Compound and organic light-emitting device containing the same

Abstract

The present specification relates to a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

Description

Technical Field

[0001] This specification claims the priority of Korean Patent Application No. 10-2019-0019014 filed in the Korean Intellectual Property Office on February 19, 2019, the entire contents of which are incorporated herein.

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

[0003] Generally speaking, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light-emitting device using the organic light-emitting phenomenon 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. There is a continuous demand for the development of new materials for organic light-emitting devices as described above. Summary of the invention

[0004] Technical issues

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

[0006] Solution to the problem

[0007] The present invention provides a compound represented by the following Chemical Formula 1.

[0008] [Chemical formula 1]

[0009]

[0010] In the above chemical formula 1,

[0011] X1 to X3 are each N or CR 21 , at least one of X1 to X3 is N,

[0012] L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0013] L2 is a direct bond, or a substituted or unsubstituted arylene group,

[0014] R1 and R2 are the same or different from each other and are each independently a substituted or unsubstituted aryl group,

[0015] At least one of R1 and R2 contains an aromatic group having two or more rings condensed,

[0016] R and R 21 are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0017] r is an integer from 1 to 4,

[0018] When r is 2 or more, R is the same or different.

[0019] Ar is a substituted or unsubstituted aryl group having two or more rings condensed.

[0020] In addition, an organic light-emitting device is provided, comprising: a first electrode, a second electrode opposite to the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein one or more of the organic layers contains the compound represented by the chemical formula 1.

[0021] Effects of the Invention

[0022] The compound according to one embodiment of the present specification can be used as a material of an organic layer of an organic light-emitting device, and by using the compound, improved efficiency, lower driving voltage, and / or improved lifespan characteristics can be achieved in the organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figures 1 to 3 An organic light emitting device according to one embodiment of the present specification is illustrated.

[0024] 101: Substrate

[0025] 102: First electrode

[0026] 103: Hole injection layer

[0027] 104: Hole transport layer

[0028] 105: Electron blocking layer

[0029] 106: Luminous layer

[0030] 107: Hole blocking layer

[0031] 108: Electron transport layer

[0032] 109: Electron injection layer

[0033] 110: Second electrode. DETAILED DESCRIPTION

[0034] Next, this specification is described in more detail.

[0035] The present specification provides a compound represented by the above Chemical Formula 1.

[0036] In the compound represented by the above chemical formula 1, in the same benzene ring of dibenzofuran, the ring containing N that acts as an electron acceptor is located at position 3 of dibenzofuran, and the substituted or unsubstituted 2-ring or more condensed aromatic group that acts as an electron donor is substituted at position 1 of dibenzofuran. The electron donor unit and the electron acceptor unit are simultaneously present in the same molecule, which is beneficial to the transmission of holes and electrons. By being located at the meta position, the steric hindrance effect is small compared with the ortho position, and the stability of the material is high. Therefore, when used as a material for the organic layer of an organic light-emitting device, high efficiency and long life can be obtained.

[0037] In the present specification, when a part is indicated to “include / comprise” a certain component, unless there is a particular description to the contrary, it means that other components may be further included, rather than excluding other components.

[0038] In the present specification, when it is mentioned that a certain member is located “on” another member, it includes not only a case where the certain member is in contact with the other member but also a case where other members are present between the two members.

[0039] In the present specification, examples of substituents are described below, but are not limited thereto.

[0040] 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.

[0041] In this specification, the term "substituted or unsubstituted" means that the group is substituted by one or more substituents selected from deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or is substituted by a substituent formed by connecting two or more substituents among the substituents exemplified above, or has no substituent. For example, the "substituent formed by connecting two or more substituents" may be an aryl group substituted by an aryl group, an aryl group substituted by a heterocyclic group, a heterocyclic group substituted by an aryl group, an aryl group substituted by an alkyl group, etc.

[0042] 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 30. Specifically, the number of carbon atoms is preferably 1 to 20. More specifically, the number of carbon atoms is preferably 1 to 10. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, 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-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0043] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, and more preferably a cycloalkyl group having 3 to 20 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

[0044] In this specification, a silyl group may be represented by -SiR 101 R 102 R 103 The chemical formula of R 101 , R 102 and R 103 The silyl groups are identical or different and may be independently hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. The silyl groups specifically include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

[0045] In the present 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 30. Specifically, the number of carbon atoms is preferably 1 to 20. More specifically, the number of carbon atoms is preferably 1 to 10. Specifically, it may be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, an isopropyloxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentyl group, a n-hexyl group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, an n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

[0046] 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-methylanthrylamino, 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.

