Novel Boron Compound and Organic Light-Emitting Element Comprising the Same

Abstract

The present invention relates to a boron compound that can be used in an organic light-emitting device and an organic light-emitting device including the boron compound. More specifically, the present invention relates to a boron compound represented by [Chemical Formula A] and an organic light-emitting device including the boron compound, and the [Chemical Formula A] is the same as that described in the detailed description of the invention.

Description

Technical Field

[0001] The present invention relates to a novel boron compound that can be used in an organic light-emitting device. More specifically, the present invention relates to a novel boron compound that can be used as a dopant material in a light-emitting layer in an organic light-emitting device and can thereby achieve device characteristics such as high luminous efficiency and low-voltage driving, and an organic light-emitting device including the boron compound. Background Art

[0002] An organic light-emitting device (OLED: organic light emitting diode) is a display that utilizes the self-luminescence phenomenon. It not only has a wide viewing angle but also has advantages such as being able to be made thinner, shorter, and having a fast response speed compared to a liquid crystal display. Therefore, it is expected to be applied as a full-color display or lighting.

[0003] Generally, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using an organic substance. An organic light-emitting device that utilizes the organic light-emitting phenomenon generally has a structure including an anode, a cathode, and an organic layer therebetween. Here, in most cases, in order to improve the efficiency and stability of the organic light-emitting device, the organic layer is configured as a multilayer structure composed of different substances. For example, it can be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In this structure of the organic light-emitting device, when 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 light is emitted when the excitons return to the ground state again. It is known that such an organic light-emitting device has characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and fast responsiveness.

[0004] The materials used as the organic layer in an organic light-emitting device can be classified into light-emitting materials and charge transport materials according to their functions. For example, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc. An electron blocking layer or a hole blocking layer can be added as needed.

[0005] The light-emitting materials can be classified into a polymer type and a low-molecular type according to their molecular weights, and can be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to their light-emitting mechanisms.

[0006] In addition, when only one substance is used as a light-emitting material, there are problems such as the maximum emission wavelength shifting to the long-wavelength side due to intermolecular interactions, a decrease in color purity, or a decrease in the efficiency of the device due to the luminescence decay effect. Therefore, in order to improve color purity and increase the luminescence efficiency through energy transfer, a host-dopant system can be used as the light-emitting material.

[0007] The principle is as follows: If a small amount of a dopant with a smaller band gap than that of the host forming the light-emitting layer is mixed in the light-emitting layer, excitons generated from the light-emitting layer are transferred to the dopant to emit light with high efficiency. At this time, the wavelength of the host shifts to the wavelength band of the dopant, so light with a desired wavelength can be obtained according to the type of dopant used.

[0008] Recently, research has been conducted on using boron compounds as dopant compounds in such light-emitting layers. As related prior art, Korean Patent Publication No. 10-2016-0119683 (October 14, 2016) discloses polycyclic aromatic compounds that connect multiple aromatic rings using atoms such as boron atoms and oxygen atoms, and organic light-emitting devices including the same. International Patent Publication No. 2017-188111 (November 2, 2017) describes a compound having a structure in which multiple fused aromatic rings are connected by boron atoms and nitrogen, and an organic light-emitting device using the compound as a dopant in the light-emitting layer and using an anthracene derivative as the host.

[0009] However, even though various forms of compounds used in the light-emitting layers of organic light-emitting devices including the above prior art have been fabricated, there is still a continuous need to develop new compounds that can be applied to organic light-emitting devices and have excellent device characteristics such as low-voltage driving, stability, and high efficiency, as well as organic light-emitting devices including such compounds. Summary of the Invention

[0010] Technical Problem

[0011] Therefore, the first technical problem that the present invention aims to solve is to provide a boron compound having a novel structure that can be used as a dopant substance in the light-emitting layer of an organic light-emitting device.

[0012] In addition, the second technical problem that the present invention aims to solve is to provide an organic light-emitting device (OLED: organic light emitting diode) having excellent device characteristics such as high luminescence efficiency and low-voltage driving by applying the boron compound to the dopant substance in the organic light-emitting device.

[0013] Technical Solution

[0014] In order to achieve the above technical problem, the present invention provides a boron compound represented by the following [Chemical Formula A].

[0015] [Chemical Formula A]

[0016]

[0017] In the said [Chemical Formula A],

[0018] said Y is selected from CR 12 R 13 , NR 14 , O, and S, any one of them,

[0019] said Z is selected from CR 15 R 16 , NR 17 , O, and S, any one of them,

[0020] said X is CR 18 or a nitrogen atom (N),

[0021] said substituents R1 to R 17 are the same as or different from each other, and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, nitro, cyano, halogen, and -N(R 19 )(R 20 ), any one of them,

[0022] said substituents R 18 to R 20 are the same as or different from each other, and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and said substituents R 19 and R 20 may be connected to each other to additionally form a monocyclic or polycyclic alicyclic or aromatic ring,

[0023] substituents R 12 and R 13 may be connected to each other to additionally form a monocyclic or polycyclic alicyclic or aromatic ring,

[0024] The substituent R 15 and R 16 may be connected to each other to additionally form a monocyclic or polycyclic alicyclic or aromatic ring,

[0025] The substituent R 12 to R 14 may be respectively connected to the substituent R1 or R 11 and connected to each other to additionally form a monocyclic or polycyclic alicyclic or aromatic ring,

[0026] The substituent R 15 to R 17 may be respectively connected to the substituent R8 or R9 and connected to each other to additionally form a monocyclic or polycyclic alicyclic or aromatic ring,

[0027] In the [Chemical Formula A], the "substituted" in the "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, haloalkyl group having 1 to 24 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 2 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, diarylamino group having 12 to 24 carbon atoms, diheteroarylamino group having 2 to 24 carbon atoms, aryl(heteroaryl)amino group having 7 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms, arylsilyl group having 6 to 24 carbon atoms, aryloxy group having 6 to 24 carbon atoms, and arylsulfinyl group having 6 to 24 carbon atoms.

[0028] Advantages of the Invention

[0029] When the novel boron compound according to the present invention is used as a dopant material in an organic light-emitting device, there is provided an organic light-emitting device that can achieve low-voltage driving and exhibit improved efficiency as compared with an organic light-emitting device according to the prior art. Brief Description of the Drawings

[0030] Figure 1 is a schematic diagram of an organic light-emitting device according to a specific example of the present invention. Detailed Description of the Invention

[0031] Hereinafter, the present invention will be described in more detail. In the respective drawings of the present invention, the size or dimensions of the structure are shown enlarged or reduced compared to the actual ones for the clarity of the present invention, and in order to highlight the characteristic configurations, well-known configurations are omitted and shown, and thus are not limited to the drawings.

