Novel compound and organic light-emitting device containing the same

Abstract

The present specification provides compounds represented by Formula 1 and Formula 3 and organic light-emitting devices including the same. The compounds represented by Formula 1 and Formula 3 can achieve improved efficiency, low driving voltage, and / or improved lifespan characteristics in an organic light-emitting device.

Description

[0001] This application is a divisional application of an application with an application date of July 9, 2018, application number 201880023813.9, and invention name “Novel compounds and organic light-emitting devices containing the same” (PCT / KR2018 / 007760, entering the national phase date of October 8, 2019). Technical Field

[0002] This specification claims the priority of Korean Patent Application No. 10-2017-0086611 filed in the Korean Intellectual Property Office on July 7, 2017, and incorporates all the contents disclosed in the document of the Korean Patent Application as a part of this specification.

[0003] The present invention relates to a novel compound and an organic light-emitting device comprising the same. Background Art

[0004] Generally speaking, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light-emitting element using the organic light-emitting phenomenon generally has a structure including an anode and a cathode and an organic layer located between the anode and the cathode. Here, in order to improve the efficiency and stability of the organic light-emitting element, 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 transport layer, an electron injection layer, etc. For the structure of such an organic light-emitting element, 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 re-transition to the ground state, light is emitted.

[0005] There is a continuous demand for the development of new materials for organic light-emitting elements as described above. Summary of the invention

[0006] Technical issues

[0007] This specification describes a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

[0008] Problem Solving Methods

[0009] One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[0010] [Chemical formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] L is a direct bond, a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group,

[0014] R1 to R5 are each independently hydrogen, deuterium, halogen, nitrile, nitro, hydroxyl, carboxyl, ether, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio ( Alkyl thioxy), substituted or unsubstituted arylthio ( Aryl thioxy), substituted or unsubstituted alkylsulfonyl ( Alkyl sulfoxy), substituted or unsubstituted arylsulfonyl ( Aryl sulfoxy), substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boronyl, substituted or unsubstituted arylphosphino, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or NRR',

[0015] Except when all R1 to R5 are hydrogen,

[0016] R and R' are each independently hydrogen, deuterium, halogen, nitrile, nitro, hydroxyl, carboxyl, ether, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boronyl, substituted or unsubstituted arylphosphino, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0017] a to e are each independently an integer from 0 to 3,

[0018] When b to e are 1 or more, adjacent R2 and R3, R3 and R4, and R4 and R5 may be bonded to each other to form a ring.

[0019] When b to e are 2 or more, each adjacent group in R2 to R5 may independently combine with each other to form a ring.

[0020] In addition, one embodiment of the present specification provides an organic light-emitting element, which includes: a first electrode, a second electrode, and one or more organic layers arranged between the first electrode and the second electrode, wherein one or more of the organic layers includes the compound of Chemical Formula 1.

[0021] Effects of the Invention

[0022] The compounds described in this specification can be used as materials for the organic layer of an organic light-emitting element. The compounds according to at least one embodiment can achieve improved efficiency, low driving voltage and / or improved life characteristics in an organic light-emitting element. In particular, the compounds described in this specification can be used as materials for the light-emitting layer.

[0023] More specifically, the compound according to one embodiment of the present invention has a structure with high electron storage capacity and excellent heat resistance, so that it is possible to maintain an appropriate vapor deposition temperature when manufacturing an organic light-emitting element. In addition, due to the high sublimation temperature, high purity can be achieved by a sublimation purification method, and no contamination is caused to the vapor deposition film forming device or the organic light-emitting element when manufacturing the organic light-emitting element. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Figure 1 The diagram shows an example of an organic light-emitting element composed of a substrate 1 , an anode 2 , a light-emitting layer 3 , and a cathode 4 .

[0025] Figure 2 The diagram shows an example of an organic light-emitting element composed of a substrate 1 , an anode 2 , a hole injection layer 5 , a hole transport layer 6 , a light-emitting layer 3 , an electron transport layer 7 , and a cathode 4 . DETAILED DESCRIPTION

[0026] Next, this specification is described in more detail.

[0027] One embodiment of the present specification provides a compound represented by the above Chemical Formula 1.

[0028] Examples of the above substituents are described below, but are not limited thereto.

[0029] In this specification, the term "substituted or unsubstituted" means that the group is substituted or unsubstituted by one or more substituents selected from deuterium, halogen groups, nitrile groups, nitro groups, hydroxyl groups, carbonyl groups, ester groups, imide groups, amino groups, phosphine oxide groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkylsulfonyl groups, arylsulfonyl groups, silyl groups, boron groups, alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, aralkyl groups, aralkenyl groups, alkylaryl groups, alkylamino groups, aralkylamino groups, heteroarylamino groups, arylamino groups, arylphosphino groups, and heterocyclic groups, or is substituted or unsubstituted by substituents formed by connecting two or more substituents among the substituents exemplified above. For example, "substituents formed by connecting two or more substituents" can be biphenyl groups. That is, the biphenyl group can be an aryl group, and can also be interpreted as a substituent formed by connecting two phenyl groups.

[0030] In this specification, "adjacent" groups refer to substituents substituted on atoms directly connected to the atom substituted by the substituent, the substituent closest to the substituent in the 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. Alternatively, a substituent substituted on the N of carbazole and a substituent on the 1st or 8th carbon of carbazole can be interpreted as "adjacent groups".

[0031] In this specification, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

[0032] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably the number of carbon atoms is 1 to 40. Specifically, it may be a compound having the following structure, but is not limited thereto.

[0033]

[0034] In this specification, in the ester group, the oxygen of the ester group may be substituted by a linear, branched, or cyclic alkyl group having 1 to 40 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound having the following structural formula, but is not limited thereto.

[0035]

[0036] In this specification, the number of carbon atoms in the imide group is not particularly limited, but preferably the number of carbon atoms is 1 to 25. Specifically, it may be a compound having the following structure, but is not limited thereto.

