Organic light emitting diode including Novel Anthracene compounds

Abstract

The present invention relates to an organic light-emitting device comprising a novel anthracene compound, and more specifically, to an organic light-emitting device comprising an anthracene compound represented by [Chemical Formula A]; and a compound represented by [Chemical Formula B-1] or [Chemical Formula B-2], respectively, wherein [Chemical Formula A], [Chemical Formula B-1] and [Chemical Formula B-2] are as defined in the detailed description of the invention.

Description

Technology Field

[0001] The present invention relates to an organic light-emitting device comprising a novel anthracene compound, and more specifically, to an organic light-emitting device comprising a specific type of host and dopant material within the organic light-emitting device, thereby enabling device characteristics such as high efficiency and a long lifespan. Background Technology

[0002] Organic light-emitting diodes are self-emissive devices that have the advantages of a wide viewing angle and excellent contrast, as well as fast response time, excellent brightness, driving voltage and response speed characteristics, and the ability to be multicolored.

[0003] A typical organic light-emitting diode includes an organic light-emitting layer that emits light, and an anode and a cathode facing each other with the organic light-emitting layer in between.

[0004] More specifically, the organic light-emitting device may have a structure in which a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially formed on the anode. Here, the hole transport layer, the light-emitting layer, and the electron transport layer are organic thin films composed of organic compounds.

[0005] The driving principle of an organic light-emitting device having the structure described above is as follows. When a voltage is applied between the anode and the cathode, holes injected from the anode move to the light-emitting layer via the hole transport layer, and electrons injected from the cathode move to the light-emitting layer via the electron transport layer. Carriers such as holes and electrons recombine in the light-emitting layer region to generate excitons. Light is generated as these excitons change from an excited state to a ground state.

[0006] Meanwhile, materials used as organic layers in organic light-emitting devices can be classified according to their function into light-emitting materials and charge-transporting materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials. The light-emitting materials can be classified according to their light emission mechanism into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons.

[0007] In addition, when only one material is used as the light-emitting material, problems arise such as the maximum emission wavelength shifting to a longer wavelength due to intermolecular interactions, resulting in reduced color purity or decreased device efficiency due to light attenuation effects. Therefore, a host-dopant system can be used as the light-emitting material to increase color purity and luminous efficiency through energy transfer. The principle is that when a small amount of a dopant, which has a smaller energy band gap than the host forming the light-emitting layer, is mixed into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, emitting high-efficiency light. At this time, since the wavelength of the host shifts to the wavelength range of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.

[0008] Meanwhile, research is being conducted to introduce deuterium-substituted compounds as materials, such as in the light-emitting layer, to improve the lifespan and stability of organic light-emitting diodes.

[0009] Generally, compounds substituted with deuterium are known to show differences in thermodynamic behavior compared to compounds bonded with hydrogen, because the atomic mass of deuterium is twice that of hydrogen, which can lead to lower zero-point energy and lower vibrational energy levels.

[0010] In addition, physicochemical properties such as chemical bond lengths associated with deuterium differ from those of hydrogen. In particular, the elongation amplitude of CD bonds is smaller than that of CH bonds, so the van der Waals radius of deuterium is smaller than that of hydrogen. Generally, CD bonds are shorter and stronger than CH bonds. When substituted with deuterium, the ground state energy is lowered, and as the bond length between deuterium and carbon shortens, the molecular hardcore volume decreases. Consequently, electrical polarizability can be reduced, and the thin film volume can be increased by weakening intermolecular interactions.

[0011] These characteristics can lower the crystallinity of the thin film, that is, create an amorphous state, which can generally be effective for increasing OLED lifespan and driving characteristics, and can further improve heat resistance.

[0012] As prior art related to the above-mentioned organic light-emitting compounds containing deuterium, Registered Patent Publication No. 10-1111406 describes a technology for providing low-voltage driving and long-life devices by substituting an amine-based compound containing carbazole with deuterium or mixing compounds substituted with deuterium, and Registered Patent Publication No. 10-1068224 describes a technology for using an anthracene compound containing a phenyl group in which the hydrogen in the phenyl group is substituted with deuterium as a host.

[0013] However, despite the fact that various methods have been attempted to manufacture organic light-emitting diodes with long lifespan characteristics in the prior art including the aforementioned prior art, there is still a continuous demand for the development of organic light-emitting diodes with even better long lifespan characteristics. Prior art literature

[0014] Registered Patent Publication No. 10-1111406 (April 12, 2012) Registered Patent Publication No. 10-1068224 (September 28, 2011) The problem to be solved

[0015] The present invention aims to solve the aforementioned problems by introducing an organic light-emitting diode (OLED) containing an anthracene compound that can provide improved long-life characteristics by using an anthracene compound having specific structural features as a host for the light-emitting layer in the organic light-emitting diode, and also using a boron compound of a specific structure as a dopant. means of solving the problem

[0016] The present invention provides an organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises a light-emitting layer comprising a host and a dopant, wherein the host comprises at least one of anthracene compounds represented by [Chemical Formula A], and the dopant comprises at least one of compounds represented by [Chemical Formula B-1] or [Chemical Formula B-2].

[0017] [Chemical Formula A] [Structural Formula 1]

[0018]

[0019] In the above [Chemical Formula A],

[0020] The above A is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted aliphatic aromatic group having 3 to 50 carbon atoms.

[0021] It is any one selected from among the mixed rings, and

[0022] The above R1 is hydrogen or deuterium, and

[0023] The above R, R2 to R 12 The are identical or different from one another and each independently 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 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 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 50 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 6 to 50 carbon atoms. Any one selected from an arylthioxy group, a substituted or unsubstituted amine group having 0 to 30 carbon atoms, a substituted or unsubstituted silyl group having 0 to 30 carbon atoms, a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, a cyano group, a nitro group, and a halogen group, and each of these can be connected to adjacent substituents to additionally form an aliphatic or aromatic single or polycyclic ring and an aliphatic aromatic mixed ring.

[0024] The above n is an integer from 1 to 8, wherein if n is 2 or greater, each R is the same or different from each other, and

[0025] The above R5 to R in the above structural formula 1 12 One of them is a single bond that bonds to an aromatic carbon atom within the anthracene of the above chemical formula A, and

[0026] However, at least one substituent in [Formula A] above is substituted with deuterium or is a substituent containing deuterium.

[0027] [Chemical Formula B-1] [Chemical Formula B-2]

[0028]

[0029] In the above [Chemical Formula B-1] and [Chemical Formula B-2],

[0030] The above A1 to A3 are identical or different from one another and are each independently selected from an aromatic hydrocarbon ring having 6 to 50 carbon atoms that is substituted or unsubstituted, an aromatic heterocycle having 2 to 50 carbon atoms that is substituted or unsubstituted, an aliphatic ring having 3 to 30 carbon atoms that is substituted or unsubstituted, and an aliphatic-aromatic mixed ring having 3 to 30 carbon atoms that is substituted or unsubstituted, and each substituent within the A1 to A3 rings may be connected to adjacent substituents to additionally form a monocyclic or polycyclic ring of an aliphatic or aromatic group.

[0031] The above Y1 and Y2 are identical or different from each other, and each independently, NR 21 , CR 22 R 23 , O, S, Se and SiR 24 R 25 It is one of the selected from among, and

[0032] The above R 21 to R 25The groups are identical or different from one another and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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 heterocycloalkyl 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 amine group having 0 to 30 carbon atoms, a substituted or unsubstituted silyl group having 0 to 30 carbon atoms, It is any one selected from a substituted or unsubstituted aliphatic aromatic mixed ring having 3 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group, and

[0033] The above R 21 to R 25 Each can additionally form a monocyclic or polycyclic ring of alicyclic or aromatic by combining with one or more rings selected from the above A1 to A3 rings, and

[0034] The above R 22 and R 23 , R 24 and R 25 Each of these can be connected to each other to additionally form alicyclic or aromatic single or polycyclic rings, and

[0035] The term 'substituted' in 'substituted or unsubstituted' within [Chemical Formula A], [Chemical Formula B-1], and [Chemical Formula B-2] above refers to deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, cycloalkyl group having 3 to 30 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, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, alkylaryl group having 7 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroarylalkyl group having 2 to 30 carbon atoms, amine group having 0 to 24 carbon atoms, and alkyl aryl group having 0 to 24 carbon atoms. It means being substituted with one or more substituents selected from the group consisting of a silyl group, an aryloxy group having 6 to 30 carbon atoms, and an aliphatic aromatic mixed ring group having 3 to 30 carbon atoms. Effects of the invention

[0036] When a novel anthracene compound according to the present invention is used as a host material in an organic light-emitting diode, an organic light-emitting diode can be provided that exhibits long lifespan characteristics and improved efficiency compared to an organic light-emitting diode according to the prior art. Brief explanation of the drawing

[0037] Figure 1 is a figure illustrating the structure of an organic light-emitting diode according to an embodiment of the present invention. Specific details for implementing the invention

[0038] Hereinafter, preferred embodiments that enable a person skilled in the art to easily implement the present invention will be described in detail with reference to the attached drawings.

[0039] In each drawing of the present invention, the sizes or dimensions of the structures are depicted enlarged or reduced compared to the actual size to ensure clarity of the invention, and known configurations are omitted to reveal characteristic configurations; therefore, the invention is not limited to the drawings. In describing the principles of a preferred embodiment of the present invention in detail, if it is determined that a specific description of related known functions or configurations could unnecessarily obscure the essence of the invention, such detailed description is omitted.

[0040] Furthermore, the size and thickness of each component shown in the drawings are depicted arbitrarily for convenience of explanation, and thus the present invention is not necessarily limited to what is illustrated. Additionally, thicknesses have been enlarged in the drawings to clearly represent various layers and regions. Moreover, in the drawings, the thickness of some layers and regions has been exaggerated for convenience of explanation. When a part such as a layer, film, region, or plate is described as being "on" another part, this includes not only cases where it is "immediately on" another part, but also cases where there is another part in between.

