Compound and organic light-emitting device containing the same

Abstract

This specification relates to a compound of Chemical Formula 1 and an organic light-emitting device comprising the same. The compound of Chemical Formula 1 can be used as a material for an organic layer of an organic light-emitting device, and the organic light-emitting device using the compound can improve efficiency and lifespan characteristics.

Description

[0001] This application is a divisional application of the application with an application date of January 15, 2020, application number 202080002724.3, and invention name “Compounds and organic light-emitting devices containing the same” (PCT / KR2020 / 000736, national phase entry date November 12, 2020). Technical Field

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

[0003] This application claims the benefit of Korean Patent Application No. 10-2019-0009968 filed with the Korean Intellectual Property Office on January 25, 2019, the entire contents of which are incorporated herein by reference. Background Art

[0004] An organic light-emitting device is a light-emitting device that utilizes organic semiconductor materials and requires the exchange of holes and / or electrons between electrodes and organic semiconductor materials. Organic light-emitting devices can be roughly divided into the following two types according to their working principles. The first type is a light-emitting device that utilizes photons flowing into the device from an external light source to form excitons in the organic layer. The excitons are separated into electrons and holes, which are then transferred to different electrodes and used as current sources (voltage sources). The second type is a light-emitting device that applies voltage or current to two or more electrodes, thereby injecting holes and / or electrons into the organic semiconductor material layer that forms an interface with the electrodes, and operates through the injected electrons and holes.

[0005] Generally speaking, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic light-emitting devices that utilize the organic light-emitting phenomenon generally have a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light-emitting device, the organic layer is mostly formed by a multilayer structure composed of different substances, for example, it can be formed by a hole injection layer, a hole transport layer, a light-emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer, etc. For the structure of such an organic light-emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons transition back to the ground state, light is emitted. Such organic light-emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

[0006] Materials used as organic layers in organic light-emitting devices can be divided into luminescent materials and charge transport materials based on their functions, such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, and electron injection materials. Based on the color of light emitted, luminescent materials include blue, green, and red luminescent materials, as well as yellow and orange luminescent materials required to achieve better natural colors.

[0007] Furthermore, to increase color purity and enhance luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material. The principle is that when a small amount of a dopant with a smaller energy band gap and superior luminous efficiency than the host, which primarily constitutes the luminescent layer, is mixed into the luminescent layer, excitons generated in the host are transferred to the dopant, resulting in highly efficient light emission. This shifts the wavelength of the host to that of the dopant, allowing light of a desired wavelength to be obtained depending on the type of dopant used.

[0008] In order to fully utilize the excellent characteristics of the above-mentioned organic light-emitting devices, the substances that constitute the organic layer in the device, such as hole injection substances, hole transport substances, luminescent substances, electron suppression substances, electron transport substances, electron injection substances, etc., are backed by stable and effective materials, and therefore there is a continuous demand for the development of new materials. Summary of the Invention

[0009] Technical issues

[0010] This specification describes a compound and an organic light-emitting device including the same.

[0011] Solution to the problem

[0012] One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[0013] [Chemical Formula 1]

[0014]

[0015] In the above Chemical Formula 1,

[0016] Ar is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0017] R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0018] r1 is an integer from 0 to 6,

[0019] r2 to r4 are each an integer from 0 to 4,

[0020] r5 is an integer from 0 to 2,

[0021] When r1 to r5 are 2 or more, the structures in the brackets are the same or different from each other.

[0022] n and m are each 0 or 1,

[0023] n+m=1,

[0024] When n is 1, X1 is a direct bond,

[0025] When m is 1, X2 is a direct bond.

[0026] Another embodiment provides an organic light-emitting device, comprising: a first electrode, a second electrode opposite to the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein one or more of the organic layers contains the above-mentioned compound.

[0027] Effects of the Invention

[0028] The compound represented by Chemical Formula 1 of the present invention may be used as a material for an organic layer of an organic light-emitting device.

[0029] An organic light emitting device including the compound represented by Chemical Formula 1 according to one embodiment of the present specification can improve efficiency.

[0030] An organic light emitting device including the compound represented by Chemical Formula 1 according to one embodiment of the present specification can improve lifespan characteristics. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] Figure 1 An organic light-emitting device according to one embodiment of the present specification is illustrated.

[0032] Figure 2 An organic light emitting device according to another embodiment of the present specification is illustrated.

[0033] Figure 3 An organic light emitting device according to another embodiment of the present specification is illustrated.

[0034] [Explanation of symbols]

[0035] 1: Substrate

[0036] 2: Anode

[0037] 3: Luminous layer

[0038] 4: cathode

[0039] 5: Hole injection layer

[0040] 6: Hole transport layer

[0041] 7: Luminous layer

[0042] 8: Electron transport layer

[0043] 9: Electron blocking layer

[0044] 10: Electron transport and injection layer DETAILED DESCRIPTION

[0045] Next, this specification is described in detail.

[0046] This specification provides the compound represented by the above Chemical Formula 1.

[0047] An organic light emitting device including the compound represented by Chemical Formula 1 according to one embodiment of the present specification can improve efficiency.

[0048] An organic light emitting device including the compound represented by Chemical Formula 1 according to one embodiment of the present specification can improve lifespan characteristics.

[0049] The compound represented by Chemical Formula 1 of the present invention is composed of a quinoxaline unit that functions as an electron acceptor and a benzindolecarbazole unit that functions as an electron donor. Since the two units with completely different properties are directly bonded, charges are exchanged within the molecule, thereby reducing the band gap.

[0050] Furthermore, the benzindolecarbazole unit contains a naphthalene ring, which reduces triplet energy. As a result, both singlet energy and triplet energy are small, which facilitates energy transfer to a red dopant and makes it suitable as a host for a red light-emitting layer.

[0051] In particular, the placement of the triplet-stabilizing naphthalene ring next to the nitrogen atom bound to quinoxaline further stabilizes internal charge transfer between quinoxaline and the benzindolecarbazole unit. Furthermore, the two nitrogen atoms within the benzindolecarbazole unit are positioned para to each other, maximizing the electron-pushing effect. This results in a higher HOMO (Highest Occupied Molecular Orbital) energy level, preventing hole capture by dopants and resulting in superior hole-transporting properties.

[0052] In addition, based on the quinoxaline unit, the Ar unit and the fused ring carbazole unit are substituted at the ortho position, facing each other due to structural hindrance, and the structure is further stabilized by the π-π interaction between them, thereby exhibiting long-life characteristics.

