, 0.10 eV, 0.05 eV, or a range between any two of these values. The smaller the energy difference, the easier the intersystem transition between singlet and triplet, and thus the material may be more useful as a delayed fluorescence material.

[0108] The photoluminescence quantum yield (PLQY) of the above boron compound may be 90% or greater. For example, it may be 90% or greater, 92.5% or greater, 95% or greater, or 97.5% or greater. The greater the photoluminescence quantum yield value, the more the efficiency of the organic light-emitting device may be improved.

[0109] These characteristic values ​​may be derived from the structural properties of the aforementioned boron compounds.

[0110] organic light-emitting diode

[0111] According to another aspect of the present disclosure, an organic light-emitting device comprises: a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers interposed between the first electrode and the second electrode; wherein one or more of the organic layers may include one or more of the aforementioned boron compounds.

[0112] The above organic light-emitting device can achieve a narrow half-width and high efficiency by having an organic layer including the aforementioned boron compound. In addition, if the boron compound exhibits delayed fluorescence characteristics, the device can be a delayed fluorescence organic light-emitting device.

[0113] In another example, the organic light-emitting device may include a host for various known green light-emitting layers and the boron compound.

[0114] The first electrode may be an anode, the second electrode may be a cathode, and the organic layer may include: a light-emitting layer including at least one of the aforementioned boron compounds; a hole transport region interposed between the first electrode and the light-emitting layer and including at least one of a hole injection layer, a hole transport layer, and an electron blocking layer; and an electron transport region interposed between the light-emitting layer and the second electrode and including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.

[0115] The above organic layer may include an emission layer including one or more host compounds; a delayed fluorescent compound or a phosphorescent compound; and the above-described boron compound. The characteristics of the organic light-emitting device may depend on the composition of the host and dopant materials of the emission layer, and when a delayed fluorescent dopant or a phosphorescent dopant is applied as a host, 100% of singlet energy can be transferred to the fluorescent dopant. Therefore, when the emission layer is composed of a host, a delayed fluorescent or phosphorescent host, and a fluorescent dopant, a delayed fluorescent or phosphorescent photosensitive superfluorescent device that has higher efficiency than a conventional fluorescent dopant device and simultaneously implements the high color purity characteristics of the fluorescent dopant can be manufactured.

[0116] Various known compounds can be used as the host compound, delayed fluorescent compound, and phosphorescent compound, and the characteristics of a device having such delayed fluorescent or phosphorescent properties can be significantly improved by including the aforementioned boron compound. For example, the delayed fluorescent compound or phosphorescent compound may be a dopant that implements sky blue or green, but is not limited thereto.

[0117] The content of the delayed fluorescent compound or phosphorescent compound may be 0.1 to 50 parts by weight, for example, 0.1 parts by weight, 5 parts by weight, 10 parts by weight, 15 parts by weight, 20 parts by weight, 25 parts by weight, 30 parts by weight, 35 parts by weight, 40 parts by weight, 45 parts by weight, 50 parts by weight, or a range between two of these values, based on 100 parts by weight of the host compound.

[0118] The content of the boron compound may be 0.1 to 90 parts by weight, for example, 0.1 parts by weight, 5 parts by weight, 10 parts by weight, 15 parts by weight, 20 parts by weight, 25 parts by weight, 30 parts by weight, 35 parts by weight, 40 parts by weight, 45 parts by weight, 50 parts by weight, 55 parts by weight, 60 parts by weight, 65 parts by weight, 70 parts by weight, 75 parts by weight, 80 parts by weight, 85 parts by weight, 90 parts by weight, or a range between any two of these values, based on 100 parts by weight of the delayed fluorescent compound or the phosphorescent compound. The properties thereof can be improved by adding a small amount of the boron compound compared to the delayed fluorescent compound or the phosphorescent compound.

[0119] A substrate may be additionally placed below the first electrode or above the second electrode. As the substrate, a substrate used in a general organic light-emitting device may be used, and a glass substrate or transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofing may be used, but is not limited thereto.

[0120] The first electrode may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The first electrode may be formed, for example, on an upper portion of a substrate, by a deposition method or a sputtering method, etc. of a material for the first electrode. The material for the first electrode may be selected from materials having a high work function to facilitate hole injection, and examples of such materials for the first electrode include, but are not limited to, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like.

