Organic light emitting diode with high efficiency and long life

Abstract

The present invention relates to an organic light-emitting device characterized by comprising at least two compounds represented by chemical formula A as host materials within the organic light-emitting device, wherein the two compounds represented by chemical formula A are different from each other, and [Chemical formula A] is defined as in the detailed description of the invention.

Description

Technology Field

[0001] The present invention relates to an organic light-emitting device with high efficiency and long lifespan, and more specifically, to an organic light-emitting device that can be driven at low voltage and can achieve higher efficiency and longer lifespan characteristics by including two or more anthracene derivatives having different structures that share a certain portion of the core structure within the organic light-emitting device including the light-emitting layer. 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 luminescence efficiency through energy transfer.

[0008] The principle is that when a small amount of a dopant with 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, producing high-efficiency light. At this time, since the wavelength of the host shifts to the wavelength range of the dopant, light of a desired wavelength can be obtained depending on the type of dopant used.

[0009] As prior art regarding host compounds among such light-emitting layers, Korean Patent Publication No. 10-2015-0043020 (April 22, 2015) describes a technology in which a compound with a phenyl-anthracene-naphnyl structure is used as a light-emitting material in an organic light-emitting device, and Japanese Registered Patent Publication No. 5608978 (Oct. 22, 2014) describes a technology in which an anthracene derivative having a dibenzofuran structure substituent attached to the end of an anthracene structure is included in the light-emitting layer.

[0010] However, despite the fact that various types of compounds for use in the light-emitting layer, including the aforementioned conventional technology, have been manufactured and applied to organic light-emitting diodes, there is still a continuous demand for the development of organic layer materials for organic light-emitting diodes that can drive the device with high efficiency and long lifespan characteristics at lower voltages. Prior art literature

[0011] Published Patent Application No. 10-2015-0043020 (April 22, 2015) Japanese Registered Patent Application No. 5608978 (October 22, 2014) The problem to be solved

[0012] The present invention aims to solve the aforementioned problems by providing an organic light-emitting device that includes a structure in which a dibenzofuran group or a dibenzothiophene group is connected to an anthracene group as a host in the light-emitting layer of the organic light-emitting device, and by introducing two or more anthracene derivatives having different structures together into the light-emitting layer, thereby enabling operation at a lower voltage and providing high efficiency and long lifespan characteristics. means of solving the problem

[0013] To this end, the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and a light-emitting layer interposed between the first electrode and the second electrode; wherein the light-emitting layer comprises a host and a dopant, and the host comprises at least two types of compounds represented by the following chemical formula A, wherein the two types of compounds represented by the chemical formula A are different from each other.

[0014] [Chemical Formula A]

[0015]

[0016] In the above [Chemical Formula A],

[0017] The above substituents R1 to R 16Each is identical or different and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl 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 Any one selected from an arylthioxy group, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group, wherein R9 to R 16 One of them is a single coupling that combines with the above connector L, and

[0018] The above substituent Ar1 is any one selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and

[0019] The above linker L is any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0020] The above n is any one integer from 1 to 3, and when n is 2 or greater, each connector L is identical or different from each other, and

[0021] The above X is O or S, and

[0022] The term 'substituted' in 'substituted or unsubstituted' in the above [Chemical Formula A] 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, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 2 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, and alkyl of 12 to 24 carbon atoms. It means being substituted with one or more substituents selected from the group consisting of a diarylamino group, a diheteroarylamino group having 2 to 24 carbon atoms, an aryl(heteroaryl)amino group having 7 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and an arylthionyl group having 6 to 24 carbon atoms. Effects of the invention

[0023] The organic light-emitting device according to the present invention includes a structure in which a dibenzofuran or dibenzothiophene group is connected to an anthracene group as a host material in the light-emitting layer, and by introducing two or more different anthracene compounds together, it is possible to realize an organic light-emitting device with improved physical properties, such as low voltage driving, high efficiency, and long lifespan characteristics. Brief explanation of the drawing

[0024] 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

[0025] 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.

[0026] 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.

[0027] 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.

[0028] 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.

[0029] The present invention provides an organic light-emitting diode with improved physical properties, including high efficiency and long lifespan characteristics along with low voltage driving, by introducing together two or more anthracene derivative compounds having different structures and not having a large difference in molecular weight, as a host material in the light-emitting layer of the organic light-emitting diode to improve the high efficiency and long lifespan characteristics of the organic light-emitting diode.

[0030] In particular, as a host within the light-emitting layer, an anthracene ring or a structure in which a connector L is coupled to the anthracene ring Two or more host materials derived from dibenzofuran or dibenzothiophen hydrocarbons are used, wherein the dibenzofuran or dibenzothiophen ring containing only one oxygen or sulfur atom as a heteroatom is bonded as a substituent, and the remainder consists only of carbon atoms and hydrogen (including deuterium) atoms. By ensuring that their molecular weights do not differ significantly, the mixing of each material within the deposition source is facilitated, and they have similar sublimation temperatures. Consequently, they can be mixed within a single deposition source and introduced into the deposition process. This ensures greater uniformity and stability of the deposition process during deposition, thereby enabling the manufacture of an organic light-emitting device in which the light-emitting layer exhibits higher efficiency and a longer lifespan.

[0031] To explain this in more detail, the organic light-emitting element according to the present invention comprises: a first electrode; a second electrode facing the first electrode; and a light-emitting layer interposed between the first electrode and the second electrode; wherein the light-emitting layer comprises a host and a dopant, and the host comprises at least two types of compounds represented by the following chemical formula A, wherein the two types of compounds represented by the chemical formula A are different from each other.

[0032] [Chemical Formula A]

[0033]

[0034] In the above [Chemical Formula A],

[0035] The above substituents R1 to R 16 Each is identical or different and independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C5 to C30 cycloalkenyl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl 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 Any one selected from an arylthioxy group, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group, wherein R9 to R 16 One of them is a single coupling that combines with the above connector L, and

[0036] The above substituent Ar1 is any one selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and

[0037] The above linker L is any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0038] The above n is any one integer from 1 to 3, and when n is 2 or greater, each connector L is identical or different from each other, and

[0039] The above X is O or S, and

[0040] The term 'substituted' in 'substituted or unsubstituted' in the above [Chemical Formula A] 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, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 2 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, and alkyl of 12 to 24 carbon atoms. It means being substituted with one or more substituents selected from the group consisting of a diarylamino group, a diheteroarylamino group having 2 to 24 carbon atoms, an aryl(heteroaryl)amino group having 7 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and an arylthionyl group having 6 to 24 carbon atoms.

[0041] Meanwhile, considering the range of the alkyl group or aryl group in the "substituted or unsubstituted alkyl group having 1 to 24 carbon atoms" and "substituted or unsubstituted aryl group having 6 to 50 carbon atoms" in the present invention, the range of the number of carbon atoms of the alkyl group having 1 to 24 carbon atoms and the aryl group having 6 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.

[0042] 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.

[0043] 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.

[0044] The heteroaryl group, which is a substituent used in the compound of the present invention, refers to a cyclic aromatic system having 2 to 50 carbon atoms, preferably 2 to 24, in which one, two, or three heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te are present and the remaining ring atoms are carbon atoms, 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.

[0045] 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 preferably, one to three aromatic carbons in the aromatic hydrocarbon may be substituted with one or more heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te.

[0046] Specific examples of alkyl groups used as substituents in the present invention include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, etc., and one or more hydrogen atoms of the alkyl groups can be substituted with substituents similar to those in the case of the aryl groups.

[0047] Specific examples of alkoxy groups that are substituents used in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, etc., and one or more hydrogen atoms of the alkoxy groups can be substituted with substituents similar to those of the aryl groups.

[0048] Specific examples of silyl groups that are substituents used in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc., and one or more hydrogen atoms of the silyl groups can be substituted with substituents similar to those of the aryl groups.

[0049] The anthracene compound represented by [Chemical Formula A] according to the present invention is an anthracene derivative compound in which a substituent (Ar1) at position 9 of the anthracene ring is bonded as a substitute (Ar1) to 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 a linker (L) at position 10 of the anthracene ring is bonded as a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, wherein a dibenzofuran ring represented by the following structural formula A or a dibenzothiophene ring represented by the following structural formula B is bonded as a substituent to the linker (L) (wherein substituents R9 to R in Chemical Formulas A and B). 16 An organic light-emitting diode that uses two or more different compounds among the anthracene compounds represented by [Chemical Formula A] as hosts in the light-emitting layer, and is characterized by using a single bond that combines with the above-mentioned linker L, is technically characterized by using [Chemical Formula A], can have improved characteristics such as low voltage driving, high efficiency, and long lifespan.

[0050]

[0051] [Structural Formula A] [Structural Formula B]

[0052] At this time, the organic light-emitting device according to the present invention uses two or more different materials as hosts within the light-emitting layer, and by not having a large difference in the molecular weight of each compound used, the deposition conditions of the compounds used (1x10 -5By ensuring that the vapor pressure of each compound at a pressure of torr or less falls within a similar range, uniformity can be achieved during deposition and stability of the deposited light-emitting layer can be ensured. Accordingly, it is possible to realize an organic light-emitting device that exhibits high efficiency and long lifespan characteristics at low voltage compared to conventional organic light-emitting devices.

[0053] In the present invention, the difference in molecular weight between the two compounds represented by compound A, which is used as a host in the light-emitting layer, may be 300 or less, preferably 200 or less, more preferably 180 or less, more preferably 150 or less, more preferably 140 or less, more preferably 130 or less, more preferably 120 or less, more preferably 110 or less, more preferably 100 or less, more preferably 90 or less, more preferably 80 or less, more preferably 70 or less, more preferably 60 or less, more preferably 50 or less, more preferably 40 or less, more preferably 30 or less, more preferably 20 or less, and more preferably, more preferably 10 or less.

[0054] In one embodiment, the substituents R1 to R8 in [Chemical Formula A] of the present invention may each be the same or different and may be hydrogen or deuterium independently of each other.

[0055] As one embodiment, the substituent Ar1 in [Chemical Formula A] of the present invention is It may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

[0056] In one embodiment, when the substituent Ar1 is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, the substituent Ar1 may be any one selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted fluorenyl group.

[0057] In addition, as one embodiment, the linker L in [Chemical Formula A] of the present invention may be a single bond or a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and in this case, preferably, the linker L may be a single bond or any one selected from [Structural Formula 21] to [Structural Formula 27] below.

[0058] [Structural Formula 21] [Structural Formula 22] [Structural Formula 23] [Structural Formula 24]

[0059]

[0060] [Structural Formula 25] [Structural Formula 26] [Structural Formula 27]

[0061]

[0062] At this time, hydrogen or deuterium can be bonded to the carbon site of the aromatic ring in the above-mentioned connector L.

[0063] As one embodiment, in the organic light-emitting element of the present invention, among the two or more compounds represented by [Chemical Formula A], one or more compounds may include at least one deuterium.

[0064] As one embodiment, in the organic light-emitting device of the present invention, each of the two or more compounds represented by [Chemical Formula A] may include at least one deuterium.

[0065] As one embodiment, the host in the organic light-emitting diode of the present invention is represented by [Chemical Formula A] and may consist only of two different types of compounds.

[0066] As one embodiment, the host in the organic light-emitting diode of the present invention may include one or more compounds selected from [Chemical Formula A-1] and [Chemical Formula A-2] below, and may also include one or more compounds represented by the chemical formula A.

[0067] [Chemical Formula A-1] [Chemical Formula A-2]

[0068]

[0069] Here, the above R1 to R 15 , Ar1, L, n, and X are each the same as previously defined.

[0070] That is, the present invention provides an organic light-emitting device having high efficiency and long lifespan characteristics by introducing two or more anthracene compounds with small differences in molecular weight together, as a host material in the light-emitting layer of an organic light-emitting device, by including one or more compounds represented by the chemical formula A, [Chemical Formula A-1] in which a linker L is bonded to the 1st position of a dibenzofuran ring or dibenzothiophen ring in the molecule, and [Chemical Formula A-2] in which a linker L is bonded to the 2nd position of a dibenzofuran ring or dibenzothiophen ring in the molecule.

[0071] As one embodiment, the host in the organic light-emitting diode of the present invention comprises two or more compounds selected from [Chemical Formula A-1] and [Chemical Formula A-2], and these may be different from each other.