[0053] In this specification, when it is stated that a part "includes / comprising" a certain component, unless otherwise stated, it means that other components may be further included, rather than excluding other components.

[0054] In this specification, when it is stated that a certain member is located “on” another member, it not only includes a case where the certain member is in contact with the other member, but also includes a case where other members exist between the two members.

[0055] In this specification, examples of substituents are described below, but the substituents are not limited thereto.

[0056] The term "substituted" as used above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent. The position to be substituted is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are two or more substitutions, the two or more substituents may be the same or different from each other.

[0057] In this specification, the term "substituted or unsubstituted" refers to a group that is substituted with one or more substituents selected from deuterium (-D), a halogen group, a nitrile group, a nitro group, a hydroxyl group, a silyl group, a boron group, an alkoxy group, an alkyl group, a cycloalkyl group, an aryl group, and a heterocyclic group, or is substituted with a substituent consisting of two or more of the above-mentioned substituents linked together, or is unsubstituted. For example, a "substituent consisting of two or more substituents linked together" can be a biphenyl group. That is, a biphenyl group can be an aryl group, or it can be interpreted as a substituent consisting of two phenyl groups linked together.

[0058] In the present specification, examples of the halogen group include fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).

[0059] In this specification, a silyl group can be represented by the chemical formula -SiYaYbYc, where Ya, Yb, and Yc can each be hydrogen, deuterium, a halogen, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. Specific examples of the silyl group include, but are not limited to, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.

[0060] In this specification, a boryl group can be represented by the chemical formula -BYdYe, where Yd and Ye can each be oxygen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. Specific examples of the boryl group include, but are not limited to, trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl.

[0061] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, and n-octyl.

[0062] 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 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-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2-diphenylethen-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethen-1-yl, 2,2-bis(diphenyl-1-yl)ethen-1-yl, stilbene, and styryl, but are not limited thereto.

[0063] In this specification, the alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but preferably has a carbon number of 1 to 20. Specifically, it may be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, an isopropyloxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentoxy group, a n-hexyloxy group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, a n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, etc., but is not limited thereto.

[0064] The alkyl group, alkoxy group, and substituents containing an alkyl moiety other than these groups described in this specification include all of linear and branched forms.

[0065] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups.

[0066] In this specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 20. According to one embodiment, the carbon number of the aryl group is 6 to 30. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, quaterphenyl, etc., but is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, phenylene, fluorenyl, triphenylene, etc., but are not limited thereto.

[0067] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

[0068] In the case where the above fluorenyl group is substituted, it can be Isospirofluorenyl; (9,9-dimethylfluorenyl), and (9,9-diphenylfluorenyl) and other substituted fluorenyl groups, but are not limited thereto.

[0069] In the present specification, a heterocyclic group is a ring group containing one or more of N, O, P, S, Si, and Se as heteroatoms. The number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 20. Examples of the heterocyclic group include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, indenocarbazolyl, and indolocarbazolyl.

[0070] In the present specification, a heteroaryl group is aromatic, and other than this, the above description of the heterocyclic group is applicable.

[0071] According to one embodiment of the present specification, the above Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2 to 7.

[0072] [Chemical Formula 2]

[0073]

[0074] [Chemical Formula 3]

[0075]

[0076] [Chemical Formula 4]

[0077]

[0078] [Chemical Formula 5]

[0079]

[0080] [Chemical Formula 6]

[0081]

[0082] [Chemical Formula 7]

[0083]

[0084] In the above Chemical Formulas 2 to 7,

[0085] Ar, R1 to R5, and r1 to r5 are the same as defined in Chemical Formula 1.

[0086] According to one embodiment of the present specification, Ar is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0087] According to one embodiment of the present specification, Ar is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

[0088] According to one embodiment of the present specification, Ar is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0089] According to one embodiment of the present specification, Ar is a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothienyl group; or a substituted or unsubstituted bicyclic heterocyclic group containing N, O or S.

[0090] According to one embodiment of the present specification, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzothiophene group, or a substituted or unsubstituted benzothiophene group. oxazolyl, or substituted or unsubstituted benzothiazolyl.

[0091] According to one embodiment of the present specification, Ar is a phenyl group substituted or unsubstituted by an alkyl or aryl group, a naphthyl group substituted or unsubstituted by an alkyl or aryl group, a biphenyl group substituted or unsubstituted by an alkyl or aryl group, a terphenyl group substituted or unsubstituted by an alkyl or aryl group, a carbazolyl group substituted or unsubstituted by an alkyl or aryl group, a fluorenyl group substituted or unsubstituted by an alkyl or aryl group, a dibenzofuranyl group substituted or unsubstituted by an alkyl or aryl group, a dibenzothiophene group substituted or unsubstituted by an alkyl or aryl group, oxazolyl, or benzothiazolyl which may be substituted by an alkyl group or an aryl group.

[0092] According to one embodiment of the present specification, Ar is phenyl, naphthyl, biphenyl, terphenyl, carbazolyl substituted or unsubstituted by phenyl, fluorenyl substituted or unsubstituted by methyl, dibenzofuranyl, dibenzothiophenyl, or benzothiazolyl.

[0093] According to one embodiment of the present specification, Ar is a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a carbazolyl group which may be substituted with a phenyl group, a dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, or a benzothiazolyl group.

[0094] According to one embodiment of the present specification, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0095] According to one embodiment of the present specification, Ar is a phenyl group, a naphthyl group, a biphenyl group, a dimethylfluorenyl group, a carbazolyl group which may be substituted with a phenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

[0096] According to one embodiment of the present specification, Ar is a phenyl group, a naphthyl group, a biphenyl group, a dimethylfluorenyl group, a carbazolyl group, or a dibenzofuranyl group.

[0097] According to one embodiment of the present specification, Ar can be represented by any of the following structures.

[0098]

[0099] In the above structure,

[0100] B1 to B13 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

[0101] b1 is an integer from 0 to 5,

[0102] b2 is an integer from 0 to 9,

[0103] b3 is an integer from 0 to 13,

[0104] b4 to b7 are each an integer from 0 to 7,

[0105] b8 is an integer from 0 to 8,

[0106] b9 is an integer from 0 to 4,

[0107] b10 is an integer from 0 to 7,

[0108] When b1 to b10 are 2 or more, the structures in the two or more brackets are the same as or different from each other.