[0041] Furthermore, throughout the specification, when a part is described as "including" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components. Also, throughout the specification, the term "on" means being located above or below the subject part, and does not necessarily mean being located on the upper side with respect to the direction of gravity.

[0042] The present invention provides an organic light-emitting device that can be used in the light-emitting layer of an organic light-emitting device to improve the long-life characteristics of the organic light-emitting device, and comprises an anthracene compound having a specific structure and containing deuterium as a host, and also comprises a boron compound having a specific structure as a dopant.

[0043] To explain this in more detail, the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises a light-emitting layer comprising a host and a dopant, the host comprises at least one of anthracene compounds represented by [Chemical Formula A], and the dopant comprises at least one of compounds represented by [Chemical Formula B-1] or [Chemical Formula B-2].

[0044] [Chemical Formula A] [Structural Formula 1]

[0045]

[0046] In the above [Chemical Formula A],

[0047] The above A is any one selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, and

[0048] The above R1 is hydrogen or deuterium, and

[0049] The above R, R2 to R 12The are identical or different from one another and each independently 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 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 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 50 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 6 to 50 carbon atoms. Any one selected from an arylthioxy group, a substituted or unsubstituted amine group having 0 to 30 carbon atoms, a substituted or unsubstituted silyl group having 0 to 30 carbon atoms, a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, a cyano group, a nitro group, and a halogen group, and each of these can be connected to adjacent substituents to additionally form an aliphatic or aromatic single or polycyclic ring and an aliphatic aromatic mixed ring.

[0050] The above n is an integer from 1 to 8, wherein if n is 2 or greater, each R is the same or different from each other, and

[0051] In the above structural formula 1, the above R5 to R 12 One of them is a single bond bonded to an aromatic carbon atom in the anthracene of the above chemical formula A, and

[0052] However, at least one substituent in [Formula A] above is substituted with deuterium or is a substituent containing deuterium.

[0053] [Chemical Formula B-1] [Chemical Formula B-2]

[0054]

[0055] In the above [Chemical Formula B-1] and [Chemical Formula B-2],

[0056] The above A1 to A3 are identical or different from one another and are each independently selected from an aromatic hydrocarbon ring having 6 to 50 carbon atoms that is substituted or unsubstituted, an aromatic heterocycle having 2 to 50 carbon atoms that is substituted or unsubstituted, an aliphatic ring having 3 to 30 carbon atoms that is substituted or unsubstituted, and an aliphatic-aromatic mixed ring having 3 to 30 carbon atoms that is substituted or unsubstituted, and each substituent within the A1 to A3 rings may be connected to adjacent substituents to additionally form a monocyclic or polycyclic ring of an aliphatic or aromatic group.

[0057] The above Y1 and Y2 are identical or different from each other, and each independently, NR 21 , CR 22 R 23 , O, S, Se and SiR 24 R 25 It is one of the selected from among, and

[0058] The above R 21 to R 25 The groups are identical or different from each other, and each independently includes hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, Any one selected from a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C30 alkylthioxy group, a substituted or unsubstituted C6 to C30 arylthioxy group, a substituted or unsubstituted C0 to C30 amine group, a substituted or unsubstituted C0 to C30 silyl group, a substituted or unsubstituted C3 to C30 aliphatic aromatic mixed ring, a nitro group, a cyano group, and a halogen group, and

[0059] The above R 21 to R 25 Each can additionally form a monocyclic or polycyclic ring of alicyclic or aromatic by combining with one or more rings selected from the above A1 to A3 rings, and

[0060] The above R 22 and R 23 , R 24 and R 25 Each of these can be connected to each other to additionally form alicyclic or aromatic single or polycyclic rings, and

[0061] The term 'substituted' in 'substituted or unsubstituted' within [Chemical Formula A], [Chemical Formula B-1], and [Chemical Formula B-2] above refers to deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, cycloalkyl group having 3 to 30 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, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, alkylaryl group having 7 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroarylalkyl group having 2 to 30 carbon atoms, amine group having 0 to 24 carbon atoms, and alkyl aryl group having 0 to 24 carbon atoms. It means being substituted with one or more substituents selected from the group consisting of a silyl group, an aryloxy group having 6 to 30 carbon atoms, and an aliphatic aromatic mixed ring group having 3 to 30 carbon atoms.

[0062] Meanwhile, considering the range of the alkyl group or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms" and "substituted or unsubstituted aryl group having 5 to 50 carbon atoms" in the present invention, the range of the number of carbon atoms of the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms refers to the total number of carbon atoms constituting the alkyl portion or aryl portion when viewed as unsubstituted without considering the portion where the substituent is substituted. For example, a phenyl group substituted with a butyl group at the para position should be considered as corresponding to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

[0063] The aryl group, which is a substituent used in the compound of the present invention, is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and when the aryl group is a substituent, it can fuse with neighboring substituents to additionally form a ring.

[0064] Specific examples of the above aryl group include aromatic groups such as 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, chrysenyl, naphthacenyl, fluoranthenyl, etc., and one or more hydrogen atoms of the above aryl group may be deuterium atoms, halogen atoms, hydroxyl groups, nitro groups, cyano groups, silyl groups, amino groups (-NH2, -NH(R), -N(R')(R''), where R' and R" are independently alkyl groups having 1 to 10 carbon atoms, in this case referred to as "alkylamino groups"), amido groups, hydrazine groups, hydrazone groups, carboxyl groups, sulfonic acid groups, phosphate groups, etc. It may be substituted with 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.

[0065] The heteroaryl group, which is a substituent used in the compound of the present invention, refers to a cyclic aromatic system having 2 to 24 carbon atoms, comprising 1, 2, or 3 heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te, with the remaining ring atom being carbon, and said rings can be fused to form a ring. And one or more hydrogen atoms of said heteroaryl group can be substituted with a substituent similar to that of said aryl group.

[0066] In addition, in the present invention, the aromatic heteroring refers to a ring in which one or more aromatic carbons in an aromatic hydrocarbon ring are substituted with heteroatoms, and the aromatic heteroring preferably has 1 to 3 aromatic carbons in the aromatic hydrocarbon substituted with one or more heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te.

[0067] The alkyl group used as a substituent in the present invention is a substituent from which one hydrogen is removed from an alkane, and has a structure including a straight chain or a branched form. Specific examples thereof include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, etc., and one or more hydrogen atoms of the alkyl group can be replaced with substituents similar to those in the case of the aryl group.

[0068] In the cycloalkyl group, which is a substituent used in the compound of the present invention, 'cyclo' refers to a substituent having a structure capable of forming a single ring or multiple rings of saturated hydrocarbons within the alkyl group. Specific examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, dicyclopentadienyl, decahydronaphthyl, norbornyl, bornyl, isobornyl, etc., and one or more hydrogen atoms of the cycloalkyl group can be substituted with substituents similar to those in the case of the aryl group.

[0069] The alkoxy group, which is a substituent used in the compound of the present invention, is a substituent in which an oxygen atom is bonded to the terminal of an alkyl group or a cycloalkyl group, and specific examples thereof include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, cyclobutyloxy, cyclopentyloxy, adamantanoxy, dicyclopentanoxy, bornoxy, isobornyloxy, etc., and one or more hydrogen atoms of the alkoxy group can be substituted with a substituent similar to that of the aryl group.

[0070] Specific examples of arylalkyl groups used as substituents in the compound of the present invention include phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl naphthylethyl, etc., and one or more hydrogen atoms of the arylalkyl groups can be substituted with substituents similar to those of the aryl groups.

[0071] In addition, in the present invention, the alkenyl group refers to an alkyl substituent comprising a single carbon-carbon double bond formed by two carbon atoms, and the alkynyl group refers to an alkyl substituent comprising a single carbon-carbon triple bond formed by two carbon atoms.

[0072] In addition, the alkylene group used in the present invention is an organic radical induced by the removal of two hydrogens from an alkane molecule, which is a saturated hydrocarbon in a straight-chain or branched form. Specific examples of the alkylene group include methylene, ethylene, propylene, isopropylene, isobutylene, sec-butylene, tert-butylene, pentylene, iso-amylene, hexylene, etc., and one or more hydrogen atoms of the alkylene group can be replaced with substituents similar to those in the case of the aryl group.

[0073] In addition, the aliphatic aromatic mixed ring or aliphatic aromatic mixed ring used in the present invention refers to a ring in which two or more rings are condensed together and the entire molecule has non-aromacity, and in addition to C, the polycyclic aliphatic aromatic mixed ring may include a heteroatom selected from N, O, P, and S.

[0074] In addition, in the present invention, the amine group may include -NH2, alkylamine group, arylamine group, alkylarylamine group, arylheteroarylamine group, heteroarylamine group, etc., wherein the arylamine group refers to an amine in which one or two hydrogens are substituted with an aryl group in the -NH2; the alkylamine group refers to an amine in which one or two hydrogens are substituted with an alkyl group in the -NH2; the alkylarylamine group refers to an amine in which one hydrogen is substituted with an alkyl group and the other hydrogen is substituted with an aryl group in the -NH2; the arylheteroarylamine group refers to an amine in which one hydrogen is substituted with an aryl group and the other hydrogen is substituted with a heteroaryl group in the -NH2; and the heteroarylamine group refers to an amine in which one or two hydrogens are substituted with a heteroaryl group in the -NH2. Examples of the arylamine group include a substituted or unsubstituted monoarylamine group and a substituted or unsubstituted diarylamine group. There are, and the same applies to the above alkylamine group and heteroarylamine group.

