Compound and organic electronic device comprising same

Abstract

The present disclosure relates to a compound represented by the following Chemical Formula 1 and an organic electronic device comprising the same. The compound is used in an organic electronic device, can reduce the driving voltage of the organic electronic device and improve the light efficiency, and can improve the lifespan characteristics of the device through the thermal stability of the compound. [Chemical Formula 1] # imgabs0 #

Description

[0001] This application is a divisional application of an application with an application date of September 23, 2016, application number 201680022747.4, and invention name “Compounds and organic electronic devices containing the same” (PCT / KR2016 / 010648, national phase entry date October 19, 2017). Technical Field

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2015-0135770 filed on September 24, 2015, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

[0003] The present description relates to compounds and organic electronic devices comprising the same. Background Art

[0004] Representative examples of organic electronic devices include organic light-emitting devices. In general, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic materials. An organic light-emitting device utilizing the organic light-emitting phenomenon generally has a structure including a positive electrode, a negative electrode, and an organic material layer therebetween. Here, in many cases, the organic material layer may have a multilayer structure composed of different materials to improve the efficiency and stability of the organic light-emitting device, for example, the organic material layer may be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light-emitting device, if a voltage is applied between the two electrodes, holes are injected into the organic material layer from the positive electrode and electrons are injected into the organic material layer from the negative electrode, and excitons are formed when the injected holes and electrons meet each other, and light is emitted when the excitons fall into the ground state again.

[0005] There is a constant demand for the development of new materials for the above-mentioned organic light-emitting devices. Summary of the invention

[0006] Technical issues

[0007] The present specification is directed to providing compounds and organic electronic devices comprising the same.

[0008] Technical Solution

[0009] This specification provides a compound represented by the following Chemical Formula 1.

[0010] [Chemical formula 1]

[0011]

[0012] In Chemical Formula 1,

[0013] L1 to L3 are the same as or different from each other, and are each independently a direct bond, or a substituted or unsubstituted arylene group,

[0014] Ar1 and Ar2 are the same as or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group,

[0015] R1 to R8 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,

[0016] R9 and R 10 are the same as or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

[0017] p and q are integers from 1 to 4,

[0018] When p is 2 or more, a plurality of R9 are the same as or different from each other, and

[0019] When q is 2 or greater, multiple R 10 The same as or different from each other.

[0020] In addition, the present specification provides an organic electronic device including: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contains the compound of Chemical Formula 1.

[0021] Beneficial Effects

[0022] The compound according to an exemplary embodiment of the present specification is used for an organic electronic device (including an organic light emitting device), and thus can reduce the driving voltage of the organic electronic device and improve light efficiency, as well as improve the lifespan characteristics of the device through the thermal stability of the compound. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figure 1 An organic light emitting device 10 according to an exemplary embodiment of the present specification is shown.

[0024] Figure 2 An organic light emitting device 11 according to another exemplary embodiment of the present specification is shown.

[0025] [Explanation of Reference Numerals]

[0026] 10, 11: Organic light-emitting devices

[0027] 20: Base

[0028] 30: First electrode

[0029] 40: Luminous layer

[0030] 50: Second electrode

[0031] 60: Hole injection layer

[0032] 70: Hole transport layer

[0033] 80: Electron transport layer

[0034] 90: Electron injection layer DETAILED DESCRIPTION

[0035] Hereinafter, the present specification will be described in more detail.

[0036] The present specification provides a compound represented by Chemical Formula 1.

[0037] According to an exemplary embodiment of the present specification, the compound represented by Chemical Formula 1 has a structure in which carbazole is substituted at the ortho position of the benzene ring, and compared with the structure in which carbazole is substituted at the meta and para positions of the benzene ring, since the structure is in a state of conjugation breakage, the compound has a structure in which HOMO and LUMO values ​​are relatively easily adjusted according to the type of the substituent due to a large band gap. Therefore, when the compound represented by Chemical Formula 1 is synthesized to perform device evaluation on a hole injection layer, a hole transport layer, or an electron blocking layer, the driving voltage of the organic electronic device can be reduced and the light efficiency can be further improved.

[0038] In this manual, Refers to the part to be connected.

[0039] Examples of the substituent in the present specification will be described below, but are not limited thereto.

[0040] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of substitution is not limited as long as the position is a position where the hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more are substituted, the two or more substituents may be the same as or different from each other.

[0041] In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the following: deuterium, halogen group, cyano group, nitro group, imide group, amino group, silyl group, boron group, hydroxyl group, carbonyl group, alkyl group, cycloalkyl group, alkenyl group, alkoxy group, aryloxy group, alkylthio group, arylthio group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, heteroaryl group, amine group, alkylamine group, aralkylamine group, heteroarylamine group, arylamine group, phosphoryl group, arylphosphine group, phosphine oxide group, or heteroaryl group containing one or more of N, O, S, Se and Si atoms, or substituted with a substituent connected by two or more substituents in the exemplified substituents; or having no substituent. For example, "a substituent connected by two or more substituents" may be a biphenyl group. That is, the biphenyl group may also be an aryl group, and may be interpreted as a substituent connected by two phenyl groups. Biphenyl means a substituent in which two aryl groups are connected, but the "substituent in which two or more substituents are connected" may also be a substituent in which two or more different substituents are connected. For example, the "substituent in which two or more substituents are connected" may be a phenyl substituted with pyridyl, which is a substituent in which pyridyl and phenyl are connected; or a phenyl substituted with quinolyl, which is a substituent in which quinolyl and phenyl are connected; or a phenyl substituted with cyano, which is a substituent in which cyano and phenyl are connected.

[0042] In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

[0043] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 50. Specific examples thereof 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, 5-methylhexyl and the like, but are not limited thereto.

[0044] In the present specification, the cycloalkyl group is not particularly limited, but a cycloalkyl group having 3 to 30 carbon atoms is preferred, and specific examples thereof include 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.

[0045] In the present specification, specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but are not limited thereto.

[0046] In the present specification, the aryl group is not particularly limited but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0047] When the aryl group is a monocyclic aryl group, the number of carbon atoms thereof is not particularly limited, but is preferably 6 to 30. Specific examples of the monocyclic aryl group include phenyl, biphenyl, terphenyl and the like, but are not limited thereto.

[0048] When the aryl group is a polycyclic aryl group, the number of carbon atoms thereof is not particularly limited, but is preferably 10 to 30. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthrenyl, triphenyl, pyrenyl, peryl, fluorenyl, etc., but are not limited thereto.

[0049] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0050] When the fluorenyl group is substituted, the fluorenyl group may be etc. However, the fluorenyl group is not limited thereto.

[0051] In the present specification, an "adjacent" group may mean: a substituent that replaces an atom directly connected to the atom replaced by the corresponding substituent, a substituent that is located closest to the corresponding substituent in space, or another substituent that replaces the atom replaced by the corresponding substituent. For example, two substituents substituted at the ortho position of a benzene ring and two substituents replacing the same carbon in an aliphatic ring may be interpreted as groups "adjacent" to each other.

