Auxiliary electron transport layer material and organic electroluminescent element comprising same

Abstract

The present invention provides: auxiliary electron transport layer material disposed between a light-emitting layer and electron transport layer of an organic electroluminescent device, and comprising a homogeneous mixture containing at least two types of organic compounds; and an organic electroluminescent device having, by comprising said material, optimized driving voltage, light-emission efficiency, and lifespan property.

Description

Electron transport auxiliary layer material and organic electroluminescent device including the same

[0001] The present invention relates to an electron transport auxiliary layer material disposed between the light-emitting layer and the electron transport layer of an organic electroluminescent device and composed of a homogeneous mixture comprising at least two types of organic compounds, and an organic electroluminescent device comprising the same in which the driving voltage, luminous efficiency, and lifespan characteristics of the device are optimized.

[0002]

[0003] Research on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') continued following the blue electroluminescence using anthracene single crystals in 1965. In 1987, Tang proposed an organic EL device with a two-layer stacked structure consisting of a hole layer (NPB) and an emissive layer (Alq3). Subsequently, to achieve the high efficiency and long lifespan characteristics required for commercialization, multilayer stacked structures were proposed that assigned distinct and specialized functions within the device, such as an organic layer responsible for hole injection and transport, an organic layer responsible for electron injection and transport, and an organic layer that induces electroluminescence through the combination of holes and electrons. The introduction of multilayer stacked structures has improved the performance of organic EL devices to commercialization levels, and starting with automotive radio display products in 1997, there is an effort to expand their scope of application to portable information display devices and TV display devices.

[0004] The demand for larger and higher resolution displays presents the challenge of increasing the efficiency and lifespan of organic EL devices. In particular, achieving higher resolution by forming more pixels within the same area results in a reduction in the light-emitting area of ​​organic EL pixels, which inevitably leads to a decrease in lifespan and has become the most critical technical challenge that organic EL devices must overcome.

[0005] When current or voltage is applied to two electrodes of an organic EL device, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, excitons are formed, and these excitons fall to the ground state to emit light. At this time, depending on the type of electron spin of the formed excitons, organic EL devices can be classified into fluorescent EL devices in which singlet excitons contribute to light emission and phosphorescent EL devices in which triplet excitons contribute to light emission.

[0006] The electron spins of excitons formed by the recombination of electrons and holes are generated in singlet excitons and triplet excitons at a ratio of 25% and 75%, respectively. For fluorescent EL devices that emit light through singlet excitons, the internal quantum efficiency theoretically cannot exceed 25% depending on the generation ratio, and the external quantum efficiency is accepted to be limited to 5%. For phosphorescent EL devices that emit light through triplet excitons, the luminescence efficiency can be improved by up to four times compared to fluorescence when metal complex compounds containing transition metal heavy atoms such as Ir and Pt are used as phosphorescent dopants.

[0007] As mentioned above, based on theoretical facts, phosphorescent EL devices exhibit higher efficiency than fluorescence in terms of luminous efficiency. However, regarding blue phosphorescent devices excluding green and red, the level of development for deep blue color purity, high-efficiency phosphorescent dopants, and hosts with a wide energy gap that satisfy these requirements is insufficient, so blue phosphorescent devices have not yet been commercialized and blue fluorescent devices are being used in products.

[0008] Research results have been reported to increase the stability of the device by preventing holes from diffusing into the electron transport layer in order to improve the characteristics of the aforementioned organic EL device. However, satisfactory results have not been obtained to date.

[0009]

[0010] The present invention has been devised to solve the aforementioned problems, and its technical objective is to provide an organic electroluminescent device that simultaneously exhibits high efficiency, low voltage, and long lifespan by including an electron transport auxiliary layer material comprising at least two types of organic compounds having a predetermined moiety and an electron transport auxiliary layer material disposed between a light-emitting layer and an electron transport region.

[0011] Other objects and advantages of the present invention may be more clearly explained by the following detailed description of the invention and claims.