[0032] Moreover, the sizes and thicknesses of the respective configurations shown in the drawings are arbitrarily shown for ease of explanation, and thus the present invention is not necessarily limited to the illustrated content, and in the drawings, the thicknesses are shown enlarged in order to clearly represent multiple layers and regions. Also, in the drawings, the thicknesses of some layers and regions are exaggerated for ease of explanation. When it is mentioned that a part such as a layer, film, region, plate, etc. is “on” another part, it includes not only the case where it is “immediately above” the other part, but also the case where there is another part in between.

[0033] Moreover, throughout the specification, when it is mentioned that a certain part “comprises” a certain constituent element, in the absence of special contrary description, it means that other constituent elements are not excluded and other constituent elements can also be included. Also, throughout the specification, “on...” means above or below the object part, and does not necessarily mean on the upper side based on the direction of gravity.

[0034] The present invention provides a boron compound represented by the following [Chemical Formula A].

[0035] [Chemical Formula A]

[0036]

[0037] In the said [Chemical Formula A],

[0038] the said Y is selected from CR 12 R 13 , NR 14 , O, and S, any one of them,

[0039] the said Z is selected from CR 15 R 16 , NR 17 , O, and S, any one of them,

[0040] the said X is CR 18 or a nitrogen atom (N),

[0041] the said substituents R1 to R 17Each is the same as or different from one another, and is independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, nitro, cyano, halogen, and -N(R 19 )(R 20 ), and is any one of them,

[0042] The substituents R 18 to R 20 are the same as or different from one another, and are independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms. The substituents R 19 and R 20 may be connected to each other to additionally form a monocyclic or polycyclic alicyclic or aromatic ring,

[0043] The substituents R 12 and R 13 may be connected to each other to additionally form a monocyclic or polycyclic alicyclic or aromatic ring,

[0044] The substituents R 15 and R 16 may be connected to each other to additionally form a monocyclic or polycyclic alicyclic or aromatic ring,

[0045] The substituents R 12 to R 14 may be respectively connected to the substituent R1 or R 11 to each other to additionally form a monocyclic or polycyclic alicyclic or aromatic ring,

[0046] And, the substituents R 15 to R 17 may be respectively connected to the substituent R8 or R9 to each other to additionally form a monocyclic or polycyclic alicyclic or aromatic ring,

[0047] Among them, in the [Chemical Formula A], the "substituted" in the "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of: deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, haloalkyl group having 1 to 24 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 2 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, diarylamino group having 12 to 24 carbon atoms, diheteroarylamino group having 2 to 24 carbon atoms, aryl(heteroaryl)amino group having 7 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms, arylsilyl group having 6 to 24 carbon atoms, aryloxy group having 6 to 24 carbon atoms, and arylsulfinyl group having 6 to 24 carbon atoms.

[0048] Moreover, when considering the ranges of the alkyl group or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms", "substituted or unsubstituted aryl group having 6 to 50 carbon atoms", etc. in the present invention, the ranges of the number of carbon atoms of the alkyl group having 1 to 30 carbon atoms and the aryl group having 6 to 50 carbon atoms respectively represent: the total number of carbon atoms constituting the alkyl part or aryl part when regarded as unsubstituted without considering the part substituted by the substituent. For example, a phenyl group substituted by a butyl group at the para position should be regarded as an aryl group having 6 carbon atoms substituted by a butyl group having 4 carbon atoms.

[0049] The aryl group as a substituent used in the compound of the present invention is an organic radical derived from an aromatic hydrocarbon by removing one hydrogen atom. When there are substituents in the aryl group, adjacent substituents can be fused to each other to additionally form a ring.

[0050] Specific examples of the aryl group may include phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group, pyrenyl group, indenyl group, fluorenyl group, tetrahydronaphthyl group, perylenyl group, Aromatic groups such as a base, a tetraphenyl group, and a fluoranthenyl group, and one or more hydrogen atoms in the aryl group may be replaced by a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH2, -NH(R), -N(R')(R”), where R' and R” are each independently an alkyl group having 1 to 10 carbon atoms, and in this case, it is called an “alkylamino”), an amidino group, a hydrazino group, a hydrazono group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or a heteroarylalkyl group having 2 to 24 carbon atoms.

[0051] The heteroaryl as a substituent used in the compound of the present invention represents a cyclic aromatic system having 2 to 24 carbon atoms including 1, 2, or 3 heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te, and the remaining ring-forming atoms are carbon atoms, and the ring may be fused to form a ring. In addition, one or more hydrogen atoms in the heteroaryl group may be replaced by the same substituents as in the case of the aryl group.

[0052] Moreover, in the present invention, the aromatic heterocycle means a case where one or more carbons in the aromatic carbon of the aromatic hydrocarbon ring are replaced by heteroatoms, and preferably, 1 to 3 aromatic carbons in the aromatic hydrocarbon may be replaced by one or more heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te.

[0053] The alkyl group as a substituent used in the present invention is a substituent obtained by removing one hydrogen from an alkane, and includes a straight-chain or branched-chain structure. Specific examples thereof may include a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a hexyl group, etc. One or more hydrogen atoms in the alkyl group may be replaced by the same substituents as in the case of the aryl group.

[0054] The “ring” in the cycloalkyl group as a substituent used in the compound of the present invention represents a substituent that can form a monocyclic or polycyclic structure of a saturated hydrocarbon in the alkyl group. For example, specific examples of the cycloalkyl group may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a methylcyclopentyl group, a methylcyclohexyl group, an ethylcyclopentyl group, an ethylcyclohexyl group, an adamantyl group, a dicyclopentadienyl group, a decahydronaphthyl group, a norbornyl group, a borneol group, an isoborneol group, etc. One or more hydrogen atoms in the cycloalkyl group may be replaced by the same substituents as in the case of the aryl group.

[0055] The alkoxy group of the substituent used in the compounds of the present invention is a substituent in which an oxygen atom is bonded to the end of an alkyl or cycloalkyl group. Specific examples thereof may include methoxy, ethoxy, propoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, hexyloxy, cyclobutoxy, cyclopentyloxy, adamantyloxy, dicyclopentyloxy, bornyloxy, isobornyloxy, etc. One or more hydrogen atoms in the alkoxy group may be substituted with the same substituents as in the case of the aryl group.

[0056] Specific examples of the arylalkyl group of the substituent used in the compounds of the present invention may include benzyl, phenethyl, phenylpropyl, naphthylmethyl, naphthylethyl, etc. One or more hydrogen atoms in the arylalkyl group may be substituted with the same substituents as in the case of the aryl group.

[0057] Specific examples of the silyl group of the substituent used in the compounds of the present invention may include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc. One or more hydrogen atoms in the silyl group may be substituted with the same substituents as in the case of the aryl group.

[0058] In addition, alkenyl in the present invention means an alkyl substituent including a carbon-carbon double bond composed of two carbon atoms, and alkynyl means an alkyl substituent including a carbon-carbon triple bond composed of two carbon atoms.

