Compound and organic light-emitting device comprising same

Abstract

The present specification relates to a compound of chemical formula 1 and an organic light-emitting device comprising same. The compound enables the organic light-emitting device to have improved efficiency, low driving voltage, and / or improved lifespan characteristic. In particular, the compound described in the present specification can be used as a material for a light-emitting layer. In addition, the effects of a lower driving voltage, higher efficiency, and / or longer lifespan relative to those of a conventional organic light-emitting device can be achieved.

Description

Compound and organic light-emitting device containing the same

[0001] This application claims the benefit of Korean Patent Application No. 10-2024-0088475 filed with the Korean Intellectual Property Office on July 4, 2024, the entire contents of which are incorporated herein by reference.

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

[0003] In general, organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light emitting devices that utilize the organic light emitting phenomenon typically have a structure that includes an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and can be composed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons are formed, and when these excitons fall back to the ground state, light is emitted.

[0004] There is a continuing need for the development of new materials for organic light-emitting devices such as the above.

[0005] The present specification provides a compound and an organic light-emitting device comprising the same.

[0006] One embodiment of the present disclosure provides a compound of the following chemical formula 1.

[0007] [Chemical Formula 1]

[0008]

[0009] In the above chemical formula 1,

[0010] m and n are 0 or 1, respectively,

[0011] m+n is 1,

[0012] D is deuterium,

[0013] x1, x3, x4 and x7 are integers from 0 to 4, respectively.

[0014] x2 is an integer from 0 to 3,

[0015] x5 and x6 are integers from 0 to 5, respectively.

[0016] x8 is an integer from 0 to 8,

[0017] In the above chemical formula 1 The deuterium substitution rate is over 90%,

[0018] * is a site that is bonded to the above chemical formula 1.

[0019] In addition, one embodiment of the present specification provides an organic light-emitting device including a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers includes the compound described above.

[0020] The compounds described herein can be used as materials for an organic layer of an organic light-emitting device. The compounds according to at least one embodiment of the present disclosure can improve efficiency, lower operating voltage, and / or enhance lifespan characteristics in an organic light-emitting device. In particular, the compounds described herein can be used as materials for a light-emitting layer. In addition, compared to existing organic light-emitting devices, they have the effects of lower operating voltage, higher efficiency, and / or longer lifespan.

[0021] Figures 1 and 2 illustrate examples of organic light-emitting devices according to one embodiment of the present specification.

[0022] Figure 3 is an MS graph of compound A.

[0023] [Explanation of symbols]

[0024] 1: Substrate

[0025] 2: First electrode

[0026] 3: Second electrode

[0027] 4: Organic layer

[0028] 5: Hole injection layer

[0029] 6: Hole transport layer

[0030] 7: Electron blocking layer

[0031] 8: Emissive layer

[0032] 9: Hole blocking layer

[0033] 10: Electron injection and transport layer

[0034] Hereinafter, the present specification will be described in more detail.

[0035] The present specification provides a compound of the above chemical formula 1.

[0036] According to an embodiment of the present disclosure, chemical formula 1 can prevent a host-guest electrostatic bonding state of an organic layer of an organic light-emitting device including the same by increasing the LUMO energy level of the compound including a biscarbazole structure. In addition, the phenyl group and phenylene-carbazole bonded to a specific position of the biscarbazole have a structural feature of stabilizing the excited and polaronic states of the chemical formula 1 by participating in the conjugation system through a hyperconjugation effect. Therefore, the chemical formula 1 can be included in the organic layer of the organic light-emitting device to improve efficiency, lower operating voltage, and improve lifespan characteristics.

[0037] In addition, the physicochemical properties such as chemical bond length related to deuterium are different from those of hydrogen, and the stretching amplitude of the CD bond is smaller than that of the CH bond, so the van der Waals radius of deuterium is smaller than that of hydrogen, and it can be shown that the CD bond is generally shorter and stronger than the CH bond. Therefore, in the chemical formula 1 above, Since the deuterium substitution rate is more than 90%, the energy of the ground state is lowered, and as the bond length of deuterium and carbon is shortened, the molecular hardcore volume is reduced, and accordingly, the electrical polarizability can be reduced, and by weakening the intermolecular interaction, the thin film volume can be increased. In addition, these characteristics can have the effect of lowering the crystallinity of the thin film, that is, creating an amorphous state, and can be generally effective in increasing the lifespan and operating characteristics of organic light-emitting devices, and the heat resistance can be improved compared to conventional organic light-emitting devices.

[0038] Unless otherwise defined herein, 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 invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, and in case of conflict, this specification, including definitions, will control unless a specific passage is cited. Furthermore, the materials, methods, and examples are illustrative only and not intended to be limiting.

[0039] Hereinafter, the compound of the above chemical formula 1 will be described in detail.

[0040] According to one embodiment of the present specification, m is 1 and n is 0.

[0041] According to one embodiment of the present specification, n is 1 and m is 0.

[0042] According to one embodiment of the present specification, the chemical formula 1 is the following chemical formula 1-1 or 1-2.

[0043] [Chemical Formula 1-1]

[0044]

[0045] [Chemical Formula 1-2]

[0046]

[0047] In the above chemical formulas 1-1 and 1-2,

[0048] The definitions of D and x1 to x8 are the same as those defined in the above chemical formula 1.

[0049] According to one embodiment of the present specification, the chemical formula 1 is any one of the following chemical formulas 2 to 4.

[0050] [Chemical Formula 2]

[0051]

[0052] [Chemical Formula 3]

[0053]

[0054] [Chemical Formula 4]

[0055]

[0056] In the above chemical formulas 2 to 4,

[0057] The definitions of m, n, D and x1 to x8 are the same as those defined in the chemical formula 1 above.

[0058] According to one embodiment of the present specification, the chemical formula 1 is any one of the following chemical formulas 2-1 to 2-8.

[0059] [Chemical Formula 2-1]

[0060]

[0061] [Chemical Formula 2-2]

[0062]

[0063] [Chemical Formula 2-3]

[0064]

[0065] [Chemical Formula 2-4]

[0066]

[0067] [Chemical Formula 2-5]

[0068]

[0069] [Chemical Formula 2-6]

[0070]

[0071] [Chemical Formula 2-7]

[0072]

[0073] [Chemical Formula 2-8]

[0074]

[0075] In the above chemical formulas 2-1 to 2-8,

[0076] The definitions of D and x1 to x8 are the same as those defined in the above chemical formula 1.