[0052] In the present specification, the case where adjacent groups are combined with each other to form a ring means that adjacent groups are combined with each other to form a 5-membered to 8-membered hydrocarbon ring or a 5-membered to 8-membered heterocycle as described above, and the ring may be a monocyclic or polycyclic ring, and may be an aliphatic ring, an aromatic ring or a condensed form thereof, and is not limited thereto.

[0053] In the present specification, the hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic ring and an aliphatic ring, and may be selected from examples of the cycloalkyl group or the aryl group, except for a non-monovalent hydrocarbon ring.

[0054] In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from the examples of the aryl group except for a non-monovalent aromatic ring.

[0055] In the present specification, the above description about the aryl group can be applied to the arylene group, except that the arylene group is a divalent group.

[0056] According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, or a substituted or unsubstituted arylene group.

[0057] According to an exemplary embodiment of the present specification, L1 to L3 are substituted or unsubstituted arylene groups having 6 to 60 carbon atoms.

[0058] According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, or a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluorenyl group.

[0059] According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, or a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthrylene group, a phenanthrenyl group, a trimphenylene group, or a fluorenyl group.

[0060] According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, or a phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrenyl, triphenylene, or fluorenyl group that is unsubstituted or substituted with deuterium, an alkyl, a silyl, a cyano, or a halogen group.

[0061] According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, or a phenylene group or a biphenylene group which is unsubstituted or substituted with a deuterium, an alkyl group, a silyl group, a cyano group, or a halogen group.

[0062] According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, or a substituted or unsubstituted fluorenylene group.

[0063] According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, or a substituted or unsubstituted spirobifluorenylene group.

[0064] According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, or

[0065] According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitrile group, a nitro group, a silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group.

[0066] According to an exemplary embodiment of the present specification, Ar1 and Ar2 are unsubstituted aryl groups having 6 to 60 carbon atoms.

[0067] According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenyl group, or a substituted or unsubstituted fluorenyl group.

[0068] According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, or a fluorenyl group.

[0069] According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, or a triphenyl group which is unsubstituted or substituted with a deuterium, an alkyl group, a silyl group, a cyano group, or a halogen group.

[0070] According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group or a biphenyl group which is unsubstituted or substituted with a deuterium, an alkyl group, a silyl group, a cyano group, or a halogen group.

[0071] According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted triphenyl group.

[0072] According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted fluorenyl group.

[0073] According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted spirobifluorenyl group.

[0074] According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently

[0075] According to an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are combined with an adjacent group to form a substituted or unsubstituted ring.

[0076] According to an exemplary embodiment of the present specification, R1 to R8 are substituted or unsubstituted aryl groups having 6 to 20 carbon atoms.

[0077] According to an exemplary embodiment of the present specification, R1 to R8 are hydrogen.

[0078] According to an exemplary embodiment of the present specification, R1 and R2, R2 and R3, or R3 and R4 are combined with each other to form a substituted or unsubstituted ring.

[0079] According to an exemplary embodiment of the present specification, R1 and R2, R2 and R3, or R3 and R4 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

[0080] According to an exemplary embodiment of the present specification, R9 and R 10 are the same as or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0081] According to an exemplary embodiment of the present specification, R9 and R 10 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0082] According to an exemplary embodiment of the present specification, R9 and R 10 For hydrogen.

[0083] According to an exemplary embodiment of the present specification, p and q are integers of 1 to 4.

[0084] According to an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2 to 4.

[0085] [Chemical formula 2]

[0086]

[0087] [Chemical formula 3]

[0088]

[0089] [Chemical formula 4]

[0090]

[0091] In Chemical Formulas 2 to 4,

[0092] L1 to L3, Ar1, Ar2, R1 to R 10 , p and q are the same as those defined in Chemical Formula 1,

[0093] R' is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

[0094] r is an integer from 1 to 4, and

[0095] When r is 2 or more, a plurality of R's are the same as or different from each other.

[0096] According to an exemplary embodiment of the present specification, the compound represented by Chemical Formula 1 is represented by any one of the following compounds.

[0097]

[0098]

[0099]

[0100]

[0101]

[0102] The compound according to an exemplary embodiment of the present specification may be prepared based on the preparation examples described below, and the core structure of the compound according to an exemplary embodiment of the present specification may be prepared through reaction formulas 1 to 3 described below, but is not limited thereto.

[0103] [Reaction 1]

[0104]

[0105] [Reaction 2]

[0106]

[0107] [Reaction 3]

[0108]

[0109] In reaction formulas 1 to 3, L1 to L3, Ar1, Ar2, R1 to R 10 , p and q are the same as those defined in Chemical Formula 1.

[0110] Furthermore, the present specification provides an organic electronic device including the above-mentioned compound.

[0111] An exemplary embodiment of the present application provides an organic electronic device, which includes: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contains the compound.

[0112] In this specification, when one member is disposed “on” another member, this includes not only a case in which one member is made to contact another member but also a case in which another member exists between the two members.

[0113] In the present specification, when a component “includes” a constituent element, unless otherwise explicitly described, this does not mean excluding another constituent element but means that another constituent element may further be included.

[0114] The organic electronic device may be selected from: an organic light emitting device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.

[0115] The organic material layer of the organic electronic device of the present specification may also be composed of a single-layer structure, and may be composed of a multilayer structure in which two or more organic material layers are stacked. For example, the organic electronic device of the present specification 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 an organic material layer. However, the structure of the organic electronic device is not limited thereto, and may include a smaller number of organic layers.

[0116] In an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or the layer that simultaneously injects and transports holes includes the compound of Chemical Formula 1.

[0117] According to an exemplary embodiment of the present specification, the organic material layer includes an electron blocking layer, and the electron blocking layer includes a compound represented by Chemical Formula 1.

[0118] According to another exemplary embodiment, the organic electronic device may be an organic electronic device having a structure (normal type) in which a positive electrode, one or more organic material layers, and a negative electrode are sequentially stacked on a substrate.

[0119] According to still another exemplary embodiment, the organic electronic device may be an organic electronic device having a reverse structure (inverted type) in which a negative electrode, one or more organic material layers, and a positive electrode are sequentially stacked on a substrate.

[0120] For example, the structure of the organic light-emitting device of the present specification may have the following Figure 1 and 2 The structure shown in, but not limited to this.

[0121] Figure 1 The structure of the organic light emitting device 10 is illustrated, in which the first electrode 30 , the light emitting layer 40 , and the second electrode 50 are sequentially stacked on the substrate 20 . Figure 1 is an exemplary structure of an organic light emitting device according to an exemplary embodiment of the present specification, and it may further include other organic material layers.

[0122] Figure 2 The structure of an organic light emitting device is illustrated in which a first electrode 30 , a hole injection layer 60 , a hole transport layer 70 , a light emitting layer 40 , an electron transport layer 80 , an electron injection layer 90 , and a second electrode 50 are sequentially stacked on a substrate 20 . Figure 2 is an exemplary structure according to the exemplary embodiment of the present specification, and it may further include other organic material layers.

[0123] According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following Chemical Formula 1-A.

