Organic compound and organic light-emitting device comprising same

Abstract

The present invention relates to an organic compound used for a light-emitting layer in an organic light-emitting device, and an organic light-emitting device comprising same. The organic light-emitting device using the compound according to the present invention as a host of the light-emitting layer thereof can operate at low voltages and has significantly improved light-emitting efficiency and lifespan, and thus can be usefully employed throughout the industry for lighting devices and various display devices such as flat-panel, flexible, and wearable displays.

Description

Organic compounds and organic light-emitting devices containing the same

[0001] The present invention relates to an organic compound employed in a light-emitting layer in an organic light-emitting device and an organic light-emitting device comprising the same.

[0002] An organic light-emitting device is a self-luminous device in which electrons injected from an electron injection electrode (cathode electrode) and holes injected from a hole injection electrode (anode electrode) combine in a light-emitting layer to form excitons, and the excitons emit energy, thereby emitting light. Such an organic light-emitting device is attracting attention as a next-generation light source due to its advantages of low operating voltage, high brightness, wide viewing angle, and fast response speed, and its applicability to full-color flat panel light-emitting displays.

[0003] In order for these organic light-emitting devices to exhibit the above-described characteristics, the structure of the organic layers within the device must be optimized, and the materials that make up each organic layer, such as hole injection materials, hole transport materials, hole blocking materials, luminescent materials, electron transport materials, electron injection materials, and electron blocking materials, must first be supported by stable and efficient materials. However, the development of the structure of the organic layers and each material for stable and efficient organic light-emitting devices is still continuously necessary.

[0004] In particular, to obtain maximum efficiency in the light-emitting layer, the energy band gaps of the host and dopant must be appropriately combined so that holes and electrons can move to the dopant through stable electrochemical pathways to form excitons.

[0005] Accordingly, the present invention aims to provide a light-emitting layer host material having a characteristic structure and a high-efficiency, long-life organic light-emitting device including the same having significantly improved lifespan and luminous efficiency.

[0006] In order to solve the above problem, the present invention provides an organic compound represented by the following [chemical formula 1] and an organic light-emitting device including the same as a host in a light-emitting layer.

[0007] [Chemical Formula 1]

[0008]

[0009] In the above [chemical formula 1],

[0010] (i) At least one of R1 to R8 is characterized by being selected from among the following [structural formula b] to [structural formula f].

[0011] (ii) R9 to R 11 At least one of them is characterized by having the following [structural formula a].

[0012] [Structural formula b] [Structural formula c] [Structural formula d]

[0013]

[0014] [Structural formula e] [Structural formula f]

[0015]

[0016] [Structural formula a]

[0017]

[0018] The specific structures of the above [chemical formula 1], [structural formula a], and [structural formula b] to [structural formula f] and the specific compounds and definitions of each substituent according to the present invention implemented accordingly will be described later.

[0019] The present invention relates to an organic compound employed in a light-emitting layer in an organic light-emitting device and to an organic light-emitting device comprising the same. When the compound according to the present invention is employed as a host in the light-emitting layer, a high-efficiency, long-life organic light-emitting device having low-voltage operation and significantly improved light-emitting efficiency and lifespan can be realized, and thus can be usefully utilized in various display devices such as lighting devices, flat panel displays, flexible displays, and wearable displays.

[0020] Hereinafter, the present invention will be described in more detail.

[0021] One aspect of the present invention relates to a compound represented by the following [chemical formula 1].

[0022] [Chemical Formula 1]

[0023]

[0024] In the above [chemical formula 1],

[0025] R1 to R8 are the same or different, and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms, a fused ring group of an aromatic ring having 5 to 30 carbon atoms, and the following [structural formula b] to [structural formula f].

[0026] However, at this time, it is characterized in that at least one of the above R1 to R8 is selected from among the following [structural formula b] to [structural formula f].

[0027] [Structural formula b] [Structural formula c] [Structural formula d]

[0028]

[0029] [Structural formula e] [Structural formula f]

[0030]

[0031]

[0032] Also, the above R9 to R 11 At least one of them is [structural formula a], and the rest are the same or different from each other, and are each independently hydrogen or deuterium.

[0033] [Structural formula a]

[0034]

[0035] In the above [structural formula a] to [structural formula f],

[0036] R 12 Inland R 14 are the same or different from each other, and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a fused ring group of a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 5 to 30 carbon atoms.

[0037] L1 is any one selected from O, S, a substituted or unsubstituted arylene group, and a substituted or unsubstituted heteroarylene group, and m is an integer from 1 to 3, and when m is 2 or more, multiple L1s are the same or different from each other.

[0038] * in [structural formula a] is R9 to R 11 It is a position where it binds to any one of R1 to R8, and * in [structural formula b] is a position where it binds to any one of R1 to R8.

[0039] Y are identical or different and each independently CR 18 or N, and X is NR 19 , O, S, and SiR 20 R 21 One of the following is selected.

[0040] Z is NR 22 , one of O and S.

[0041] However, (i) X of the above [structural formula d] is NR 19 and Y is CR 18In this case, L1 of the above [structural formula a] is O or S, and (ii) X of the above [structural formula f] is NR 19 and Y is CR 18 and Z is NR 22 In this case, L1 of the above [structural formula a] is O or S.

[0042] L2 is any one selected from a single bond, a substituted or unsubstituted aryl group having 3 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and n is an integer from 0 to 2, and when n is 2 or more, multiple L2s are the same or different from each other.

[0043] The above R 18 Inland R 22 One of which is connected to R1 to R8, and the rest are the same or different, and each independently is one selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a fused ring group of a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 5 to 30 carbon atoms.

[0044]

[0045] In addition, 'substitution' in 'substituted or unsubstituted' means a deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 30 carbon atoms, an alkylaryl group having 7 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms or a heteroarylalkyl group having 2 to 30 carbon atoms, an aliphatic ring having 3 to 30 carbon atoms, a fused ring group of an aromatic ring having 5 to 30 carbon atoms, a fused ring group of 1 to 24 carbon atoms. It means being substituted with one or more identical or different substituents selected from the group consisting of an alkoxy group, an amine group having 0 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 1 to 24 carbon atoms, and an arylthionyl group having 6 to 24 carbon atoms, and at least one hydrogen in each substituent can be replaced with deuterium.

[0046]

[0047] In addition, another aspect of the present invention relates to an organic light-emitting device comprising a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer preferably includes a compound represented by [chemical formula 1] defined above as a host of a light-emitting layer including a host and a dopant.

[0048] [Chemical Formula 1]

[0049]

[0050]

[0051] In addition, the light-emitting layer is a structure composed of a host and a dopant, and the light-emitting layer may further include a dopant material. At this time, the content of the dopant may be typically selected in a range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

[0052] In addition, the organic compound represented by [chemical formula 1] used in the above host is characterized in that it is used in a blue phosphorescent host.

[0053]

[0054] In the present invention, the dopant compound included in the light-emitting layer is not a fluorescent dopant material that only transfers to a singlet state using the Förster energy transfer method in the existing Host-Dopant system, but a phosphorescent dopant material of a metal complex including at least one metal selected from Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Re, Pd, etc. that transfers without distinguishing between singlet and triplet states using the Dexter energy transfer method, and any known dopant material can be used without special limitation as long as it emits light from a triplet exciton.