[0075] Here, each aryl group in the arylamine group, heteroarylamine group, and arylheteroarylamine group may be a monocyclic aryl group or a polycyclic aryl group, and each heteroaryl group in the arylamine group, heteroarylamine group, and arylheteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

[0076] The silyl group, which is a substituent used in the compound of the present invention, may include -SiH3, alkylsilyl group, arylsilyl group, alkylarylsilyl group, arylheteroarylsilyl group, heteroarylsilyl group, etc., wherein the arylsilyl group refers to a silyl group in which one, two, or three hydrogens are substituted with an aryl group in -SiH3, the alkylsilyl group refers to an amine in which one, two, or three hydrogens are substituted with an alkyl group in SiH3, the alkylarylsilyl group refers to a silyl group in which at least one hydrogen in each of -SiH3 is substituted with an alkyl group and an aryl group, comprising one or two alkyl groups and two or one corresponding aryl groups, and the arylheteroarylsilyl group refers to a silyl group in which at least one hydrogen in each of -SiH3 is substituted with an aryl group and a heteroaryl group, comprising one or two aryl groups and two or one corresponding heteroaryl groups. Meaning,

[0077] A heteroarylsilyl group in -SiH3 refers to a silyl group in which one, two, or three hydrogens are substituted with a heteroaryl group. Examples of the arylsilyl group include a substituted or unsubstituted monoarylsilyl group, a substituted or unsubstituted diarylsilyl group, or a substituted or unsubstituted triarylsilyl group, and the same applies to the alkylsilyl group and the heteroarylsilyl group.

[0078] Here, each aryl group in the arylsilyl group, heteroarylsilyl group, and arylheteroarylsilyl group may be a monocyclic aryl group or a polycyclic aryl group, and each heteroaryl group in the arylsilyl group, heteroarylsilyl group, and arylheteroarylsilyl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

[0079] In addition, specific examples of the above silyl groups include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc., and one or more hydrogen atoms of the above silyl groups can be substituted with substituents similar to those of the above aryl groups.

[0080] Meanwhile, as a more preferred example of 'substitution' in 'substituted or unsubstituted' in [Chemical Formula A], [Chemical Formula B-1], and [Chemical Formula B-2], this includes deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 12 carbon atoms, halogenated alkyl group having 1 to 12 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms, alkenyl group having 2 to 12 carbon atoms, alkynyl group having 2 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, It may be substituted with one or more substituents selected from the group consisting of an alkylamino group having 1 to 12 carbon atoms, an amine group having 0 to 18 carbon atoms, a silyl group having 0 to 18 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, and an aliphatic-aromatic mixed ring group having 3 to 18 carbon atoms.

[0081] Here, the anthracene compound represented by [Chemical Formula A], used as a host material in an organic light-emitting diode according to the present invention, has a structural feature in which a phenyl group comprising A and R1 to R4 is connected at the 10th position of the anthracene ring, wherein R1 is hydrogen or deuterium and A is selected from any one of a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, and furthermore, R5 to R4 in Structural Formula 1 12 One of them is a single bond bonded to the aromatic carbon atom at position 9 in the anthracene ring, R5 to R 12 Diben containing article The technical features include the fact that the furan structure is connected to the anthracene ring by a single bond, and also that at least one substituent in chemical formula A is substituted with deuterium or is a substituent containing deuterium.

[0082] [Chemical Formula A] [Structural Formula 1]

[0083]

[0084] As a preferred embodiment of the present invention, in [Chemical Formula A], A may be a deuterium-substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0085] In addition, as a preferred embodiment, in the above [Chemical Formula A], A may be any one selected from a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a deuterium-substituted or unsubstituted terphenyl group, a deuterium-substituted or unsubstituted naphthyl group, or a deuterium-substituted or unsubstituted phenanthryl group.

[0086] In addition, as a preferred embodiment, at least one of the Rs in [Chemical Formula A] may be deuterium, preferably two or more may be deuterium, more preferably four or more may be deuterium, and even more preferably all eight may be deuterium.

[0087] In addition, as a preferred embodiment, at least one of R2 to R4 in [Chemical Formula A] may be selected from hydrogen, deuterium, and substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and more preferably, each of R2 to R4 may be the same or different from each other and may each be independently selected from deuterium and substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0088] Also, as a preferred embodiment, in the above [Chemical Formula A], R5 to R 12 At least one of the above non-single bond substituents may be a deuterium-substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0089] In addition, as a preferred embodiment, the degree of deuteration of the anthracene compound represented by [Chemical Formula A] may preferably be 20% or more, more preferably 30% or more, more preferably 35% or more, more preferably 40% or more, more preferably 45% or more, more preferably 50% or more, more preferably 55% or more, more preferably 60% or more, more preferably 65% ​​or more, more preferably 70% or more, more preferably 75% or more, and more preferably 80% or more.

[0090] Meanwhile, regarding the degree of deuteration used in this specification, specifically, a "deuterated derivative" of compound X generally means having the same structure as compound X but accompanied by at least one deuterium (D) that replaces a hydrogen atom (H) bonded to a carbon atom, nitrogen atom, or oxygen atom in compound X.

[0091] In this case, the term "yy % deuteriumized" or "yy % deuteriumized" refers to the ratio of deuterium to the sum of all hydrogen and deuterium directly bonded to carbon, nitrogen, or oxygen atoms in compound X, expressed as a percentage.

[0092] Therefore, if 2 of the 6 hydrogens of benzene are deuterated, the degree of deuteration in the compound C6H4D2 can be considered as 2 / (4+2) × 100 = 33% deuteration.

[0093] In the case where deuterium is substituted in an anthracene compound in the present invention, the degree of deuteration thereof refers to the ratio of all deuterium directly bonded to carbon atoms in the anthracene compound to the sum of all hydrogens directly bonded to carbon atoms in the anthracene compound and all deuterium directly bonded to carbon atoms in the anthracene compound, expressed as a percentage.

[0094] For example, in the case of an anthracene compound represented by the following compound 1, there are 5 deuterium atoms in the phenyl group bonded to the anthracene group, 4 hydrogen atoms in the phenyl group bonded to the anthracene group, 8 hydrogen atoms in the anthracene group, and 7 hydrogen atoms bonded to each aromatic carbon atom in the 6-membered ring of dibenzofuran, so its degree of deuteration can be expressed as 100 * 5 / (5 + 19) = 20.8%.

[0095] [Compound 1]

[0096] On the other hand, in the case of specific substituents, since the degree of deuteration may vary for each individual substituent, the degree of deuteration can be expressed by calculating the average degree of substitution.

[0097] As an example, let us consider the case of an anthracene group partially substituted with deuterium. Depending on the reaction conditions, an anthracene compound in which deuterium is bonded to all carbon atoms can be prepared and used as a deuterium-substituted anthracene group. However, depending on the reaction conditions, a product may be obtained in which a compound in which hydrogen is bonded to carbon atoms at specific positions or parts (moiety) and a compound in which deuterium is bonded exist in a mixed form. Since it can be very difficult to separate these, in this case, the average degree of deuterium substitution can be determined and referenced to calculate the degree of deuteration based on the overall structural formula.

[0098] In the present invention, when an anthracene compound represented by [Chemical Formula A] is used as a host material in the light-emitting layer of an organic light-emitting device, the lifespan of the organic light-emitting device can be further improved.

[0099] More specifically, the anthracene compound represented by [Chemical Formula A] above may be any one of the compounds selected from the group represented by <Compound 1> to <Compound 60> below, but is not limited thereto.

[0100]

[0101] [Compound 1] [Compound 2] [Compound 3] [Compound 4]

[0102]

[0103] [Compound 5] [Compound 6] [Compound 7] [Compound 8]

[0104]

[0105] [Compound 9] [Compound 10] [Compound 11] [Compound 12]

[0106]

[0107] [Compound 13] [Compound 14] [Compound 15] [Compound 16]

[0108]

[0109] [Compound 17] [Compound 18] [Compound 19] [Compound 20]

[0110]

[0111] [Compound 21] [Compound 22] [Compound 23] [Compound 24]

[0112]

[0113] [Compound 25] [Compound 26] [Compound 27] [Compound 28]

[0114]

[0115] [Compound 29] [Compound 30] [Compound 31] [Compound 32]

[0116]

[0117] [Compound 33] [Compound 34] [Compound 35] [Compound 36]

[0118]

[0119] [Compound 37] [Compound 38] [Compound 39] [Compound 40]

[0120]

[0121] [Compound 41] [Compound 42] [Compound 43] [Compound 44]

[0122]

[0123] [Compound 45] [Compound 46] [Compound 47] [Compound 48]

[0124]

[0125] [Compound 49] [Compound 50] [Compound 51] [Compound 52]

[0126]

[0127] [Compound 53] [Compound 54] [Compound 55] [Compound 56]

[0128]

[0129] [Compound 57] [Compound 58] [Compound 59] [Compound 60]

[0130] In addition, the boron compound represented by [Chemical Formula B-1] or [Chemical Formula B-2], which is used as a dopant material in an organic light-emitting diode according to the present invention,

[0131] A2 and A3 rings, which are selected from among a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aromatic heteroring having 2 to 50 carbon atoms, a substituted or unsubstituted aliphatic ring having 3 to 30 carbon atoms, and a substituted or unsubstituted aliphatic aromatic mixed ring having 3 to 30 carbon atoms, are each directly connected to a boron atom (B), wherein the A2 and A3 rings are connected to each other by a linker Y2, and the A3 ring is connected by a linker Y1, wherein the linker Y1 is connected to a vinyl group connected to a sulfur atom (S) and a boron atom (B), and the sulfur atom (S) is bonded to the A1 ring to form a pentagonal ring containing the sulfur atom (S).

[0132] [Chemical Formula B-1] [Chemical Formula B-2]

[0133]

[0134] In a preferred embodiment, the above A1 to A3 in the compound represented by [Chemical Formula B-1] or [Chemical Formula B-2] each other Identical or different, Each It may be an independently substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, and specifically, it may be any one ring selected from a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, an indene ring, a fluorene ring, a pyrene ring, a perylene ring, a chrysene ring, a naphthacene ring, a fluoranthen ring, an acenaphthylene ring, and a pentacene ring.

[0135] In this case, the aromatic hydrocarbon rings of A1 and A2 in [Chemical Formula B-1] may be any one selected from [Structural Formula 10] to [Structural Formula 21] below, and the aromatic hydrocarbon rings of A1 and A2 in [Chemical Formula B-2] may be identical or different and independently selected from [Structural Formula 10] to [Structural Formula 21] below.

