Organic Light Emitting Diodes

Abstract

The present application relates to an organic light-emitting device, including: a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode.

Description

Technical Field

[0001] The present invention claims the priority of Korean Patent Application No. 10-2018-0156860 filed in the Korean Intellectual Property Office on December 7, 2018, the entire contents of which are incorporated into this specification.

[0002] The present application relates to an organic light-emitting device, including: a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode. Background Art

[0003] Generally speaking, the phenomenon of organic light emitting refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light emitting device using the phenomenon of organic light emitting generally has a structure including an anode and a cathode and an organic layer located between them. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is mostly formed by a multilayer structure composed of different substances, for example, it can be formed by a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. For the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons re-transition to the ground state, light is emitted.

[0004] There is a continuous demand for the development of new materials for organic light-emitting devices as described above. Summary of the invention

[0005] Technical issues

[0006] This specification provides an organic light-emitting device.

[0007] Solution to the problem

[0008] The present specification provides an organic light-emitting device, which includes: an anode, a cathode disposed opposite to the anode, a light-emitting layer disposed between the anode and the cathode and containing a compound represented by the following chemical formula 1, a hole transport region disposed between the anode and the light-emitting layer, and an electron transport region disposed between the cathode and the light-emitting layer and containing a compound represented by the following chemical formula 2.

[0009] [Chemical formula 1]

[0010]

[0011] In Chemical Formula 1, A, B and C are each independently a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring, X1 and X2 are each independently O, CR1R2 or NR3, R1 to R3 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and adjacent groups among R1 to R3, A, B and C may be combined with each other to form a substituted or unsubstituted ring,

[0012] [Chemical formula 2]

[0013]

[0014] In Chemical Formula 2, two or more of X4 to X6 are N, and the rest are CH, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, L is a substituted or unsubstituted trivalent aryl group, or a substituted or unsubstituted trivalent heterocyclic group, Y is a substituted or unsubstituted polycyclic aryl group, and n is 2. When n is 2, the two Ys are the same or different from each other.

[0015] Effects of the Invention

[0016] An organic light-emitting device using the compound according to one embodiment of the present application can achieve low driving voltage, high light-emitting efficiency, and / or long lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0017] Figure 1 The diagram shows an example of an organic light-emitting device in which a substrate 1 , an anode 2 , a hole transport region 10 , a light-emitting layer 3 , an electron transport region 20 , and a cathode 4 are sequentially stacked.

[0018] Figure 2 The diagram shows an example of an organic light-emitting device in which a substrate 1 , an anode 2 , a hole injection layer 5 , a hole transport layer 6 , a light-emitting layer 3 , an electron regulation layer 7 , an electron injection and transport layer 8 , and a cathode 4 are sequentially stacked.

[0019] Figure 3 This is an MS spectrum of compound 2-1 according to one embodiment of the present specification.

[0020] Figure 4 It is an MS spectrum of compound 2-2 according to one embodiment of the present specification.

[0021] Figure 5 It is an MS spectrum of compound 2-3 according to one embodiment of the present specification.

[0022] Figure 6 It is an MS spectrum of compound 2-4 according to one embodiment of the present specification.

[0023] Figure 7 It is an MS spectrum of compound 2-5 according to one embodiment of the present specification.

[0024] Figure 8 It is an MS spectrum of compound 2-6 according to one embodiment of the present specification.

[0025] Fig. 9 It is an MS spectrum of compound 2-9 according to one embodiment of the present specification.

[0026] Fig.10 It is an MS spectrum of compound 2-10 according to one embodiment of the present specification.

[0027] Fig.11 It is an MS spectrum of compound 2-11 according to one embodiment of the present specification.

[0028] Fig.12 It is an MS spectrum of compound 2-12 according to one embodiment of the present specification.

[0029] Fig.13 It is an MS spectrum of compound 2-13 according to one embodiment of the present specification.

[0030] Fig.14 It is an MS spectrum of compound 2-16 according to one embodiment of the present specification.

[0031] Fig.15 It is an MS spectrum of compound 2-17 according to one embodiment of the present specification.

[0032] Fig.16 It is an MS spectrum of compound 2-20 according to one embodiment of the present specification.

[0033] Fig.17 It is an MS spectrum of compound 2-22 according to one embodiment of the present specification.

[0034] <Description of symbols>

[0035] 1: Substrate

[0036] 2: Anode

[0037] 3: Luminous layer

[0038] 4: Cathode

[0039] 5: Hole injection layer

[0040] 6: Hole transport layer

[0041] 7: Electronic adjustment layer

[0042] 8: Electron injection and transport layer

[0043] 10: Hole transport region

[0044] 20: Electron transport region DETAILED DESCRIPTION

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

[0046] The present specification provides an organic light-emitting device, which includes: a first electrode, a second electrode opposite to the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein the one or more organic layers respectively contain a compound represented by the following chemical formula 1 or a compound represented by chemical formula 2.

[0047] In the present application, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.

[0048] In the present application, when it is indicated that a certain part “includes / comprises” a certain constituent element, unless there is a particular description to the contrary, it means that other constituent elements may be further included, rather than excluding other constituent elements.

[0049] In the present specification, examples of substituents are described below, but are not limited thereto.

[0050] The term "substituted" mentioned above means that the hydrogen atom bonded to the carbon atom of the compound is replaced by another substituent. The substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.

[0051] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium, a halogen group, a cyano group, a nitro group, a carbonyl group, an ester group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group ( Alkyl thioxy), substituted or unsubstituted arylthio ( Aryl thioxy), substituted or unsubstituted alkylsulfonyl ( Alkyl sulfoxy), substituted or unsubstituted arylsulfonyl ( The present invention relates to a substituted or unsubstituted alkylene group, ...

[0052] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0053] In the present specification, the number of carbon atoms in the ester group is not particularly limited, but preferably the number of carbon atoms is 1 to 50. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.

[0054]

[0055] In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably the number of carbon atoms is 1 to 50. Specifically, the compound may have the following structure, but is not limited thereto.

[0056]

[0057] 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 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0058] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and specifically includes 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 and the like, but is not limited thereto.

[0059] 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 20. Specifically, there are methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but are not limited thereto.

[0060] In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0061] In the present specification, specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited thereto.

[0062] In this specification, the boron group can be -BR 100 R 101 , the above R 100 and R 101 The same or different groups may be independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted monocyclic or polycyclic cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted linear or branched alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms. Specifically, there are trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc., but the present invention is not limited thereto.

[0063] In the present specification, specific examples of the phosphine oxide group include a diphenylphosphine oxide group and a dinaphthylphosphine oxide group, but the present invention is not limited thereto.

[0064] In the present specification, the amine group can be selected from -NH2, alkylamine, N-alkylarylamine, arylamine, N-arylheteroarylamine, N-alkylheteroarylamine and heteroarylamine, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amino groups include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthracenylamino, 9-methyl-anthrylamino, diphenylamino, N-phenylnaphthylamino, xylylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrenylamino, N-biphenylphenanthrenylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrenylfluorenylamino, and N-biphenylfluorenylamino.

[0065] In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted on the N of the amine group.

[0066] In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group or a heteroaryl group is substituted on the N of the amine group.

[0067] In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted on the N of the amine group.

[0068] 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. For example, the aryl group in the above arylamine groups may be selected from the examples of the above aryl groups.

[0069] In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 6 to 25. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

[0070] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 10 to 24. Specifically, the polycyclic aryl group may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, yl, fluorenyl, etc., but are not limited to these.

[0071] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a substituted or unsubstituted ring.

[0072] When the fluorenyl group is substituted, it may be etc., but not limited thereto.

[0073] In the present specification, the heterocyclic group contains one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may contain one or more atoms selected from O, N, Se, S, etc. The number of carbon atoms in the heterocyclic group is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of the heterocyclic group include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridinyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, thiazolyl, isothiophene Azolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl and dibenzofuranyl, but are not limited thereto.

[0074] In the present specification, an aliphatic hydrocarbon ring is a divalent group, and other than this, the above description about the cycloalkyl group is applicable.

[0075] 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 and arylamine group.

[0076] In the present specification, the above description on the alkyl group can be applied to the alkyl group in the alkylthio group, the alkylsulfonyl group and the alkylamino group.

[0077] In the present specification, the above description on the heterocyclic group can be applied to the heteroaryl group and the heteroaryl group in the heteroarylamine group.

[0078] In the present specification, the arylene group and the aromatic hydrocarbon ring are each a divalent group, and other than this, the above description about the aryl group is applicable.

[0079] In the present specification, a heteroarylene group and a heterocycle are divalent groups, and other than this, the above description on the heterocyclic group is applicable.

[0080] In the present specification, combining with adjacent groups to form a substituted or unsubstituted ring means combining with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle, or a substituted or unsubstituted aromatic heterocycle.