[0055] As a metal complex, Ir, Pt and Pd can be preferably selected, and specific examples include Ir(ppy)3, Ir(ppy)2acac, Ir(Bt)2acac, Ir(MDQ)2acac, Ir(mppy)3, Ir(piq)3, Ir(piq)2acac, Ir(pq)2acac, Ir(mpp)2acac, F2Irpic, (F2ppy)2Ir(tmd), Ir(ppy)2tmd, Ir(pmi)3, Ir(pmb)3, FCNIr, FCNIrpic, FIr6, FIrN4, FIrpic, PtOEP, Ir(chpy)3,P0-01(C 31 H 23IrN2O2S2), Ir(ppz)3, Ir(dfppz)3, PtNON, Pt-10, Pt-11, etc., but are not limited thereto.

[0056]

[0057] In addition, the light-emitting layer may additionally include various hosts and various dopant materials in addition to the host and dopant compounds according to the present invention, and accordingly, in the light-emitting layer, not only the host but also the dopant material may be used by mixing or laminating one or more different compounds.

[0058] As one embodiment of the present invention, the organic light-emitting device according to the present invention includes an organic layer interposed between the first electrode and the second electrode, and the host in the light-emitting layer additionally includes at least one additional host compound in addition to one compound represented by the above-described [chemical formula 1], so that two or more host compounds can be mixed or laminated and used.

[0059] Here, in the case where at least one additional host compound is additionally included in addition to one compound represented by the above [chemical formula 1] and two or more host compounds are mixed or laminated and used, a compound having an electron acceptor moiety can be used as the additional host, and due to the HOMO / LUMO levels of the high hole injection and electron injection barrier resulting from mixing or laminating with [chemical formula 1] having a boron compound derivative as an electron donor moiety, the recombination region is limited to the interface of the two hosts, thereby minimizing current loss, etc., thereby enabling the implementation of a high-efficiency, long-life organic light-emitting device.

[0060] At this time, the compound having the electron acceptor moiety is a compound having a moiety that has an environment in which electrons can be easily received from the outside, such as an azine compound, which is a nitrogen-containing aromatic heterocycle such as pyridine, pyrimidine, triazine, etc., and a compound substituted with a cyano group (-CN), and preferably may include a compound including a heteroaryl group including 1 to 3 N (nitrogen) in the molecule; or an aryl group including 1 to 3 cyano groups (-CN) in the molecule.

[0061]

[0062] More specifically, the host in the light-emitting layer of the organic light-emitting device according to the present invention may be used by mixing one or more organic compounds represented by the following [Chemical Formula 2] in addition to the compound represented by the above [Chemical Formula 1], or the compound represented by the following [Chemical Formula 2] may be used by layering it on the upper or lower part of a layer including the compound represented by the above [Chemical Formula 1].

[0063] [Chemical Formula 2]

[0064]

[0065] In the above [chemical formula 2],

[0066] X1 to X3 are identical or different and are each independently N or CR. 26 However, at least one of the above X1 to X3 is N, and at least two of the above X1 to X3 are CR 26 In this case, each CR 26 are identical or different from each other.

[0067] L3 to L5 are the same or different, and each independently represents a single bond or one selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and a divalent ring group in which a substituted or unsubstituted aliphatic ring having 3 to 24 carbon atoms and an aromatic ring having 5 to 24 carbon atoms are fused.

[0068] m1 to m3 are the same or different from each other, and are each independently an integer from 1 to 2, but when each is an integer of 2, each of L3 to L5 is the same or different from each other.

[0069] The above R 23 Inland R 25 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 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 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a ring group in which a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 5 to 30 carbon atoms are fused, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms Any one selected from an alkylthioxy group, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group.

[0070]

[0071] In the above [Chemical Formula 2], 'substitution' in 'substituted or unsubstituted' means deuterium, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, an alkylaryl group having 7 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroarylalkyl group having 2 to 30 carbon atoms, a ring group in which an aliphatic ring having 3 to 24 carbon atoms and an aromatic ring having 5 to 24 carbon atoms are fused, an alkoxy group having 1 to 24 carbon atoms, an alkyl group having 1 to 30 carbon atoms It means that it is substituted with one or two or more substituents selected from the group consisting of an amine group, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, an arylthionyl group having 6 to 24 carbon atoms, a cyano group, a halogen group, a hydroxy group, and a nitro group, or that two or more of the above substituents are substituted with a substituent that is connected, and hydrogen in the above substituents can be replaced with one or more deuterium, and two or more adjacent substituents can be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0072]

[0073] In addition, the light-emitting layer may additionally include various hosts and various dopant materials in addition to the dopant and host.

[0074]

[0075] The organic layer of the organic light-emitting device according to the present invention may be formed as a single layer structure, but may also be formed as a multilayer 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 hole blocking layer, a light-emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, etc. However, it is not limited thereto, and a smaller or larger number of organic layers may be included, and the organic layer structure of a preferred organic light-emitting device according to the present invention will be described in more detail in the following examples.

[0076]

[0077] In addition, according to one embodiment of the present invention, the dopant may include at least one organometallic compound, and may be used by mixing or layering a polycyclic ring compound represented by the following [chemical formula 3] in addition to the organometallic compound.

[0078] Accordingly, in an organic light-emitting device according to one embodiment of the present invention, the light-emitting layer may be configured to include a first host, a second host, an organometallic compound, and a polycyclic compound (boron thermally activated delayed fluorescent emitter) material of the following [chemical formula 3].

[0079] In this case, the organometallic compound functions as a sensitizer, and the polycyclic compound functions as a luminescent dopant, such that the sensitizer compound can receive excitons from the first host and the second host and transfer them to the luminescent dopant.

[0080] Accordingly, excitons from the sensitizer are transferred to the light-emitting dopant compound through the Dexter energy transfer (DET) or Forster resonance transfer (FRET) mechanism, and the exciton energy transferred to the light-emitting dopant compound can emit light while being transferred to the ground state. At this time, the excitons of the sensitizer can be transferred from the first host and the second host through the FRET mechanism, or can be formed by the transfer of excitons generated from the host through the DET mechanism.

[0081] Accordingly, energy transfer through FRET and DET mechanisms between the sensor and the light-emitting dopant is facilitated, and triplet-triplet annihilation is suppressed, enabling the production of a high-efficiency organic light-emitting device.

[0082]

[0083] A boron thermally activated delayed fluorescent emitter, which is a polycyclic ring compound represented by the following [chemical formula 3], can improve the lifespan by reducing the number of long-lived triplet excitons involved in the deterioration of the device by enabling Förster energy transfer from the triplet of the phosphorescence sensitizer to the singlet of the boron thermally activated delayed fluorescent emitter.

[0084] In addition, because it has a high molar extinction coefficient, the efficiency and lifespan can be improved due to effects such as an increase in the rate of fluorescence resonance energy transfer from the phosphorescence sensitizer to the emitter and a narrowing of the emission spectrum due to the multiple resonance effect, thereby increasing color purity.