[0121] The above hole injection layer can be formed on the first electrode using various methods such as vacuum deposition, spin coating, casting, and LB. When the hole injection layer is formed by vacuum deposition, the deposition conditions vary depending on the compound used as the hole injection layer material, the structure and thermal characteristics of the target hole injection layer, etc., but for example, the deposition temperature is about 100 to about 500°C, and the vacuum degree is about 10. -8 About 10 -3 torr, the deposition rate may be selected in the range of about 0.01 to about 100 Å / sec, but is not limited thereto.

[0122] When forming a hole injection layer by spin coating, the coating conditions vary depending on the compound used as the hole injection layer material, the structure of the desired hole injection layer, and the thermal characteristics, but the coating speed may be selected from about 2,000 rpm to about 5,000 rpm, and the heat treatment temperature for removing the solvent after coating may be selected from a temperature range of about 80°C to 200°C, but is not limited thereto.

[0123] The above conditions for forming the hole transport layer and electron blocking layer may refer to the conditions for forming the hole injection layer.

[0124] The thickness of each of the above layers may be from about 100 Å to about 10,000 Å, for example, from about 100 Å to about 1,000 Å. When the light-emitting layer includes a host and a dopant, the content of the dopant may typically be selected in a range of from about 0.01 to about 15 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

[0125] The maximum external quantum efficiency (EQE) of the above organic light-emitting device may be 15% or more. For example, it may be 15% or more, 15.5% or more, 16% or more, 16.5% or more, 17% or more, 17.5% or more, 18% or more, 18.5% or more, 19% or more, 19.5% or more, 20% or more, 20.5% or more, 21% or more, 21.5% or more, 22% or more, 22.5% or more, 23% or more, 23.5% or more, 24% or more, 24.5% or more, or 25% or more. Unlike conventional light-emitting devices having a maximum external quantum efficiency of about 10%, the above organic light-emitting device can realize excellent external quantum efficiency by including the above-described boron compound.

[0126] Hereinafter, the embodiments of this specification will be described in more detail. However, the experimental results below represent only representative experimental results among the above embodiments, and the scope and content of this specification cannot be interpreted as being reduced or limited by the embodiments, etc. The effects of each of the various implementation examples of this specification that are not explicitly presented below will be specifically described in the relevant sections.

[0127] Example 1: Compound 1-8

[0128] Manufacturing Example 1-1: Synthesis of Intermediate 1

[0129] 2-Bromo-1,3-difluoro-5-iodobenzene (4.50 g, 14.11 mmol), 5-phenyl-5,8-dihydroindolo[2,3-c]carbazole (9.40 g, 28.22 mmol), and cesium carbonate (14.00 g, 42.33 mmol) were mixed in 40 mL of anhydrous N,N-dimethylformamide and refluxed for 7 hours under an argon atmosphere to terminate the reaction. The reaction mixture was cooled to room temperature and poured into 1000 mL of water. The resulting white solid was washed with methanol (2 x 50 mL) and dried to obtain the desired intermediate 1 (10.89 g, yield 82%).

[0130] The synthesis process of the above intermediate 1 is briefly summarized in the reaction scheme 1 below.

[0131] [Reaction Formula 1]

[0132]

[0133] Manufacturing Example 1-2: Synthesis of Intermediate 2

[0134] To a toluene (50 mL) solution of intermediate 1 (2.50 g, 2.65 mmol), bis(4-(tert-butyl)phenyl)amine (0.82 g, 2.91 mmol), and sodium tert-butoxide (0.43 g, 4.50 mmol) was added tri(tert-butyl)phosphine (0.07 mL, 0.27 mmol). Palladium(II) acetate (0.03 g, 0.14 mmol), a catalyst, was added and refluxed for 3 h under an argon atmosphere. After the reaction was completed, the reaction mixture was cooled to room temperature, washed with water (300 mL), and extracted with dichloromethane (3 x 100 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, and the solvent was removed. The obtained solid was purified by column chromatography to obtain intermediate 2 (1.63 g, yield 56%).

[0135] The synthetic process of the above intermediate 2 is briefly summarized in reaction scheme 2 below.