[0109] According to one embodiment of the present specification, Ar can be represented by any of the following structures.

[0110]

[0111] In the above structures, the dotted lines indicate the binding sites.

[0112] According to one embodiment of the present specification, Ar can be represented by any of the following structures.

[0113]

[0114] In the above structures, the dotted lines indicate the binding sites.

[0115] According to one embodiment of the present specification, B1 to B10 are hydrogen.

[0116] According to one embodiment of the present specification, B11 to B13 are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0117] According to one embodiment of the present specification, B11 to B13 are each independently a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0118] According to one embodiment of the present specification, B11 to B13 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0119] According to one embodiment of the present specification, B11 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0120] According to one embodiment of the present specification, B11 is a substituted or unsubstituted phenyl group.

[0121] According to one embodiment of the present specification, B11 is a phenyl group.

[0122] According to one embodiment of the present specification, B12 and B13 are each independently a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms.

[0123] According to one embodiment of the present specification, B12 and B13 are methyl groups.

[0124] According to one embodiment of the present specification, b1 to b10 are 0 or 1.

[0125] According to one embodiment of the present specification, b1 to b10 are 0.

[0126] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or can be combined with adjacent groups to form a substituted or unsubstituted ring.

[0127] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms.

[0128] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.

[0129] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group, or are combined with adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.

[0130] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group, or are combined with adjacent groups to form a substituted or unsubstituted benzene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indene ring.

[0131] According to one embodiment of the present specification, R1 to R5 are the same or different and are independently hydrogen, deuterium, or phenyl, or are combined with adjacent groups to form a benzene ring, a benzofuran ring, a benzothiophene ring, or an indene ring which may be substituted or unsubstituted with a methyl group.

[0132] According to one embodiment of the present specification, R1 to R5 are hydrogen.

[0133] According to one embodiment of the present specification, R1, R4 and R5 are hydrogen.

[0134] According to one embodiment of the present specification, R2 and R3 are hydrogen, deuterium, or phenyl, or multiple R2 or multiple R3 are combined to form a benzene ring, a benzofuran ring, a benzothiophene ring, or an indene ring substituted with a methyl group.

[0135] According to one embodiment of the present specification, R2 and R3 are hydrogen, deuterium, or phenyl, or multiple R2 or multiple R3 are combined to form a benzene ring, a benzofuran ring, a benzothiophene ring, or an indene ring substituted with a methyl group.

[0136] According to one embodiment of the present specification, R1 to R5 may be combined with adjacent groups to form a substituted or unsubstituted ring.

[0137] In this specification, "adjacent" groups may refer to substituents substituted on an atom directly connected to the atom substituted by the substituent, the substituent closest to the substituent in terms of steric structure, or other substituents substituted on 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 in an aliphatic ring can be interpreted as "adjacent" groups to each other.

[0138] In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, the term "ring" means a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0139] The hydrocarbon ring may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic groups, and may be selected from the examples of the cycloalkyl or aryl groups described above, except for the aforementioned divalent groups. Specifically, the aromatic hydrocarbon ring, except for the divalent group, is subject to the above description of the aryl group, and the aliphatic hydrocarbon ring, except for the divalent group, is subject to the above description of the cycloalkyl group.

[0140] The above description of the heterocyclic group is applicable to the above heterocyclic group except that the heterocyclic group is divalent.

[0141] According to one embodiment of the present specification, multiple R1s, multiple R2s, multiple R3s, or multiple R4s may be bonded to each other to independently form a substituted or unsubstituted ring, and R2 and R3 may be bonded to each other to form a substituted or unsubstituted ring.

[0142] According to one embodiment of the present specification, when R1 to R5 are each independently bonded to an adjacent group to form a substituted or unsubstituted ring, they may form any of the following structures.

[0143]

[0144] In the above structure,

[0145] A1 to A24 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0146] a1 to a11 are each an integer from 0 to 4,

[0147] a12 is an integer from 0 to 6,

[0148] * indicates the position of substitution.

[0149] According to one embodiment of the present specification, A1 to A12 are hydrogen.

[0150] According to one embodiment of the present specification, A13 to A24 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0151] According to one embodiment of the present specification, A20 and A21 are each independently a substituted or unsubstituted alkyl group.

[0152] According to one embodiment of the present specification, A20 and A21 are methyl groups.

[0153] According to one embodiment of the present specification, r1 is an integer from 0 to 6.

[0154] According to one embodiment of the present specification, r1 is an integer from 0 to 1.

[0155] According to one embodiment of the present specification, r2 to r4 are each an integer from 0 to 4.

[0156] According to one embodiment of the present specification, r2 to r4 are each an integer from 0 to 1.

[0157] According to one embodiment of the present specification, r5 is an integer from 0 to 2.

[0158] According to one embodiment of the present specification, r5 is an integer from 0 to 1.

[0159] According to one embodiment of the present specification, a plurality of R2s or a plurality of R3s may be bonded to each other or to each other to independently form a substituted or unsubstituted ring.

[0160] According to one embodiment of the present specification, a plurality of R2s or a plurality of R3s may be bonded to each other or to each R3 to independently form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0161] According to one embodiment of the present specification, a plurality of R2s or a plurality of R3s may be bonded to each other to independently form a ring in any of the following structures: In the following structures, A1 to A4, A20, A21 and a1 to a4 are the same as defined above.

[0162]

[0163] According to one embodiment of the present specification, R2 and R3 are hydrogen, deuterium, or phenyl, or Multiple R2 or A plurality of R3's in the formula (a) are combined with each other to form any of the following structures.

[0164]

[0165] In the above structure, Indicates the position where N is bound.

[0166] According to one embodiment of the present specification, R2 and R3 are hydrogen, deuterium, or phenyl, or Multiple R2 or A plurality of R3's in the formula (a) are combined with each other to form any of the following structures.

[0167]

[0168] In the above structure, Indicates the position where N is bound.

[0169] According to one embodiment of the present specification, R2 and R3 are hydrogen, deuterium, or phenyl, or a plurality of R2 or a plurality of R3 are combined to form a naphthalene, dibenzofuran, or dibenzothiophene ring.

[0170] According to one embodiment of the present specification, R2 and R3 are hydrogen, or a plurality of R2 or a plurality of R3 are bonded to form a naphthalene or dibenzofuran ring.

[0171] According to one embodiment of the present specification, n and m are each 0 or 1, n + m = 1, when n is 1, X1 is a direct bond, when m is 1, X2 is a direct bond.