[0047] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and more preferably an aryl group having 6 to 20 carbon atoms. The above aryl group may be monocyclic or polycyclic. When the above 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 30. More specifically, the number of carbon atoms is preferably 6 to 20. Specifically, as a monocyclic aryl group, phenyl, biphenyl, terphenyl, etc. may be mentioned, but are not limited thereto. When the above 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 30, and more specifically, the number of carbon atoms is preferably 10 to 20. Specifically, as a polycyclic aryl group, naphthyl, anthracenyl, phenanthrenyl, triphenyl, pyrenyl, phenanthrenyl, peryl, yl, fluorenyl, etc., but are not limited to these.

[0048] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0049] When the fluorenyl group is substituted, it may be etc., but not limited thereto.

[0050] In this specification, examples of arylamine groups include substituted or unsubstituted monoarylamine groups, substituted or unsubstituted diarylamine groups, or substituted or unsubstituted triarylamine groups. The aryl group in the above-mentioned arylamine groups may be a monocyclic aryl group or a polycyclic aryl group. The above-mentioned arylamine groups containing more than two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the above-mentioned arylamine groups may be selected from the examples of the above-mentioned aryl groups.

[0051] In the present specification, the heterocyclic group is a heterocyclic group containing one or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 1 to 60. According to one embodiment, the number of carbon atoms in the heterocyclic group is 1 to 30. Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, Azolyl, iso Azolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, Azine, thiazine, di Olefin, triazine, tetrazine, quinolyl Isoquinolyl, quinolyl Quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl naphthyridinyl, triazaindenyl, indolyl, indolyl, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, benzothiazolyl, benzo oxazolyl, benzimidazolyl, benzothiophenyl, benzofuranyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolecarbazolyl, indenocarbazolyl, phenazine, imidazopyridyl, phen Oxazine, phenanthridinyl Phenanthroline, phenothiazine, imidazophenanthridinyl, etc., but not limited thereto.

[0052] In the present specification, the number of atoms constituting the ring of the heterocyclic group is 3 to 25. In another embodiment, the number of atoms constituting the ring of the heterocyclic group is 5 to 17.

[0053] In the present specification, the heteroaryl group is applicable to the above description of the heterocyclic group except that the heteroaryl group is aromatic.

[0054] In the present specification, the above explanations on the aryl group can be applied to the aromatic hydrocarbon ring except that it is a monovalent group.

[0055] In the present specification, an arylene group and a heteroarylene group are divalent groups, and the above descriptions about an aryl group and a heteroaryl group are applicable to each of them except that they are monovalent groups.

[0056] In this specification, "adjacent" groups 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.

[0057] In one embodiment of the present specification, X1 to X3 are each independently N or CR 21 , at least one of X1 to X3 is N.

[0058] In one embodiment of the present specification, X1 and X2 are N.

[0059] In one embodiment of the present specification, the above-mentioned X3 is N.

[0060] In one embodiment of the present specification, the above X3 is CR 21 .

[0061] In one embodiment of the present specification, X1 to X3 are N.

[0062] In one embodiment of the present specification, the above R and R 21 Each is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0063] In one embodiment of the present specification, the above R and R 21 Each is independently hydrogen, deuterium, or substituted or unsubstituted alkyl.

[0064] In one embodiment of the present specification, the above R and R 21 are each independently hydrogen or deuterium.

[0065] In one embodiment of the present specification, the above R and R 21 For hydrogen.

[0066] In one embodiment of the present specification, R1 and R2 are the same as or different from each other and are independently a substituted or unsubstituted aryl group, and at least one of R1 and R2 includes an aryl group having two or more condensed rings.

[0067] In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group, and at least one of R1 and R2 includes an aryl group having two or more condensed rings.

[0068] In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C40 aryl group, and at least one of R1 and R2 includes an aryl group having two or more condensed rings.

[0069] In one embodiment of the present specification, R1 and R2 are the same or different from each other, and are independently a substituted or unsubstituted C6 to C20 aryl group, and at least one of R1 and R2 includes an aryl group having two or more condensed rings.

[0070] In one embodiment of the present specification, R1 and R2 are the same or different from each other and are independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl, and at least one of R1 and R2 contains an aromatic group having two or more condensed rings.

[0071] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, and at least one of R1 and R2 includes a naphthyl group.

[0072] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group, and at least one of R1 and R2 includes a naphthyl group.

[0073] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C40 aryl group, and at least one of R1 and R2 includes a naphthyl group.