[0136] [Reaction Formula 2]

[0137]

[0138] Manufacturing Example 1-3: Synthesis of Compound 1-8

[0139] Intermediate 2 (1.20 g, 1.09 mmol) was dissolved in tert-butylbenzene (30 mL) and degassed under argon for 30 minutes. n-Butyllithium hexane solution (0.88 mL, 2.50 M, 2 eq.) was added dropwise at -10 °C and reacted at 50 °C for 2.5 hours. After cooling the reaction solution to -40 °C, boron tribromide (0.21 mL, 2.19 mmol) was slowly added and reacted at room temperature for approximately 1 hour. N,N-diisopropylethylamine (DIPEA) (0.76 mL, 4.38 mmol) was added at 0°C, and the reaction mixture was allowed to warm to room temperature and then heated at 125°C for 14 h. After the reaction was complete, the mixture was cooled to room temperature and the solvent was removed. The obtained solid was dissolved in hot toluene and purified by passing it through silica / florisil. After removing the solvent, further purification was performed by column chromatography to obtain compound 1-8 (0.30 g, yield 27%).

[0140] The synthesis process of the above compounds 1-8 is briefly summarized in Scheme 3 below.

[0141] [Reaction Formula 3]

[0142]

[0143] Example 2: Compound 1-14

[0144] Manufacturing Example 2-1: Synthesis of Intermediate 3

[0145] The synthesis of intermediate 3 was carried out in the same manner as the synthesis of intermediate 2 of the above manufacturing example 1-2, but bis(4-biphenyl)amine (0.75 g, 2.33 mmol) was used instead of bis(4-(tert-butyl)phenyl)amine, and intermediate 3 (1.8 g, yield 75%) as a white solid was obtained.

[0146] The synthesis process of the above intermediate 3 is briefly summarized in reaction scheme 4 below.

[0147] [Reaction Formula 4]

[0148]

[0149] Manufacturing Example 2-2: Synthesis of Compound 1-14

[0150] The synthesis of compound 1-14 was carried out in the same manner as the synthesis of compound 1-8 in Preparation Example 1-3, but intermediate 3 (2.0 g, 1.76 mmol) was used instead of intermediate 2, and compound 1-14 (0.5 g, yield 27%) was obtained.

[0151] The synthetic process of the above compound 1-14 is briefly summarized in Scheme 5 below.

[0152] [Reaction Formula 5]

[0153]

[0154] Example 3: Compound 1-39

[0155] Manufacturing Example 3-1: Synthesis of Intermediate 4

[0156] To a toluene (60 mL) solution of intermediate 1 (3.00 g, 3.18 mmol), 3,6-di-tert-butyl-9H-carbazole (0.90 g, 3.18 mmol) and sodium tert-butoxide (0.45 g, 4.77 mmol) was added tri(tert-butyl)phosphine (0.09 mL, 0.32 mmol) and the catalyst tris(dibenzylideneacetone) dipalladium(0) (0.15 g, 0.16 mmol), and the mixture was refluxed under an argon atmosphere for 3 h. After the reaction was completed, the reaction mixture was cooled to room temperature, washed with water (500 mL), and extracted with dichloromethane (3 x 100 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, and the solvent was removed. The obtained solid was purified by column chromatography to obtain intermediate 4 (2.10 g, yield 60%).

[0157] The synthetic process of the above intermediate 4 is briefly summarized in reaction scheme 6 below.

[0158] [Reaction Formula 6]

[0159]

[0160] Manufacturing Example 3-2: Synthesis of Compound 1-39

[0161] The synthesis of compound 1-39 was carried out in the same manner as the synthesis of compound 1-8 in Preparation Example 1-3, but intermediate 4 (1.0 g, 0.91 mmol) was used instead of intermediate 2, and compound 1-39 (0.28 g, yield 28%) was obtained.

[0162] The synthetic process of the above compound 1-39 is briefly summarized in Scheme 7 below.

[0163] [Reaction Formula 7]

[0164]

[0165] Example 4: Compound 1-31

[0166] Manufacturing Example 4-1: Synthesis of Intermediate 5

[0167] 2-Bromo-1,3-difluoro-5-iodobenzene (5.0 g, 15.68 mmol), 5-phenyl-5,8-dihydroindolo[2,3-c]carbazole (5.2 g, 15.68 mmol), and cesium carbonate (7.7 g, 23.52 mmol) were mixed in 50 mL of anhydrous N,N-dimethylformamide and refluxed for 7 hours under an argon atmosphere to complete the reaction. The reaction mixture was cooled to room temperature and poured into 1000 mL of water. The resulting white solid was washed with methanol (2 x 50 mL) and dried to obtain 5-(2-bromo-3-fluoro-5-iodophenyl)-8-phenyl-5,8-dihydroindole[2,3-c]carbazole (6.14 g, yield 62%). The obtained white solid (5.0 g, 7.92 mmol), 11,11-diphenyl-5,11-dihydroindeno[1,2-b]carbazole (3.6 g, 8.71 mmol) and cesium carbonate (3.9 g, 11.88 mmol) were mixed in 50 mL of anhydrous N,N-dimethylformamide and refluxed under an argon atmosphere for 8 hours to complete the reaction. The reaction mixture was cooled to room temperature and poured into 1000 mL of water. The resulting white solid was washed with methanol (2 x 50 mL) and dried to obtain intermediate 5 (7.26 g, yield 90%).