[0012]

[0013] To achieve the above-mentioned technical problem, the present invention provides an electron transport auxiliary layer material disposed between a light-emitting layer and an electron transport layer of an organic electroluminescent device, wherein the electron transport auxiliary layer material comprises at least one first organic compound and at least one second organic compound, wherein the first organic compound is represented by the following chemical formula 1 and the second organic compound is represented by the following chemical formula 2.

[0014] [Chemical Formula 1]

[0015]

[0016] In the above chemical formula 1,

[0017] Ar1 to Ar3 are identical or different from one another, and each independently contains hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, C1 to C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is selected from the group consisting of arylamines, or they can combine with any adjacent group to form a condensation ring,

[0018] However, at least one of Ar1 to Ar3 is C6~C 60 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei,

[0019] R1 and R2 are identical or different from each other, and each independently consists of hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, and C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is selected from the group consisting of arylamines, or they can combine with any adjacent group to form a condensation ring,

[0020] o and p are each independently integers from 0 to 3, and

[0021] The alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkyloxy groups, aryloxy groups, alkylsilyl groups, arylsilyl groups, alkylboron groups, arylboron groups, alkylphosphine oxide groups, arylphosphine groups, arylphosphine oxide groups, arylamine groups, and condensation rings of the above Ar1 to Ar3 and R1 to R2 are each independently deuterium, halogen, cyano groups, nitro groups, C2 to C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C1~C 40 alkyl group of, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, and if there are multiple substituents, they are identical or different from each other.

[0022] [Chemical Formula 2]

[0023]

[0024] In the above chemical formula 2,

[0025] Multiple Xs are identical or different from one another, and each independently N or C(R 10 ) and, however, at least one of the multiple X is N,

[0026] R 10It consists of hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is selected from the group consisting of arylamines, or they may combine with any adjacent group to form a condensation ring, and the R 10 In this case of multiple individuals, multiple Rs 10 They are identical or different from each other,

[0027] L is a single bond, or C6~C 18 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclei,

[0028] n is an integer from 0 to 3, and

[0029] Ar4 consists of hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is selected from the group consisting of arylamines, or they can combine with any adjacent group to form a condensation ring,

[0030] The arylene group and heteroarylene group of the above L, and the above R 10 and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, alkylphosphine oxide group, arylphosphine group, arylphosphine oxide group, arylamine group, and condensation ring of Ar4 are each independently deuterium, halogen, cyano group, nitro group, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C1~C 40 alkyl group of, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, and if there are multiple substituents, they are identical or different from each other.

[0031] For example, in one embodiment according to the present invention, the HOMO energy level of the first organic compound may be -5.0 eV or less.

[0032] For example, in one embodiment according to the present invention, the LUMO energy level of the second organic compound may be -3.0 eV or higher.

[0033] For example, in one embodiment according to the present invention, the electron transport auxiliary layer material may be composed of a homogeneous mixture of a first organic compound and a second organic compound that are different from each other.

[0034] For example, in one embodiment according to the present invention, the electron transport auxiliary layer material may not contain metal.

[0035] For example, in one embodiment according to the present invention, the singlet (S1) energy of the homogeneous mixture constituting the electron transport assisting layer material may be 3.0 eV or less.

[0036] For example, in one embodiment according to the present invention, the maximum emission wavelength of the homogeneous mixture may be formed in a longer wavelength region than the maximum emission wavelength of the first organic compound, the second organic compound, and the simple organic mixture of the first organic compound and the second organic compound.

[0037] In addition, the present invention provides an organic electroluminescent device having a structure in which a first electrode; a hole transport region; a light-emitting layer; an electron transport region; and a second electrode are sequentially stacked, wherein the organic electroluminescent device comprises an electron transport auxiliary layer disposed between the light-emitting layer and the electron transport region, and wherein the electron transport auxiliary layer comprises the aforementioned electron transport auxiliary layer material.

[0038] For example, in one embodiment according to the present invention, the electron transport auxiliary layer may be formed by depositing an electron transport auxiliary layer material through a single deposition source.