[0081] In the present specification, an aliphatic hydrocarbon ring as a non-aromatic ring refers to a ring composed only of carbon and hydrogen atoms.

[0082] In the present specification, examples of the aromatic hydrocarbon ring include phenyl, naphthyl, anthracenyl and the like, but are not limited thereto.

[0083] In the present specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more hetero atoms.

[0084] In the present specification, an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms.

[0085] In the present specification, the above-mentioned aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocyclic ring and aromatic heterocyclic ring may each be a monocyclic ring or a polycyclic ring.

[0086] In this specification, "adjacent" groups may refer to substituents substituted on atoms directly connected to the atom substituted by the substituent, substituents closest to the substituent in stereostructure, or other substituents 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 to each other.

[0087] In the present specification, adjacent groups are combined with each other to form a substituted or unsubstituted ring, which means that adjacent groups are combined with each other to form a five-membered to eight-membered hydrocarbon ring or a five-membered to eight-membered heterocycle, which can be a monocyclic or polycyclic ring, and can be aliphatic, aromatic or a fused form thereof, and is not limited to these.

[0088] According to one embodiment of the present application, R1 to R3 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0089] In addition, according to one embodiment of the present application, R1 to R3 are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0090] In addition, according to one embodiment of the present application, R1 to R3 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; an aryl group substituted or unsubstituted by a group selected from deuterium, an alkyl group and a trialkylsilyl group; or a heterocyclic group.

[0091] In addition, according to one embodiment of the present application, R1 to R3 are each independently a methyl group; an ethyl group; an isopropyl group; a tert-butyl group; a phenyl group which may be substituted or unsubstituted by a group selected from deuterium, an alkyl group and a trialkylsilyl group; a biphenyl group; or a dibenzofuranyl group.

[0092] According to one embodiment of the present application, adjacent groups among R1 to R3, A, B and C may be combined to form a substituted or unsubstituted ring.

[0093] In addition, according to one embodiment of the present application, adjacent groups among R1 to R3, A, B and C may be combined to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0094] In addition, according to one embodiment of the present application, adjacent groups among R1 to R3, A, B and C may be combined to form a substituted or unsubstituted hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms.

[0095] In addition, according to one embodiment of the present application, adjacent groups among R1 to R3, A, B and C may be combined to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.

[0096] According to one embodiment of the present application, the above Chemical Formula 1 can be represented by the following Chemical Formula 1-1.

[0097] [Chemical formula 1-1]

[0098]

[0099] In Chemical Formula 1-1,

[0100] The definitions of A, B and C are the same as those in claim 1.

[0101] R' and R" are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0102] Adjacent groups among R', R", A, B and C may be combined to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0103] According to one embodiment of the present application, the compound represented by the above Chemical Formula 1 may contain at least one deuterium.

[0104] According to one embodiment of the present application, A, B and C are each independently a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle.

[0105] In addition, according to one embodiment of the present application, the above-mentioned A, B and C are a substituted or unsubstituted hydrocarbon ring having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 3 to 60 carbon atoms.

[0106] In addition, according to one embodiment of the present application, A, B and C are substituted or unsubstituted hydrocarbon rings having 6 to 30 carbon atoms, or substituted or unsubstituted heterocyclic rings having 3 to 30 carbon atoms.

[0107] According to one embodiment of the present application, A, B and C are each independently a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle, or a substituted or unsubstituted aromatic heterocycle.

[0108] According to one embodiment of the present application, A, B and C are each independently substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted carbazole, or substituted or unsubstituted phenanthrene.

[0109] According to one embodiment of the present application, the above Chemical Formula 1 can be represented by the following Chemical Formula 3.

[0110] [Chemical formula 3]

[0111]

[0112] In the above Chemical Formula 3, X1 and X2 are the same as those defined in Chemical Formula 1.

[0113] Z1 to Z3 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups may be combined with each other to form a substituted or unsubstituted ring,

[0114] a and b are each an integer from 1 to 4,

[0115] c is an integer from 1 to 3,

[0116] When a to c are 2 or more, the structures in the brackets are the same as or different from each other.

[0117] According to one embodiment of the present application, Z1 to Z3 are each independently hydrogen, deuterium, a substituted or unsubstituted amine, a substituted or unsubstituted silyl, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heterocyclic group, or adjacent groups can be combined with each other to form a substituted or unsubstituted ring.

[0118] According to one embodiment of the present application, Z1 to Z3 are each independently hydrogen; deuterium; a diarylamine group substituted or unsubstituted by a group selected from deuterium, a diarylamine group and a carbazole group; a phenyl group; a biphenyl group; a methyl group; a tert-butyl group; a carbazole group substituted or unsubstituted by a group selected from an aryl group and a carbazole group; or a trialkylsilyl group, or adjacent groups may be combined with each other to form a substituted or unsubstituted ring.

[0119] According to one embodiment of the present specification, when Z1 to Z3 and R1 to R3 are each independently bonded to adjacent groups to form a substituted or unsubstituted ring, the adjacent groups may be directly bonded to each other or connected by any of the following structures to form a ring.

[0120]

[0121] In the above structure,

[0122] A1 to A24 are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0123] a1 to a11 are each an integer from 0 to 4,

[0124] a12 is an integer from 0 to 6,

[0125] * indicates the position of substitution.

[0126] According to one embodiment of the present application, the above Chemical Formula 1 may be represented by any one of the following Chemical Formulas 3-1 to 3-3.

[0127] [Chemical formula 3-1]

[0128]

[0129] [Chemical formula 3-2]

[0130]

[0131] [Chemical formula 3-3]

[0132]

[0133] In the above chemical formulas 3-1 to 3-3,

[0134] X3 is a direct bond, O, CR11R12 or NR13,

[0135] Z11 to Z19 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups may be combined with each other to form a substituted or unsubstituted ring,

[0136] z11, z12 and z17 are each an integer from 1 to 4,

[0137] z13, z14, z15, z16, z18 and z19 are each an integer from 1 to 3,

[0138] When z11 to z19 are 2 or more, the structures in the brackets are the same or different from each other.

[0139] R4 to R8 and R11 to R13 are each independently a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0140] According to one embodiment of the present application, R4 to R8 are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0141] According to one embodiment of the present application, R4 to R8 are each independently a methyl group; an ethyl group; an isopropyl group; a tert-butyl group; a phenyl group which may be substituted or unsubstituted by a group selected from deuterium, an alkyl group and a trialkylsilyl group; a biphenyl group; or a dibenzofuranyl group.

[0142] According to one embodiment of the present application, R11 to R13 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0143] According to one embodiment of the present application, R11 to R13 are each independently hydrogen, deuterium, methyl or phenyl.

[0144] According to one embodiment of the present application, Z11 to Z19 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups can be combined with each other to form a substituted or unsubstituted ring.

[0145] According to one embodiment of the present application, Z11 to Z19 are each independently hydrogen; deuterium; a diarylamine group substituted or unsubstituted by a group selected from deuterium, a diarylamine group and a carbazole group; a phenyl group; a biphenyl group; a methyl group; a tert-butyl group; a carbazole group substituted or unsubstituted by a group selected from an aryl group and a carbazole group; or a trialkylsilyl group, or adjacent groups may be combined with each other to form a substituted or unsubstituted ring.

[0146] According to one embodiment of the present application, when adjacent groups among Z11 to Z19 are combined to form a substituted or unsubstituted ring, they may each independently form a substituted or unsubstituted indole ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring.

[0147] According to one embodiment of the present application, when adjacent groups among Z11 to Z19 are combined to form a substituted or unsubstituted ring, they may independently form an indole ring substituted or unsubstituted by an aryl group, a benzene ring substituted or unsubstituted by an alkyl group, or a naphthalene ring.

[0148] According to one embodiment of the present application, when adjacent groups among Z11 to Z19 are combined to form a substituted or unsubstituted ring, they can each independently form an indole ring substituted or unsubstituted by a phenyl group, a benzene ring substituted or unsubstituted by a tert-butyl group, or a naphthalene ring.

[0149] According to one embodiment of the present application, the above Chemical Formula 1 is selected from the following structural formulas.

[0150]

[0151]

[0152]

[0153]

[0154] An organic light emitting device according to one embodiment of the present application includes a compound represented by the following Chemical Formula 2.

[0155] [Chemical formula 2]

[0156]

[0157] In chemical formula 2,

[0158] At least one of X4 to X6 is N, and the others are CR',

[0159] Ar1 and Ar2 are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,

[0160] L is a direct bond, a substituted or unsubstituted n+1-valent aryl group, or a substituted or unsubstituted n+1-valent heterocyclic group,

[0161] Y is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0162] R' is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0163] n is 1 or 2,

[0164] When n is 2, two Ys may be the same as or different from each other.