[0072] In one embodiment, the host in the organic light-emitting device of the present invention may include two or more compounds represented by [Chemical Formula A-1], wherein they are each different from each other; or, the host in the organic light-emitting device of the present invention may include two or more compounds represented by [Chemical Formula A-2], wherein they are each different from each other.

[0073] As one embodiment, the host in the organic light-emitting diode of the present invention comprises one or more compounds represented by [Chemical Formula A-1] and one or more compounds represented by [Chemical Formula A-2], wherein these may be different from each other.

[0074] As one embodiment, the host in the organic light-emitting diode of the present invention is selected from [Chemical Formula A-1] and [Chemical Formula A-2] and may consist only of two different types of compounds.

[0075] In one embodiment, the host in the organic light-emitting device of the present invention may comprise only two types of compounds represented by [Chemical Formula A-1], wherein they are each different from each other; or, the host in the organic light-emitting device of the present invention may comprise only two types of compounds represented by [Chemical Formula A-2], wherein they are each different from each other.

[0076] As one embodiment, the host in the organic light-emitting diode of the present invention may include one compound represented by [Chemical Formula A-1] and one compound represented by [Chemical Formula A-2], so that they may be different from each other.

[0077] In one embodiment, each of the substituents R1 to R8 in [Formula A-1] and [Formula A-2] may be the same or different and may be hydrogen or deuterium independently of each other.

[0078] In one embodiment, the substituent Ar1 in [Formula A-1] and [Formula A-2] may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted fluorenyl group, and preferably may be a deuterium-substituted or unsubstituted phenyl group.

[0079] In one embodiment, the linker L in [Chemical Formula A-1] and [Chemical Formula A-2] may be a single bond or any one selected from [Structural Formula 21] to [Structural Formula 27] below.

[0080] [Structural Formula 21] [Structural Formula 22] [Structural Formula 23] [Structural Formula 24]

[0081]

[0082] [Structural Formula 25] [Structural Formula 26] [Structural Formula 27]

[0083]

[0084] In the above linker L, the carbon site of the aromatic ring can be bonded to hydrogen or deuterium.

[0085] As one embodiment, substituents R9 to R in [Chemical Formula A-1] and [Chemical Formula A-2] 15 At least one of the substituents may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms. For example, one of the substituents R9 to R11 may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or one of the substituents R12 to R15 may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and preferably the substituents R9 to R 15 One or two of the substituents may be substituted or unsubstituted aryl groups having 6 to 18 carbon atoms.

[0086] Meanwhile, in the present invention, the compound represented by [Chemical Formula A] may be a hydrocarbon composed only of carbon atoms and hydrogen atoms, excluding X as a molecular component; or a hydrocarbon composed only of carbon atoms, deuterium atoms, and hydrogen atoms, excluding X as a molecular component.

[0087] That is, by using a compound represented by the above [Chemical Formula A] as a host, which is a hydrocarbon composed only of carbon atoms and hydrogen atoms (including deuterium atoms) with the exception of X, the polar portion within each of these host compounds is minimized, thereby allowing the heating temperature of the deposition source at a specific pressure during the deposition process to be lowered.

[0088] As an exemplary case of a compound corresponding to the above 'a hydrocarbon whose molecular components consist only of carbon atoms and hydrogen atoms; or a hydrocarbon whose molecular components consist only of carbon atoms, deuterium atoms, and hydrogen atoms;', among the respective substituents excluding the dibenzofuran group and dibenzothiophen group in the compound represented by [Chemical Formula A], substituents R1 to R8 are each identical or different and independently hydrogen or deuterium, substituent Ar1 is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and additionally, the linker L is a single bond or a substituted or unsubstituted arylene group having 6 to 18 carbon atoms.

[0089] In particular, as a host in the above-mentioned light-emitting layer, two or more types of host materials derived from dibenzofuran (or dibenzothiophene) hydrocarbons are used, in which only one oxygen or sulfur atom is included as a heterocyclic ring within the molecule and the remainder consists only of carbon atoms and hydrogen (including deuterium) atoms, and the molecular weights of these materials do not differ significantly, thereby suppressing the polar parts of each material, so that they can be easily mixed with each other within the deposition source and at the same time have a similar range of sublimation degrees (sublimation temperature) under the same pressure during the deposition process, thereby ensuring the stability and uniformity of the deposited light-emitting layer.

[0090] In addition, in the prior art, when multiple host materials are used in a deposition process, if the deposition levels of the compounds used differ, there is a disadvantage in that each of these deposition sources must be separately provided in the deposition chamber. However, when the host materials according to the present invention are used together, there is an additional advantage in that each of these hosts can be mixed and deposited in a single deposition source.

[0091] In addition, according to a specific example of the present invention, in a deposition process of a compound represented as compound A included as a host material for a light-emitting layer in an organic light-emitting device of the present invention, the difference in deposition temperature for each deposition target compound may be 30°C (degrees) or less, preferably 25°C or less, more preferably 20°C or less, more preferably 15°C or less, more preferably 10°C or less, and more preferably 5°C or less.

[0092] Here, the deposition temperature refers to the temperature inside the chamber (temperature below the deposition source) when depositing a deposition material (substance) onto a substrate to be deposited at a rate of 1 oz / s in a cluster deposition equipment for performing the deposition process, provided that all deposition conditions except for differences in material (pressure, location and size of the deposition source, and content of the deposition material) are identical; this temperature may vary depending on the inherent characteristics of the material to be deposited, and the deposition chamber pressure at this time is 10 -4 torr or less, preferably the deposition chamber pressure is 10 -5 torr or less, more preferably 10 -6 torr or less, more preferably 10 -7 It may mean cases below torr.

[0093] In addition, the anthracene derivative represented by [Chemical Formula A] according to the present invention may be represented by any one selected from the group represented by <Compound 1> to <Compound 309> below, but is not limited thereto.

[0094]

[0095] <Compound 1><Compound 2><Compound 3>

[0096]

[0097] <Compound 4><Compound 5><Compound 6>

[0098]

[0099] <Compound 7><Compound 8><Compound 9>

[0100]

[0101] <Compound 10><Compound 11><Compound 12>

[0102]

[0103] <Compound 13><Compound 14><Compound 15>

[0104]

[0105] <화합물 16><화합물 17><화합물 18>

[0106]

[0107] <화합물 19><화합물 20><화합물 21>

[0108]

[0109] <화합물 22><화합물 23><화합물 24>

[0110]

[0111] <화합물 25><화합물 26><화합물 27>

[0112]

[0113] <화합물 28><화합물 29><화합물 30>

[0114]

[0115] <화합물 31> <화합물 32><화합물 33>

[0116]

[0117] <화합물 34> <화합물 35> <화합물 36>

[0118]

[0119] <화합물 37> <화합물 38> <화합물 39>

[0120]

[0121] <화합물 40> <화합물 41> <화합물 42>

[0122]

[0123] <화합물 43> <화합물 44> <화합물 45>

[0124]

[0125] <화합물 46> <화합물 47> <화합물 48>

[0126]

[0127] <화합물 49> <화합물 50> <화합물 51>

[0128]

[0129] <화합물 52> <화합물 53> <화합물 54>

[0130]

[0131] <화합물 55> <화합물 56> <화합물 57>

[0132]

[0133] <화합물 58> <화합물 59> <화합물 60>

[0134]

[0135] <화합물 61> <화합물 62> <화합물 63>

[0136]

[0137] <화합물 64> <화합물 65> <화합물 66>

[0138]

[0139] <화합물 67> <화합물 68> <화합물 69>

[0140]

[0141] <화합물 70> <화합물 71> <화합물 72>

[0142]

[0143] <화합물 73> <화합물 74> <화합물 75>

[0144]

[0145] <화합물 76> <화합물 77> <화합물 78>

[0146]

[0147] <화합물 79> <화합물 80> <화합물 81>

[0148]

[0149] <화합물 82> <화합물 83> <화합물 84>

[0150]

[0151] <화합물 85> <화합물 86> <화합물 87>

[0152]

[0153] <화합물 88> <화합물 89> <화합물 90>

[0154]

[0155] <화합물 91> <화합물 92> <화합물 93>

[0156]

[0157] <화합물 94> <화합물 95> <화합물 96>

[0158]

[0159] <화합물 97> <화합물 98> <화합물 99>

[0160]

[0161] <화합물 100> <화합물 101> <화합물 102>

[0162]

[0163] <화합물 103> <화합물 104> <화합물 105>

[0164]

[0165] <화합물 106> <화합물 107> <화합물 108>

[0166]

[0167] <화합물 109> <화합물 110> <화합물 111>

[0168]

[0169] <화합물 112> <화합물 113> <화합물 114>

[0170]

[0171] <화합물 115> <화합물 116> <화합물 117>

[0172]

[0173] <화합물 118> <화합물 119> <화합물 120>

[0174]

[0175] <화합물 121> <화합물 122> <화합물 123>

[0176]

[0177] <화합물 124> <화합물 125> <화합물 126>

[0178]

[0179] <화합물 127> <화합물 128> <화합물 129>

[0180]

[0181] <화합물 130> <화합물 131> <화합물 132>

[0182]

[0183] <화합물 133> <화합물 134> <화합물 135>

[0184]

[0185] <화합물 136> <화합물 137> <화합물 138>

[0186]

[0187] <화합물 139> <화합물 140> <화합물 141>

[0188]

[0189] <화합물 142> <화합물 143> <화합물 144>

[0190]

[0191] <화합물 145> <화합물 146> <화합물 147>

[0192]

[0193] <화합물 148> <화합물 149> <화합물 150>

[0194]

[0195] <화합물 151> <화합물 152> <화합물 153>

[0196]

[0197] <화합물 154> <화합물 155> <화합물 156>

[0198]

[0199] <화합물 157> <화합물 158> <화합물 159>

[0200]

[0201] <화합물 160> <화합물 161> <화합물 162>

[0202]

[0203] <화합물 163> <화합물 164> <화합물 165>

[0204]

[0205] <화합물 166> <화합물 167> <화합물 168>

[0206]

[0207] <화합물 169> <화합물 170> <화합물 171>

[0208]

[0209] <화합물 172> <화합물 173> <화합물 174>

[0210]

[0211] <화합물 175> <화합물 176> <화합물 177>

[0212]

[0213] <화합물 178> <화합물 179> <화합물 180>

[0214]

[0215] <화합물 181> <화합물 182> <화합물 183>

[0216]

[0217] <화합물 184> <화합물 185> <화합물 186>

[0218]

[0219] <화합물 187> <화합물 188> <화합물 189>

[0220]

[0221] <화합물 190> <화합물 191> <화합물 192>

[0222]

[0223] <화합물 193> <화합물 194> <화합물 195>

[0224]

[0225] <화합물 196> <화합물 197> <화합물 198>

[0226]

[0227] <화합물 199> <화합물 200> <화합물 201>

[0228]

[0229] <화합물 202> <화합물 203> <화합물 204>

[0230]

[0231] <화합물 205> <화합물 206> <화합물 207>

[0232]

[0233] <화합물 208> <화합물 209> <화합물 210>

[0234]

[0235] <화합물 211> <화합물 212> <화합물 213>

[0236]

[0237] <화합물 214> <화합물 215> <화합물 216>

[0238]

[0239] <화합물 217> <화합물 218> <화합물 219>

[0240]

[0241] <화합물 220> <화합물 221> <화합물 222>

[0242]

[0243] <화합물 223> <화합물 224> <화합물 225>

[0244]

[0245] <화합물 226> <화합물 227> <화합물 228>

[0246]

[0247] <화합물 229> <화합물 230> <화합물 231>

[0248]

[0249] <화합물 232> <화합물 233> <화합물 234>

[0250]

[0251] <화합물 235> <화합물 236> <화합물 237>

[0252]

[0253] <화합물 238> <화합물 239> <화합물 240>

[0254]

[0255] <화합물 241> <화합물 242> <화합물 243>

[0256]

[0257] <화합물 244> <화합물 245> <화합물 246>

[0258]

[0259] <화합물 247> <화합물 248> <화합물 249>

[0260]

[0261] <화합물 250> <화합물 251> <화합물 252>

[0262]

[0263] <화합물 253><화합물 254><화합물 255>

[0264]

[0265] <화합물 256><화합물 257><화합물 258>

[0266]

[0267] <화합물 259><화합물 260><화합물 261>

[0268]

[0269] <화합물 262><화합물 263><화합물 264>

[0270]

[0271] <화합물 265><화합물 266><화합물 267>

[0272]

[0273] <화합물 268><화합물 269><화합물 270>

[0274]

[0275] <화합물 271><화합물 272><화합물 273>

[0276]

[0277] <화합물 274><화합물 275><화합물 276>

[0278]

[0279] <화합물 277><화합물 278><화합물 279>

[0280]

[0281] <화합물 280><화합물 281><화합물 282>

[0282]

[0283] <화합물 283><화합물 284><화합물 285>

[0284]

[0285] <화합물 286><화합물 287><화합물 288>

[0286]

[0287] <화합물 289><화합물 290><화합물 291>

[0288]

[0289] <화합물 292><화합물 293><화합물 294>

[0290]

[0291] <화합물 295><화합물 296><화합물 297>

[0292]

[0293] <화합물 298><화합물 299><화합물 300>

[0294]

[0295] <화합물 301><화합물 302><화합물 303>

[0296]

[0297] <화합물 304><화합물 305><화합물 306>

[0298]

[0299] <Compound 307><Compound 308><Compound 309>

[0300] Meanwhile, in the present invention, a host comprising an anthracene compound represented by the chemical formula A according to the present invention and, in addition, a dopant material may be used.