[0059] In addition, the alkylene group used in the present invention is an organic radical derived by removing two hydrogens from an alkane molecule of a saturated hydrocarbon in a straight-chain or branched form. Specific examples of the alkylene group may include methylene, ethylene, propylene, isopropylidene, isobutylidene, sec-butylidene, tert-butylidene, pentylene, isopentylene, hexylene, etc. One or more hydrogen atoms in the alkylene group may be substituted with the same substituents as in the case of the aryl group.

[0060] In addition, diarylamino in the present invention means an amino group in which a nitrogen atom is bonded to two aryl groups that are the same as or different from those described above, and diheteroarylamino in the present invention means an amino group in which a nitrogen atom is bonded to two heteroaryl groups that are the same as or different from each other, and the aryl(heteroaryl)amino means an amino group in which the aryl group and the heteroaryl group are respectively bonded to a nitrogen atom.

[0061] In addition, as a preferred example of the "substituted" in the "substituted or unsubstituted" in the [Chemical Formula A], it may be substituted with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 12 carbon atoms, haloalkyl group having 1 to 12 carbon atoms, alkenyl group having 2 to 12 carbon atoms, alkynyl group having 2 to 12 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms, heteroalkyl group having 1 to 12 carbon atoms, aryl group having 6 to 18 carbon atoms, arylalkyl group having 7 to 20 carbon atoms, alkylaryl group having 7 to 20 carbon atoms, heteroaryl group having 2 to 18 carbon atoms, heteroarylalkyl group having 2 to 18 carbon atoms, alkoxy group having 1 to 12 carbon atoms, alkylamino group having 1 to 12 carbon atoms, diarylamino group having 12 to 18 carbon atoms, diheteroarylamino group having 2 to 18 carbon atoms, aryl(heteroaryl)amino group having 7 to 18 carbon atoms, alkylsilyl group having 1 to 12 carbon atoms, arylsilyl group having 6 to 18 carbon atoms, aryloxy group having 6 to 18 carbon atoms, and arylsulfinyl group having 6 to 18 carbon atoms.

[0062] In the present invention, in the boron compound represented by the [Chemical Formula A], an unsaturated six-membered ring (six-membered ring including substituents R1 to R4) including a nitrogen atom (N) in a polycyclic condensed ring and an unsaturated five-membered ring including the nitrogen atom (N) and the linking group X in the unsaturated six-membered ring are condensed with each other to form an unsaturated bicyclic ring of "six-membered ring - five-membered ring".

[0063] In the five-membered ring of the unsaturated bicyclic ring having the "six-membered ring - five-membered ring" structure, two adjacent carbon atoms not included in the unsaturated six-membered ring are bonded to each other by a double bond, and the carbon atom between the nitrogen atom in the five-membered ring and the linking group X is bonded to the X by a double bond. One of the two carbon atoms bonded by a double bond in the five-membered ring is bonded to the boron (B) as the central atom, and the remaining one is bonded to the linking group Y. And, an aromatic six-membered ring including the substituents R9 to R 11 places the boron atom and the linking group Y between it and the unsaturated 5-membered ring and is connected to the unsaturated 5-membered ring.

[0064] And, the aromatic six-membered ring including the substituents R5 to R8 and the aromatic six-membered ring including the substituents R9 to R 11 have a structural feature of connecting with each other by placing the boron atom and the linking group Z as the central atoms of each other between them. When used as a light-emitting layer material in an organic light-emitting device, especially when used as a dopant, an organic light-emitting device with high efficiency and low voltage can be provided.

[0065] As an example, the linking group X in the [Chemical Formula A] may be a nitrogen (N) atom or C-H or C-D.

[0066] At this time, when the linking group X in the [Chemical Formula A] is a nitrogen atom (N), the unsaturated bicyclic "six-membered ring - five-membered ring" in the boron compound represented by the [Chemical Formula A] is equivalent to the structure represented by the following [Structural Formula B-1]. When the linking group X in the [Chemical Formula A] is C-H or C-D, the unsaturated bicyclic "six-membered ring - five-membered ring" in the boron compound represented by the [Chemical Formula A] is equivalent to the structure represented by the following [Structural Formula B-2].

[0067]

[0068] In the [Structural Formula B-1] and [Structural Formula B-2], "-*" represents a binding site for binding to the central atom boron (B) in the Chemical Formula A, and "-**" in the [Structural Formula B-1] and [Structural Formula B-2] represents a binding site for binding to the linking group Y in the Chemical Formula A.

[0069] That is, for the case where the linking group X according to an embodiment of the present invention is a nitrogen atom (N) or C-H or C-D, the structure of the novel boron compound is equivalent to a polycyclic ring represented by the [Structural Formula B-1] or [Structural Formula B-2] combined with boron (B) and the linking group Y, and an aromatic ring with 6 carbon atoms including the substituents R5 to R8 and an aromatic ring with 6 carbon atoms including the substituents R9 to R 11 are respectively combined with the boron (B) atom as the central atom, and the aromatic ring with 6 carbon atoms including the substituents R5 to R8 and the aromatic ring with 6 carbon atoms including the substituents R9 to R 11 are connected to each other by the linking group Z.

[0070] As an example, the linking group Y in the [Chemical Formula A] may be NR 14 or the linking group Z may be NR 17 , in which case, the R 14 and R 17 are the same as those defined above. Preferably, the linking group Y may be NR 14 , and the linking group Z may be NR 17 .

[0071] In addition, as an example, when the linking group Y in the [Chemical Formula A] is NR 14 or the linking group Z is NR 17 , preferably, the R 14 and R 17Each may be the same or different and may each independently be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.

[0072] In addition, as an example, in the [Chemical Formula A], the linking group Y is NR 14 or the linking group Z is NR 17 In this case, the R 14 and R 17 Each may be the same or different and may each independently be a substituent selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, and a substituted or unsubstituted fluorenyl group.

[0073] In addition, as an example of the boron compound represented by the [Chemical Formula A] according to the present invention, at least one of the substituents R1 to R 11 may be a substituent represented by -N(R 19 )(R 20 ). Preferably, one or two of the substituents R1 to R 11 may be a substituent represented by -N(R 19 )(R 20 ).

[0074] In addition, in the present invention, in the case where at least one of the substituents R1 to R 11 in the [Chemical Formula A] is a substituent represented by -N(R 19 )(R 20 ), it is preferably the case where one or two of the substituents R1 to R8 are substituents represented by -N(R 19 )(R 20 ).

[0075] In addition, as a more specific structural formula of the substituent represented by -N(R 19 )(R 20 ) according to the present invention, it may be a substituent represented by the following Structural Formula A.