[0124] [Chemical Formula 1-A]

[0125]

[0126] In Chemical Formula 1-A,

[0127] n1 is an integer of 1 or greater,

[0128] Ar7 is a substituted or unsubstituted monovalent or higher valent benzofluorenyl group, a substituted or unsubstituted monovalent or higher valent fluoranthene group, a substituted or unsubstituted monovalent or higher valent pyrenyl group, or a substituted or unsubstituted monovalent or higher valent base,

[0129] L4 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0130] Ar8 and Ar9 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted arylalkyl group, or a substituted or unsubstituted heteroaryl group, or may be combined with each other to form a substituted or unsubstituted ring, and

[0131] When n1 is 2 or more, two or more structures in the brackets are the same as or different from each other.

[0132] According to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1-A as a dopant of the light-emitting layer.

[0133] According to an exemplary embodiment of the present specification, L4 is a direct bond.

[0134] According to an exemplary embodiment of the present specification, n1 is 2.

[0135] In an exemplary embodiment of the present specification, Ar7 is a divalent pyrene group which is unsubstituted or substituted with deuterium, a methyl group, an ethyl group, or a tert-butyl group.

[0136] According to an exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0137] According to an exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and are each independently an aryl group which is unsubstituted or substituted with a germanium group substituted with an alkyl group.

[0138] According to an exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and are each independently an aryl group which is unsubstituted or substituted with a trimethylgermanyl group.

[0139] According to an exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group.

[0140] According to an exemplary embodiment of the present specification, Ar8 and Ar9 are a phenyl group which is unsubstituted or substituted with a trimethylgermanyl group.

[0141] According to an exemplary embodiment of the present specification, Chemical Formula 1-A is represented by the following compounds.

[0142]

[0143] According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following Chemical Formula 2-A.

[0144] [Chemical Formula 2-A]

[0145]

[0146] In Chemical Formula 2-A,

[0147] G 11is 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1-naphthyl, 2-naphthyl, 9-naphthyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, or the following chemical formula

[0148] G 12 is phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1-naphthyl, 2-naphthyl, 9-naphthyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl 1-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1-anthracenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, or 3-fluoranthenyl,

[0149] G 13 and G 14 are the same as or different from each other and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0150] g 12 is an integer from 1 to 5,

[0151] g 13 and g 14 are each an integer from 1 to 4, and

[0152] When 12 tog 14 When each is 2 or more, two or more structures in the brackets are the same as or different from each other.

[0153] According to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 2-A as a host of the light-emitting layer.

[0154] According to an exemplary embodiment of the present specification, G 11 It is 1-naphthyl.

[0155] According to an exemplary embodiment of the present specification, G 12 It is 2-naphthyl.

[0156] According to an exemplary embodiment of the present specification, G 13 and G 14 For hydrogen.

[0157] According to an exemplary embodiment of the present specification, Chemical Formula 2-A is represented by the following compounds.

[0158]

[0159] The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that one or more layers of the organic material layers contain the heterocyclic compound of the present specification, ie, the compound represented by Chemical Formula 1.

[0160] When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0161] For example, the organic light-emitting device of the present specification can be manufactured by stacking a first electrode, an organic material layer, and a second electrode on a substrate in sequence. In this case, the organic light-emitting device can be manufactured as follows: a metal, or a conductive metal oxide or an alloy thereof is deposited on a substrate to form a first electrode by using a physical vapor deposition (PVD) method (e.g., sputtering or electron beam evaporation), and an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the first electrode, and then a material that can be used as a second electrode is deposited on the organic material layer. In addition to the method described above, the organic light-emitting device can also be manufactured by depositing a negative electrode material, an organic material layer, and a first electrode on a substrate in sequence. In addition, when manufacturing an organic light-emitting device, the compound represented by Chemical Formula 1 can be formed into an organic material layer not only by a vacuum deposition method but also by a solution coating method. Here, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roller coating, etc., but is not limited thereto.

[0162] In addition to the method described above, an organic light emitting device can also be manufactured by depositing a negative electrode material, an organic material layer, and a positive electrode material in sequence on a substrate (International Publication No. 2003 / 012890). However, the manufacturing method is not limited thereto.

[0163] According to an exemplary embodiment of the present specification, the first electrode is a positive electrode, and the second electrode is a negative electrode.

[0164] According to another exemplary embodiment of the present specification, the first electrode is a negative electrode, and the second electrode is a positive electrode.

[0165] As the positive electrode material, a material having a large work function is generally preferred to smoothly inject holes into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and 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 are not limited thereto.

[0166] As the negative electrode material, a material having a small work function is generally preferred to smoothly inject electrons into the organic material layer. Specific examples of the negative electrode material 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 and Mg / Ag, etc., but are not limited thereto.

[0167] The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, so it has a hole injection effect in the positive electrode, has an excellent hole injection effect on the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and also has excellent film forming ability. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, conductive polymers based on polyaniline and polythiophene, etc., but are not limited thereto.

[0168] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is suitably a material that can receive holes from the positive electrode or the hole injection layer to transfer the holes to the light-emitting layer and has high mobility for the holes. Specific examples thereof include organic materials based on arylamine, conductive polymers, block copolymers having both conjugated and non-conjugated parts, etc., but are not limited thereto.

[0169] The electron blocking layer is a layer that can improve the life and efficiency of the device by preventing holes injected from the hole injection layer from passing through the light-emitting layer and entering the electron injection layer, and if necessary, it can be formed in an appropriate portion between the light-emitting layer and the electron injection layer using a known material.

[0170] The light-emitting material of the light-emitting layer is a material that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine the holes and electrons to emit light in the visible light region, and is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include: 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; diphenylethylene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo-based Compounds of oxazole, benzothiazole and benzimidazole; polymers based on poly(p-phenylenevinylene) (PPV); spiro compounds; polyfluorene, rubrene, etc., but are not limited thereto.

[0171] The light-emitting layer may include a host material and a dopant material. Examples of the host material include fused aromatic ring derivatives, or heterocyclic compounds, etc. Specifically, examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but examples thereof are not limited thereto.

[0172] Examples of dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and examples thereof include pyrene, anthracene, and diindenopyrene, etc.; the styrylamine compound is a compound in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino are substituted or unsubstituted. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but are not limited thereto. In addition, examples of metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0173] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer, and the electron transport material is suitably a material that can well receive electrons from the negative electrode and transfer the electrons to the light-emitting layer, and has a high mobility for electrons. Specific examples thereof include: Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the related art. In particular, suitable examples of cathode materials are typical materials having a small work function followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

[0174] The electron injection layer is a layer that injects electrons from the electrode, and preferably a compound that has the ability to transport electrons, has an effect of injecting electrons from the negative electrode, 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 moving to the hole injection layer, and also has excellent thin film forming ability. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, The examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, and their derivatives, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like.

[0175] Examples of metal complex compounds include 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, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but are not limited thereto.

[0176] The hole blocking layer is a layer that blocks holes from reaching the negative electrode, and can generally be formed under the same conditions as those of the hole injection layer. Specific examples thereof include Oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but not limited thereto.

[0177] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a dual emission type according to the materials used.

[0178] According to an exemplary embodiment of the present specification, the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

[0180] Hereinafter, this specification will be described in detail with reference to the embodiments to specifically illustrate this specification. However, the embodiments according to this specification can be modified in various forms, and it is not interpreted that the scope of this specification is limited to the embodiments described in detail below. The embodiments of this specification are provided to more completely illustrate this specification to those of ordinary skill in the art.