[0168] The synthetic process of the above intermediate 5 is briefly summarized in reaction scheme 8 below.

[0169] [Reaction Formula 8]

[0170]

[0171] Manufacturing Example 4-2: Synthesis of Intermediate 6

[0172] To a toluene (50 mL) solution of intermediate 5 (3.0 g, 2.94 mmol), bis(4-(tert-butyl)phenyl)amine (0.95 g, 3.39 mmol), and sodium tert-butoxide (0.42 g, 4.42 mmol) was added tri(tert-butyl)phosphine (0.07 mL, 0.27 mmol). The catalyst palladium(II) acetate (0.03 g, 0.14 mmol) was added under an argon atmosphere, and the mixture was refluxed for 2.5 h. After the reaction was completed, the reaction mixture was cooled to room temperature, washed with water (300 mL), and extracted with dichloromethane (3 x 100 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, and the solvent was removed. The obtained solid was purified by column chromatography to obtain intermediate 6 (2.4 g, yield 70%).

[0173] The synthetic process of the above intermediate 6 is briefly summarized in reaction scheme 9 below.

[0174] [Reaction Formula 9]

[0175]

[0176] Manufacturing Example 4-3: Synthesis of Compound 1-31

[0177] The synthesis of compound 1-31 was carried out in the same manner as the synthesis of compound 1-8 in Preparation Example 1-3, but intermediate 6 (1.5 g, 1.28 mmol) was used instead of intermediate 2, and compound 1-31 (0.35 g, yield 25%) was obtained.

[0178] The synthetic process of the above compound 1-31 is briefly summarized in Scheme 10 below.

[0179] [Reaction Formula 10]

[0180]

[0181] Example 5: Compound 1-63

[0182] Manufacturing Example 5-1: Synthesis of Intermediate 7

[0183] The synthesis of intermediate 7 was carried out in the same manner as the synthesis of intermediate 4 in Manufacturing Example 3-1, but intermediate 5 (4.0 g, 3.93 mmol) was used instead of intermediate 1, and intermediate 7 (3.9 g, yield 85%) as a white solid was obtained.

[0184] The synthetic process of the above intermediate 7 is briefly summarized in reaction scheme 11 below.

[0185] [Reaction Formula 11]

[0186]

[0187] Manufacturing Example 5-2: Synthesis of Compound 1-63

[0188] The synthesis of compound 1-63 was carried out in the same manner as the synthesis of compound 1-39 in Preparation Example 3-2, but intermediate 7 (1.5 g, 1.28 mmol) was used instead of intermediate 4, and compound 1-63 (0.32 g, yield 23%) was obtained.

[0189] The synthetic process of the above compound 1-63 is briefly summarized in Scheme 12 below.

[0190] [Reaction Formula 12]

[0191]

[0192]

[0193] Experimental Example 1: Evaluation of physical properties of boron compounds

[0194] The physical properties of the compounds of Examples 1 to 5 and bis[2-(2-pyridinyl-N)phenyl-C](acetylacetonato)iridium(III) (Bis[2-(2-pyridinyl-N)phenyl-C](acetylacetonato)iridium(III); Ir(ppy)2acac) (Comparative Example 1) manufactured according to the above manufacturing examples were evaluated.

[0195] The measured properties were UV-Vis absorption spectra and photoluminescence (PL) spectra at room temperature (300 K) and low temperature (77 K). The UV-Vis absorption spectra were measured using JASCO V-750 in toluene solvent at 1x10 -5 It was measured by diluting to a concentration of M. In the case of the photoluminescence spectrum in a solution state, 1x10 -5 It was produced under the condition of concentration of M and measured using JASCO-FP 8500 equipment.

[0196] The measurement results for compound 1-8 of Example 1 are shown in FIGS. 1 and 3. FIG. 1 shows the UV-Vis absorption spectrum and the room temperature photoluminescence (RTPL) spectrum of compound 1-8 (BpIC-DPA), and FIG. 3 shows the room temperature photoluminescence (RTPL) spectrum and the low temperature photoluminescence (LTPL) spectrum of compound 1-8.

