Compound and organic light-emitting element comprising same

Abstract

The present specification relates to a compound of Chemical Formula 1 and an organic light-emitting device comprising the same. The compound may improve efficiency, low operating voltage, and / or lifespan characteristics of an organic light emitting device. In particular, the compounds described in the present disclosure may be used as materials for light emitting layers. Further, it provides effects of reducing an operating voltage, improving high efficiency, and / or improving a long lifetime compared to an existing organic light-emitting device.

Description

TECHNICAL FIELD

[0001] This application claims the benefit of Korean Patent Application No. 10-2024-0073523, filed June 5, 2024, and Korean Patent Application No. 10-2025-0071926, filed June 2, 2025, in the Korean Intellectual Property Office, the disclosures of which are incorporated herein in their entireties by reference.

[0002] The present specification relates to a compound and an organic light emitting device comprising the same. BACKGROUND

[0003] In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy by using organic material. An organic light emitting device utilizing the organic light emitting phenomenon typically has a structure including an anode, a cathode, and an organic layer between them. Here, the organic layer typically has a multi-layer structure composed of different materials in order to improve efficiency and stability of the organic light emitting device. For example, the organic layer can be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of the organic light emitting device, when a voltage is applied between two electrodes, a hole is injected into the organic layer from the anode and an electron is injected into the organic layer from the cathode. An exciton is formed when the injected hole and electron recombine, and light is emitted when the exciton returns to the ground state.

[0004] There is a need to develop new materials for an organic light emitting device. SUMMARY

[0005] TECHNICAL PROBLEM

[0006] The present specification provides a compound and an organic light emitting device comprising the same.

[0007] TECHNICAL SOLUTION

[0008] One exemplary embodiment of the present specification provides a compound of Chemical Formula 1.

[0009] [Chemical Formula 1]

[0010]

[0011] In Chemical Formula 1,

[0012] R1 to R6 are the same or different, and are independently hydrogen; deuterium; or a substituted or unsubstituted aryl group,

[0013] D is deuterium,

[0014] r1 and r3 to r6 are each an integer of 1 to 4,

[0015] r2 is an integer of 1 to 3,

[0016] If each of r1 to r6 is 2 or greater, then two or more of r1 to r6 are either the same or different.

[0017] x1 is an integer from 0 to 2, and

[0018] x2 and x3 are each integers from 0 to 5.

[0019] Furthermore, an exemplary embodiment of this specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the aforementioned compound.

[0020] Beneficial effects

[0021] The compounds described in this specification can be used as materials for organic layers in organic light-emitting devices (OLEDs). Compounds according to at least one exemplary embodiment of this specification can improve the efficiency of OLEDs, reduce the operating voltage of OLEDs, and / or improve the lifetime characteristics of OLEDs. In particular, the compounds described in this disclosure can be used as materials for light-emitting layers. Furthermore, compared to existing OLEDs, they offer the effects of lower operating voltage, improved efficiency, and / or improved lifetime. Attached Figure Description

[0022] Figure 1 and Figure 2 Examples of organic light-emitting devices in exemplary embodiments of this specification are shown.

[0023] Figure 3 The MS spectrum of compound A is shown.

[0024] [Explanation of reference numerals in the attached figures]

[0025] 1: Base

[0026] 2: First electrode

[0027] 3: Second electrode

[0028] 4: Organic layer

[0029] 5: Hole injection layer

[0030] 6: Hole transport layer

[0031] 7: Electron blocking layer

[0032] 8: Emissive layer

[0033] 9: Hole-blocking layer

[0034] 10: Electron Injection and Transport Layer Detailed Implementation

[0035] This instruction manual will be described in more detail below.

[0036] This specification provides information on compounds of chemical formula 1.

[0037] According to an exemplary embodiment of this specification, Formula 1 can prevent host-guest electrostatic interactions in the organic layer of an organic light-emitting device containing the compound due to the increase in the LUMO energy level of the compound caused by the presence of the bicarbazole structure. Furthermore, the divalent triphenyl group connecting bicarbazole and carbazole has structural features that stabilize the excited state and polaron state of Formula 1 by participating in the conjugated system via a hyperconjugation effect. Therefore, Formula 1 can be included in the organic layer of an organic light-emitting device to improve efficiency, reduce operating voltage, and improve lifetime characteristics.

[0038] Formula 1 has a structure in which carbazole and bicarbazole are bonded to a 2-position benzene of a centrally located terphenyl group. It exhibits high triplet state energy, and organic light-emitting devices containing it possess low voltage, high efficiency, and long lifetime characteristics because hole injection and energy transfer to the dopant are efficient.

[0039] Furthermore, because the physicochemical properties of deuterium (e.g., bond lengths) differ from those of hydrogen, and the stretching of the CD bond is less than that of the CH bond, the van der Waals radius of deuterium is smaller than that of hydrogen, and the CD bond is generally shorter and stronger than the CH bond. Therefore, when formula 1 contains deuterium, the ground state energy decreases, and as the bond length between deuterium and carbon shortens, the volume of the molecular hard core decreases, potentially leading to a decrease in polarizability. Additionally, the film volume can be increased by weakening intermolecular interactions. Moreover, these properties can reduce the crystallinity of the film (i.e., produce an amorphous state), and can generally effectively improve the lifetime and operating characteristics of organic light-emitting devices. Furthermore, heat resistance can be improved compared to conventional organic light-emitting devices.

[0040] Examples of substituents described below are presented, but are not limited thereto.

[0041] In this instruction manual, It refers to the connecting part.

[0042] The term "substitution" refers to replacing a hydrogen atom bonded to a carbon atom in a compound with another substituent. There are no restrictions on the position of the substitution, as long as it is a position where a hydrogen atom can be substituted. When two or more substitutions are present, the two or more substituents can be the same or different.

[0043] In this specification, the term "substituted or unsubstituted" means substituted with one or more of the following substituents: deuterium; halogen group; cyano; alkyl; cycloalkyl; alkoxy; alkenyl; haloalkyl; silyl; aryl; fused ring group of aromatic and aliphatic hydrocarbon rings; and heterocyclic group, substituted with a substituent connected to two or more of the above substituents, or having no substituents at all.

[0044] In this specification, the description of two or more substituents being linked means that the hydrogen of one substituent is linked to another substituent. For example, phenyl and naphthyl groups can be linked to form... or Furthermore, the connection of the three substituents not only includes the sequential connection of (substituent 1)-(substituent 2)-(substituent 3), but also includes (substituent 2) and (substituent 3) connected to (substituent 1). For example, phenyl, naphthyl, and isopropyl groups can be connected to form... , or The above limitations also apply to cases where four or more substituents are connected.

[0045] In this specification, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0046] In this specification, alkyl groups may be linear or branched, and the number of carbon atoms may be specifically from 1 to 30, but is not particularly limited thereto. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0047] In this specification, cycloalkyl groups can be C10, C20, C30, C40, C50, C60, C7 ...60, C60, C60, C60, C60, C 3-30 Cycloalkyl, but not limited thereto. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, etc., but not limited thereto.

[0048] In this specification, the alkoxy group can be linear, branched, or cyclic. The alkoxy group can be C10, C20, C30, C40, C50, C60, C7 ... 1-30 Alkoxy groups, but not specifically limited to them. Specifically, they can be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc., but not limited to them.

[0049] In this disclosure, the alkenyl group can be linear or branched, and the number of carbon atoms can specifically be from 2 to 30, but is not particularly limited thereto. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, It includes, but is not limited to, styrene, etc.

[0050] In this specification, haloalkyl means an alkyl group in which the hydrogen of the alkyl group is replaced by at least one halogen group.

[0051] In this specification, the number of carbon atoms in the aryl group may be specifically 6 to 30, but is not particularly limited thereto, and the aryl group may be monocyclic or polycyclic.

[0052] In this specification, the number of carbon atoms in a monocyclic aryl group can be specifically 6 to 30, but is not particularly limited thereto. Specifically, the monocyclic aryl group can be phenyl, biphenyl, terphenyl, etc., but is not limited thereto.

[0053] When the aryl group is a polycyclic aryl group, the number of carbon atoms can specifically be from 10 to 30, but is not particularly limited thereto. Specifically, the polycyclic aryl group can be naphthyl, anthraceneyl, phenanthrene, phenylene, pyrene, phenatenyl, etc. base, It includes, but is not limited to, methyl, fluorene, etc.

[0054] In this specification, the fluorene group may be substituted, and adjacent substituents may bond to each other to form a ring.