[0076] [Structural Formula A]

[0077]

[0078] In the [Structural Formula A],

[0079] the linking groups L1 and L2 are the same or different and are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 18 carbon atoms,

[0080] The substituents Ar1 and Ar2 are the same as or different from each other, and are each independently any substituent selected from substituted or unsubstituted alkyl groups having 1 to 15 carbon atoms, substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 15 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 18 carbon atoms, and may be connected to each other to additionally form a monocyclic or polycyclic alicyclic or aromatic ring. More preferably, the substituent Ar1 in the [Structural Formula A] may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and the substituent Ar2 may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

[0081] Furthermore, in the case of the substituent represented by the [Structural Formula A], it is more preferably a substituent represented by the following [Structural Formula A-1] or [Structural Formula A-2].

[0082]

[0083] In the [Structural Formula A-1] and [Structural Formula A-2],

[0084] L1, L2, and Ar2 are the same as those defined in the preceding [Structural Formula A],

[0085] The substituent R 21 and R 22 are the same as those defined in R1 to R 17 in the [Chemical Formula A], respectively, and n is an integer from 1 to 7. In the case where n is 2 or more, each R 21 and R 22 are the same as or different from each other.

[0086] Furthermore, as an embodiment of the [Structural Formula A-1] and [Structural Formula A-2] according to the present invention, the substituent R 21 and R 22 are the same as or different from each other, and are each independently any one selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, and substituted or unsubstituted aryl groups having 6 to 50 carbon atoms.

[0087] In addition, as a specific example of the boron compound represented by the [Chemical Formula A] in the present invention, it may be any one selected from the following <Compound 1> to <Compound 132>.

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097] In addition, as an organic light-emitting device according to an embodiment of the present invention, the present invention provides an organic light-emitting device as follows, including: a first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode, and the organic layer includes one or more boron compounds represented by the prior [Chemical Formula A].

[0098] In addition, the expression in the present invention "(the organic layer) includes one or more organic compounds" can be interpreted as "(the organic layer) may include one organic compound belonging to the scope of the present invention or two or more different compounds belonging to the scope of the organic compound".

[0099] At this time, the organic light-emitting device of the present invention includes a light-emitting layer as the organic layer, and may include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, an electron blocking layer, an electron transport layer, an electron injection layer, and a cover layer in addition to the light-emitting layer.

[0100] As a more preferred embodiment of the present invention, the organic layer interposed between the first electrode and the second electrode of the present invention includes a light-emitting layer, wherein the light-emitting layer is composed of a host and a dopant, and at least one of the boron compounds represented by the [Chemical Formula A] in the present invention can be used as the dopant in the light-emitting layer. At this time, the light-emitting layer of the present invention may use an anthracene derivative represented by the following Chemical Formula D as the host.

[0101] [Chemical Formula D]

[0102]

[0103] In the [Chemical Formula D],

[0104] The substituent R 31 to R 38 are the same or different, and are respectively the same as those of R1 to R defined in the boron compound described above 17is the same as that defined above;

[0105] The substituents Ar9 and Ar 10 are each the same as or different from one another, and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms;

[0106] The linking group L 13 is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms,

[0107] k is an integer from 1 to 3, and in the case where k is 2 or more, each L 13 is the same as or different from one another, wherein the "substituted" in the substituted or unsubstituted is the same as that defined above.

[0108] In this case, preferably, the linking group L 13 is a single bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, k is an integer from 1 to 2, and in the case where k is 2 or more, each L 13 is the same as or different from one another.

[0109] In addition, as a specific substituent of the host compound in the present invention, Ar9 in the chemical formula D may be a substituent represented by the following chemical formula D-1.

[0110] [Chemical formula D-1]

[0111]

[0112] wherein the substituent R81 to R 85 are respectively the same or different and are the same as the content defined in the previously described R1 to R 17 ; and may combine with adjacent substituents to form a saturated or unsaturated ring.

[0113] As an example, as a specific compound of the anthracene derivative that can be used as the host, any one of the following [Chemical Formula D1] to [Chemical Formula D51] can be selected.

[0114]

[0115]

[0116]

[0117]

[0118] As a more preferred example of the present invention, the present invention provides an organic light-emitting device, including: an anode as a first electrode; a cathode as a second electrode facing the first electrode; and a light-emitting layer sandwiched between the anode and the cathode, wherein at least one of the boron compounds represented by the [Chemical Formula A] in the present invention is included as a dopant in the light-emitting layer, and at least one of the compounds represented by the [Chemical Formula D] is included as a host in the light-emitting layer. According to this structural feature, the organic light-emitting device according to the present invention can have the characteristics of low-voltage driving and high efficiency.

[0119] At this time, the content of the dopant in the light-emitting layer can generally be selected in the range of about 0.01 parts by weight to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

[0120] In addition, in addition to the dopant and the host, the light-emitting layer may additionally include various host and various dopant substances.

[0121] Hereinafter, an organic light-emitting device according to an example of the present invention will be described with reference to the drawings.

[0122] Figure 1 is a diagram showing the structure of an organic light-emitting device according to an example of the present invention.

[0123] As shown in Figure 1As shown, the organic light-emitting device according to an embodiment of the present invention is an organic light-emitting device that sequentially includes an anode 20, a hole transport layer 40, a light-emitting layer 50 including a host and a dopant, an electron transport layer 60, and a cathode 80. That is, the anode is used as the first electrode, the cathode is used as the second electrode, a hole transport layer is included between the anode and the light-emitting layer, and an electron transport layer is included between the light-emitting layer and the cathode.

[0124] Moreover, the organic light-emitting device according to an embodiment of the present invention may include a hole injection layer 30 between the anode 20 and the hole transport layer 40, and an electron injection layer 70 between the electron transport layer 60 and the cathode 80.

[0125] Referring to the Figure 1 The organic light-emitting device of the present invention and its manufacturing method will be described as follows.

[0126] First, a positive electrode (anode) electrode material is coated on the upper part of the substrate 10 to form the anode 20. Among them, the substrate 10 is a substrate used in general organic EL devices, but an organic substrate or a transparent plastic substrate with excellent transparency, surface smoothness, processability, and waterproofness is preferred. In addition, the anode electrode material uses transparent and highly conductive indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc.

[0127] The hole injection layer material is vacuum thermally deposited or spin-coated on the upper part of the anode 20 electrode to form the hole injection layer 30. Then, the hole transport layer material is vacuum thermally deposited or spin-coated on the upper part of the hole injection layer 30 to form the hole transport layer 40.

[0128] As long as the hole injection layer material is a material commonly used in the art, it can be used without special restrictions. For example, 4,4',4”-tris(2-naphthylphenyl-phenylamino)-triphenylamine (2-TNATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), 2,3,6,7,10,11-hexacyanohexaazatriphenylene (HAT-CN), etc. can be used. However, the present invention is not necessarily limited thereto.