[0197] The measurement results for compound 1-39 of Example 3 are shown in Fig. 2. Fig. 2 shows the UV-Vis absorption spectrum and room temperature photoluminescence (RTPL) spectrum of compound 1-39 (BpIC-Cz).

[0198] Table 1 below shows the results of measuring the physical properties of the compounds of Examples 1 to 5 and the compound of Comparative Example 1.

[0199] Comparison Example 1 Example 1 Example 2 Example 3 Example 4 Example 5 Compound Ir(ppy)2acac Compound 1-8 Compound 1-14 Compound 1-39 Compound 1-31 Compound 1-63 Maximum absorption spectrum 491 nm 512 nm 513 nm 516 nm 511 nm 511 nm Maximum emission spectrum 520 nm 527 nm 529 nm 534 nm 525 nm 528 nm Full width at half maximum 64 nm 25 nm 26 nm 22 nm 27 nm 24 nm ΔEst -0.17 eV0.15 eV0.18 eV0.18 eV0.20 eV

[0200] Referring to Table 1 above, the compounds of Examples 1 to 5 exhibited green emission with a half-width much narrower than that of the phosphor of Comparative Example 1. In addition, the compounds of Examples 1 to 5 exhibited a ... of ΔE between the singlet and the triplet. st ) was also small at 0.20 eV or less, so it was confirmed that the reverse intersystem transition at room temperature could easily occur, and in the case of compound 1-8 of Example 1, the photoluminescence quantum yield (PLQY) was measured to be very high at 91.1%.

[0201] Experimental Example 2: Evaluation of a delayed fluorescent device containing a boron compound

[0202] An ITO glass substrate was cut into a size of 50 mm x 50 mm x 0.7 mm, washed with acetone, isopropyl alcohol, and distilled water for 10 minutes each, then exposed to ultraviolet light for 10 minutes and ozone for cleaning, and then the ITO glass substrate was mounted on a vacuum deposition device.

[0203] An organic light-emitting device was manufactured by sequentially stacking HATCN (9 nm) / PCBBiF (72 nm) / PCzAc (12 nm) / DIC-Trz host and 2% boron compound (Compound 1-8 or Compound 1-39) (30 nm) / DDBFT (10 nm) / BPPB (47 nm) / LiF (1.5 nm) / Al (90 nm) on the ITO glass substrate. The structure of the organic material used is as follows.

[0204]

[0205] The device measurement results are shown in Fig. 4 and Table 2 below. Fig. 4 shows the electroluminescence spectra of delayed fluorescent devices containing compound 1-8 (BpIC-DPA) or compound 1-39 (BpIC-Cz).

[0206] Classification Example 6 Example 7 Boron compounds Compounds 1-8 (Example 1) Compounds 1-39 (Example 3) Maximum EQE 16.8 % 17.5 % Maximum electroluminescence wavelength 536 nm 542 nm Full width at half maximum 27 nm 32 nm

[0207] Referring to Table 2 and FIG. 4, in the case of compound 1-8 (BpIC-DPA, Example 1) substituted with bis(4-(tert-butyl)phenyl)amine, it can be confirmed that the half-width of the electroluminescence wavelength is broadened by 2 nm compared to the half-width of the solution emission measured in Experimental Example 1. In the case of compound 1-39 (BpIC-Cz, Example 3) substituted with 3,6-di-tert-butyl-9H-carbazole, it can be confirmed that the half-width of the electroluminescence wavelength is broadened by 10 nm compared to the half-width of the solution emission measured in Experimental Example 1. These results may mean that a phenyl amine substituted with a tert-butyl group at the para position is bulkier and less prone to agglomeration than a carbazole substituted with a tert-butyl group.

[0208] Experimental Example 3: Evaluation of a phosphorescent photosensitive superfluorescent device containing a boron compound.

[0209] An ITO glass substrate was cut into a size of 50 mm x 50 mm x 0.7 mm, washed with acetone, isopropyl alcohol, and distilled water for 10 minutes each, then exposed to ultraviolet light for 10 minutes and ozone for cleaning, and then the ITO glass substrate was mounted on a vacuum deposition device.

[0210] An organic light-emitting device was manufactured by stacking HATCN (9 nm) / PCBBiF (72 nm) / PCzAc (12 nm) / DIC-Trz host, 5% of Ir(ppy)2acac and X% of boron compound (compound 1-8 or compound 1-39) (30 nm) / DDBFT (10 nm) / BPPB (47 nm) / LiF (1.5 nm) / Al (90 nm) in that order on the ITO glass substrate.