[0039] For example, in one embodiment according to the present invention, the electron transport auxiliary layer material may be composed of a solid-phase homogeneous mixture.

[0040] For example, in one embodiment according to the present invention, the light-emitting layer comprises at least one host, and at least one host of an adjacent light-emitting layer; and at least one of a first organic compound and a second organic compound of an electron transport assisting layer may be different from each other.

[0041] In one embodiment according to the present invention, the electron transport region includes an electron transport layer, and the material of the adjacent electron transport layer; and at least one of the first organic compound and the second organic compound of the electron transport auxiliary layer may be different from each other.

[0042] For example, in one embodiment according to the present invention, the electron transport region may include at least one of an electron transport layer and an electron injection layer.

[0043] For example, in one embodiment according to the present invention, the hole transport region may include at least one of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer.

[0044] For example, in one embodiment according to the present invention, the organic electroluminescent device may have a plurality of light-emitting layer stacks, each including at least one light-emitting layer.

[0045]

[0046] According to one embodiment of the present invention, by including at least two types of organic compounds having a predetermined moiety as an electron transport auxiliary layer disposed between the light-emitting layer and the electron transport region, the hole and electron barrier performance due to the physical properties of each organic compound material is improved while performing the role of a conventional triplet (T1) barrier, thereby providing an organic electroluminescent device with optimized driving voltage, luminous efficiency, and lifetime characteristics.

[0047] The effects according to the present invention are not limited to those exemplified above, and a wider variety of effects are included in this specification.

[0048]

[0049] FIG. 1 is a cross-sectional view showing the structure of an organic electroluminescent device according to one embodiment of the present invention.

[0050] <Explanation of Symbols>

[0051] 100: Organic electroluminescent device

[0052] A: Organic layer

[0053] 10: First electrode

[0054] 20: Second electrode

[0055] 30: Precision Transport Area

[0056] 31: Hole injection layer

[0057] 32: Precision Transport Layer

[0058] 40: Emissive layer

[0059] 50: Electronic transport area

[0060] 53: Electron transport auxiliary layer

[0061] 52: Electron transport layer

[0062] 51: Electron injection layer

[0063]

[0064] The advantages and features of the present invention and the methods for achieving them will become clear by referring to the embodiments described below in detail together with the accompanying drawings. However, the present invention is not limited to the embodiments disclosed below but may be implemented in various different forms. These embodiments are provided merely to ensure that the disclosure of the present invention is complete and to fully inform those skilled in the art of the scope of the invention, and the present invention is defined only by the scope of the claims. Accordingly, in some embodiments, well-known process steps, well-known device structures, and well-known techniques are not specifically described to avoid the present invention being interpreted ambiguously. Throughout the specification, like reference numerals refer to like components.

[0065] Unless otherwise defined, all terms used in this specification (including technical and scientific terms) may be used in a meaning that is commonly understood by those skilled in the art to which the present invention pertains. Additionally, terms defined in commonly used dictionaries are not to be interpreted ideally or excessively unless explicitly and specifically defined otherwise.

[0066] Furthermore, throughout the specification, when a part is described as "comprising" 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 terms "above" or "on" mean not only cases where a part is located above or below the subject part but also cases where another part is located in between, and do not necessarily mean that it is located above based on the direction of gravity. Furthermore, in this specification, terms such as "first," "second," etc., are used to distinguish components from one another, rather than indicating an arbitrary order or importance.

[0067] In this specification, "number of nuclei" refers to the number of ring atoms constituting a ring structure, wherein the nuclei may be carbon or heteroatoms selected from the group consisting of N, O, S, and Se. For example, the number of nuclei of pyridine refers to 6, including 5 C and 1 N constituting the pyridine ring.

[0068] In the present invention, "alkyl" refers to a monovalent substituent derived from a straight-chain or side-chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

[0069] In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

[0070] In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0071] In the present invention, "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0072] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclei, wherein one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Examples of such heterocycloalkyls include, but are not limited to, morpholine and piperazine.