[0077] According to one embodiment of the present specification, the chemical formula 1 is any one of the following chemical formulas 3-1 to 3-8.

[0078] [Chemical Formula 3-1]

[0079]

[0080] [Chemical Formula 3-2]

[0081]

[0082] [Chemical Formula 3-3]

[0083]

[0084] [Chemical Formula 3-4]

[0085]

[0086] [Chemical Formula 3-5]

[0087]

[0088] [Chemical Formula 3-6]

[0089]

[0090] [Chemical Formula 3-7]

[0091]

[0092] [Chemical Formula 3-8]

[0093]

[0094] In the above chemical formulas 3-1 to 3-8,

[0095] The definitions of D and x1 to x8 are the same as those defined in the above chemical formula 1.

[0096] According to one embodiment of the present specification, the chemical formula 1 is any one of the following chemical formulas 4-1 to 4-8.

[0097] [Chemical Formula 4-1]

[0098]

[0099] [Chemical Formula 4-2]

[0100]

[0101] [Chemical Formula 4-3]

[0102]

[0103] [Chemical Formula 4-4]

[0104]

[0105] [Chemical Formula 4-5]

[0106]

[0107] [Chemical Formula 4-6]

[0108]

[0109] [Chemical Formula 4-7]

[0110]

[0111] [Chemical Formula 4-8]

[0112]

[0113] In the above chemical formulas 4-1 to 4-8,

[0114] The definitions of D and x1 to x8 are the same as those defined in the above chemical formula 1.

[0115] According to one embodiment of the present specification, the chemical formula 1 has one of the following structures.

[0116]

[0117]

[0118] According to one embodiment of the present specification, the chemical formula 1 has one of the following structures.

[0119]

[0120]

[0121] According to one embodiment of the present specification, the chemical formula 1 has one of the following structures.

[0122]

[0123]

[0124] According to one embodiment of the present specification, the chemical formula 1 The deuterium substitution rate is 90% to 93.33%.

[0125] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 43.5% to 100%.

[0126] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 45.1% to 100%.

[0127] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 50% to 100%.

[0128] According to one embodiment of the present specification, when x1 to x8 are 0, it means that hydrogen is bonded.

[0129] According to one embodiment of the present specification, x1 is 3 or 4.

[0130] According to one embodiment of the present specification, the x3 is 3 or 4.

[0131] According to one embodiment of the present specification, the x4 is 3 or 4.

[0132] According to one embodiment of the present specification, the x7 is 0.

[0133] According to one embodiment of the present specification, the x7 is 1.

[0134] According to one embodiment of the present specification, the x7 is 2.

[0135] According to one embodiment of the present specification, the x7 is 3.

[0136] According to one embodiment of the present specification, the x7 is 4.

[0137] According to one embodiment of the present specification, x2 is 2 or 3.

[0138] According to one embodiment of the present specification, the x5 is 0.

[0139] According to one embodiment of the present specification, the x5 is 1.

[0140] According to one embodiment of the present specification, the x5 is 2.

[0141] According to one embodiment of the present specification, the x5 is 3.

[0142] According to one embodiment of the present specification, the x5 is 4.

[0143] According to one embodiment of the present specification, the x5 is 5.

[0144] According to one embodiment of the present specification, the x6 is 0.

[0145] According to one embodiment of the present specification, the x6 is 1.

[0146] According to one embodiment of the present specification, the x6 is 2.

[0147] According to one embodiment of the present specification, the x6 is 3.

[0148] According to one embodiment of the present specification, the x6 is 4.

[0149] According to one embodiment of the present specification, the x6 is 5.

[0150] According to one embodiment of the present specification, the x8 is 0.

[0151] According to one embodiment of the present specification, the x8 is 1.

[0152] According to one embodiment of the present specification, the x8 is 2.

[0153] According to one embodiment of the present specification, the x8 is 3.

[0154] According to one embodiment of the present specification, the x8 is 4.

[0155] According to one embodiment of the present specification, the x8 is 5.

[0156] According to one embodiment of the present specification, the x8 is 6.

[0157] According to one embodiment of the present specification, the x8 is 7.

[0158] According to one embodiment of the present specification, the x8 is 8.

[0159] According to one embodiment of the present specification, the physicochemical properties such as chemical bond length related to deuterium are different from those of hydrogen, and the elongation amplitude of CD bond is smaller than that of CH bond, so the van der Waals radius of deuterium is smaller than that of hydrogen, and in general, CD bond can be shown to be shorter and stronger than CH bond. Therefore, in the chemical formula 1 Since the deuterium substitution rate is more than 90%, the energy of the ground state is lowered, and as the bond length of deuterium and carbon is shortened, the molecular hardcore volume is reduced, and accordingly, the electrical polarizability can be reduced, and by weakening the intermolecular interaction, the thin film volume can be increased. In addition, these characteristics can have the effect of lowering the crystallinity of the thin film, that is, creating an amorphous state, and can be generally effective in increasing the lifespan and operating characteristics of organic light-emitting devices, and the heat resistance can be improved compared to conventional organic light-emitting devices.

[0160] As used herein, “deuterium substitution,” “deuterium containing,” “deuterated,” or “deuterated” means that a hydrogen at a substitutable position of a compound is replaced with deuterium.

[0161] As used herein, “perdeuterated” means a compound or group in which all hydrogens in the molecule are replaced with deuterium, and has the same meaning as “100% deuterated.”

[0162] In the present specification, “X% deuterated”, “degree of deuteration X%”, or “deuterium substitution rate X%” means that X% of the hydrogens at substitutable positions in the structure are replaced with deuterium. For example, when the structure is dibenzofuran, “25% deuterated” of the dibenzofuran, “degree of deuteration 25%” of the dibenzofuran, or “deuterium substitution rate 25%” of the dibenzofuran means that 2 out of 8 hydrogens at substitutable positions of the dibenzofuran are replaced with deuterium.

[0163] In this specification, "degree of deuteration" or "deuterium substitution rate" refers to the degree of deuteration as measured by nuclear magnetic resonance spectroscopy ( 1It can be confirmed by known methods such as H NMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry).