[0211] The device measurement results are shown in Fig. 5 and Table 3 below. Fig. 5 shows the electroluminescence spectra of a phosphorescent organic light-emitting device (PHOLED) that does not contain a boron compound and a phosphorescent photosensitive superfluorescent device containing compound 1-8 (BpIC-DPA) or compound 1-39 (BpIC-Cz).

[0212] Comparison Example 2 Example 8 Example 9 Boron compounds - Compounds 1-8 (Example 1) Compounds 1-39 (Example 3) Doping concentration (X) 0 % 2 % 4 % Maximum EQE 25.3 % 22.0 % 25.7 % Maximum electroluminescence wavelength 526 nm 536 nm 544 nm Full width at half maximum 69 nm 29 nm 32 nm CIE (x,y) (0.34, 0.62) (0.30, 0.67) (0.34, 0.64) Device lifetime (LT90) @ 1,000 nit - 156.1 h 29 1.5 h

[0213] Referring to Table 3 and Figure 5 above, it was confirmed that the half-width of the phosphorescent photosensitive superfluorescent devices of Examples 8 and 9 was significantly narrower than that of Comparative Example 2, which was a phosphorescent device. This is because the half-width of the boron compound itself, which is the final luminescent device, is narrow.

[0214] The reason why the maximum EQE of Example 9 is higher than that of Example 8 is because the overlap between the emission spectrum of the phosphorescent material Ir(ppy)2acac and the absorption spectrum of Compound 1-39 is greater than that with the absorption spectrum of Compound 1-8. It was also confirmed that the lifetime of the device of Example 9 was better.

[0215] The description of this specification above is for illustrative purposes only, and those skilled in the art will readily appreciate that aspects of this specification can be readily modified into other specific forms without altering the technical concepts or essential features described herein. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive. For example, each component described as a single entity may be implemented in a distributed manner, and similarly, components described as distributed may be implemented in a combined manner.

[0216] The scope of this specification is indicated by the claims set forth below, and all changes or modifications derived from the meaning and scope of the claims and their equivalent concepts should be interpreted as being included within the scope of this specification.

Claims

1. A boron compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, R1 to R 10 are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted arylheteroarylamino group, R6 and R7 can be connected to each other as a ring, R8 and R9 can be connected to each other as a ring, At least one of R1 to R3 is represented by the following chemical formula 2, [Chemical formula 2] In the above chemical formula 2, R 11 and R 12 are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted arylheteroarylamino group, R 11 and R 12 At least one of them is not hydrogen or deuterium, n1 and n2 are each independently an integer from 1 to 4, Y1 and Y2 are each independently hydrogen, deuterium, or an alkyl group, or are combined with each other to form a ring.

2. In paragraph 1, A boron compound represented by any one of the following chemical formulas 1-1 to 1-68: .

3. In paragraph 1, A boron compound having an emission spectrum having a peak at 450 to 600 nm.

4. In paragraph 1, A boron compound having a half-width of 40 nm or less.

5. In paragraph 1, A boron compound, wherein the energy difference between the singlet and the triplet of the boron compound is 0.20 eV or less.

6. In paragraph 1, A boron compound having a photoluminescence quantum yield (PLQY) of 90% or more.

7. First electrode; A second electrode provided opposite to the first electrode; and comprising at least one organic layer interposed between the first electrode and the second electrode; An organic light-emitting device, wherein at least one of the organic layers contains at least one boron compound of claim 1.

8. In paragraph 7, The above first electrode is an anode, the above second electrode is a cathode, The above organic layer is, A light-emitting layer comprising at least one boron compound of claim 1; A hole transport region interposed between the first electrode and the light-emitting layer and including at least one of a hole injection layer, a hole transport layer, and an electron blocking layer; and An organic light-emitting device comprising an electron transport region interposed between the light-emitting layer and the second electrode and including at least one of a hole-blocking layer, an electron transport layer, and an electron injection layer.

9. In paragraph 7, The above organic layer is, An organic light-emitting device comprising an emitting layer comprising one or more host compounds; a delayed fluorescent compound or a phosphorescent compound; and a boron compound of claim 1.

10. In paragraph 7, An organic light-emitting device having a maximum external quantum efficiency (EQE) of 15% or more.

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