[0129] Moreover, as the material of the hole transport layer, as long as it is a material commonly used in the art, it can be used without special restrictions. For example, N,N'-di(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (α-NPD), etc. can be used. However, the present invention is not necessarily limited thereto.

[0130] In addition, an electron blocking layer can be additionally formed on the upper part of the hole transport layer in the present invention. The electron blocking layer is a layer for preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole transport layer, thereby improving the lifespan and efficiency of the device. A known material can be used, or two known materials can be mixed as necessary and formed at a suitable part between the light-emitting layer and the hole injection layer. Preferably, it can be formed between the light-emitting layer and the hole transport layer.

[0131] Then, the light-emitting layer 50 can be stacked on the upper part of the hole transport layer 40 or the electron blocking layer by a vacuum deposition method or a spin coating method.

[0132] Among them, the light-emitting layer may be composed of a host and a dopant, and the materials constituting them are as described previously.

[0133] Moreover, according to a specific example of the present invention, the thickness of the light-emitting layer is preferably to

[0134] Then, an electron transport layer 60 is deposited on the light-emitting layer by a vacuum deposition method or a spin coating method.

[0135] In addition, the material of the electron transport layer in the present invention is a material that functions to stably transport electrons injected from an electron injection electrode (cathode), and a known electron transport substance can be used. As an example of a known electron transport substance, quinoline derivatives can be adopted. In particular, tris(8-hydroxyquinoline) aluminum (Alq3), Liq, TAZ, BAlq, beryllium bis(benzoquinolin-10-olate: Bebq2), Compound 201, Compound 202, BCP, PBD, BMD, BND, etc. which are oxadiazole derivatives and the like can be used, but it is not limited thereto.

[0136]

[0137] Furthermore, in the organic light-emitting device of the present invention, an electron injection layer (EIL) which is a material having a function of enabling electrons to be easily injected from the cathode can be stacked on top of the electron transport layer after the electron transport layer is formed, and its material is not particularly limited.

[0138] As the material for forming the electron injection layer, any known substance such as CsF, NaF, LiF, Li2O, BaO, etc. can be used as the material for forming the electron injection layer. Although the deposition conditions of the electron injection layer vary depending on the compound used, they can generally be selected from a range substantially the same as the conditions for forming the hole injection layer.

[0139] The thickness of the electron injection layer can be about to about about to about If the thickness of the electron injection layer satisfies the aforementioned range, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.

[0140] Also, in the present invention, the cathode can use a substance with a small work function to easily inject electrons. Substances such as lithium (Li), magnesium (Mg), calcium (Ca), or their alloys like aluminum (Al), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. can be used, or a transmissive cathode using ITO or IZO can be adopted.

[0141] Also, in the present invention, the organic light-emitting element can additionally include a light-emitting layer that emits light in the wavelength range of 380 nm to 800 nm, such as a blue light-emitting material, a green light-emitting material, or a red light-emitting material. That is, the light-emitting layer in the present invention is a plurality of light-emitting layers, and the blue light-emitting material, green light-emitting material, or red light-emitting material in the additionally formed light-emitting layer can be a fluorescent material or a phosphorescent material.

[0142] Also, in the present invention, one or more layers selected from each of the said layers can be formed by a single-molecule deposition process or a solution process.

[0143] Among them, the deposition process refers to a method of forming a thin film by evaporating a substance used as a material for forming each of the said layers through heating, etc. in a vacuum or low-pressure state, and the solution process refers to a method of mixing a substance used as a material for forming each of the said layers with a solvent and forming a thin film by methods such as inkjet printing, roll-to-roll coating, screen printing, spraying, dip coating, spin coating, etc.

[0144] In addition, the organic light-emitting element in the present invention can be used in any one of a flat panel display device, a flexible display device, a monochromatic or white flat panel lighting device, and a monochromatic or white flexible lighting device.

[0145] Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these embodiments are only used to more specifically illustrate the present invention, and those with basic knowledge in the art can clearly understand that the scope of the present invention is not limited thereto.

[0146] (Embodiment)

[0147] Synthesis Example 1. Synthesis of Compound 1

[0148] Synthesis Example 1-(1): Synthesis of Intermediate 1-a

[0149]

[0150] Under nitrogen, 50 g (423 mmol) of imidazopyridine, 75.3 g (423 mmol) of N-bromosuccinimide, and 500 ml of dimethylformamide were added to a round-bottom flask and stirred at room temperature for 12 hours. After the reaction was completed, the reaction product was separated and the organic layer was concentrated under reduced pressure, and then separated by column chromatography to obtain 67 g of <Intermediate 1-a>. (Yield 81%)

[0151] Synthesis Example 1-(2): Synthesis of Intermediate 1-b

[0152]

[0153] 67 g (340 mmol) of <Intermediate 1-a>, 41.2 g (442 mmol) of aniline, 6.2 g (6.8 mmol) of tris(dibenzylideneacetone)dipalladium, 65.3 g (680 mmol) of sodium tert-butoxide, 8.5 g (13.6 mmol) of 2,2'-bis(diphenylphosphine)-1,1'-binaphthyl, and 700 ml of toluene were added to a round-bottom flask and refluxed for 12 hours. After the reaction was completed, the reaction product was separated and the organic layer was concentrated under reduced pressure, and then separated by column chromatography to obtain 52.6 g of <Intermediate 1-b>. (Yield 74%)

[0154] Synthesis Example 1-(3): Synthesis of Intermediate 1-c

[0155]

[0156] 52.6 g (251 mmol) of <Intermediate 1-b>, 56.8 g (251 mmol) of 1-bromo-2,3-dichlorobenzene, 4.6 g (5.0 mmol) of tris(dibenzylideneacetone)dipalladium, 48.3 g (502 mmol) of sodium tert-butylate, 4.9 g (10.0 mmol) of tri-tert-butylphosphine and 500 ml of toluene were added to a round-bottom flask and refluxed for 12 hours. After the reaction was completed, the reaction product was separated and the organic layer was concentrated under reduced pressure, and then separated by column chromatography to obtain 61.3 g of <Intermediate 1-c>. (Yield 48%)

[0157] Synthesis Example 1-(4): Synthesis of Intermediate 1-d

[0158]

[0159] The intermediate 1-d was obtained by the same method as in Synthesis Example 1-(1), except that 4-tert-butylaniline was used instead of the imidazopyridine used in Synthesis Example 1-(1). (Yield: 75%)

[0160] Synthesis Example 1-(5): Synthesis of Intermediate 1-e

[0161]

[0162] Under nitrogen atmosphere, 30 g (131 mmol) of <Intermediate 1-d>, 19.2 g (157 mmol) of phenylboronic acid, 3.0 g (2.6 mmol) of tetrakis(triphenylphosphine)palladium, 27.2 g (197 mmol) of potassium carbonate, 150 ml of toluene, 150 ml of 1,4-dioxane, and 90 ml of water were added to a round-bottom flask and refluxed for 12 hours. After completion of the reaction, the reaction product was subjected to layer separation and the organic layer was concentrated under reduced pressure, and then separated by column chromatography to obtain 23.1 g of <Intermediate 1-e>. (Yield: 78%)