[0164] Specifically, nuclear magnetic resonance spectroscopy ( 1 When analyzing the "degree of deuteration" or "deuterium substitution rate" by H NMR, add DMF (dimethylformamide) as an internal standard. 1 Through the integration ratio on H NMR, the degree of deuteration or deuterium substitution can be calculated from the total peak integration amount.

[0165] In addition, when analyzing the "degree of deuteration" or "deuterium substitution rate" through TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), the substitution rate can be calculated based on the maximum value (median value) of the distribution of molecular weights at the end of the reaction. For example, when analyzing the degree of deuteration of the following compound A, when the molecular weight of the following starting material is 506 and the maximum molecular weight value (median value) of the following compound A in the MS graph of FIG. 3 is 527, since 21 of the hydrogens (26) at the substitutable positions of the following starting material were substituted with deuterium, it can be calculated that approximately 81% of the hydrogens were deuterated.

[0166]

[0167] In this specification, D means deuterium.

[0168] According to one embodiment of the present specification, the chemical formula 1 is any one of the following compounds.

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177] In the above compound,

[0178] Dn is the number of deuterium atoms substituted in the compound in parentheses,

[0179] The above Dn is an integer from 14 to 31,

[0180] The deuterium substitution rates of the above compounds are 45.1% to 100%, respectively.

[0181] In addition, the present specification provides an organic light-emitting device comprising the compound described above.

[0182] When it is said in this specification that a member is located "on" another member, this includes not only cases where the member is in contact with the other member, but also cases where another member exists between the two members.

[0183] When a part in this specification is said to "include" a certain component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.

[0184] In this specification, the term "layer" is interchangeable with the term "film", which is commonly used in the present technical field, and refers to a coating covering a target area. The size of the "layer" is not limited, and each "layer" may have the same or different sizes. According to one embodiment, the size of the "layer" may be the same as the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.

[0185] In this specification, the meaning of a specific A material being included in a B layer includes both i) one or more A materials being included in one B layer and ii) the B layer being composed of one or more layers and the A material being included in one or more layers of the multiple B layers.

[0186] In this specification, the meaning that a specific A material is included in a C layer or a D layer means that i) the A material is included in at least one layer among one or more C layers, ii) the A material is included in at least one layer among one or more D layers, or iii) the A material is included in at least one C layer and at least one D layer, respectively.

[0187] In this specification, the term n-type refers to a material that is generally known to be capable of stealing electrons from a matrix material (material of the organic layer), but is not limited thereto. In other words, n-type can be defined as a material that has the property of donating electrons to the LUMO (lowest unoccupied molecular orbital) energy level of the matrix. On the other hand, a p-type is a material that receives electrons from the HOMO (highest occupied molecular orbital) energy level of a material located in the adjacent cathode direction when forming a single layer with only p-type materials, and creates holes in the material located in the adjacent cathode direction, or when a p-type material is doped into an arbitrary matrix, it is a material that receives electrons from the HOMO of the matrix material and creates holes in the HOMO of the matrix to that extent. To this end, when forming a layer with only p-type materials, the closer the HOMO level of the material located in the cathode direction is to the LUMO of the p-type material, the easier it is to steal electrons from the HOMO of the adjacent layer and create holes in the HOMO of the adjacent layer. Also, when a p-type is doped into an arbitrary matrix, the closer the LUMO of the p-type material is to the HOMO of the matrix, the easier it is to steal electrons and create holes in the matrix.

[0188] The present specification provides an organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound of the above chemical formula 1.

[0189] The organic layer of the organic light-emitting device of the present specification may be formed as a single-layer structure, but may also be formed as a multi-layer structure in which two or more organic layers are laminated. For example, it may 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 thereto and may include a smaller number of organic layers.

[0190] According to one embodiment of the present 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, the hole transport layer, or the hole injection and transport layer includes the compound.

[0191] According to one embodiment of the present specification, the organic layer includes an electron blocking layer, and the electron blocking layer includes the compound.

[0192] According to one embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer.

[0193] According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

[0194] According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host of the light-emitting layer.

[0195] According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a p-type host of the light-emitting layer.

[0196] According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a p-type phosphorescent host of the light-emitting layer.

[0197] According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host and further includes another host.

[0198] According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host and further includes a host and a dopant.

[0199] According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a first host and further includes a second host.

[0200] According to one embodiment of the present specification, the first host is a p-type host and the second host is an n-type host.

[0201] According to one embodiment of the present specification, the first host is a p-type phosphorescent host, and the second host is an n-type phosphorescent host.

[0202] According to one embodiment of the present specification, the light-emitting layer comprises a first host and a second host in a weight ratio of 2:8 to 8:2, and the first host is a compound of the chemical formula 1.

[0203] According to one embodiment of the present specification, the light-emitting layer includes a first host and a second host in a weight ratio of 1:1, and the first host is a compound of the chemical formula 1.

[0204] According to one embodiment of the present specification, the second host is a dibenzofuran compound.

[0205] According to one embodiment of the present specification, the second host is the following chemical formula HB-1.

[0206] According to one embodiment of the present specification, the second host is a dibenzofuran compound substituted with a triazine substituted with a carbazole group.

[0207] According to one embodiment of the present specification, the light-emitting layer further includes a dopant.

[0208] According to one embodiment of the present specification, the light-emitting layer includes a first host and a second host, and further includes a dopant.

[0209] According to one embodiment of the present specification, the dopant is a phosphorescent dopant.

[0210] According to one embodiment of the present specification, the dopant is included in an amount of 1 to 20 parts by weight based on 100 parts by weight of the host.

[0211] According to one embodiment of the present specification, the light-emitting layer includes a dopant, and the dopant includes a phosphorescent dopant.

[0212] According to one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host and a dopant, the host includes the compound, and the dopant includes the phosphorescent dopant.

[0213] According to one embodiment of the present specification, the light-emitting layer is a blue light-emitting layer.

[0214] According to one embodiment of the present specification, the maximum emission wavelength of the light-emitting layer is 420 nm to 495 nm.

[0215] According to one embodiment of the present 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 weight ratio of 99:1 to 50:50, and even more specifically, it comprises a weight ratio of 99:1 to 95:5.