[0165] According to one embodiment of the present application, at least one of X4 to X6 is N, and the others are CR'.

[0166] According to one embodiment of the present application, two or more of X4 to X6 are N, and the rest are CH.

[0167] According to one embodiment of the present application, two of X4 to X6 are N, and the rest are CH.

[0168] According to one embodiment of the present application, X4 to X6 are N.

[0169] According to one embodiment of the present application, Ar1 and Ar2 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0170] According to one embodiment of the present application, Ar1 and Ar2 are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0171] According to one embodiment of the present application, Ar1 and Ar2 are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

[0172] According to one embodiment of the present application, Ar1 and Ar2 are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0173] According to one embodiment of the present application, Ar1 and Ar2 are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

[0174] According to one embodiment of the present application, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0175] According to one embodiment of the present application, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

[0176] According to one embodiment of the present application, Ar1 and Ar2 are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, or substituted or unsubstituted pyrenyl.

[0177] According to one embodiment of the present application, Ar1 and Ar2 are each independently a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group substituted with an alkyl group, a dibenzofuranyl group, a dibenzothienyl group, or a pyrenyl group.

[0178] According to one embodiment of the present application, L is a direct bond, a substituted or unsubstituted n+1-valent aryl group, or a substituted or unsubstituted n+1-valent heterocyclic group.

[0179] According to one embodiment of the present application, L is a direct bond, a substituted or unsubstituted n+1-valent aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted n+1-valent heterocyclic group having 2 to 60 carbon atoms.

[0180] According to one embodiment of the present application, L is a direct bond, a substituted or unsubstituted n+1-valent aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted n+1-valent heterocyclic group having 2 to 30 carbon atoms.

[0181] According to one embodiment of the present application, L is a direct bond, a substituted or unsubstituted n+1-valent aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted n+1-valent heterocyclic group having 2 to 15 carbon atoms.

[0182] According to one embodiment of the present application, L is a substituted or unsubstituted trivalent aryl group, or a substituted or unsubstituted trivalent heterocyclic group.

[0183] According to one embodiment of the present application, L is a substituted or unsubstituted trivalent aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted trivalent heterocyclic group having 2 to 15 carbon atoms.

[0184] According to one embodiment of the present application, L is a substituted or unsubstituted trivalent aryl group.

[0185] According to one embodiment of the present application, L is a substituted or unsubstituted trivalent aromatic group having 2 to 15 carbon atoms.

[0186] According to one embodiment of the present application, L is a substituted or unsubstituted trivalent phenyl group, or a substituted or unsubstituted trivalent biphenyl group.

[0187] According to one embodiment of the present application, L is a trivalent phenyl group or a trivalent biphenyl group.

[0188] According to one embodiment of the present application, Y is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0189] According to one embodiment of the present application, Y is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

[0190] According to one embodiment of the present application, Y is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0191] According to one embodiment of the present application, Y is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

[0192] According to one embodiment of the present application, Y is a substituted or unsubstituted polycyclic aryl group. Here, polycyclic refers to a state in which two or more rings are condensed.

[0193] According to one embodiment of the present application, Y is a substituted or unsubstituted bicyclic to pentacyclic aryl group.

[0194] According to one embodiment of the present application, Y is a substituted or unsubstituted bicyclic to tetracyclic aryl group.

[0195] According to one embodiment of the present application, Y is a substituted or unsubstituted bicyclic to tricyclic aryl group.

[0196] According to one embodiment of the present application, Y is a substituted or unsubstituted polycyclic aromatic group having 6 to 60 carbon atoms.

[0197] According to one embodiment of the present application, Y is a substituted or unsubstituted polycyclic aromatic group having 6 to 30 carbon atoms.

[0198] According to one embodiment of the present application, Y is a substituted or unsubstituted polycyclic aromatic group having 6 to 15 carbon atoms.

[0199] According to one embodiment of the present application, Y is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted fluorenyl group.

[0200] According to one embodiment of the present application, n is 1 or 2.

[0201] According to one embodiment of the present application, n is 2.

[0202] According to one embodiment of the present application, when n is 2, two Ys are identical to each other.

[0203] According to one embodiment of the present application, when n is 2, the two Ys are different from each other.

[0204] According to one embodiment of the present application, R' is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0205] According to one embodiment of the present application, R′ is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0206] According to one embodiment of the present application, R' is hydrogen or deuterium.

[0207] According to one embodiment of the present application, the above Chemical Formula 2 is selected from the following structural formulas.

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220] For example, the compound of the above chemical formula 1 can be used to prepare a core structure as shown in the following reaction formula 1, and the compound of the above chemical formula 2 can be used to prepare a core structure as shown in the following reaction formula 2. The substituents can be combined by methods known in the art, and the type, position or number of the substituents can be changed according to techniques known in the art.

[0221] [Reaction 1]

[0222]

[0223] In the above reaction formula 1, A, B and C have the same definitions as in chemical formula 1.

[0224] D and E are each independently a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle, and A1 to A3 are each a functional group capable of undergoing a coupling reaction with an amine.

[0225] Under a nitrogen atmosphere, an amine compound and a halogenated aromatic ring compound are subjected to a coupling reaction using a Pd catalyst to obtain a compound having a structure of Chemical Formula A.

[0226] Another amine compound of the same equivalent as that of chemical formula A is added, and a compound having a structure of chemical formula B is obtained by a coupling reaction using a Pd catalyst. In addition, a t-Butyl Lithium solution is added to a flask containing a compound having a structure of chemical formula B at -80°C. After stirring for about 30 minutes, boron tribromide is added and the temperature is raised to room temperature. Then, it is cooled to 0°C again, N,N-diisopropylethylamine is added, and the temperature is raised to 120°C and heated and stirred. After the reaction is completed, it is cooled to room temperature, and then purified to obtain the core structure of chemical formula 1-1-1.

[0227] [Reaction 2]

[0228]

[0229] In the above Reaction Formula 2, X4 to X6, L, n, Ar1 and Ar2 are the same as defined in Chemical Formula 2.

[0230] In the above reaction formula 2, a triazine compound and a linker in the form of boronic acid or boronate ( (link)) was subjected to a coupling reaction using Pd as a catalyst to obtain a compound having a structure of chemical formula C.

[0231] Add the same amount of Bis(pinacolato)diboron as that of Formula C to the diboron In a dioxane solvent, a borylation reaction is carried out using KOAc and Pd as a catalyst to obtain a compound having a structure of Chemical Formula D. Furthermore, by a coupling reaction of the compound having a structure of Chemical Formula D with Y, a core structure of Chemical Formula 2 is obtained.

[0232] The organic layer of the organic light-emitting device of the present application may be formed by a single-layer structure, or may be formed by a multi-layer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0233] In one embodiment of the present application, the organic layer may include a layer including the compound represented by Chemical Formula 2 between the first electrode and the light-emitting layer.

[0234] In one embodiment of the present application, the organic layer may include a layer including the compound represented by Chemical Formula 2 between the second electrode and the light-emitting layer.

[0235] In one embodiment of the present application, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound represented by Chemical Formula 2.

[0236] In one embodiment of the present application, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1.

[0237] In one embodiment of the present application, the organic light-emitting device further includes one or more layers selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer.

[0238] The light emitting layer may include a compound represented by Chemical Formula 1. Specifically, the light emitting layer may include a host and a dopant represented by Chemical Formula 1.

[0239] The above-mentioned light-emitting layer may contain a compound represented by Chemical Formula 1 as a dopant material. The host material includes an aromatic condensed ring derivative or a heterocyclic compound. Specifically, as the aromatic condensed ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as the heterocyclic compound, there are carbazole derivatives, dibenzofuran, dibenzofuran derivatives, dibenzothiophene, dibenzothiophene derivatives, ladder-type furan compounds. Pyrimidine derivatives, etc., but are not limited to these.

[0240] In one embodiment of the present application, the weight ratio of the host to the dopant may be 90:10 to 99:1. Specifically, it may be 90:10, 91:9, 92:8, 93:7, 94:6, 95:5, 96:4, 97:3, 98:2 or 99:1, preferably, it may be 95:5, but it is not limited thereto.

[0241] In one embodiment of the present application, the thickness of the organic layer containing the compound of the above Chemical Formula 1 or 2 is to

[0242] In one embodiment of the present application, the host includes an anthracene derivative. In this case, the anthracene derivative may be substituted or unsubstituted anthracene, and adjacent substituents in the anthracene may be bonded to form a substituted or unsubstituted ring.

[0243] In one embodiment of the present application, the host includes a compound represented by the following Chemical Formula 4.

[0244] [Chemical formula 4]

[0245]

[0246] In the above chemical formula 4,

[0247] L101 and L102 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0248] R101 to R108 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or adjacent substituents are combined to form a substituted or unsubstituted ring,

[0249] Ar101 and Ar102 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or are connected with adjacent substituents to form a substituted or unsubstituted ring,

[0250] m1 and m2 are each an integer from 0 to 5,

[0251] When m1 is 2 or more, L101 are the same or different from each other.