[0037]

[0038] In this specification, the silyl group may be represented by the chemical formula -SiR a R b R c In the above, R a 、R b and R c may each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the above silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

[0039] In this specification, the boron group may be represented by the chemical formula -BR a R b In the above, R a and R bThey may be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. Specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc., but are not limited thereto.

[0040] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, and 5-methylhexyl.

[0041] In this specification, the alkoxy group may be straight chain, branched chain or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably the number of carbon atoms is 1 to 40. Specifically, it may be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentyl group, a n-hexyl group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, a n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

[0042] The alkyl group, alkoxy group, and other substituents containing an alkyl portion described in the present specification include both linear and branched forms.

[0043] 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 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0044] In the present specification, the cycloalkyl group is not particularly limited, but preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 40 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. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0045] In the present specification, the number of carbon atoms in the alkylamino group is not particularly limited, but is preferably 1 to 40. Specific examples of the alkylamino group include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthracenylamino, 9-methylanthrylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenylbenzylamino, and the like, but are not limited thereto.

[0046] In this specification, examples of arylamine groups include substituted or unsubstituted monoarylamine groups or substituted or unsubstituted diarylamine groups. The aryl group in the above arylamine groups may be a monocyclic aryl group or a polycyclic aryl group. The above arylamine groups containing two or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group.

[0047] Specific examples of the arylamino group include phenylamino, naphthylamino, biphenylamino, anthracenylamino, 3-methyl-phenylamino, 4-methyl-naphthylamino, 2-methyl-biphenylamino, 9-methyl-anthrylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenyltolylamino, etc., but are not limited to these.

[0048] In this specification, as an example of heteroarylamine, there are substituted or unsubstituted monoheteroarylamine, or substituted or unsubstituted diheteroarylamine. The heteroaryl in the above heteroarylamine can be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The above heteroarylamine containing two or more heterocyclic groups can contain a monocyclic heterocyclic group, a polycyclic heterocyclic group, or can contain a monocyclic heterocyclic group and a polycyclic heterocyclic group at the same time.

[0049] In the present specification, the arylheteroarylamine group refers to an amine group substituted with an aryl group and a heterocyclic group.

[0050] In this specification, examples of arylphosphino include substituted or unsubstituted monoarylphosphino, substituted or unsubstituted diarylphosphino, or substituted or unsubstituted triarylphosphino. The aryl group in the above arylphosphino may be a monocyclic aryl group or a polycyclic aryl group. The above arylphosphino containing two or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group.

[0051] In the present 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 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, yl, fluorenyl, etc., but are not limited to these.

[0052] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

[0053] When the above fluorenyl group is substituted, it can be Spirofluorenyl, (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl) and the like substituted fluorenyl, but the present invention is not limited thereto.

[0054] In the present specification, the heterocyclic group is a heterocyclic group containing one or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 1 to 60. According to one embodiment, the number of carbon atoms in the heterocyclic group is 1 to 30. Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, Azolyl, iso Azolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, Azine, thiazine, di Inkyl, triazine, tetrazine, quinoline Isoquinolyl, quinolyl Quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl naphthyridinyl, triazaindenyl, indolyl, indolyl, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, benzothiazolyl, benzo oxazolyl, benzimidazolyl, benzothiophenyl, benzofuranyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolecarbazolyl, indenocarbazolyl, phenazine, imidazopyridyl, phen Oxazine, phenanthridinyl The moiety includes, but is not limited to, phenanthroline, phenothiazine, imidazopyridinyl, imidazophenanthridinyl and the like.

[0055] In the present specification, the number of atoms constituting the ring of the heterocyclic group is 3 to 25. In another embodiment, the number of atoms constituting the ring of the heterocyclic group is 5 to 17.

[0056] In the present specification, a heteroaryl group is aromatic, and other than this, the above description about the heterocyclic group is applicable.

[0057] In the present specification, the above description on the aryl group can be applied to the aryl group in the aryloxy group, arylthio group, arylsulfonyl group, arylphosphino group, arylalkyl group, arylalkylamino group, arylalkenyl group, alkylaryl group, arylamino group and arylheteroarylamino group.

[0058] In the present specification, the above description on the alkyl group can be applied to the alkyl group in the alkylthio group, alkylsulfonyl group, aralkyl group, aralkylamino group, alkylaryl group and alkylamino group.

[0059] In the present specification, the above description on the heterocyclic group can be applied to the heteroaryl group, the heteroarylamino group and the heteroaryl group in the arylheteroarylamino group.

[0060] In the present specification, the above description on the alkenyl group can be applied to the alkenyl group in the arylalkenyl group.

[0061] In the present specification, an arylene group is a divalent group, and other than this, the above description about the aryl group is applicable.

[0062] In the present specification, the heteroarylene group is a divalent group, and other than this, the above description about the heterocyclic group is applicable.

[0063] In the present specification, adjacent groups bonded to form a ring means that adjacent groups bonded to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic heterocycle, or a condensed ring thereof.

[0064] In this specification, an aliphatic hydrocarbon ring refers to a non-aromatic ring, which is formed only of carbon atoms and hydrogen atoms. Specifically, examples of aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc., but are not limited thereto.

[0065] In this specification, an aromatic hydrocarbon ring refers to an aromatic ring composed only of carbon atoms and hydrogen atoms. Specifically, examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenanthene, pyrene, tetracene, Pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, etc., but not limited to them.

[0066] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Specifically, examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dihydrofuran, In the present specification, an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms. Specifically, examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, Azoles, Isopropylamine Azoles, thiazoles, isothiazoles, triazoles, diazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazines, Azine, thiazine, di Indole, triazine, tetrazine, isoquinoline, quinoline, quinol, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, naphthyridine, triazaindene, indole, indolizine, benzothiazole, benzo azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phen Oxazine, phenanthridine, indolecarbazole, indenocarbazole, etc., but are not limited to these.

[0067] In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocyclic ring and aromatic heterocyclic ring may be monocyclic or polycyclic.

[0068] According to one embodiment of the present specification, the compound represented by the above Chemical Formula 1 may be represented by the following Chemical Formula 2 or Chemical Formula 3.