[0301] As a dopant compound used in the light-emitting layer in the present invention, at least one compound represented by any one of the following [Chemical Formula D1] to [Chemical Formula D8] may be included.

[0302] [Chemical Formula D1]

[0303]

[0304] [Chemical Formula D2]

[0305]

[0306] In the above [Chemical Formula D1] and [Chemical Formula D2],

[0307] Above A 31 , A 32 , E1 and F1 are each identical or different and independently substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms, or substituted or unsubstituted aromatic heterocycles having 2 to 40 carbon atoms;

[0308] Above A 31 Two adjacent carbon atoms within the aromatic ring of, and the above A 32 Two adjacent carbon atoms within the aromatic ring are the substituent R 51 and R 52 By forming a five-membered ring with the carbon atom connected to it, they each form a condensation ring;

[0309] The above connector L 21 to L 32Each is identical or different and independently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;

[0310] The above W and W' are each the same or different and independently NR 53 , CR 54 R 55 , SiR 56 R 57 , GeR 58 R 59 It is any one selected from , O, S, Se;

[0311] The above substituent R 51 to R 59 , Ar 21 or Ar 28Each is identical or different and 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 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, and a substituted or unsubstituted alkoxy group having 5 to 30 carbon atoms. Any one selected from an arylthioxy group, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 30 carbon atoms, a substituted or unsubstituted arylgermanium group having 1 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group, wherein

[0312] The above R 51 and R 52 They can be connected to each other to form alicyclic or aromatic single or polycyclic rings, and the carbon atoms of the formed alicyclic or aromatic single or polycyclic rings can be substituted with one or more heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te;

[0313] The above p11 to p14, r11 to r14, and s11 to s14 are each integers from 1 to 3, wherein each of these is 2 or more, each connector L 21 to L 32 are identical or different from each other,

[0314] The above x1 is 1, and y1, z1, and z2 are each the same or different and are independent integers from 0 to 1, and

[0315] The above Ar 21 and Ar 22 , Ar 23 and Ar 24 , Ar 25 Wa Ar 26 and Ar 27 and Ar 28 Each can be connected to others to form a ring;

[0316] A in the above chemical formula D1 32 Two adjacent carbon atoms within the ring are represented by the above structural formula Q 11 It combines with * to form a condensation ring, and

[0317] In the above chemical formula D2, the above A 31 Two adjacent carbon atoms within the ring are represented by the above structural formula Q 12 It forms a condensation ring by combining with * of, and the above A 32 Two adjacent carbon atoms within the ring are represented by the above structural formula Q 11 It can form a condensation ring by combining with *.

[0318] [Chemical Formula D3]

[0319]

[0320] In the above [Chemical Formula D3],

[0321] The above X1 is any one selected from B, P, and P=O.

[0322] The above T1 to T3 are each identical or different from one another and are independently substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms, or substituted or unsubstituted aromatic heterocycles having 2 to 40 carbon atoms;

[0323] The above Y1 is NR 61 , CR 62 R 63 , O, S, SiR64 R 65 It is one of the selected from among;

[0324] The above Y2 is NR 66 , CR 66 R 68 , O, S, SiR 69 R 70 It is one of the selected from among;

[0325] The above R 61 to R 70 Each is identical or different from one another and independently 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 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 C1 to C30 alkylamine group, a substituted or unsubstituted C5 to C30 arylamine group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C5 to C30 alkylsilyl group, a substituted or unsubstituted C5 to C30 alkylthioxy group It is any one selected from an arylsilyl group, a cyano group, and a halogen group, and the above R 61 to R 70 Each can additionally form a monocyclic or polycyclic ring of alicyclic or aromatic by combining with one or more rings selected from T1 to T3.

[0326] [Chemical Formula D4] [Chemical Formula D5]

[0327]

[0328] In the above [Chemical Formula D4] and [Chemical Formula D5],

[0329] The above X2 is any one selected from B, P, and P=O.

[0330] The above T4 to T6 are identical to T1 to T3 in [Chemical Formula D3], and

[0331] The above Y4 is NR 61 , CR 62 R 63 , O, S, SiR 64 R 65 It is one of the selected from among;

[0332] The above Y5 is NR 66 , CR 66 R 68 , O, S, SiR 69 R 70 It is one of the selected from among

[0333] The above Y6 is NR 71 , CR 72 R 73 , O, S, SiR 74 R 75 It is one of the selected from among;

[0334] The above R 61 to R 75 The above R in [Chemical Formula D3] 61 to R 70 It is identical to.

[0335] [Chemical Formula D6] [Chemical Formula D7]

[0336]

[0337] [Chemical Formula D8]

[0338]

[0339] In the above [Chemical Formula D6] to [Chemical Formula D8],

[0340] The above X is any one selected from B, P, and P=O, and

[0341] The above Q1 to Q3 are each identical to T1 to T3 in [Chemical Formula D3], and

[0342] The above connector Y is any one selected from N-R3, CR4R5, O, S, and Se, and

[0343] The above substituents R3 to R5 are each R in [Chemical Formula D3] 61 to R 70 Same as, but,

[0344] The above R3 to R5 can each combine with the above Q2 ring or Q3 ring to additionally form a monocyclic or aromatic single ring or polycyclic ring, and

[0345] The above R4 and R5 can each be connected to each other to additionally form a monocyclic or aromatic single or polycyclic ring, and

[0346] The ring formed by the above Cy1 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, excluding a nitrogen (N) atom, an aromatic carbon atom in the Q1 ring to which the nitrogen (N) atom is bonded, and an aromatic carbon atom in the Q1 ring to which the above Cy1 is bonded.

[0347] In the above chemical formula D7,

[0348] The above 'Cy2' can be added to the above Cy1 to form a saturated hydrocarbon ring, and the ring formed by the above Cy2 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, excluding the carbon atoms included in Cy1.

[0349] In the above chemical formula D8,

[0350] The ring formed by the above Cy3 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, excluding the aromatic carbon atom in the Q3 ring to be bonded to the above Cy3, the aromatic carbon atom in Q3 to be bonded to the nitrogen (N) atom, the nitrogen (N) atom, and the carbon atom in Cy1 to which the nitrogen (N) atom is bonded.

[0351] The term "substituted" in "substituted or unsubstituted" in [Chemical Formulas D1] to [Chemical Formulas D8] 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, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 2 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, and carbon atoms 12 It means being substituted with one or more substituents selected from the group consisting of diarylamino groups of 1 to 24 carbon atoms, diheteroarylamino groups of 2 to 24 carbon atoms, aryl(heteroaryl)amino groups of 7 to 24 carbon atoms, alkylsilyl groups of 1 to 24 carbon atoms, arylsilyl groups of 6 to 24 carbon atoms, aryloxy groups of 6 to 24 carbon atoms, and arylthionyl groups of 6 to 24 carbon atoms; as a more preferred example, this includes deuterium, cyano groups, halogen groups, hydroxyl groups, nitro groups, alkyl groups of 1 to 12 carbon atoms, halogenated alkyl groups of 1 to 12 carbon atoms, alkenyl groups of 2 to 12 carbon atoms, alkynyl groups of 2 to 12 carbon atoms, cycloalkyl groups of 3 to 12 carbon atoms, heteroalkyl groups of 1 to 12 carbon atoms, and 6 to 18-carbon aryl group, 7 to 20-carbon arylalkyl group, 7 to 20-carbon alkylaryl group, 2 to 18-carbon heteroaryl group, 2 to 18-carbon heteroarylalkyl group, 1 to 12-carbon alkoxy group, 1 to 12-carbon alkylamino group, 12 to 18-carbon diarylamino group, 2 to 18-carbon diheteroarylamino group, 7 to 18-carbon aryl(heteroaryl)amino group, 1 to 12-carbon alkylsilyl group, 6 to 18-carbon arylsilyl group, 6 to 18-carbon aryloxy group,It means being substituted with one or more substituents selected from the group consisting of arylthionyl groups having 6 to 18 carbon atoms.

[0352] Here, the 'Cy1' in [Chemical Formula D6] to [Chemical Formula D8] is connected to a nitrogen (N) atom and an aromatic carbon atom within the Q1 ring to be bonded to the Cy1, respectively, thereby forming a condensed ring including the nitrogen (N) atom, the aromatic carbon atom within the Q1 ring to which the nitrogen (N) atom is bonded, and the aromatic carbon atom within the Q1 ring to be bonded to the Cy1. The ring formed by the Cy1 may be a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, preferably an alkylene group having 2 to 7 carbon atoms, and more preferably an alkylene group having 2 to 5 carbon atoms, except for the nitrogen (N) atom, the aromatic carbon atom within the Q1 ring to which the nitrogen (N) atom is bonded, and the aromatic carbon atom within the Q1 ring to be bonded to the Cy1.

[0353] In addition, the ring formed by 'Cy2' in the above formula D7 may be a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, except for the carbon atom included in Cy1, preferably an alkylene group having 2 to 7 carbon atoms, and more preferably an alkylene group having 2 to 5 carbon atoms.

[0354] In addition, the 'Cy3' in the above chemical formula D8 is connected to the carbon atom bonded to the nitrogen atom in Cy3 and the aromatic carbon atom in the Q3 ring to be bonded to Cy3, respectively, thereby forming a condensation ring including the aromatic carbon atom in the Q3 ring to be bonded to Cy3, the nitrogen (N) atom, and the carbon atom in Cy1 bonded to the nitrogen (N) atom. The ring formed by Cy3 may be a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, preferably an alkylene group having 2 to 7 carbon atoms, and more preferably an alkylene group having 2 to 5 carbon atoms.

[0355] In addition, in the case of a boron compound represented by any one of [Chemical Formula D3] to [Chemical Formula D8] among the dopant compounds according to the present invention, deuterium, an alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, or an arylamino group having 6 to 24 carbon atoms may be substituted as a substituent capable of substituting the aromatic hydrocarbon ring or aromatic heterocycle of T1 to T6, or the aromatic hydrocarbon ring or aromatic heterocycle of Q1 to Q3, wherein, each alkyl group or aryl group in the alkylamino group having 1 to 24 carbon atoms and the arylamino group having 6 to 24 carbon atoms may be connected to each other, and as a more preferred substituent, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, and a substituent having 6 to The 18th arylamino group may be substituted, and each alkyl group or aryl group in the alkylamino group having 1 to 12 carbon atoms and the arylamino group having 6 to 18 carbon atoms may be connected to each other.

[0356] In addition, among the dopant compounds used in the light-emitting layer, specific examples of compounds represented by any one of [Chemical Formula D1] to [Chemical Formula D2] may be any one of the following Chemical Formulas d1 to d239.