[0085]

[0086] [Chemical Formula 3]

[0087]

[0088] In the above [chemical formula 3],

[0089] Y1 and Y2 are the same or different and are independently O, S, NR 27 , CR 28 R 29 , SiR 30 R 31 and GeR 32 R 33 One of the following is selected.

[0090] A1 to A3 rings are the same or different, and each independently represent one selected from a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocycle having 2 to 30 carbon atoms, a substituted or unsubstituted aliphatic heterocycle having 2 to 30 carbon atoms, and a ring in which a substituted or unsubstituted aliphatic ring having 3 to 24 carbon atoms and an aromatic ring having 5 to 24 carbon atoms are fused.

[0091] The above R 27 Inland R 33are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 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 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a ring group in which a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 5 to 30 carbon atoms are fused, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms Any one selected from an alkylthioxy group, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group.

[0092] The above R 27 Inland R 33 It can be connected to the above A1 to A3 rings to additionally form an alicyclic or aromatic monocyclic or polycyclic ring.

[0093] The above R 28 Wow R 29 , R 30 and R 31 and R 32 and R 33 Each of them can be linked to each other to form an additional alicyclic or aromatic monocyclic or polycyclic ring.

[0094]

[0095] In addition, the 'substitution' in 'substituted or unsubstituted' in the above [chemical formula 3] refers to a deuterium, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, an alkylaryl group having 7 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroarylalkyl group having 2 to 30 carbon atoms, a ring group in which an aliphatic ring having 3 to 24 carbon atoms and an aromatic ring having 5 to 24 carbon atoms are fused, an alkoxy group having 1 to 24 carbon atoms, an alkyl group having 1 to It means being substituted with one or more substituents selected from the group consisting of an amine group having 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, an arylthionyl group having 6 to 24 carbon atoms, a cyano group, a halogen group, a hydroxy group and a nitro group, and in the case of two or more, they are the same or different, and at least one hydrogen in each substituent can be replaced with deuterium.

[0096]

[0097] Meanwhile, in the present invention, the carbon number range of the alkyl group or aryl group in the 'substituted or unsubstituted alkyl group having 1 to 30 carbon atoms', 'substituted or unsubstituted aryl group having 6 to 50 carbon atoms', etc. means the total number of carbon atoms constituting the alkyl portion or aryl portion when the substituent is viewed as unsubstituted without considering the substituted portion. For example, a phenyl group substituted with a butyl group at the para-position means an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

[0098]

[0099] In addition, in the present invention, the meaning of forming an additional ring by being connected to each other or to adjacent groups means that among the specified substituents, adjacent substituents can be connected to each other, or a specified substituent and another adjacent group can be connected to each other to form a substituted or unsubstituted alicyclic or aromatic ring, and the 'adjacent group' can mean 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 can be interpreted as 'adjacent groups', and a pair of connected substituents additionally form a ring by removing one hydrogen radical from each and connecting them, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring can be replaced by heteroatoms such as N, O, S, Si, Ge, etc.

[0100]

[0101] In the present invention, the alkyl group may be straight-chain or branched, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, an n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohectylmethyl group, an octyl group, an n-octyl group, a tert-octyl group, a 1-methylheptyl group, Examples thereof include, but are not limited to, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, and 5-methylhexyl group.

[0102] In the present invention, specific examples of the arylalkyl group include, but are not limited to, phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl, naphthylethyl, etc.

[0103] In the present invention, specific examples of the alkylaryl group include, but are not limited to, tolyl, xylenyl, dimethylnaphthyl, t-butylphenyl, t-butylnaphthyl, t-butylphenanthryl, etc.

[0104] In the present invention, the alkenyl group includes a straight chain or a branched chain, and may be further substituted by another substituent, and specifically, includes 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, a styrenyl group, etc., but is not limited thereto.

[0105] In the present invention, the alkynyl group also includes a straight chain or branched chain, and may be further substituted by another substituent, and examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0106] In the present invention, the aromatic hydrocarbon ring or aryl group may be monocyclic or polycyclic, and polycyclic means a group directly connected to or condensed with another ring group, and the other ring group may be an aromatic hydrocarbon ring, but may also be another type of ring group, for example, an aliphatic heterocycle, an aliphatic hydrocarbon ring, an aromatic heterocycle, etc. Examples of monocyclic aryl groups include a phenyl group, a biphenyl group, a terphenyl group, etc., and examples of polycyclic aryl groups include a naphthyl group, anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a tetracenyl group, a chrysenyl group, a fluorenyl group, an acenaphthacenyl group, a triphenylene group, a fluoranthene group, etc., but the scope of the present invention is not limited to these examples.

[0107] In the present invention, the aromatic heterocycle or heteroaryl group is an aromatic ring containing at least one heteroatom, and includes a heteroatom such as O, S, N, P, Si or Ge, and examples thereof include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a pyrimidyl group, a triazine group, a triazole group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinolinyl group, a quinazoline group, a quinoxalinyl group, a phthalazinyl group, a pyrido pyrimidinyl group, a pyrido pyrazinyl group, a pyrazino pyrazinyl group, an isoquinoline group, an indole group, a carbazole group, an indolocarbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, Examples thereof include, but are not limited to, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, and phenothiazinyl group.

[0108] In the present invention, an aliphatic hydrocarbon ring or cycloalkyl group means a ring that is not aromatic and is composed only of carbon and hydrogen atoms, and includes, for example, a monocyclic ring or a polycyclic ring, and may be further substituted by another substituent. A polycyclic ring means a group that is directly connected to or condensed with another ring group, and the other ring group may be an aliphatic hydrocarbon ring, but may also be another type of ring group, such as an aliphatic heterocycle, an aromatic hydrocarbon ring, an aromatic heterocycle, etc. Specifically, it includes, but is not limited to, cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, an adamantyl group, a bicycloheptanyl 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, and a cyclooctyl group, and cycloalkanes such as cyclohexane and cyclopentane, and cyclocycloalkenes such as cyclohexene and cyclobutene.

[0109] In the present invention, an aliphatic heterocycle or heterocycloalkyl group means an aliphatic ring containing at least one heteroatom, and includes a heteroatom such as O, S, Se, N or Si, and also includes a monocyclic ring or a polycyclic ring, and may be further substituted by another substituent, and a polycyclic ring means a group in which a heterocycloalkyl or a heterocycloalkane is directly connected to or condensed with another ring group, and the other ring group may be an aliphatic heterocycle, but may also be another type of ring group, such as an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, an aromatic heterocycle, etc.

[0110] In the present invention, a ring (group) in which an aliphatic ring and an aromatic ring are fused is an aliphatic aromatic mixed ring (group), which means a ring in which two or more rings are connected and condensed with each other, and in which an aliphatic ring and an aromatic ring are condensed to have non-aromaticity as a whole, and more specifically, it means an aromatic hydrocarbon ring condensed with an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring condensed with an aliphatic heterocycle, an aromatic heterocycle condensed with an aliphatic heterocycle, an aromatic hydrocarbon ring condensed with an aliphatic hydrocarbon ring, an aromatic heterocycle condensed with an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring condensed with an aliphatic heterocycle, an aromatic heterocycle condensed with an aliphatic It can be a heterocyclic group, and specific examples include a tetrahydronaphthyl group, a tetrahydrobenzocycloheptene group, a tetrahydrophenanthrene group, a tetrahydroanthracenyl group, an octahydrotriphenylene group, a tetrahydrobenzothiophene group, a tetrahydrobenzofuranyl group, a tetrahydrocarbazole group, a tetrahydroquinoline group, etc. In addition, in a ring (group) in which an aliphatic ring and an aromatic ring are fused, carbon can be substituted with a heteroatom such as N, O, S, Si, Ge, or P.