[0216] When the above-mentioned light-emitting layer emits red light, a phosphorescent material such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or a fluorescent material such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the light-emitting dopant, but is not limited thereto. When the light-emitting layer emits green light, a phosphorescent material such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium), or a fluorescent material such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the light-emitting dopant, but is not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as a platinum complex compound or (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distriarylene (DSA), PFO polymer, or PPV polymer can be used as a light-emitting dopant, but is not limited thereto.

[0217] According to one embodiment of the present specification, the dopant is a metal complex compound.

[0218] According to one embodiment of the present specification, the dopant is a platinum complex compound.

[0219] According to one embodiment of the present specification, the dopant is an iridium complex compound.

[0220] According to one embodiment of the present specification, the dopant is represented by the following chemical formula D-1 or D-2, but is not limited thereto.

[0221] [Chemical Formula D-1]

[0222]

[0223] [Chemical Formula D-2]

[0224]

[0225] In the above chemical formulas D-1 and D-2,

[0226] M is a transition metal,

[0227] A1, A3, A5, A6, K1, K2 and K3 are the same or different from each other, and each independently represents a direct bond; O; S; a divalent ester group; a substituted or unsubstituted alkylene group; a substituted or unsubstituted divalent alkenyl group; a substituted or unsubstituted divalent allyl group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

[0228] A2 and A4 are the same or different, and each independently represents a direct bond; N; a substituted or unsubstituted trivalent alkylene group; a substituted or unsubstituted trivalent aryl group; or a substituted or unsubstituted trivalent heteroaryl group,

[0229] n is 1 or 2, and when n is 2, the structures within the parentheses are the same or different.

[0230] In this specification, means the connecting part.

[0231] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where the hydrogen atom is replaced, i.e., a position where the substituent can be replaced, and when two or more are replaced, the two or more substituents may be the same or different from each other.

[0232] The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; halogen group; cyano group; alkyl group; cycloalkyl group; alkoxy group; alkenyl group; haloalkyl group; silyl group; aryl group; and heteroaryl group, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or having no substituents.

[0233] In this specification, the connection of two or more substituents means that the hydrogen of one substituent is connected to another substituent. For example, the connection of two substituents means that a phenyl group and a naphthyl group are connected. or can be a substituent of. In addition, the connection of three substituents includes not only the case where (substituent 1)-(substituent 2)-(substituent 3) are connected sequentially, but also the case where (substituent 2) and (substituent 3) are connected to (substituent 1). For example, a phenyl group, a naphthyl group, and an isopropyl group are connected, , , or can be a substituent. The above definition also applies to cases where four or more substituents are connected.

[0234] In this specification, examples of halogen groups include a fluoro group, a chloro group, a bromo group, or an iodo group.

[0235] In this specification, the alkyl group may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, Examples thereof include, but are not limited to, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 4-methylhexyl group, and 5-methylhexyl group.

[0236] In the present specification, the cycloalkyl group is not particularly limited, but is preferably one having 3 to 30 carbon atoms, and specifically, includes, but is not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like.

[0237] In the present specification, the alkoxy group may be linear, branched, or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, an n-pentyloxy group, a neopentyloxy group, an isopentyloxy group, an n-hexyloxy group, a 3,3-dimethylbutyloxy group, a 2-ethylbutyloxy group, an n-octyloxy group, an n-nonyloxy group, an n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

[0238] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include, but are not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group.

[0239] In this specification, a haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the above alkyl group.

[0240] In the present specification, the aryl group is not particularly limited, but is preferably one having 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0241] When the above aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may include, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc.

[0242] When the above aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may include, but is not limited to, a naphthyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, phenalene group, perylene group, chrysene group, fluorene group, etc.

[0243] In the present specification, the fluorene group may be substituted, and adjacent groups may be combined with each other to form a ring.

[0244] Examples of the above fluorene group include There are, but are not limited to, the following.

[0245] In this specification, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent that is sterically closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.

[0246] In the present specification, a heteroaryl group includes one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine, phenanthroline, isoxazole group, thiadiazole group, Examples thereof include, but are not limited to, dibenzofuran group, dibenzosilole group, phenoxathiine group, phenoxazine group, phenothiazine group, dihydroindenocarbazole group, spirofluorenxanthene group, and spirofluorenethioxanthene group.

[0247] In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, etc. Among the alkylsilyl groups, the alkyl group may be applied with the examples of the alkyl group described above, among the arylsilyl groups, the aryl group may be applied with the examples of the aryl group described above, and among the heteroarylsilyl groups, the heteroaryl group may be applied with the examples of the heteroaryl group described above.

[0248] In this specification, an arylene group means a divalent group having two bonding positions to an aryl group. The description of the aryl group described above may be applied to these groups, except that each is a divalent group.

[0249] In this specification, a heteroarylene group means a divalent group having two bonding positions to a heteroaryl group. The description of the heteroaryl group described above may be applied to these groups, except that each is a divalent group.

[0250] According to one embodiment of the present specification, M is iridium or platinum.

[0251] In this specification, ester group means -R701-C(=O)-OR702-.

[0252] In this specification, allyl group means R(801)2C=CH-C(R802)2-.

[0253] The above R701, R702, R801 and R802 are the same as or different from each other, and each independently represents hydrogen; an alkyl group; an aryl group; or a heteroaryl group, and the definitions of the alkyl group, aryl group and heteroaryl group are the same as the examples of the substituents described above.

[0254] In this specification, an alkylene group or a trivalent alkylene group means a divalent or trivalent group having two or three bonding positions to an alkyl group. The description of the alkyl group described above may be applied to these groups, except that they are divalent or trivalent, respectively.

[0255] In this specification, a trivalent arylene group means a trivalent group having three bonding positions to an aryl group. The description of the aryl group described above may be applied to each of these groups, except that they are each trivalent.

[0256] In this specification, a trivalent heteroarylene group means a group having three bonding positions to a heteroaryl group, i.e., a trivalent group. Except that each of these groups is a trivalent group, the description of the heteroaryl group described above can be applied.

[0257] In this specification, a divalent alkenyl group means an alkenyl group having two bonding positions, i.e., a divalent group. The description of the alkenyl group described above may be applied to each of these groups, except that they are each divalent groups.

[0258] In this specification, a divalent allyl group means a group having two bonding positions to the allyl group, i.e., a divalent group. The description of the allyl group described above may be applied to each of these groups, except that they are each divalent groups.