[0172] According to one embodiment of the present specification, when n is 0, X1 does not exist because it is not bound.

[0173] According to one embodiment of the present specification, when m is 0, X2 does not exist because it is not bound.

[0174] According to one embodiment of the present specification, the above Chemical Formula 1 may be represented by any one of the following compounds.

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182] The compound represented by Chemical Formula 1 of the present specification can be used to prepare a core structure as shown in the following reaction formula: Substituents can be bonded by methods known in the art, and the type, position, and number of substituents can be varied according to techniques known in the art.

[0183] <Reaction formula>

[0184]

[0185] In the above reaction formula, Ar, X1, X2, R1 to R5, r1 to r5, m and n are the same as defined in Chemical Formula 1, and each X is independently a halogen group.

[0186] In this specification, by introducing a variety of substituents into the core structure as described above, compounds with a variety of band gaps can be synthesized. In addition, in this specification, by introducing a variety of substituents into the core structure of the structure described above, the HOMO and LUMO energy levels of the compound can also be adjusted.

[0187] In addition, the organic light-emitting device according to the present specification is characterized in that it includes: a first electrode, a second electrode opposite to the above-mentioned first electrode, and one or more organic layers between the above-mentioned first electrode and the above-mentioned second electrode, and one or more of the above-mentioned organic layers contains the above-mentioned compound.

[0188] The organic light-emitting device of the present specification uses the compound represented by the above Chemical Formula 1 to form one or more organic layers, and can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0189] When manufacturing an organic light-emitting device having an organic layer containing the compound represented by Compound 1, the organic layer can be formed not only by vacuum deposition but also by solution coating. The solution coating method herein includes, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, and roller coating.

[0190] The organic layer of the organic light-emitting device of the present specification may be formed of a single layer structure or a multilayer structure comprising two or more organic layers stacked on top of each other. For example, the organic light-emitting device of the present invention may have a structure comprising one or more of a hole transport layer, a hole injection layer, an electron blocking layer, a layer that simultaneously performs hole transport and hole injection, an electron transport layer, an electron injection layer, a hole blocking layer, and a layer that simultaneously performs electron transport and electron injection as the organic layer. However, the structure of the organic light-emitting device of the present specification is not limited to this and may include a fewer or greater number of organic layers.

[0191] In the organic light-emitting device of the present disclosure, the organic layer includes a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include the compound represented by Chemical Formula 1.

[0192] In another organic light-emitting device of the present disclosure, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by Chemical Formula 1.

[0193] In another organic light-emitting device of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include the compound represented by the above Chemical Formula 1.

[0194] According to another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer may contain the compound as a host of the light-emitting layer.

[0195] In one embodiment of the present specification, the light-emitting layer includes the compound represented by Chemical Formula 1 as a host, and may further include a dopant. In this case, the content of the dopant may be 1 to 60 parts by weight, preferably 1 to 20 parts by weight, and more preferably 1 to 10 parts by weight, based on 100 parts by weight of the host.

[0196] At this time, as the above-mentioned dopant, phosphorescent substances such as (4,6-F2ppy)2Irpic, or fluorescent substances such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers, PPV-based polymers, anthracene-based compounds, pyrene-based compounds, and boron-based compounds can be used, but are not limited to these.

[0197] In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

[0198] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0199] For example, the organic light emitting device may have a stacked structure as described below, but is not limited thereto.

[0200] (1) Anode / HTL / Emitting Layer / Cathode

[0201] (2) Anode / HOL injection layer / HOL transport layer / Emitting layer / Cathode

[0202] (3) Anode / HTL / Luminescent Layer / Electron Transport Layer / Cathode

[0203] (4) Anode / HTL / Luminescent Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0204] (5) Anode / HOL injection layer / HOL transport layer / Luminescent layer / Electron transport layer / Cathode

[0205] (6) Anode / Hole Injection Layer / Hole Transport Layer / Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0206] (7) Anode / HTL / Electron Blocking Layer / Emitting Layer / Electron Transport Layer / Cathode

[0207] (8) Anode / HTL / Electron Blocking Layer / Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0208] (9) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Emitting Layer / Electron Transport Layer / Cathode

[0209] (10) Anode / HOL injection layer / HOL transport layer / Electron blocking layer / Emission layer / Electron transport layer / Electron injection layer / Cathode

[0210] (11) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0211] (12) Anode / HTL / Emitting Layer / HTL / Electron Transport Layer / Electron Injection Layer / Cathode

[0212] (13) Anode / Hole Injection Layer / Hole Transport Layer / Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Cathode

[0213] (14) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0214] The structure of the organic light emitting device of the present specification may have the following Figures 1 to 3 The structure shown is not limited to this.

[0215] Figure 1 exemplifies the structure of an organic light-emitting device in which an anode 2, a light-emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In the above structure, the compound may be contained in the light-emitting layer 3.

[0216] Figure 2 exemplifies the structure of an organic light-emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1. In the above structure, the compound may be contained in the light-emitting layer 7.

[0217] Figure 3 , there is shown an example of an organic light-emitting device structure in which an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 9, a light-emitting layer 7, an electron transport and injection layer 10, and a cathode 4 are sequentially stacked on a substrate 1. In the above structure, the compound may be contained in the light-emitting layer 7.

[0218] For example, an organic light-emitting device according to the present specification can be manufactured by depositing a metal, a conductive metal oxide, or an alloy thereof onto a substrate using a PVD (physical vapor deposition) method 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, an electron blocking layer, an electron transport layer, and an electron injection layer is then formed on the anode. A cathode material is then deposited on the organic layer. Alternatively, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto a substrate.

[0219] The organic layer may have a multilayer structure including, but is not limited to, a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport, an electron blocking layer, a light-emitting layer and an electron transport layer, an electron injection layer, and a layer that simultaneously performs electron injection and electron transport. Furthermore, the organic layer may be manufactured into a smaller number of layers using various polymer materials and solvent processes other than vapor deposition, such as spin coating, dip coating, doctor blade coating, screen printing, inkjet printing, or thermal transfer.

[0220] The anode is an electrode that injects holes. Anode materials are generally preferably materials with a large work function to facilitate hole injection into the organic layer. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, aluminum 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, but are not limited thereto.