[0136] [Structural Formula 10] [Structural Formula 11] [Structural Formula 12]

[0137]

[0138] [Structural Formula 13] [Structural Formula 14] [Structural Formula 15]

[0139]

[0140] [Structural Formula 16] [Structural Formula 17] [Structural Formula 18]

[0141]

[0142] [Structural Formula 19] [Structural Formula 20] [Structural Formula 21]

[0143]

[0144] In the above [Structural Formula 10] to [Structural Formula 21], "-*" indicates that the carbon within the aromatic ring of the above A1 ring is a sulfur atom (S). or means a bonding site for bonding with a carbon atom within a pentagonal ring containing a sulfur atom (S), or

[0145] Or, it refers to a bonding site for a carbon within the aromatic ring in the above A2 ring to bond with a boron atom (B) or linker Y2, and

[0146] In the above [Structural Formula 10] to [Structural Formula 21], R is each the same 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 5 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 30 carbon atoms, a substituted or unsubstituted silyl group having 0 to 30 carbon atoms, a cyano group, and a halogen group.

[0147] The above m is an integer from 1 to 8, and if m is 2 or greater, or if R is 2 or greater, each R may be the same or different from each other.

[0148] In addition, when the above A1 to A3 rings are identical or different from each other and are each independently substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms, the aromatic hydrocarbon ring of A3 in [Chemical Formula B-1] and [Chemical Formula B-2] may be a ring represented by the following [Structural Formula B].

[0149] [Structural Formula B]

[0150]

[0151] In the above [Structural Formula B], "-*" represents the carbon within the aromatic ring in the A3 ring, linker Y1, boron atom (B), and linker Y 2 It refers to a combination site for combining with each other.

[0152] In the above [Structural Formula B], the above R 55 to R 57The groups are identical 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 alkenyl group having 2 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 5 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 30 carbon atoms, a substituted or unsubstituted silyl group having 0 to 30 carbon atoms, a cyano group, and a halogen group.

[0153] The above R 55 to R 57 Each can be connected to adjacent substituents to additionally form a cycloaliphatic or aromatic single or polycyclic rings.

[0154] Also, as a preferred embodiment, at least one of Y1 and Y2 in the compound represented by [Chemical Formula B-1] and [Chemical Formula B-2] is NR 21 It may be, and preferably, Y1 and Y2 in the compounds represented by [Chemical Formula B-1] and [Chemical Formula B-2] are identical or different from each other, and each independently NR 21 It can be, where, the above R 21 It is the same as previously defined.

[0155] In addition, the connectors Y1 and Y2 in the above [Chemical Formula B-1] and [Chemical Formula B-2] are NR 21 In the case where, preferably, the substituent R 21The silver may be a substituted or unsubstituted aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and more preferably, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0156] In addition, as an embodiment, at least one of the connectors Y1 and Y2 in [Chemical Formula B-1] and [Chemical Formula B-2] may be identical or different from each other and may be a connector represented by the following [Structural Formula A].

[0157] [Structural Formula A]

[0158]

[0159] In the above [Structural Formula A], "-*" represents a carbon atom connected to Y1 within a pentagonal ring containing a sulfur atom (S), or a carbon atom connected to said sulfur atom (S), or an aromatic carbon atom within the A2 ring. Or it refers to a bonding site for bonding with an aromatic carbon atom within the A3 ring, respectively,

[0160] Here, in the above [Structural Formula A], the above R 41 to R 45 The groups are identical 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 alkenyl group having 2 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 5 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 30 carbon atoms, a substituted or unsubstituted silyl group having 0 to 30 carbon atoms, a nitro group, a cyano group, and a halogen group, and the above R 41 and R45 Each of the above A2 ring or A3 ring can additionally form a monocyclic or polycyclic ring of alicyclic or aromatic type.

[0161] In addition, at least one of the A1 to A3 rings in [Chemical Formula B-1] and [Chemical Formula B-2] may have an aryl amino group represented by the following structural formula F bonded to an aromatic hydrocarbon ring having 6 to 50 carbon atoms, or an aromatic heteroring having 2 to 50 carbon atoms.

[0162] [Structural Formula F]

[0163]

[0164] In the above [structural formula F], "-*" represents a bonding site for bonding to an aromatic carbon of one or more of the rings A1 to A3, and

[0165] Above Ar 11 and Ar 12 The groups are identical or different, and independently substituted or unsubstituted aryl groups having 6 to 12 carbon atoms or heteroaryl groups having 3 to 18 carbon atoms, and each of these can be connected to form a ring.

[0166] In addition, the boron compounds represented by [Chemical Formula B-1] and [Chemical Formula B-2] above may be any one of the compounds selected from [Chemical Formula 1] to [Chemical Formula 84] below.

[0167]

[0168] [Chemical Formula 1] [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4]

[0169]

[0170] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8]

[0171]

[0172] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12]

[0173]

[0174] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16]

[0175]

[0176] [Chemical Formula 17] [Chemical Formula 18] [Chemical Formula 19] [Chemical Formula 20]

[0177]

[0178] [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24]

[0179]

[0180] [Chemical Formula 25] [Chemical Formula 26] [Chemical Formula 27] [Chemical Formula 28]

[0181]

[0182] [Chemical Formula 29] [Chemical Formula 30] [Chemical Formula 31] [Chemical Formula 32]

[0183]

[0184] [Chemical Formula 33] [Chemical Formula 34] [Chemical Formula 35] [Chemical Formula 36]

[0185]

[0186] [Chemical Formula 37] [Chemical Formula 38] [Chemical Formula 39] [Chemical Formula 40]

[0187]

[0188] [Chemical Formula 41] [Chemical Formula 42] [Chemical Formula 43] [Chemical Formula 44]

[0189]

[0190] [Chemical Formula 45] [Chemical Formula 46] [Chemical Formula 47] [Chemical Formula 48]

[0191]

[0192] [Chemical Formula 49] [Chemical Formula 50] [Chemical Formula 51] [Chemical Formula 52]

[0193]

[0194] [Chemical Formula 53] [Chemical Formula 54] [Chemical Formula 55] [Chemical Formula 56]

[0195]

[0196] [Chemical Formula 57] [Chemical Formula 58] [Chemical Formula 59] [Chemical Formula 60]

[0197]

[0198] [Chemical Formula 61] [Chemical Formula 62] [Chemical Formula 63] [Chemical Formula 64]

[0199]

[0200] [Chemical Formula 65] [Chemical Formula 66] [Chemical Formula 67] [Chemical Formula 68]

[0201]

[0202] [Chemical Formula 69] [Chemical Formula 70] [Chemical Formula 71] [Chemical Formula 72]

[0203]

[0204] [Chemical Formula 73] [Chemical Formula 74] [Chemical Formula 75] [Chemical Formula 76]

[0205]

[0206] [Chemical Formula 77] [Chemical Formula 78] [Chemical Formula 79] [Chemical Formula 80]

[0207]

[0208] [Chemical Formula 81] [Chemical Formula 82] [Chemical Formula 83] [Chemical Formula 84]

[0209] The organic layer in the organic light-emitting device according to the present invention may additionally include at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function simultaneously, an electron transport layer, and an electron injection layer in addition to the light-emitting layer.

[0210] FIG. 1 is a figure illustrating the structure of an organic light-emitting diode according to the present invention.

[0211] As shown in FIG. 1 above, an organic light-emitting device according to an embodiment of the present invention comprises an anode (20), a hole transport layer (40), a light-emitting layer (50), an electron transport layer (60), and a cathode (80), and may further include a hole injection layer (30) and an electron injection layer (70) as needed, and may also form an intermediate layer of one or two layers.

[0212] Here, the anthracene compound represented by [Chemical Formula A] above can be used as a host in the light-emitting layer.

[0213] Referring to FIG. 1, the organic light-emitting device of the present invention and the method for manufacturing the same are as follows. First, an anode (20) is formed by coating a material for an anode electrode on a substrate (10). Here, the substrate (10) is a substrate used in conventional organic EL devices, and an organic substrate or a transparent plastic substrate with excellent transparency, surface smoothness, ease of handling, and water resistance is preferred. In addition, the anode electrode material is a transparent and highly conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO).

[0214] A hole injection layer (30) is formed on the upper surface of the anode (20) by vacuum thermal deposition or spin coating of a hole injection layer material. Next, a hole transport layer (40) is formed on the upper surface of the hole injection layer (30) by vacuum thermal deposition or spin coating of a hole transport layer material.

[0215] The above hole injection layer material may be used without particular limitation as long as it is commonly used in the art, for example, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine], NPD [N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD [N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine], DNTPD [N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine], HAT-CN [Dipyrazino[2,3-f :2',3'-h ]quinoxaline-2,3,6,7,10,11-hexacarbonitrile], etc. However, the present invention is not necessarily limited thereto. It is not.

[0216] In addition, the material of the hole transport layer is not particularly limited as long as it is commonly used in the art, for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine (a-NPD) may be used. However, the present invention is not necessarily limited thereto.

[0217] Next, a light-emitting layer (50) composed of a host and a dopant is deposited on top of the hole transport layer (40) by a vacuum deposition method or a spin coating method, and the thickness of the light-emitting layer is preferably 50 to 2,000 Å. Optionally, an electron density control layer (not shown) may be additionally formed on top of the organic light-emitting layer (50).

[0218] Here, the light-emitting layer may be composed of a host and a dopant, and the materials constituting them are as described above. Here, the content of the dopant can typically be selected in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

[0219] In addition, the host in the light-emitting layer used in the present invention may use an anthracene compound represented by the chemical formula A alone, may be used in combination with a known host, or may be used laminated separately from a known host.

[0220] In one embodiment, the host in the light-emitting layer may be used by mixing one or more host compounds other than the anthracene compound represented by [Chemical Formula A], or one or more host compounds other than the anthracene compound represented by [Chemical Formula A] may be used by stacking them separately from the layer represented by [Chemical Formula A] within the light-emitting layer.