[0181] <Example>

[0182] <Preparation Example 1>-Synthesis of Compound 1-1

[0183]

[0184] Under nitrogen atmosphere, in a 500ml round-bottom flask, compound A (10.0g, 20.58mmol) and 4-bromo-1,1'-biphenyl (5.25g, 22.63mmol) were completely dissolved in 180ml of xylene, and then sodium tert-butoxide (2.57g, 26.75mmol) was added thereto, bis(tri-tert-butylphosphine)palladium (0.11g, 0.21mmol) was put therein, and then the resulting mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the resulting mixture was filtered to remove salt, and then xylene was concentrated under reduced pressure, and the residue was recrystallized with 250ml of ethyl acetate to prepare compound 1-1 (11.56g, yield: 88%).

[0185] MS[M+H] + =639

[0186] <Preparation Example 2>-Synthesis of Compound 1-2

[0187]

[0188] Under nitrogen atmosphere, in a 500ml round-bottom flask, compound A (10.0g, 20.58mmol) and bromobenzene (3.53g, 22.63mmol) were completely dissolved in 120ml of xylene, then sodium tert-butoxide (2.57g, 26.75mmol) was added thereto, bis(tri-tert-butylphosphine)palladium (0.11g, 0.21mmol) was placed therein, and then the resulting mixture was heated and stirred for 1 hour. The temperature was lowered to room temperature, the resulting mixture was filtered to remove salt, then xylene was concentrated under reduced pressure, and the residue was recrystallized with 250ml of ethyl acetate to prepare compound 1-2 (9.16g, yield: 79%).

[0189] MS[M+H] + =563

[0190] <Preparation Example 3>-Synthesis of Compound 1-3

[0191]

[0192] Under nitrogen atmosphere, in a 500ml round-bottom flask, compound A (10.0g, 20.58mmol) and 2-bromo-9,9-diphenyl-9H-fluorene (6.16g, 22.63mmol) were completely dissolved in 140ml of xylene, and then sodium tert-butoxide (2.57g, 26.75mmol) was added thereto, bis(tri-tert-butylphosphine)palladium (0.11g, 0.21mmol) was put therein, and then the resulting mixture was heated and stirred for 2 hours. The temperature was lowered to room temperature, the resulting mixture was filtered to remove salt, and then xylene was concentrated under reduced pressure, and the residue was recrystallized with 200ml of ethyl acetate to prepare compound 1-3 (10.33g, yield: 74%).

[0193] MS[M+H] + =679

[0194] <Preparation Example 4>-Synthesis of Compound 1-4

[0195]

[0196] Under nitrogen atmosphere, in a 500ml round-bottom flask, compound A (10.0g, 20.58mmol) and 2-bromo-1,1'-biphenyl (5.25g, 22.63mmol) were completely dissolved in 180ml of xylene, and then sodium tert-butoxide (2.57g, 26.75mmol) was added thereto, bis(tri-tert-butylphosphine)palladium (0.11g, 0.21mmol) was put therein, and then the resulting mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the resulting mixture was filtered to remove salt, and then xylene was concentrated under reduced pressure, and the residue was recrystallized with 320ml of ethyl acetate to prepare compound 1-4 (10.41g, yield: 79%).

[0197] MS[M+H] + =639

[0198] <Preparation Example 5>-Synthesis of Compound 1-5

[0199]

[0200] Under nitrogen atmosphere, in a 500ml round-bottom flask, compound A (10.0g, 20.58mmol) and 2-bromonaphthalene (4.66g, 22.63mmol) were completely dissolved in 120ml of xylene, then sodium tert-butoxide (2.57g, 26.75mmol) was added thereto, bis(tri-tert-butylphosphine)palladium (0.11g, 0.21mmol) was placed therein, and then the resulting mixture was heated and stirred for 2 hours. The temperature was lowered to room temperature, the resulting mixture was filtered to remove salt, then xylene was concentrated under reduced pressure, and the residue was recrystallized with 200ml of ethyl acetate to prepare compound 1-5 (8.54g, yield: 68%).

[0201] MS[M+H] + =613

[0202] <Preparation Example 6>-Synthesis of Compound 1-6

[0203]

[0204] Under nitrogen atmosphere, in a 500ml round-bottom flask, compound A (10.0g, 20.58mmol) and 2-bromo-9,9-diphenyl-9H-fluorene (8.96g, 22.63mmol) were completely dissolved in 140ml of xylene, and then sodium tert-butoxide (2.57g, 26.75mmol) was added thereto, and bis(tri-tert-butylphosphine)palladium (0.11g, 0.21mmol) was placed therein, and then the resulting mixture was heated and stirred for 2 hours. The temperature was lowered to room temperature, the resulting mixture was filtered to remove salt, and then xylene was concentrated under reduced pressure, and the residue was recrystallized with 200ml of ethyl acetate to prepare compound 1-6 (13.76g, yield: 83%).

[0205] MS[M+H] + =803

[0206] <Preparation Example 7>-Synthesis of Compounds 1-7 to 1-12

[0207]

[0208] Compounds 1-7 to 1-12 were prepared by carrying out the same method as the method for preparing Compounds 1-1 to 1-6, except that the following Compound E was used instead of Compound A in Preparation Examples 1 to 6.

[0209] [Compound E]

[0210]

[0211] <Preparation Example 8>-Synthesis of Compound 1-13

[0212]

[0213] Under nitrogen atmosphere, in a 500ml round-bottom flask, compound B (10.0g, 18.66mmol) and 4-bromo-1,1'-biphenyl (4.76g, 20.52mmol) were completely dissolved in 180ml of xylene, and then sodium tert-butoxide (2.33g, 24.26mmol) was added thereto, bis(tri-tert-butylphosphine)palladium (0.09g, 0.19mmol) was put therein, and then the resulting mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the resulting mixture was filtered to remove salt, and then xylene was concentrated under reduced pressure, and the residue was recrystallized with 320ml of ethyl acetate to prepare compound 1-13 (9.46g, yield: 74%).

[0214] MS[M+H] + =689

[0215] <Preparation Example 9>-Synthesis of Compound 1-14

[0216]

[0217] Under nitrogen atmosphere, in a 500ml round-bottom flask, compound B (10.0g, 18.68mmol) and 2-bromo-9,9-dimethyl-9H-fluorene (5.58g, 20.52mmol) were completely dissolved in 160ml of xylene, and then sodium tert-butoxide (2.33g, 24.26mmol) was added thereto, bis(tri-tert-butylphosphine)palladium (0.09g, 0.19mmol) was put therein, and then the resulting mixture was heated and stirred for 2 hours. The temperature was lowered to room temperature, the resulting mixture was filtered to remove salt, and then xylene was concentrated under reduced pressure, and the residue was recrystallized with 200ml of ethyl acetate to prepare compound 1-14 (9.88g, yield: 70%).