[0069] [Chemical formula 2]

[0070]

[0071] [Chemical formula 3]

[0072]

[0073] In the above chemical formulas 2 and 3,

[0074] R1a and R1b are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted silyl, or NRR',

[0075] f is 0 to 6,

[0076] g is 0 to 3,

[0077] R2 to R5, R, R′, and b to e are the same as defined in Chemical Formula 1.

[0078] In one embodiment of the present invention, L is a direct bond, an alkylene group having 1 to 60 carbon atoms, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

[0079] In one embodiment of the present invention, L is a direct bond, an alkylene group having 1 to 30 carbon atoms, or a monocyclic or polycyclic substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0080] In one embodiment of the present invention, L is a direct bond, or a monocyclic or polycyclic substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0081] In one embodiment of the present invention, L is a direct bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted quaterphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted pyrenylene, or a substituted or unsubstituted fluorenylene.

[0082] In the present specification, L's are the same or different and are each independently preferably a direct bond or any substituent selected from the following groups, but are not limited thereto. The following structures may be further substituted.

[0083]

[0084] In another embodiment, L is a direct bond, and R1 to R5 are each independently hydrogen, deuterium, halogen, nitrile, nitro, hydroxyl, carboxyl, ether, ester, imide, amide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted arylphosphine, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or NRR'.

[0085] In another embodiment, R1 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or NRR'.

[0086] In another embodiment, R1 is hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 60 carbon atoms, substituted or unsubstituted aryl having 6 to 60 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms, or NRR'.

[0087] In another embodiment, R1 is hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, or NRR'.

[0088] In another embodiment, R1 is hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 15 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms, or NRR'.

[0089] In addition, according to one embodiment of the present specification, R2 to R5 are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or NRR'.

[0090] In another embodiment, R2 to R5 are hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 60 carbon atoms, substituted or unsubstituted aryl having 6 to 60 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms, or NRR'.

[0091] In another embodiment, R2 to R5 are hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, or NRR'.

[0092] In another embodiment, R2 to R5 are hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 15 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 20 carbon atoms, or NRR'.

[0093] In addition, in one embodiment of the present specification, when b to e is 1 or more, adjacent R2 and R3, R3 and R4, and R4 and R5 can be combined with each other to form a ring, and when b to e is 2 or more, each adjacent group in R2 to R5 can be combined with each other to form a ring.

[0094] In addition, in one embodiment of the present specification, when b to e is 1 or more, adjacent R2 and R3, R3 and R4, and R4 and R5 can be combined with each other to form a substituted or unsubstituted ring with 3 to 60 carbon atoms, and when b to e is 2 or more, each adjacent group in R2 to R5 can be combined with each other to form a substituted or unsubstituted ring with 3 to 60 carbon atoms.

[0095] In addition, in one embodiment of the present specification, when b to e is 1 or more, adjacent R2 and R3, R3 and R4, and R4 and R5 can be combined with each other to form a substituted or unsubstituted ring with 3 to 30 carbon atoms, and when b to e is 2 or more, each adjacent group in R2 to R5 can be combined with each other to form a substituted or unsubstituted ring with 3 to 30 carbon atoms.

[0096] In addition, according to one embodiment of the present specification, except for the case where all of R1 to R5 are hydrogen, at least one of R1 to R5 must include a substituent other than hydrogen among the substituents described above.

[0097] In addition, according to one embodiment of the present specification, R and R' are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0098] In addition, according to one embodiment of the present specification, R and R' are each independently hydrogen, deuterium, 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 aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0099] In addition, according to one embodiment of the present specification, R and R' are each independently hydrogen, deuterium, 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 aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0100] In addition, according to one embodiment of the present specification, R and R' are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0101] In addition, according to one embodiment of the present specification, R and R' are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0102] In addition, according to one embodiment of the present specification, R and R' are each independently a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0103] In one embodiment of the present invention, the compound of the above Chemical Formula 1 may be any one selected from the following compounds.

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117] In the present invention, as described above, various substituents are introduced into the parent core structure, so that compounds with various energy gaps can be synthesized. It is usually easy to introduce substituents into the parent core structure with a large energy gap to adjust the energy gap, but it is difficult to introduce substituents when the energy gap of the parent core structure is small and adjust the energy gap to be larger. In addition, in the present invention, various substituents are introduced into the parent core structure of the structure as described above, so that the HOMO and LUMO energy levels of the compound can also be adjusted.

[0118] In addition, by introducing various substituents into the core structure of the structure described above, compounds having the inherent characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light-emitting layer materials, and electron transport layer materials used in the production of organic light-emitting elements into the core structure described above, substances that meet the conditions required for each organic layer can be synthesized.

[0119] Therefore, the present inventors have found that when the compound of Chemical Formula 1 having such characteristics is applied to materials for organic light-emitting devices, especially light-emitting layers, a lower driving voltage or a longer life can be achieved. 4 Compared with materials with a small molecular weight and high sublimation properties such as TCNQ, it is easier to vapor-deposit and can form a stable interface with an electrode or an adjacent organic layer.

[0120] The compound of the above Chemical Formula 1 can be prepared using materials and reaction conditions known in the art.

[0121] Furthermore, the organic light emitting element according to the present invention is characterized by comprising: a first electrode, a second electrode, and one or more organic layers arranged between the first electrode and the second electrode, and one or more of the organic layers contains the compound.

[0122] The organic light-emitting device of the present invention can be manufactured using the above-mentioned compound to form one or more organic layers, and can also be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0123] The organic layer of the organic light-emitting element of the present specification may be formed by a single-layer structure, or may be formed by a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present specification may have a structure that includes at least one of a hole injection layer, a hole buffer layer, a hole transport layer, an electron suppression layer, a hole suppression layer, an electron transport layer, and an electron injection layer as an organic layer in addition to the light-emitting layer. However, the structure of the organic light-emitting element is not limited thereto, and may include a smaller number of organic layers.