[0221] At this time, as an example of a known host that can be used when mixed with or separately laminated with a known host as the above host, one or more compounds selected from the compounds represented by [Chemical Formula B] and [Chemical Formula C] below may be used.

[0222] [Chemical Formula B]

[0223]

[0224] In the above [Chemical Formula B],

[0225] The above X1 to X 10are identical or different from one another and each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C1 to C30 alkylthioxy group, a substituted or unsubstituted C5 to C30 arylthioxy group, a substituted or unsubstituted C0 to C30 amine group, a substituted or unsubstituted C5 to C50 aryl group, a substituted or unsubstituted C5 to C50 heteroaryl group having O, N or S as a heteroatom, a substituted or unsubstituted Any one selected from the group consisting of silicon groups, substituted or unsubstituted boron groups, substituted or unsubstituted carbon 0 to 30 silyl groups, carbonyl groups, phosphoryl groups, amino groups, nitrile groups, hydroxyl groups, nitro groups, halogen groups, amide groups, and ester groups, and adjacent groups can form an aliphatic, aromatic, aliphatic hetero, or aromatic hetero condensed ring.

[0226] More specifically, the host compound represented by the above chemical formula B may be represented by any one selected from the group represented by [Chemical Formula 101] to [Chemical Formula 296] below, but is not limited thereto.

[0227] [Chemical Formula 101] [Chemical Formula 102] [Chemical Formula 103] [Chemical Formula 104]

[0228]

[0229] [Chemical Formula 105] [Chemical Formula 106] [Chemical Formula 107] [Chemical Formula 108]

[0230]

[0231] [Chemical Formula 109] [Chemical Formula 110] [Chemical Formula 111] [Chemical Formula 112]

[0232]

[0233] [Chemical Formula 113] [Chemical Formula 114] [Chemical Formula 115] [Chemical Formula 116]

[0234]

[0235] [Chemical Formula 117] [Chemical Formula 118] [Chemical Formula 119] [Chemical Formula 120]

[0236]

[0237] [Chemical Formula 121] [Chemical Formula 122] [Chemical Formula 123] [Chemical Formula 124]

[0238]

[0239] [Chemical Formula 125] [Chemical Formula 126] [Chemical Formula 127] [Chemical Formula 128]

[0240]

[0241] [Chemical Formula 129] [Chemical Formula 130] [Chemical Formula 131] [Chemical Formula 132]

[0242]

[0243] [Chemical Formula 133] [Chemical Formula 134] [Chemical Formula 135] [Chemical Formula 136]

[0244]

[0245] [Chemical Formula 137] [Chemical Formula 138] [Chemical Formula 139] [Chemical Formula 140]

[0246]

[0247] [Chemical Formula 141] [Chemical Formula 142] [Chemical Formula 143] [Chemical Formula 144]

[0248]

[0249] [Chemical Formula 145] [Chemical Formula 146] [Chemical Formula 147] [Chemical Formula 148]

[0250]

[0251] [Chemical Formula 149] [Chemical Formula 150] [Chemical Formula 151] [Chemical Formula 152]

[0252]

[0253] [Chemical Formula 153] [Chemical Formula 154] [Chemical Formula 155] [Chemical Formula 156]

[0254]

[0255] [Chemical Formula 157] [Chemical Formula 158] [Chemical Formula 159] [Chemical Formula 160]

[0256]

[0257] [Chemical Formula 161] [Chemical Formula 162] [Chemical Formula 163] [Chemical Formula 164]

[0258]

[0259] [Chemical Formula 165] [Chemical Formula 166] [Chemical Formula 167] [Chemical Formula 168]

[0260]

[0261] [Chemical Formula 169] [Chemical Formula 170] [Chemical Formula 171] [Chemical Formula 172]

[0262]

[0263] [Chemical Formula 173] [Chemical Formula 174] [Chemical Formula 175] [Chemical Formula 176]

[0264]

[0265] [Chemical Formula 177] [Chemical Formula 178] [Chemical Formula 179] [Chemical Formula 180]

[0266]

[0267] [Chemical Formula 181] [Chemical Formula 182] [Chemical Formula 183] [Chemical Formula 184]

[0268]

[0269] [Chemical Formula 185] [Chemical Formula 186] [Chemical Formula 187] [Chemical Formula 188]

[0270]

[0271] [Chemical Formula 189] [Chemical Formula 190] [Chemical Formula 191] [Chemical Formula 192]

[0272]

[0273] [Chemical Formula 193] [Chemical Formula 194] [Chemical Formula 195] [Chemical Formula 196]

[0274]

[0275] [Chemical Formula 197] [Chemical Formula 198] [Chemical Formula 199] [Chemical Formula 200]

[0276]

[0277] [Chemical Formula 201] [Chemical Formula 202] [Chemical Formula 203] [Chemical Formula 204]

[0278]

[0279] [Chemical Formula 205] [Chemical Formula 206] [Chemical Formula 207] [Chemical Formula 208]

[0280]

[0281] [Chemical Formula 209] [Chemical Formula 210] [Chemical Formula 211] [Chemical Formula 212]

[0282]

[0283] [Chemical Formula 213] [Chemical Formula 214] [Chemical Formula 215] [Chemical Formula 216]

[0284]

[0285] [Chemical Formula 217] [Chemical Formula 218] [Chemical Formula 219] [Chemical Formula 220]

[0286]

[0287] [Chemical Formula 221] [Chemical Formula 222] [Chemical Formula 223] [Chemical Formula 224]

[0288]

[0289] [Chemical Formula 225] [Chemical Formula 226] [Chemical Formula 227] [Chemical Formula 228]

[0290]

[0291] [Chemical Formula 229] [Chemical Formula 230] [Chemical Formula 231] [Chemical Formula 232]

[0292]

[0293] [Chemical Formula 233] [Chemical Formula 234] [Chemical Formula 235] [Chemical Formula 236]

[0294]

[0295] [Chemical Formula 237] [Chemical Formula 238] [Chemical Formula 239] [Chemical Formula 240]

[0296]

[0297] [Chemical Formula 241] [Chemical Formula 242] [Chemical Formula 243] [Chemical Formula 244]

[0298]

[0299] [Chemical Formula 245] [Chemical Formula 246] [Chemical Formula 247] [Chemical Formula 248]

[0300]

[0301] [Chemical Formula 249] [Chemical Formula 250] [Chemical Formula 251] [Chemical Formula 252]

[0302]

[0303] [Chemical Formula 253] [Chemical Formula 254] [Chemical Formula 255] [Chemical Formula 256]

[0304]

[0305] [Chemical Formula 257] [Chemical Formula 258] [Chemical Formula 259] [Chemical Formula 260]

[0306]

[0307] [Chemical Formula 261] [Chemical Formula 262] [Chemical Formula 263] [Chemical Formula 264]

[0308]

[0309] [Chemical Formula 265] [Chemical Formula 266] [Chemical Formula 267] [Chemical Formula 268]

[0310]

[0311] [Chemical Formula 269] [Chemical Formula 270] [Chemical Formula 271] [Chemical Formula 272]

[0312]

[0313] [Chemical Formula 273] [Chemical Formula 274] [Chemical Formula 275] [Chemical Formula 276]

[0314]

[0315] [Chemical Formula 277] [Chemical Formula 278] [Chemical Formula 279] [Chemical Formula 280]

[0316]

[0317] [Chemical Formula 281] [Chemical Formula 282] [Chemical Formula 283] [Chemical Formula 284]

[0318]

[0319] [Chemical Formula 285] [Chemical Formula 286] [Chemical Formula 287] [Chemical Formula 288]

[0320]

[0321] [Chemical Formula 289] [Chemical Formula 290] [Chemical Formula 291] [Chemical Formula 292]

[0322]

[0323] [Chemical Formula 293] [Chemical Formula 294] [Chemical Formula 295] [Chemical Formula 296]

[0324]

[0325] [Chemical Formula C]

[0326]

[0327] In the above [Chemical Formula C],

[0328] The above connector L 21 and L 22 The groups are identical or different from each other and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and

[0329] The above m1 and m2 are each the same or different and are independently integers of 1 or 2, wherein when m1 and m2 are each 2, their respective L 21 and L 22 is identical or different;

[0330] The above Ar 21 and Ar 21 The groups are identical or different from one another and are each independently selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, a substituted or unsubstituted amine group having 0 to 30 carbon atoms, a substituted or unsubstituted silyl group having 0 to 30 carbon atoms, and a substituted or unsubstituted germanium group having 0 to 30 carbon atoms;

[0331] The above Z is any one selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 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 heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, a substituted or unsubstituted amine group having 0 to 30 carbon atoms, a substituted or unsubstituted silyl group having 0 to 30 carbon atoms, a substituted or unsubstituted germanium group having 0 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group;

[0332] The above n1 is an integer from 0 to 8, wherein if each of these is 2 or more, each Z is the same or different from each other, and

[0333] Substituent Z or Ar on the above pyrene ring 21 -(L 21 )m1- or Ar 21 -(L 22 When )m2- is not bonded, hydrogen or deuterium is bonded to the aromatic carbon in the pyrene ring.

[0334] More specifically, the host compound represented by the above chemical formula C may be represented by any one selected from the group represented by [Chemical Formula 301] to [Chemical Formula 372] below, but is not limited thereto.