[0221] The cathode is an electrode that injects electrons. Generally, cathode materials with a low work function are preferred to facilitate electron injection into the organic layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, steel, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0222] The hole injection layer is a layer that plays a role in smoothly injecting holes from the anode into the light-emitting layer. The hole injection material is a material that can well inject holes from the anode at low voltage. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrins (porphyrine), oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinone and polyaniline and polythiophene conductive polymers, but are not limited thereto. The thickness of the hole injection layer can be 1 to 150nm. When the thickness of the hole injection layer is more than 1nm, there is an advantage that the hole injection characteristics can be prevented from decreasing. When it is less than 150nm, there is an advantage that the driving voltage can be increased when the thickness of the hole injection layer is too thick in order to increase the movement of holes.

[0223] The hole transport layer facilitates hole transport. Hole transport materials are substances that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer. Suitable materials have high hole mobility. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions.

[0224] An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may be made of a material known in the art.

[0225] The light-emitting layer can emit red, green or blue light and can be composed of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo azole, benzothiazole and benzimidazole compounds; poly(p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited thereto.

[0226] The light-emitting layer may include the compound represented by Chemical Formula 1 of the present application, and specifically, may include the compound represented by Chemical Formula 1 of the present application as a host. Specifically, when the compound represented by Chemical Formula 1 of the present application is used as a host of the light-emitting layer, it can be used as a phosphorescent substance that emits red light.

[0227] When the light-emitting layer emits red light, as a light-emitting dopant, phosphorescent substances such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium, bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium, bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium, tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or fluorescent substances such as Alq3(tris(8-hydroxyquinolino)aluminum, tris(8-hydroxyquinolino)aluminum) can be used, but are not limited to these.

[0228] The light-emitting layer may further include a compound represented by the following Chemical Formula 8. Specifically, the light-emitting layer may include the compound represented by the following Chemical Formula 8 as an additional host. In this case, the compound represented by Chemical Formula 1 may include 10 to 70 parts by weight, preferably 20 to 50 parts by weight, based on 100 parts by weight of the total host.

[0229] [Chemical Formula 8]

[0230]

[0231] In the above chemical formula 8,

[0232] R a and R b are the same as or different from each other and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0233] R c and R dare the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; an amino group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms and containing any one or more selected from N, O and S,

[0234] r and s are each an integer from 0 to 7. When r is 2 or greater, R c are the same or different from each other, and when s is 2 or more, R d the same as or different from each other.

[0235] According to one embodiment of this specification, R c and R d The same as or different from each other, each independently represents hydrogen; deuterium; a halogen group; a cyano group; a nitro group; an amino group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a heteroaryl group having 2 to 30 carbon atoms containing any one or more selected from substituted or unsubstituted N, O and S.

[0236] According to one embodiment of this specification, R c and R d For hydrogen.

[0237] According to one embodiment of this specification, R a and R b They are the same as or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0238] According to one embodiment of this specification, R a and R b They are the same as or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0239] According to one embodiment of this specification, R a and R b The same as or different from each other, each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted benzothiazolyl group.

[0240] According to one embodiment of this specification, R a and R b The same as or different from each other, and each independently represents a phenyl group which may be substituted by an alkyl group or an aryl group, a biphenyl group which may be substituted by an alkyl group or an aryl group, a terphenyl group which may be substituted by an alkyl group or an aryl group, a naphthyl group which may be substituted by an alkyl group or an aryl group, a fluorenyl group which may be substituted by an alkyl group or an aryl group, a dibenzofuranyl group which may be substituted by an alkyl group or an aryl group, or a dibenzothiophenyl group which may be substituted by an alkyl group or an aryl group.

[0241] According to one embodiment of this specification, R a and R b are the same as or different from each other and are each independently a phenyl group substituted or unsubstituted by a methyl group, a phenyl group or a naphthyl group; a biphenyl group substituted or unsubstituted by a methyl group, a phenyl group or a naphthyl group; a terphenyl group substituted or unsubstituted by a methyl group, a phenyl group or a naphthyl group; a naphthyl group substituted or unsubstituted by a methyl group, a phenyl group or a naphthyl group; a fluorenyl group substituted or unsubstituted by a methyl group, a phenyl group or a naphthyl group; a dibenzofuranyl group substituted or unsubstituted by a methyl group, a phenyl group or a naphthyl group; or a dibenzothienyl group substituted or unsubstituted by a methyl group, a phenyl group or a naphthyl group. According to one embodiment of the present specification, R a and R b The same as or different from each other, and each independently represents a phenyl group which may be substituted by a phenyl group or a naphthyl group, a biphenyl group, a terphenyl group, a naphthyl group which may be substituted by a phenyl group, a dimethylfluorenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

[0242] According to one embodiment of this specification, R a and R b Each can be represented by any of the following structures.

[0243]

[0244] In the above structure,

[0245] C1 to C13 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

[0246] c1 is an integer from 0 to 5,

[0247] c2 is an integer from 0 to 9,

[0248] c3 is an integer from 0 to 13,

[0249] c4 to c7 are each an integer from 0 to 7,

[0250] c8 is an integer from 0 to 8,

[0251] c9 is an integer from 0 to 4,

[0252] c10 is an integer from 0 to 7,

[0253] When c1 to c10 are 2 or more, the structures in the two or more brackets are the same as or different from each other.

[0254] According to one embodiment of the present specification, C1 to C10 are hydrogen.

[0255] According to one embodiment of the present specification, C11 to C13 are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0256] According to one embodiment of the present specification, C11 to C13 are each independently a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0257] According to one embodiment of the present specification, C11 to C13 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0258] According to one embodiment of the present specification, C11 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0259] According to one embodiment of the present specification, C11 is a substituted or unsubstituted phenyl group.

[0260] According to one embodiment of the present specification, C11 is a phenyl group.

[0261] According to one embodiment of the present specification, C12 and C13 are each independently a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms.

[0262] According to one embodiment of the present specification, C12 and C13 are methyl groups.

[0263] According to one embodiment of this specification, R a and R b Each can be represented by any of the following structures.

[0264]

[0265] The definitions of C1 to C3, C5 to C7, C10, C12, C13, c1 to c3, c5 to c7 and c10 are the same as those described above.

[0266] According to one embodiment of the present specification, r and s are each an integer from 0 to 7.

[0267] According to one embodiment of the present specification, r and s are each 0 or 1.

[0268] According to one embodiment of the present specification, the above Chemical Formula 8 may be represented by any one of the following compounds.