[0111] In the present invention, the alkoxy group may be specifically methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, etc., but is not limited thereto.

[0112] In the present invention, the silyl group may include -SiH3, an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, an arylheteroarylsilyl group, a heteroarylsilyl group, etc., and the arylsilyl group means a silyl group in which one, two, or three hydrogens are substituted with an aryl group in -SiH3, and the alkylsilyl group means an amine in which one, two, or three hydrogens are substituted with alkyl in -SiH3, and the alkylarylsilyl group means a silyl group in which at least one hydrogen is substituted with an alkyl group and an aryl group, and includes one or two alkyl groups and two or one corresponding aryl groups, and the arylheteroarylsilyl group means a silyl group in which at least one hydrogen is substituted with an aryl group and a heteroaryl group, and includes one or two aryl groups and two or one corresponding heteroaryl groups, in -SiH3. In other words, the heteroarylsilyl group means a silyl group in which one, two, or three hydrogens are substituted with a heteroaryl group in -SiH3, and examples of the arylsilyl group include a substituted or unsubstituted monoarylsilyl group, a substituted or unsubstituted diarylsilyl group, or a substituted or unsubstituted triarylsilyl group, and the alkylsilyl group and the heteroarylsilyl group are also included.

[0113] Here, each aryl group in the arylsilyl group, heteroarylsilyl group, and arylheteroarylsilyl group may be a monocyclic aryl group or a polycyclic aryl group, and each heteroaryl group in the arylsilyl group, heteroarylsilyl group, and arylheteroarylsilyl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

[0114] In addition, specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc., and at least one hydrogen atom of the silyl group can be substituted with a substituent similar to that of the aryl group.

[0115] In the present invention, the amine group may include -NH2, an alkylamine group, an arylamine group, an alkylarylamine group, an arylheteroarylamine group, a heteroarylamine group, etc., and the arylamine group means an amine in which one or two hydrogens in -NH2 are substituted with an aryl group, the alkylamine group means an amine in which one or two hydrogens in -NH2 are substituted with an alkyl group, the alkylarylamine group means an amine in which one hydrogen in -NH2 is substituted with an alkyl group and the other hydrogen in -NH2 is substituted with an aryl group, the arylheteroarylamine group means an amine in which one hydrogen in -NH2 is substituted with an aryl group and the other hydrogen in -NH2 is substituted with a heteroaryl group, and the heteroarylamine group means an amine in which one or two hydrogens in -NH2 are substituted with a heteroaryl group, and examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted There is a diarylamine group, or a substituted or unsubstituted triarylamine group, and the same applies to the alkylamine group and heteroarylamine group.

[0116] Here, each aryl group in the arylamine group, heteroarylamine group, and arylheteroarylamine group may be a monocyclic aryl group or a polycyclic aryl group, and each heteroaryl group in the arylamine group, heteroarylamine group, and arylheteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. Or, it may be a polycyclic aryl group, and each heteroaryl group in the arylamine group, heteroarylamine group, and arylheteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

[0117] In the present invention, the germanium group (or germane group) may include -GeH3, an alkylgermanium group, an arylgermanium group, a heteroarylgermanium group, an alkylarylgermanium group, an alkylheteroarylgermanium group, an arylheteroarylgermanium group, etc., and the definitions of these are as described for the silyl group, but may be applied to each substituent as a substituent obtained by substituting a germanium atom (Ge) for a silicon atom (Si) in the silyl group.

[0118] In addition, specific examples of the germanium group include trimethylgermane, triethylgermane, triphenylgermane, trimethoxygermane, dimethoxyphenylgermane, diphenylmethylgermane, diphenylvinylgermane, methylcyclobutylgermane, dimethylfurylgermane, etc., and at least one hydrogen atom of the germanium group can be substituted with a substituent similar to that of the aryl group.

[0119] In the present invention, specific examples of the aryloxy group include, but are not limited to, a phenoxy group, a p-toryloxy group, a m-toryloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, and a 9-phenanthryloxy group, and examples of the arylthioxy group include, but are not limited to, a phenylthioxy group, a 2-methylphenylthioxy group, and a 4-tert-butylphenylthioxy group.

[0120] In the present invention, examples of halogen groups include fluorine, chlorine, bromine or iodine.

[0121] In the present invention, hydrogen includes tritium.

[0122]

[0123] According to one embodiment of the present invention, the compound represented by the above-mentioned [chemical formula 1] may be any one selected from compounds represented by the following chemical formulas, but the scope thereof is not limited thereby.

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133] Hereinafter, one embodiment of an organic light-emitting device according to the present invention will be described in more detail.

[0134] The organic light-emitting device according to the present invention includes an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode. If necessary, a hole injection layer may be further included between the anode and the hole transport layer. In addition, an electron injection layer may be further included between the electron transport layer and the cathode. In addition, one or two intermediate layers may be further formed, a hole blocking layer or an electron blocking layer may be further formed, and as described above, an organic layer having various functions depending on the characteristics of the device, such as a capping layer, may be further included.

[0135]

[0136] Meanwhile, the specific structure of the organic light-emitting device according to one embodiment of the present invention, the manufacturing method thereof, and each organic layer material are as follows.

[0137] First, an anode is formed by coating an anode material on the upper surface of the substrate. Here, the substrate used is a substrate commonly used in organic light-emitting devices, but an organic substrate or transparent plastic substrate with excellent transparency, surface smoothness, ease of handling, and water resistance is preferred. In addition, the anode material used is indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity.

[0138] A hole injection layer is formed by vacuum thermal evaporation or spin coating of a hole injection layer material on top of the anode electrode, and then a hole transport layer is formed by vacuum thermal evaporation or spin coating of a hole transport layer material on top of the hole injection layer.

[0139] The above hole injection layer material can be used without particular limitation as long as it is commonly used in the art, and as specific examples, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine], NPD [N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD [N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine], DNTPD [N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine], etc. can be used.

[0140] In addition, the hole transport layer material is not particularly limited as long as it is one commonly used in the art, and for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (α-NPD) can be used.

[0141] Next, a hole-assisting layer and a light-emitting layer are successively stacked on top of the hole transport layer, and a hole-blocking layer can be selectively formed as a thin film on top of the light-emitting layer by a vacuum deposition method or a spin coating method. The hole-blocking layer prevents the lifespan and efficiency of the device from decreasing when holes pass through the organic light-emitting layer and flow into the cathode by using a material with a very low HOMO (Highest Occupied Molecular Orbital) level. The hole-blocking material used at this time is not particularly limited, but must have an electron transport ability and a higher ionization potential than the light-emitting compound, and representative examples thereof include BAlq, BCP, and TPBI.