[0124] According to one example, the organic light emitting element may be an organic light emitting element having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. According to another example, the organic light emitting element may be an organic light emitting element having an inverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0125] The organic light-emitting element of the present specification can be manufactured using materials and methods known in the technical field, except that at least one layer of the organic layer contains the compound of Chemical Formula 1, that is, the compound represented by Chemical Formula 1.

[0126] For example, the organic light-emitting element of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, it can be manufactured as follows: a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation is used to vapor-deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting element can also be manufactured by sequentially vapor-depositing a cathode substance, an organic layer, and an anode substance on a substrate.

[0127] In addition, the compound of the above chemical formula 1 can be used not only by vacuum evaporation method but also by solution coating method to form an organic layer when manufacturing an organic light-emitting element. Here, the so-called solution coating method refers to spin coating method, dip coating method, blade coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited to these.

[0128] In addition to this method, an organic light emitting element can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (International Patent Application Publication No. 2003 / 012890). However, the manufacturing method is not limited to this.

[0129] In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

[0130] In another embodiment, the first electrode is a cathode, and the second electrode is an anode.

[0131] The organic light emitting element may have a stacked structure as described below, for example, but is not limited thereto.

[0132] (1) Anode / hole transport layer / light-emitting layer / cathode

[0133] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0134] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0135] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0136] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0137] (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0138] (7) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0139] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0140] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0141] (10) Anode / hole transport layer / electron suppression layer / light-emitting layer / electron transport layer / cathode

[0142] (11) Anode / hole transport layer / electron suppression layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0143] (12) Anode / hole injection layer / hole transport layer / electron suppression layer / light-emitting layer / electron transport layer / cathode

[0144] (13) Anode / hole injection layer / hole transport layer / electron suppression layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0145] (14) Anode / hole transport layer / light-emitting layer / hole suppression layer / electron transport layer / cathode

[0146] (15) Anode / hole transport layer / light-emitting layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0147] (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole suppression layer / electron transport layer / cathode

[0148] (17) Anode / hole injection layer / hole transport layer / light-emitting layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0149] For example, the structure of an organic light-emitting element according to one embodiment of the present specification is shown in Figure 1 and Figure 2 middle.

[0150] Figure 1 The figure shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a hole transport layer 6, a light emitting layer 3, and a cathode 4. In this structure, the above compound may be contained in the above light emitting layer.

[0151] Figure 2 The figure shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4. In this structure, the above compound may be contained in the above light emitting layer.

[0152] The anode 2, as an electrode for injecting holes, may be any one of ITO (Indium Tin Oxide), IZO (Indium Zinc Oxide) or ZnO (Zinc Oxide) having a large work function. In addition, when the anode 2 is a reflective electrode, the anode 2 may further include a reflective layer composed of any one selected from aluminum (Al), silver (Ag) or nickel (Ni) under the layer composed of any one selected from ITO, IZO or ZnO.

[0153] The hole injection layer 5 can play a role in enabling holes to be smoothly injected from the anode 2 to the light-emitting layer 3. The hole injection layer 5 may contain the compound of the above chemical formula 1. In this case, the hole injection layer 5 may be composed only of the compound of the above chemical formula 1, but the compound of the above chemical formula 1 may exist in a state of being mixed or doped with other hole injection layer materials known in the technical field. The compound of the above chemical formula 1 may occupy 100% of the hole injection layer, but may also be doped at 0.1 to 50 weight %. The compound of the above chemical formula 1 has excellent electron transport ability, so it can improve power consumption. And reduce the driving voltage. The thickness of the hole injection layer 5 can be 1nm to 150nm. Here, when the thickness of the above-mentioned hole injection layer 5 is more than 1nm, it has the advantage of preventing the hole injection characteristics from being reduced. When it is less than 150nm, it has the advantage of preventing the following problems: the above-mentioned problem is that the thickness of the hole injection layer 5 is too thick, so that the driving voltage rises in order to improve the movement of holes. In addition, as a hole injection layer material, a hole injection material known in the technical field can be used. For example, as a hole injection layer material, any one or more selected from CuPc (copperphthalocyanine), PEDOT (poly (3,4) -ethylenedioxythiophene), PANI (polyaniline) and NPD (N, N-dinaphthyl-N, N'-diphenyl benzidine) can be used, but it is not limited to this.

[0154] The hole transport layer 6 can play a role in smoothing the transport of holes. In the hole transport layer 6, other hole transport layer materials known in the technical field can exist alone, mixed or doped. The compound of the above chemical formula 1 can occupy 100% of the hole transport layer, but can also be doped at 0.1 to 50 weight%. In addition, as the hole transport layer material, a hole transport material known in the technical field can be used. For example, the hole transport layer 6 may be composed of any one or more selected from NPD (N,N-dinaphthyl-N,N'-diphenylbenzidine), TPD (N,N'-bis-(3-methylphenyl)-N,N'-bis-(phenyl)-benzidine), s-TAD and MTDATA (4,4',4"-tris(N-3-methylphenyl-N-phenyl-amino)-triphenylamine), but is not limited thereto. For example, as hole transport layer materials, triazole derivatives, Oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, aromatic amine derivatives, amino-substituted chalcone derivatives, Azole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, polysilane-based and aniline-based copolymers, conductive high molecular oligomers (especially thiophene oligomers), etc.

[0155] A hole buffer layer may be further provided between the hole injection layer and the hole transport layer. The hole buffer layer may include the compound of the above chemical formula 1, and in addition, may include a hole injection or transport material known in the technical field. When the hole buffer layer includes the compound of the above chemical formula 1, it may also be composed of only the compound of the above chemical formula 1, but it may also be composed of a state in which the compound of the above chemical formula 1 is mixed or doped in other host materials.

[0156] An electron suppression layer may be provided between the hole transport layer and the light emitting layer, and the compound of the above Chemical Formula 1 or a material known in the technical field may be used.