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275] The above-mentioned electron transport layer can play a role in making the transmission of electrons smooth. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, and a material with a large electron mobility is suitable. As a specific example, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to these. The thickness of the electron transport layer can be 1 to 50 nm. When the thickness of the electron transport layer is 1 nm or more, it has the advantage of preventing the hole transport characteristics from decreasing. When it is 50 nm or less, it has the advantage of preventing the driving voltage from increasing in order to increase the mobility of electrons when the thickness of the electron transport layer is too thick.

[0276] The electron injection layer can play a role in facilitating the injection of electrons. As the electron injection material, the following compounds are preferred: compounds that have the ability to transport electrons, have the effect of injecting electrons from the cathode, have excellent electron injection effects on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer, and have excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dioxane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0277] Examples of the metal coordination compounds include, but are not limited to, 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)gallium chloride, bis(2-methyl-8-quinolinato)(o-cresol)gallium, bis(2-methyl-8-quinolinato)(1-naphthol)aluminum, and bis(2-methyl-8-quinolinato)(2-naphthol)gallium.

[0278] The hole blocking layer is a layer that prevents holes from reaching the cathode and can usually be formed under the same conditions as the hole injection layer. Examples include, but are not limited to, diazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0279] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type depending on the materials used.

[0280] Modes for Carrying Out the Invention

[0281] Below, to specifically illustrate this specification, examples are given for detailed description. However, the examples of this specification can be modified into various other forms, and the scope of this application is not to be construed as being limited to the examples detailed below. The examples of this application are provided to more fully illustrate this specification to those skilled in the art.

[0282] [Synthesis example]

[0283] [Production Example 1] Synthesis of Intermediate A

[0284] 1) Synthesis of Intermediate A-1

[0285]

[0286] In a three-necked flask, 2-bromo-9-phenyl-9H-carbazole (20.0 g, 62.1 mmol), bis(pinacolato)diboron (18.9 g, 74.5 mmol), Tris(dibenzylideneacetone)dipalladium(0) (Pd(dba)2) (0.7 g, 1.2 mmol), tricyclohexylphosphine (PCy3) (0.7 g, 2.5 mmol), potassium acetate (KOAc) (12.2 g, 124.1 mmol), 300 ml of 1,4-dichlorobenzene were added. After the reaction was complete, the mixture was cooled to room temperature and then transferred to a separatory funnel. Water (200 mL) was added and the mixture was extracted with ethyl acetate. The extract was dried over MgSO4, filtered, and concentrated. The sample was then purified by silica gel column chromatography to obtain Intermediate A-1 (17.2 g). (Yield 75%, MS: [M+H]) + =369)

[0287] 2) Synthesis of Intermediate A-2

[0288]

[0289] In a three-necked flask, Intermediate A-1 (17.0 g, 46.0 mmol) and 1-bromo-2-nitronaphthalene (12.8 g, 50.6 mmol) were dissolved in 255 ml of tetrahydrofuran (THF). Potassium carbonate (K2CO3) (25.5 g, 184.1 mmol) dissolved in 85 ml of H2O was added. Tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (2.7 g, 2.3 mmol) was added to the mixture, and the mixture was stirred under reflux under an argon atmosphere for 8 hours. Upon completion of the reaction, the mixture was cooled to room temperature, transferred to a separatory funnel, and extracted with ethyl acetate. The extract was dried over MgSO4, filtered, and concentrated, and the sample was purified by silica gel column chromatography to obtain intermediate A-2 (12.0 g). (Yield 63%, MS [M+H] +=414)

[0290] 3) Synthesis of Intermediate A

[0291]

[0292] In a two-necked flask, intermediate A-2 (12.0 g, 29.0 mmol), triphenylphosphine (PPh3) (6.0 g, 43.4 mmol), and 120 ml of o-dichlorobenzene (o-DCB) were added and stirred under reflux for 24 hours. After the reaction was completed, the mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure, and the mixture was extracted with CH2Cl2. The extract was dried over MgSO4, filtered, and concentrated. The sample was then purified by silica gel column chromatography to obtain intermediate A (8.9 g). (Yield 69%, MS [M+H] + =382)

[0293] [Production Example 2] Synthesis of Intermediate B

[0294]

[0295] Intermediate B was produced by the same production method as that of Intermediate A except that 2-bromo-3-nitronaphthalene was used instead of 1-bromo-2-nitronaphthalene in Production Example 1. (MS[M+H] + =382)

[0296] [Production Example 3] Synthesis of Intermediate C

[0297]

[0298] Intermediate C was produced by the same production method as that of Intermediate A except that 2-bromo-1-nitronaphthalene was used instead of 1-bromo-2-nitronaphthalene in Production Example 1. (MS[M+H] + =382)

[0299] [Production Example 4] Synthesis of Intermediate D

[0300]

[0301] Intermediate D was produced by the same production method as that of Intermediate A, except that 2-bromo-9-phenyl-9H-carbazole was used instead of 2-bromo-9-phenyl-9H-carbazole in Production Example 1. (MS [M+H] + =423)

[0302] [Production Example 5] Synthesis of Intermediate E

[0303]

[0304] Intermediate E was produced by the same production method as that of Intermediate A except that 4-bromo-9-phenyl-9H-carbazole was used instead of 2-bromo-9-phenyl-9H-carbazole in Production Example 1. (MS [M+H] + =382)

[0305] [Production Example 6] Synthesis of Intermediate F

[0306]

[0307] In Preparation Example 1, Intermediate F was prepared by the same method as that for Intermediate A, except that 4-bromo-9-phenyl-9H-carbazole was used instead of 2-bromo-9-phenyl-9H-carbazole, and 2-bromo-3-nitronaphthalene was used instead of 1-bromo-2-nitronaphthalene. (MS [M+H] + = 382)

[0308] [Production Example 7] Synthesis of Intermediate G

[0309]

[0310] In Preparation Example 1, Intermediate G was prepared by the same preparation method as that of Intermediate A, except that 4-bromo-9-phenyl-9H-carbazole was used instead of 2-bromo-9-phenyl-9H-carbazole and 2-bromo-1-nitronaphthalene was used instead of 1-bromo-2-nitronaphthalene. (MS [M+H] + =382)

[0311] [Production Example 8] Synthesis of Intermediate H

[0312]

[0313] In Preparation Example 1, Intermediate H was prepared by the same preparation method as that of Intermediate A, except that 2-bromo-9-phenyl-9H-carbazole was replaced with 4-bromo-9-(dibenzo[b,d]furan-3-yl)-9H-carbazole and 1-bromo-2-nitronaphthalene was replaced with 2-bromo-3-nitronaphthalene. (MS[M+H] + =472)