[0074] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C20 aryl group, and at least one of R1 and R2 includes a naphthyl group.

[0075] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl, and at least one of R1 and R2 includes naphthyl.

[0076] In one embodiment of the present specification, R1 and R2 are the same or different from each other and are independently phenyl substituted or unsubstituted by naphthyl, biphenyl, or naphthyl substituted or unsubstituted by phenyl, and at least one of R1 and R2 includes naphthyl.

[0077] In one embodiment of the present specification, R1 is a phenyl group, and R2 is a phenyl group substituted with a naphthyl group, or a naphthyl group which may be substituted with a phenyl group.

[0078] In one embodiment of the present specification, R1 is a naphthyl group, and R2 is a phenyl group, a biphenyl group, or a naphthyl group which may be substituted with the naphthyl group.

[0079] In one embodiment of the present specification, the above-mentioned L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0080] In one embodiment of the present specification, the above-mentioned L1 is a direct bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0081] In one embodiment of the present specification, the above-mentioned L1 is a direct bond, or a substituted or unsubstituted C6 to C30 arylene group.

[0082] In one embodiment of the present specification, the above-mentioned L1 is a direct bond, or a substituted or unsubstituted phenylene group.

[0083] In one embodiment of the present specification, the above-mentioned L1 is a direct bond or a phenylene group.

[0084] In one embodiment of the present specification, the above-mentioned L1 is a direct bond.

[0085] In one embodiment of the present specification, the above-mentioned L1 is a phenylene group.

[0086] In one embodiment of the present specification, the above-mentioned L2 is a direct bond, or a substituted or unsubstituted arylene group.

[0087] In one embodiment of the present specification, the above-mentioned L2 is a direct bond, or a substituted or unsubstituted C6 to C40 arylene group.

[0088] In one embodiment of the present specification, the above-mentioned L2 is a direct bond, or a substituted or unsubstituted C6 to C20 arylene group.

[0089] In one embodiment of the present specification, the above-mentioned L2 is a direct bond, or a substituted or unsubstituted phenylene group.

[0090] In one embodiment of the present specification, the above-mentioned L2 is a direct bond or a phenylene group.

[0091] In one embodiment of the present specification, the above-mentioned L2 is a direct bond.

[0092] In one embodiment of the present specification, the above-mentioned L2 is a phenylene group.

[0093] In one embodiment of the present specification, the above-mentioned Ar is a substituted or unsubstituted aryl group having two or more condensed rings.

[0094] In one embodiment of the present specification, Ar is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluoranthenyl group.

[0095] In one embodiment of the present specification, the Ar is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluoranthenyl group.

[0096] In one embodiment of the present specification, Ar is a naphthyl group which may be substituted with an aryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluoranthenyl group.

[0097] In one embodiment of the present specification, Ar is naphthyl, phenanthryl, triphenylene or fluoranthenyl which may be substituted with a phenyl group.

[0098] In one embodiment of the present specification, the compound represented by the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.

[0099] [Chemical formula 1-1]

[0100]

[0101] [Chemical formula 1-2]

[0102]

[0103] [Chemical formula 1-3]

[0104]

[0105] [Chemical formula 1-4]

[0106]

[0107] In the above Chemical Formulae 1-1 to 1-4, the definition of each substituent is the same as that of the above Chemical Formula 1.

[0108] In one embodiment of the present specification, the compound represented by the above Chemical Formula 1 is selected from the following compounds.

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116] In one embodiment of the present specification, an organic light-emitting device is provided, comprising: a first electrode, a second electrode opposite to the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein one or more of the organic layers contains the compound.

[0117] The organic layer of the organic light-emitting device of the present specification may be formed by a single-layer structure, or may be formed by a multilayer structure having two or more organic layers stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers. The organic layer may include one or more layers selected from a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0118] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1.

[0119] In one embodiment of the present specification, the organic layer includes a light-emitting layer. The light-emitting layer includes a host. The host is a compound represented by Chemical Formula 1.

[0120] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the chemical formula 1. The light-emitting layer including the compound represented by the chemical formula 1 may be green or red. For example, the light-emitting layer including the compound represented by the chemical formula 1 has a light-emitting wavelength in the region of 500 nm to 700 nm.

[0121] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may further include a compound represented by the following Chemical Formula 2.