[0157] The light-emitting layer 3 may emit red, green and / or blue light and may include the chemical formula 1 according to one embodiment of the present specification. In addition, it may be used together with a material having a triplet value of 2.5 eV or more. Specifically, it may include a material having ΔE ST A sensitizer having a TADF (delayed fluorescence) characteristic with a (difference between singlet energy and triplet energy) of less than 0.2 eV (limited to a substance having a triplet energy of 2.6 eV or more). Examples of substances having delayed fluorescence characteristics are as follows, but are not limited to these.

[0158]

[0159] A hole suppression layer may be provided between the electron transport layer and the light emitting layer, and a material known in the technical field may be used.

[0160] The electron transport layer 7 can play a role in smoothing the electron transport. 3 (tris(8-hydroxyquinolino)aluminum), PBD, TAZ, spiro PBD, BAlq, SAlq and other materials known in the art. The thickness of the electron transport layer 7 can be 1 to 50 nm. When the thickness of the electron transport layer 7 is greater than 1 nm, it has the advantage of preventing the electron transport characteristics from being reduced. When the thickness is less than 50 nm, it has the advantage of preventing the following problem: The above problem is that the thickness of the electron transport layer 7 is too thick, thereby increasing the driving voltage in order to increase the movement of electrons.

[0161] The electron injection layer can facilitate the injection of electrons. 3The metal compound may be an organic compound, a complex or a metal compound known in the art such as tris(8-hydroxyquinolino)aluminum, PBD, TAZ, spiro PBD, BAlq or SAlq. As the metal compound, a metal halide may be used, for example, LiQ, LiF, NaF, KF, RbF, CsF, FrF, BeF 2 MgF 2 , CaF 2 , SrF 2 , BaF 2 and RaF 2 The thickness of the electron injection layer may be 1 to 50 nm. When the thickness of the electron injection layer is 1 nm or more, it has the advantage of preventing the electron injection characteristics from being reduced, and when the thickness is 50 nm or less, it has the advantage of preventing the following problem: the above problem is that the thickness of the electron injection layer is too thick, thereby increasing the driving voltage in order to improve the movement of electrons.

[0162] The cathode 4 as an electron injection electrode can be made of magnesium (Mg), calcium (Ca), aluminum (Al), silver (Ag) or their alloys with a small work function. Here, when the organic electroluminescent element is a top or bidirectional light-emitting structure, the cathode 4 can be formed to be thin enough to transmit light, and when the organic electroluminescent element is a bottom light-emitting structure, it can be formed thick enough to reflect light.

[0163] According to another embodiment, between the light-emitting layer and the anode or cathode, and between the light-emitting layer and the charge generation layer, one or more organic layers such as the hole injection layer, hole buffer layer, hole transport layer, electron suppression layer, hole suppression layer, electron transport layer, and electron injection layer may be included. As an example of an organic light-emitting element, it includes: a substrate, an anode and a cathode, and between the anode and the cathode, there are two units, the units including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, and there is a charge generation layer between the units.

[0164] The organic light emitting element according to the present invention may be a top emission type, a bottom emission type or a bi-directional emission type according to the materials used.

[0165] The compound according to the present invention can also function in organic electronic devices such as organic solar cells, organic photoreceptors, and organic transistors based on a principle similar to that when applied to organic light-emitting devices.

[0166] Modes for Carrying Out the Invention

[0167] The method for producing the compound of the above Chemical Formula 1 and the production of an organic light-emitting device using the same are specifically described in the following examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.

[0168] <Production Example>

[0169] The method for producing the substance of the present invention is as follows, starting from the intermediate synthesis of introducing a halide using a substituted or unsubstituted aniline. The aryl group is introduced into the halide by the Suzuki reaction, and the amino group (-NH) is replaced by a bromide (-Br) by the Sandmeyer reaction. 2 Then, boron can be introduced by using butyl lithium and tribromoborane. In addition to the aniline species described in Preparation Example 1-1, aniline with various substituents introduced therein was used to synthesize the compounds of the specific examples by the following reaction.

[0170] Preparation Example 1-1: Synthesis of Compound 1-A

[0171] [Reaction formula 1-1]

[0172]

[0173] Under nitrogen atmosphere, the above compound 3,5-dimethylaniline (30 g, 0.25 mol) was completely dissolved in 300 mL of chloroform, and then bromine (79.2 g, 0.50 mol) was added at 0 degrees and stirred for 2 hours. The organic layer was extracted with 300 mL of 1 molar sodium thiosulfate solution, and then the organic layer was completely distilled and purified by column chromatography (chloroform / hexane), thereby producing the above compound 1-A (65.6 g, yield: 95%).

[0174] MS[M+H] + =277

[0175] Preparation Example 1-2: Synthesis of Compound 1-B

[0176] [Reaction 1-2]

[0177]

[0178] Under nitrogen atmosphere, the above compound 4-tert-butyl-aniline (37.3 g, 0.25 mol) was completely dissolved in 300 mL of chloroform, and then bromine (79.2 g, 0.50 mol) was added at 0 degrees and stirred for 2 hours. The organic layer was extracted with 300 mL of 1 molar sodium thiosulfate solution, and then the organic layer was completely distilled and purified by column chromatography (chloroform / hexane), thereby producing the above compound 1-B (70.6 g, yield: 92%).

[0179] MS[M+H] + =305

[0180] Preparation Example 1-3: Synthesis of Compound 1-C

[0181] [Reaction 1-3]

[0182]

[0183] Under nitrogen atmosphere, the above compound aniline (23.3 g, 0.25 mol) was completely dissolved in 300 mL of chloroform, and then bromine (79.2 g, 0.50 mol) was added at 0 degrees and stirred for 2 hours. The organic layer was extracted with 300 mL of 1 molar sodium thiosulfate solution, and then the organic layer was completely distilled and purified by column chromatography (chloroform / hexane), thereby producing the above compound 1-C (59.6 g, yield: 95%).

[0184] MS[M+H] + =249

[0185] Preparation Example 1-4: Synthesis of Compound 1-D

[0186] [Reaction 1-4]

[0187]

[0188] Under nitrogen atmosphere, the above compound 4-chloroaniline (31.9 g, 0.25 mol) was completely dissolved in 300 mL of chloroform, and then bromine (79.2 g, 0.50 mol) was added at 0 degrees and stirred for 2 hours. The organic layer was extracted with 300 mL of 1 molar sodium thiosulfate solution, and then the organic layer was completely distilled and purified by column chromatography (chloroform / hexane), thereby producing the above compound 1-D (67 g, yield: 94%).