[0335] [Chemical Formula 301] [Chemical Formula 302] [Chemical Formula 303] [Chemical Formula 304]

[0336]

[0337] [Chemical Formula 305] [Chemical Formula 306] [Chemical Formula 307] [Chemical Formula 308]

[0338]

[0339] [Chemical Formula 309] [Chemical Formula 310] [Chemical Formula 311] [Chemical Formula 312]

[0340]

[0341] [Chemical Formula 313] [Chemical Formula 314] [Chemical Formula 315] [Chemical Formula 316]

[0342]

[0343] [Chemical Formula 317] [Chemical Formula 318] [Chemical Formula 319] [Chemical Formula 320]

[0344]

[0345] [Chemical Formula 321] [Chemical Formula 322] [Chemical Formula 323] [Chemical Formula 324]

[0346]

[0347] [Chemical Formula 325] [Chemical Formula 326] [Chemical Formula 327] [Chemical Formula 328]

[0348]

[0349] [Chemical Formula 329] [Chemical Formula 330] [Chemical Formula 331] [Chemical Formula 332]

[0350]

[0351] [Chemical Formula 333] [Chemical Formula 334] [Chemical Formula 335] [Chemical Formula 336]

[0352]

[0353] [Chemical Formula 337] [Chemical Formula 338] [Chemical Formula 339] [Chemical Formula 340]

[0354]

[0355] [Chemical Formula 341] [Chemical Formula 342] [Chemical Formula 343] [Chemical Formula 344]

[0356]

[0357] [Chemical Formula 345] [Chemical Formula 346] [Chemical Formula 347] [Chemical Formula 348]

[0358]

[0359] [Chemical Formula 349] [Chemical Formula 350] [Chemical Formula 351] [Chemical Formula 352]

[0360]

[0361] [Chemical Formula 353] [Chemical Formula 354] [Chemical Formula 355] [Chemical Formula 356]

[0362]

[0363] [Chemical Formula 357] [Chemical Formula 358] [Chemical Formula 359] [Chemical Formula 360]

[0364]

[0365] [Chemical Formula 361] [Chemical Formula 362] [Chemical Formula 363] [Chemical Formula 364]

[0366]

[0367] [Chemical Formula 365] [Chemical Formula 366] [Chemical Formula 367] [Chemical Formula 368]

[0368]

[0369] [Chemical Formula 369] [Chemical Formula 370] [Chemical Formula 371] [Chemical Formula 372]

[0370]

[0371] Meanwhile, an organic light-emitting device is completed by depositing an electron transport layer (60) on the light-emitting layer using a vacuum deposition method or a spin coating method, forming an electron injection layer (70) on top of it, and forming a cathode electrode (80) by vacuum thermal deposition of a metal for forming a cathode on top of the electron injection layer (70).

[0372] Meanwhile, in the present invention, known electron transport materials may be used as the electron transport layer material to stably transport electrons injected from the cathode. Examples of known electron transport materials include quinoline derivatives, particularly tris(8-quinolinolate)aluminum (Alq3), Liq, TAZ, BAlq, beryllium bis(benzoquinolin-10-olate) (bebq2), compound 201, compound 202, BCP, and oxadiazole derivatives such as PBD, BMD, BND, etc., but are not limited thereto.

[0373]

[0374] TAZ BAlq

[0375]

[0376] <Compound 201> <Compound 202> BCP

[0377]

[0378]

[0379] In addition, the organic light-emitting diode in the present invention may have an electron injection layer (EIL), which is a material having the function of facilitating the injection of electrons from the cathode, laminated on top of the electron transport layer, and this does not particularly limit the material.

[0380] Any material known as an electron injection layer forming material, such as CsF, NaF, LiF, Li2O, BaO, etc., may be used as the electron injection layer forming material. Although the deposition conditions of the electron injection layer vary depending on the compound used, they can generally be selected from a range of conditions nearly identical to those for the formation of the hole injection layer.

[0381] The thickness of the electron injection layer may be about 1 Å to about 100 Å, or about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0382] In addition, in the present invention, the cathode may be formed using a metal for forming a cathode such as lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag), or a transparent cathode using ITO or IZO to obtain a front-emitting device.

[0383] In addition, the organic light-emitting device of the present invention may additionally include a light-emitting layer of a blue light-emitting material, a green light-emitting material, or a red light-emitting material that emits light in a wavelength range of 380 nm to 800 nm. That is, the light-emitting layer of the present invention is a plurality of light-emitting layers, and the blue light-emitting material, the green light-emitting material, or the red light-emitting material in the additionally formed light-emitting layer may be a fluorescent material or a phosphorescent material.

[0384] In addition, at least one layer selected from the hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer in the present invention may be formed by a deposition process or a solution process.

[0385] Here, the deposition process refers to a method of forming a thin film by evaporating a material used as a material for forming each of the layers through heating or the like in a vacuum or low-pressure state, and the solution process refers to a method of forming a thin film by mixing a material used as a material for forming each of the layers with a solvent and using methods such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, etc.

[0386] In addition, the organic light-emitting element in the present invention may be used in any one of the following devices: a flat panel display device; a flexible display device; a device for monochromatic or white flat panel lighting; a device for monochromatic or white flexible lighting; a display device for a vehicle; and a display device for virtual or augmented reality.

[0387] In the following, an organic light-emitting device embodied through examples is described in more detail, but the present invention is not limited to the following examples.

[0388] [Example]

[0389] Synthesis Example 1. Synthesis of [Compound 13]

[0390] Synthesis Example 1-1: Synthesis of 1-a

[0391]

[0392] <1-a>

[0393] 70 g of 2-bromo-1,1'-biphenyl-2',3',4',5',6'-d5 was dissolved in 700 mL of tetrahydrofuran in a 2 L reactor. The temperature was then lowered to -78 °C under a nitrogen atmosphere, and 213 mL of normal butyllithium (1.6 M) was added dropwise. After stirring for 1 hour, 40 g of trimethylborate was added and stirred at room temperature. After the reaction was complete, the mixture was acidified with normal hydrochloric acid, extracted to separate the organic layer, and concentrated under reduced pressure. The substance was recrystallized with tetrahydrofuran to obtain <1-a> (45.2 g, 75%).

[0394] Synthesis Example 1-2: Synthesis of 1-b

[0395]

[0396] <1-a> <1-b>

[0397] 51 g of 9-bromoanthracene, 43 g of <1-a>, 54.8 g of potassium carbonate, 0.9 g of palladium(II) acetate, 3.3 g of SPhos, 210 mL of toluene, 150 mL of ethanol, and 150 mL of distilled water were added to a 1 L reactor and stirred under reflux overnight. After cooling the reaction mixture to room temperature, it was extracted with ethyl acetate and distilled water, and the organic layer was concentrated and separated by column chromatography to obtain <1-b> (55 g, 80%).

[0398] Synthesis Example 1-3: Synthesis of 1-c

[0399]

[0400] <1-b> <1-c>

[0401] 53 g of <1-b> was dissolved in 530 mL of N,N-dimethylformamide in a 2 L round-bottom flask and stirred at room temperature. 30.1 g of N-bromosuccinimide was dissolved in 100 mL of N,N-dimethylformamide and slowly added dropwise to the reaction solution. After confirming the completion of the reaction by thin-layer chromatography, 500 mL of distilled water was added to the reaction solution and stirred; the resulting solid was filtered, and the product was washed with distilled water and methanol. The product was dissolved in toluene, filtered via a silica gel pad, and recrystallized with methanol to obtain <1-c>. (52.0 g, 80%)

[0402] Synthesis Example 1-4: Synthesis of [Compound 13]

[0403]

[0404] <1-c> [Compound 13]

[0405] 25 g of <1-c>, 14.7 g of (dibenzofuran-2-yl)boronic acid, 0.27 g of palladium(II) acetate, 12.51 g of potassium carbonate, and 0.99 g of SPhos were added to a 500 mL reactor. 100 mL of toluene, 75 mL of ethanol, and 75 mL of distilled water were added, and the mixture was refluxed and stirred for 3 hours. After confirming the completion of the reaction by thin-layer chromatography, the temperature was lowered to room temperature, and the resulting solid was filtered. The solid was separated and purified by column chromatography. [Compound 13] was obtained by recrystallization with toluene and acetone. (16.65 g, 55%)

[0406] MS (MALDI-TOF): m / z 501.21 [M + ]

[0407] Synthesis Example 2. Synthesis of [Compound 4]

[0408] Synthesis Example 2-1: Synthesis of 2-a

[0409]

[0410] <1-a> <2-a>

[0411] In Synthesis Examples 1-2 above, <2-a> was obtained in the same manner using 9-bromoanthracene-1,2,3,4,5,6,7,8,10-d9 instead of 9-bromoanthracene. (Yield 79%)

[0412] Synthesis Example 2-2: Synthesis of 2-b

[0413]

[0414] <2-a> <2-b>

[0415] <2-b> was obtained in the same manner as in Synthesis Example 1-3 above, using <2-a> instead of <1-b>. (Yield 76.9%)

[0416] Synthesis Example 2-3: Synthesis of [Compound 4]

[0417]

[0418] <2-b> [Compound 4]

[0419] In Synthesis Examples 1-4 above, [Compound 4] was obtained in the same manner by using <2-b> instead of <1-c> and using dibenzofuran-4-ylboronic acid instead of dibenzofuran-2-ylboronic acid. (Yield 50%)

[0420] MS (MALDI-TOF): m / z 509.26 [M + ]

[0421] Synthesis Example 3. Synthesis of [Compound 7]

[0422] Synthesis Example 3-1: Synthesis of [Compound 7]

[0423]

[0424] [Compound 7]

[0425] [Compound 7] was obtained in the same manner as in Synthesis Examples 2-3 above, using dibenzofuran-2-ylboronic acid instead of dibenzofuran-4-ylboronic acid. (Yield 52%)

[0426] MS (MALDI-TOF): m / z 509.26 [M + ]

[0427] Synthesis Example 4. Synthesis of [Compound 14]

[0428] Synthesis Example 4-1: Synthesis of 4-a

[0429]

[0430] <4-a>

[0431] In Synthesis Examples 1-2 above, <4-a> was obtained in the same manner using 2-biphenylboronic acid instead of <1-a>. (Yield 82%)

[0432] Synthesis Example 4-2: Synthesis of 4-b

[0433]

[0434] <4-a> <4-b>

[0435] In Synthesis Examples 1-3 above, <4-b> was obtained using <4-a> instead of <1-b> in the same manner. (Yield 81.2%)

[0436] Synthesis Example 4-3: Synthesis of 4-c

[0437]

[0438] <4-b> <4-c>

[0439] 35 g of <4-b> and 350 mL of tetrahydrofuran were dissolved in a 1 L round-bottom flask, and the temperature was lowered to -78 ℃ under a nitrogen atmosphere. Then, 60 mL of normal butyllithium (1.6 M) was added dropwise. After stirring for 1 hour, 10.8 g of trimethylborate was added and stirred at room temperature. After the reaction was complete, the mixture was acidified with dinormal hydrochloric acid, extracted to separate the organic layer, and concentrated under reduced pressure. The substance was recrystallized to obtain <4-c> (25 g, 78%).