[0142] As a material used in the above hole-blocking layer, BAlq, BCP, Bphen, TPBI, TAZ, BeBq2, OXD-7, Liq, etc. can be used, but are not limited thereto.

[0143] An electron transport layer is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, and then an electron injection layer is formed. A cathode electrode is formed by vacuum thermally depositing a metal for forming a cathode on top of the electron injection layer, thereby completing an organic light-emitting device according to one embodiment of the present invention.

[0144] Here, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. can be used as the metal for forming the cathode, and a transparent cathode using ITO or IZO can be used to obtain a front-emitting element.

[0145] The above electron transport layer material has the function of stably transporting electrons injected from the cathode, and a known electron transport material can be used. Examples of known electron transport materials include quinoline derivatives, particularly tris(8-quinolinolate)aluminum (Alq3), TAZ, BAlq, beryllium bis(benzoquinolin-10-olate: Bebq2), and oxadiazole derivatives (PBD, BMD, BND, etc.).

[0146]

[0147] In addition, each of the above organic layers can be formed by a single molecule deposition method or a solution process, wherein the deposition method refers to a method of forming a thin film by evaporating a material used as a material for forming each layer through heating in a vacuum or low pressure state, and the solution process refers to a method of forming a thin film by mixing a material used as a material for forming each layer with a solvent and using a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, or spin coating.

[0148] In addition, the organic light-emitting device according to the present invention can be used in a device selected from a flat panel display device, a flexible display device, a flat panel lighting device of a single color or white color, a flexible lighting device of a single color or white color, a vehicle display device, a virtual or augmented reality display device, etc.

[0149] Hereinafter, to aid in understanding the present invention, synthetic examples of preferred compounds and device examples are presented. However, the following examples are intended to illustrate the present invention and are not intended to limit the scope of the present invention.

[0150]

[0151] Synthesis Example 1: Synthesis of [HT-1]

[0152] Synthesis Example 1-1: Synthesis of A-1

[0153]

[0154] <a-1a> <a-1b> <a-1>

[0155] In a round bottom flask <a-1b> 50 g, <a-1a>187.8 g of sodium hydroxide, 220.3 g of potassium carbonate and 500 mL of N,N-dimethylformamide were added and refluxed for 24 hours. After the reaction was completed, the reaction solution was cooled to room temperature, filtered through Celite, and the filtrate was concentrated under reduced pressure and purified using column chromatography. <a-1>143 g (yield 77.8%) was obtained.

[0156]

[0157] Synthesis Example 1-2: Synthesis of A-2

[0158]

[0159] <a-1> <a-2a> <a-2>

[0160] In a round bottom flask <a-1> 143 g, <a-2a>63.8 g of sodium hydroxide, 171.4 g of potassium carbonate, and 720 mL of N,N-dimethylformamide were added and refluxed for 24 hours. After the reaction was completed, the reaction solution was cooled to room temperature, filtered through Celite, and the filtrate was concentrated under reduced pressure. After concentration, column chromatography was used to separate the solution. <a-2>133 g (yield 70.8%) was obtained.

[0161]

[0162] Synthesis Example 1-3: Synthesis of A-3

[0163]

[0164] <a-2> <a-3>

[0165] In a round bottom flask under nitrogen atmosphere <a-2>133 g of 1,300 mL of m-xylene was added, the reaction solution was cooled to 0°C, and stirred for 30 minutes. Then, 192 mL of 1.6 M n-butyllithium was slowly added dropwise, and when the addition was completed, the reaction solution was warmed to room temperature and stirred for 1 hour. After 1 hour, the reaction solution was cooled to -30°C, and 88 g of boron tribromide was added dropwise, and after the addition, the reaction solution was warmed to room temperature and stirred for 1 hour. Then, after cooling to 0°C again, 143.7 g of N,N-diisopropyl edylamine was added, and the reaction solution was reacted at 130°C for 12 hours. When the reaction was completed, the reaction solution was cooled to room temperature, filtered, the solid was washed with methanol, and recrystallized with monochlorobenzene. <a-3>38.4 g (yield 34.2%) was obtained.

[0166]

[0167] Synthesis Example 1-4: Synthesis of A-4

[0168]

[0169] <a-3a> <a-4>

[0170] In a round bottom flask <a-3a>30 g of bispinacolatodiboron, 27.5 g of bisdiphenylphosphinoferrocene dichloropalladium, 1.6 g of potassium acetate, 21.26 g of potassium acetate, and 300 mL of 1,4-dioxane were added and refluxed for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature and filtered through Celite. The filtrate was concentrated under reduced pressure and purified by column chromatography. <a-4>21.2 g (yield 63.6%) was obtained.

[0171]

[0172] Synthesis Example 1-5: Synthesis of A-5

[0173]

[0174] <a-3> <a-4> <a-5>

[0175] In a round bottom flask <a-3> 16 g, <a-4>21.2 g of triphenylphosphine tetrakispalladium, 1.45 g of potassium carbonate, 14.42 g of 1,4-dioxane, and 45 mL of water were added and refluxed for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature and filtered, and the filtered solid was washed with methanol and recrystallized from 1,2-dichlorobenzene. <a-5>20.5 g (yield 77%) was obtained.

[0176]

[0177] Synthesis Example 1-6: Synthesis of A-6

[0178]

[0179] <a-4a> <a-2b> <a-6>

[0180] In a round bottom flask <a-2b> 60 g, <a-4a>68.5 g (0.514 mol), 218.3 g of potassium phosphate tribasic, and 480 mL of N,N-dimethylacetamide were added and refluxed for 24 hours. After the reaction was completed, the reaction solution was cooled to room temperature, poured into water, stirred for 1 hour, and then separated into layers with dichloromethane and water and concentrated under reduced pressure. After concentration, it was recrystallized from tetrahydrofuran and heptane. <a-6>38.6 g (yield 54.3%) was obtained.

[0181]

[0182] Synthesis Example 1-7: Synthesis of [HT-1]

[0183]

[0184] <a-5> <a-6>[HT-1]

[0185] In a round bottom flask <a-5> 20.5 g, <a-6>7.98 g of trisdibenzylideneacetone dipalladium, 0.6 g of sodium tert-butoxide, 6.17 g of tri-tert-butylphosphine, and 210 mL of toluene were added and refluxed for 14 hours. After the reaction was completed, the reaction solution was cooled to room temperature, filtered, and washed with water and methanol. The obtained solid was purified by column chromatography to obtain [HT-1] 17.1 g (yield 65.8%).

[0186] MS(MALDI-TOF): m / z 809.27[M] +

[0187]

[0188] Synthesis Example 2: Synthesis of [HT-2]

[0189] Synthesis Example 2-1: Synthesis of B-1

[0190]

[0191] <b-1a> <b-1>

[0192] Used in the above synthesis example 1-4 <a-3a>instead <b-1a>Synthesized in the same way except that <b-1>was obtained. (Yield 71%)

[0193]

[0194] Synthesis Example 2-2: Synthesis of B-2

[0195]

[0196] <a-3> <b-1> <b-2>

[0197] Used in the above synthesis example 1-5 <a-4>instead <b-1>Synthesized in the same way except that <b-2>was obtained. (Yield 68%)

[0198]

[0199] Synthesis Example 2-3: Synthesis of B-3

[0200]

[0201] <b-1a> <b-1b> <b-3>

[0202] In a round bottom flask <b-1b> 50 g, <b-1a>Add 57.7 g of tetrakistriphenylphosphine palladium, 5.7 g of potassium carbonate, 58.2 g of potassium carbonate, 350 mL of toluene, 85 mL of ethanol, and 210 mL of water and reflux for 12 hours. After the reaction is complete, cool the reaction solution to room temperature, separate the layers with ethyl acetate and water, and concentrate the organic layer and then use column chromatography to purify it. <b-3>76 g (yield 90.8%) was obtained.