[0073] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, consisting of a single ring or a combination of two or more rings. Additionally, forms in which two or more rings are simply pendent or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0074] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclei. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Additionally, forms in which two or more rings are simply pendent or condensed with each other may be included, and furthermore, forms condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl.

[0075] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' represents an alkyl group having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0076] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, where R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

[0077] In the present invention, "alkylsilyl" refers to a silyl substituted with an alkyl group having 1 to 40 carbon atoms, and includes not only mono- but also di- and tri-alkylsilyls. Additionally, "arylsilyl" refers to a silyl substituted with an aryl group having 5 to 60 carbon atoms, and includes not only mono- but also polyarylsilyls such as di- and tri-arylsilyls.

[0078] In the present invention, "alkylboron group" means a boron group substituted with an alkyl group having 1 to 40 carbon atoms, and "arylboron group" means a boron group substituted with an aryl group having 6 to 60 carbon atoms.

[0079] In the present invention, "alkylphosphinyl group" refers to a phosphine group substituted with an alkyl group having 1 to 40 carbon atoms, and includes not only mono- but also di-alkylphosphinyl groups. In addition, in the present invention, "arylphosphinyl group" refers to a phosphine group substituted with a monoaryl or diaryl group having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphinyl groups.

[0080] In the present invention, "arylamine" refers to an amine substituted with an aryl group having 6 to 60 carbon atoms, and includes not only mono- but also di-arylamines.

[0081] In the present invention, "heteroarylamine" refers to an amine substituted with a heteroaryl having 5 to 60 nuclei, and includes not only mono- but also di-heteroarylamines.

[0082] In the present invention, (aryl)(heteroaryl)amine refers to an amine substituted with an aryl having 6 to 60 carbon atoms and a heteroaryl having 5 to 60 nuclei.

[0083] In the present invention, "condensed ring or condensed ring" means a condensed aliphatic ring having 3 to 40 carbon atoms, a condensed aromatic ring having 6 to 60 carbon atoms, a condensed heteroaliphatic ring having 3 to 60 nuclei, a condensed heteroaromatic ring having 5 to 60 nuclei, a spiro ring having 3 to 60 carbon atoms, or a combination thereof.

[0084]

[0085] Electron Transport Auxiliary Layer Material

[0086] One example of the present invention is a material for an organic layer provided in an organic electroluminescent device, specifically an electron transport auxiliary layer disposed between a light-emitting layer and an electron transport layer.

[0087] The electron transport auxiliary layer is positioned between the emissive layer and the electron transport region of an organic electroluminescent device, and simultaneously performs the role of more efficiently transferring electrons from the electron transport region, such as the electron transport layer, to the emissive layer, while trapping excitons generated within the emissive layer, and preventing excess holes within the emissive layer from being transferred to the electron transport region, such as the electron transport layer.

[0088] In order to improve the performance and lifespan characteristics of a device by not only increasing the luminescence efficiency in the light-emitting layer but also simultaneously preventing hole leakage from the light-emitting layer to the electron transport region and electron leakage from the light-emitting layer to the hole transport region, at least two types of organic compounds having a predetermined moiety (e.g., EDG, EWG), such as the aforementioned first organic compound and second organic compound, are combined and used as essential components of an electron transport auxiliary layer.

[0089] In particular, the present invention necessarily includes a first organic compound and a second organic compound having a predetermined moiety (EDG, EWG) as an electron transport auxiliary layer material, and by adjusting the content ratio of these to a predetermined range, it is intended to function as an electron transport auxiliary layer suitable for charge balance within the device. Furthermore, by mixing the first organic compound and the second organic compound, it can perform the role of a blocking layer by utilizing a wide range of HOMO energy levels and LUMO energy levels. In addition, by utilizing the new energy levels generated by mixing the two types of organic compounds mentioned above, it is expected to serve as an energy barrier.