[0055] Examples of fluorene include , , , , , , and And so on, but not limited to these.

[0056] In this specification, "adjacent" groups may mean a substituent that is directly connected to the atom substituted by the substituent, a substituent that is stereochemically closest to the substituent, or another substituent that is substituted by the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon atom in an aliphatic ring can be interpreted as "adjacent" groups.

[0057] In this specification, a heteroaryl group comprises one or more heteroatoms, which are atoms other than carbon. Specifically, the heteroatoms include one or more atoms selected from O, N, Se, S, etc. In this specification, the number of carbon atoms in the heteroaryl group is specifically from 2 to 30, but is not particularly limited thereto, and the heteroaryl group can be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene, furanyl, pyrrole, imidazolyl, thiazolyl, etc. azole group, Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazenopyrazinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthridine, phenanthrolinyl, iso Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothiopyrrolyl, phen Thiol, phen Azinyl, phenothiazinyl, dihydroindocarbazolyl, spirofluorene Examples include, but are not limited to, ton-based, spirofluorene-thion-based, etc.

[0058] In this specification, silane can be alkylsilane, arylsilane, heteroarylsilane, etc. Among alkylsilanes, the alkyl group can be those exemplified above. Among arylsilanes, the aryl group can be those exemplified above. Furthermore, among heteroarylsilanes, the heteroaryl group can be those exemplified above.

[0059] In this specification, the cycloalkyl group can be an aromatic cycloalkyl group; an aliphatic cycloalkyl group; or a fused cycloalkyl group of an aromatic cycloalkyl group and an aliphatic cycloalkyl group. The foregoing description of aryl groups can be applied to aromatic cycloalkyl groups, and the foregoing description of cycloalkyl groups can be applied to aliphatic cycloalkyl groups. Furthermore, fused cycloalkyl groups of aromatic cycloalkyl groups can have a structure in which the aforementioned aryl and cycloalkyl groups are fused together.

[0060] In this specification, arylene refers to a divalent aryl group having two bonding positions. The foregoing description of aryl groups can be applied, except that arylene is divalent.

[0061] In this specification, "heteroaryl" means a heteroaryl group having two bonding sites, i.e., a divalent group. The foregoing description of heteroaryl groups applies, except that the heteroaryl group is divalent.

[0062] Unless otherwise specified in this specification, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. While similar or equivalent methods and materials to those described herein may be used in practice or in testing of exemplary embodiments of this disclosure, suitable methods and materials will be described below. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of conflict, this specification (including definitions) shall have priority unless a specific paragraph is cited. Furthermore, the materials, methods, and examples described above are illustrative only and are not intended to be limiting.

[0063] The compound of chemical formula 1 will be described in detail below.

[0064] In one exemplary embodiment of this specification, chemical formula 1 is any one of chemical formulas 2 to 4.

[0065] [Chemical Formula 2]

[0066]

[0067] [Chemical Formula 3]

[0068]

[0069] [Chemical Formula 4]

[0070]

[0071] In chemical formulas 2 to 4,

[0072] D, R1 to R6, r1 to r6 and x1 to x3 are the same as those defined in Chemical Formula 1.

[0073] In one exemplary embodiment of this specification, chemical formula 1 is any one of chemical formulas 2-1 to 2-5.

[0074] [Chemical Formula 2-1]

[0075]

[0076] [Chemical Formula 2-2]

[0077]

[0078] [Chemical Formula 2-3]

[0079]

[0080] [Chemical Formula 2-4]

[0081]

[0082] [Chemical Formula 2-5]

[0083]

[0084] In chemical formulas 2-1 to 2-5,

[0085] D, R1 to R6, r1 to r6 and x1 to x3 are the same as those defined in Chemical Formula 1.

[0086] In one exemplary embodiment of this specification, chemical formula 1 is any one of chemical formulas 3-1 to 3-6.

[0087] [Chemical Formula 3-1]

[0088]

[0089] [Chemical Formula 3-2]

[0090]

[0091] [Chemical Formula 3-3]

[0092]

[0093] [Chemical Formula 3-4]

[0094]

[0095] [Chemical Formula 3-5]

[0096]

[0097] [Chemical Formula 3-6]

[0098]

[0099] In chemical formulas 3-1 to 3-6,

[0100] D, R1 to R6, r1 to r6 and x1 to x3 are the same as those defined in Chemical Formula 1.

[0101] In one exemplary embodiment of this specification, chemical formula 1 is any one of chemical formulas 4-1 to 4-5.

[0102] [Chemical Formula 4-1]

[0103]

[0104] [Chemical Formula 4-2]

[0105]

[0106] [Chemical Formula 4-3]

[0107]

[0108] [Chemical Formula 4-4]

[0109]

[0110] [Chemical Formula 4-5]

[0111]

[0112] In chemical formulas 4-1 to 4-5,

[0113] D, R1 to R6, r1 to r6 and x1 to x3 are the same as those defined in Chemical Formula 1.

[0114] In one exemplary embodiment of this specification, It is one of the following structures.

[0115]

[0116] In the above structure,

[0117] R1 to R4 and r1 to r4 are the same as those defined in Chemical Formula 1, and * indicates those in Chemical Formula 1 that are identical to those defined in (D). x1 The substituted benzene ring bonded portion.

[0118] In one exemplary embodiment of this specification, R1 to R6 may be the same or different, and are independently hydrogen or deuterium.

[0119] In one exemplary embodiment of this specification, R1 to R6 are hydrogen.

[0120] In one exemplary embodiment of this specification, R1 to R6 are deuterium.

[0121] In one exemplary embodiment of this specification, R1 is hydrogen; or deuterium.

[0122] In one exemplary embodiment of this specification, R1 is hydrogen.

[0123] In one exemplary embodiment of this specification, R1 is deuterium.

[0124] In one exemplary embodiment of this specification, R2 is hydrogen; or deuterium.

[0125] In one exemplary embodiment of this specification, R2 is hydrogen.

[0126] In one exemplary embodiment of this specification, R2 is deuterium.

[0127] In one exemplary embodiment of this specification, R3 is hydrogen; or deuterium.

[0128] In one exemplary embodiment of this specification, R3 is hydrogen.

[0129] In one exemplary embodiment of this specification, R3 is deuterium.

[0130] In one exemplary embodiment of this specification, R4 is hydrogen; or deuterium.

[0131] In one exemplary embodiment of this specification, R4 is hydrogen.

[0132] In one exemplary embodiment of this specification, R4 is deuterium.

[0133] In one exemplary embodiment of this specification, R5 is hydrogen; or deuterium.

[0134] In one exemplary embodiment of this specification, R5 is hydrogen.

[0135] In one exemplary embodiment of this specification, R5 is deuterium.

[0136] In one exemplary embodiment of this specification, R6 is hydrogen; or deuterium.

[0137] In one exemplary embodiment of this specification, R6 is hydrogen.

[0138] In one exemplary embodiment of this specification, R6 is deuterium.

[0139] In one exemplary embodiment of this specification, if each of x1, x2, and x3 is 0, it means hydrogen, i.e., the benzene ring is unsubstituted.

[0140] In one exemplary embodiment of this specification, x1 is 0.

[0141] In one exemplary embodiment of this specification, x1 is 1.

[0142] In one exemplary embodiment of this specification, x1 is 2.

[0143] In one exemplary embodiment of this specification, x2 is 0.

[0144] In one exemplary embodiment of this specification, x2 is 1.

[0145] In one exemplary embodiment of this specification, x2 is 2.

[0146] In one exemplary embodiment of this specification, x2 is 3.

[0147] In one exemplary embodiment of this specification, x2 is 4.

[0148] In one exemplary embodiment of this specification, x2 is 5.

[0149] In one exemplary embodiment of this specification, x2 is 0.

[0150] In one exemplary embodiment of this specification, x3 is 1.

[0151] In one exemplary embodiment of this specification, x3 is 2.

[0152] In one exemplary embodiment of this specification, x3 is 3.

[0153] In one exemplary embodiment of this specification, x3 is 4.

[0154] In one exemplary embodiment of this specification, x3 is 5.

[0155] In one exemplary embodiment of this specification, the deuterium substitution rate of Formula 1 is 0% or higher.

[0156] In one exemplary embodiment of this specification, the deuterium substitution rate of Formula 1 is 2% or higher.

[0157] In one exemplary embodiment of this specification, the deuterium substitution rate of Formula 1 is 10% or higher.

[0158] In one exemplary embodiment of this specification, the deuterium substitution rate of Formula 1 is 15% or higher.