[0440] Synthesis Example 4-4: Synthesis of 4-d

[0441]

[0442] <4-d>

[0443] 30 g of 3,6-dibromodibenzofuran, 13.4 g of phenyl-d5-boronic acid, 60 g of potassium carbonate, 2.1 g of tetrakis(triphenylphosphine)palladium, 360 mL of toluene, 180 mL of tetrahydrofuran, and 120 mL of distilled water were added to a 1 L round-bottom flask, heated, and refluxed overnight. After confirming the completion of the reaction by thin-layer chromatography, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate and distilled water and concentrated under reduced pressure. The substance was separated and purified by column chromatography, and <4-d> was obtained by recrystallization with dichloromethane and acetone. (19 g, 63%)

[0444] Synthesis Example 4-5: Synthesis of [Compound 14]

[0445]

[0446] <4-c> <4-d> [Compound 14]

[0447] In Synthesis Examples 1-4 above, [Compound 14] was obtained in the same manner by using <4-d> instead of <1-c> and <4-c> instead of dibenzofuran-2-ylboronic acid. (Yield 48%)

[0448] MS (MALDI-TOF): m / z 577.25 [M + ]

[0449] Synthesis Example 5. Synthesis of [Compound 17]

[0450] Synthesis Example 5-1: Synthesis of <5-a>

[0451]

[0452] <5-a>

[0453] 54 g of 2,4-dibromoaniline, 65.6 g of phenyl-d5-boronic acid, 89.2 g of potassium carbonate, 9.9 g of tetrakis(triphenylphosphine)palladium, 216 mL of toluene, 216 mL of 1,4-dioxane, and 86 mL of distilled water were added to a 1 L round-bottom flask, heated, and refluxed overnight. After confirming the completion of the reaction by thin-layer chromatography, the mixture was cooled to room temperature. The organic layer was extracted with ethyl acetate and distilled water and concentrated under reduced pressure. The substance was separated and purified by column chromatography to obtain <5-a> (26.5 g, 48.2%).

[0454] Synthesis Example 5-2: Synthesis of <5-b>

[0455]

[0456] <5-a> <5-b>

[0457] 26.5 g of <5-a> and 53.6 g of p-toluenesulfonic acid monohydrate were dissolved in 477 mL of acetonitrile in a 3 L round-bottom flask and stirred at room temperature for 30 minutes. 14.3 g of sodium nitrite dissolved in 100 mL of distilled water was slowly added dropwise to the reaction solution. After stirring at room temperature for 2 hours, 37.2 g of copper(I) bromide was added all at once and stirred. After confirming the completion of the reaction by thin-layer chromatography, 200 mL of distilled water was added and stirred, followed by extraction with dichloromethane. After separating the organic layer, the mixture was concentrated under reduced pressure and purified by column chromatography to obtain <5-b> (24 g, 72.4%).

[0458] Synthesis Example 5-3: Synthesis of <5-c>

[0459]

[0460] <5-b> <5-c>

[0461] In the above Synthesis Examples 1-2, <5-b> is used instead of 9-bromoanthracene, and <1-a> Instead, <5-c> was obtained in the same way using 9-anthracene boronic acid. (Yield 78.2%)

[0462] Synthesis Example 5-4: Synthesis of <5-d>

[0463]

[0464] <5-c> <5-d>

[0465] <5-d> was obtained in the same manner as in Synthesis Example 1-3 above, using <5-c> instead of <1-b>. (Yield 79.2%)

[0466] Synthesis Example 5-5: Synthesis of [Compound 17]

[0467]

[0468] <5-d> [Compound 17]

[0469] [Compound 17] was obtained in the same manner as in Synthesis Examples 1-4 above, using <5-d> instead of <1-c>. (Yield 55%)

[0470] MS (MALDI-TOF): m / z 582.28 [M + ]

[0471] Synthesis Example 6. Synthesis of [Compound 21]

[0472] Synthesis Example 6-1: Synthesis of 6-a

[0473]

[0474] <6-a>

[0475] In Synthesis Examples 1-2 above, 2-bromoanthracene was used instead of 9-bromoanthracene, and phenyl-2',3',4',5',6'-d5 boronic acid was used instead of <1-a> to obtain <6-a> in the same manner. (Yield 79%)

[0476] Synthesis Example 6-2: Synthesis of 6-b

[0477]

[0478] <6-a> <6-b>

[0479] In Synthesis Examples 1-3 above, <6-b> was obtained by the same method using <6-a> instead of <1-b>. (Yield 81.4%)

[0480] Synthesis Example 6-3: Synthesis of 6-c

[0481]

[0482] <6-b> <6-c>

[0483] <6-c> was obtained in the same manner as in Synthesis Example 4-1 above, using <6-b> instead of 9-bromoanthracene. (Yield 64%)

[0484] Synthesis Example 6-4: Synthesis of 6-d

[0485]

[0486] <6-c> <6-d>

[0487] <6-d> was obtained in the same manner as in Synthesis Example 1-3 above, using <6-c> instead of <1-b>. (Yield 75.3%)

[0488] Synthesis Example 6-5: Synthesis of [Compound 21]

[0489] <6-d> [Compound 21]

[0490] [Compound 21] was obtained in the same manner as in Synthesis Examples 1-4 above, using <6-d> instead of <1-c>. (Yield 61.2%)

[0491] MS (MALDI-TOF): m / z 577.25 [M + ]

[0492] Synthesis Example 7. Synthesis of [Compound 33]

[0493] Synthesis Example 7-1: Synthesis of 7-a

[0494]

[0495] <7-a>

[0496] <7-a> was obtained in the same manner as in Synthesis Example 4-4 above, using 2-chloro-5-bromodibenzofuran instead of 3,6-dibromodibenzofuran. (Yield 70.5%)

[0497] Synthesis Example 7-2: Synthesis of 7-b

[0498]

[0499] <7-a> <7-b>

[0500] 23.1 g of <7-a>, 26.9 g of bis(pinacolato)diborone, 2 g of dichloropalladium 1,1-bis(diphenylphosphino)ferrocene, 24 g of potassium acetate, 0.5 g of diphenylphosphinoferrocene, and 230 mL of toluene were added to a 500 mL round-bottom flask and refluxed overnight. After confirming the termination of the reaction by thin-layer chromatography, the mixture was filtered using a Celite pad. The material was separated and purified by column chromatography and recrystallized into dichloromethane and heptane to obtain <7-b> (23.6 g, 77.3%).

[0501] Synthesis Example 7-3. Synthesis of [Compound 33]

[0502]

[0503] <4-b> <7-b> [Compound 33]

[0504] [Compound 33] was obtained in the same manner as in Synthesis Examples 2-3 above by using <4-b> instead of <2-b> and <7-b> instead of dibenzofuran-4-ylboronic acid. (Yield 51.2%)

[0505] MS (MALDI-TOF): m / z 577.25 [M + ]

[0506] Synthesis Example 8. Synthesis of [Compound 3]

[0507] Synthesis Example 8-1: Synthesis of [Compound 3]

[0508] [Compound 3] was obtained in the same manner as in Synthesis Examples 1-4 above, using <4-b> instead of <1-c>. (Yield 43%)

[0509] MS (MALDI-TOF): m / z 496.18 [M + ]

[0510] Example 1: Preparation of an organic light-emitting diode

[0511] The ITO glass was patterned so that its light-emitting area was 2 mm x 2 mm, and then cleaned. After mounting the ITO glass in a vacuum chamber, the base pressure was 1 x 10 -7 After making the torr, a film (50 Å) is formed on the above ITO by mixing 5 wt% of [HT] and [Acceptor-1] as a hole injection layer, and a film of [HT] (600 Å) is formed as a hole transport layer. As an emissive layer, a film (200 Å) is formed by mixing the host compound according to the present invention with 3 wt% of the dopant [BD] described below, and then [Chemical Formula E-1] and [Chemical Formula E- 2 An organic light-emitting diode was fabricated by mixing ] in a 1:1 ratio and depositing a film (250 Å), depositing [Chemical Formula E-2] (10 Å) as an electron injection layer, and depositing Al (1000 Å) as a cathode. The luminescence characteristic of the above organic light-emitting diode is 10 mA / cm². 2 It was measured at.

[0512] [HT] [Acceptor-1] [BD]

[0513]

[0514] [Chemical Formula E-1] [Chemical Formula E-2]

[0515]

[0516] Comparative Examples 1 to 2: Preparation of organic light-emitting diodes

[0517] An organic light-emitting diode was fabricated in the same manner as in Example 1, except that [BH1] and [BH2] compounds were used instead of the host compound used in Example 1, and the luminescence characteristic of the organic light-emitting diode was 10 mA / cm² 2 Measurements were taken at [location], and the evaluation results of the obtained organic light-emitting diode are shown in Table 1 below.