[0090] The electron transport auxiliary layer material according to the present invention comprises at least one first organic compound and at least one second organic compound that are different from each other, and does not include conventional metal or organometallic compounds known in the art.

[0091] Specifically, the first organic compound may be used without limitation as a hole-transporting organic compound having a stronger hole-transporting characteristic than the second organic compound, for example, containing at least one conventional electron-donating group (EDG) moiety known in the art. Additionally, the second organic compound may be used without limitation as an electron-transporting compound having a stronger electron-transporting characteristic than the first organic compound, for example, containing at least one conventional electron-withdrawing group (EWG) moiety known in the art.

[0092] For example, the first organic compound can be represented by the following chemical formula 1, and the second organic compound can be represented by the following chemical formula 2.

[0093] [Chemical Formula 1]

[0094]

[0095] In the above chemical formula 1,

[0096] Ar1 to Ar3 are identical or different from one another, and each independently contains hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, C1 to C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is selected from the group consisting of arylamines, or they can combine with any adjacent group to form a condensation ring,

[0097] However, at least one of Ar1 to Ar3 is C6~C 60 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei,

[0098] R1 and R2 are identical or different from each other, and each independently consists of hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, and C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is selected from the group consisting of arylamines, or they can combine with any adjacent group to form a condensation ring,

[0099] o and p are each independently integers from 0 to 3, and

[0100] In the above Chemical Formula 1, the alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkyloxy groups, aryloxy groups, alkylsilyl groups, arylsilyl groups, alkylboron groups, arylboron groups, alkylphosphine oxide groups, arylphosphine groups, arylphosphine oxide groups, arylamine groups, and condensation rings of Ar1 to Ar3 and R1 to R2 are each independently deuterium, halogen, cyano groups, nitro groups, C2 to C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C1~C 40 alkyl group of, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, and if there are multiple substituents, they are identical or different from each other.

[0101] [Chemical Formula 2]

[0102]

[0103] In the above chemical formula 2,

[0104] Multiple Xs are identical or different from one another, and each independently N or C(R 10 ) and, provided that at least one of the multiple Xs is N, and any of the remaining Xs is -(L) n -Connected to Ar4,

[0105] R 10It consists of hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is selected from the group consisting of arylamines, or they may combine with any adjacent group to form a condensation ring, and the R 10 In this case of multiple individuals, multiple Rs 10 They are identical or different from each other,

[0106] L is a single bond, or C6~C 18 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclei,

[0107] n is an integer from 0 to 3, and

[0108] Ar4 consists of hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is selected from the group consisting of arylamines, or they can combine with any adjacent group to form a condensation ring,

[0109] In the above chemical formula 2, the arylene group and heteroarylene group of L, and the R 10 and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, alkylphosphine oxide group, arylphosphine group, arylphosphine oxide group, arylamine group, and condensation ring of Ar4 are each independently deuterium, halogen, cyano group, nitro group, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C1~C 40 alkyl group of, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, and if there are multiple substituents, they are identical or different from each other.

[0110] According to one embodiment of the present invention, in Formula 1, Ar1 to Ar3 are identical or different from one another, and each independently hydrogen, deuterium (D), C1 to C 40 alkyl group of, C6~C 60 an aryl group, a heteroaryl group having 5 to 60 nuclei, and C6~C 60 They are selected from the group consisting of arylamines, or they may form a condensation ring with an adjacent group, provided that at least one of Ar1 to Ar3 is C6 to C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei. Specifically, at least one of Ar1 to Ar3 is a carbazole group, and the remainder are C6 to C 60 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, wherein the carbazole group is excluded from the heteroaryl group defined as the remainder.