[0203]

[0204] Synthesis Example 2-4: Synthesis of B-4

[0205]

[0206] <b-3> <b-4>

[0207] In a round bottom flask <b-3>76 g of triphenylphosphine, 212.2 g of triphenylphosphine, and 760 mL of 1,2-dichlorobenzene were added and refluxed for 24 hours. After the reaction was completed, the reaction solution was cooled to room temperature, filtered through Celite, and the filtrate was concentrated. After concentration, column chromatography was used to separate the residue. <b-4>43 g (yield 63.6%) was obtained.

[0208]

[0209] Synthesis Example 2-5: Synthesis of [HT-2]

[0210]

[0211] <b-2> <b-4>[HT-2]

[0212] Used in the above synthesis example 1-7 <a-5>instead <b-2>Use , <a-6>instead <b-4>[HT-2] was obtained by the same method except that [HT-2] was used. (Yield 43.6%)

[0213] MS(MALDI-TOF): m / z 859.27[M] +

[0214]

[0215] Synthesis Example 3: Synthesis of [HT-3]

[0216] Synthesis Example 3-1: Synthesis of C-1

[0217]

[0218] <c-1a> <c-1b> <c-1>

[0219] In a round bottom flask <c-1a>20 g (96 mmol) of tetrahydrofuran (200 mL) was added under a nitrogen atmosphere, cooled to -78 °C, and 66 mL of 1.6 M n-butyllithium was slowly added and stirred for 1 hour. In another reactor <c-1b>44.5 g (144 mmol) of tetrahydrofuran was added to 250 mL under a nitrogen atmosphere and completely dissolved. <c-1a>It was slowly added to the reactor and stirred at room temperature for 12 hours. After the reaction was completed, water was added to extract and separated using column chromatography. <c-1>32.3 g (yield 70%) was obtained.

[0220]

[0221] Synthesis Example 3-2: Synthesis of C-2

[0222]

[0223] <c-1> <a-2a> <c-2>

[0224] Used in the above synthesis example 1-1 <a-1a>instead <c-1>Use , <a-1b>instead <a-2a>Synthesized in the same way except that <c-2>(Yield 76%)

[0225]

[0226] Synthesis Example 3-3: Synthesis of C-3

[0227]

[0228] <c-2> <c-3>

[0229] Used in the above synthesis example 1-3 <a-2>instead <c-2>Synthesized in the same way except that <c-3>was obtained. (Yield 31%)

[0230]

[0231] Synthesis Example 3-4: Synthesis of [HT-3]

[0232]

[0233] <c-3> <c-2a>[HT-3]

[0234] Used in the above synthesis example 1-7 <a-5>instead <c-3>Use , <a-6>instead <c-2a>[HT-3] was obtained by the same method except that [HT-3] was used (yield 51%).

[0235] MS(MALDI-TOF): m / z 905.48[M] +

[0236]

[0237] Synthesis Example 4: Synthesis of [HT-4]

[0238] Synthesis Example 4-1: Synthesis of D-1

[0239]

[0240] <d-1a> <c-1b> <d-1>

[0241] Used in the above synthesis example 3-1 <c-1a>instead <d-1a>Synthesized in the same way except that <d-1>was obtained. (Yield 61%)

[0242]

[0243] Synthesis Example 4-2: Synthesis of D-2

[0244]

[0245] <d-1> <a-2a> <d-2>

[0246] Used in the above synthesis example 1-1 <a-1a>instead <d-1>Use , <a-1b>instead <a-2a>Synthesized in the same way except that <d-2>(Yield 72%)

[0247]

[0248] Synthesis Example 4-3: Synthesis of D-3

[0249]

[0250] <d-2> <d-3>

[0251] Used in the above synthesis example 1-3 <a-2>instead <d-2>Synthesized in the same way except that <d-3>(Yield 30%)

[0252]

[0253] Synthesis Example 4-4: Synthesis of [HT-4]

[0254]

[0255] <d-3> <c-2a>[HT-4]

[0256] Used in the above synthesis example 1-7 <a-5>instead <d-3>Use , <a-6>instead <c-2a>[HT-4] was obtained by the same method except that [HT-4] was used. (Yield 52%)

[0257] MS(MALDI-TOF): m / z 921.45[M] +

[0258]

[0259] Synthesis Example 5: Synthesis of [HT-5]

[0260] Synthesis Example 5-1: Synthesis of E-1

[0261]

[0262] <c-1> <a-1b> <e-1>

[0263] Used in the above synthesis example 1-1 <a-1a>instead <c-1>Synthesized in the same way except that <e-1>was obtained. (Yield 76%)

[0264]

[0265] Synthesis Example 5-2: Synthesis of E-2

[0266]

[0267] <e-1> <a-2a> <e-2>

[0268] Used in the above synthesis example 1-2 <a-1>instead <e-1>Synthesized in the same way except that <e-2>was obtained. (Yield 72%)

[0269]

[0270] Synthesis Example 5-2: Synthesis of E-3

[0271]

[0272] <e-2> <e-3>

[0273] Used in the above synthesis example 1-3 <a-2>instead <e-2>Synthesized in the same way except that <e-3>(Yield 30%)

[0274]

[0275] Synthesis Example 5-3: Synthesis of [HT-5]

[0276]

[0277] <e-3> <e-1a>[HT-5]

[0278] Used in the above synthesis example 1-7 <a-5>instead <e-3>Use , <a-6>instead <e-1a>[HT-5] was obtained by the same method except that [HT-5] was used. (Yield 55%)

[0279] MS(MALDI-TOF): m / z 904.47[M] +

[0280]

[0281] Synthesis Example 6: Synthesis of [HT-6]

[0282] Synthesis Example 6-1: Synthesis of F-1

[0283]

[0284] <e-3> <f-1a> <f-1>

[0285] Used in the above synthesis example 1-7 <a-5>instead <e-3>Use , <a-6>instead <f-1a>Synthesize in the same way except that <f-1>(Yield 50%)

[0286]

[0287] Synthesis Example 6-2: Synthesis of [HT-6]

[0288]

[0289] <f-1> <f-2a>[HT-6]

[0290] Used in the above synthesis example 1-7 <a-5>instead <f-1>Use , <a-6>instead <f-2a>[HT-6] was synthesized using the same method except that [HT-6] was used (yield 52%).