[0252] When m2 is 2 or more, L102 may be the same as or different from each other.

[0253] In one embodiment of the present application, the host includes a compound represented by any one of the following structures.

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276] In one embodiment of the present application, the organic light-emitting device includes a first electrode; a second electrode disposed opposite to the first electrode; a light-emitting layer disposed between the first electrode and the second electrode; and one or more organic layers disposed between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode. In one embodiment of the present application, the one or more organic layers may be selected from an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects electrons, and a hole blocking layer.

[0277] In one embodiment of the present application, the organic light-emitting device may include an anode, a cathode opposite to the anode, a light-emitting layer between the anode and the cathode and containing a compound represented by the following chemical formula 1, a hole transport region between the anode and the light-emitting layer, and an electron transport region between the cathode and the light-emitting layer and containing a compound represented by the following chemical formula 2.

[0278] In one embodiment of the present application, the hole transport region refers to a region including one or more organic layers between the anode and the light-emitting layer, and receiving holes from the anode and transferring them to the light-emitting layer. The hole transport region may include at least one of a hole injection layer, a hole transport layer, a hole injection and transport layer, a hole regulating layer, and an electron blocking layer.

[0279] In one embodiment of the present application, the electron transport region refers to a region including one or more organic layers between the cathode and the light-emitting layer, and receiving holes from the cathode and transferring them to the light-emitting layer. The electron transport region may include at least one of an electron injection layer, an electron transport layer, an electron injection and transport layer, an electron regulating layer, and a hole blocking layer.

[0280] The electron transport region includes an electron regulating layer, an electron injection layer, an electron transport layer, or an electron injection and transport layer. The electron regulating layer, the electron injection layer, the electron transport layer, or the electron injection and transport layer may contain the compound represented by Chemical Formula 2.

[0281] In one embodiment of the present application, the electron transport region includes two or more electron transport layers, and at least one of the two or more electron transport layers contains the compound represented by the chemical formula 2. Specifically, in one embodiment of the present application, the compound represented by the chemical formula 2 may be contained in one of the two or more electron transport layers, or in each of the two or more electron transport layers.

[0282] In addition, in one embodiment of the present application, when the compound represented by the above Chemical Formula 2 is included in each of the above two or more electron transport layers, other materials except the above compound may be the same as or different from each other.

[0283] In another embodiment, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

[0284] In another embodiment, the organic light emitting device may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

[0285] For example, the structure of the organic light-emitting device according to one embodiment of the present application is shown in Figure 1 and 2 .

[0286] Figure 1 The structure of an organic light-emitting device is illustrated in which a substrate 1, an anode 2, a hole transport region 10, a light-emitting layer 3, an electron transport region 20, and a cathode 4 are sequentially stacked. In the structure described above, the compound represented by the above chemical formula 1 is contained in the above light-emitting layer 3, and the compound represented by the above chemical formula 2 may be contained in the electron transport region 20.

[0287] Figure 2 The structure of an organic light-emitting device is illustrated, which is sequentially stacked with a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron adjustment layer 7, an electron injection and transport layer 8, and a cathode 4. In the structure described above, the compound represented by the above chemical formula 1 is contained in the above light-emitting layer 3, and the compound represented by the above chemical formula 2 may be contained in the electron adjustment layer 7 or the electron injection and transport layer 8.

[0288] The organic light-emitting device of the present application 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 the present application, namely, the above-mentioned compound.

[0289] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

[0290] The organic light-emitting device of the present application 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 represented by the above Chemical Formula 1.

[0291] For example, the organic light-emitting device of the present application 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: using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation (e-beamevaporation), a metal or a conductive metal oxide or an alloy thereof is evaporated 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 evaporated on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on a substrate.

[0292] 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 device. 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 thereto.

[0293] In addition to these methods, an organic light-emitting device can also 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.

[0294] In one embodiment of the present application, the first electrode is an anode, and the second electrode is a cathode.

[0295] In another embodiment, the first electrode is a cathode, and the second electrode is an anode.

[0296] As the above-mentioned anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0297] As the cathode material, in order to facilitate the injection of electrons into the organic layer, a material with a small work function is preferably used. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0298] The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has the effect of injecting holes from the anode, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film forming ability. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine organic matter; hexanitrile hexaazatriphenylene organic matter; quinacridone organic matter; perylene organic matter; anthraquinone and polyaniline and polythiophene conductive polymers, but are not limited to these.

[0299] The hole transport layer is a layer that receives holes from the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer. Materials with high hole mobility are suitable. Specific examples include arylamine organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited thereto.

[0300] The light-emitting layer may contain other light-emitting substances in addition to the compound represented by the chemical formula 1. Specific examples include 8-hydroxyquinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo azole, benzothiazole and benzimidazole compounds; poly(p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0301] The electron transport layer is a layer that receives electrons from the cathode or the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport substance is a substance that can well inject electrons from the cathode and transfer them to the light-emitting layer, preferably a substance with a large mobility for electrons. As a specific example, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to this. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are common substances with low work function and accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum or silver layer.

[0302] The electron injection layer is a layer for injecting electrons from the cathode, and is preferably a compound that has the ability to transport electrons, has the effect of injecting electrons from the cathode, has an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from migrating to the hole injection layer, and has excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0303] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.

[0304] The hole blocking layer is a layer that prevents holes from reaching the cathode and can usually be formed using the same conditions as the hole injection layer. Examples of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0305] Depending on the materials used, the organic light-emitting device according to the present application may be a top emission type, a bottom emission type, or a bidirectional emission type.

[0306] Modes for Carrying Out the Invention

[0307] The manufacture of an organic light-emitting device including the compounds represented by the above Chemical Formulae 1 and 2 is specifically described in the following examples. However, the following examples are used to illustrate the present specification, and the scope of the present specification is not limited thereto.

[0308] [Production Example 1: Chemical Formula 1]

[0309] <Production Example 1-1> Synthesis of Compound 1-1

[0310] 1) Synthesis of Compound 1-1-A

[0311]

[0312] Under nitrogen atmosphere, a flask containing N-methylaniline (30.0 g), 1-bromo-2,3-dichlorobenzene (63 g), Pd(tBu3P)2 (0.29 g), NaOtBu (53.8 g) and xylene (500 ml) was heated and stirred at 80°C for 4 hours, then heated to 120°C and heated and stirred for another 3 hours. After the reaction solution was cooled to room temperature, water and ethyl acetate were added for separation. Subsequently, it was purified by silica gel column chromatography (developing solution: toluene / heptane = 1 / 20 (volume ratio)) to obtain 2,3-dichloro-N-methyl-N-phenylaniline (64.0 g).

[0313] Here, tBu means tert-butyl.

[0314] MS[M+H] + =252

[0315] 2) Synthesis of Compound 1-1-B

[0316]

[0317] Under a nitrogen atmosphere, a flask containing 2,3-dichloro-N-methyl-N-phenylaniline (20.0 g), N-methylaniline (8.5 g), Pd(t-Bu3P)2 (0.08 g), NaOtBu (15.2 g) and xylene was heated and stirred at 120°C for 1 hour. After the reaction solution was cooled to room temperature, water and ethyl acetate were added for separation. Then, it was purified by a silica gel short-path chromatography column (developing liquid: heated toluene), and further washed with a mixed solvent of heptane and ethyl acetate (their volume ratio was heptane / ethyl acetate = 1), thereby obtaining 2-chloro-N1,N3-dimethyl-N1,N3-diphenylbenzene-1,3-diamine (23.2 g).

[0318] MS[M+H] + =323

[0319] 3) Synthesis of Compound 1-1

[0320]

[0321] Under nitrogen atmosphere, at -30°C, a 1.6M tert-butyllithium pentane solution (48.4ml) was added to a flask containing 2-chloro-N1,N3-dimethyl-N1,N3-diphenylbenzene-1,3-diamine (25.0g) and tert-butylbenzene (130ml). After the addition was completed, the temperature was raised to 60°C, stirred for 1 hour, and then components with a lower boiling point than tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -30°C, boron tribromide (10.6ml) was added, the temperature was raised to room temperature, and stirred for 0.5 hours. Then, the mixture was cooled to 0°C again, N,N-diisopropylethylamine (12.8ml) was added, and the mixture was stirred at room temperature until the generated heat cooled down, and then the temperature was raised to 120°C and heated and stirred for 2 hours. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by separation by adding ethyl acetate. Next, the mixture was purified using a silica gel short-path chromatography column (developing solution: heated chlorobenzene). After washing with refluxing heptane and refluxing ethyl acetate, the product was reprecipitated from chlorobenzene to obtain the compound represented by Chemical Formula 1-1 (16.3 g).