[0357] <Chemical Formula d1 > <Chemical Formula d2 > <Chemical Formula d3>

[0358]

[0359] <Chemical Formula d4 > <Chemical Formula d5 > <Chemical Formula d6>

[0360] <Chemical Formula d7 > <Chemical Formula d8 > <Chemical Formula d9>

[0361]

[0362] <Chemical Formula d10 > <Chemical Formula d11 > <Chemical Formula d12>

[0363]

[0364] <Chemical Formula d13 > <Chemical Formula d14 > <Chemical Formula d15>

[0365]

[0366] <Chemical Formula d16 > <Chemical Formula d17 > <Chemical Formula d18>

[0367]

[0368] <Chemical Formula d19 > <Chemical Formula d20 > <Chemical Formula d21>

[0369]

[0370] <Chemical Formula d22 > <Chemical Formula d23 > <Chemical Formula d24>

[0371]

[0372] <Chemical Formula d25 > <Chemical Formula d26 > <Chemical Formula d27>

[0373]

[0374] <화학식 d28 > <화학식 d29 > <화학식 d30>

[0375] <화학식 d31 > <화학식 d32 > <화학식 d33>

[0376]

[0377] <화학식 d34 > <화학식 d35 > <화학식 d36>

[0378]

[0379] <화학식 d37 > <화학식 d38 > <화학식 d39>

[0380] <화학식 d40 > <화학식 d41 > <화학식 d42>

[0381] <화학식 d43 > <화학식 d44 > <화학식 d45>

[0382]

[0383] <화학식 d46 > <화학식 d47 > <화학식 d48>

[0384]

[0385] <화학식 d49 > <화학식 d50 > <화학식 d51>

[0386]

[0387] <화학식 d52 > <화학식 d53 > <화학식 d54>

[0388]

[0389] <화학식 d55 > <화학식 d56 > <화학식 d57>

[0390] <화학식 d58 > <화학식 d59 > <화학식 d60>

[0391]

[0392] <화학식 d61 > <화학식 d62 > <화학식 d63>

[0393]

[0394] <화학식 d64 > <화학식 d65 > <화학식 d66>

[0395] <화학식 d67 > <화학식 d68 > <화학식 d69>

[0396]

[0397] <화학식 d70 > <화학식 d71 > <화학식 d72>

[0398]

[0399] <화학식 d73 > <화학식 d74 > <화학식 d75>

[0400]

[0401] <화학식 d76 > <화학식 d77 > <화학식 d78>

[0402]

[0403] <화학식 d79 > <화학식 d80 > <화학식 d81>

[0404]

[0405] <화학식 d82 > <화학식 d83 > <화학식 d84>

[0406]

[0407] <화학식 d85 > <화학식 d86 > <화학식 d87>

[0408]

[0409] <화학식 d88 > <화학식 d89 > <화학식 d90>

[0410] <화학식 d91 > <화학식 d92 > <화학식 d93>

[0411]

[0412] <화학식 d94 > <화학식 d95 > <화학식 d96>

[0413]

[0414] <화학식 d97 > <화학식 d98 > <화학식 d99>

[0415]

[0416] <화학식 d100 ><화학식 d101 > <화학식 d102>

[0417]

[0418] <화학식 d103 > <화학식 d104 > <화학식 d105>

[0419]

[0420] <화학식 d106 > <화학식 d107 > <화학식 d108>

[0421]

[0422] <화학식 d109 > <화학식 d110 > <화학식 d111>

[0423]

[0424] <화학식 d112 > <화학식 d113 > <화학식 d114>

[0425]

[0426] <화학식 d115 > <화학식 d116 > <화학식 d117>

[0427]

[0428] <화학식 d118 > <화학식 d119 > <화학식 d120>

[0429]

[0430] <화학식 d121 > <화학식 d122 > <화학식 d123>

[0431]

[0432] <화학식 d124 > <화학식 d125 > <화학식 d126>

[0433]

[0434] <화학식 d127 > <화학식 d128 > <화학식 d129>

[0435]

[0436] <화학식 d130 > <화학식 d131 > <화학식 d132>

[0437]

[0438] <화학식 d133 > <화학식 d134 > <화학식135 >

[0439]

[0440] <화학식 d136 > <화학식 d137 > <화학식 d138>

[0441]

[0442] <화학식 d139 > <화학식 d140 > <화학식 d141 >

[0443]

[0444] <화학식 d142 > <화학식 d143 > <화학식 d144>

[0445]

[0446] <화학식 d145 > <화학식 d146 > <화학식 d147>

[0447]

[0448] <화학식 d148 > <화학식 d149 > <화학식 d150>

[0449]

[0450] <화학식 d151 > <화학식 d152 > <화학식 d153>

[0451]

[0452] <화학식 d154 > <화학식 d155 > <화학식 d156>

[0453]

[0454] <화학식 d157 > <화학식 d158 > <화학식 d159>

[0455]

[0456] <화학식 d160 > <화학식 d161 > <화학식 d162>

[0457]

[0458] <화학식 d163 > <화학식 d164 > <화학식 d165>

[0459]

[0460] <화학식 d166 > <화학식 d167 > <화학식 d168>

[0461]

[0462] <화학식 d169 > <화학식 d170 > <화학식 d171>

[0463]

[0464] <화학식 d172 > <화학식 d173 > <화학식 d174>

[0465]

[0466] <화학식 d175 > <화학식 d176 > <화학식 d177>

[0467]

[0468] <화학식 d178 > <화학식 d179 > <화학식 d180>

[0469]

[0470] <화학식 d181 > <화학식 d182 > <화학식 d183>

[0471]

[0472] <화학식 d184 > <화학식 d185 > <화학식 d186>

[0473]

[0474] <화학식 d187 > <화학식 d188 > <화학식 d189>

[0475]

[0476] <화학식 d190 > <화학식 d191 > <화학식 d192>

[0477]

[0478] <화학식 d193 > <화학식 d194 > <화학식 d195>

[0479]

[0480] <화학식 d196 > <화학식 d197 > <화학식 d198>

[0481]

[0482] <화학식 d199 > <화학식 d200 > <화학식 d201>

[0483]

[0484] <화학식 d202 > <화학식 d203 > <화학식 d204>

[0485]

[0486] <화학식 d205 > <화학식 d206 > <화학식 d207>

[0487]

[0488] <화학식 d208 > <화학식 d209 > <화학식 d210>

[0489]

[0490] <화학식 d211 > <화학식 d212 > <화학식 d213>

[0491]

[0492] <화학식 d214 > <화학식 d215 > <화학식 d216>

[0493]

[0494] <Chemical Formula d217 > <Chemical Formula d218 > <Chemical Formula d219>

[0495]

[0496] <Chemical Formula d220 > <Chemical Formula d221 > <Chemical Formula d222>

[0497]

[0498] <Chemical Formula d223 > <Chemical Formula d224 > <Chemical Formula d225>

[0499]

[0500] <Chemical Formula d226 > <Chemical Formula d227 > <Chemical Formula d228>

[0501]

[0502] <Chemical Formula d229 > <Chemical Formula d230 > <Chemical Formula d231>

[0503]

[0504] <Chemical Formula d232 > <Chemical Formula d233 > <Chemical Formula d234>

[0505]

[0506] <Chemical Formula d235 > <Chemical Formula d236 > <Chemical Formula d237>

[0507]

[0508] <Chemical Formula d238 > <Chemical Formula d239 >

[0509]

[0510] In addition, in the present invention, the compound represented by [Chemical Formula D3] may be any one selected from the following <Chemical Formula D101> to <Chemical Formula D130>.

[0511]

[0512] <Chemical Formula D 101> <Chemical Formula D 102> <Chemical Formula D 103>

[0513]

[0514] <화학식 D 104 > <화학식 D 105 > <화학식 D 106>

[0515]

[0516] <화학식 D 107 > <화학식 D 108 > <화학식 D 109>

[0517]

[0518] <화학식 D 110 > <화학식 D 111 > <화학식 D 112>

[0519]

[0520] <화학식 D 113 > <화학식 D 114 > <화학식 D 115>

[0521]

[0522] <화학식 D 116> <화학식 D 117> <화학식 D 118>

[0523]

[0524] <화학식 D 119> <화학식 D 120> <화학식 D 121>

[0525]

[0526] <화학식 D 122> <화학식 D 123> <화학식 D 124>

[0527]

[0528] <화학식 D 125> <화학식 D 126> <화학식 D 127>

[0529]

[0530] <화학식 D 128> <화학식 D 129> <화학식 D 130>

[0531] In addition, in the present invention, the compound represented by either [Chemical Formula D4] and [Chemical Formula D5] may be any one selected from <Chemical Formula D201> to <Chemical Formula D280> below.

[0532]

[0533] [Chemical Formula D201][Chemical Formula D202][Chemical Formula D203][Chemical Formula D204]

[0534]

[0535] [Chemical Formula D205][Chemical Formula D206][Chemical Formula D207][Chemical Formula D208]

[0536]

[0537] [Chemical Formula D209][Chemical Formula D210][Chemical Formula D211][Chemical Formula D212]

[0538]

[0539] [Chemical Formula D213][Chemical Formula D214][Chemical Formula D215][Chemical Formula D216]

[0540]

[0541] [Chemical Formula D217][Chemical Formula D218][Chemical Formula D219][Chemical Formula D220]

[0542]

[0543] [Chemical Formula D221][Chemical Formula D222][Chemical Formula D223][Chemical Formula D224]

[0544]

[0545] [Chemical Formula D225][Chemical Formula D226][Chemical Formula D227][Chemical Formula D228]

[0546]

[0547] [Chemical Formula D229][Chemical Formula D230][Chemical Formula D231][Chemical Formula D232]

[0548]

[0549] [Chemical Formula D233][Chemical Formula D234][Chemical Formula D235][Chemical Formula D236]

[0550]

[0551] [Chemical Formula D237][Chemical Formula D238][Chemical Formula D239][Chemical Formula D240]

[0552]

[0553] [Chemical Formula D241][Chemical Formula D242][Chemical Formula D243][Chemical Formula D244]

[0554]

[0555] [Chemical Formula D245][Chemical Formula D246][Chemical Formula D247][Chemical Formula D248]

[0556]

[0557] [Chemical Formula D249][Chemical Formula D250][Chemical Formula D251][Chemical Formula D252]

[0558]

[0559] [Chemical Formula D253][Chemical Formula D254][Chemical Formula D255][Chemical Formula D256]

[0560]

[0561] [Chemical Formula D257][Chemical Formula D258][Chemical Formula D259][Chemical Formula D260]

[0562]

[0563] [Chemical Formula D261][Chemical Formula D262][Chemical Formula D263][Chemical Formula D264]

[0564]

[0565] [Chemical Formula D265][Chemical Formula D266][Chemical Formula D267][Chemical Formula D268]

[0566]

[0567] [Chemical Formula D269][Chemical Formula D270][Chemical Formula D271][Chemical Formula D272]

[0568]

[0569] [Chemical Formula D273][Chemical Formula D274][Chemical Formula D275][Chemical Formula D276]

[0570]

[0571] [Chemical Formula D277] [Chemical Formula D278][Chemical Formula D279][Chemical Formula D280]

[0572] In addition, in the present invention, the compound represented by any one of [Chemical Formula D6] to [Chemical Formula D8] may be any one selected from <Compound D301> to <Compound D432> below.