[0518]

[0519] [BH 1] [BH 2]

[0520] Host V EQE LT 97 Example 1 Compound 13 3.52 12.2 200 Comparative Example 1 [BH 1] 3.65 12.0 80 Comparative Example 2 [BH 2] 3.55 11.8 30

[0521] Examples 2 to 8: Preparation of organic light-emitting diodes

[0522] The ITO glass was patterned so that its light-emitting area was 2 mm x 2 mm, and then cleaned. After mounting the ITO glass in a vacuum chamber, the base pressure was 1 x 10 -7 After making the torr, a film (100 Å) was deposited on the ITO as a hole injection layer with an electron acceptor [Acceptor-1] and [HT] of the following structural formula, such that the deposition ratio of [Acceptor-1] : [HT] = 2 : 98. [HT] was deposited as a hole transport layer (550 Å), and then [Chemical Formula G] was deposited as an electron blocking layer (50 Å). An organic light-emitting diode was fabricated by first forming a light-emitting layer (200 Å) by mixing the compound of the present invention with the dopant [BD 1] (1 wt%) described below, and then subsequently forming a hole-blocking layer [Chemical Formula H] (50 Å), followed by forming electron transport layers [Chemical Formula E-2] and [Chemical Formula E-3] in a 1:1 ratio at 250 Å, electron injection layers [Chemical Formula E-2] at 10 Å, and Al (1000 Å). The light emission characteristic of the organic light-emitting diode is 10 mA / cm². 2 It was measured at.

[0523] [Chemical Formula G] [Chemical Formula H]

[0524]

[0525] [Chemical Formula E-3] [Acceptor-1] [BD 1]

[0526]

[0527] Comparative Examples 3 to 4: Preparation of organic light-emitting diodes

[0528] Organic light-emitting diodes were fabricated in the same manner as in Examples 2 to 8 above, except that [BH1] and [BH2] compounds were used instead of the host compounds used in those examples, and the luminescence characteristics of the organic light-emitting diodes were 10 mA / cm² 2 It was measured at.

[0529] Host LT 97 Example 2 Compound 4 120 Example 3 Compound 7 260 Example 4 Compound 13 230 Example 5 Compound 14 150 Example 6 Compound 17 180 Example 7 Compound 21 126 Example 8 Compound 33 137 Comparative Example 3 [BH 1] 100 Comparative Example 4 [BH 2] 60

[0530] As shown in [Table 1] and [Table 2] above, the compound according to the present invention does not contain deuterium and is shown to have a longer lifespan compared to an anthracene compound without a substituent at A in chemical formula A, indicating high potential for application as an organic light-emitting device.

Claims

Claim 1 An organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode; wherein the organic layer comprises a light-emitting layer comprising a host and a dopant, the host comprises at least one of anthracene compounds represented by [Chemical Formula A], and the dopant comprises at least one of compounds represented by [Chemical Formula B-1] or [Chemical Formula B-2]. [Chemical Formula A] [Structural Formula 1] In the above [Chemical Formula A], A is any one selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted aliphatic aromatic mixed ring group having 3 to 50 carbon atoms, R1 is hydrogen or deuterium, and R, R2 to R 12 The elements are identical 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 silyl group having 0 to 30 carbon atoms, a substituted or unsubstituted aliphatic-aromatic mixed ring group having 3 to 50 carbon atoms, a cyano group, and a halogen group, and each of these may be connected to adjacent substituents to additionally form a monocyclic or polycyclic ring of aliphatic or aromatic and an aliphatic-aromatic mixed ring, wherein n is an integer from 1 to 8, and when n is 2 or more, each R is identical or different from one another, provided that at least one of the Rs is deuterium, and the R6, R7, and R in Structural Formula 1 10 and R 11 One of them is a single bond bonded to an aromatic carbon atom in the anthracene of the above chemical formula A, [Chemical Formula B-1] [Chemical Formula B-2] In the above [Chemical Formula B-1] and [Chemical Formula B-2], A1 to A3 are each identical or different and independently selected from an aromatic hydrocarbon ring having 6 to 50 carbon atoms, an aliphatic ring having 3 to 30 carbon atoms, and a mixed aliphatic or aromatic ring having 3 to 30 carbon atoms, wherein each substituent within the A1 to A3 rings may be connected to adjacent substituents to additionally form a monocyclic or polycyclic ring of alicyclic or aromatic, and Y1 and Y2 are identical or different and independently selected from NR 21 , CR 22 R 23 It is any one selected from , O, and S, and the above R 21 to R 23 is identical or different from one another and is independently selected from hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C0 to C30 silyl group, a substituted or unsubstituted C3 to C30 aliphatic aromatic mixed ring, a cyano group, and a halogen group, and R 21 to R 23 Each may additionally form a monocyclic or polycyclic ring of alicyclic or aromatic by combining with one or more rings selected from the above A1 to A3 rings, and the 'substitution' in 'substituted or unsubstituted' in [Chemical Formula A], [Chemical Formula B-1], and [Chemical Formula B-2] is one selected from the group consisting of deuterium, cyano group, halogen group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, cycloalkyl group having 3 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, alkylaryl group having 7 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, amine group having 0 to 24 carbon atoms, silyl group having 0 to 24 carbon atoms, and aliphatic-aromatic mixed ring group having 3 to 30 carbon atoms. It means being substituted with the above substituents. Claim 2 An organic light-emitting device according to claim 1, characterized in that in [Chemical Formula A], A is a deuterium-substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Claim 3 An organic light-emitting device according to claim 2, wherein in [Chemical Formula A], A is selected from any one of a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a deuterium-substituted or unsubstituted terphenyl group, a deuterium-substituted or unsubstituted naphthyl group, or a deuterium-substituted or unsubstituted phenanthyl group. Claim 4 delete Claim 5 An organic light-emitting device according to claim 1, characterized in that at least one of R2 to R4 in [Chemical Formula A] is selected from hydrogen, deuterium, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Claim 6 In claim 1, the R5 to R in the above [Chemical Formula A] 12 An organic light-emitting device characterized in that at least one of the above-mentioned non-single bond substituents is a deuterium-substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Claim 7 An organic light-emitting device according to claim 1, characterized in that the degree of deuteration of the anthracene compound represented by [Chemical Formula A] is 20% or more. Claim 8 An organic light-emitting device according to claim 7, characterized in that the degree of deuteration of the anthracene compound represented by [Chemical Formula A] is 35% or more. Claim 9 An organic light-emitting device according to claim 1, characterized in that the anthracene compound represented by [Chemical Formula A] is any one of [Compound 5] to [Compound 9], [Compound 12], [Compound 28], [Compound 36], [Compound 45], [Compound 54], and [Compound 58]. [Compound 5] [Compound 6] [Compound 7] [Compound 8] [Compound 9] [Compound 12] [Compound 28] [Compound 36] [Compound 45] [Compound 54] [Compound 58] Claim 10 An organic light-emitting device according to claim 1, characterized in that in [Chemical Formula B-1] and [Chemical Formula B-2], A1 to A3 are identical or different from each other and are each independently substituted or unsubstituted aromatic hydrocarbon rings having 6 to 30 carbon atoms. Claim 11 In claim 1, at least one of Y1 and Y2 in [Chemical Formula B-1] and [Chemical Formula B-2] is NR 21 An organic light-emitting diode characterized by being. Herein, the R 21 It is the same as defined in Claim 1. Claim 12 In Clause 11, R in the above [Chemical Formula B-1] and [Chemical Formula B-2] 21 An organic light-emitting device characterized by having a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Claim 13 An organic light-emitting device according to claim 1, characterized in that the compound represented by [Chemical Formula B-1] or [Chemical Formula B-2] is any one of the following [Chemical Formula 1] to [Chemical Formula 84]. [Chemical Formula 1] [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] [Chemical Formula 16] [Chemical Formula 17] [Chemical Formula 18] [Chemical Formula 19] [Chemical Formula 20] [Chemical Formula 21] [Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 24] [Chemical Formula 25] [Chemical Formula 26] [Chemical Formula 27] [Chemical Formula 28] [Chemical Formula 29] [Chemical Formula 30] [Chemical Formula 31] [Chemical Formula 32] [Chemical Formula 33] [Chemical Formula 34] [Chemical Formula 35] [Chemical Formula 36] [Chemical Formula 37] [Chemical Formula 38] [Chemical Formula 39] [Chemical Formula 40] [Chemical Formula 41] [Chemical Formula 42] [Chemical Formula 43] [Chemical Formula 44] [Chemical Formula 45] [Chemical Formula 46] [Chemical Formula 47] [Chemical Formula 48] [Chemical Formula 49] [Chemical Formula 50] [Chemical Formula 51] [Chemical Formula 52] [Chemical Formula 53] [Chemical Formula 54] [Chemical Formula 55] [Chemical Formula 56] [Chemical Formula 57] [Chemical Formula 58] [Chemical Formula 59] [Chemical Formula 60] [Chemical Formula 61] [Chemical Formula 62] [Chemical Formula 63] [Chemical Formula 64] [Chemical Formula 65] [Chemical Formula 66] [Chemical Formula 67] [Chemical Formula 68] [Chemical Formula 69] [Chemical Formula 70] [Chemical Formula 71] [Chemical Formula 72] [Chemical Formula 73] [Chemical Formula 74] [Chemical Formula 75] [Chemical Formula 76] [Chemical Formula 77] [Chemical Formula 78] [Chemical Formula 79] [Chemical Formula 80] [Chemical Formula 81] [Chemical Formula 82] [Chemical Formula 83] [Chemical Formula 84] Claim 14 An organic light-emitting device according to claim 1, characterized in that the organic layer comprises, in addition to the light-emitting layer, 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 transport layer, and an electron injection layer. Claim 15 An organic light-emitting device according to claim 1, characterized in that the host in the light-emitting layer is one or more host compounds other than an anthracene compound represented by [Chemical Formula A] mixed, or one or more host compounds other than an anthracene compound represented by [Chemical Formula A] are laminated separately from the layer represented by [Chemical Formula A] within the light-emitting layer. Claim 16 An organic light-emitting device according to claim 14, characterized in that at least one layer selected among each of the above layers is formed by a deposition process or a solution process. Claim 17 The organic light-emitting element according to claim 1, characterized in that the organic light-emitting element is used in any one of the following devices: a flat panel display device; a flexible display device; a monochromatic or white flat panel lighting device; a monochromatic or white flexible lighting device; a vehicle display device; and a virtual or augmented reality display device.

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