[0159] In one exemplary embodiment of this specification, the deuterium substitution rate of Formula 1 is 0% to 100%.

[0160] In one exemplary embodiment of this specification, the deuterium substitution rate of Formula 1 is from 2% to 100%.

[0161] In one exemplary embodiment of this specification, the deuterium substitution rate of Formula 1 is 10% to 100%.

[0162] In one exemplary embodiment of this specification, the deuterium substitution rate of Formula 1 is 15% to 100%.

[0163] In one exemplary embodiment of this specification, the deuterium substitution rate of Formula 1 is 80% to 100%.

[0164] In this specification, "containing deuterium", "deuterated" or "deuterated" means that hydrogen at a substituted position in the compound is replaced by deuterium.

[0165] In this specification, "fully deuterated" means a compound or group in which all hydrogen atoms in the molecule are replaced by deuterium, and has the same meaning as "100% deuterated".

[0166] In this specification, "X% deuterated", "degree of deuteration X%", or "deuteration rate X%" means that X% of the hydrogens at the substituted positions in the structure are replaced by deuterium. For example, when the corresponding structure is dibenzofuran, "25% deuterated", "degree of deuteration" or "deuteration rate" means that two of the eight hydrogens at the substituted positions in dibenzofuran are replaced by deuterium.

[0167] In this specification, "degree of deuteration" or "deuteration substitution rate" can be determined by known methods such as nuclear magnetic resonance spectroscopy (NMR spectroscopy). 1 It can be determined by methods such as ¹H NMR, thin-layer chromatography / mass spectrometry (TLC / MS), and gas chromatography / mass spectrometry (GC / MS).

[0168] Specifically, when measured by nuclear magnetic resonance spectroscopy (NMR spectroscopy) 1 When analyzing "degree of deuteration" or "rate of deuteration" using ¹H NMR, the degree of deuteration or rate of deuteration can be determined by adding dimethylformamide (DMF) as an internal standard. 1 The integration ratio on H NMR is calculated based on the integral of the total peak.

[0169] Furthermore, when analyzing "degree of deuteration" or "deuteration substitution rate" by TLC / MS (thin-layer chromatography / mass spectrometry), the substitution rate can be calculated based on the maximum value (median value) of the molecular weight distribution at the reaction endpoint. For example, when analyzing the degree of deuteration of compound A, if the molecular weight of the starting material is 506, and Figure 3 The maximum molecular weight (median value) of compound A in the MS spectrum is 527. Therefore, 21 of the 26 hydrogens at the substituted positions of the starting material are replaced by deuterium, and thus it can be calculated that about 81% of the hydrogens are deuterated.

[0170]

[0171] In this specification, D refers to deuterium.

[0172] In one exemplary embodiment of this specification, chemical formula 1 is any of the following compounds.

[0173]

[0174]

[0175] In the above compounds, D=28~35 means that 28 to 35 deuterium atoms can be substituted in the compound.

[0176] This specification also provides organic light-emitting devices containing the above-mentioned compounds.

[0177] In this specification, when a component is referred to as being "on" another component, this includes not only the case where the component is in contact with the other component, but also the case where there is another component between the two components.

[0178] In this specification, when a part is referred to as "including" a component, it means, unless otherwise stated, that it may also include other components.

[0179] In this specification, the term "layer" is used interchangeably with the term "film" primarily used in related art and refers to a coating covering a desired area. There is no limitation on the size of a "layer," and the dimensions of individual "layers" may be the same or different. In one exemplary embodiment, the size of a "layer" may be the same as the size of the entire device, may correspond to the size of a specific functional region, or may be as small as a single subpixel.

[0180] In this specification, the meaning of a specific material A being contained in layer B includes both of the following: i) one or more materials A are contained in a layer B; and ii) layer B consists of one or more layers, and materials A are contained in one or more of a plurality of layers B.

[0181] In this specification, the description that a particular material A is contained in layer C or layer D means i) that material A is contained in at least one of one or more layers C, ii) that material A is contained in at least one of one or more layers D, or iii) that material A is contained in one or more layers C and one or more layers D.

[0182] In this specification, n-type refers to a material that can acquire electrons from the matrix material (the material of the organic layer), and any generally known material can be used, but is not limited to this. In other words, n-type can be defined as a material that has the property of being able to provide electrons to the LUMO (lowest unoccupied molecular orbital) energy level of the matrix. Conversely, p-type refers to a material that, when a monolayer is formed solely from p-type material, receives electrons from the HOMO (highest occupied molecular orbital) energy level of the material in the adjacent cathode direction, thereby creating holes in the material in the adjacent cathode direction. Alternatively, when a p-type material is doped into any matrix, it receives electrons from the HOMO of the matrix material, thereby creating holes in the HOMO of the matrix. For this purpose, when a monolayer is formed solely from p-type material, the closer the HOMO energy level of the material in the cathode direction is to the LUMO of the p-type material, the easier it is for it to acquire electrons from the HOMO of the adjacent layer and create holes in the HOMO of the adjacent layer. Furthermore, when p-type materials are doped into any matrix, the closer the LUMO of the p-type material is to the HOMO of the matrix, the easier it is to acquire electrons and generate holes in the matrix.

[0183] This specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound of formula 1.

[0184] The organic layers of the organic light-emitting device described in this specification can be formed as a single-layer structure, or as a multilayer structure in which two or more organic layers are stacked. For example, it can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited to this, and it can include a smaller number of organic layers.

[0185] In one exemplary embodiment of this specification, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, hole transport layer, or hole injection and transport layer contains the aforementioned compound.

[0186] In one exemplary embodiment of this specification, the organic layer includes an electron blocking layer, and the electron blocking layer contains the aforementioned compound.

[0187] In one exemplary embodiment of this specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer.

[0188] In one exemplary embodiment of this specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the aforementioned compound.

[0189] In one exemplary embodiment of this specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the aforementioned compound as the body of the light-emitting layer.

[0190] In one exemplary embodiment of this specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the aforementioned compound as the p-type host of the light-emitting layer.

[0191] In one exemplary embodiment of this specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the aforementioned compound as a p-type phosphorescent host for the light-emitting layer.

[0192] In one exemplary embodiment of this specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the aforementioned compound as a host, and also contains other hosts.

[0193] In one exemplary embodiment of this specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the aforementioned compound as a host, and also contains a host and a dopant.

[0194] In one exemplary embodiment of this specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the aforementioned compound as a first body, and also contains a second body.

[0195] In one exemplary embodiment of this specification, the first subject is a p-type subject, and the second subject is an n-type subject.

[0196] In one exemplary embodiment of this specification, the first body is a p-type phosphorescent body, and the second body is an n-type phosphorescent body.

[0197] In one exemplary embodiment of this specification, the light-emitting layer comprises a first body and a second body in a weight ratio of 2:8 to 8:2, and the first body is a compound of formula 1.

[0198] In one exemplary embodiment of this specification, the light-emitting layer comprises a first body and a second body in a 1:1 weight ratio, and the first body is a compound of chemical formula 1.

[0199] In one exemplary embodiment of this specification, the second body is a dibenzofuran-based compound.

[0200] In one exemplary embodiment of this specification, the second body is chemically formulated as HB-1.

[0201] In one exemplary embodiment of this specification, the second body is a dibenzofuran-based compound substituted with a carbazoyl triazine group.

[0202] In one exemplary embodiment of this specification, the light-emitting layer further comprises a dopant.

[0203] In one exemplary embodiment of this specification, the light-emitting layer includes a first body and a second body, and also includes a dopant.

[0204] In one exemplary embodiment of this specification, the dopant is a phosphorescent dopant.

[0205] In one exemplary embodiment of this specification, the light-emitting layer comprises a dopant, and the dopant includes a phosphorescent dopant.

[0206] In one exemplary embodiment of this specification, the organic layer includes a light-emitting layer comprising a host and a dopant, the host comprising the aforementioned compound, and the dopant comprising the aforementioned phosphorescent dopant.

[0207] In one exemplary embodiment of this specification, the light-emitting layer is a blue light-emitting layer.

[0208] In one exemplary embodiment of this specification, the maximum emission wavelength of the light-emitting layer is 420 nm to 495 nm.

[0209] In one exemplary embodiment of this specification, the light-emitting layer comprises a host and a dopant in a weight ratio of 99:1 to 1:99. Specifically, it comprises a host and a dopant in a weight ratio of 10:90 to 90:10, 20:80 to 80:20, or 30:70 to 30:70.