[0259] According to one embodiment of the present specification, the chemical formula D-1 or D-2 may be selected from the following structural formulas, but is not limited thereto.

[0260]

[0261]

[0262]

[0263]

[0264] According to one embodiment of the present specification, the organic layer includes an electron blocking layer.

[0265] According to one embodiment of the present specification, the organic layer further includes at least one layer 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.

[0266] According to one embodiment of the present specification, the organic light-emitting device further includes one or two or more layers selected from the group consisting of 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.

[0267] According to one embodiment of the present specification, the organic light-emitting element includes a first electrode; a second electrode provided opposite the first electrode; a light-emitting layer provided between the first electrode and the second electrode; and two or more organic layers provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0268] According to one embodiment of the present specification, the two or more organic layers may be selected from the group consisting of 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.

[0269] According to one embodiment of the present 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 include materials that are the same or different from each other.

[0270] According to one embodiment of the present specification, the first electrode is an anode or a cathode.

[0271] According to one embodiment of the present specification, the second electrode is a cathode or an anode.

[0272] According to one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0273] According to one embodiment of the present specification, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0274] For example, the structure of an organic light-emitting device according to one embodiment of the present specification is illustrated in FIGS. 1 and 2. FIGS. 1 and 2 illustrate the organic light-emitting device and are not limited thereto.

[0275] Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode (2), an organic layer (4), and a second electrode (3) are sequentially laminated on a substrate (1). The compound is included in the organic layer.

[0276] FIG. 2 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 laminated on a substrate (1). The compound is included in the electron blocking layer (7) and / or the light-emitting layer (8).

[0277] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that the electron blocking layer and / or the light-emitting layer include the compound, i.e., the compound of the above chemical formula 1.

[0278] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0279] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a conductive metal oxide or an alloy thereof on the substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. In addition to this method, the organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on the substrate.

[0280] In addition, the compound of the above chemical formula 1 can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc.

[0281] In addition to this method, an organic light-emitting device can also be manufactured by sequentially depositing an organic layer, an anode material, and a cathode material on a substrate. However, the manufacturing method is not limited to this.

[0282] The anode material is preferably a material having a high work function to facilitate hole injection into the organic layer. Examples thereof include, but are not limited to, 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; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0283] The cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer. Examples thereof include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0284] The above-described light-emitting layer may include a host material and a dopant material. When the organic light-emitting device according to one embodiment of the present specification includes an additional light-emitting layer other than the light-emitting layer including the chemical formula 1, the host material may be a condensed aromatic ring derivative or a heterocycle-containing compound. Specifically, the condensed aromatic ring derivative may include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocycle-containing compounds may include, but are not limited to, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like.

[0285] The above dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group are substituted or unsubstituted. Specifically, the present invention includes, but is not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. In addition, the metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.

[0286] The above-mentioned hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injection material has the ability to transport holes, thereby having a hole receiving effect from the anode and an excellent hole injection effect into the light-emitting layer or light-emitting material. In addition, a material having an excellent ability to prevent the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material is preferable. In addition, a material having an excellent thin film forming ability is preferable. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, and arylamine series organic materials; hexanitrilehexaazatriphenylene series organic materials; quinacridone series organic materials; perylene series organic materials; There are conductive polymers of the polythiophene series, such as anthraquinone and polyaniline, but they are not limited thereto.

[0287] According to one embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following chemical formula HI-1.

[0288] [Chemical formula HI-1]

[0289]

[0290] In the above chemical formula HI-1,

[0291] R315 to R317 are the same or different, and each independently represent one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0292] r315 is an integer from 1 to 5, and when r315 is 2 or more, 2 or more R315 are the same as or different from each other,

[0293] r316 is an integer from 1 to 5, and when r316 is 2 or more, two or more R316 are the same as or different from each other.

[0294] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof.

[0295] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; a triphenylene group; and combinations thereof.

[0296] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, or combine with an adjacent group to form an aryl group or an aromatic hydrocarbon ring substituted with an alkyl group.

[0297] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a phenyl group or a biphenyl group, or combine with an adjacent group to form an indene substituted with a phenyl group or a methyl group.

[0298] According to one embodiment of the present specification, the chemical formula HI-1 is represented by any one of the following compounds.

[0299]

[0300]

[0301] According to one embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following chemical formula HI-2.

[0302] [Chemical formula HI-2]

[0303]

[0304] In the above chemical formula HI-2,

[0305] R401 to R403 are the same as or mentioned above, and each independently represents a halogen group,

[0306] r401 to r403 are 4.

[0307] According to one embodiment of the present specification, R401 to R403 are F.

[0308] According to one embodiment of the present specification, the chemical formula HI-2 is represented by the following compound.

[0309]

[0310] According to one embodiment of the present specification, the hole injection layer includes the chemical formulas HI-1 and HI-2.

[0311] According to one embodiment of the present specification, the hole injection layer comprises the chemical formulas HI-1 and HI-2 in a weight ratio of 1:99 to 99:1.

[0312] The above-mentioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transport them to the light-emitting layer, and a material with high hole mobility is preferable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0313] According to one embodiment of the present specification, the hole transport layer includes, but is not limited to, a compound represented by the chemical formula HI-1.

[0314] According to one embodiment of the present specification, the hole injection and transport layer is a layer that transports holes to the light-emitting layer. The materials exemplified in the hole transport layer and hole injection layer may be used, but are not limited thereto.

[0315] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is preferably a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is preferable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material, as used according to the prior art. In particular, suitable cathode materials are conventional materials having a low work function and followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case followed by an aluminum layer or a silver layer.

[0316] The electron injection layer is a layer that receives electrons from the electrode. It is preferable that the electron injection material have excellent electron transport ability, an electron receiving effect from the second electrode, and an excellent electron injection effect for the light-emitting layer or light-emitting material. In addition, a material that prevents excitons generated in the light-emitting layer from moving to the hole injection layer and has excellent thin film forming ability is preferable. Specific examples of the electron injection layer material include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0317] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, Examples include, but are not limited to, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc.

[0318] According to one embodiment of the present 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 in addition to the electron injection and transport layer including the compound of Chemical Formula 1, the materials exemplified in the electron transport layer and the electron injection layer may be used, but are not limited thereto.

[0319] According to one embodiment of the present specification, the electron injection and transport layer includes, but is not limited to, a compound represented by the following chemical formula ET-1.