[0573] <Compound 301> <Compound 302> <Compound 303>

[0574]

[0575] <Compound 304> <Compound 305> <Compound 306>

[0576]

[0577] <Compound 307> <Compound 308> <Compound 309>

[0578]

[0579] <Compound 310> <Compound 311> <Compound 312>

[0580]

[0581] <Compound 313> <Compound 314> <Compound 315>

[0582]

[0583] <Compound 316> <Compound 317> <Compound 318>

[0584]

[0585] <Compound 319> <Compound 320> <Compound 321>

[0586]

[0587] <화합물 322> <화합물 323> <화합물 324>

[0588]

[0589] <화합물 325> <화합물 326> <화합물 327>

[0590]

[0591] <화합물 328> <화합물 329> <화합물 330>

[0592]

[0593] <화합물 331> <화합물 332> <화합물 333>

[0594]

[0595] <화합물 334> <화합물 335> <화합물 336>

[0596]

[0597] <화합물 337> <화합물 338> <화합물 339>

[0598]

[0599] <화합물 340> <화합물 341> <화합물 342>

[0600]

[0601] <화합물 343> <화합물 344> <화합물 345>

[0602]

[0603] <화합물 346> <화합물 347> <화합물 348>

[0604]

[0605] <화합물 349> <화합물 350> <화합물 351>

[0606]

[0607] <화합물 352> <화합물 353> <화합물 354>

[0608]

[0609] <화합물 355> <화합물 356> <화합물 357>

[0610]

[0611] <화합물 358> <화합물 359> <화합물 360>

[0612]

[0613] <화합물 361> <화합물 362> <화합물 363>

[0614]

[0615] <화합물 364> <화합물 365> <화합물 366>

[0616]

[0617] <화합물 367> <화합물 368> <화합물 369>

[0618]

[0619] <화합물 370> <화합물 371> <화합물 372>

[0620]

[0621] <화합물 373> <화합물 374> <화합물 375>

[0622]

[0623] <화합물 376> <화합물 377> <화합물 378>

[0624]

[0625] <화합물 379> <화합물 380> <화합물 381>

[0626]

[0627] <화합물 382> <화합물 383> <화합물 384>

[0628]

[0629] <화합물 385> <화합물 386> <화합물 387>

[0630]

[0631] <화합물 388> <화합물 389> <화합물 390>

[0632]

[0633] <화합물 391> <화합물92> <화합물93>

[0634]

[0635] <화합물 394> <화합물95> <화합물96>

[0636]

[0637] <화합물 397> <화합물98> <화합물99>

[0638]

[0639] <화합물 400><화합물 401> <화합물 402>

[0640]

[0641] <화합물 403><화합물404><화합물405>

[0642]

[0643] <화합물 406> <화합물 407> <화합물 408>

[0644]

[0645] <화합물 109> <화합물 410> <화합물 411>

[0646]

[0647] <화합물 412> <화합물 413> <화합물 414>

[0648]

[0649] <화합물 415> <화합물 416> <화합물 417>

[0650]

[0651] <Compound 418> <Compound 419> <Compound 420>

[0652]

[0653] <Compound 421> <Compound 422> <Compound 423>

[0654]

[0655] <Compound 424> <Compound 425> <Compound 426>

[0656]

[0657] <Compound 427> <Compound 428><Compound 429>

[0658]

[0659] <Compound 430><Compound 431> <Compound 432>

[0660]

[0661] At this time, the content of the dopant in the light-emitting layer 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.

[0662] In addition, the light-emitting layer may further include various hosts and various dopant materials in addition to the dopant and host.

[0663] Meanwhile, in the present invention, "(the organic layer) comprises one or more organic compounds" can be interpreted as "(the organic layer) may comprise one organic compound belonging to the scope of the present invention or two or more different compounds belonging to the scope of said organic compounds."

[0664] At this time, the organic layer in the organic light-emitting diode of the present invention may additionally include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a capping layer.

[0665] Hereinafter, an organic light-emitting element according to an embodiment of the present invention will be described with reference to the drawings.

[0666] Figure 1 below is a figure illustrating the structure of an organic light-emitting device according to one embodiment of the present invention.

[0667] 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.

[0668] As explained above, the anthracene compounds represented by [Chemical Formula A] can each be used as a host for the light-emitting layer in an organic light-emitting diode.

[0669] 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).

[0670] 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.

[0671] The above hole injection layer (30) material may be used without special limitation as long as it is commonly used in the industry, 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], etc. However, the present invention is not necessarily limited thereto.

[0672] In addition, the material of the hole transport layer (40) is not particularly limited as long as it is commonly used in the industry, 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), etc. may be used. However, the present invention is not necessarily limited thereto.

[0673] Next, a light-emitting layer (50) composed of a plurality of hosts and dopants according to the present invention is laminated on the upper surface 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 the upper surface of the organic light-emitting layer (50).

[0674] Next, a light-emitting layer (50) can be laminated on top of the hole transport layer (40) by a vacuum deposition method or a spin coating method.

[0675] Here, the light-emitting layer (50) may be composed of a host and a dopant, and the materials constituting them are as described above.

[0676] In addition, according to a specific example of the present invention, the thickness of the light-emitting layer (50) is preferably 50 to 2,000 Å.

[0677] Meanwhile, an electron transport layer (60) is deposited on the light-emitting layer using a vacuum deposition method or a spin coating method.

[0678] 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).

[0679] Meanwhile, in the present invention, the electron transport layer (60) material may be a known electron transport material that functions to stably transport electrons injected from an electron injection electrode (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), ADN, compound 201, compound 202, BCP, oxadiazole derivatives such as PBD, BMD, BND, etc., but are not limited thereto.

[0680]

[0681] TAZ BAlq

[0682]

[0683] <Compound 201> <Compound 202> BCP

[0684]

[0685]

[0686] Additionally, the electron transport layer (60) used in the present invention may be an organometallic compound represented by the chemical formula F, used alone or in combination with the electron transport layer material.

[0687] [Chemical Formula F]

[0688]

[0689] In the above [Chemical Formula F],

[0690] Y comprises a portion in which any one selected from C, N, O, and S is directly bonded to M to form a single bond, and a portion in which any one selected from C, N, O, and S is coordinately bonded to M, and is a ligand chelated by the single bond and the coordinate bond.

[0691] The above M is an alkali metal, alkaline earth metal, aluminum (Al), or boron (B) atom, and the above OA is a monovalent ligand capable of single bonding or coordinate bonding with the above M,

[0692] The above O is oxygen, and

[0693] A is any one selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having one or more heteroatoms selected from O, N, S, and Si.

[0694] If the above M is a metal selected from alkali metals, then m=1 and n=0, and

[0695] If the above M is one metal selected from alkaline earth metals, then m=1 and n=1, or m=2 and n=0, and

[0696] If M is boron or aluminum, m is any one of 1 to 3, and n is any one of 0 to 2, satisfying m + n = 3;

[0697] The term "substituted" in the above "substituted or unsubstituted" means being substituted with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, heteroarylamino group, alkylsilyl group, arylsilyl group, aryloxy group, aryl group, heteroaryl group, germanium, phosphorus, and boron.

[0698] In the present invention, Y may be any one selected from [Structural Formula C1] to [Structural Formula C39], each being identical or different and independently thereof, but is not limited thereto.

[0699] [Structural Formula C1][Structural Formula C2][Structural Formula C3]

[0700]

[0701] [Structural Formula C4][Structural Formula C5][Structural Formula C6]

[0702]

[0703] [Structural Formula C7][Structural Formula C8][Structural Formula C9][Structural Formula C10]

[0704]

[0705] [Structural Formula C11] [Structural Formula C12] [Structural Formula C13]

[0706]

[0707] [Structural Formula C14][Structural Formula C15][Structural Formula C16]

[0708]

[0709] [Structural Formula C17][Structural Formula C18][Structural Formula C19][Structural Formula C20]

[0710]

[0711] [Structural Formula C21] [Structural Formula C22] [Structural Formula C23]

[0712]

[0713] [Structural Formula C24][Structural Formula C25][Structural Formula C26]

[0714]

[0715] [Structural Formula C27][Structural Formula C28][Structural Formula C29][Structural Formula C30]

[0716]

[0717] [Structural Formula C31] [Structural Formula C32] [Structural Formula C33]

[0718]

[0719] [Structural Formula C34][Structural Formula C35][Structural Formula C36]

[0720]

[0721] [Structural Formula C37][Structural Formula C38][Structural Formula C39]

[0722]

[0723] In the above [Structural Formula C1] to [Structural Formula C39],

[0724] The above substituents R are identical or different from one another and are each independently selected from hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1 to 30 alkyl group, substituted or unsubstituted C6 to 30 aryl group, substituted or unsubstituted C3 to 30 heteroaryl group, substituted or unsubstituted C1 to 30 alkoxy group, substituted or unsubstituted C3 to 30 cycloalkyl group, substituted or unsubstituted C2 to 30 alkenyl group, substituted or unsubstituted C1 to 30 alkylamino group, substituted or unsubstituted C1 to 30 alkylsilyl group, substituted or unsubstituted C6 to 30 arylamino group, and substituted or unsubstituted C6 to 30 arylsilyl group, and are connected to adjacent substituents via alkylene or alkenylene to form a spiro ring or a fused ring It can form.

[0725] 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 (60), and this does not particularly limit the material.

[0726] Any material known as an electron injection layer forming material, such as CsF, NaF, LiF, NaCl, Li2O, BaO, etc., can be used as the electron injection layer forming material. The deposition conditions of the electron injection layer vary depending on the compound used, but can generally be selected from a range of conditions almost identical to those for forming a hole injection layer.

[0727] 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.

[0728] 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.

[0729] 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.

[0730] In addition, in the present invention, one or more layers selected from the hole injection layer, hole transport layer, light-emitting layer, electron transport layer and electron injection layer may be formed by a deposition process or a solution process.

[0731] 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.

[0732] 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; and a device for monochromatic or white flexible lighting.

[0733] 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.

[0734] Host manufacturing

[0735] Synthesis Example 1. Synthesis of Compound 2

[0736]

[0737] <Compound 2>

[0738] 9-Bromo-10-phenyl-anthracene (10.0 g, 0.030 mol), 7-phenyl-1-dibenzofuranyl-boronic acid (9.5 g, 0.033 mol), tetrakis(triphenylphosphine)palladium (0.7 g, 0.001 mol), and potassium carbonate (6.1 g, 0.044 mol) were placed in a 250 mL round-bottom flask, and 70 mL of toluene, 30 mL of tetrahydrofuran, and 20 mL of water were added. The temperature of the reactor was raised to 90°C and stirred overnight. Upon completion of the reaction, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain <Compound 2> (5.3 g, 35.4%).

[0739] MS (MALDI-TOF): m / z 496.18[M+]

[0740] Synthesis Example 2. Synthesis of Compound 8

[0741] Synthesis Example 2-1. Synthesis of <Intermediate 2-a>

[0742]

[0743] <Intermediate 2-a>

[0744] 2-bromo-1,3-dimethoxybenzene (50 g, 230 mmol) and 400 ml of tetrahydrofuran were added to a 1 L reactor and dissolved; the temperature was then lowered to -78 °C, and normal butyllithium (167 ml, 280 mmol) was added dropwise. After stirring for 2 hours, trimethylborate (36 ml, 320 mmol) was added, and the mixture was stirred overnight at room temperature. After the reaction was complete, the mixture was acidified with normal hydrochloric acid, extracted, and recrystallized to obtain <Intermediate 2-a> (20.8 g, 50%).

[0745] Synthesis Example 2-2. Synthesis of <2-b>

[0746]

[0747] <Intermediate 2-b>

[0748] <Intermediate 2-a> (20.8 g, 110 mmol), 1-bromo-2-fluoro-3-iodobenzene (28.7 g, 95 mmol), tetrakis(triphenylphosphine)palladium (33 g, 29 mmol), and sodium carbonate (30.3 g, 290 mmol) were placed in a 500 ml reactor, and 200 ml of toluene, 60 ml of ethanol, and 60 ml of water were added. The temperature of the reactor was raised to 80 ℃ and stirred for 12 hours; after the reaction was complete, extraction was performed, and the organic layer was separated by column chromatography to obtain <Intermediate 2-b> (22.3 g, 63%).

[0749] Synthesis Example 2-3. Synthesis of <Intermediate 2-c>

[0750]

[0751] <Intermediate 2-c>

[0752] In the above Synthesis Example 2-(2), <Intermediate 2-c> was obtained in the same manner by using phenyl(D5)-boronic acid instead of <Intermediate 2-a> and <Intermediate 2-b> instead of 1-bromo-2-fluoro-3-iodobenzene. (Yield 72%)

[0753] Synthesis Example 2-4. Synthesis of <Intermediate 2-d>

[0754]

[0755] <Intermediate 2-d>

[0756] <Intermediate 2-c> (16.6 g, 53 mmol), hydrobromide (48 ml, 260 mmol), and 100 ml of acetic acid were added to a 500 ml reactor and stirred for 12 hours. After the reaction was complete, extraction was performed, and the organic layer was concentrated under reduced pressure and recrystallized with heptane to obtain <Intermediate 2-d> (17.6 g, 95%).