[0210] When the emitting layer emits red light, phosphorescent materials such as PIQIr(acac) (bis(1-phenylisoquinoline)acetylacetone iridium), PQIr(acac) (bis(1-phenylquinoline)acetylacetone iridium), PQIr (tris(1-phenylquinoline)iridium), and PtOEP (octaethylporphyrin platinum) or fluorescent materials such as Alq3 (tris(8-hydroxyquinoline)aluminum) can be used as luminescent dopants, but are not limited thereto. When the emitting layer emits green light, phosphorescent materials such as Ir(ppy)3 (tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3 (tris(8-hydroxyquinoline)aluminum) can be used as luminescent dopants, but are not limited thereto. When the luminescent layer emits blue light, platinum complex compounds, phosphorescent materials such as (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, stilbene (DSB) or stilbene arylene (DSA), PFO-based polymers, PPV-based polymers, etc., can be used as luminescent dopants, but are not limited to these.

[0211] In one exemplary embodiment of this specification, the dopant is a metal complex compound.

[0212] In one exemplary embodiment of this specification, the dopant is a platinum complex compound.

[0213] In one exemplary embodiment of this specification, the dopant is an iridium complex compound.

[0214] In one exemplary embodiment of this specification, the dopant material is a compound with the chemical formula D-1 or D-2, but is not limited thereto.

[0215] [Chemical Formula D-1]

[0216]

[0217] [Chemical formula D-2]

[0218]

[0219] In chemical formulas D-1 and D-2,

[0220] M is a transition metal.

[0221] A1, A3, A5, A6, K1, K2, and K3 may be the same or different, and are independently direct bonds; O; S; divalent ester group; substituted or unsubstituted alkylene group; substituted or unsubstituted divalent alkenyl group; substituted or unsubstituted diallyl group; substituted or unsubstituted arylene group; or substituted or unsubstituted heteroarylene group.

[0222] A2 and A4 may be the same or different, and are independently direct bonds; N; substituted or unsubstituted trivalent allyl; substituted or unsubstituted trivalent aryl; or substituted or unsubstituted trivalent heteroaryl, and

[0223] n is an integer, either 1 or 2, and if n is 2, the structures within the parentheses are either the same or different.

[0224] In one exemplary embodiment of this specification, M is iridium or platinum.

[0225] In this specification, ester group means -R701-C(=O)-OR702-.

[0226] In this specification, allyl means (R801)2C=CH-C(R802)2-.

[0227] R701, R702, R801, and R802 may be the same or different, and are independently hydrogen; deuterium; alkyl; aryl; or heteroaryl, and the definitions of alkyl, aryl, and heteroaryl are the same as those above.

[0228] In this specification, alkylene or trivalent alkyl means a divalent or trivalent group having two or three bonding sites in an alkyl group. The foregoing description of alkyl groups applies, except that alkylene or trivalent alkyl is a divalent or trivalent group.

[0229] In this specification, a trivalent aryl group refers to an aryl group having three bonding positions, i.e., a trivalent group. The foregoing description of aryl groups applies, except that a trivalent aryl group is a trivalent group.

[0230] In this specification, a trivalent heteroaryl group refers to a heteroaryl group having three bonding positions, i.e., a trivalent group. The foregoing description of heteroaryl groups applies, except that a trivalent heteroaryl group is a trivalent group.

[0231] In this specification, a divalent alkenyl group refers to an alkenyl group having two bonding positions, i.e., a divalent group. The foregoing description of alkenyl groups applies, except that a divalent alkenyl group is a divalent group.

[0232] In this specification, divalent allyl refers to an allyl group having two bonding positions, i.e., a divalent group. The foregoing description of allyl applies, except that divalent allyl is a divalent group.

[0233] In one exemplary embodiment of this specification, the dopant may be selected from the following structural formulas, but is not limited thereto.

[0234]

[0235]

[0236]

[0237]

[0238] In one exemplary embodiment of this specification, the organic layer includes an electron blocking layer.

[0239] In one exemplary embodiment of this specification, the organic layer further includes one or more of a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.

[0240] In one exemplary embodiment of this specification, the organic light-emitting device further includes one or more layers selected from a hole injection layer, a hole transport layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0241] In one exemplary embodiment of this specification, the organic light-emitting device includes: a first electrode; a second electrode disposed opposite to the first electrode; a light-emitting layer disposed between the first electrode and the second electrode; and two or more organic layers disposed between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode.

[0242] In one exemplary embodiment of this specification, two or more organic layers may include two or more selected from hole injection layer, hole transport layer, hole injection and transport layer, light emission layer, electron transport layer, electron injection layer, electron injection and transport layer, hole blocking layer, and electron blocking layer.

[0243] In one exemplary embodiment of this specification, two or more hole transport layers are included between the light-emitting layer and the first electrode. The two or more hole transport layers may contain the same or different materials.

[0244] In one exemplary embodiment of this specification, the first electrode is an anode or a cathode.

[0245] In one exemplary embodiment of this specification, the second electrode is a cathode or an anode.

[0246] In one exemplary embodiment of this specification, the organic light-emitting device can be an organic light-emitting device (normal type) having a structure in which an anode, one or more organic layers and a cathode are sequentially stacked on a substrate.

[0247] In one exemplary embodiment of this specification, the organic light-emitting device can be an organic light-emitting device (inverted type) having a structure in which a cathode, one or more organic layers and an anode are sequentially stacked on a substrate.

[0248] For example, the structure of the organic light-emitting device in the exemplary embodiments of this specification is shown in... Figure 1 and Figure 2 middle. Figure 1 and Figure 2 An exemplary organic light-emitting device, which is not limited, is shown.

[0249] Figure 1 An example of an organic light-emitting device in which a first electrode 2, an organic layer 4, and a second electrode 3 are sequentially stacked on a substrate 1 is shown. The aforementioned compound is contained within the organic layer.

[0250] Figure 2 The diagram illustrates the structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 10, and a second electrode 3 are sequentially stacked on a substrate 1. The aforementioned compound is contained within the electron blocking layer 7 and / or the light-emitting layer 8.

[0251] The organic light-emitting devices described herein can be prepared using materials and methods known in the art, except that the electron blocking layer and / or the light-emitting layer contain the aforementioned compounds, namely compounds of formula 1.

[0252] When an organic light-emitting device comprises multiple organic layers, the organic layers can be formed from the same or different materials.

[0253] For example, the organic light-emitting device of this specification can be fabricated by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. A metal, conductive metal oxide, or alloy thereof can be deposited on the substrate using PVD (physical vapor deposition) methods such as sputtering or electron beam evaporation to form an anode. An organic layer comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer can be formed on the anode. A material that can be used as a cathode can then be deposited on the organic layer to fabricate the device. Alternatively, an organic light-emitting device can be fabricated by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0254] Furthermore, in the fabrication of organic light-emitting devices, compounds of formula 1 can be formed into organic layers not only through vacuum deposition but also through solution coating. Solution coating methods include, but are not limited to, spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, and roll coating.

[0255] In addition to this method, organic light-emitting devices can also be fabricated by sequentially depositing cathode material, organic layer, and anode material on a substrate. However, the fabrication method is not limited to this.

[0256] As an anode material, a material with a high work function is preferred, which facilitates hole injection into the organic layer. Examples include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and so on, but are not limited thereto.

[0257] Preferably, the cathode material is a material with a low work function, which facilitates electron injection into the organic layer. Examples include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures, such as LiF / Al or LiO2 / Al, but not limited thereto.

[0258] The light-emitting layer may comprise a host material and a dopant material. When the organic light-emitting device in an exemplary embodiment of this specification includes an additional light-emitting layer besides the light-emitting layer comprising a compound of Formula 1, the host material may include fused aromatic ring derivatives, heterocyclic compounds, etc. Specifically, fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0259] Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are fused aromatic ring derivatives having substituted or unsubstituted arylamine groups, and include pyrene, anthracene, etc., having arylamine groups. Examples include diindrone pyrene, etc. Furthermore, styrylamine compounds are compounds in which at least one aryl vinyl group is substituted in a substituted or unsubstituted arylamine. The substituents are selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups, and are either substituted or unsubstituted. Specifically, styrylamine compounds can be styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but are not limited thereto. In addition, metal complexes can include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0260] The hole injection layer is a layer that receives holes from the electrode. Specifically, as a hole injection material, materials that have the ability to transport holes and exhibit excellent hole-receiving effects from the anode, as well as excellent hole injection effects on the light-emitting layer or light-emitting material, are desirable. Furthermore, materials with excellent ability to prevent excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material are desirable. Additionally, materials with excellent thin-film forming capabilities are desirable. Furthermore, it is desirable that the HOMO (highest occupied molecular orbital) of the hole injection material be between the work function of the anode material and the HOMO of the adjacent organic layer. Specific examples of hole injection materials include metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, and others. Organic materials, conductive polymers based on polythiophene such as anthraquinone and polyaniline, etc., but not limited to these.