[0322] MS[M+H] + =297

[0323] <Production Example 1-2> Synthesis of Compound 1-2

[0324] 1) Synthesis of Compound 1-2-A

[0325]

[0326] Under nitrogen atmosphere, a flask containing diphenylamine (37.5 g), 1-bromo-2,3-dichlorobenzene (50.0 g), Pd(t-Bu3P)2 (0.58 g), NaOtBu (32.0 g) and xylene (500 ml) was heated and stirred at 80°C for 4 hours, then heated to 120°C and heated and stirred for another 3 hours. After the reaction solution was cooled to room temperature, water and ethyl acetate were added for separation. Subsequently, it was purified by silica gel column chromatography (developing solution: toluene / heptane = 1 / 20 (volume ratio)) to obtain 2,3-dichloro-N,N-diphenylaniline (63.0 g).

[0327] MS[M+H] + =314

[0328] 2) Synthesis of Compound 1-2-B

[0329]

[0330] Under a nitrogen atmosphere, a flask containing 2,3-dichloro-N,N-diphenylaniline (16.2 g), di([1,1'-biphenyl]-4-yl)amine (15.0 g), Pd(t-Bu3P)2 (0.22 g), NaOtBu (6.7 g) and xylene (150 ml) was heated and stirred at 120°C for 1 hour. After the reaction solution was cooled to room temperature, water and ethyl acetate were added for separation. Then, it was purified by a silica gel short-path chromatography column (developing solution: heated toluene), and further washed with a mixed solvent of heptane and ethyl acetate (their volume ratio was heptane / ethyl acetate = 1), thereby obtaining N1,N1-di([1,1'-biphenyl]-4-yl)-2-chloro-N3,N3-diphenylbenzene-1,3-diamine (22.0 g).

[0331] MS[M+H] + =599

[0332] 3) Synthesis of Compound 1-2

[0333]

[0334] Under nitrogen atmosphere, at -30°C, a 1.6M tert-butyllithium pentane solution (48.4ml) was added to a flask containing N1,N1-di([1,1'-biphenyl]-4-yl)-2-chloro-N3,N3-diphenylbenzene-1,3-diamine (22.0g) and tert-butylbenzene (130ml). After the addition was completed, the temperature was raised to 60°C, stirred for 1 hour, and then components with a lower boiling point than tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -30°C, boron tribromide (6.2ml) was added, the temperature was raised to room temperature, and stirred for 0.5 hours. Then, the mixture was cooled to 0°C again, N,N-diisopropylethylamine (12.8ml) was added, and the mixture was stirred at room temperature until the generated heat cooled down, and then the temperature was raised to 120°C and heated and stirred for 2 hours. The reaction solution was cooled to room temperature, an aqueous sodium acetate solution cooled in an ice bath was added, and then ethyl acetate was added for separation. Next, the product was purified using a silica gel short-path column (developing solution: heated chlorobenzene), washed with refluxing heptane and refluxing ethyl acetate, and then reprecipitated from chlorobenzene to obtain the compound represented by Chemical Formula 1-2 (11.2 g).

[0335] MS[M+H] + =573

[0336] <Production Example 3> Synthesis of Compound 1-3

[0337] 1) Synthesis of Compound 1-3-A

[0338]

[0339] Compound 1-3-A was produced by the same method as compound 1-1-A except that di([1,1'-biphenyl]-3-yl)amine was used instead of N-methylaniline.

[0340] MS[M+H] + =466

[0341] 2) Synthesis of Compound 1-3-B

[0342]

[0343] Compound 1-3-B was produced by the same method as compound 1-1-B, except that [compound 1-3-A] was used instead of [compound 1-1-A] and N1,N1,N3-triphenylbenzene-1,3-diamine was used instead of N-methylaniline.

[0344] MS[M+H] + =614

[0345] 3) Synthesis of Compound 1-3

[0346]

[0347] Compound 1-3 was produced by the same method as compound 1-1, except that [compound 1-3-B] was used instead of [compound 1-1-B].

[0348] MS[M+H] + =740

[0349] <Production Example 1-4> Synthesis of Compound 1-4

[0350] 1) Synthesis of Compound 1-4-A

[0351]

[0352] Compound 1-4-A was produced by the same method as compound 1-1-A except that 1-bromo-2,3-dichloro-5-methylbenzene was used instead of 1-bromo-2,3-dichlorobenzene and 3,5-di-tert-butyl-N-(3-(tert-butyl)phenyl)aniline was used instead of N-methylaniline.

[0353] MS[M+H] + =496

[0354] 2) Synthesis of Compound 1-4-B

[0355]

[0356] Compound 1-4-B was produced by the same method as Compound 1-1-B, except that [Compound 1-4-A] was used instead of [Compound 1-1-A] and bis(4-(tert-butyl)phenyl)amine was used instead of N-methylaniline.

[0357] MS[M+H] + =741

[0358] 3) Synthesis of Compounds 1-4

[0359]

[0360] Compound 1-4 was produced by the same method as Compound 1-1, except that [Compound 1-4-B] was used instead of [Compound 1-1-B].

[0361] MS[M+H] + =715

[0362] <Production Example 1-5> Synthesis of Compound 1-5

[0363] 1) Synthesis of Compound 1-5-A

[0364]

[0365] Compound 1-5-A was produced by the same method as compound 1-1-A except that N,9-diphenyl-9H-carbazole-2-amine was used instead of N-methylaniline.

[0366] MS[M+H] + =479

[0367] 2) Synthesis of Compound 1-5-B

[0368]

[0369] Compound 1-5-B was produced by the same method as compound 1-1-B, except that [compound 1-5-A] was used instead of [compound 1-1-A] and N1,N1,N3-triphenylbenzene-1,3-diamine was used instead of N-methylaniline.

[0370] MS[M+H] + =779

[0371] 3) Synthesis of Compounds 1-5

[0372]

[0373] Compound 1-5 was produced by the same method as compound 1-1, except that [compound 1-5-B] was used instead of [compound 1-1-B].

[0374] MS[M+H] + =753

[0375] <Production Example 1-6> Synthesis of Compound 1-6

[0376] 1) Synthesis of Compound 1-6-A

[0377]

[0378] Compound 1-6-A was produced by the same method as compound 1-1-A except that N-phenylnaphthalene-2-amine was used instead of N-methylaniline.

[0379] MS[M+H] + =364

[0380] 2) Synthesis of Compound 1-6-B

[0381]

[0382] Compound 1-6-B was produced by the same method as compound 1-1-B, except that [compound 1-6-A] was used instead of [compound 1-1-A] and diphenylamine was used instead of N-methylaniline.

[0383] MS[M+H] + =497

[0384] 3) Synthesis of Compounds 1-6

[0385]

[0386] Compound 1-6 was produced by the same method as compound 1-1, except that [compound 1-6-B] was used instead of [compound 1-1-B].

[0387] MS[M+H] + =471

[0388] <Production Example 1-7> Synthesis of Compound 1-7

[0389] 1) Synthesis of Compound 1-7-A

[0390]

[0391] Compound 1-7-A was produced by the same method as compound 1-1-A except that 9-(3-bromo-4,5-dichlorophenyl)-9H-carbazole was used instead of 1-bromo-2,3-dichlorobenzene and 3-(tert-butyl)-N-(4-(tert-butyl)phenyl)aniline was used instead of N-methylaniline.

[0392] MS[M+H] + =591

[0393] 2) Synthesis of Compound 1-7-B

[0394]

[0395] Compound 1-7-B was produced by the same method as Compound 1-1-B, except that [Compound 1-7-A] was used instead of [Compound 1-1-A] and bis(4-(tert-butyl)phenyl)amine was used instead of N-methylaniline.

[0396] MS[M+H] + =836

[0397] 3) Synthesis of Compounds 1-7

[0398]

[0399] Compound 1-7 was produced by the same method as compound 1-1, except that [compound 1-7-B] was used instead of [compound 1-1-B].

[0400] MS[M+H] + =810

[0401] <Production Example 1-8> Synthesis of Compound 1-8

[0402] 1) Synthesis of Compound 1-8-A

[0403]

[0404] Compound 1-8-A was produced by the same method as compound 1-1-A except that 3-bromo-4,5-dichloro-N,N-diphenylaniline was used instead of 1-bromo-2,3-dichlorobenzene and 3-(tert-butyl)-N-(4-(tert-butyl)phenyl)aniline was used instead of N-methylaniline.

[0405] MS[M+H] + =593

[0406] 2) Synthesis of Compound 1-8-B

[0407]

[0408] Compound 1-8-B was produced by the same method as Compound 1-1-B, except that [Compound 1-8-A] was used instead of [Compound 1-1-A] and 3-(tert-butyl)-N-(4-(tert-butyl)phenyl)aniline was used instead of N-methylaniline.