[0122] [Chemical formula 2]

[0123]

[0124] In the above chemical formula 2,

[0125] A is an aromatic hydrocarbon ring,

[0126] L 11 and L 12 are each independently a directly bonded, or substituted or unsubstituted arylene group,

[0127] Ar 11 is a substituted or unsubstituted aryl group,

[0128] Ar 12 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0129] R 11 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0130] n is an integer from 1 to 10,

[0131] When n is 2 or more, R 11 The same as or different from each other.

[0132] In one embodiment of the present specification, A is a monocyclic aromatic hydrocarbon ring.

[0133] In one embodiment of the present specification, A is a benzene ring.

[0134] In one embodiment of the present specification, the above Chemical Formula 2 may be represented by any one of the following Chemical Formulas 2-1 to 2-4.

[0135] [Chemical formula 2-1]

[0136]

[0137] [Chemical formula 2-2]

[0138]

[0139] [Chemical formula 2-3]

[0140]

[0141] [Chemical formula 2-4]

[0142]

[0143] In the above Chemical Formulae 2-1 to 2-4, the definition of each substituent is the same as that of the above Chemical Formula 2.

[0144] In one embodiment of the present specification, L 11 and L12 Each is independently a directly bonded or substituted or unsubstituted C6 to C60 arylene group.

[0145] In one embodiment of the present specification, L 11 and L 12 Each is independently a directly bonded or substituted or unsubstituted C6 to C40 arylene group.

[0146] In one embodiment of the present specification, L 11 and L 12 Each is independently a directly bonded or substituted or unsubstituted C6 to C20 arylene group.

[0147] In one embodiment of the present specification, L 11 and L 12 Each is independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0148] In one embodiment of the present specification, L 11 and L 12 Each is independently a direct bond, a phenylene group or a biphenylene group.

[0149] In one embodiment of the present specification, Ar 11 is a substituted or unsubstituted C6 to C60 aryl group.

[0150] In one embodiment of the present specification, Ar 11 is a substituted or unsubstituted C6 to C40 aryl group.

[0151] In one embodiment of the present specification, Ar 11 is a substituted or unsubstituted C6 to C20 aryl group.

[0152] In one embodiment of the present specification, Ar 11 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group.

[0153] In one embodiment of the present specification, Ar 11 It is a phenyl group, a biphenyl group, a terphenyl group which may be substituted by an aryl group, a naphthyl group which may be substituted by an aryl group, or a fluorenyl group which may be substituted by an alkyl group.

[0154] In one embodiment of the present specification, Ar 12 It is a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C2-C60 heteroaryl group.

[0155] In one embodiment of the present specification, Ar12 It is a substituted or unsubstituted C6 to C40 aryl group, or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0156] In one embodiment of the present specification, Ar 12 It is a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0157] In one embodiment of the present specification, Ar 12 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0158] In one embodiment of the present specification, Ar 12 It is phenyl which may be substituted by an aryl group, biphenyl, terphenyl, naphthyl which may be substituted by an aryl group, fluorenyl which may be substituted by an alkyl group, dibenzofuranyl or dibenzothienyl.

[0159] In one embodiment of the present specification, R 11 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C2 to C60 alkenyl group, a substituted or unsubstituted C2 to C60 alkynyl group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0160] In one embodiment of the present specification, R 11 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C40 cycloalkyl group, a substituted or unsubstituted C6 to C40 aryl group, or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0161] In one embodiment of the present specification, R 11 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0162] In one embodiment of the present specification, R11 is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0163] In one embodiment of the present specification, R 11 is hydrogen, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0164] In one embodiment of the present specification, R 11 For hydrogen.

[0165] In one embodiment of the present specification, the compound represented by the above Chemical Formula 2 may be any one selected from the following compounds.

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] In one embodiment of the present specification, the content ratio (weight ratio) of the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 is 10:90 to 90:10, 30:70 to 70:30, or 50:50 to 70:30.

[0174] In one embodiment of the present specification, the light emitting layer may include the compound represented by the above Chemical Formula 1 and a dopant.

[0175] In one embodiment of the present specification, the dopant may be a fluorescent or phosphorescent dopant.

[0176] In one embodiment of the present specification, the dopant may be a phosphorescent dopant.

[0177] In one embodiment of the present specification, the light emitting layer may include the compound represented by the above Chemical Formula 1 and a metal complex as a phosphorescent dopant.

[0178] In another embodiment, the light emitting layer may include the compound represented by the chemical formula 1 and an iridium (Ir) dopant as a phosphorescent dopant.

[0179] The iridium (Ir) dopant is as follows, but is not limited thereto.