[0261] In one exemplary embodiment of this specification, the hole injection layer comprises a compound represented by the chemical formula HI-1, but is not limited thereto.

[0262] [Chemical formula HI-1]

[0263]

[0264] In the chemical formula HI-1,

[0265] R315 to R317 may be the same or different, and are independently selected from: hydrogen; deuterium; substituted or unsubstituted alkyl groups; substituted or unsubstituted aryl groups; substituted or unsubstituted heteroaryl groups; substituted or unsubstituted diarylamino groups; and combinations thereof, or bonded to adjacent groups to form substituted or unsubstituted rings.

[0266] r315 is an integer from 1 to 5, and if r315 is 2 or greater, then two or more r315 are the same or different.

[0267] r316 is an integer from 1 to 5, and if r316 is 2 or greater, then two or more R316 are the same or different.

[0268] In one exemplary embodiment of this specification, R317 is selected from any of the following: substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; substituted or unsubstituted diarylamine; and combinations thereof.

[0269] In one exemplary embodiment of this specification, R317 is selected from any of the following: carbazole; phenyl; biphenyl; triphenylene; diphenylamino; and combinations thereof.

[0270] In one exemplary embodiment of this specification, R315 and R316 may be the same or different, and are independently substituted or unsubstituted aryl groups, or bonded to adjacent groups to form aryl or alkyl-substituted aromatic hydrocarbon rings.

[0271] In one exemplary embodiment of this specification, R315 and R316 may be the same or different, independently phenyl or biphenyl, or bonded to adjacent groups to form phenyl or methyl-substituted indenyl groups.

[0272] In one exemplary embodiment of this specification, the chemical formula HI-1 is represented by any of the following compounds.

[0273]

[0274] In one exemplary embodiment of this specification, the hole injection layer comprises a compound represented by the chemical formula HI-2, but is not limited thereto.

[0275] [Chemical formula HI-2]

[0276]

[0277] In the chemical formula HI-2,

[0278] R401 to R403 may be the same or different, and are independently halogen groups, and

[0279] r401 to r403 are 4.

[0280] In one exemplary embodiment of this specification, R401 to R403 are F.

[0281] In one exemplary embodiment of this disclosure, the chemical formula HI-2 is represented by the following compound.

[0282]

[0283] In one exemplary embodiment of this specification, the hole injection layer comprises a compound represented by chemical formula HI-1 and a compound represented by chemical formula HI-2.

[0284] In one exemplary embodiment of this specification, the hole injection layer comprises a compound represented by chemical formula HI-1 and a compound represented by chemical formula HI-2 in a weight ratio of 1:99 to 99:1.

[0285] A hole transport layer is a layer that receives holes from a hole injection layer and transports them to a light-emitting layer. Materials with high hole mobility are desirable as hole transport materials, capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated segments.

[0286] In one exemplary embodiment of this specification, the hole transport layer comprises a compound represented by the chemical formula HI-1, but is not limited thereto.

[0287] In one exemplary embodiment of this specification, the hole injection and transport layer is a layer that transports holes to the light-emitting layer. Materials exemplified for the hole transport and hole injection layers can be used, but are not limited thereto.

[0288] The electron transport layer is the layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. Materials with high electron mobility that can effectively receive electrons from the cathode and transport them to the light-emitting layer are desirable as electron transport materials. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavonoid-metal complexes, etc. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, suitable cathode materials are conventional materials with low work functions, followed by an aluminum or silver layer. Specifically, it can be cesium, barium, calcium, ytterbium, samarium, etc., and in each case followed by an aluminum or silver layer.

[0289] The electron injection layer is the layer that receives electrons from the electrodes. As an electron injection material, materials with excellent electron transport capabilities, excellent electron reception effects from the second electrode, and excellent electron injection effects on the light-emitting layer or light-emitting material are desirable. Furthermore, materials that prevent excitons generated in the light-emitting layer from migrating to the hole injection layer and possess excellent thin film formation capabilities are also desirable. Specifically, electron injection materials can be fluorenone, anthraquinone dimethane, biphenylquinone, thiamethoxam dioxide, etc. azole, diazole, triazole, imidazole Tetracarboxylic acids, fluorenemethane, anthrone, and their derivatives; metal complex compounds; nitrogen-containing five-membered ring derivatives; and so on, but not limited to these.

[0290] Metal complex compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)chlorogallium, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc., but are not limited to these.

[0291] In one exemplary embodiment of this specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. When the organic light-emitting device includes an electron injection and transport layer other than an electron injection and transport layer comprising a compound of Formula 1, the materials exemplified above in the electron transport layer and electron injection layer may be used, but are not limited thereto.

[0292] In one exemplary embodiment of this specification, the electron injection and transport layer comprises a compound represented by the chemical formula ET-1, but is not limited thereto.

[0293] [Chemical formula ET-1]

[0294]

[0295] In the chemical formula ET-1,

[0296] At least one of Z11 to Z13 is N, and the rest are CH.

[0297] At least one of Z21 to Z23 is N, and the rest are CH.

[0298] L601 and L602 may be the same or different, and are independently direct bonds; substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups, and

[0299] Ar601 to Ar604 may be the same or different, and are independently substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups.

[0300] In one exemplary embodiment of this specification, L601 and L602 may be the same or different, and are independently substituted or unsubstituted C. 6-30 Monocyclic or polycyclic aryl groups.

[0301] In one exemplary embodiment of this specification, L601 and L602 are phenylene oxides.

[0302] In one exemplary embodiment of this specification, Ar601 to Ar604 may be the same or different, and are independently substituted or unsubstituted C. 6-30 Monocyclic or polycyclic aryl groups.

[0303] In one exemplary embodiment of this specification, Ar601 to Ar604 may be the same or different, and are independently phenyl; or biphenyl.

[0304] In one exemplary embodiment of this disclosure, the chemical formula ET-1 is represented by the following compound.

[0305]

[0306] In one exemplary embodiment of this specification, the electron injection and transport layer may further comprise a metal complex compound. The metal complex compound is the same as described above.

[0307] An electron blocking layer is a layer that improves device lifetime and efficiency by preventing electrons injected from the electron injection layer from passing through the light-emitting layer into the hole injection layer. When the electron blocking layer includes an additional electron blocking layer besides one comprising a compound of Formula 1 according to an exemplary embodiment of this specification, any known material may be used without limitation. Materials illustrated in the description of the hole injection layer may be used, but are not limited thereto. The electron blocking layer may be formed between the light-emitting layer and the hole transport layer, between the light-emitting layer and the hole injection layer, or between the light-emitting layer and both the hole injection and transport layers.

[0308] A hole-blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed under the same conditions as the electron-injection layer. Specifically, it can be used... Diazole derivatives, triazole derivatives, phenanthrene-rhein derivatives, aluminum complexes, etc., but not limited to these.

[0309] In one exemplary embodiment of this specification, the hole-blocking layer comprises a compound represented by the chemical formula HB-1, but is not limited thereto.

[0310] [Chemical formula HB-1]

[0311]

[0312] In the chemical formula HB-1,

[0313] L701 is a direct bond; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0314] T1 to T3 may be the same or different, and are independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

[0315] In one exemplary embodiment of this specification, Q1 to Q3 are N.

[0316] In one exemplary embodiment of this specification, L701 is a direct key; or a substituted or unsubstituted C. 6-30 Alpha-aryl.

[0317] In one exemplary embodiment of this specification, L701 is a direct bond; or an aryl group.

[0318] In one exemplary embodiment of this specification, L701 is a direct key; or C 6-30 Alpha-aryl.

[0319] In one exemplary embodiment of this specification, L701 is a direct bond; or a phenylene oxide.

[0320] In one exemplary embodiment of this specification, T1 to T3 may be the same or different, and are independently substituted or unsubstituted heteroaryl groups.

[0321] In one exemplary embodiment of this specification, T1 to T3 may be the same or different, and are independently substituted or unsubstituted C. 6-30 Monocyclic or polycyclic heteroaryl groups.