[0320] [Chemical formula ET-1]

[0321]

[0322] In the above chemical formula ET-1,

[0323] At least one of Z11 to Z13 is N, and the rest are CH,

[0324] At least one of Z21 to Z23 is N, and the others are CH,

[0325] L601 and L602 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0326] Ar601 to Ar604 are the same or different, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0327] According to one embodiment of the present specification, L601 and L602 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0328] According to one embodiment of the present specification, L601 and L602 are phenylene groups.

[0329] According to one embodiment of the present specification, Ar601 to Ar604 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0330] According to one embodiment of the present specification, Ar601 to Ar604 are phenyl groups.

[0331] According to one embodiment of the present specification, the chemical formula ET-1 is represented by the following compound.

[0332]

[0333] According to one embodiment of the present specification, the electron injection and transport layer may further include a metal complex compound. The metal complex compound is as described above.

[0334] The electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light emitting layer and entering the hole injection layer. When the electron blocking layer includes an additional electron blocking layer in addition to the electron blocking layer including the compound of chemical formula 1 according to one embodiment of the present specification, known materials can be used without limitation, and the materials exemplified in the description of the hole injection layer can be used, but are not limited thereto. The electron blocking layer can 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 a layer that simultaneously injects and transports holes.

[0335] According to one embodiment of the present specification, the electron blocking layer includes, but is not limited to, a compound represented by the chemical formula HI-1.

[0336] The above hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

[0337] According to one embodiment of the present specification, the hole blocking layer includes, but is not limited to, a compound represented by the following chemical formula HB-1.

[0338] [Chemical formula HB-1]

[0339]

[0340] In the above HB-1,

[0341] L701 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0342] T1 to T3 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0343] According to one embodiment of the present specification, Q1 to Q3 are N.

[0344] According to one embodiment of the present specification, the L701 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0345] According to one embodiment of the present specification, the L701 is a direct bond; or an arylene group.

[0346] According to one embodiment of the present specification, L701 is a direct bond; or an arylene group having 6 to 30 carbon atoms.

[0347] According to one embodiment of the present specification, the L701 is a direct bond; or a phenylene group.

[0348] According to one embodiment of the present specification, T1 to T3 are the same as or different from each other, and are each independently a substituted or unsubstituted heteroaryl group.

[0349] According to one embodiment of the present specification, T1 to T3 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 6 to 30 carbon atoms.

[0350] According to one embodiment of the present specification, T1 to T3 are the same as or different from each other, and each independently is a heteroaryl group.

[0351] According to one embodiment of the present specification, T1 to T3 are the same as or different from each other, and each independently represents a monocyclic or polycyclic heteroaryl group having 6 to 30 carbon atoms.

[0352] According to one embodiment of the present specification, T1 to T3 are carbazole groups.

[0353] According to one embodiment of the present specification, the chemical formula HB-1 may include, but is not limited to, the following compounds.

[0354]

[0355] According to one embodiment of the present specification, the chemical formula HB-1 may also be used as a second host material of the light-emitting layer.

[0356] The organic light-emitting device according to the present specification may be a front-emitting, back-emitting or double-sided emitting device depending on the material used.

[0357] The organic light-emitting device according to the present specification can be incorporated into and used in various electronic devices. For example, the electronic devices may be, but are not limited to, display panels, touch panels, solar modules, lighting devices, etc.

[0358] Hereinafter, the present specification will be described in detail with examples and comparative examples. However, the examples and comparative examples according to the present specification may be modified in various different forms, and the scope of the present specification is not construed as being limited to the examples and comparative examples described below. The examples and comparative examples in this specification are provided to more fully explain the present specification to those with average knowledge in the art.

[0359] <Manufacturing Example 1: Synthesis of Compound 1>

[0360]

[0361] In a nitrogen atmosphere, compound 9-(4-bromophenyl)-9H-carbazole (3.50 g, 10.86 mmol) and compound a-1 (4.88 g, 11.41 mmol) were completely dissolved in 270 mL of xylene in a 500 mL round-bottom flask, and then NaOtBu (2.09 g, 21.72 mmol) was added and bis(tri-tert-butylphosphine)palladium(0) (0.17 g, 0.33 mmol) was added, followed by heating and stirring for 6 hours. The mixture was cooled to room temperature, filtered to remove the base, and xylene was concentrated under reduced pressure and recrystallized with 330 mL of ethyl acetate to prepare compound 1 (4.97 g, 68%).

[0362] MS[M+H] + = 669

[0363] <Manufacturing Example 2: Synthesis of Compound 2>

[0364]

[0365] In a nitrogen atmosphere, compound 9-(3-bromophenyl)-9H-carbazole (3.50 g, 10.86 mmol) and compound a-2 (4.88 g, 11.41 mmol) were completely dissolved in 250 mL of xylene in a 500 mL round-bottom flask, and then NaOtBu (2.09 g, 21.72 mmol) was added, followed by bis(tri-tert-butylphosphine)palladium(0) (0.17 g, 0.33 mmol), followed by heating and stirring for 4 hours. The mixture was cooled to room temperature, filtered to remove the base, and xylene was concentrated under reduced pressure and recrystallized with 300 mL of ethyl acetate to prepare compound 2 (4.42 g, 61%).

[0366] MS[M+H] + = 669

[0367] <Manufacturing Example 3: Synthesis of Compound 3>

[0368]

[0369] In a nitrogen atmosphere, compound 9-(2-bromophenyl)-9H-carbazole (3.50 g, 10.86 mmol) and compound a-1 (4.88 g, 11.41 mmol) were completely dissolved in 260 mL of xylene in a 500 mL round-bottom flask, and then NaOtBu (2.09 g, 21.72 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.17 g, 0.33 mmol) were added, followed by heating and stirring for 6 hours. The mixture was cooled to room temperature, filtered to remove the base, and xylene was concentrated under reduced pressure and recrystallized with 300 mL of ethyl acetate to prepare compound 3 (3.86 g, 53%).

[0370] MS[M+H]+= 669

[0371] <Manufacturing Example 4: Synthesis of Compound 4>

[0372]

[0373] In a nitrogen atmosphere, compound 9-(3-bromophenyl-2,4,5,6-d4)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (3.50 g, 10.47 mmol) and compound a-1 (4.70 g, 11.01 mmol) were completely dissolved in 250 mL of xylene in a 500 mL round-bottom flask, and then NaOtBu (2.01 g, 20.94 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 0.31 mmol) were added, followed by heating and stirring for 7 hours. The mixture was cooled to room temperature, filtered to remove the base, and xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare compound 4 (4.35 g, 61%).