[0291] MS(MALDI-TOF): m / z 894.41[M] +

[0292]

[0293] Synthesis Example 7: Synthesis of [HT-7]

[0294] Synthesis Example 7-1: Synthesis of G-1

[0295]

[0296] <a-3> <g-1a> <g-1>

[0297] Used in the above synthesis example 1-5 <a-4>instead <g-1a>Synthesized in the same way except that <g-1>was synthesized. (Yield 80%)

[0298]

[0299] Synthesis Example 7-2: Synthesis of [HT-7]

[0300]

[0301] <g-1> <b-4>[HT-7]

[0302] Used in the above synthesis example 1-7 <a-5>instead <g-1>Use , <a-6>instead <b-4>[HT-7] was obtained by the same method except that [HT-7] was used. (Yield 55%)

[0303] MS(MALDI-TOF): m / z 878.39[M] +

[0304]

[0305] Synthesis Example 8: Synthesis of [HT-8]

[0306] Synthesis Example 8-1: Synthesis of H-1

[0307]

[0308] <h-1a> <h-1>

[0309] Used in the above synthesis example 1-4 <a-3a>instead <h-1a>Synthesized in the same way except that <h-1>(Yield 70%)

[0310]

[0311] Synthesis Example 8-2: Synthesis of [HT-8]

[0312]

[0313] <g-1> <h-1>[HT-8]

[0314] Used in the above synthesis example 1-5 <a-3>instead <g-1>Use , <a-4>instead <h-1>[HT-8] was obtained by the same method except that [HT-8] was used. (Yield: 72%)

[0315] MS(MALDI-TOF): m / z 831.39[M] +

[0316]

[0317] Synthesis Example 9: Synthesis of [HT-9]

[0318] Synthesis Example 9-1: Synthesis of [HT-9]

[0319]

[0320] <g-1> <i-1a>[HT-9]

[0321] Used in the above synthesis example 1-5 <a-3>instead <g-1>Use , <a-4>instead <i-1a>[HT-9] was obtained by the same method except that [HT-9] was used. (Yield: 72%)

[0322] MS(MALDI-TOF): m / z 789.36[M] +

[0323]

[0324] Examples 1 to 9: Manufacturing of organic light-emitting devices

[0325] After patterning the ITO glass to have a light-emitting area of ​​2 mm × 2 mm, it was cleaned. After mounting the ITO glass in a vacuum chamber, the base pressure was 1 × 10 -6 After making it torr, HATCN (50 Å) is deposited as a hole injection layer on the ITO, BCFN (600 Å) is deposited as a hole transport layer, and then PBCz (50 Å) is deposited as an electron blocking layer. As a light-emitting layer, a film (350 Å) is deposited by mixing the first host compound and the second host compound according to the present invention and 12 wt% of the dopant compound PBD, and then mSiTrz (50 Å) is deposited as a hole blocking layer, and mSiTrz: Liq (300 Å) is deposited as an electron injection and transport layer at a ratio of 1:1, and then Liq (10 Å) is deposited sequentially as an electron injection layer, and Al (1000 Å) is deposited as a cathode to manufacture an organic light-emitting device. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.

[0326] [HATCN] [BCFN] [PBCz]

[0327]

[0328] [PBD] [mSiTrZ] [Liq]

[0329]

[0330] [ET-1]

[0331]

[0332]

[0333] Comparative Examples 1 to 4

[0334] For comparative examples, organic light-emitting devices were manufactured in the same manner as in the above-described examples, except that [RH-1] to [RH-4] were used instead of the compounds according to the present invention as host compounds in the device structure, and the luminescence characteristics of the organic light-emitting devices were measured at 0.4 mA. The structures of [RH-1] to [RH-4] are as follows.

[0335] [RH-1] [RH-2] [RH-3]

[0336]

[0337] [RH-4]

[0338]

[0339]

[0340] Classification 1 Host 2 Host Driving Voltage (V) External Quantum Efficiency (%) Luminescence Color Lifetime (T80) Example 1 HT-1ET-14.5 16.7 Blue 149 Example 2 HT-2ET-14.4 16.9 Blue 159 Example 3 HT-3ET-14.2 17.6 Blue 185 Example 4 HT-4ET-14.3 17.5 Blue 180 Example 5 HT-5ET-14.1 17.8 Blue 190 Example 6 HT-6ET-14.1 17.8 Blue 188 Example 7 HT-7ET-14.3 17.2 Blue 175 Example 8 HT-8ET-14.5 16.6 Blue 158 Example 9 HT-9ET-14.4 16.5 Blue 156 Comparative Example 1RH-1ET-15.4 14.6 Blue 74 Comparative Example 2RH-2ET-15.7 14.1 Blue 68 Comparative Example 3RH-3ET-15.3 13.6 Blue 58 Comparative Example 4RH-4ET-15.8 12.4 Blue 23

[0341] As shown in the above [Table 1], a device employing a compound according to the present invention as a host compound of a light-emitting layer in an organic light-emitting device can implement an organic light-emitting device with excellent quantum efficiency and lifespan characteristics at a low driving voltage compared to devices (Comparative Examples 1 to 4) employing a compound widely used in the past, which is in contrast to the characteristic structure of the compound according to the present invention.

[0342]

[0343] Examples 10 to 18: Manufacturing of organic light-emitting devices

[0344] The organic light-emitting device used in Examples 1 to 9 was manufactured in the same manner as in Examples 1 to 9, except that 0.5 wt% of the dopant compound TBD was additionally mixed into the light-emitting layer, and the light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.

[0345] [TBD]

[0346]

[0347]

[0348] Comparative examples 5 to 8

[0349] An organic light-emitting device for comparative example was manufactured in the same manner as the above-described example, except that [RH-1] to [RH-4] were used instead of the compound according to the present invention as a host compound in the device structure of the above-described example, and the luminescence characteristics of the organic light-emitting device were measured at 0.4 mA.

[0350]

[0351] Classification 1st Host 2nd Host Driving Voltage (V) External Quantum Efficiency (%) Luminescence Color Lifetime (T80) Example 10HT-1ET-14.5 17.7 Blue 159 Example 11HT-2ET-14.4 17.9 Blue 168 Example 12HT-3ET-14.1 18.6 Blue 195 Example 13HT-4ET-14.2 18.5 Blue 190 Example 14HT-5ET-14.0 18.8 Blue 200 Example 15HT-6ET-14.0 18.8 Blue 198 Example 16HT-7ET-14.2 18.2 Blue 185 Example 17HT-8ET-14.4 17.6 Blue 168 Example 18HT-9ET-14.3 17.5 Blue 166 Comparative Example 5RH-1ET-15.4 15.1 Blue 74 Comparative Example 6RH-2ET-15.7 15.1 Blue 68 Comparative Example 7RH-3ET-15.3 12.4 Blue 58 Comparative Example 8RH-4ET-15.8 12.1 Blue 23

[0352] As shown in the above [Table 2], a device employing a compound according to the present invention as a host compound of a light-emitting layer in an organic light-emitting device can implement an organic light-emitting device with excellent quantum efficiency and lifespan characteristics at a low driving voltage compared to devices (Comparative Examples 5 to 8) employing a compound widely used in the past, which is in contrast to the characteristic structure of the compound according to the present invention.