[0409] MS[M+H] + =838

[0410] 3) Synthesis of Compounds 1-8

[0411]

[0412] Compound 1-8 was produced by the same method as Compound 1-1, except that [Compound 1-8-B] was used instead of [Compound 1-1-B].

[0413] MS[M+H] + =812

[0414] <Production Example 1-9> Synthesis of Compound 1-9

[0415] 1) Synthesis of Compound 1-9-A

[0416]

[0417] Compound 1-9-A was produced by the same method as compound 1-1-A except that N-phenyldibenzo[b,d]furan-3-amine was used instead of N-methylaniline.

[0418] MS[M+H]+ =404

[0419] 2) Synthesis of Compound 1-9-B

[0420]

[0421] Compound 1-9-B was produced by the same method as compound 1-1-B, except that [Compound 1-9-A] was used instead of [Compound 1-1-A] and N-phenyldibenzo[b,d]furan-3-amine was used instead of N-methylaniline.

[0422] MS[M+H] + =627

[0423] 3) Synthesis of Compound 1-9

[0424]

[0425] Compound 1-9 was produced by the same method as Compound 1-1, except that [Compound 1-9-B] was used instead of [Compound 1-1-B].

[0426] MS[M+H] + =601

[0427] <Production Example 1-10> Synthesis of Compound 1-10

[0428] 1) Synthesis of Compound 1-10-A

[0429]

[0430] Compound 1-10-A was produced by the same method as compound 1-1-A except that N-phenyl-4-(trimethylsilyl)aniline was used instead of N-methylaniline and 3-bromo-4,5-dichloro-N,N-diphenylaniline was used instead of 1-bromo-2,3-dichlorobenzene.

[0431] MS[M+H] + =553

[0432] 2) Synthesis of Compound 1-10-B

[0433]

[0434] Compound 1-10-B was produced by the same method as Compound 1-1-B, except that [Compound 1-10-A] was used instead of [Compound 1-1-A] and N-phenyl-4-(trimethylsilyl)aniline was used instead of N-methylaniline.

[0435] MS[M+H] +=758

[0436] 3) Synthesis of Compound 1-10

[0437]

[0438] Compound 1-10 was produced by the same method as Compound 1-1, except that [Compound 1-10-B] was used instead of [Compound 1-1-B].

[0439] MS[M+H] + =732

[0440] <Production Example 1-11> Synthesis of Compound 1-11

[0441] 1) Synthesis of Compound 1-11-A

[0442]

[0443] Compound 1-11-A was produced by the same method as compound 1-1-A except that 4-(tert-butyl)-N-phenylaniline was used instead of N-methylaniline and 3-bromo-4,5-dichloro-N,N-diphenylaniline was used instead of 1-bromo-2,3-dichlorobenzene.

[0444] MS[M+H] + =557

[0445] 2) Synthesis of Compound 1-11-B

[0446]

[0447] Compound 1-11-B was produced by the same method as compound 1-1-B, except that [compound 1-11-A] was used instead of [compound 1-1-A] and N-(4-(tert-butyl)phenyl)-3-fluoroaniline was used instead of N-methylaniline.

[0448] MS[M+H] + =744

[0449] 3) Synthesis of Compound 1-11-C

[0450]

[0451] Compound 1-11-C was produced by the same method as compound 1-1, except that [compound 1-11-B] was used instead of [compound 1-1-B].

[0452] MS[M+H] + =718

[0453] 4) Synthesis of Compound 1-11

[0454]

[0455] Under a nitrogen atmosphere, [Compound 1-11-C] (20 g), potassium carbonate (potassium carbonate) (7.7 g) and Pd (PPh3) 4 (Tetrakis (triphenylphosphine) palladium (0)) (1.61 g) were added to dimethylacetamide (140 ml) and heated and stirred at 120 ° C for 1 hour. After the reaction solution was cooled to room temperature, it was filtered. Then, it was purified with a silica gel short-path chromatography column (developing solution: heated toluene), and further washed with a mixed solvent of heptane and ethyl acetate (their volume ratio was heptane / ethyl acetate = 1) to obtain [Compound 1-11] (28.0 g).

[0456] MS[M+H] + =698

[0457] <Production Example 2: Chemical Formula 2>

[0458] <Production Example 2-1> Synthesis of Compound 2-1

[0459] 1) Synthesis of Compound 2-1-A

[0460]

[0461] Under nitrogen flow, 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (15g, 43.6mmol) and (3,5-dichlorophenyl)boric acid (9.2g, 47.9mmol) were dissolved in 150mL of tetrahydrofuran solvent, and potassium carbonate (12.1g, 87.3mmol) aqueous solution was added and heated with stirring. Under reflux, Pd(PPh3)4 (1.5g, 1.3mmol) was added and heated with stirring for 6 hours. After the reaction was completed, the temperature was lowered to room temperature, and then the potassium carbonate solution was removed and filtered. The filtered solid was washed with ethanol to produce compound 2-1-A (17.8g, yield 90%).

[0462] MS[M+H] + =454

[0463] 2) Synthesis of Compound 2-1-B

[0464]

[0465] Under nitrogen flow, compound 2-1-A (17.8 g, 39.2 mmol) and bis(pinacolato)diboron (10.9 g, 43.1 mmol) were dissolved in 180 mL of diboron. After alkane solvent, potassium acetate (11.5 g, 117.5 mmol) was added and heated with stirring. Under reflux, Pd(dba)2(Bis(dibenzylideneacetone)palladium(0)) (0.7 g, 1.2 mmol) and PCy3(Tricyclohexylphosphine) (0.7 g, 2.4 mmol) were added and heated with stirring for 8 hours. After the reaction was completed, the temperature was lowered to room temperature and then filtered once to remove impurities. The filtrate was added to water, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After vacuum distillation, the mixture was washed with ethanol to produce compound 2-1-B (21 g, yield 84%).

[0466] MS[M+H] + =638

[0467] 3) Synthesis of Compound 2-1

[0468]

[0469] Under nitrogen flow, compound 2-1-B (21 g, 32.9 mmol) and 1-bromonaphthalene (14.3 g, 69.2 mmol) were dissolved in tetrahydrofuran, and potassium carbonate (18.2 g, 132.8 mmol) was added in aqueous solution and heated with stirring. Under reflux, catalyst Pd(PPh3)4 (1.2 g, 1.0 mmol) was added and heated with stirring for 8 hours. After the reaction was completed, the temperature was lowered to room temperature, and then the potassium carbonate solution was removed and filtered. The filtered solid was washed with ethanol to produce compound 2-1 (18 g, yield 85%).

[0470] MS[M+H] + =638

[0471] The synthesis confirmation data of the above compound 2-1 is shown in Figure 3 .

[0472] <Production Example 2-2> Synthesis of Compound 2-2

[0473]

[0474] Under nitrogen flow, compound 2-1-B (21 g, 32.9 mmol) and 2-bromonaphthalene (14.3 g, 69.2 mmol) were dissolved in tetrahydrofuran, and potassium carbonate (18.2 g, 132.8 mmol) was added in aqueous solution and heated with stirring. Under reflux, catalyst Pd (PPh3) 4 (1.2 g, 1.0 mmol) was added and heated with stirring for 8 hours. After the reaction was completed, the temperature was lowered to room temperature, and then the potassium carbonate solution was removed and filtered. The filtered solid was washed with ethanol to produce compound 2-2 (18 g, yield 85%).

[0475] MS[M+H] + =638

[0476] The synthesis confirmation data of the above compound 2-2 is shown in Figure 4 .

[0477] <Production Example 2-3> Synthesis of Compound 2-3

[0478] 1) Synthesis of Compound 2-3-A

[0479]

[0480] Compound 2-3-A was produced by the same method as compound 2-1-A except that (3-bromo-5-chlorophenyl)boric acid was used instead of (3,5-dichlorophenyl)boric acid.

[0481] MS[M+H] + =499

[0482] 2) Synthesis of Compound 2-3-B

[0483]

[0484] Under nitrogen flow, compound 2-3-A (20 g, 40.1 mmol) and 1-naphthylboronic acid (7.6 g, 44.1 mmol) were dissolved in 1.4-dihydrochloric acid. After alkylation, potassium phosphate (17.0 g, 80.2 mmol) was added in the form of an aqueous solution and heated with stirring. Under reflux, catalyst Pd(PPh3)4 (1.4 g, 1.2 mmol) was added and heated with stirring for 8 hours. After the reaction was completed, the temperature was lowered to room temperature, and then the potassium phosphate solution was removed and filtered. The filtered solid was washed with ethanol to produce compound 2-3-B (18 g, yield 82%).

[0485] MS[M+H] + =546

[0486] 3) Synthesis of Compound 2-3

[0487]

[0488] Compound 2-3 was produced by the same method as for compound 2-1, except that compound 2-3-B was used instead of compound 2-1-B and (4-(1-naphthyl)phenyl)boric acid was used instead of 1-bromonaphthalene.