[0111] Also, R1 and R2 are identical or different from each other, and each independently consists of hydrogen, deuterium (D), halogen group, cyano group, nitro group, C1~C 40 alkyl group of, C6~C 60 an aryl group, a heteroaryl group having 5 to 60 nuclei, and C6~C 60 They are selected from the group consisting of arylamines, or they may combine with any adjacent group to form a condensation ring. Specifically, R1 and R2 are each independently hydrogen, deuterium (D), a halogen group, a cyano group, C1~C 40 alkyl group of, C6~C 60 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0112] o and p are each independently integers from 0 to 3. Here, if o and p are each 0, it means that R1 and R2 are each hydrogen, and if o and p are each integers from 1 to 3, it means that R1 and R2 are the aforementioned substituents excluding hydrogen.

[0113] For example, the first organic compound may be embodied in any one of the following chemical formulas 1A to 1B.

[0114] [Chemical Formula 1A]

[0115]

[0116] [Chemical Formula 1B]

[0117]

[0118] In the above chemical formulas 1A to 1B,

[0119] Y1 and Y2 are identical or different from each other, and each independently consists of hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, and C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60Selected from the group consisting of arylamines, provided that at least one of Y1 and Y2 is C6~C 60 It is Arilgi of, and

[0120] R3 to R6 are identical or different from one another, and each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is selected from the group consisting of arylamines, or they can combine with any adjacent group to form a condensation ring,

[0121] q and t are each independently integers from 0 to 4, and

[0122] r and s are each independently integers from 0 to 3, and

[0123] Ar1, Ar3, R1 to R2, o and p are each as defined in Chemical Formula 1.

[0124] To give a specific example of the above chemical formulas 1A to 1B, Y1 and Y2 may be identical or different from each other, and each independently hydrogen, deuterium (D), a halogen group, a cyano group, C1~C 40alkyl group of, C6~C 60 an aryl group, a heteroaryl group having 5 to 60 nuclei, and C6~C 60 Selected from the group consisting of arylamines, provided that at least one of Y1 and Y2 is C6~C 60 It is an aryl group. Specifically, Y1 and Y2 are each independently C6~C 40 It could be Arilgi.

[0125] R3 to R6 are identical or different from one another, and each independently consists of hydrogen, deuterium (D), halogen group, cyano group, nitro group, C1~C 40 alkyl group of, C6~C 60 an aryl group, a heteroaryl group having 5 to 60 nuclei, and C6~C 60 They are selected from the group consisting of arylamines, or they may combine with any adjacent group to form a condensation ring. Specifically, R3 and R6 are each independently hydrogen, deuterium (D), a halogen group, a cyano group, C1~C 40 alkyl group of, C6~C 60 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0126] q and t are each independently integers from 0 to 4, and r and s are each independently integers from 0 to 3. Here, if q to t are each 0, R3 to R6 are each hydrogen, and if q to t are each integers greater than or equal to 1, R3 to R6 are the aforementioned substituents excluding hydrogen.

[0127] The first organic compound represented by Formula 1 according to the present invention described above may be further embodied as a compound represented by any one of the following exemplary compounds, such as compounds C-1 to C-11. However, the first organic compound represented by Formula 1 of the present invention is not limited to those exemplified below.

[0128]

[0129] According to one embodiment of the present invention, in the formula 2, a plurality of Xs are identical or different from one another, and each independently N or C(R 10 ) and, provided that at least one of the multiple Xs is N, and any of the remaining Xs is -(L) n - It is connected to Ar4. Specifically, it is preferable that 1 to 3 of the plurality of X's are N.

[0130] R 10 Silver consists of hydrogen, deuterium (D), halogen, cyano group, C1~C 40 alkyl group, heterocycloalkyl group, C6~C 60 The aryl group of and heteroaryl groups having 5 to 60 nuclei may be selected from the group consisting of the aryl group and a heteroaryl group having 5 to 60 nuclei, or they may combine with any adjacent group to form a condensation ring, and the R 10 In this case of multiple individuals, multiple Rs 10 They are identical or different from each other. Specifically, R 10 Silver is hydrogen, C6~C 60 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0131] For example, the moiety containing multiple Xs in the above chemical formula 2 may be a conventional nitrogen-containing heteroaromatic ring moiety known in the art, and specifically may be embodied as any one of the electron-accepting (EWG) moiety represented by the following structural formula.