[0189] MS[M+H] + =283

[0190] Preparation Example 2-1: Synthesis of Compound 2-A

[0191] [Reaction formula 2-1]

[0192]

[0193] Under nitrogen atmosphere, the above compound 1-A (61.4 g, 0.22 mol) was completely dissolved in 440 mL of tetrahydrofuran (THF), and then 130 mL of potassium carbonate aqueous solution (10 M) was added, and 1-naphthylboronic acid (75.7 g, 0.44 mol) was added. Tetrakis(triphenylphosphine)palladium (2.5 g, 2.2 mmol) was added, and refluxed and stirred for 3 hours. After the reaction was completed, the water layer was removed, and the organic layer was completely distilled and purified by column chromatography (chloroform / hexane), thereby producing the above compound 2-A (74 g, yield: 90%).

[0194] MS[M+H] + =374

[0195] Preparation Example 2-2: Synthesis of Compound 2-B

[0196] [Reaction formula 2-2]

[0197]

[0198] Under nitrogen atmosphere, the above compound 1-B (67.5 g, 0.22 mol) was completely dissolved in 440 mL of tetrahydrofuran, and then 130 mL of potassium carbonate aqueous solution (10 M) was added, and 1-naphthylboronic acid (75.7 g, 0.44 mol) was added. Tetrakis(triphenylphosphine)palladium (2.5 g, 2.2 mmol) was added, and refluxed for 3 hours. After the reaction was completed, the water layer was removed, and then the organic layer was completely distilled and purified by column chromatography (chloroform / hexane), thereby producing the above compound 2-B (77.7 g, yield: 88%).

[0199] MS[M+H] + =402

[0200] Preparation Example 2-3: Synthesis of Compound 2-C

[0201] [Reaction 2-3]

[0202]

[0203] Under nitrogen atmosphere, the above compound 1-C (55.2 g, 0.22 mol) was completely dissolved in 440 mL of tetrahydrofuran, and then 130 mL of potassium carbonate aqueous solution (10 M) was added, and fluoranthene-3-boric acid (108.3 g, 0.44 mol) was added. Tetrakis(triphenylphosphine)palladium (2.5 g, 2.2 mmol) was added, and refluxed and stirred for 3 hours. After the reaction was completed, the water layer was removed, and then the organic layer was completely distilled and purified by column chromatography (chloroform / hexane), thereby producing the above compound 2-C (92.3 g, yield: 85%).

[0204] MS[M+H] + =494

[0205] Preparation Example 2-4: Synthesis of Compound 2-D

[0206] [Reaction 2-4]

[0207]

[0208] Under nitrogen atmosphere, the above compound 1-D (62.7 g, 0.22 mol) was completely dissolved in 440 mL of tetrahydrofuran, and then 130 mL of potassium carbonate aqueous solution (10 M) was added, and 1-naphthylboronic acid (75.7 g, 0.44 mol) was added. Tetrakis(triphenylphosphine)palladium (2.5 g, 2.2 mmol) was added, and refluxed for 3 hours. After the reaction was completed, the water layer was removed, and then the organic layer was completely distilled and purified by column chromatography (chloroform / hexane), thereby producing the above compound 2-D (72.7 g, yield: 87%).

[0209] MS[M+H] + =380

[0210] Preparation Example 3-1: Synthesis of Compound 3-A

[0211] [Reaction formula 3-1]

[0212]

[0213] Under nitrogen atmosphere, 1.8 L of acetonitrile was added to the above compound 2-A (67.2 g, 0.18 mol), and 45 mL of 12 M hydrochloric acid was added at 0 degrees. After adding sodium nitrite (18.6 g, 0.27 mol) at 0 degrees, stirring was carried out for 10 minutes, copper bromide (II) (60.3 g, 0.27 mol) was added, and heated to 50 degrees. After heating for 1 hour, reverse precipitation was carried out in 2 L of distilled water to obtain a solid. The obtained solid was purified by column chromatography (chloroform / hexane) to produce the above compound 3-A (59 g, yield: 75%).

[0214] MS[M+H] + =437

[0215] Preparation Example 3-2: Synthesis of Compound 3-B

[0216] [Reaction formula 3-2]

[0217]

[0218] Under nitrogen atmosphere, 1.8 L of acetonitrile was added to the above compound 2-B (72.3 g, 0.18 mol), and 45 mL of 12 M hydrochloric acid was added at 0 degrees. After adding sodium nitrite (18.6 g, 0.27 mol) at 0 degrees, stirring was carried out for 10 minutes, copper bromide (II) (60.3 g, 0.27 mol) was added, and heated to 50 degrees. After heating for 1 hour, reverse precipitation was carried out in 2 L of distilled water to obtain a solid. The obtained solid was purified by column chromatography (chloroform / hexane) to produce the above compound 3-B (64.5 g, yield: 77%).

[0219] MS[M+H] + =465

[0220] Preparation Example 3-3: Synthesis of Compound 3-C

[0221] [Reaction formula 3-3]

[0222]

[0223] Under nitrogen atmosphere, 1.8 L of acetonitrile was added to the above compound 2-C (88.8 g, 0.18 mol), and 45 mL of 12 M hydrochloric acid was added at 0 degrees. After adding sodium nitrite (18.6 g, 0.27 mol) at 0 degrees, stirring was carried out for 10 minutes, copper bromide (II) (60.3 g, 0.27 mol) was added, and heated to 50 degrees. After heating for 1 hour, reverse precipitation was carried out in 2 L of distilled water to obtain a solid. The obtained solid was purified by column chromatography (chloroform / hexane) to produce the above compound 3-C (76.3 g, yield: 76%).