[0353] The present invention relates to an organic compound employed in a light-emitting layer in an organic light-emitting device and to an organic light-emitting device comprising the same. When the compound according to the present invention is employed as a host in the light-emitting layer, a high-efficiency, long-life organic light-emitting device having low-voltage operation and significantly improved light-emitting efficiency and lifespan can be realized, and thus can be industrially usefully utilized in various display devices such as lighting devices, flat panel displays, flexible displays, and wearable displays. < / g-1> < / g-1> < / h-1a> < / g-1> < / g-1a> < / a-3> < / f-1> < / f-1a> < / e-3> < / e-3> < / e-2> < / a-2a> < / e-1> < / a-1b> < / c-1> < / d-3> < / d-2> < / a-2a> < / d-1> < / c-1b> < / d-1a> < / c-3> < / c-2> < / a-2a> < / c-1> < / c-1b> < / c-1a> < / b-2> < / b-3> < / b-1b> < / b-1b> < / b-1a> < / b-1> < / a-3> < / b-1a> < / a-5> < / a-5> < / a-2b> < / a-2b> < / a-4a> < / a-3> < / a-4> < / a-3> < / a-3a> < / a-2> < / a-1> < / a-2a> < / a-1> < / a-1b> < / a-1b> < / a-1a>

Claims

1. An organic compound represented by the following [chemical formula 1]: [Chemical Formula 1] In the above [chemical formula 1], R1 to R8 are the same or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms, a fused ring group of an aromatic ring having 5 to 30 carbon atoms, and any one selected from the following [structural formula b] to [structural formula f], [Structural formula b] [Structural formula c] [Structural formula d] [Structural formula e] [Structural formula f] At least one of the above R1 to R8 is one selected from the above [structural formula b] to [structural formula f], R9 to R above 11 At least one of them is [structural formula a], and the rest are the same or different from each other, and each is independently selected from hydrogen and deuterium, [Structural formula a] In the above [structural formula a] to [structural formula f], R 12 Inland R 14 are the same or different from each other, and each independently represents any one selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a fused ring group of a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 5 to 30 carbon atoms, L1 is any one selected from O, S, a substituted or unsubstituted arylene group, and a substituted or unsubstituted heteroarylene group, m is an integer from 1 to 3, and when m is 2 or more, multiple L1s are identical or different from each other, * in [structural formula a] is R9 to R 11 is a position where it binds to any one of R1 to R8, and * in [structural formula b] is a position where it binds to any one of R1 to R8, Y are identical or different and each independently CR 18 or N, and X is NR 19 , O, S, and SiR 20 R 21 One of the following is selected: Z is NR 22 , one of O and S, However, (i) X of the above [structural formula d] is NR 19 and Y is CR 18 In this case, L1 of the above [structural formula a] is O or S, and (ii) X of the above [structural formula f] is NR 19 and Y is CR 18 and Z is NR 22 In this case, L1 of the above [structural formula a] is O or S, L2 is any one selected from a single bond, a substituted or unsubstituted aryl group having 3 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, n is an integer from 0 to 2, and when n is 2 or greater, multiple L2s are identical or different from each other. The above R 18 Inland R 22 At least one of them is connected to R1 to R8, and the rest are the same or different from each other, and each independently is any one selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a fused ring group of a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 5 to 30 carbon atoms, 'Substitution' in 'substituted or unsubstituted' means a deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 30 carbon atoms, an alkylaryl group having 7 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms or a heteroarylalkyl group having 2 to 30 carbon atoms, an aliphatic ring having 3 to 30 carbon atoms, a fused ring group of an aromatic ring having 5 to 30 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, It means being substituted with one or more identical or different substituents selected from the group consisting of an amine group having 0 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 1 to 24 carbon atoms, and an arylthionyl group having 6 to 24 carbon atoms, and at least one hydrogen in each substituent can be replaced with deuterium.

2. In paragraph 1, The above [chemical formula 1] is a compound characterized in that it is one selected from compounds represented by the following chemical formula:

3. In paragraph 1, An organic compound characterized in that at least one of the above R1 to R8 is one selected from the above [structural formula b] to [structural formula f], and the remaining R1 to R8 that are not selected are hydrogen or deuterium.

4. In paragraph 3, An organic compound characterized in that the above R2 or R7 is any one selected from [structural formula b] to [structural formula f].

5. In paragraph 3, An organic compound characterized in that the above R2 and R7 are any one selected from [structural formula b] to [structural formula f].

6. In paragraph 1, The above R 12 Inland R 14 An organic compound characterized in that each of the following groups is the same or different, and each independently represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

7. An organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode; The organic layer includes a light-emitting layer including a host and a dopant; An organic light-emitting device characterized in that the host comprises at least one organic compound represented by [chemical formula 1] according to the first clause.

8. In paragraph 7, An organic light-emitting device characterized in that the host is used by mixing or layering at least one other compound in addition to one organic compound represented by the above-mentioned [chemical formula 1].

9. In paragraph 8, An organic light-emitting device characterized in that the organic compound represented by [chemical formula 1] used in the above host is used in a blue phosphorescent host.

10. In paragraph 9, An organic light-emitting device characterized in that the above dopant comprises at least one organometallic compound.

11. In paragraph 10, An organic light-emitting device characterized in that a polycyclic ring compound represented by the following [chemical formula 3] is mixed or layered in addition to the above organometallic compound: [Chemical Formula 3] In the above [chemical formula 3], Y1 and Y2 are the same or different and are independently O, S, NR 27 , CR 28 R 29 , SiR 30 R 31 and GeR 32 R 33 One of the following is selected: A1 to A3 rings are the same or different from each other, and are each independently selected from a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocycle having 2 to 30 carbon atoms, a substituted or unsubstituted aliphatic heterocycle having 2 to 30 carbon atoms, and a ring in which a substituted or unsubstituted aliphatic ring having 3 to 24 carbon atoms and an aromatic ring having 5 to 24 carbon atoms are fused, The above R 27 Inland R 33 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 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 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a ring group in which a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms and an aromatic ring having 5 to 30 carbon atoms are fused, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms Any one selected from an alkylthioxy group, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a nitro group, a cyano group, and a halogen group, The above R 27 Inland R 33 can be connected to the above A1 to A3 rings to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, The above R 28 Wow R 29 , R 30 and R 31 and R 32 and R 33 Each of them can be linked to each other to form additional alicyclic or aromatic monocyclic or polycyclic rings, In the above [chemical formula 3], 'substitution' in 'substituted or unsubstituted' means deuterium, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, an alkylaryl group having 7 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroarylalkyl group having 2 to 30 carbon atoms, a ring group in which an aliphatic ring having 3 to 24 carbon atoms and an aromatic ring having 5 to 24 carbon atoms are fused, an alkoxy group having 1 to 24 carbon atoms, an alkyl group having 1 to 30 carbon atoms. It means being substituted with one or more substituents selected from the group consisting of an amine group, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, an arylthionyl group having 6 to 24 carbon atoms, a cyano group, a halogen group, a hydroxy group, and a nitro group, and in the case of two or more, they are the same or different, and at least one hydrogen in each substituent can be replaced with deuterium.

12. In paragraph 7, The organic light-emitting device is an organic light-emitting device used in any one of a flat panel display device; a flexible display device; a flat panel lighting device of a single color or white color; a flexible lighting device of a single color or white color; a vehicle display device; and a display device for virtual or augmented reality.

Images