[0757] Synthesis Example 2-5. Synthesis of <Intermediate 2-e>

[0758]

[0759] <Intermediate 2-e>

[0760] <Intermediate 2-d> (14.3 g, 50 mmol), potassium carbonate (20.7 g, 150 mmol), and 112 ml of N-methyl-2-pyrrolidone were added to a 500 ml reactor and stirred for 12 hours. After the reaction was complete, the organic layer was separated by extraction. The material was recrystallized with heptane to obtain <Intermediate 2-e> (10.6 g, 80%).

[0761] Synthesis Example 2-6. Synthesis of <Intermediate 2-f>

[0762]

[0763] <Intermediate 2-f>

[0764] <Intermediate 2-e> (10.6 g, 40 mmol) was placed in a 500 ml reactor under a nitrogen atmosphere and dissolved in 136 ml of dichloromethane. After cooling the reaction solution to 0 °C, pyridine (10 ml, 110 mmol) was added, followed by the dropwise addition of trifluoromethanesulfonyl anhydride (12.7 g, 68 mmol) while maintaining the same temperature. After stirring at room temperature for 12 hours, 20 ml of water was added to the reaction solution and stirred. The organic layer was separated by extraction with water and dichloromethane, and <Intermediate 2-f> (7.5 g, 47%) was obtained by recrystallization with heptane.

[0765] Synthesis Example 2-7. Synthesis of <Compound 8>

[0766]

[0767] <Compound 8>

[0768] <Intermediate 2-f> (7.5 g, 19 mmol), 10-phenyl-anthracene-9-boronic acid (6.9 g, 23 mmol), tetrakis(triphenylphosphine)palladium (0.66 g, 0.6 mmol), and potassium carbonate (7.9 g, 57 mmol) were placed in a 250 ml reactor. 53 ml of toluene, 23 ml of ethanol, and 23 ml of water were added, the reactor temperature was raised to 80 °C, and the mixture was stirred for 12 hours. After the reaction was complete, methanol was poured in and stirred to separate the organic layer. The organic layer was concentrated under reduced pressure and recrystallized with acetone to obtain <Compound 8> (6.2 g, 65%).

[0769] MS (MALDI-TOF): m / z 501.21 [M+]

[0770] Synthesis Example 3. Synthesis of Compound 60

[0771]

[0772] <Compound 60>

[0773] In Synthesis Example 1 above, <Compound 60> was obtained by the same method using 9-bromo-10-phenyl(D5)-anthracene instead of 9-bromo-10-phenyl-anthracene and 8-phenyl-2-dibenzofuranyl-boronic acid instead of 7-phenyl-1-dibenzofuranyl-boronic acid. (Yield 45.2%)

[0774] MS (MALDI-TOF): m / z 501.21 [M+]

[0775] Synthesis Example 4. Synthesis of Compound 61

[0776] Synthesis Example 4-1. Synthesis of <Intermediate 4-b>

[0777]

[0778] <Intermediate 4-b>

[0779] In Synthesis Example 2-2 above, <Intermediate 4-b> was obtained in the same manner using 4-bromo-2-fluoro-1-iodobenzene instead of 1-bromo-2-fluoro-3-iodobenzene and 2,5-methoxyphenylboronic acid instead of <Intermediate 2-a>. (Yield 60%)

[0780] Synthesis Example 4-2. Synthesis of <Intermediate 4-c>

[0781]

[0782] <Intermediate 4-b> <Intermediate 4-c>

[0783] In Synthesis Example 2-3 above, <Intermediate 4-c> was obtained by the same method except that <Intermediate 4-b> was used instead of <Intermediate 2-b>. (Yield 73%)

[0784] Synthesis Example 4-3. Synthesis of <Intermediate 4-d>

[0785]

[0786] <Intermediate 4-d>

[0787] In Synthesis Example 2-4 above, <Intermediate 4-d> was obtained by the same method except that <Intermediate 4-c> was used instead of <Intermediate 2-c>. (Yield 94%)

[0788] Synthesis Example 4-4. Synthesis of <Intermediate 4-e>

[0789]

[0790] <Intermediate 4-e>

[0791] In Synthesis Examples 2-5 above, <Intermediate 4-e> was obtained by the same method except that <Intermediate 4-d> was used instead of <Intermediate 2-d>. (Yield 82%)

[0792] Synthesis Example 4-5. Synthesis of <Intermediate 4-f>

[0793]

[0794] <Intermediate 4-f>

[0795] In Synthesis Examples 2-6 above, <Intermediate 4-f> was obtained by the same method except that <Intermediate 4-e> was used instead of <Intermediate 2-e> (yield 48%).

[0796] Synthesis Example 4-6. Synthesis of <Compound 61>

[0797]

[0798] <Compound 61>

[0799] Compound 61 was obtained by the same method as in Synthesis Examples 2-7 above, using <Intermediate 4-f> instead of <Intermediate 2-f> and 10-phenyl(D5)-anthracene-9-boronic acid instead of 10-phenyl-anthracene-9-boronic acid. (Yield 64%)

[0800] MS (MALDI-TOF): m / z 506.25 [M+]

[0801] Synthesis Example 5. Synthesis of Compound 65

[0802]

[0803] <Compound 65>

[0804] <Compound 65> was obtained by the same method as in Synthesis Example 1 above, except that 9-bromo-10-phenyl(D5)-anthracene was used instead of 9-bromo-10-phenyl-anthracene. (Yield 40%)

[0805] MS (MALDI-TOF): m / z 501.21[M+]

[0806] Synthesis Example 6. Synthesis of Compound 79

[0807]

[0808] <Compound 79>

[0809] In Synthesis Example 1 above, <Compound 79> was obtained by the same method using 9-bromo-10-phenyl(D5)-anthracene instead of 9-bromo-10-phenyl-anthracene and 2-dibenzofuranylboronic acid instead of 7-phenyl-1-dibenzofuranylboronic acid. (Yield 42%)

[0810] MS (MALDI-TOF): m / z 425.18[M+]

[0811] Synthesis Example 7. Synthesis of Compound 184

[0812]

[0813] <Compound 184>

[0814] <Compound 184> was obtained by the same method as in Synthesis Examples 2-7, except that 10-phenyl(D5)-anthracene-9-boronic acid was used instead of 10-phenyl-anthracene-9-boronic acid. (Yield 68%)

[0815] MS (MALDI-TOF): m / z 506.25 [M+]

[0816] Synthesis Example 8. Synthesis of Compound 185

[0817] Synthesis Example 8-1. Synthesis of <Intermediate 8-a>

[0818]

[0819] <Intermediate 8-a>

[0820] 9,10-Dibromoanthracene (25.0 g, 0.073 mol), phenyl(d5)boronic acid (9.0 g, 0.071 mol), tetrakis(triphenylphosphine)palladium (1.68 g, 0.001 mol), potassium carbonate (20.08 g, 0.145 mol), 125 ml toluene, 125 ml ethanol, and 50 ml water were added to a 500 ml flask, and the reactor was refluxed under a nitrogen atmosphere. After the reaction was terminated, excess methanol was poured in, and the resulting solid was filtered. The filtered solid was filtered to obtain <Intermediate 8-a> (15.7 g, 64%).

[0821] Synthesis Example 8-2. Synthesis of <Compound 185>

[0822]

[0823] <Compound 185>

[0824] Compound 185 was obtained by the same method as in Synthesis Example 1 above, except that intermediate 8-a was used instead of 9-bromo-10-phenyl-anthracene. (Yield 53%)

[0825] MS (MALDI-TOF): m / z 509.26[M+]

[0826] Synthesis Example 9. Synthesis of Compound 193

[0827] Synthesis Example 9-1. Synthesis of <Intermediate 9-a>

[0828]

[0829] <Intermediate 9-a>

[0830] Under a nitrogen atmosphere, bromobenzene (d5) (60.4 g, 0.373 mol) and 480 mL of tetrahydrofuran were added to a 2 L reactor and cooled to -78 °C with stirring. Normal butyllithium (223.6 mL, 0.357 mol) was added dropwise to the cooled reaction solution and stirred at the same temperature for 1 hour. O-phthalaldehyde (20.0 g, 0.149 mol) was dissolved in 100 mL of tetrahydrofuran and added dropwise to the reaction solution, followed by stirring at room temperature. After the reaction was complete, 200 mL of aqueous ammonium chloride was added to terminate the reaction. The reaction solution was extracted with ethyl acetate, concentrated under reduced pressure, and separated by column chromatography to obtain <Intermediate 9-a> (40.0 g, 89%).

[0831] Synthesis Example 9-2. Synthesis of <Intermediate 9-b>

[0832]

[0833] <Intermediate 9-b>

[0834] <Intermediate 9-a> (40.0 g, 0.133 mol) was dissolved in 200 mL of acetic acid in a 500 mL reactor and stirred. 2 mL of hydrogen bromide was added to the reaction solution, and the mixture was stirred at 80 °C for 2 hours. After the reaction was complete, the solution was cooled to room temperature, then slowly poured into a beaker containing 500 mL of water and stirred. The resulting solid was filtered and washed with water. The solid was separated by column chromatography to obtain <Intermediate 9-b> (13 g, 37%).

[0835] Synthesis Example 9-3. Synthesis of <Intermediate 9-c>

[0836]

[0837] <Intermediate 9-c>

[0838] <Intermediate 9-b> (13.0 g, 0.049 mol) was dissolved in 130 mL of N,N-dimethylamide in a 500 mL reactor and stirred at room temperature. N-bromosuccinimide (10.54 g, 0.059 mol) was dissolved in 40 mL of N,N-dimethylamide and added dropwise to the reaction solution. The reaction was terminated by confirming the reaction using thin-layer chromatography. The reaction solution was poured into a beaker containing 500 mL of water and stirred. The resulting solid was filtered and washed with water. The substance was separated by column chromatography to obtain <Intermediate 9-c> (14.0 g, 83%).

[0839] Synthesis Example 9-4. Synthesis of <Compound 193>

[0840]

[0841] <Compound 193>

[0842] In Synthesis Example 1 above, <Compound 193> was obtained by the same method using <Intermediate 9-c> instead of 9-bromo-10-phenyl-anthracene and 8-phenyl-2-dibenzofuranyl-boronic acid instead of 7-phenyl-1-dibenzofuranyl-boronic acid. (Yield 44%)

[0843] MS (MALDI-TOF): m / z 505.24[M+]

[0844] Synthesis Example 10. Synthesis of Compound 195

[0845] Synthesis Example 10-1. Synthesis of <Intermediate 10-a>

[0846]

[0847] <Intermediate 10-a>

[0848] In a 500 mL reactor, <Intermediate 9-c> (50 g, 146 mmol) synthesized in Synthesis Example 9-3 and 500 ml of tetrahydrofuran were added and dissolved. The temperature was then lowered to -78 °C, and normal butyllithium (100 ml, 161 mmol) was added dropwise. After stirring for 5 hours, trimethylborate (18 ml, 161 mmol) was added, and the mixture was stirred overnight at room temperature. After the reaction was complete, the mixture was acidified with normal hydrochloric acid and recrystallized to obtain <Intermediate 10-a> (25 g, 56%).

[0849] Synthesis Example 10-2. Synthesis of <Intermediate 10-b>

[0850]

[0851] <Intermediate 10-b>

[0852] 7-phenyl-1-dibenzofuranol (10.4 g, 40 mmol) was added to a 500 ml round-bottom flask under a nitrogen atmosphere and dissolved in 136 ml of dichloromethane. After cooling the reaction solution to 0 °C, pyridine (10 ml, 110 mmol) was added, followed by the dropwise addition of trifluoromethanesulfonyl anhydride (12.7 g, 68 mmol) while maintaining the same temperature. After stirring at room temperature for 12 hours, 20 ml of water was added to the reaction solution and stirred. The organic layer was separated by extraction with water and dichloromethane, and the solution was recrystallized with heptane by reduced pressure concentration to obtain <intermediate 10-b> (7.4 g, 47%).