[0314] [Synthesis Example 1] Synthesis of Compound 1

[0315]

[0316] In a three-necked flask, intermediate A (10.0 g, 26.1 mmol) and intermediate a (6.9 g, 28.8 mmol) were dissolved in 300 ml of toluene, and sodium tert-butoxide (NaOtBu) (3.8 g, 39.2 mmol) and bis(tri-tert-butylphosphine)palladium(0) (Pd(P-tBu3)2) (0.3 g, 0.5 mmol) were added, followed by stirring under argon reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, H2O was added, and the reaction solution was transferred to a separatory funnel and extracted. The extract was dried over MgSO4 and concentrated. The sample was purified by silica gel column chromatography and then purified by sublimation to obtain 5.7 g of compound 1. (Yield 37%, MS [M+H] + =586)

[0317] [Synthesis Example 2] Synthesis of Compound 2

[0318]

[0319] In Synthesis Example 1, except that Intermediate a was replaced with Intermediate b, Compound 2 was produced by the same production method as that of Compound 1. (MS[M+H] + =636)

[0320] [Synthesis Example 3] Synthesis of Compound 3

[0321]

[0322] In Synthesis Example 1, except that Intermediate a was replaced with Intermediate c, Compound 3 was produced by the same production method as that of Compound 1. (MS[M+H] + =676)

[0323] [Synthesis Example 4] Synthesis of Compound 4

[0324]

[0325] In Synthesis Example 1, except that Intermediate A was replaced with Intermediate B, Compound 4 was produced by the same production method as that of Compound 1. (MS[M+H] + =586)

[0326] [Synthesis Example 5] Synthesis of Compound 5

[0327]

[0328] In Synthesis Example 1, except that Intermediate A was replaced by Intermediate B and Intermediate a was replaced by Intermediate d, Compound 5 was produced by the same production method as that of Compound 1. (MS[M+H] + =662)

[0329] [Synthesis Example 6] Synthesis of Compound 6

[0330]

[0331] In Synthesis Example 1, Compound 6 was produced by the same production method as that of Compound 1, except that Intermediate A was used instead of Intermediate C.

[0332] (MS[M+H] + =586)

[0333] [Synthesis Example 7] Synthesis of Compound 7

[0334]

[0335] In Synthesis Example 1, Compound 7 was produced by the same production method as that of Compound 1, except that Intermediate A was used instead of Intermediate D.

[0336] (MS[M+H] + =636)

[0337] [Synthesis Example 8] Synthesis of Compound 8

[0338]

[0339] In Synthesis Example 1, except that Intermediate A was replaced with Intermediate E, Compound 8 was produced by the same production method as that of Compound 1. (MS[M+H] + =586)

[0340] [Synthesis Example 9] Synthesis of Compound 9

[0341]

[0342] In Synthesis Example 1, except that Intermediate A was replaced by Intermediate E and Intermediate a was replaced by Intermediate e, Compound 9 was produced by the same production method as that of Compound 1. (MS[M+H] + =702)

[0343] [Synthesis Example 10] Synthesis of Compound 10

[0344]

[0345] In Synthesis Example 1, Compound 10 was produced by the same production method as that of Compound 1, except that Intermediate F was used instead of Intermediate A.

[0346] (MS[M+H] + =586)

[0347] [Synthesis Example 11] Synthesis of Compound 11

[0348]

[0349] In Synthesis Example 1, except that Intermediate A was replaced by Intermediate F and Intermediate a was replaced by Intermediate f, Compound 11 was produced by the same production method as that of Compound 1. (MS[M+H] + =675)

[0350] [Synthesis Example 12] Synthesis of Compound 12

[0351]

[0352] In Synthesis Example 1, Compound 12 was produced by the same production method as that of Compound 1, except that Intermediate A was used instead of Intermediate G.

[0353] (MS[M+H] + =586)

[0354] [Synthesis Example 13] Synthesis of Compound 13

[0355]

[0356] In Synthesis Example 1, Compound 13 was produced by the same production method as that of Compound 1, except that Intermediate H was used instead of Intermediate A.

[0357] (MS[M+H] + =676)

[0358] [Experimental example]

[0359] Comparative Example 1-1

[0360] ITO (Indium Tin Oxide) The thickness of the glass substrate coated with a film is placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent uses Fischer Co. products, and the distilled water uses distilled water filtered twice by a filter manufactured by Millipore Co. After the ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed and dried with a solvent of isopropyl alcohol, acetone, and methanol, and then the substrate is transported to a plasma cleaning machine. In addition, after the above-mentioned substrate is cleaned for 5 minutes, the substrate is transported to a vacuum deposition machine.

[0361] On the ITO transparent electrode prepared in this way, the following HI-A and hexaazatriphenylene (HAT-CN) were respectively The hole injection layer was formed by thermal vacuum deposition of the following thickness. After vacuum deposition of a thickness of 1000 nm, the following EB-A was applied as an electron blocking layer. Then, as the light-emitting layer, the following host RH-A and 2 wt% (based on 100 parts by weight of the host) of dopant RD were mixed to form a luminous layer. Then, as the electron transport and injection layer, the following ET-A and Liq were mixed in a ratio of 1:1. The thickness of the thermal vacuum evaporation was carried out, and then Liq was Vacuum evaporation is performed on the film to a thickness of 100 nm.

[0362]

[0363] On the electron transport and injection layer, magnesium and silver were sequentially added in a ratio of 10:1. The thickness of the aluminum A cathode is formed by evaporation with a thickness of , thereby manufacturing an organic light-emitting device.

[0364] Experimental Examples 1-1 to 1-13 and Comparative Examples 1-2 to 1-8

[0365] Organic light-emitting devices of Experimental Examples 1-1 to Experimental Examples 1-13 and Comparative Examples 1-2 to Comparative Examples 1-8 were prepared using the same method as Comparative Example 1-1 except that RH-A was replaced as shown in Table 1.

[0366]

[0367] Current was applied to the organic light-emitting devices prepared in Experimental Examples 1-1 to 1-13 and Comparative Examples 1-1 to 1-8, and the voltage, efficiency, and lifespan were measured. The results are shown in Table 1 below. At this time, the voltage and efficiency were measured by applying 10 mA / cm 2 The current density is measured, LT 97 Indicates that the current density is 20mA / cm 2 The time it takes for the initial brightness to drop to 97%.