[0132]

[0133] In the above formula,

[0134] * represents the part connected to the above chemical formula 2, and

[0135] f is an integer from 0 to 3, and

[0136] R 10is as defined in Chemical Formula 2. Although not specifically indicated in the above structural formula, substituents known in the art, such as R excluding hydrogen, are 10 At least one substituent identical to the definition part of can be substituted. In addition, although only one part (*) connected to the second organic compound in the above structural formula is indicated, cases where two are included also fall within the scope of the present invention.

[0137] Also, L is a linker of a conventional divalent group known in the art, which is a single bond or C6~C 18 It may be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclei. Specifically, L is a single bond, or C6 to C 12 It may be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 12 nuclei. Specific examples of the arylene group linker and the heteroarylene group linker include a phenylene group, a biphenylene group, a naphthylene group, anthracenylene group, an indenylene group, a pyrantrenylene group, a carbazolilene group, a thiophenylene group, an indolylene group, a furinylene group, a quinolinylene group, a pyrrolylene group, an imidazolilene group, an oxazolilene group, a thiazolilene group, a pyridinylene group, a pyrimidinylene group, a dibenzofuran moiety, a dibenzothiophene moiety, and / or a dibenzoselenophenone moiety. More specifically, it is preferable that it be a phenylene group, a biphenylene group, or a terphenylene group.

[0138] Here, the number of linkers L, n, is an integer from 0 to 3. For example, when n is 0, it corresponds to a single bond (direct bond), and when n is 1 to 3, it may have substituents other than the single bond in the aforementioned linker definition part, and multiple L may be identical or different from each other.

[0139] For example, L can be a single bond or can be embodied as a linker selected in the following structural formula.

[0140]

[0141] In the above formula,

[0142] * indicates the part connected to the above chemical formula 2, and

[0143] R 21 It consists of hydrogen, deuterium (D), and C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroarylene group having 5 to 18 nuclei. In addition, although not indicated in the aforementioned structural formula, if L is not a single bond, a substituent known in the art, e.g., R excluding hydrogen, may be used. 10 At least one substituent identical to the definition part of can be substituted.

[0144] According to one embodiment of the present invention, Ar4 of Formula 2 comprises hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, or they may combine with any adjacent group to form a condensation ring. Specifically, Ar4 is C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0145] For example, the second organic compound can be embodied by the following chemical formula 3.

[0146] [Chemical Formula 3]

[0147]

[0148] In the above chemical formula 3,

[0149] Multiple Xs are identical or different from one another, and each independently N or C(R 10 ) and, however, at least one of the plurality of X is N. Specifically, it is preferable that 1 to 3 of the plurality of X are N.

[0150] Ar12 and Ar 13 They are identical or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C6~C 60 It may be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, or they may combine with any adjacent group to form a condensation ring. Specifically, Ar 12 and Ar 13 Each independently consists of deuterium (D), a halogen group, a cyano group, and C1~C 40 alkyl group of, C6~C 60 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0151] n is an integer from 0 to 3.

[0152] Y1 is O or S.

[0153] R 10 , R 11 , R 12 and R 15 are identical or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C6~C 60 The aryl group of and heteroaryl groups having 5 to 60 nuclei may be selected from the group consisting of the aryl group and a heteroaryl group having 5 to 60 nuclei, or they may combine with any adjacent group to form a condensation ring, and the R 11 , R 12 and R 15 If there are multiple individuals, multiple R 11 , R 12 and R 15 They are identical or different from each other. Specifically, R 11 , R 12 and R 15 Each independently consists of hydrogen, deuterium (D), and C6~C 60 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0154] a is an integer from 0 to 3, and b and e are each independently integers from 0 to 4. Here, when a, b, and e are each 0, R 11 , R 12 and R 15 represents that each is hydrogen, and if a, b, and e are each integers greater than or equal to 1, R 11 , R 12 and R 15 means that it is the aforementioned substituent excluding hydrogen.