[0218] MS[M+H] + =729

[0219] <Preparation Example 10>-Synthesis of Compound 1-15

[0220]

[0221] Under nitrogen atmosphere, in a 500ml round-bottom flask, compound B (10.0g, 18.66mmol) and bromobenzene (3.53g, 3.21mmol) were completely dissolved in 120ml of xylene, then sodium tert-butoxide (2.33g, 24.26mmol) was added thereto, bis(tri-tert-butylphosphine)palladium (0.09g, 0.19mmol) was placed therein, and then the resulting mixture was heated and stirred for 1 hour. The temperature was lowered to room temperature, the resulting mixture was filtered to remove salt, then xylene was concentrated under reduced pressure, and the residue was recrystallized with 250ml of ethyl acetate to prepare compound 1-15 (8.76g, yield: 75%).

[0222] MS[M+H] + =613

[0223] <Preparation Example 11>-Synthesis of Compound 1-16

[0224]

[0225] Under nitrogen atmosphere, in a 500ml round-bottom flask, compound B (10.0g, 18.68mmol) and 2-bromo-1,1'-biphenyl (5.25g, 22.63mmol) were completely dissolved in 180ml of xylene, and then sodium tert-butoxide (2.33g, 24.26mmol) was added thereto, bis(tri-tert-butylphosphine)palladium (0.09g, 0.19mmol) was put therein, and then the resulting mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the resulting mixture was filtered to remove salt, and then xylene was concentrated under reduced pressure, and the residue was recrystallized with 320ml of ethyl acetate to prepare compound 1-16 (9.54g, yield: 78%).

[0226] MS[M+H] + =689 <Preparation Example 12> - Synthesis of Compound 1-17

[0227]

[0228] Under nitrogen atmosphere, in a 500ml round-bottom flask, compound D (10.0g, 18.66mmol) and 4-bromo-1,1'-biphenyl (4.76g, 20.52mmol) were completely dissolved in 180ml of xylene, and then sodium tert-butoxide (2.33g, 24.26mmol) was added thereto, bis(tri-tert-butylphosphine)palladium (0.09g, 0.19mmol) was put therein, and then the resulting mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the resulting mixture was filtered to remove salt, and then xylene was concentrated under reduced pressure, and the residue was recrystallized with 320ml of ethyl acetate to prepare compound 1-17 (9.46g, yield: 74%).

[0229] MS[M+H] + =689

[0230] <Preparation Example 13>-Synthesis of Compound 1-18

[0231]

[0232] Under nitrogen atmosphere, in a 500ml round-bottom flask, compound D (10.0g, 18.68mmol) and 2-bromo-9,9-dimethyl-9H-fluorene (5.58g, 20.52mmol) were completely dissolved in 160ml of xylene, and then sodium tert-butoxide (2.33g, 24.26mmol) was added thereto, bis(tri-tert-butylphosphine)palladium (0.09g, 0.19mmol) was put therein, and then the resulting mixture was heated and stirred for 2 hours. The temperature was lowered to room temperature, the resulting mixture was filtered to remove salt, and then xylene was concentrated under reduced pressure, and the residue was recrystallized with 200ml of ethyl acetate to prepare compound 1-18 (8.91g, yield: 63%).

[0233] MS[M+H] + =729

[0234] <Preparation Example 14>-Synthesis of Compound 1-19

[0235]

[0236] Under nitrogen atmosphere, in a 500ml round-bottom flask, compound D (10.0g, 18.66mmol) and bromobenzene (3.53g, 3.21mmol) were completely dissolved in 120ml of xylene, then sodium tert-butoxide (2.33g, 24.26mmol) was added thereto, bis(tri-tert-butylphosphine)palladium (0.09g, 0.19mmol) was placed therein, and then the resulting mixture was heated and stirred for 1 hour. The temperature was lowered to room temperature, the resulting mixture was filtered to remove salt, then xylene was concentrated under reduced pressure, and the residue was recrystallized with 200ml of ethyl acetate to prepare compound 1-19 (7.89g, yield: 68%).

[0237] MS[M+H] + =613

[0238] <Preparation Example 15>-Synthesis of Compound 1-20

[0239]

[0240] Under nitrogen atmosphere, in a 500ml round-bottom flask, compound D (10.0g, 18.68mmol) and 2-bromo-1,1'-biphenyl (5.25g, 22.63mmol) were completely dissolved in 180ml of xylene, and then sodium tert-butoxide (2.33g, 24.26mmol) was added thereto, bis(tri-tert-butylphosphine)palladium (0.09g, 0.19mmol) was put therein, and then the resulting mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the resulting mixture was filtered to remove salt, and then xylene was concentrated under reduced pressure, and the residue was recrystallized with 320ml of ethyl acetate to prepare compound 1-20 (8.69g, yield: 71%).

[0241] MS[M+H] + =689

[0242] <Preparation Example 16>-Synthesis of Compounds 1-21 to 1-26

[0243]

[0244] Compounds 1-21 to 1-26 were prepared by carrying out the same method as the method for preparing Compounds 1-7 to 1-12, except that the following Compound F was used instead of Compound E in Preparation Example 7.

[0245] [Compound F]

[0246]

[0247] <Preparation Example 17>-Synthesis of Compounds 1-27 to 1-32

[0248]

[0249] Compounds 1-27 to 1-32 were prepared by carrying out the same method as the method for preparing Compounds 1-7 to 1-12, except that the following Compound H was used instead of Compound E in Preparation Example 7.

[0250] [Compound H]

[0251]

[0252] <Experimental Example 1>

[0253] <Experimental Example 1-1>

[0254] A thin coating having a thickness of The glass substrate of indium tin oxide (ITO) is put into the distilled water dissolved with detergent therein, and carries out ultrasonic cleaning.In this case, the product manufactured by Fischer Co. is used as detergent, and the distilled water filtered twice by the filter manufactured by Millipore Co. is used as distilled water.After ITO was washed for 30 minutes, distilled water was used to repeat ultrasonic cleaning twice for 10 minutes.After the washing with distilled water is completed, isopropyl alcohol, acetone and methanol solvent are used to carry out ultrasonic cleaning, and dry, and then substrate is transferred to plasma cleaning machine.In addition, oxygen plasma is used to clean substrate for 5 minutes, and then it is transferred to vacuum evaporator.

[0255] Hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited on the thus prepared transparent ITO electrode until A thickness of 10000 is achieved, thereby forming a hole injection layer.

[0256] [HAT]

[0257]

[0258] The following compound 4-4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was used as a material for transporting holes. The hole transport layer is formed by vacuum deposition on the hole injection layer.

[0259] [NPB]

[0260]

[0261] Subsequently, the following compound 1-1 was vacuum deposited on the hole transport layer to The film thickness is , thereby forming an electron blocking layer.

[0262] [Compound 1-1]

[0263]

[0264] Subsequently, the following BH and BD were vacuum deposited on the electron blocking layer at a weight ratio of 25:1. The film thickness is , thereby forming a light-emitting layer.

[0265]

[0266] Compound ET1 and compound LiQ (lithium quinoline) are vacuum deposited on the light-emitting layer at a weight ratio of 1:1, thereby forming a layer with a thickness of The electron injection and transport layer is formed. Lithium fluoride (LiF) and aluminum are sequentially deposited on the electron injection and transport layer to and , thereby forming a negative electrode.