[0374] MS[M+H] + = 681

[0375] <Manufacturing Example 5: Synthesis of Compound 5>

[0376]

[0377] In a nitrogen atmosphere, compound 9-(2-bromophenyl)-9H-carbazole (3.50 g, 10.86 mmol) and compound a-3 (4.88 g, 11.41 mmol) were completely dissolved in 260 mL of xylene in a 500 mL round-bottom flask, and then NaOtBu (2.09 g, 21.72 mmol) was added and bis(tri-tert-butylphosphine)palladium(0) (0.06 g, 0.11 mmol) was added, followed by heating and stirring for 4 hours. The mixture was cooled to room temperature, filtered to remove the base, and xylene was concentrated under reduced pressure and recrystallized with 260 mL of ethyl acetate to prepare compound 5 (4.03 g, 55%).

[0378] MS[M+H] + = 669

[0379] <Manufacturing Example 6: Synthesis of Compound 6>

[0380]

[0381] In a nitrogen atmosphere, compound (6'-chloro-[1,1':3',1''-terphenyl]-3-yl)triphenylsilane (3.50 g, 10.86 mmol) and compound a-4 (4.88 g, 11.41 mmol) were completely dissolved in 280 mL of xylene in a 500 mL round-bottom flask, and then NaOtBu (2.09 g, 21.72 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.17 g, 0.33 mmol) were added, followed by heating and stirring for 6 hours. The mixture was cooled to room temperature, filtered to remove the base, and xylene was concentrated under reduced pressure and recrystallized with 280 mL of ethyl acetate to prepare compound 6 (3.78 g, 52%).

[0382] MS[M+H] + = 669

[0383] <Preparation Example 7: Synthesis of Compound 7>

[0384]

[0385] In a 500 mL round-bottom flask under a nitrogen atmosphere, compound 9-(4-bromophenyl-2,3,5,6-d4)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (3.50 g, 10.47 mmol) and compound a-5 (4.70 g, 11.01 mmol) were completely dissolved in 260 mL of xylene, and then NaOtBu (2.01 g, 20.94 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 0.31 mmol) were added, followed by heating and stirring for 4 hours. The mixture was cooled to room temperature, filtered to remove the base, and xylene was concentrated under reduced pressure and recrystallized with 260 mL of ethyl acetate to prepare compound 7 (4.22 g, 59%).

[0386] MS[M+H] + = 681

[0387] <Preparation Example 8: Synthesis of Compound 8>

[0388]

[0389] In a 500 mL round-bottom flask under a nitrogen atmosphere, compound 9-(2-bromophenyl-3,4,5,6-d4)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (3.50 g, 10.47 mmol) and compound a-6 (4.70 g, 11.01 mmol) were completely dissolved in 260 mL of xylene, and then NaOtBu (2.01 g, 20.94 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.17 g, 0.33 mmol) were added, followed by heating and stirring for 6 hours. The mixture was cooled to room temperature, filtered to remove the base, and xylene was concentrated under reduced pressure and recrystallized with 270 mL of ethyl acetate to prepare compound 8 (4.51 g, 63%).

[0390] MS[M+H] + = 681

[0391] <Example 1-1>

[0392] A glass substrate coated with an 800Å thick ITO (indium tin oxide) film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent was a Fischer Co. product, and the distilled water was secondarily filtered using a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaned twice with distilled water for 10 minutes each. After washing with distilled water, ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition machine.

[0393] On the anode, which is an ITO transparent electrode, prepared in this way, the following compounds HT1 and HI1 were vacuum-deposited at a ratio of 98:2 (molar ratio) to a thickness of 100 Å to form a hole injection layer. On the hole injection layer, the following compound HT1 was vacuum-deposited (300 Å) to form a hole transport layer. Subsequently, the following compound EB1 was vacuum-deposited at a film thickness of 50 Å on the hole transport layer to form an electron blocking layer. Subsequently, on the electron blocking layer, a mixture of the following compound BH (n-type) and BH (p-type) represented by the compound 1 synthesized in Preparation Example 1 at a weight ratio of 1:1 and the following compound BD were vacuum-deposited at a weight ratio of 88:12 to form a light emitting layer with a thickness of 300 Å. The following compound BH (n-type) was vacuum-deposited at a film thickness of 50 Å on the light emitting layer to form a hole blocking layer. Next, on the hole blocking layer, the following compound ET1 and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 300 Å. On the electron injection and transport layer, lithium fluoride (LiF) was sequentially deposited with a thickness of 10 Å and aluminum was sequentially deposited with a thickness of 800 Å to form a cathode.

[0394]

[0395] In the above process, the deposition rate of organic materials was maintained at 0.4 to 0.7 Å / sec, lithium fluoride of the cathode was maintained at 0.3 Å / sec, and aluminum was maintained at 2 Å / sec, and the vacuum during deposition was 2×10 -7 ~ 5×10 -6 Torr was maintained, and an organic light-emitting device was fabricated.

[0396] <Examples 1-2 to 1-8>

[0397] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compounds described in Preparation Examples 1 to 8 were used instead of Compound 1.

[0398] <Comparative Examples 1-1 to 1-6>

[0399] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compounds described in Table 1 below were used instead of Compound 1. The compounds C1 to C6 used in Table 1 below are as follows.

[0400]

[0401] <Experimental Example>

[0402] When current was applied to the organic light-emitting devices manufactured in the above examples and comparative examples, the voltage, efficiency, color coordinates, and lifespan were measured, and the results are shown in Table 1 below. T 90 refers to the time required for the luminance to decrease from the initial luminance (1600 nit) to 90%.