[0180]

[0181]

[0182] When the light-emitting layer includes a dopant, the dopant may be included in an amount of 0.01 to 30 parts by weight, 0.01 to 10 parts by weight, or 0.01 to 5 parts by weight relative to 100 parts by weight of the host.

[0183] In one embodiment of the present specification, the organic layer includes two or more light-emitting layers, and at least one of the two or more light-emitting layers includes the compound represented by the above Chemical Formula 1. The light-emitting layer including the compound represented by the above Chemical Formula 1 is green, and the light-emitting layer not including the compound represented by the above Chemical Formula 1 may include a blue, red or green light-emitting compound known in the art.

[0184] In one embodiment of the present specification, the first electrode is an anode or a cathode.

[0185] In one embodiment of the present specification, the second electrode is a cathode or an anode.

[0186] In one embodiment of the present specification, the organic light-emitting device may be a (normal type) organic light-emitting device having a structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0187] In one embodiment of the present specification, 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 layers, and an anode are sequentially stacked on a substrate.

[0188] For example, the structure of an organic light-emitting device according to one embodiment of the present specification is shown in Figures 1 to 3 . The above Figures 1 to 3 An organic light emitting device is exemplified, but the present invention is not limited thereto.

[0189] Figure 1 The structure of the organic light emitting device is illustrated in which a first electrode 102, a light emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101. The compound represented by the above Chemical Formula 1 is contained in the light emitting layer.

[0190] Figure 2The structure of an organic light-emitting device is illustrated in which a first electrode 102, a hole injection layer 103, a hole transport layer 104, a light-emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101. According to one embodiment of the present invention, the compound represented by the above chemical formula 1 is contained in one or more layers of the above organic layer. According to another embodiment, the compound represented by the above chemical formula 1 is contained in one or more layers of the hole injection layer, the hole transport layer, and the light-emitting layer.

[0191] Figure 3 The structure of an organic light-emitting device is illustrated in which a first electrode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light-emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, and a second electrode 110 are sequentially stacked on a substrate 101. According to one embodiment of the present invention, the compound represented by the above chemical formula 1 is contained in one or more layers of the above organic layer. According to another embodiment, the compound represented by the above chemical formula 1 is contained in one or more layers of the hole injection layer, the hole transport layer, the electron blocking layer, the light-emitting layer, the hole blocking layer, the electron transport layer, and the electron injection layer.

[0192] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that at least one of the organic layers contains the compound, ie, the compound represented by the above Chemical Formula 1.

[0193] When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0194] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. In this case, the manufacturing can be performed as follows: a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation is used to vapor-deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode substance, an organic layer, and an anode substance on a substrate.

[0195] In addition, the compound represented by the above chemical formula 1 can be used to form an organic layer by not only vacuum evaporation but also solution coating when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0196] 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.

[0197] 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. For example, there are 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, etc., but not limited to these.

[0198] In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function, such as 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 not limited thereto.

[0199] The above-mentioned light-emitting layer may include a host material and a dopant material. The host material includes an aromatic fused ring derivative or a heterocyclic compound. Specifically, as an aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0200] As the dopant material, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamine. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as a metal complex, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0201] In the present specification, when the compound represented by the above chemical formula 1 is contained in an organic layer other than the light-emitting layer, the light-emitting substance of the light-emitting layer is a substance that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine them to emit light in the visible light region, and a substance with high quantum efficiency for fluorescence or phosphorescence is suitable. In addition, when there is a light-emitting layer including the compound represented by the above chemical formula 1 and an additional light-emitting layer, the light-emitting substance of the additional light-emitting layer is also preferably the above-mentioned substance.

[0202] As the above-mentioned luminescent material, for example, there are 8-hydroxyquinoline aluminum complex (Alq3), carbazole compounds, dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo The present invention includes, but is not limited to, oxazole, benzothiazole and benzimidazole compounds; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene; rubrene, etc.

[0203] The hole injection layer is a layer that receives holes from the electrode. The hole injection material is preferably a material that has the ability to transport holes, has the effect of receiving holes from the anode, and has an excellent hole injection effect for the light-emitting layer or the light-emitting material. In addition, it is preferably a material that has an excellent ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. And, it is preferably a material with excellent thin film forming ability. In addition, it is preferred that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, and arylamine organics; hexanitrile hexaazatriphenylene organics; quinacridone organics; perylene organics; polythiophene conductive polymers such as anthraquinone and polyaniline, etc., but are not limited to these.