[0489] MS[M+H] + =714

[0490] The synthesis confirmation data of the above compound 2-3 is shown in Figure 5 .

[0491] <Production Example 2-4> Synthesis of Compound 2-4

[0492]

[0493] Compound 2-4 was produced by the same method as Compound 2-3 except that (4-(2-naphthyl)phenyl)boric acid was used instead of (4-(1-naphthyl)phenyl)boric acid.

[0494] MS[M+H] + =714

[0495] The synthesis confirmation data of the above compound 2-4 are shown in Figure 6 .

[0496] <Production Example 2-5> Synthesis of Compound 2-5

[0497] 1) Synthesis of Compound 2-5-B

[0498]

[0499] Compound 2-5-B was produced by the same method as compound 2-3-B except that 2-naphthylboronic acid was used instead of 1-naphthylboronic acid.

[0500] MS[M+H] + =546

[0501] 2) Synthesis of Compound 2-5

[0502] Compound 2-5 was produced by the same method as compound 2-3, except that compound 2-5-B was used instead of compound 2-3-B, and (4-(2-naphthyl)phenyl)boric acid was used instead of (4-(1-naphthyl)phenyl)boric acid.

[0503] MS[M+H] + =714

[0504] The synthesis confirmation data of the above compound 2-5 are shown in Figure 7 .

[0505] <Production Example 2-6> Synthesis of Compound 2-6

[0506]

[0507] Compound 2-6 was produced by the same method as Compound 2-5, except that (4-(1-naphthyl)phenyl)boric acid was used instead of (4-(2-naphthyl)phenyl)boric acid.

[0508] MS[M+H] + =714

[0509] The synthesis confirmation data of the above compounds 2-6 are shown in Figure 8 .

[0510] <Production Example 2-7> Synthesis of Compound 2-7

[0511]

[0512] Compound 2-7 was produced by the same method as compound 2-1 except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.

[0513] MS[M+H] + =738

[0514] <Production Example 2-8> Synthesis of Compound 2-8

[0515] 1) Synthesis of Compound 2-8-A

[0516]

[0517] Compound 2-8-A was produced by the same method as compound 2-1-A except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0518] MS[M+H] + =454

[0519] 2) Synthesis of Compound 2-8-B

[0520]

[0521] Compound 2-8-B was produced by the same method as compound 2-1-B except that compound 2-8-A was used instead of compound 2-1-A.

[0522] MS[M+H] +=638

[0523] 3) Synthesis of Compound 2-8

[0524]

[0525] Compound 2-8 was produced by the same method as compound 2-7, except that compound 2-8-B was used instead of compound 2-1-B.

[0526] MS[M+H] + =738

[0527] <Production Example 2-9> Synthesis of Compound 2-9

[0528]

[0529] Compound 2-9 was produced by the same method as compound 2-8 except that 1-bromonaphthalene was used instead of 9-bromophenanthrene.

[0530] MS[M+H] + =638

[0531] The synthesis confirmation data of the above compound 2-9 are shown in Fig. 9 .

[0532] <Production Example 2-10> Synthesis of Compound 2-10

[0533]

[0534] Compound 2-10 was produced by the same method as compound 2-8 except that 2-bromonaphthalene was used instead of 9-bromophenanthrene.

[0535] MS[M+H] + =638

[0536] The synthesis confirmation data of the above compound 2-10 are shown in Fig.10 .

[0537] <Production Example 2-11> Synthesis of Compound 2-11

[0538] 1) Synthesis of Compound 2-11-A

[0539]

[0540] Compound 2-11-A was produced by the same method as compound 2-3-A except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0541] MS[M+H] + =499

[0542] 2) Synthesis of Compound 2-11-B

[0543]

[0544] Compound 2-11-B was produced by the same method as compound 2-3-B except that compound 2-11-A was used instead of compound 2-3-A.

[0545] MS[M+H] + =546

[0546] 3) Synthesis of Compound 2-11

[0547]

[0548] Compound 2-11 was produced by the same method as compound 2-3, except that compound 2-11-B was used instead of compound 2-3-B.

[0549] MS[M+H] + =714

[0550] The synthesis confirmation data of the above compound 2-11 are shown in Fig.11 .

[0551] <Production Example 2-12> Synthesis of Compound 2-12

[0552]

[0553] Compound 2-12 was produced by the same method as compound 2-4 except that compound 2-11-B was used instead of compound 2-3-B.

[0554] MS[M+H] + =714

[0555] The synthesis confirmation data of the above compound 2-12 are shown in Fig.12 .

[0556] <Production Example 2-13> Synthesis of Compound 2-13

[0557] 1) Synthesis of Compound 2-13-B

[0558]

[0559] Compound 2-13-B was produced by the same method as compound 2-5-B except that compound 2-11-A was used instead of compound 2-3-A.

[0560] MS[M+H] + =546

[0561] 2) Synthesis of Compound 2-13

[0562]

[0563] Compound 2-13 was produced by the same method as compound 2-5, except that compound 2-13-B was used instead of compound 2-5-B.

[0564] MS[M+H] + =714

[0565] The synthesis confirmation data of the above compound 2-13 are shown in Fig.13 .

[0566] <Production Example 2-14> Synthesis of Compound 2-14

[0567]

[0568] Compound 2-14 was produced by the same method as Compound 2-13 except that (4-(naphthalen-1-yl)phenyl)boric acid was used instead of (4-(naphthalen-2-yl)phenyl)boric acid.

[0569] MS[M+H] + =714

[0570] <Production Example 2-16> Synthesis of Compound 2-16

[0571] 1) Synthesis of Compound 2-16-A

[0572]

[0573] Compound 2-16-A was produced by the same method as compound 2-1-A except that 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0574] MS[M+H] + =468

[0575] 2) Synthesis of Compound 2-16-B

[0576]

[0577] Compound 2-16-B was produced by the same method as compound 2-1-B except that compound 2-16-A was used instead of compound 2-1-A.

[0578] MS[M+H] + =652

[0579] 3) Synthesis of Compound 2-16

[0580]

[0581] Compound 2-16 was produced by the same method as compound 2-1, except that compound 2-16-B was used instead of compound 2-1-B.

[0582] MS[M+H] + =652

[0583] The synthesis confirmation data of the above compound 2-16 are shown in Fig.14 .

[0584] <Production Example 2-17> Synthesis of Compound 2-17

[0585]

[0586] Compound 2-17 was produced by the same method as compound 2-1, except that compound 2-16-B was used instead of compound 2-1-B and 2-bromonaphthalene was used instead of 1-bromonaphthalene.

[0587] MS[M+H] + =652

[0588] The synthesis confirmation data of the above compound 2-17 are shown in Fig.15 .

[0589] <Production Example 2-18> Synthesis of Compound 2-18

[0590] 1) Synthesis of Compound 2-18-A

[0591]

[0592] Compound 2-18-A was produced by the same method as compound 2-3-A except that 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine.

[0593] MS[M+H] + =512

[0594] 2) Synthesis of Compound 2-18-B

[0595]

[0596] Compound 2-18-B was produced by the same method as compound 2-3-B except that compound 2-18-A was used instead of compound 2-3-A.

[0597] MS[M+H] + =560

[0598] 3) Synthesis of Compound 2-18

[0599]

[0600] Compound 2-18 was produced by the same method as compound 2-3, except that compound 2-18-B was used instead of compound 2-3-B.

[0601] MS[M+H] + =728

[0602] <Production Example 2-19> Synthesis of Compound 2-19

[0603]

[0604] Compound 2-19 was produced by the same method as compound 2-4, except that compound 2-18-B was used instead of compound 2-3-B.

[0605] MS[M+H] + =728

[0606] <Production Example 2-20> Synthesis of Compound 2-20

[0607] 1) Synthesis of Compound 2-20-B

[0608]

[0609] Compound 2-20-B was produced by the same method as compound 2-18-B except that 2-naphthaleneboric acid was used instead of 1-naphthaleneboric acid.

[0610] MS[M+H] + =560

[0611] 2) Synthesis of Compound 2-20

[0612]

[0613] Compound 2-20 was produced by the same method as compound 2-5, except that compound 2-20-B was used instead of compound 2-5-B.

[0614] MS[M+H] + =728

[0615] The synthesis confirmation data of the above compound 2-20 is shown in Fig.16 .

[0616] <Production Example 2-21> Synthesis of Compound 2-21

[0617]

[0618] Compound 2-21 was produced by the same method as Compound 2-20 except that (4-(naphthalen-1-yl)phenyl)boric acid was used instead of (4-(naphthalen-2-yl)phenyl)boric acid.

[0619] MS[M+H] + =728

[0620] <Production Example 2-22> Synthesis of Compound 2-22

[0621]

[0622] Compound 2-22 was produced by the same method as compound 2-16 except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.