[0403] Compound (p-type host of the light-emitting layer) voltage (V@10mA / cm 2 )Efficiency (cd / A@10mA / cm 2 )Color coordinates (x,y)T 90Example 1-1 Compound 13.91 16.3 (0.136, 0.156) 163 Example 1-2 Compound 23.82 17.2 (0.137, 0.156) 173 Example 1-3 Compound 33.93 16.9 (0.136, 0.156) 177 Example 1-4 Compound 43.72 17.6 (0.137, 0.157) 195 Example 1-5 Compound 53.85 17.1 (0.136, 0.156) 175 Example 1-6 Compound 63.84 17.4 (0.136, 0.157) 178 Example 1-7 Compound 73.7317.5(0.137, 0.156)192Example 1-8Compound 83.7517.3(0.137, 0.156)190Comparative Example 1-1C13.9815.7(0.137, 0.156)125Comparative Example 1-2C24.0215.4(0.134, 0.158)118Comparative Example 1-3C34.0415.9(0.136, 0.156)141Comparative Example 1-4C44.1315.2(0.134, 0.158)102Comparative Example 1-5C54.0615.7(0.136, 0.156)132Comparative Example 1-6C64.0815.8(0.137, 0.156)106

[0404] As shown in Table 1 above, the organic light-emitting devices of Examples 1-1 to 1-8, which use the compound of Chemical Formula 1 of the present specification, in which a carbazole group is bonded to a specific position of biscarbazole through a phenylene group, and the deuterium substitution rate of the biscarbazole compound is 90% or more, and a phenyl group is substituted in the biscarbazole, as a p-type host of the light-emitting layer, exhibited excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light-emitting device. Specifically, it can be seen that the organic light-emitting devices of Examples 1-1 to 1-8 of the present specification are superior in efficiency, driving voltage, and lifespan (stability) due to the following structural features compared to Comparative Examples 1-1 and 1-6 using compounds in which deuterium is not substituted, Comparative Examples 1-3 and 1-5 using compounds in which the deuterium substitution rate of biscarbazole is less than 90%, and Comparative Examples 1-2 and 1-4 using compounds in which the phenyl group is not substituted in the biscarbazole.

[0405] The above chemical formula 1 can prevent a host-guest electrostatic bonding state of an organic layer of an organic light-emitting device including the same by increasing the LUMO energy level of the compound including the biscarbazole structure. In addition, the phenyl group bonded to a specific position of the biscarbazole and the carbazole group bonded to a specific position of the biscarbazole through a phenylene group have a structural feature that participates in the conjugation system through a hyperconjugation effect to stabilize the excited and polaronic states of the above chemical formula 1. Therefore, the above chemical formula 1 can be included in the organic layer of the organic light-emitting device to improve efficiency, lower operating voltage, and improve lifespan characteristics.

[0406] In addition, the chemical formula 1 Since the deuterium substitution rate is more than 90%, the energy of the ground state is lowered, and as the bond length of deuterium and carbon is shortened, the molecular hardcore volume is reduced, and accordingly, the electrical polarizability can be reduced, and by weakening the intermolecular interaction, the thin film volume can be increased. In addition, these characteristics can have the effect of lowering the crystallinity of the thin film, that is, creating an amorphous state, and are effective in increasing the lifespan and operating characteristics of organic light-emitting devices.

[0407] Although the preferred embodiment of the present invention (BH p-type of the light-emitting layer) has been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention, and this also falls within the scope of the invention.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, m and n are 0 or 1, respectively, m+n is 1, D is deuterium, x1, x3, x4 and x7 are integers from 0 to 4, respectively. x2 is an integer from 0 to 3, x5 and x6 are integers from 0 to 5, respectively. x8 is an integer from 0 to 8, In the above chemical formula 1 The deuterium substitution rate is over 90%, * is a site that is bonded to the above chemical formula 1.

2. In claim 1, the chemical formula 1 is a compound having the following chemical formula 1-1 or 1-2: [Chemical Formula 1-1] [Chemical Formula 1-2] In the above chemical formulas 1-1 and 1-2, The definitions of D and x1 to x8 are the same as those defined in the above chemical formula 1.

3. In claim 1, the compound wherein the chemical formula 1 is any one of the following chemical formulas 2 to 4: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] In the above chemical formulas 2 to 4, The definitions of m, n, D and x1 to x8 are the same as those defined in the chemical formula 1 above.

4. In claim 1, the compound wherein the chemical formula 1 is any one of the following chemical formulas 2-1 to 2-8: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] [Chemical Formula 2-5] [Chemical Formula 2-6] [Chemical Formula 2-7] [Chemical Formula 2-8] In the above chemical formulas 2-1 to 2-8, The definitions of D and x1 to x8 are the same as those defined in the above chemical formula 1.

5. In claim 1, the compound wherein the chemical formula 1 is any one of the following chemical formulas 3-1 to 3-8: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] [Chemical Formula 3-5] [Hwahwasik 3-6] [Chemical Formula 3-7] [Chemical Formula 3-8] In the above chemical formulas 3-1 to 3-8, The definitions of D and x1 to x8 are the same as those defined in the above chemical formula 1.

6. In claim 1, the compound wherein the chemical formula 1 is any one of the following chemical formulas 4-1 to 4-8: [Chemical Formula 4-1] [Chemical Formula 4-2] [Chemical Formula 4-3] [Chemical Formula 4-4] [Chemical Formula 4-5] [Chemical Formula 4-6] [Chemical Formula 4-7] [Chemical Formula 4-8] In the above chemical formulas 4-1 to 4-8, The definitions of D and x1 to x8 are the same as those defined in the above chemical formula 1.

7. In claim 1, the chemical formula 1 A compound having a deuterium substitution rate of 90% to 93.33%.

8. A compound according to claim 1, wherein the deuterium substitution rate of the chemical formula 1 is 43.5% to 100%.

9. In claim 1, the compound having chemical formula 1 is any one of the following compounds: In the above compound, Dn is the number of deuterium atoms substituted in the compound in parentheses, The above Dn is an integer from 14 to 31, The deuterium substitution rates of the above compounds are 45.1% to 100%, respectively.

10. An organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 9.

11. An organic light-emitting device according to claim 10, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

12. An organic light-emitting device according to claim 10, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host for the light-emitting layer.

13. An organic light-emitting device according to claim 11, wherein the light-emitting layer comprises a dopant, and the dopant comprises a phosphorescent dopant.

14. An organic light-emitting device according to claim 11, wherein the light-emitting layer is a blue light-emitting layer.

15. An organic light-emitting device according to claim 10, 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.

16. An organic light-emitting device according to claim 10, wherein the organic layer includes an electron-blocking layer, and the electron-blocking layer includes the compound.

Images