[0267] During the above process, the deposition rate of the organic material is kept at to The deposition rates of lithium fluoride and aluminum in the negative electrode were kept at and The vacuum degree during deposition was maintained at 2×10 -7 Up to 5×10 -6 The support is used to manufacture an organic light-emitting device.

[0268] <Experimental Example 1-2>

[0269] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 1-2 was used instead of Compound 1-1 in Experimental Example 1-1.

[0270] <Experimental Examples 1-3>

[0271] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 1-3 was used instead of Compound 1-1 in Experimental Example 1-1.

[0272] <Experimental Examples 1-4>

[0273] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 1-4 was used instead of Compound 1-1 in Experimental Example 1-1.

[0274] <Experimental Examples 1-5>

[0275] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 1-5 was used instead of Compound 1-1 in Experimental Example 1-1.

[0276] <Experimental Examples 1-6>

[0277] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 1-6 was used instead of Compound 1-1 in Experimental Example 1-1.

[0278] <Experimental Example 1-7>

[0279] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 1-11 was used instead of Compound 1-1 in Experimental Example 1-1.

[0280] <Experimental Example 1-8>

[0281] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 1-12 was used instead of Compound 1-1 in Experimental Example 1-1.

[0282] <Experimental Example 1-9>

[0283] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 1-14 was used instead of Compound 1-1 in Experimental Example 1-1.

[0284] <Experimental Example 1-10>

[0285] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 1-15 was used instead of Compound 1-1 in Experimental Example 1-1.

[0286] <Experimental Example 1-11>

[0287] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 1-19 was used instead of Compound 1-1 in Experimental Example 1-1.

[0288] <Experimental Example 1-12>

[0289] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 1-20 was used instead of Compound 1-1 in Experimental Example 1-1.

[0290] <Experimental Example 1-13>

[0291] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 1-21 was used instead of Compound 1-1 in Experimental Example 1-1.

[0292] <Experimental Example 1-14>

[0293] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 1-24 was used instead of Compound 1-1 in Experimental Example 1-1.

[0294] <Experimental Example 1-15>

[0295] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 1-28 was used instead of Compound 1-1 in Experimental Example 1-1.

[0296] <Experimental Example 1-16>

[0297] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 1-29 was used instead of Compound 1-1 in Experimental Example 1-1.

[0298] <Comparative Example 1-1>

[0299] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the following EB 1 was used instead of Compound 1-1 in Experimental Example 1-1.

[0300] [EB 1]

[0301]

[0302] <Comparative Example 1-2>

[0303] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the following EB 2 was used instead of Compound 1-1 in Experimental Example 1-1.

[0304] [EB 2]

[0305]

[0306] <Comparative Examples 1-3>

[0307] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the following EB 3 was used instead of Compound 1-1 in Experimental Example 1-1.

[0308] [EB 3]

[0309]

[0310] <Comparative Examples 1-4>

[0311] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the following EB 4 was used instead of Compound 1-1 in Experimental Example 1-1.

[0312] [EB 4]

[0313]

[0314] <Comparative Examples 1-5>

[0315] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the following EB 5 was used instead of Compound 1-1 in Experimental Example 1-1.

[0316] [EB 5]

[0317]

[0318] When current was applied to the organic light emitting devices manufactured in Experimental Examples 1-1 to 1-16 and Comparative Examples 1-1 to 1-5, the results of the following Table 1 were obtained.

[0319] [Table 1]

[0320]

[0321] As observed in Table 1, it can be seen that when the compounds in Experimental Examples 1-1 to 1-16 are used as an electron blocking layer in an organic light emitting device, the compounds exhibit lower voltage and higher efficiency characteristics than the materials in Comparative Examples 1-1 to 1-5.

[0322] Specifically, when Experimental Examples 1-1 to 1-6 and Comparative Examples 1-1 and 1-4 were compared with each other, it was determined that the case where carbazole was directly substituted at the ortho position of the benzene ring had the effect of reducing the driving voltage by 10% to 15% and increasing the light efficiency by 20%, compared with the case where carbazole was substituted at the meta and para positions of the benzene ring.

[0323] In addition, when Experimental Examples 1-7 and 1-8 and Comparative Examples 1-2 and 1-3 are compared with each other, the case where carbazole is directly substituted at the ortho position shows lower driving voltage and higher efficiency even when there is a linking group (linker) between the benzene ring and the carbazole structure, compared with the case where carbazole is substituted at the meta and para positions. It can be seen that such a trend is shown even in Experimental Examples 1-9 to 1-12 and Comparative Example 1-5 in which the benzene ring is substituted with fused benzocarbazole.

[0324] Therefore, it can be confirmed that the compound derivative according to the chemical formula of the present specification has excellent electron blocking ability and thus exhibits low voltage and high efficiency characteristics and can be applied to an organic light emitting device.

[0325] <Experimental Example 2>

[0326] <Experimental Example 2-1>

[0327] The experiment was performed in the same manner as in Experimental Example 1-1, except that the following compound TCTA was used as the electron blocking layer, and Compound 1-1 was used instead of NPB as the hole transport layer.

[0328] [TCTA]

[0329]

[0330] <Experimental Example 2-2>

[0331] The experiment was performed in the same manner as in Experimental Example 1-1, except that Compound TCTA was used as the electron blocking layer, and Compound 1-2 was used instead of NPB as the hole transport layer.

[0332] <Experimental Example 2-3>

[0333] The experiment was performed in the same manner as in Experimental Example 1-1, except that Compound TCTA was used as the electron blocking layer, and Compound 1-3 was used instead of NPB as the hole transport layer.

[0334] <Experimental Example 2-4>

[0335] The experiment was performed in the same manner as in Experimental Example 1-1, except that Compound TCTA was used as the electron blocking layer, and Compound 1-4 was used instead of NPB as the hole transport layer.

[0336] <Experimental Example 2-5>

[0337] The experiment was performed in the same manner as in Experimental Example 1-1, except that Compound TCTA was used as the electron blocking layer, and Compound 1-5 was used instead of NPB as the hole transport layer.

[0338] <Experimental Example 2-6>

[0339] The experiment was performed in the same manner as in Experimental Example 1-1, except that Compound TCTA was used as the electron blocking layer, and Compound 1-6 was used instead of NPB as the hole transport layer.

[0340] <Experimental Example 2-7>

[0341] The experiment was performed in the same manner as in Experimental Example 1-1, except that Compound TCTA was used as the electron blocking layer, and Compound 1-9 was used instead of NPB as the hole transport layer.

[0342] <Experimental Example 2-8>

[0343] The experiment was performed in the same manner as in Experimental Example 1-1, except that Compound TCTA was used as the electron blocking layer, and Compound 1-10 was used instead of NPB as the hole transport layer.

[0344] <Experimental Example 2-9>

[0345] The experiment was performed in the same manner as in Experimental Example 1-1, except that Compound TCTA was used as the electron blocking layer, and Compound 1-13 was used instead of NPB as the hole transport layer.

[0346] <Experimental Example 2-10>

[0347] The experiment was performed in the same manner as in Experimental Example 1-1, except that Compound TCTA was used as the electron blocking layer, and Compound 1-16 was used instead of NPB as the hole transport layer.