[0853] Synthesis Example 10-3. Synthesis of <Compound 195>

[0854]

[0855] <Compound 195>

[0856] In Synthesis Examples 2-7 above, <Compound 195> was obtained in the same manner using <Intermediate 10-a> instead of 10-phenyl-anthracene-9-boronic acid and <Intermediate 10-b> instead of <Intermediate 2-f>. (Yield 63%)

[0857] MS (MALDI-TOF): m / z 525.30 [M+]

[0858] Synthesis Example 11. Synthesis of Compound 198

[0859] Synthesis Example 11-1. Synthesis of <Intermediate 11-a>

[0860]

[0861] <Intermediate 11-a>

[0862] Nitrogen was purged into a 500 ml round-bottom flask, and 8-bromo-2-dibenzofuranol (20 g, 76 mmol), phenylboronic acid (D5) (11.6 g, 91 mmol), tetracysteine ​​triphenylphosphine palladium (1.8 g, 2 mmol), 140 ml toluene, 35 ml ethanol, and 65 ml water were added and refluxed for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature, extracted with ethyl acetate and water, and the organic layer was anhydrous. The organic layer was concentrated under reduced pressure and recrystallized with ethyl acetate and heptane to obtain <Intermediate 11-a> (15.2 g, 75.4%).

[0863] Synthesis Example 11-2. Synthesis of <Intermediate 11-b>

[0864]

[0865] <Intermediate 11-b>

[0866] In Synthesis Example 10-2 above, <Intermediate 11-b> was obtained by the same method except that <Intermediate 11-a> was used instead of 7-phenyl-1-dibenzofuranol. (Yield 86.8%)

[0867] Synthesis Example 11-3. Synthesis of <Intermediate 11-c>

[0868]

[0869] <Intermediate 11-c>

[0870] Nitrogen was purged from a 300 ml round-bottom flask, and <Intermediate 11-b> (20 g, 50 mmol), bispinacholdivoron (16.6 g, 65 mmol), bisdiphenylphosphinoferrocendichloropalladium (0.8 g, 1 mmol), calcium acetate (9.9 g, 101 mmol), and 200 ml of 1,4-dioxane were added and refluxed for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered using Celite, and the filtrate was concentrated and separated by column chromatography to obtain <Intermediate 11-c> (14.8 g, 78.4%).

[0871] Synthesis Example 11-4. Synthesis of <Compound 198>

[0872]

[0873] <Compound 198>

[0874] Nitrogen was purged into a 300 ml round-bottom flask, and <Intermediate 8-a> (10.4 g, 30 mmol), <Intermediate 11-c> (13.7 g, 36 mmol), tetracyclophenylphosphine palladium (0.7 g, 1 mmol), calcium carbonate (7.4 g, 53 mmol), 80 ml toluene, 20 ml ethanol, and 26 ml water were added and refluxed for 4 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was anhydrous, concentrated, and separated by column chromatography to obtain <Compound 198> (8.2 g, 53.4%).

[0875] MS (MALDI-TOF): m / z 509.26[M+]

[0876] Synthesis Example 12. Synthesis of Compound 217

[0877] Synthesis Example 12-1. Synthesis of <Intermediate 12-a>

[0878]

[0879] <Intermediate 12-a>

[0880] <Intermediate 12-a> was obtained by the same method as in Synthesis Example 11-1 above, except that 7-bromo-3-dibenzofuranol was used instead of 8-bromo-2-dibenzofuranol. (Yield 75%)

[0881] Synthesis Example 12-2. Synthesis of <Intermediate 12-b>

[0882]

[0883] <Intermediate 12-b>

[0884] In Synthesis Example 10-2 above, <Intermediate 11-b> was obtained by the same method except that <Intermediate 12-a> was used instead of 7-phenyl-1-dibenzofuranol. (Yield 88%)

[0885] Synthesis Example 12-3. Synthesis of <Intermediate 12-c>

[0886]

[0887] <Intermediate 12-c>

[0888] In the above Synthesis Example 11-3, <Intermediate 12-c> was obtained by the same method, except that <Intermediate 12-b> was used instead of <Intermediate 11-b>. (Yield 77.8%)

[0889] Synthesis Example 12-4. Synthesis of <Compound 217>

[0890]

[0891] <Compound 217>

[0892] In the above Synthesis Example 11-4, <Compound 217> was obtained in the same manner using 9-bromo-10-phenyl(D5)-anthracene instead of <Intermediate 8-a> and <Intermediate 12-c> instead of <Intermediate 11-c>. (Yield 46%)

[0893] MS (MALDI-TOF): m / z 506.25 [M+]

[0894] Synthesis Example 13. Synthesis of Compound 237

[0895]

[0896] <Compound 237>

[0897] In Synthesis Example 1 above, <Compound 237> was obtained by the same method using 9-bromo-10-phenyl(D5)-anthracene instead of 9-bromo-10-phenyl-anthracene and 6-phenyl-4-dibenzofuranyl-boronic acid instead of 7-phenyl-1-dibenzofuranyl-boronic acid. (Yield 40%)

[0898] MS (MALDI-TOF): m / z 501.21 [M+]

[0899] Synthesis Example 14. Synthesis of Compound 251

[0900] Synthesis Example 14-1. Synthesis of <Intermediate 14-a>

[0901]

[0902] <Intermediate 14-a>

[0903] 9-bromo-10-phenyl(D5)-anthracene (33.1 g, 98 mmol), (4-bromophenyl)boronic acid (23.5 g, 117 mmol), palladium acetate (0.4 g, 2 mmol), potassium carbonate (27 g, 195 mmol), and Sphos (1.6 g, 4 mmol) were added to a 500 mL reactor, followed by 200 mL of toluene, 90 mL of ethanol, and 60 mL of water. The reactor temperature was raised to 90 °C and stirred overnight. Upon completion of the reaction, the reactor temperature was lowered to room temperature, extracted with methanol, and the organic layer was separated. The organic layer was concentrated under reduced pressure, separated by column chromatography, and recrystallized with toluene and acetone to obtain <Intermediate 14-a> (11.9 g, 32%).

[0904] Synthesis Example 14-2. Synthesis of <Compound 251>

[0905]

[0906] <Compound 251>

[0907] In Synthesis Example 1 above, <Compound 251> was obtained by the same method using <Intermediate 14-a> instead of 9-bromo-10-phenyl-anthracene and 1-brovo-dibenzofuran instead of 7-phenyl-1-dibenzofuranyl-boronic acid. (Yield 50%)

[0908] MS (MALDI-TOF): m / z 501.21[M+]

[0909] Examples 1 to 20: Preparation of organic light-emitting diodes

[0910] 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 adjusting the torr, HAT-CN was deposited on the ITO to a thickness of 70 nm as a hole injection layer, and NPD was deposited to a thickness of 30 nm as a hole transport layer. As a host for the emissive layer, the compound listed in Table 1 below was deposited to a thickness of 25 nm at a weight ratio (wt%) of 7:3. While depositing the emissive layer, [BD] was used as a dopant at 2 wt% relative to 100% of the host weight. Subsequently, [Formula E-1] was deposited to a thickness of 30 nm as an electron transport layer, and [Formula E-2] was deposited to a thickness of 1 nm as an electron injection layer. Al was deposited to a thickness of 100 nm to form the cathode. The luminescence characteristics of the organic light-emitting device were measured at 0.4 mA.

[0911] [HAT-CN] [NPD] [BD]

[0912]

[0913] [Chemical Formula E-1] [Chemical Formula E-2]

[0914]

[0915] Comparative Examples 1 to 5

[0916] The experiment was conducted by fabricating the same method except that the compound listed in Table 1 below was used instead of the compound according to the present invention used as the host in the above example, and the luminescence characteristics of the organic light-emitting diode were measured at 0.4 mA.

[0917] [Chemical Formula A] [Chemical Formula B]

[0918]

[0919] Host No. 1 2nd host Voltage (V) EQE Lifespan (T97) Example 1 Compound 184 Compound 2 3.5 12.2 318 Example 2 Compound 184 Compound 193 3.4 12.6 330 Example 3 Compound 184 Compound 251 3.5 12.4 306 Example 4 Compound 185 Compound 8 3.6 11.8 291 Example 5 Compound 185 Compound 79 3.5 12.4 288 Example 6 Compound 193 Compound 60 3.6 12.5 314 Example 7 Compound 193 Compound 65 3.6 11.6 309 Example 8 Compound 195 Compound 61 3.5 11.5 294 Example 9 Compound 195 Compound 2 3.5 11.8 292 Example 10 Compound 198 Compound 251 3.5 11.8 276 Example 11 Compound 198 Compound 8 3.5 11.5 286 Example 12 Compound 217 Compound 79 3.6 11.3 294 Example 13 Compound 217 Compound 60 3.6 12.3 288 Example 14 Compound 237 Compound 65 3.5 12.5 300 Example 15 Compound 237 Compound 2 3.6 12.4 310 Example 16 Compound 60 Compound 65 3.5 11.9 305 Example 17 Compound 60 Compound 185 3.6 12.0 296 Example 18 Compound 65 Compound 195 3.5 11.8 313 Example 19 Compound 65 Compound 217 3.6 12.0 308 Example 20 Compound 251 Compound 61 3.6 11.4 310 Comparative Example 1 Compound 2 3.7 10.0 202 Comparative Example 2 Chemical formula A 3.9 8.2 190 Comparative Example 3 Chemical formula B 4.0 7.9 184 Comparative Example 4 Compound 198 Chemical formula A 3.8 9.8 220 Comparative Example 5 Chemical formula A Chemical formula B 3.8 8.8 200