[0163] Synthesis Example 1-(6): Synthesis of Intermediate 1-f

[0164]

[0165] Except for using 1-bromo-4-tert-butylbenzene instead of <Intermediate 1-a> used in Synthesis Example 1-(2) and using <Intermediate 1-e> instead of aniline used in Synthesis Example 1-(2), <Intermediate 1-f> was synthesized in the same manner as in Synthesis Example 1-(2). (Yield: 75%)

[0166] Synthesis Example 1-(7): Synthesis of Intermediate 1-g

[0167]

[0168] Except for using 1-iodo-3-bromobenzene instead of <Intermediate 1-a> used in Synthesis Example 1-(2) and using <Intermediate 1-f> instead of aniline used in Synthesis Example 1-(2), <Intermediate 1-g> was synthesized in the same manner as in Synthesis Example 1-(2). (Yield: 65%)

[0169] Synthesis Example 1-(8): Synthesis of Intermediate 1-h

[0170]

[0171] Except for using <Intermediate 1-g> instead of <Intermediate 1-a> used in Synthesis Example 1-(2), <Intermediate 1-h> was synthesized in the same manner as in Synthesis Example 1-(2). (Yield: 72%)

[0172] Synthesis Example 1-(9): Synthesis of Intermediate 1-i

[0173]

[0174] Except for using <Intermediate 1-h> instead of <Intermediate 1-b> used in Synthesis Example 1-(3) and using <Intermediate 1-c> instead of 1-bromo-2,3-dichlorobenzene, <Intermediate 1-i> was synthesized in the same manner as in Synthesis Example 1-(3). (Yield: 66%)

[0175] Synthesis Example 1-(10): Synthesis of Compound 1

[0176]

[0177] 30 g (35.6 mmol) of <Intermediate 1-i> and 300 ml of tert-butylbenzene were added to a round-bottom flask and stirred under a nitrogen atmosphere. After the temperature was lowered to 0 °C, 46 ml (78.3 mmol) of 1.7 M tert-butyllithium was added dropwise, and then the mixture was stirred at 60 °C for 3 hours. After that, the temperature was lowered to -30 °C, 17.8 g (71.2 mmol) of boron tribromide was added, and the mixture was stirred at room temperature for 1 hour. Then, 9.2 g (71.2 mmol) of diisopropylethylamine was added, and the mixture was stirred at 120 °C for 3 hours. After the reaction was completed, the reaction product was subjected to layer separation, the organic layer was concentrated under reduced pressure, and then separated by column chromatography to obtain 2.3 g of <Compound 1>. (Yield: 18%)

[0178] MS (MALDI-TOF): m / z 815.42 [M +

[0179] Synthesis Example 2. Compound 8 Synthesis

[0180] Synthesis Example 2-(1): Synthesis of Intermediate 2-a

[0181]

[0182] Except for using 1-bromo-2,3-dichloro-5-tert-butylbenzene instead of 1-bromo-2,3-dichlorobenzene used in Synthesis Example 1-(3), <Intermediate 2-a> was synthesized in the same manner as in Synthesis Example 1-(3). (Yield: 62%)

[0183] Synthesis Example 2-(2): Synthesis of Intermediate 2-b

[0184]

[0185] ​Except for using bis(4-(tert-butyl)phenyl)amine instead of <Intermediate 1-b> used in Synthesis Example 1-(3) and using 1,3-dibromobenzene instead of 1-bromo-2,3-dichlorobenzene used in Synthesis Example 1-(3), <Intermediate 2-b> was obtained by synthesis in the same manner as in Synthesis Example 1-(3). (Yield: 68%)

[0186] Synthesis Example 2-(3): Synthesis of Intermediate 2-c

[0187]

[0188] Except for using <Intermediate 2-b> instead of <Intermediate 1-a> used in Synthesis Example 1-(2) and using 4-aminodibenzofuran instead of aniline used in Synthesis Example 1-(2), <Intermediate 2-c> was synthesized in the same manner as in Synthesis Example 1-(2). (Yield: 60%)

[0189] Synthesis Example 2-(4): Synthesis of Intermediate 2-d

[0190]

[0191] Except for using <Intermediate 2-c> instead of <Intermediate 1-b> used in Synthesis Example 1-(3) and using <Intermediate 2-a> instead of 1-bromo-2,3-dichlorobenzene used in Synthesis Example 1-(3), <Intermediate 2-d> was synthesized in the same manner as in Synthesis Example 1-(3). (Yield: 60%)

[0192] Synthesis Example 2-(5): Synthesis of Compound 8

[0193]

[0194] Except for using <Intermediate 2-d> instead of <Intermediate 1-i> used in Synthesis Example 1-(10), <Compound 8> was synthesized in the same manner as in Synthesis Example 1-(10). (Yield: 20%)

[0195] MS(MALDI-TOF): m / z 885.46 [M +

[0196] Synthesis Example 3. Synthesis of Compound 12

[0197] Synthesis Example 3-(1): Synthesis of Intermediate 3-a

[0198]

[0199] ​Except for using 1-iodo-3-bromobenzene in place of <Intermediate 1-a> used in Synthesis Example 1-(2) and using N-(4-tert-butylphenyl)naphthalen-1-amine in place of aniline used in Synthesis Example 1-(2), <Intermediate 3-a> was synthesized in the same manner as in Synthesis Example 1-(2). (Yield: 65%)

[0200] Synthesis Example 3-(2): Synthesis of Intermediate 3-b

[0201]

[0202] Except for using <Intermediate 3-a> in place of <Intermediate 1-a> used in Synthesis Example 1-(2), <Intermediate 3-b> was synthesized in the same manner as in Synthesis Example 1-(2). (Yield: 72%)

[0203] Synthesis Example 3-(3): Synthesis of Intermediate 3-c

[0204]

[0205] Except for using <Intermediate 2-a> in place of <Intermediate 1-c> used in Synthesis Example 1-(9) and using <Intermediate 3-b> in place of <Intermediate 1-h> used in Synthesis Example 1-(9), <Intermediate 3-c> was synthesized in the same manner as in Synthesis Example 1-(9). (Yield: 62%)

[0206] Synthesis Example 3-(4): Synthesis of Compound 12

[0207]

[0208] Except for using <Intermediate 3-c> in place of <Intermediate 1-i> used in Synthesis Example 1-(10), <Compound 12> was synthesized in the same manner as in Synthesis Example 1-(10). (Yield: 18%)

[0209] MS(MALDI-TOF): m / z 789.40 [M +

[0210] Synthesis Example 4. Synthesis of Compound 13

[0211] Synthesis Example 4-(1): Synthesis of Intermediate 4-a

[0212]