[0224] MS[M+H] + =557

[0225] Preparation Example 3-4: Synthesis of Compound 3-D

[0226] [Reaction 3-4]

[0227]

[0228] Under nitrogen atmosphere, 1.8 L of acetonitrile was added to the above compound 2-D (68.4 g, 0.18 mol), and 45 mL of 12 M hydrochloric acid was added at 0 degrees. After adding sodium nitrite (18.6 g, 0.27 mol) at 0 degrees, stirring was carried out for 10 minutes, copper bromide (II) (60.3 g, 0.27 mol) was added, and heating was carried out to 50 degrees. After heating for 1 hour, reverse precipitation was carried out in 2 L of distilled water to obtain a solid. The obtained solid was purified by column chromatography (chloroform / hexane) to produce the above compound 3-D (59.9 g, yield: 75%).

[0229] MS[M+H]+ =443

[0230] Preparation Example 4-1: Synthesis of Compound 3

[0231] [Reaction 4-1]

[0232]

[0233] Under nitrogen atmosphere, 200 ml of toluene was added to the above compound 3-A (21.8 g, 0.05 mol), and 20 mL of 2.5 M n-butyl lithium was added at -78 degrees. After stirring at -78 degrees for 2 hours, tribromoborane (25 g, 0.1 mol) was added at -78 degrees and stirred for 30 minutes. The temperature was raised to room temperature, stirred for 30 minutes, and then stirred at 50 degrees for 1 hour. After cooling to 0 degrees, diisopropylethylamine (12.9 g, 0.1 mol) was added and refluxed for 20 hours. After further adding diisopropylethylamine (6.5 g, 0.05 ml) at room temperature, the solvent was completely distilled and purified by column chromatography (chloroform / hexane), thereby producing the above compound 3 (11.5 g, yield: 63%).

[0234] MS[M+H] + =367

[0235] Preparation Example 4-2: Synthesis of Compound 2

[0236] [Reaction 4-2]

[0237]

[0238] Under nitrogen atmosphere, 200 ml of toluene was added to the above compound 3-B (23.3 g, 0.05 mol), and 20 mL of 2.5 M n-butyl lithium was added at -78 degrees. After stirring at -78 degrees for 2 hours, tribromoborane (25 g, 0.1 mol) was added at -78 degrees and stirred for 30 minutes. The temperature was raised to room temperature, stirred for 30 minutes, and then stirred at 50 degrees for 1 hour. After cooling to 0 degrees, diisopropylethylamine (12.9 g, 0.1 mol) was added and refluxed for 20 hours. After further adding diisopropylethylamine (6.5 g, 0.05 ml) at room temperature, the solvent was completely distilled and purified by column chromatography (chloroform / hexane), thereby producing the above compound 2 (12.8 g, yield: 65%).

[0239] MS[M+H] + =395

[0240] Preparation Example 4-3: Synthesis of Compound 214

[0241] [Reaction 4-3]

[0242]

[0243] Under nitrogen atmosphere, 200 ml of toluene was added to the above compound 3-C (27.8 g, 0.05 mol), and 20 mL of 2.5 M n-butyl lithium was added at -78 degrees. After stirring at -78 degrees for 2 hours, tribromoborane (25 g, 0.1 mol) was added at -78 degrees and stirred for 30 minutes. The temperature was raised to room temperature, stirred for 30 minutes, and then stirred at 50 degrees for 1 hour. After cooling to 0 degrees, diisopropylethylamine (12.9 g, 0.1 mol) was added and refluxed for 20 hours. After further adding diisopropylethylamine (6.5 g, 0.05 ml) at room temperature, the solvent was completely distilled and purified by column chromatography (chloroform / hexane), thereby producing the above compound 214 (15.1 g, yield: 62%).

[0244] MS[M+H] + =487

[0245] Preparation Example 4-4: Synthesis of Compound 4-D

[0246] [Reaction formula 4-4]

[0247]

[0248] Under nitrogen atmosphere, 200 ml of toluene was added to the above compound 3-D (22.2 g, 0.05 mol), and 20 mL of 2.5 M n-butyl lithium was added at -78 degrees. After stirring at -78 degrees for 2 hours, tribromoborane (25 g, 0.1 mol) was added at -78 degrees and stirred for 30 minutes. The temperature was raised to room temperature, stirred for 30 minutes, and then stirred at 50 degrees for 1 hour. After cooling to 0 degrees, diisopropylethylamine (12.9 g, 0.1 mol) was added and refluxed for 20 hours. After further adding diisopropylethylamine (6.5 g, 0.05 ml) at room temperature, the solvent was completely distilled and purified by column chromatography (chloroform / hexane), thereby producing the above compound 4-D (18.6 g, yield: 66%).

[0249] MS[M+H] + =373

[0250] Preparation Example 5-1: Synthesis of Compound 191

[0251] [Reaction formula 5-1]

[0252]

[0253] Under nitrogen atmosphere, 30 ml of toluene, diphenylamine (1.7 g, 0.01 mol) and sodium tert-butoxide (1.9 g, 0.02 mol) were added to the above compound 4-D (3.7 g, 0.01 mol). Tetrakis(triphenylphosphine)palladium (58 mg, 0.05 mmol) was added, and the mixture was refluxed and stirred for 2 hours. After the organic layer was extracted with water, the solvent was completely distilled and purified by column chromatography (chloroform / hexane), thereby producing the above compound 191 (4.7 g, yield: 93%).

[0254] MS[M+H] + =506

[0255] Preparation Example 5-2: Synthesis of Compound 5-D

[0256] [Reaction formula 5-2]

[0257]

[0258] Under nitrogen atmosphere, 140 ml of 1,4-dihydroquinone was added to the above compound 4-D (14.9 g, 0.04 mol). alkane, potassium acetate (7.9 g, 0.08 mol) and bis(pinacolato)diboron (10.2 g, 0.04 mol) were added. Palladium acetate (90 mg, 0.4 mmol) was further added and refluxed for 12 hours. After the reaction was completed, the organic layer was extracted with water, the solvent was completely distilled off, and purified by column chromatography (chloroform / hexane) to produce the above-mentioned compound 5-D (17.3 g, yield: 93%).