[0368] [Table 1]

[0369]

[0370] The compound represented by Chemical Formula 1 of the present invention is composed of a quinoxaline unit that acts as an electron acceptor and a benzindolecarbazole unit that acts as an electron donor. Because the two units, each with completely different properties, are directly bonded and exchange charge within the molecule, the band gap is reduced. Furthermore, the benzindolecarbazole unit contains a naphthalene ring, which reduces the triplet energy. Consequently, both the singlet and triplet energies are low, facilitating energy transfer to the red dopant, making it suitable for use as the host for the red light-emitting layer.

[0371] When an indolecarbazole unit is used as an electron donor instead of benzindolecarbazole as in RH-D, the triplet energy cannot be sufficiently reduced, and energy transfer to the red dopant cannot proceed smoothly. As a result, the voltage, efficiency, and life are all poor.

[0372] In particular, the structure of Chemical Formula 1, by positioning the triplet-stabilizing naphthalene ring adjacent to the nitrogen atom bound to quinoxaline, further stabilizes the internal charge transfer between quinoxaline and benzindolocarbazole. As a result, compared to RH-F, which has a naphthalene ring further from the quinoxaline unit, it exhibits a longer lifespan.

[0373] Furthermore, the two nitrogen atoms within the benzindolecarbazole unit are positioned para to each other, maximizing the electron-donating effect and resulting in a high HOMO (Highest Occupied Molecular Orbital) energy level. As a result, the benzindolecarbazole structure of Chemical Formula 1 prevents hole capture by dopants, resulting in superior hole-transporting capability and device properties, compared to, for example, RH-B, where a sulfur atom, with lower electron-donating ability than nitrogen, is located in the same position, or RH-E and RH-G, which are located in the meta (meta) position rather than the para (para) position.

[0374] Furthermore, when compared with RH-A in which the electron donor property is adjusted using carbazole as a substituent, the stability of the substance is further improved when the electron donor property is adjusted using a fused ring structure compared to the structure using carbazole as a substituent.

[0375] Chemical Formula 1 of the present invention is based on a quinoxaline unit. The Ar unit and the fused ring carbazole unit are substituted at the ortho position, creating a face-to-face relationship. This π-π interaction between the two stabilizes the structure, resulting in a long-life structure. This can be seen by comparing it with RH-C, which uses a benzothienopyrimidine unit as an electron acceptor structure, or RH-H, which uses a quinazoline unit as an electron acceptor structure.

[0376] Therefore, when compared with the results of Comparative Examples 1-1 to 1-8 using similar structures, when the compound having the structure of Chemical Formula 1 is used as the main body of the red light-emitting layer of the organic electroluminescent device, the best device exhibiting low voltage, high efficiency and long life characteristics can be obtained.

[0377] Experimental Examples 2-1 to 2-7 and Comparative Examples 2-2 to 2-3

[0378] Organic light-emitting devices of Experimental Examples 2-1 to 2-14 and Comparative Examples 2-1 to 2-3 were prepared using the same method as Comparative Example 1-1, except that a mixture of two host compounds as shown in Table 2 was used instead of RH-A. In this case, when a mixture of two compounds was used as a host, the weight ratio between the host compounds is indicated in parentheses.

[0379]

[0380] [Table 2]

[0381]

[0382] As shown in Table 2, when the compound of Chemical Formula 1 is mixed with a compound having a biscarbazole structure, such as PGH1 or PGH2, and used as a host, hole injection into the light-emitting layer is facilitated, thereby reducing voltage. The location where holes and electrons meet and emit light within the light-emitting layer shifts toward the electron transport layer, broadening the device's lifetime. This effect, resulting from a shift in the hole-electron balance, can occur with reduced device efficiency. However, the compound of Chemical Formula 1 minimizes this efficiency reduction while exhibiting low-voltage, long-life device characteristics. In particular, a comparison with Comparative Examples 2-1 and 2-3 shows that this effect is more pronounced in the compound having the structure of Chemical Formula 1.

Claims

1. A compound represented by the following chemical formula 1: Chemical formula 1 Wherein in the chemical formula 1, Ar is a phenyl group, a carbazolyl group, or a fluorenyl group substituted with a methyl group, R1, R4 and R5 are the same or different from each other and are each independently hydrogen, deuterium or a halogen group, R2 and R3 are the same or different and are independently hydrogen or deuterium, or multiple R2s are combined to form a benzofuran ring. r1 is an integer from 0 to 6, r2 to r4 are each an integer from 0 to 4, r5 is an integer from 0 to 2, When r1 to r5 are 2 or more, the structures in the brackets are the same or different from each other. m is 1 and n is 0, X2 is a direct bond, and X1 does not exist because it is not bound.

2. The compound according to claim 1, wherein Ar of the chemical formula 1 is represented by any one of the following structures: In the structure described, B1, B5 and B8 are each independently hydrogen, B12 and B13 are methyl groups. b1 is an integer from 0 to 5, b5 is an integer from 0 to 7, b8 is an integer from 0 to 8, When b1, b5, and b8 are 2 or more, the structures within the two or more brackets are identical to each other.

3. The compound according to claim 1, wherein The chemical formula 1 is selected from the following compounds:

4. An organic light-emitting device, comprising: A first electrode, a second electrode opposite to the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound represented by Chemical Formula 1 according to any one of claims 1 to 3.

5. The organic light emitting device according to claim 4, wherein The organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1. The organic light-emitting device according to claim 4 , wherein: The organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1 as a host of the light-emitting layer.

7. The organic light-emitting device according to claim 6, wherein: The light-emitting layer further comprises a compound represented by the following Chemical Formula 8 as an additional host, Based on 100 parts by weight of the entire body, the compound represented by Chemical Formula 1 is 20 to 50 parts by weight: Chemical formula 8 In the chemical formula 8, R a and R b are the same as or different from each other and are each independently a phenyl group, a biphenyl group, a naphthyl group, or a dibenzofuranyl group which may be substituted or unsubstituted by a naphthyl group, R c and R d are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; or an amino group, r and s are each an integer of 0 to 7. When r is 2 or greater, Rc's are the same or different from each other. When s is 2 or greater, Rd's are the same or different from each other.

8. The organic light emitting device according to claim 7, wherein: The chemical formula 8 is represented by any one of the following compounds:

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