[0213] ​To a round-bottomed flask, 50 g (253 mmol) of 6-bromo-imidazo[1,2-a]pyridine, 8.3 g (12.6 mmol) of bis(triphenylphosphine)nickel(II) dichloride, and 500 ml of tetrahydrofuran were added, and the mixture was stirred under a nitrogen atmosphere. After dropwise adding 49.2 g (304 mmol) of tert-butylmagnesium bromide at 0 °C, the mixture was refluxed for 12 hours. After completion of the reaction, the reaction product was subjected to layer separation, the organic layer was concentrated under reduced pressure, and then separated by column chromatography to obtain 28.7 g of <Intermediate 4-a>. (Yield 65%)

[0214] Synthesis Example 4-(2): Synthesis of Compound 13

[0215]

[0216] Except for using <Intermediate 4-b> instead of <Intermediate 1-i> used in Synthesis Example 1-(10), <Compound 13> was synthesized in the same manner as in Synthesis Example 1-(10), wherein the <Intermediate 4-b> was obtained by synthesizing in the same manner as in Synthesis Example 1-(9) except for using <Intermediate 4-a> instead of imidazo[1,2-a]pyridine used in Synthesis Example 1-(1), using 1-bromo-2,3-dichloro-5-tert-butylbenzene instead of 1-bromo-2,3-dichlorobenzene in Synthesis Example 1-(3), and using <Intermediate 3-b> instead of <Intermediate 1-h> used in Synthesis Example 1-(9).

[0217] MS (MALDI-TOF): m / z 845.46 [M +

[0218] Synthesis Example 5. Synthesis of Compound 58

[0219] Synthesis Example 5-(1): Synthesis of Intermediate 5-a

[0220]

[0221] Except for using 3-bromoindolizine instead of imidazo[1,2-a]pyridine used in Synthesis Example 1-(1) and using 1-bromo-2,3-dichloro-5-tert-butylbenzene instead of 1-bromo-2,3-dichlorobenzene used in Synthesis Example 1-(3), <Intermediate 5-a> was synthesized in the same manner as in Synthesis Examples 1-(1) to 1-(3). (Yield 52%)

[0222] Synthesis Example 5-(2): Synthesis of Intermediate 5-b

[0223]

[0224] ​Except for using <Intermediate 1-h> instead of <Intermediate 1-b> used in Synthesis Example 1-(3), and using <Intermediate 5-a> instead of 1-bromo-2,3-dichlorobenzene used in Synthesis Example 1-(3), <Intermediate 5-b> was synthesized in the same manner as in Synthesis Example 1-(3). (Yield: 63%)

[0225] Synthesis Example 5-(3): Synthesis of Compound 58

[0226]

[0227] Except for using <Intermediate 5-b> instead of <Intermediate 1-i> used in Synthesis Example 1-(10), <Compound 58> was synthesized in the same manner as in Synthesis Example 1-(10). (Yield: 19%)

[0228] MS(MALDI-TOF): m / z 870.48 [M +

[0229] Synthesis Example 6 . Synthesis of Compound 68

[0230] Synthesis Example 6-(1): Synthesis of Intermediate 6-a

[0231]

[0232] Except for using <Intermediate 5-a> instead of <Intermediate 1-c> used in Synthesis Example 1-(9), and using <Chemical Formula 6-a> instead of <Intermediate 1-h> used in Synthesis Example 1-(9), <Intermediate 6-a> was synthesized in the same manner as in Synthesis Example 1-(9). (Yield: 65%)

[0233] Synthesis Example 6-(2): Synthesis of Compound 68

[0234]

[0235] Except for using <Intermediate 6-a> instead of <Intermediate 1-i> used in Synthesis Example 1-(10), <Compound 68> was synthesized in the same manner as in Synthesis Example 1-(10). (Yield: 20%)

[0236] MS(MALDI-TOF): m / z 808.37 [M +

[0237] Synthesis Example 7 . Synthesis of Compound 89

[0238] Synthesis Example 7-(1): Synthesis of Intermediate 7-a

[0239] ​​

[0240] Except for using 3-bromoindolizine in place of <Intermediate 1-a> used in Synthesis Example 1-(2), and using 1-bromo-2,3-dichloro-5-methylbenzene in place of 1-bromo-2,3-dichlorobenzene in Synthesis Example 1-(3), <Intermediate 7-a> was synthesized in the same manner as in Synthesis Examples 1-(2) to 1-(3). (Yield 50%)

[0241] Synthesis Example 7-(2): Synthesis of Intermediate 7-b

[0242]

[0243] Except for using <Intermediate 7-a> in place of <Intermediate 1-c> used in Synthesis Example 1-(9), and using <Chemical Formula 7-a> in place of <Intermediate 1-h> used in Synthesis Example 1-(9), <Intermediate 7-b> was synthesized in the same manner as in Synthesis Example 1-(9). (Yield 66%)

[0244] Synthesis Example 7-(3): Synthesis of Compound 89

[0245]

[0246] Except for using <Intermediate 7-b> in place of <Intermediate 1-i> used in Synthesis Example 1-(10), <Compound 89> was synthesized in the same manner as in Synthesis Example 1-(10). (Yield 19%)

[0247] MS(MALDI-TOF): m / z 836.37 [M +

[0248] Synthesis Example 8. Synthesis of Compound 98

[0249] Synthesis Example 8-(1): Synthesis of Intermediate 8-a

[0250]

[0251] Except for using 7-bromoindolizine in place of imidazopyridine used in Synthesis Example 1-(1), and using N-chlorosuccinimide in place of N-bromosuccinimide used in Synthesis Example 1-(1), <Intermediate 8-a> was synthesized in the same manner as in Synthesis Example 1-(1). (Yield 68%)

[0252] Synthesis Example 8-(2): Synthesis of Intermediate 8-b

[0253]

[0254] ​Except for using <Intermediate 8-a> instead of <Intermediate 1-a> used in Synthesis Example 1-(2) and using diphenylamine instead of aniline used in Synthesis Example 1-(2), <Intermediate 8-b> was synthesized in the same manner as in Synthesis Example 1-(2). (Yield: 77%)

[0255] Synthesis Example 8-(3): Synthesis of Intermediate 8-c

[0256]

[0257] Except for using <Intermediate 8-b> instead of <Intermediate 1-a> used in Synthesis Example 1-(2), <Intermediate 8-c> was synthesized in the same manner as in Synthesis Examples 1-(2) to 1-(3). (Yield: 55%)

[0258] Synthesis Example 8-(4): Synthesis of Intermediate 8-d

[0259]

[0260] Except for using <Intermediate 8-c> instead of <Intermediate 1-c> used in Synthesis Example 1-(9) and using <Chemical Formula 8-a> instead of <Intermediate 1-h> used in Synthesis Example 1-(9), <Intermediate 8-d> was synthesized in the same manner as in Synthesis Example 1-(9). (Yield: 65%)