[0322] In one exemplary embodiment of this specification, T1 to T3 may be the same or different, and are independently heteroaryl.

[0323] In one exemplary embodiment of this specification, T1 to T3 may be the same or different, and are independently C. 6-30 Monocyclic or polycyclic heteroaryl groups.

[0324] In one exemplary embodiment of this specification, T1 to T3 are carbazole groups.

[0325] In one exemplary embodiment of this specification, the chemical formula HB-1 may include, but is not limited to, the following compounds.

[0326]

[0327] In one exemplary embodiment of this specification, the compound of chemical formula HB-1 can also be used as a second host material for the luminescent layer.

[0328] Depending on the materials used, the organic light-emitting device according to this specification can be a front-emitting, rear-emitting, or dual-sided emitting type.

[0329] The organic light-emitting devices according to this specification can be included and used in various electronic devices. For example, electronic devices can be display panels, touch panels, solar modules, lighting devices, etc., but are not limited thereto.

[0330] Invention Embodiments

[0331] The present disclosure is described in detail below by way of examples. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of this application should not be construed as limited to the embodiments described below. The embodiments of the present disclosure are provided to more fully illustrate the present disclosure to those skilled in the art.

[0332] Preparation Example

[0333] Preparation Example 1. Preparation of Compound F-1

[0334]

[0335] Synthesis of compound I-1

[0336] Under a nitrogen atmosphere, 20 g of 2'-bromo-4'-fluoro-1,1':3',1''-terphenyl, 10.2 g of 9H-carbazole, 32.4 g of potassium phosphate, and 300 mL of dimethylacetamide were stirred at 140 °C for 6 hours. After the reaction was complete, the reaction solution was placed in water, filtered, separated with toluene, and then treated with anhydrous MgSO4 before filtration. The filtered solution was recrystallized to obtain 23.1 g of compound I-1 (yield 80%, mass [M]). + ]=474).

[0337] Synthesis of compound F-1

[0338] Under a nitrogen atmosphere, 20 g of compound I-1, 14 g of 9H-3,9'-bicarbazole, 0.2 g of bis(tri-tert-butylphosphine)palladium(O), 10.2 g of sodium tert-butoxide, and 400 mL of xylene were heated under reflux and stirred for 8 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 17.2 g of compound F-1 (yield 56%, mass [M]). + ]=726).

[0339] Preparation Example 2. Preparation of Compound F-2

[0340]

[0341] Synthesis of compound I-2

[0342] Under a nitrogen atmosphere, 20 g of 2'-bromo-5'-fluoro-1,1':3',1''-terphenyl, 10.2 g of 9H-carbazole, 32.4 g of potassium phosphate, and 300 mL of dimethylacetamide were stirred at 140 °C for 6 hours. After the reaction was complete, the reaction solution was placed in water, filtered, separated with toluene, and then treated with anhydrous MgSO4 before filtration. The filtered solution was recrystallized to obtain 22.1 g of compound I-2 (yield 76%, mass [M]). + ]=474).

[0343] Synthesis of compound F-2

[0344] Under a nitrogen atmosphere, 20 g of compound I-2, 14 g of 9H-3,9'-bicarbazole, 0.2 g of bis(tri-tert-butylphosphine)palladium(O), 10.2 g of sodium tert-butoxide, and 400 mL of xylene were heated under reflux and stirred for 8 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 17.4 g of compound F-2 (yield 57%, mass [M]). + ]=726).

[0345] Preparation Example 3. Preparation of Compound F-3

[0346]

[0347] Synthesis of compound I-3

[0348] Under a nitrogen atmosphere, 20 g of 2'-bromo-6'-fluoro-1,1':4',1''-terphenyl, 10.2 g of 9H-carbazole, 32.4 g of potassium phosphate, and 300 mL of dimethylacetamide were stirred at 140 °C for 6 hours. After the reaction was complete, the reaction solution was placed in water, filtered, separated with toluene, and then treated with anhydrous MgSO4 before filtration. The filtered solution was recrystallized to obtain 22.4 g of compound I-3 (yield 77%, mass [M]). + ]=474).

[0349] Synthesis of compound F-3

[0350] Under a nitrogen atmosphere, 20 g of compound I-3, 14 g of 9H-3,9'-bicarbazole, 0.2 g of bis(tri-tert-butylphosphine)palladium(O), 10.2 g of sodium tert-butoxide, and 400 mL of xylene were heated under reflux and stirred for 8 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 18.2 g of compound F-3 (yield 59%, mass [M]). + ]=726).

[0351] Preparation Example 4. Preparation of Compound F-4

[0352]

[0353] Synthesis of compound I-4

[0354] Under a nitrogen atmosphere, 20 g of 2'-bromo-5'-fluoro-1,1':4',1''-terphenyl, 10.2 g of 9H-carbazole, 32.4 g of potassium phosphate, and 300 mL of dimethylacetamide were stirred at 140 °C for 6 hours. After the reaction was complete, the reaction solution was placed in water, filtered, separated with toluene, and then treated with anhydrous MgSO4 before filtration. The filtered solution was recrystallized to obtain 20.4 g of compound I-4 (yield 70%, mass [M]). + ]=474).

[0355] Synthesis of compound F-4

[0356] Under a nitrogen atmosphere, 20 g of compound I-4, 14 g of 9H-3,9'-bicarbazole, 0.2 g of bis(tri-tert-butylphosphine)palladium(O), 10.2 g of sodium tert-butoxide, and 400 mL of xylene were heated under reflux and stirred for 8 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 17.3 g of compound F-4 (yield 57%, mass [M]). + ]=726).

[0357] Preparation Example 5. Preparation of Compound F-5

[0358]

[0359] Synthesis of compound I-5

[0360] Under a nitrogen atmosphere, 20 g of 2'-bromo-3'-fluoro-1,1':4',1''-terphenyl, 10.2 g of 9H-carbazole, 32.4 g of potassium phosphate, and 300 mL of dimethylacetamide were stirred at 140 °C for 6 hours. After the reaction was complete, the reaction solution was placed in water, filtered, separated with toluene, and then treated with anhydrous MgSO4 before filtration. The filtered solution was recrystallized to obtain 21.1 g of compound I-5 (yield 73%, mass [M]). + ]=474).

[0361] Synthesis of compound F-5

[0362] Under a nitrogen atmosphere, 20 g of compound I-5, 14 g of 9H-3,9'-bicarbazole, 0.2 g of bis(tri-tert-butylphosphine)palladium(O), 10.2 g of sodium tert-butoxide, and 400 mL of xylene were heated under reflux and stirred for 8 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 17.9 g of compound F-5 (yield 58%, mass [M]). + ]=726).

[0363] Preparation Example 6. Preparation of Compound F-6

[0364]

[0365] Synthesis of compound I-6

[0366] Under a nitrogen atmosphere, 20 g of 4'-bromo-2'-fluoro-1,1':3',1''-terphenyl, 10.2 g of 9H-carbazole, 32.4 g of potassium phosphate, and 300 mL of dimethylacetamide were stirred at 140 °C for 6 hours. After the reaction was complete, the reaction solution was placed in water, filtered, separated with toluene, and then treated with anhydrous MgSO4 before filtration. The filtered solution was recrystallized to obtain 20.8 g of compound I-6 (yield 72%, mass [M]). + ]=474).

[0367] Synthesis of compound F-6

[0368] Under a nitrogen atmosphere, 20 g of compound I-6, 14 g of 9H-3,9'-bicarbazole, 0.2 g of bis(tri-tert-butylphosphine)palladium(O), 10.2 g of sodium tert-butoxide, and 400 mL of xylene were heated under reflux and stirred for 8 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 16.5 g of compound F-6 (yield 54%, mass [M]). + ]=726).

[0369] Preparation Example 7. Preparation of Compound F-7

[0370]

[0371] Synthesis of compound I-7

[0372] Under a nitrogen atmosphere, 20 g of 4'-bromo-6'-fluoro-1,1':3',1''-terphenyl, 10.2 g of 9H-carbazole, 32.4 g of potassium phosphate, and 300 mL of dimethylacetamide were stirred at 140 °C for 6 hours. After the reaction was complete, the reaction solution was placed in water, filtered, separated with toluene, and then treated with anhydrous MgSO4 before filtration. The filtered solution was recrystallized to obtain 21 g of compound I-7 (yield 72%, mass [M]). + ]=474).