[0204] The hole transport layer is a layer that receives holes from the hole injection layer and transports 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, and a material with a large hole mobility is suitable. As specific examples, there are arylamine organic substances, conductive polymers, and block copolymers having both conjugated parts and non-conjugated parts, but are not limited to these.

[0205] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, preferably a material 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 together with any desired cathode material as used in the prior art. In particular, a suitable cathode material is a common material having a low work function and accompanied by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, etc., in each case accompanied by an aluminum layer or a silver layer.

[0206] The electron injection layer is a layer that receives electrons from the electrode. As the electron injection material, the following materials are preferred: materials that have excellent ability to transport electrons, have the effect of receiving electrons from the cathode, and have excellent electron injection effect on the light-emitting layer or the light-emitting material. In addition, materials that prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer and have excellent thin film forming ability are preferred. 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.

[0207] 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.

[0208] The electron blocking layer is a layer that prevents the electrons injected from the electron injection layer from entering the hole injection layer through the light-emitting layer, thereby improving the life and efficiency of the device. Known materials can be used without restriction, and can be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and the layer that simultaneously performs hole injection and hole transport. 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 electron injection layer. Specifically, there are Examples of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

[0209] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0210] The organic light-emitting device of the present invention can be manufactured using the above-mentioned compound to form one or more organic layers, and can also be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0211] Modes for Carrying Out the Invention

[0212] The method for producing the compound of the above Chemical Formula 1 and the production of an organic light-emitting device using the same are specifically described in the following examples. However, the following examples are used to illustrate the present invention, and the scope of the present invention is not limited thereto.

[0213] [Synthesis example]

[0214] Synthesis Example 1: Synthesis of Compound 1

[0215] Step 1) Synthesis of compound 1-1

[0216]

[0217] Under a nitrogen atmosphere, 1-bromo-3-chlorodibenzo[b,d]furan (15.0 g, 53.3 mmol) and naphthalene-2-ylboronic acid (10.1 g, 58.6 mmol) were added to 300 ml of THF (tetrahydrofuran), stirred and refluxed. Then, potassium carbonate (29.5 g, 213.1 mmol) was dissolved in 88 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.8 g, 1.6 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 10.7 g of compound 1-1 (yield 61%, MS[M+H] + =330).

[0218] Step 2) Synthesis of compound 1-2

[0219]

[0220] Under nitrogen atmosphere, compound 1-1 (15.0 g, 45.6 mmol) and bis(pinacolato)diboron (12.7 g, 50.2 mmol) were added to 300 ml of 1,4-dihydro-1-[2-(2-piperidinol)-1-yl] ... alkane, reflux and stir. Then, potassium acetate (6.7 g, 68.4 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium (0) (0.8 g, 1.4 mmol) and tricyclohexylphosphine (0.8 g, 2.7 mmol) were added. The reaction was allowed to react for 8 hours, cooled to room temperature, and the organic layer was separated by chloroform and water, and then the organic layer was distilled. The obtained product was dissolved in chloroform again, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 11.7 g of compound 1-2 (yield 61%, MS [M + H] + =421).

[0221] Step 3) Synthesis of Compound 1

[0222]

[0223] Under nitrogen atmosphere, compound 1-2 (15.0 g, 35.7 mmol) and 2-chloro-4-(naphthalene-2-yl)-6-phenyl-1,3,5-triazine (12.5 g, 39.3 mmol) were added to 300 ml of THF, stirred and refluxed. Then, potassium carbonate (19.7 g, 142.7 mmol) was dissolved in 59 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.2 g, 1.1 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was dissolved in chloroform again, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. After the concentrated compound was purified by silica gel column chromatography, 6.2 g of compound 1 (yield 30%, MS [M+H]) was produced by sublimation purification. + =577).

[0224] Synthesis Example 2: Synthesis of Compound 2

[0225]

[0226] In Synthesis Example 1, except that 2-chloro-4-phenyl-6-(7-phenylnaphthalen-2-yl)-1,3,5-triazine was used instead of 2-chloro-4-phenyl-6-(7-phenylnaphthalen-2-yl)-1,3,5-triazine, Compound 2 (MS[M+H] + =653).

[0227] Synthesis Example 3: Synthesis of Compound 3

[0228]

[0229] In Synthesis Example 1, except that naphthalene-2-ylboronic acid was replaced with naphthalene-1-ylboronic acid and 2-chloro-4-(naphthalene-2-yl)-6-phenyl-1,3,5-triazine was replaced with 2-chloro-4,6-di(naphthalene-2-yl)-1,3,5-triazine, a compound 3 (MS[M+H] + =627).