[0920] As shown in [Table 1] above, the organic light-emitting device with a light-emitting layer prepared using two types of anthracene compounds according to the present invention was found to have evenly good characteristics of low voltage, long lifespan, and high efficiency compared to a compound using only one anthracene compound, 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 a light-emitting layer interposed between the first electrode and the second electrode; wherein the light-emitting layer comprises a host and a dopant, and the host comprises one or more compounds represented by [Chemical Formula A] below, and also comprises one or more compounds represented by [Chemical Formula A-1] below, wherein the compound represented by [Chemical Formula A] and the compound represented by [Chemical Formula A-1] are different from each other. [Chemical Formula A] In the above [Chemical Formula A], the substituents R1 to R 16 Each is identical or different and 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 C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to C30 arylsilyl group, a cyano group, and a halogen group, wherein R9 to R 16 One of them is a single bond bonded to the linker L, the substituent Ar1 is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, the linker L is any one selected from a single bond and a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, n is any integer from 1 to 3, and if n is 2 or more, each linker L is identical or different from each other, and X is O or S, [Chemical Formula A-1] In the above chemical formula A-1, the above R1 to R 15 , L, n, and X are each the same as defined in the above Chemical Formula A, substituent Ar1 is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and substituents R9 to R in the above [Chemical Formula A-1] 15 At least one of the substituents is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and in [Chemical Formula A] and [Chemical Formula A-1], 'substituted' in 'substituted or unsubstituted' means being substituted with one or more substituents 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 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms, and arylsilyl group having 6 to 24 carbon atoms, provided that the compound represented by [Chemical Formula A]; and the compound represented by [Chemical Formula A-1]; Each contains at least one deuterium. Claim 2 An organic light-emitting diode according to claim 1, characterized in that the substituents R1 to R8 in [Chemical Formula A] are each the same or different and are independently hydrogen or deuterium. Claim 3 delete Claim 4 An organic light-emitting device according to claim 1, wherein the substituent Ar1 in [Chemical Formula A] is selected from any one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted fluorenyl group. Claim 5 An organic light-emitting device according to claim 1, characterized in that the linker L in [Chemical Formula A] and [Chemical Formula A-1] is a single bond, or a substituted or unsubstituted arylene group having 6 to 18 carbon atoms. Claim 6 An organic light-emitting diode according to claim 5, characterized in that the linker L in [Chemical Formula A] is a single bond or is selected from any one of [Structural Formula 21] to [Structural Formula 27] below. [Structural Formula 21] [Structural Formula 22] [Structural Formula 23] [Structural Formula 24] [Structural Formula 25] [Structural Formula 26] [Structural Formula 27] In the above linker L, the carbon site of the aromatic ring can be bonded to hydrogen or deuterium. Claim 7 delete Claim 8 delete Claim 9 An organic light-emitting diode according to claim 1, characterized in that the host comprises only a compound represented by [Chemical Formula A] and a compound represented by [Chemical Formula A-1]. Claim 10 delete Claim 11 An organic light-emitting diode according to claim 1, wherein the compound represented by [Chemical Formula A] in the host is a compound represented by [Chemical Formula A-1] or a compound represented by [Chemical Formula A-2] below, and the host comprises at least one compound represented by [Chemical Formula A-1] and at least one compound selected from [Chemical Formula A-1] and [Chemical Formula A-2], wherein each of these is different from one another. [Chemical Formula A-2] R1 to R in the above chemical formula A-2 15 , Ar1, L, n, and X are each the same as defined in Paragraph 1. Claim 12 An organic light-emitting diode according to claim 11, wherein the host comprises only one compound represented by [Chemical Formula A-1] and one compound represented by [Chemical Formula A-2], and wherein these are different from each other. Claim 13 An organic light-emitting diode according to claim 1, characterized in that each of the substituents R1 to R8 in [Chemical Formula A-1] is either identical or different and is independently hydrogen or deuterium. Claim 14 An organic light-emitting diode according to claim 1, characterized in that the substituent Ar1 in [Chemical Formula A-1] is a deuterium-substituted or unsubstituted phenyl group. Claim 15 An organic light-emitting diode according to claim 1, characterized in that the linker L in [Chemical Formula A-1] is a single bond or is selected from any one of [Structural Formula 21] to [Structural Formula 27] below. [Structural Formula 21] [Structural Formula 22] [Structural Formula 23] [Structural Formula 24] [Structural Formula 25] [Structural Formula 26] [Structural Formula 27] In the above linker L, the carbon site of the aromatic ring can be bonded to hydrogen or deuterium. Claim 16 delete Claim 17 In claim 1, the compound represented by [Chemical Formula A] is the following <Compound 3>, <Compound 4>, <Compounds 7> to <Compound 9>, <Compounds 58> to <Compound 79>, <Compound 119>, <Compound 120>, <Compounds 124> to <Compounds 126>, <Compound 128>, <Compounds 130> to <Compound 132>, <Compounds 151> to <Compound 159>, <Compound 163>, <Compound 171>, <Compound 175> to <Compound 180>, <Compound 184> to <Compound 213>, <Compounds 215> to <Compounds 217>, <Compound 226> to An organic light-emitting diode characterized by being any one selected from <Compound 240>, <Compound 242>, <Compound 245> to <Compound 249>, <Compound 251>, <Compound 256> to <Compound 258>, <Compound 262> to <Compound 264>, <Compound 268> to <Compound 273>, <Compound 277> to <Compound 282>, <Compound 289> to <Compound 291>, <Compound 295> to <Compound 309>. <Compound 3> <Compound 4> <Compound 7><Compound 8><Compound 9> <Compound 58> <Compound 59> <Compound 60> <Compound 61> <Compound 62> <Compound 63> <Compound 64> <Compound 65> <Compound 66> <Compound 67> <Compound 68> <Compound 69> <Compound 70> <Compound 71> <Compound 72> <Compound 73> <Compound 74> <Compound 75> <Compound 76> <Compound 77> <Compound 78> <Compound 79> <Compound 119> <Compound 120> <Compound 124> <Compound 125> <Compound 126> <화합물 128> <화합물 130> <화합물 131> <화합물 132> <화합물 151> <화합물 152> <화합물 153> <화합물 154> <화합물 155> <화합물 156> <화합물 157> <화합물 158> <화합물 159> <화합물 163> <화합물 171> <화합물 175> <화합물 176> <화합물 177> <화합물 178> <화합물 179> <화합물 180> <화합물 184> <화합물 185> <화합물 186> <화합물 187> <화합물 188> <화합물 189> <화합물 190> <화합물 191> <화합물 192> <화합물 193> <화합물 194> <화합물 195> <화합물 196> <화합물 197> <화합물 198> <화합물 199> <화합물 200> <화합물 201> <화합물 202> <화합물 203> <화합물 204> <화합물 205> <화합물 206> <화합물 207> <화합물 208> <화합물 209> <화합물 210> <화합물 211> <화합물 212> <화합물 213> <화합물 215> <화합물 216> <화합물 217> <화합물 226> <화합물 227> <화합물 228> <화합물 229> <화합물 230> <화합물 231> <화합물 232> <화합물 233> <화합물 234> <화합물 235> <화합물 236> <화합물 237> <화합물 238> <화합물 239> <화합물 240> <화합물 242> <화합물 245> <화합물 246> <화합물 247> <화합물 248> <화합물 249> <화합물 251> <화합물 256><화합물 257><화합물 258> <화합물 262><화합물 263><화합물 264> <화합물 268><화합물 269><화합물 270> <화합물 271><화합물 272><화합물 273> <화합물 277><화합물 278><화합물 279> <화합물 280><화합물 281><화합물 282> <화합물 289><화합물 290><화합물 291> <화합물 295><화합물 296><화합물 297> <화합물 298><화합물 299><화합물 300> <화합물 301><화합물 302><화합물 303> <화합물 304><화합물 305><화합물 306> <화합물 307><화합물 308><화합물 309> Claim 18 An organic light-emitting diode according to claim 1, wherein the dopant comprises a compound represented by any one of the following [Chemical Formula D1] to [Chemical Formula D8]. [Chemical Formula D1] [Chemical Formula D2] In the above [Chemical Formula D1] and [Chemical Formula D2], the above A 31 , A 32 , E1 and F1 are each identical or different and independently substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms, or substituted or unsubstituted aromatic heterocycles having 2 to 40 carbon atoms; and the above A 31 Two adjacent carbon atoms within the aromatic ring of, and the above A 32 Two adjacent carbon atoms within the aromatic ring are the substituent R 51 and R 52 Each forms a condensation ring by forming a five-membered ring with a carbon atom connected to; the above linker L 21 to L 32 is each identical or different and independently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; and W and W' are each identical or different and independently selected from NR 53 , CR 54 R 55 , SiR 56 R 57 , GeR 58 R 59 It is any one selected from , O, S, and Se; and the above substituent R 51 to R 59 , Ar 21 or Ar 28 Each is identical or different and 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 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, and a substituted or unsubstituted alkoxy group having 5 to 30 carbon atoms. Any one selected from an arylthioxy group, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 30 carbon atoms, a substituted or unsubstituted arylgermanium group having 1 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group, wherein R 51 and R 52 They can be connected to each other to form alicyclic or aromatic single or polycyclic rings, and the carbon atoms of the formed alicyclic or aromatic single or polycyclic rings can be substituted with one or more heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te; and p11 to p14, r11 to r14, and s11 to s14 are each integers from 1 to 3, wherein each of these is 2 or more, each linker L 21 to L 32 are identical or different from each other, and the above x1 is 1, and y1, z1, and z2 are each identical or different and are independent integers from 0 to 1, and the above Ar 21 and Ar 22 , Ar 23 and Ar 24 , Ar 25 Wa Ar 26 and Ar 27 and Ar 28 Each can be connected to others to form a ring; and in the above chemical formula D1, A 32 Two adjacent carbon atoms within the ring are represented by the above structural formula Q 11 It forms a condensation ring by combining with * of, and in the above chemical formula D2, the above A 31 Two adjacent carbon atoms within the ring are represented by the above structural formula Q 12 It forms a condensation ring by combining with * of, and the above A 32 Two adjacent carbon atoms within the ring are represented by the above structural formula Q 11 It can form a condensation ring by combining with *.[Chemical Formula D3] In the above [Chemical Formula D3], X1 is any one selected from B, P, and P=O, and T1 to T3 are each identical or different from one another and are independently substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms, or substituted or unsubstituted aromatic heterocycles having 2 to 40 carbon atoms; and Y1 is NR 61 , CR 62 R 63 , O, S, SiR 64 R 65 It is any one selected from among; and the above Y2 is NR 66 , CR 66 R 68 , O, S, SiR 69 R 70 It is any one selected from among the above R 61 to R 70 Each is identical or different from one another and independently 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 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 C1 to C30 alkylamine group, a substituted or unsubstituted C5 to C30 arylamine group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C5 to C30 alkylsilyl group, a substituted or unsubstituted C5 to C30 alkylthioxy group It is any one selected from an arylsilyl group, a cyano group, and a halogen group, and the above R 61 to R 70 Each may additionally form a monocyclic or polycyclic ring of alicyclic or aromatic by combining with one or more rings selected from T1 to T3. [Chemical Formula D4] [Chemical Formula D5] In the above [Chemical Formula D4] and [Chemical Formula D5], X2 is any one selected from B, P, and P=O, T4 to T6 are identical to T1 to T3 in [Chemical Formula D3], and Y4 is NR 61 , CR 62 R 63 , O, S, SiR 64 R 65 It is any one selected from among; the above Y5 is NR 66 , CR 66 R 68 , O, S, SiR 69 R 70 It is any one selected from among them, and the above Y6 is NR 71 , CR 72 R 73 , O, S, SiR 74 R 75 It is any one selected from among the above R 61 to R 75 The above R in [Chemical Formula D3] 61 to R 70 It is identical to. [Chemical Formula D6] [Chemical Formula D7] [Chemical Formula D8] In the above [Formula D6] to [Formula D8], X is selected from B, P, and P=O, Q1 to Q3 are each identical to T1 to T3 in [Formula D3], the linker Y is selected from N-R3, CR4R5, O, S, and Se, and the substituents R3 to R5 are each R in [Formula D3]. 61 to R 70 Same as, wherein R3 to R5 can each be combined with the Q2 ring or Q3 ring to additionally form a monocyclic or polycyclic ring of alicyclic or aromatic, and R4 and R5 can each be connected to each other to additionally form a monocyclic or polycyclic ring of alicyclic or aromatic, and the ring formed by Cy1 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, excluding a nitrogen (N) atom, an aromatic carbon atom in the Q1 ring to which the nitrogen (N) atom is bonded, and an aromatic carbon atom in the Q1 ring to be bonded to Cy1, and in the formula D7, 'Cy2' can be added to Cy1 to form a saturated hydrocarbon ring, and the ring formed by Cy2 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, excluding a carbon atom included in Cy1, and in the formula D8, the ring formed by Cy3 is to be bonded to Cy3 Except for the aromatic carbon atom in the Q3 ring, the aromatic carbon atom in Q3 to be bonded to the nitrogen (N) atom, the nitrogen (N) atom, and the carbon atom in Cy1 to which the nitrogen (N) atom is bonded, it is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, and the 'substituted' in 'substituted or unsubstituted' in [Chemical Formula D1] to [Chemical Formula D8] 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, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, and carbon atoms having 7 to 24 alkylaryl groups, 2 to 24 carbon atoms heteroaryl groups, 2 to 24 carbon atoms heteroarylalkyl groups, 1 to 24 carbon atoms alkoxy groups, 1 to 24 carbon atoms alkylamino groups, 12 to 24 carbon atoms diarylamino groups, 2 to 24 carbon atoms diheteroarylamino groups, 7 to 24 carbon atoms aryl(heteroaryl)amino groups,It means being substituted with one or more substituents selected from the group consisting of an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and an arylthionyl group having 6 to 24 carbon atoms, and as a more preferred example, this includes deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a heteroalkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms, and a group having 2 to 18 carbon atoms. It means being substituted with one or more substituents selected from the group consisting of a heteroaryl group, a heteroarylalkyl group having 2 to 18 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, a diarylamino group having 12 to 18 carbon atoms, a diheterorylamino group having 2 to 18 carbon atoms, an aryl(heteroaryl)amino group having 7 to 18 carbon atoms, an alkylsilyl group having 1 to 12 carbon atoms, an arylsilyl group having 6 to 18 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, and an arylthionyl group having 6 to 18 carbon atoms. Claim 19 An organic light-emitting device according to claim 1, wherein the compound represented by [Chemical Formula A] and the compound represented by [Chemical Formula A-1] have a molecular weight difference of 300 or less. Claim 20 An organic light-emitting device according to claim 1, wherein the organic layer comprises at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a capping layer. Claim 21 An organic light-emitting device according to claim 18, characterized in that one or more layers selected from each of the above layers are formed by a deposition process or a solution process. Claim 22 An organic light-emitting element according to claim 1, characterized in that the organic light-emitting element is used in any one selected from a flat panel display device; a flexible display device; a monochromatic or white flat panel lighting device; and a monochromatic or white flexible lighting device.

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