[0261] Synthesis Example 8-(5): Synthesis of Compound 98

[0262]

[0263] Except for using <Intermediate 8-d> instead of <Intermediate 1-i> used in Synthesis Example 1-(10), <Compound 98> was synthesized in the same manner as in Synthesis Example 1-(10). (Yield: 20%)

[0264] MS (MALDI-TOF): m / z 1045.49 [M +

[0265] Example 1 ~ Example 8: Fabrication of Organic Light-Emitting Device

[0266] After patterning to make the light-emitting area of the ITO glass 2 mm × 2 mm in size, it was cleaned. After installing the above ITO glass in a vacuum chamber, the base pressure was brought to 1 × 10 -7 Torr, and then with DNTPD α-NPD ​Form a film on top of the ITO in the stated order. For the light-emitting layer, mix [BH] as the host with the compound of the present invention (3 wt%) as the dopant and form a film. After that, then [Chemical formula E-1] and [Chemical formula E-2] Mix in a ratio of 1:1 and form a film as the electron transport layer, and sequentially form [Chemical formula E-1] Form Al into a film as the electron injection layer, thereby manufacturing an organic light-emitting device. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.

[0267]

[0268]

[0269] Comparative Examples 1 to 3

[0270] Except for separately using the following [BD1] to [BD3] to replace the dopant compounds used in Examples 1 to 8, an organic light-emitting device was manufactured in the same manner, and the light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA. The structures of [BD1], [BD2], and [BD3] are as follows.

[0271]

[0272] [Table 1]

[0273]

[0274]

[0275] As shown in Examples 1 to 8 above, compared with the cases of Comparative Examples 1 to 3, the boron compounds according to the present invention exhibit higher quantum efficiency and low-voltage characteristics, indicating high availability as organic light-emitting devices.

[0276] Industrial availability

[0277] When manufacturing an organic light-emitting device using the boron compound of the present invention for the light-emitting layer, compared with existing compounds, the low-voltage and high-efficiency characteristics are improved. When applied to an organic light-emitting device, improved characteristics are exhibited, so that the industrial availability is high in the field of organic light-emitting devices and related industries.

Claims

1. A boron compound, characterized in that, It is represented by the following [Chemical Formula A]: [Chemical Formula A] In the said [Chemical Formula A], Wherein Y is NR 14 , What is Z is NR 17 , wherein X is CR 18 or a nitrogen atom, The substituents R1 to R 11 are the same as or different from one another and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, nitro, cyano, halogen, and -N(R 19 )(R 20 ), any one of them, R 14 and R 17 are the same as or different from each other and are each independently selected from any one of a substituted or unsubstituted aryl group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms The substituent R 18 to R 20 are each independently the same or different and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms. wherein, in the said [Chemical Formula A], the "substituted" in the "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of the following substituents: deuterium, cyano group, halogen group, nitro group, alkyl group having 1 to 24 carbon atoms, haloalkyl group having 1 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, diarylamino group having 12 to 24 carbon atoms, diheteroarylamino group having 2 to 24 carbon atoms, aryl(heteroaryl)amino group having 7 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms, arylsilyl group having 6 to 24 carbon atoms.

2. The boron compound according to claim 1, characterized in that, The said X is a nitrogen atom.

3. The boron compound according to claim 1, characterized in that, The said X is C-H or C-D.

4. The boron compound according to claim 1, characterized in that, Said R 14 and R 17 are each the same or different and are, independently of one another, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.

5. The boron compound according to claim 4, characterized in that, Said R 14 and R 17 are each independently the same as or different from each other, and are each a substituent selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, and substituted or unsubstituted fluorenyl.

6. The boron compound according to claim 1, characterized in that, At least one of the substituents R1 to R 11 is a substituent represented by -N(R 19 )(R 20 ).

7. The boron compound according to claim 6, characterized in that, One or two of the substituents R1 to R 11 are substituents represented by -N(R 19 )(R 20 ).

8. The boron compound according to claim 6, characterized in that, One or two of the substituents R1 to R8 are substituents represented by -N(R 19 )(R 20 ).

9. The boron compound according to claim 1, characterized in that, The substituent -N(R 19 )(R 20 ) is a substituent represented by the following structural formula A: [Structural Formula A] In the said [Structural Formula A], the said linking groups L1 and L2 are the same as or different from each other, and are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, the said substituents Ar1 and Ar2 are the same as or different from each other, and are each independently a substituent selected from any one of a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 15 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.

10. The boron compound according to claim 1, characterized in that, The compound represented by the said [Chemical Formula A] is selected from any one of the following <Compound 1> to <Compound 51>, <Compound 55> to <Compound 105>, <Compound 109> to <Compound 114>, <Compound 116>, <Compound 127> to <Compound 132>:

11. An organic light-emitting element, comprising: The first electrode; The second electrode, facing the first electrode; and The organic layer, sandwiched between the first electrode and the second electrode, wherein the organic layer includes one or more boron compounds described in any one of claims 1 to 10.

12. The organic light-emitting element according to claim 11, wherein, The organic layer includes at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and a covering layer.

13. The organic light-emitting element according to claim 11, wherein, The organic layer sandwiched between the first electrode and the second electrode includes a light emitting layer, wherein the light emitting layer is composed of a host and a dopant, and the boron compound represented by the said [Chemical Formula A] is used as the dopant.

14. The organic light-emitting element according to claim 13, wherein, The light emitting layer uses an anthracene derivative represented by the following Chemical Formula D as the host: [Chemical Formula D] In the said [Chemical Formula D], The substituent R 31 to R 38 are the same as or different from one another and are respectively the same as the definitions of R1 to R 11 defined in claim 1; The substituents Ar9 and Ar 10 are the same as or different from each other and are each independently any one selected from substituted or unsubstituted aryl groups having 6 to 50 carbon atoms and substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms; The linking group L 13 is any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms. where k is an integer from 1 to 3, and in the case where k is 2 or more, each L 13 is the same as or different from each other, wherein, the "substituted" in the "substituted or unsubstituted" is the same as that defined in claim 1.

15. The organic light-emitting element according to claim 14, wherein, Ar9 in the said Chemical Formula D is a substituent represented by the following Chemical Formula D-1: [Chemical Formula D-1] The substituent R 81 to R 85 are the same as or different from each other and are respectively the same as the definitions of R1 to R 11 defined in Claim 1 above.

16. The organic light-emitting element according to claim 12, wherein, One or more layers selected from each of the said layers are formed by a deposition process or a solution process.

17. The organic light-emitting element according to claim 11, wherein, The organic light-emitting element is used in any one of a flat panel display device, a flexible display device, a monochromatic or white flat panel lighting device, and a monochromatic or white flexible lighting device.

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