[0230] Synthesis Example 4: Synthesis of Compound 4

[0231]

[0232] In Synthesis Example 1, except that naphthalene-2-ylboronic acid was replaced with phenanthrene-9-ylboronic acid and 2-chloro-4-(naphthalene-2-yl)-6-phenyl-1,3,5-triazine was replaced with 2-chloro-4-(4-(naphthalene-2-yl)phenyl)-6-phenyl-1,3,5-triazine, a compound 4 (MS[M+H] + =703).

[0233] Synthesis Example 5: Synthesis of Compound 5

[0234]

[0235] In Synthesis Example 1, except that naphthalene-2-ylboronic acid was replaced with triphenylene-2-ylboronic acid and 2-chloro-4-(naphthalene-2-yl)-6-phenyl-1,3,5-triazine was replaced with 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(naphthalene-2-yl)-1,3,5-triazine, a compound 5 (MS[M+H] + =753).

[0236] Synthesis Example 6: Synthesis of Compound 6

[0237]

[0238] Compound 6 (MS[M+H] + =653).

[0239] Synthesis Example 7: Synthesis of Compound 7

[0240]

[0241] In Synthesis Example 1, 2-naphthalene-2-ylboric acid was replaced with fluoranthene-3-ylboric acid, and 2-chloro-4-(naphthalene-2-yl)-6-phenyl-1,3,5-triazine was replaced with 2-chloro-4-phenyl-6-(4-phenylnaphthalene-1-yl)-1,3,5-triazine. Compound 7 (MS [M + H]) was prepared by the same preparation method as the preparation method of Compound 1. + =727).

[0242] [Experimental example]

[0243] Experimental Example 1-1

[0244] ITO (Indium Tin Oxide) The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0245] On the ITO transparent electrode prepared in this way, the following HI-A and hexanitrile hexaazatriphenylene (HAT-CN) were sequentially added at The hole injection layer was formed by thermal vacuum deposition of a thickness of 1000 mm / s. On the hole injection layer, as a hole transport layer, the following HT-A was deposited in the amount of 1000 mm / s. After vacuum evaporation with a thickness of 1000 mm, the following EB-A was deposited as an electron blocking layer. On the electron blocking layer, the compound 1 prepared above and the following RD compound were deposited at a weight ratio of 97:3 and The following ET-A and Liq were added in a ratio of 1:1 and The thickness of the thermal vacuum deposition, then Liq The electron transport and injection layer is formed by vacuum evaporation of a thickness of 1:1. On the electron injection layer, magnesium and silver are deposited in a weight ratio of 1:4 and A cathode is formed by evaporation with a thickness of , thereby manufacturing an organic light-emitting device.

[0246]

[0247] In the above process, the evaporation rate of organic matter is maintained at Lithium fluoride at cathode maintains The evaporation rate of silver and magnesium is maintained The evaporation speed is 2×10 -7 Up to 5×10 -6 A support is provided to produce an organic light-emitting device.

[0248] Experimental Examples 1-2 to 1-7

[0249] An organic light-emitting device was manufactured by the same method as in Experimental Example 1-1, except that the compounds described in Table 1 below were used instead of Compound 1.

[0250] Comparative Experimental Examples 1-1 to 1-8

[0251] An organic light-emitting device was manufactured by the same method as in Experimental Example 1-1, except that the compounds described in Table 1 below were used instead of Compound 1. Compounds RH-A, RH-B, RH-C, RH-D, RH-E, RH-F, RH-G, and RH-H in Table 1 below are respectively as follows.

[0252]

[0253] Experimental Examples 2-1 to 2-4

[0254] An organic light-emitting device was manufactured by the same method as in Experimental Example 1-1, except that the compounds listed in Table 1 below were used instead of Compound 1. The ratio of each compound in Table 1 below refers to a weight ratio, and compounds PRH-1 and PRH-2 are shown below.

[0255]

[0256] Comparative Experimental Examples 2-1 to 2-4

[0257] An organic light-emitting device was manufactured by the same method as in Experimental Example 1-1 except that the compounds described in Table 1 below were used instead of Compound 1. The ratio of each compound in Table 1 below refers to a weight ratio, and compounds RH-A, RH-D, RH-B, RH-G, PRH-1, and PRH-2 are the same as described above.