[0259] MS[M+H] + =465

[0260] Preparation Example 5-3: Synthesis of Compound 31

[0261] [Reaction 5-3]

[0262]

[0263] Under nitrogen atmosphere, the above compound 5-D (13.9 g, 0.03 mol) was completely dissolved in 30 mL of tetrahydrofuran, and then 10 mL of potassium carbonate aqueous solution (10 M) was added, and bromobenzene (4.8 g, 0.03 mol) was added. Tetrakis(triphenylphosphine)palladium (0.35 g, 0.3 mmol) was added, and the mixture was refluxed and stirred for 3 hours. After the reaction was completed, the aqueous layer was removed, and then the organic layer was completely distilled and purified by column chromatography (chloroform / hexane), thereby producing the above compound 31 (11.8 g, yield: 95%).

[0264] MS[M+H] +=415

[0265] <Example>

[0266] In this example, an organic photoluminescent element was manufactured and its characteristics were evaluated. The organic photoluminescent element comprises a host material (m-CBP) having a triplet value of 2.5 eV or more and a ΔE ST A sensitizer (4CzIPN) with TADF (delayed fluorescence) characteristics, where the difference between singlet energy and triplet energy is less than 0.2 eV.

[0267] (Experimental Example 1)

[0268] In this example, an organic electroluminescent element having a light-emitting layer composed of GD1, m-CBP, and 4CzIPN was manufactured and its characteristics were evaluated. A glass substrate coated with a thin film of thickness of ITO (indium tin oxide) is placed in distilled water dissolved with detergent and washed with ultrasound. At this time, the detergent used is a product of Fischer Co., and the distilled water used is distilled water filtered twice by a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, it is repeated twice with distilled water and ultrasonically washed for 10 minutes. After the distilled water washing is completed, ultrasonic washing is performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it is transported to a plasma cleaning machine. In addition, the above-mentioned substrate is cleaned for 5 minutes using oxygen plasma, and then the substrate is transported to a vacuum deposition machine. On the ITO transparent electrode prepared in this way, vacuum deposition is performed at a vacuum degree of 5.0×10 -4 Pa stacks each thin film. First, on ITO A hole injection layer was formed by thermal vacuum deposition of hexanitrilehexaazatriphenylene (HAT) to a thickness of 1000 Å.

[0269] The following compound 4-4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was vacuum deposited on the hole injection layer as a hole transporting substance. Thus, a hole transport layer is formed.

[0270] The hole transport layer has a film thickness of The following compound N-([1,1'-diphenyl]-4-yl)-N-(4-(11-([1,1'-biphenyl]-4-yl)-11H-benzo[a]carbazole-5-yl)phenyl)-[1,1'-biphenyl]-4-amine (EB1) was vacuum deposited An electron suppression layer is formed.

[0271] Next, a film having a thickness of m-CBP, 4CzIPN, and GD1 were vacuum deposited at a weight ratio of 68:30:2 to form a light-emitting layer.

[0272] Compound ET1 and compound LiQ (8-hydroxyquinoline lithium, Lithium Quinolate) were vacuum-deposited on the light-emitting layer at a weight ratio of 1:1, thereby The electron injection and transport layer is formed with a thickness of The thickness of the aluminum A cathode is formed by vapor deposition of a thickness of .

[0273] In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 2×10 -7 ~5×10 -6 A support is provided to produce an organic light-emitting element.

[0274]

[0275] Experimental Examples 1-1 to 1-48

[0276] An organic light-emitting device was produced by the same method as in Experimental Example 1 except that the compound shown in Table 1 below was used instead of Compound GD1.

[0277]

[0278] Comparative Experiment Example 1-1

[0279] An organic light-emitting device was produced by the same method as in Experimental Example 1 except that the following compound GD2 was used instead of the compound GD1.

[0280]

[0281] The voltage, efficiency, and emission wavelength were measured when current was applied to the organic light-emitting elements produced in Experimental Examples 1-1 to 1-38 and Comparative Example 1-1. The results are shown in Table 1 below.

[0282] [Table 1]

[0283]

[0284] As shown in Table 1, the devices of Experimental Examples 1-1 to 1-48 using the compound having the structure of Chemical Formula 1 as a core all achieved lower voltage and improved efficiency compared to the device of Experimental Example 1 using the compound GD1.

[0285] In addition, compared with the element of Comparative Example 1-1, it can be seen that the structure of the present Chemical Formula 1 having a substituent has improved characteristics in terms of voltage, efficiency and emission wavelength compared with the case without a substituent.

[0286] As shown in the results of Table 1, it was confirmed that the compound according to the present invention has excellent light-emitting ability and high color purity, and can be suitably used in an organic light-emitting element.

Claims

1. A compound represented by the following formula 1: Formula 1 In formula 1, L is a direct key, R2 to R5 are hydrogen, R1 is methyl, tert-butyl or -NRR', R and R' are each independently a phenyl group which is substituted or unsubstituted with a methyl group or a tert-butyl group, a is an integer from 0 to 3, but excluding 0 and 3, b to e are 1.

2. A compound represented by the following formula 2: Formula 2 In formula 2, R2 to R5 are hydrogen, R1a is methyl or tert-butyl, f is 0 to 5, b to e are 1.

3. A compound represented by the following formula 3: Formula 3 In formula 3, R1b is deuterium, methyl, tert-butyl, or trimethylsilyl, R2 to R5 are each independently hydrogen, deuterium, tert-butyl substituted or unsubstituted phenyl, or naphthyl, b to e are 1 to 3, At least one of R4 and R5 combines with the other R4 or R5 to form an indene ring, a benzene ring or a naphthalene ring, each of which is independently substituted with an unsubstituted or tert-butyl-substituted phenyl group or unsubstituted, and g is 0 to 3.

4. A compound selected from any one of the following structures:

5. An organic light emitting device, include: a first electrode; a second electrode; as well as One or more organic layers are disposed between the first electrode and the second electrode, The organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound according to any one of claims 1 to 4.

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