[0623] MS[M+H] + =752

[0624] The synthesis confirmation data of the above compound 2-22 are shown in Fig.17 .

[0625] <Production Example 2-23> Synthesis of Compound 2-23

[0626] 1) Synthesis of Compound 2-23-A

[0627]

[0628] Compound 2-23-A was produced by the same method as compound 2-1-A except that (2,5-dichlorophenyl)boric acid was used instead of (3,5-dichlorophenyl)boric acid.

[0629] MS[M+H] + =454

[0630] 2) Synthesis of Compound 2-23-B

[0631]

[0632] Compound 2-23-B was produced by the same method as compound 2-1-B except that compound 2-23-A was used instead of compound 2-1-A.

[0633] MS[M+H]+ =638

[0634] 3) Synthesis of Compound 2-23

[0635]

[0636] Compound 2-23 was produced by the same method as compound 2-1, except that compound 2-23-B was used instead of compound 2-1-B.

[0637] MS[M+H] + =638

[0638] <Production Example 2-24> Synthesis of Compound 2-24

[0639]

[0640] Compound 2-24 was produced by the same method as Compound 2-23, except that 2-bromonaphthalene was used instead of 1-bromonaphthalene.

[0641] MS[M+H] + =638

[0642] <Production Example 2-25> Synthesis of Compound 2-25

[0643]

[0644] Compound 2-25 was produced by the same method as Compound 2-23 except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.

[0645] MS[M+H] + =738

[0646] <Production Example 2-26> Synthesis of Compound 2-26

[0647] 1) Synthesis of Compound 2-26-A

[0648]

[0649] Compound 2-26-A was produced by the same method as compound 2-3-A, except that 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine was used instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine and (2-bromo-4-chlorophenyl)boric acid was used instead of (3-bromo-5-chlorophenyl)boric acid.

[0650] MS[M+H] + =472

[0651] 2) Synthesis of Compound 2-26-B

[0652]

[0653] Compound 2-26-B was produced by the same method as compound 2-3-B except that compound 2-26-A was used instead of compound 2-3-A.

[0654] MS[M+H] + =520

[0655] 3) Synthesis of Compound 2-26

[0656]

[0657] Compound 2-26 was produced by the same method as compound 2-3, except that compound 2-26-B was used instead of compound 2-3-B, and (4-(phenanthrene-9-yl)phenyl)boric acid was used instead of (4-(naphthalen-1-yl)phenyl)boric acid.

[0658] MS[M+H] + =738

[0659] [Example]

[0660] <Example 1-1>

[0661] A glass substrate (Corning 7059 glass) coated with ITO (indium tin oxide) in a thickness of 100 nm was placed in distilled water dissolved with a dispersant and washed with ultrasound. The detergent used was a product of Fischer Co., and the distilled water used was distilled water filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed in sequence with solvents of isopropyl alcohol, acetone, and methanol and dried.

[0662] On the thus prepared ITO transparent electrode, hexanitrilehexaazatriphenylene (HAT-CN) was thermally vacuum deposited to form a 50 nm thick hole injection layer.

[0663] On the hole injection layer, compound HT1 as a substance that transports holes was vacuum-deposited to form a hole transport layer with a thickness of 40 nm.

[0664] On the hole transport layer, H1 and compound 1-1 were vacuum deposited at a weight ratio of 25:1 to form a light-emitting layer with a thickness of 30 nm.

[0665] On the light-emitting layer, compound ET1 was vacuum-deposited to form an electron adjustment layer with a thickness of 3 nm.

[0666] On the electron regulating layer, compound 2-1 and compound LiQ (8-hydroxyquinoline lithium, LithiumQuinolate) were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 35 nm.

[0667] On the electron injection and transport layer, lithium fluoride (LiF) and aluminum were sequentially evaporated to a thickness of 1.2 nm and 200 nm to form a cathode, thereby manufacturing an organic light emitting device.

[0668] During the above process, the evaporation rate of organic matter was maintained at 0.04 nm / s to 0.07 nm / s, the evaporation rate of lithium fluoride was maintained at 0.03 nm / s, and the evaporation rate of aluminum was maintained at 0.2 nm / s. The vacuum degree during evaporation was maintained at 2×10 -7 Up to 5×10 -6 Entrust.

[0669]

[0670] <Examples 1-2 to 1-17>

[0671] An organic light-emitting device was manufactured by the same method as in Example 1-1, except that the compounds shown in Table 1 below were used instead of Compound 1-1 and Compound 2-1, respectively.

[0672] <Comparative Examples 1-1 to 1-17>

[0673] An organic light-emitting device was manufactured by the same method as in Example 1-1, except that the compounds shown in Table 1 below were used instead of Compound 1-1 and Compound 2-1, respectively.

[0674]

[0675]

[0676] The organic light emitting devices of the embodiment and the comparative example were tested at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time required for the luminance to reach 98% relative to the initial luminance (LT98) was measured at a current density of . The results are shown in Table 1 below.

[0677] [Table 1]

[0678]

[0679]

[0680]

Claims

1. An organic light-emitting device, wherein: include: anode; a cathode disposed opposite to the anode; A light-emitting layer having a main body and a dopant between the anode and the cathode, wherein the dopant comprises a compound represented by the following chemical formula 1-1, and the main body comprises a compound represented by the following chemical formula 4; having a hole transport region between the anode and the light-emitting layer; as well as An electron transport region is provided between the cathode and the light-emitting layer and includes a compound represented by the following Chemical Formula 2: Chemical formula 1-1 Chemical formula 4 In Chemical Formula 1-1 and Chemical Formula 4, A, B' and C are each independently a substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic ring having 3 to 30 carbon atoms and containing one or more heteroatoms selected from O, N, Se and S, R' and R" are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted monocyclic aromatic group having 6 to 25 carbon atoms; a substituted or unsubstituted polycyclic aromatic group having 10 to 24 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms and containing one or more heteroatoms selected from O, N, Se and S, and Adjacent groups among R′, R″, A, B′ and C are optionally combined with each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms containing one or more heteroatoms selected from O, N, Se and S, L101 and L102 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted monocyclic arylene group having 6 to 25 carbon atoms; a substituted or unsubstituted polycyclic arylene group having 10 to 24 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms and containing one or more heteroatoms selected from O, N, Se and S, R101 to R108 are the same as or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted silyl group; a substituted or unsubstituted monocyclic aromatic group having 6 to 25 carbon atoms; a substituted or unsubstituted polycyclic aromatic group having 10 to 24 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms and containing one or more heteroatoms selected from O, N, Se and S, Ar101 and Ar102 are the same as or different from each other and are each independently a substituted or unsubstituted monocyclic aromatic group having 6 to 25 carbon atoms; a substituted or unsubstituted polycyclic aromatic group having 10 to 24 carbon atoms; or a substituted or unsubstituted heteroaromatic group having 2 to 60 carbon atoms and containing one or more heteroatoms selected from O, N, Se and S, m1 and m2 are each an integer from 0 to 5, When m1 is 2 or more, L101 are the same as or different from each other, and When m2 is 2 or more, L102 are the same or different from each other. The "substituted or unsubstituted" mentioned herein means substituted by one or more substituents selected from deuterium; alkyl groups having 1 to 50 carbon atoms; silyl groups; amine groups having 1 to 30 carbon atoms; monocyclic aromatic groups having 6 to 25 carbon atoms; polycyclic aromatic groups having 10 to 24 carbon atoms; and heterocyclic groups having 2 to 60 carbon atoms and containing one or more heteroatoms selected from O, N, Se and S, or substituted by a substituent formed by connecting two or more substituents among the substituents, or having no substituents. Chemical formula 2 In chemical formula 2, Two or more of X4 to X6 are N, and the rest are CH, Ar1 and Ar2 are each independently an aryl group having 6 to 30 carbon atoms, substituted or unsubstituted by an alkyl group having 1 to 50 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms, containing one or more heteroatoms selected from O, N, Se and S, substituted or unsubstituted by an alkyl group having 1 to 50 carbon atoms, L is a trivalent aromatic group having 6 to 30 carbon atoms, Y is a polycyclic aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms, n is 2, and When n is 2, two Ys may be the same as or different from each other.

2. The organic light emitting device according to claim 1, wherein: The chemical formula 1-1 is selected from the following structural formulas:

3. The organic light emitting device according to claim 1, wherein: The chemical formula 2 is a compound selected from the following structural formulas:

4. The organic light emitting device according to claim 1, wherein: A weight ratio of the host to the dopant is 90:10 to 99:

1.

5. The organic light emitting device according to claim 1, wherein: The electron transport region includes an electron regulating layer, an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron regulating layer, the electron injection layer, the electron transport layer, or the electron injection and transport layer contains the compound represented by Chemical Formula 2.

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