[0258] The organic light-emitting devices manufactured in the above experimental examples and comparative experimental examples were stored in an oven at 100°C for 30 minutes for heat treatment, and then current was applied to measure voltage, efficiency, and life (T95). The results are shown in Table 1 below. At this time, the voltage and efficiency were measured by applying 10 mA / cm 2 In addition, T95 in Table 1 below refers to the current density of 20 mA / cm 2 The time it takes for the initial brightness to drop to 95% is measured.

[0259] [Table 1]

[0260]

[0261]

[0262] The compound represented by Chemical Formula 1 has the following structure: a nitrogen-containing heterocyclic ring that acts as an electron acceptor is bonded to the 3rd position of dibenzofuran, and two or more fused aromatic groups are connected to it in the meta direction. In particular, two or more fused aromatic groups are also connected to the nitrogen-containing heterocyclic ring, so that there are two or more fused aromatic groups in the structure, and compared with the structure having only one fused aromatic group such as RH-A and RH-B, the glass transition temperature is increased and the thermal stability of the film state is increased. For devices that use the structures of RH-A and RH-B, during heat treatment, the molecular arrangement can be changed in the film due to the lower glass transition temperature, resulting in an increase in the voltage of the device and a decrease in efficiency and life, as shown in Table 1.

[0263] In the case of the pyrene ring of RH-E, high thermal stability is shown, but the triplet energy is too low, which is not conducive to energy transfer to the dopant and reduces efficiency. Therefore, it can be seen that if the triplet energy is not too low and high thermal stability is desired, two or more appropriate fused aromatic groups need to be located in the structure as shown in Chemical Formula 1.

[0264] When the fused aromatic group is a fused heteroaromatic group, as in RH-C and RH-D, it is known that the electron transport ability of the molecule is reduced, thereby the charge balance inside the device is disrupted and the device characteristics are reduced. In addition, when it is bound at the ortho position, as in RH-G, the binding force with dibenzofuran is weakened by the interaction between the two substituents, thereby showing a reduced device life. The 2nd position of dibenzofuran is a vacant position of LUMO, and the structure such as RH-H that binds triazine at this position cannot transfer electrons between dibenzofuran and triazine, so as shown in Comparative Experimental Examples 1-8, it can be seen that all device characteristics are significantly reduced.

[0265] In particular, as in Experimental Examples 2-1 to 2-4, when the compound represented by Chemical Formula 2 is used as a host to form an exciplex, the overall device characteristics are improved. In this case, it can also be confirmed that the compound of Chemical Formula 1 more obviously shows the characteristic effects of low voltage, high efficiency, and long life.

Claims

1. A compound represented by the following chemical formula 1: Chemical formula 1 in, In the chemical formula 1, X1 to X3 are each N, L1 is direct bonding, L2 is a directly bonded or unsubstituted phenylene group, R1 and R2 are the same as or different from each other and are each independently a phenyl group which may be substituted or unsubstituted by a naphthyl group, an unsubstituted biphenyl group, or a naphthyl group which may be substituted or unsubstituted by a phenyl group, wherein at least one of R1 and R2 comprises a naphthyl group, R is hydrogen, r is 4, and Ar is naphthyl which may be substituted with phenyl, unsubstituted phenanthryl, unsubstituted triphenylene or unsubstituted fluoranthenyl.

2. The compound according to claim 1, wherein The compound represented by the chemical formula 1 is any one selected from the following compounds:

3. An organic light-emitting device, wherein: include: A first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound according to claim 1 or 2.

4. The organic light emitting device according to claim 3, wherein: The organic layer includes a light-emitting layer, and the light-emitting layer contains the compound.

5. The organic light emitting device according to claim 3, wherein: The organic layer includes a light-emitting layer, the light-emitting layer includes a host substance, and the host substance includes the compound.

6. The organic light emitting device according to claim 4, wherein: The light-emitting layer further comprises a compound represented by the following Chemical Formula 2: Chemical formula 2 In the chemical formula 2, A is a C6 to C30 aromatic hydrocarbon ring, L 11 and L 12 are each independently a directly bonded or unsubstituted C6 to C60 arylene group, Ar 11 is a C6 to C60 aryl group which is substituted or unsubstituted by a C1 to C30 alkyl group or a C6 to C30 aryl group, Ar 12 is a C1 to C30 alkyl group or a C6 to C30 aryl group which may be substituted or unsubstituted, a C6 to C60 aryl group, or an unsubstituted C2 to C60 heteroaryl group, R 11 is hydrogen, and n is 10.

7. The organic light emitting device according to claim 6, wherein: The chemical formula 2 is represented by any one of the following compounds:

8. The organic light emitting device according to claim 3, wherein: The organic layer includes one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.

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