[0373] Synthesis of compound F-7

[0374] Under a nitrogen atmosphere, 20 g of compound I-7, 14 g of 9H-3,9'-bicarbazole, 0.2 g of bis(tri-tert-butylphosphine)palladium(O), 10.2 g of sodium tert-butoxide, and 400 mL of xylene were heated under reflux and stirred for 8 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 16.9 g of compound F-7 (yield 55%, mass [M]). + ]=726).

[0375] Preparation Example 8. Preparation of Compound F-8

[0376]

[0377] Synthesis of compound I-8

[0378] Under a nitrogen atmosphere, 20 g of 4'-bromo-5'-fluoro-1,1':3',1''-terphenyl, 10.2 g of 9H-carbazole, 32.4 g of potassium phosphate, and 300 mL of dimethylacetamide were stirred at 140 °C for 6 hours. After the reaction was complete, the reaction solution was placed in water, filtered, separated with toluene, and then treated with anhydrous MgSO4 before filtration. The filtered solution was recrystallized to obtain 22 g of compound I-8 (yield 76%, mass [M]). + ]=474).

[0379] Synthesis of compound F-8

[0380] Under a nitrogen atmosphere, 20 g of compound I-8, 14 g of 9H-3,9'-bicarbazole, 0.2 g of bis(tri-tert-butylphosphine)palladium(O), 10.2 g of sodium tert-butoxide, and 400 mL of xylene were heated under reflux and stirred for 8 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 17.5 g of compound F-8 (yield 57%, mass [M]). + ]=726).

[0381] Preparation Example 9. Preparation of Compound F-9

[0382]

[0383] Synthesis of compound I-9

[0384] Under a nitrogen atmosphere, 20 g of 5'-bromo-2'-fluoro-1,1':3',1''-terphenyl, 10.2 g of 9H-carbazole, 32.4 g of potassium phosphate, and 300 mL of dimethylacetamide were stirred at 140 °C for 6 hours. After the reaction was complete, the reaction solution was placed in water, filtered, separated with toluene, and then treated with anhydrous MgSO4 before filtration. The filtered solution was recrystallized to obtain 21.5 g of compound I-9 (yield 74%, mass [M]). + ]=474).

[0385] Synthesis of compound F-9

[0386] Under a nitrogen atmosphere, 20 g of compound I-9, 14 g of 9H-3,9'-bicarbazole, 0.2 g of bis(tri-tert-butylphosphine)palladium(O), 10.2 g of sodium tert-butoxide, and 400 mL of xylene were heated under reflux and stirred for 8 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 18.3 g of compound F-9 (yield 60%, mass [M]). + ]=726).

[0387] Preparation Example 10. Preparation of Compound F-10

[0388]

[0389] Synthesis of compound I-10

[0390] Under a nitrogen atmosphere, 20 g of 5'-bromo-4'-fluoro-1,1':3',1''-terphenyl, 10.2 g of 9H-carbazole, 32.4 g of potassium phosphate, and 300 mL of dimethylacetamide were stirred at 140 °C for 6 hours. After the reaction was complete, the reaction solution was placed in water, filtered, separated with toluene, and then treated with anhydrous MgSO4 before filtration. The filtered solution was recrystallized to obtain 20.6 g of compound I-10 (yield 71%, mass [M]). + ]=474).

[0391] Synthesis of compound F-10

[0392] Under a nitrogen atmosphere, 20 g of compound I-10, 14 g of 9H-3,9'-bicarbazole, 0.2 g of bis(tri-tert-butylphosphine)palladium(O), 10.2 g of sodium tert-butoxide, and 400 mL of xylene were heated under reflux and stirred for 8 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 17.7 g of compound F-10 (yield 58%, mass [M]). + ]=726).

[0393] Preparation Example 11. Preparation of Compound F-11

[0394]

[0395] Synthesis of compound I-11

[0396] Under a nitrogen atmosphere, 20 g of 4'-bromo-3'-fluoro-1,1':2',1''-terphenyl, 10.2 g of 9H-carbazole, 32.4 g of potassium phosphate, and 300 mL of dimethylacetamide were stirred at 140 °C for 6 hours. After the reaction was complete, the reaction solution was placed in water, filtered, separated with toluene, and then treated with anhydrous MgSO4 before filtration. The filtered solution was recrystallized to obtain 22 g of compound I-11 (yield 76%, mass [M]). + ]=474).

[0397] Synthesis of compound F-11

[0398] Under a nitrogen atmosphere, 20 g of compound I-11, 14 g of 9H-3,9'-bicarbazole, 0.2 g of bis(tri-tert-butylphosphine)palladium(O), 10.2 g of sodium tert-butoxide, and 400 mL of xylene were heated under reflux and stirred for 8 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 18.2 g of compound F-11 (yield 59%, mass [M]). + ]=726).

[0399] Preparation Example 12. Preparation of Compound F-12

[0400]

[0401] Synthesis of compound I-12

[0402] Under a nitrogen atmosphere, 20 g of 4'-bromo-5'-fluoro-1,1':2',1''-terphenyl, 10.2 g of 9H-carbazole, 32.4 g of potassium phosphate, and 300 mL of dimethylacetamide were stirred at 140 °C for 6 hours. After the reaction was complete, the reaction solution was placed in water, filtered, separated with toluene, and then treated with anhydrous MgSO4 before filtration. The filtered solution was recrystallized to obtain 21.3 g of compound I-12 (yield 73%, mass [M]). + ]=474).

[0403] Synthesis of compound F-12

[0404] Under a nitrogen atmosphere, 20 g of I-12, 14 g of 9H-3,9'-bicarbazole, 0.2 g of bis(tri-tert-butylphosphine)palladium(O), 10.2 g of sodium tert-butoxide, and 400 mL of xylene were heated under reflux and stirred for 8 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 19.4 g of compound F-12 (yield 63%, mass [M]). + ]=726).

[0405] Preparation Example 13. Preparation of Compound F-13

[0406]

[0407] Synthesis of compound I-13

[0408] Under a nitrogen atmosphere, 20 g of 5'-bromo-3'-fluoro-1,1':2',1''-terphenyl, 10.2 g of 9H-carbazole, 32.4 g of potassium phosphate, and 300 mL of dimethylacetamide were stirred at 140 °C for 6 hours. After the reaction was complete, the reaction solution was placed in water, filtered, separated with toluene, and then treated with anhydrous MgSO4 before filtration. The filtered solution was recrystallized to obtain 20.5 g of compound I-13 (yield 71%, mass [M]). + ]=474).

[0409] Synthesis of compound F-13

[0410] Under a nitrogen atmosphere, 20 g of I-13, 14 g of 9H-3,9'-bicarbazole, 0.2 g of bis(tri-tert-butylphosphine)palladium(O), 10.2 g of sodium tert-butoxide, and 400 mL of xylene were heated under reflux and stirred for 8 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 19 g of compound F-13 (yield 62%, mass [M]). + ]=726).

[0411] Preparation Example 14. Preparation of Compound F-14

[0412]

[0413] Under a nitrogen atmosphere, 10 g of compound F-2, 40 g of aqueous trifluoromethanesulfonic acid D2O solution, and 300 mL of trichlorobenzene were stirred at 140 °C for 2 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, filtered, and then stirred again at 140 °C for 2 hours after adding 40 g of aqueous trifluoromethanesulfonic acid D2O solution. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, filtered, and recrystallized to obtain 8.2 g of compound F-14 (yield 79%, mass [M]). + ]=757).

[0414] Preparation Example 15. Preparation of Compound F-15

[0415]

[0416] Under a nitrogen atmosphere, 10 g of compound F-3, 40 g of aqueous trifluoromethanesulfonic acid D2O solution, and 300 mL of trichlorobenzene were stirred at 140 °C for 2 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, filtered, and then stirred again at 140 °C for 2 hours after adding 40 g of aqueous trifluoromethanesulfonic acid D2O solution. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, filtered, and recrystallized to obtain 8.4 g of compound F-15 (yield 81%, mass [M]). + ]=756).

[0417] Preparation Example 16. Preparation of Compound F-16

[0418]

[0419] Under a nitrogen atmosphere, 10 g of compound F-7, 40 g of aqueous trifluoromethanesulfonic acid D2O solution, and 300 mL of trichlorobenzene were stirred at 140 °C for 2 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, filtered, and then stirred again at 140 °C for 2 hours after adding 40 g of aqueous trifluoromethanesulfonic acid D2O solution. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, filtered, and recrystallized to obtain 8.1 g of compound F-16 (yield 78%, mass [M]). + ]=758).