[0348] <Experimental Example 2-11>

[0349] The experiment was performed in the same manner as in Experimental Example 1-1, except that Compound TCTA was used as the electron blocking layer, and Compound 1-17 was used instead of NPB as the hole transport layer.

[0350] <Experimental Example 2-12>

[0351] The experiment was performed in the same manner as in Experimental Example 1-1, except that Compound TCTA was used as the electron blocking layer, and Compound 1-18 was used instead of NPB as the hole transport layer.

[0352] <Experimental Example 2-13>

[0353] The experiment was performed in the same manner as in Experimental Example 1-1, except that the compound TCTA was used as the electron blocking layer, and the compound 1-22 was used instead of NPB as the hole transport layer.

[0354] <Experimental Example 2-14>

[0355] The experiment was performed in the same manner as in Experimental Example 1-1, except that the compound TCTA was used as the electron blocking layer, and the compound 1-23 was used instead of NPB as the hole transport layer.

[0356] <Experimental Example 2-15>

[0357] The experiment was performed in the same manner as in Experimental Example 1-1, except that Compound TCTA was used as the electron blocking layer, and Compound 1-31 was used instead of NPB as the hole transport layer.

[0358] <Experimental Example 2-16>

[0359] The experiment was performed in the same manner as in Experimental Example 1-1, except that the compound TCTA was used as the electron blocking layer, and the compound 1-32 was used instead of NPB as the hole transport layer.

[0360] <Comparative Example 2-1>

[0361] The experiment was performed in the same manner as in Experimental Example 1-1, except that TCTA was used as the electron blocking layer, and the following HT 1 was used as the hole transport layer.

[0362] [HT 1]

[0363]

[0364] <Comparative Example 2-2>

[0365] The experiment was performed in the same manner as in Experimental Example 1-1, except that TCTA was used as the electron blocking layer, and the following HT 2 was used as the hole transport layer.

[0366] [HT 2]

[0367]

[0368] <Comparative Example 2-3>

[0369] The experiment was performed in the same manner as in Experimental Example 1-1, except that TCTA was used as the electron blocking layer, and the following HT 3 was used as the hole transport layer.

[0370] [HT 3]

[0371]

[0372] <Comparative Example 2-4>

[0373] The experiment was performed in the same manner as in Experimental Example 1-1, except that TCTA was used as the electron blocking layer, and the following HT 4 was used as the hole transport layer.

[0374] [HT 4]

[0375]

[0376] When current was applied to the organic light emitting devices manufactured in Experimental Examples 2-1 to 2-16 and Comparative Examples 2-1 to 2-4, the results of the following Table 2 were obtained.

[0377] [Table 2]

[0378]

[0379] As observed in Table 2, it can be seen that when the compounds in Experimental Examples 2-1 to 2-16 were used as a hole transport layer in an organic light-emitting device, the compounds exhibited lower voltage and higher efficiency characteristics than those in Comparative Examples 2-1 to 2-4.

[0380] Specifically, when Experimental Examples 2-1 to 2-6 and Comparative Examples 2-1 and 2-4 were compared with each other, it was determined that the case where carbazole was directly substituted at the ortho position of the benzene ring had the effect of reducing the driving voltage by 8% to 10% and increasing the light efficiency by 20% to 25%, compared with the case where carbazole was substituted at the meta and para positions of the benzene ring.

[0381] In addition, when Experimental Examples 2-7 and 2-8 and Comparative Example 2-4 are compared with each other, the case where carbazole is directly substituted at the ortho position shows lower driving voltage and higher efficiency even when there is a linking group (linker) between the benzene ring and the carbazole structure, compared with those when carbazole is substituted at the meta position. It can be seen that such a trend is shown even in Experimental Examples 2-9 to 2-12 and Comparative Examples 2-2 and 2-3 in which the benzene ring is substituted by fused benzocarbazole.

[0382] Therefore, it can be confirmed that the compound derivative according to the chemical formula of the present specification also has excellent hole transporting ability and thus exhibits low voltage and high efficiency characteristics and can be applied to organic light emitting devices.

[0383] Although the preferred exemplary embodiments of the present invention (electron blocking layer and hole transport layer) are described above, the present invention is not limited thereto, and various modifications can be made and performed within the scope of the claims and detailed description of the present invention, and these modifications also fall within the scope of the present invention.

[0384] The following content corresponds to the original claims in the parent application and is now incorporated herein as part of the specification:

[0385] 1. A compound represented by the following chemical formula 1:

[0386] [Chemical formula 1]

[0387]

[0388] In Chemical Formula 1,

[0389] L1 to L3 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted arylene group,

[0390] Ar1 and Ar2 are the same as or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group,

[0391] R1 to R8 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are optionally combined with adjacent groups to form a substituted or unsubstituted ring,

[0392] R9 and R 10 are the same as or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

[0393] p and q are integers from 1 to 4,

[0394] When p is 2 or more, a plurality of R9 are the same as or different from each other, and

[0395] When q is 2 or greater, multiple R 10 The same as or different from each other.

[0396] 2. A compound according to claim 1, wherein L1 to L3 are the same as or different from each other and are each independently a direct bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthracenylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted triphenylene, or a substituted or unsubstituted fluorenylene.

[0397] 3. A compound according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other and are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenyl, or substituted or unsubstituted fluorenyl.

[0398] 4. The compound according to item 1, wherein R1 and R2, R2 and R3, or R3 and R4 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

[0399] 5. The compound according to item 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 4:

[0400] [Chemical formula 2]

[0401]

[0402] [Chemical formula 3]

[0403]

[0404] [Chemical formula 4]

[0405]

[0406] In Chemical Formulas 2 to 4,

[0407] L1 to L3, Ar1, Ar2, R1 to R 10 , p and q are the same as those defined in Chemical Formula 1,

[0408] R' is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

[0409] r is an integer from 1 to 4, and

[0410] When r is 2 or more, a plurality of R's are the same as or different from each other.

[0411] 6. The compound according to item 1, wherein R9 and R 10 For hydrogen.

[0412] 7. The compound according to item 1, wherein the compound represented by Chemical Formula 1 is any one selected from the following compounds:

[0413]

[0414]

[0415]

[0416]

[0417]

[0418] 8. An organic electronic device comprising:

[0419] a first electrode;

[0420] a second electrode disposed to face the first electrode; and

[0421] one or more organic material layers disposed between the first electrode and the second electrode,

[0422] wherein one or more of the organic material layers comprises the compound according to any one of items 1 to 7.

[0423] 9. The organic electronic device according to item 8, wherein the organic material layer comprises a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer contains the compound.

[0424] 10. The organic electronic device according to item 8, wherein the organic material layer includes an electron blocking layer, and the electron blocking layer contains the compound.

[0425] 11. The organic electronic device according to item 8, further comprising:

[0426] One or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer and an electron blocking layer.

[0427] 12. The organic electronic device according to item 8, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.

[0428] 13. The organic electronic device according to item 8, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer comprises a compound represented by the following Chemical Formula 1-A:

[0429] [Chemical Formula 1-A]

[0430]

[0431] In Chemical Formula 1-A,

[0432] n1 is an integer of 1 or greater,

[0433] Ar7 is a substituted or unsubstituted monovalent or higher valent benzofluorenyl group, a substituted or unsubstituted monovalent or higher valent fluoranthene group, a substituted or unsubstituted monovalent or higher valent pyrenyl group, or a substituted or unsubstituted monovalent or higher valent base,

[0434] L4 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0435] Ar8 and Ar9 are the same as or different from each other, and are each independently substituted or unsubstituted aryl, substituted or unsubstituted silyl, substituted or unsubstituted germanyl, substituted or unsubstituted alkyl, substituted or unsubstituted arylalkyl, or substituted or unsubstituted heteroaryl, or are optionally combined with each other to form a substituted or unsubstituted ring, and

[0436] When n1 is 2 or more, two or more structures in the brackets are the same as or different from each other.

[0437] 14. An organic electronic device according to item 13, wherein L4 is a direct bond, Ar7 is a divalent pyrene group, Ar8 and Ar9 are the same as or different from each other and are each independently an aryl group which is unsubstituted or substituted with a germanium group substituted with an alkyl group, and n1 is 2.

[0438] 15. The organic electronic device according to item 8, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer comprises a compound represented by the following Chemical Formula 2-A:

[0439] [Chemical Formula 2-A]

[0440]

[0441] In Chemical Formula 2-A,

[0442] G 11 is 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1-naphthyl, 2-naphthyl, 9-naphthyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, or the following chemical formula

[0443] G 12 is phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1-naphthyl, 2-naphthyl, 9-naphthyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl 1-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1-anthracenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, or 3-fluoranthenyl,

[0444] G 13 and G 14 are the same as or different from each other and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0445] g 12 is an integer from 1 to 5,

[0446] g 13 and g 14 are each an integer from 1 to 4, and

[0447] When 12 tog 14 When each is 2 or more, two or more structures in the brackets are the same as or different from each other.

[0448] 16. The organic electronic device according to item 15, wherein G 11 is 1-naphthyl, G 12 It is 2-naphthyl.

[0449] 17. The organic electronic device according to item 13, wherein the light-emitting layer comprises a compound represented by the following Chemical Formula 2-A:

[0450] [Chemical Formula 2-A]

[0451]

[0452] In Chemical Formula 2-A,

[0453] G 11 is phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-naphthyl, 2-naphthyl, 9-naphthyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, or the following chemical formula

[0454] G 12 is phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1-naphthyl, 2-naphthyl, 9-naphthyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl 1-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1-anthracenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, or 3-fluoranthenyl,

[0455] G 13 and G 14 are the same as or different from each other and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0456] g 12 is an integer from 1 to 5,

[0457] g 13 and g 14 are each an integer from 1 to 4, and

[0458] When 12 tog 14 When each is 2 or more, two or more structures in the brackets are the same as or different from each other.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] In Chemical Formula 1, L1 to L2 are the same as or different from each other, and are each independently a direct bond, an unsubstituted or deuterium-substituted phenylene group, or an unsubstituted or deuterium-substituted biphenylene group, L3 is a direct key; Ar1 and Ar2 are the same as or different from each other and are each independently an unsubstituted or deuterium-substituted phenyl group, an unsubstituted or deuterium-substituted biphenyl group, an unsubstituted or deuterium-substituted terphenyl group, an unsubstituted or deuterium-substituted naphthyl group, an unsubstituted or deuterium-substituted anthracenyl group, an unsubstituted or deuterium-substituted phenanthrenyl group, an unsubstituted or deuterium-substituted triphenylene group, or an unsubstituted or deuterium-substituted fluorenyl group, R1 to R 10 are the same as or different from each other and are each independently hydrogen or deuterium, p and q are integers from 1 to 4, When p is 2 or more, a plurality of R9 are the same as or different from each other, When q is 2 or greater, multiple R 10 The same as or different from each other.

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

3. An organic electronic device comprising: a first electrode; a second electrode disposed facing the first electrode; as well as one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound according to any one of claims 1 to 2. 4 . The organic electronic device according to claim 3 , wherein the organic material layer comprises a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound. 5 . The organic electronic device according to claim 3 , wherein the organic material layer comprises an electron blocking layer, and the electron blocking layer contains the compound.

6. The organic electronic device according to claim 3, further comprising: One or two or more layers selected from a hole injection layer, a hole transport layer and an electron blocking layer.

7. The organic electronic device according to claim 3, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.

8. The organic electronic device according to claim 3, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer comprises a compound represented by the following Chemical Formula 1-A: [Chemical Formula 1-A] In Chemical Formula 1-A, n1 is an integer of 1 or greater, Ar7 is a substituted or unsubstituted monovalent or higher valent benzofluorenyl group, a substituted or unsubstituted monovalent or higher valent fluoranthene group, a substituted or unsubstituted monovalent or higher valent pyrenyl group, or a substituted or unsubstituted monovalent or higher valent base, L4 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, Ar8 and Ar9 are the same as or different from each other, and are each independently substituted or unsubstituted aryl, substituted or unsubstituted silyl, substituted or unsubstituted germanyl, substituted or unsubstituted alkyl, substituted or unsubstituted arylalkyl, or substituted or unsubstituted heteroaryl, or are optionally combined with each other to form a substituted or unsubstituted ring, and When n1 is 2 or more, two or more structures in the brackets are the same as or different from each other.

9. The organic electronic device according to claim 8, wherein L4 is a direct bond, Ar7 is a divalent pyrene group, Ar8 and Ar9 are the same as or different from each other and are each independently an aryl group which is unsubstituted or substituted with a germanium group substituted with an alkyl group, and n1 is 2.

10. The organic electronic device according to claim 3, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer comprises a compound represented by the following Chemical Formula 2-A: [Chemical Formula 2-A] In Chemical Formula 2-A, G 11 is 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1-naphthyl, 2-naphthyl, 9-naphthyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, or the following chemical formula G 12 is phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1-naphthyl, 2-naphthyl, 9-naphthyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl 1-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1-anthracenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, or 3-fluoranthenyl, G 13 and G 14 are the same as or different from each other and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, g 12 is an integer from 1 to 5, g 13 and g 14 are each an integer from 1 to 4, and When 12 tog 14 When each is 2 or more, two or more structures in the brackets are the same as or different from each other.

11. The organic electronic device according to claim 10, wherein G 11 is 1-naphthyl, G 12 It is 2-naphthyl.

12. The organic electronic device according to claim 8, wherein the light emitting layer comprises a compound represented by the following Chemical Formula 2-A: [Chemical Formula 2-A] In Chemical Formula 2-A, G 11 is phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-naphthyl, 2-naphthyl, 9-naphthyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, or the following chemical formula G 12 is phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, 1-naphthyl, 2-naphthyl, 9-naphthyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl 1-(2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1-anthracenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, or 3-fluoranthenyl, G 13 and G 14 are the same as or different from each other and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, g 12 is an integer from 1 to 5, g 13 and g 14 are each an integer from 1 to 4, and When 12 tog 14 When each is 2 or more, two or more structures in the brackets are the same as or different from each other.

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