[0420] Preparation Example 17. Preparation of Compound F-17

[0421]

[0422] Under a nitrogen atmosphere, 10 g of compound F-8, 40 g of aqueous trifluoromethanesulfonic acid D2O solution, and 300 mL of trichlorobenzene were stirred at 140 °C for 2 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, filtered, and then stirred again at 140 °C for 2 hours after adding 40 g of aqueous trifluoromethanesulfonic acid D2O solution. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, filtered, and recrystallized to obtain 8.4 g of compound F-18 (yield 81%, mass [M]). + ]=757).

[0423] Preparation Example 18. Preparation of Compound F-18

[0424]

[0425] Under a nitrogen atmosphere, 10 g of compound F-13, 40 g of aqueous trifluoromethanesulfonic acid D2O solution, and 300 mL of trichlorobenzene were stirred at 140 °C for 2 hours. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, filtered, and then stirred again at 140 °C for 2 hours after adding 40 g of aqueous trifluoromethanesulfonic acid D2O solution. After the reaction was complete, the reaction solution was separated, treated with anhydrous MgSO4, filtered, and recrystallized to obtain 7.7 g of compound F-18 (yield 74%, mass [M]). + ]=759).

[0426] Device Examples

[0427] Example 1

[0428] A glass substrate coated with an 800 Å thick layer of ITO (indium tin oxide) was immersed in distilled water containing a cleaning agent and ultrasonically washed. The cleaning agent used was a product of Fischer Co. The distilled water used was water filtered twice through a filter available from Millipore Co. After washing the ITO for 30 minutes, ultrasonic cleaning with distilled water was repeated twice for 10 minutes each time. Following the distilled water cleaning, ultrasonic cleaning was performed using isopropanol, acetone, and methanol as solvents, followed by drying and transfer to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporator.

[0429] A hole injection layer was formed on an ITO transparent electrode by thermal vacuum deposition of HT1 and HI1 at a molar ratio of 95:5 to a thickness of 100 Å. A hole transport layer was formed by vacuum deposition of HT1 (300 Å) on the hole injection layer. Next, an electron blocking layer was formed by vacuum deposition of compound F-1 prepared in Preparation Example 1 to a thickness of 50 Å on the hole transport layer. Next, a light-emitting layer was formed by vacuum deposition of a 1:1 (weight ratio) mixture of BH (n-type host) and F-1 (p-type host) prepared in Preparation Example 1 as the host of the light-emitting layer, and BD as the dopant of the light-emitting layer, at a weight ratio of 70:30. A hole blocking layer was formed by vacuum deposition of BH (n-type) to a thickness of 50 Å on the light-emitting layer. Next, an electron injection and transport layer with a thickness of 300 Å was formed by vacuum deposition of ET1 and LiQ at a weight ratio of 1:1 on the hole blocking layer. The cathode was formed by sequentially depositing a 10 Å thick layer of lithium fluoride (LiF) and an 800 Å thick layer of aluminum on the electron injection and transport layers.

[0430]

[0431] In the above steps, the deposition rate of the organic material was maintained between 0.4 Å / s and 0.7 Å / s, the deposition rate of lithium fluoride at the cathode was maintained at 0.3 Å / s, and the deposition rate of aluminum was maintained at 2 Å / s. The vacuum level during deposition was maintained at 2 × 10⁻⁶. -7 Up to 5×10 -6 Entrust.

[0432] Examples 2 to 18

[0433] Organic light-emitting devices were prepared in the same manner as in Example 1, except that compounds listed in Table 1 were used instead of compound F-1 as the p-type host of the light-emitting layer.

[0434]

[0435]

[0436] Comparative Examples 1 to 5

[0437] Organic light-emitting devices were prepared in the same manner as in Example 1, except that compounds listed in Table 1 were used instead of compound 1 as the host of the light-emitting layer.

[0438]

[0439] When current was applied to the organic light-emitting devices prepared in Examples 1 to 18 and Comparative Examples 1 to 5, voltage, luminous efficiency (EQE), and lifetime (based on 1500 nits) were measured, and the results are shown in Table 1. Lifetime T90 refers to the time required for the brightness to decrease from the initial brightness (1500 nits) to 90%.

[0440] [Table 1]

[0441]

[0442] In Table 1, the organic light-emitting devices of Examples 1 to 18 comprise compounds of Formula 1 of this specification, wherein carbazole and bicarbazole are bonded to a benzene at the 2-position of a divalent triphenyl group at the center.

[0443] The chemical formula 1 described in this specification has a structure in which carbazole is bonded to a benzene ring (benzene at the 2-position of a divalent triphenyl) and is bonded to bicarbazole, and has a high triplet state energy. Organic light-emitting devices incorporating this structure feature low voltage, high efficiency, and long lifetime because hole injection and energy transfer to the dopant are efficient.

[0444] However, the organic light-emitting devices of Comparative Examples 1 to 3 contain compounds CM1 to CM3, which have a structure in which carbazole and bicarbazole are not bonded to the 2-position benzene of the divalent triphenyl group at the center. Therefore, the hole characteristics are relatively poor, and the balance between energy injection and transfer is altered. As a result, the efficiency and lifetime of the organic light-emitting devices are reduced. Furthermore, the organic light-emitting devices of Comparative Examples 4 and 5 contain compounds CM4 and CM5, which have low triplet state energies. When they are included in the organic light-emitting devices, energy transfer to the dopant is not efficient. Therefore, it is difficult to expect good performance from the organic light-emitting devices.

[0445] For these reasons, Examples 1 to 18 showed better performance than Comparative Examples 1 to 5.

[0446] While specific exemplary embodiments of this disclosure (p-type body of electron blocking layer and light emitting layer) have been described above, this disclosure is not limited thereto, and various modifications can be made within the scope of the claims and detailed description of this disclosure, and such modifications also fall within the scope of this disclosure.

Claims

1. A compound of chemical formula 1: [Chemical Formula 1] in R1 to R6 may be the same or different, and are independently hydrogen; deuterium; or substituted or unsubstituted aryl groups. D stands for deuterium. r1 and r3 through r6 are each integers from 1 to 4. r2 is an integer from 1 to 3. If each of r1 to r6 is 2 or greater, then two or more of r1 to r6 are either the same or different. x1 is an integer from 0 to 2, and x2 and x3 are each integers from 0 to 5.

2. The compound according to claim 1, wherein chemical formula 1 is any one of chemical formulas 2 to 4: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] in D, R1 to R6, r1 to r6 and x1 to x3 are the same as those defined in Chemical Formula 1.

3. The compound according to claim 1, wherein chemical formula 1 is any one of chemical formulas 2-1 to 2-5: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] [Chemical Formula 2-5] in D, R1 to R6, r1 to r6 and x1 to x3 are the same as those defined in Chemical Formula 1.

4. The compound according to claim 1, wherein chemical formula 1 is any one of chemical formulas 3-1 to 3-6: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] [Chemical Formula 3-5] [Chemical Formula 3-6] in D, R1 to R6, r1 to r6 and x1 to x3 are the same as those defined in Chemical Formula 1.

5. The compound according to claim 1, wherein chemical formula 1 is any one of chemical formulas 4-1 to 4-5: [Chemical Formula 4-1] [Chemical Formula 4-2] [Chemical Formula 4-3] [Chemical Formula 4-4] [Chemical Formula 4-5] in D, R1 to R6, r1 to r6 and x1 to x3 are the same as those defined in Chemical Formula 1.

6. The compound according to claim 1, wherein R1 to R6 are the same or different, and are independently hydrogen; or deuterium.

7. The compound according to claim 1, wherein chemical formula 1 is any of the following compounds: Where D=28~35 means that 28 to 35 deuterium atoms can be substituted in the compound.

8. An organic light-emitting device, comprising: First electrode; Second electrode; and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound according to any one of claims 1 to 7.

9. The organic light-emitting device according to claim 8, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer contains the compound.

10. The organic light-emitting device according to claim 8, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer contains the compound as the body of the light-emitting layer.

11. The organic light-emitting device of claim 9, wherein the light-emitting layer comprises a dopant, and the dopant comprises a phosphorescent dopant.

12. The organic light-emitting device according to claim 9, wherein the light-emitting layer is a blue light-emitting layer.

13. The organic light-emitting device of claim 8, wherein the organic layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer comprises the compound.

14. The organic light-emitting device of claim 8, wherein the organic layer comprises an electron blocking layer, and the electron blocking layer contains the compound.

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