[0155] In the above chemical formula 3, the R 10 , R 11 , R 12 and R 15 Wow, the above Ar 12 and Ar 13 The alkyl groups, aryl groups, heteroaryl groups, and condensation rings are each independently deuterium, halogen, cyano group, nitro group, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C1~C 40 alkyl group of, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, and if there are multiple substituents, they are identical or different from each other.

[0156] For a preferred specific example, the second organic compound represented by the above chemical formula 3 may be embodied in any one of the following chemical formulas 3A to 3B.

[0157] [Chemical Formula 3A]

[0158]

[0159] [Chemical Formula 3B]

[0160]

[0161] In the above chemical formulas 3A to 3B,

[0162] Y2 is O or S, and

[0163] R 13 and R 14 are identical or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C6~C 60 The aryl group of and heteroaryl groups having 5 to 60 nuclei may be selected from the group consisting of the aryl group and a heteroaryl group having 5 to 60 nuclei, or they may combine with any adjacent group to form a condensation ring, and the R 13 and R 14 If there are multiple individuals, multiple R 11 and R 12 They are identical or different from each other. Specifically, R 13 and R 14 Each independently consists of hydrogen, deuterium (D), and C6~C 60 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0164] c is an integer from 0 to 4, and d is an integer from 0 to 3. Here, when c and d are each 0, R 13 and R 14 represents that they are each hydrogen, and if c and d are each integers greater than or equal to 1, R 13 and R 14 This means that it is the aforementioned substituent excluding hydrogen.

[0165] Ar 14 and Ar 15 They are identical or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C6~C 60 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei. Specifically, Ar 14 and Ar 15 Each independently consists of hydrogen, deuterium (D), a halogen group, a cyano group, and C1~C 40 alkyl group of, C6~C 60 It can be selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei.

[0166] Also, X, Y1, R 10 , R 11 , R 12 , R 15 , n, a, b and e are each defined in Chemical Formula 3.

[0167] For example, in one embodiment according to the present invention, the second organic compound represented by the chemical formulas 3A to 3B is R introduced into the Y1-containing ring. 12 Depending on the bonding position, it can be embodied in any one of the following chemical formulas 4A to 4H.

[0168] [Chemical Formula 4A]

[0169]

[0170] [Chemical Formula 4B]

[0171]

[0172] [Chemical Formula 4C]

[0173]

[0174] [Chemical Formula 4D]

[0175]

[0176] [Chemical Formula 4E]

[0177]

[0178] [Chemical Formula 4F]

[0179]

[0180] [Chemical Formula 4G]

[0181]

[0182] [Chemical Formula 4H]

[0183]

[0184] In the above chemical formulas 4A to 4H,

[0185] X, Y1, Y2, R 10 , R 11 to R 15 , Ar 14 or Ar 15 , a, c, d, e, and n are as defined in chemical formulas 3A and 3B, respectively.

[0186] The second organic compound represented by Formula 2 according to the present invention described above may be further embodied as a compound represented by any one of the following exemplary compounds, such as compounds A-1 to B-4. However, the second organic compound represented by Formula 2 of the present invention is not limited to those exemplified below.

[0187]

[0188] In one embodiment according to the present invention, the first organic compound may be a hole-transporting compound that does not contain at least one carbazole group and an electron-accepting moiety (EWG) represented by the structural formula, and the second organic compound may be an electron-transporting compound that contains at least one electron-accepting moiety (EWG) represented by the structural formula. When such a hole-transporting first organic compound and an electron-transporting second organic compound are mixed as electron-transporting auxiliary layer materials, a synergy effect in hole and electron barrier performance can be secured by preventing hole leakage from the emissive layer to the electron-transporting region and preventing electron leakage from the emissive layer to the hole-transporting region due to the physical properties of each material.

[0189] In another embodiment according to the present invention, the electron transport assisting layer material may be composed of a homogeneous mixture in the form of an organic complex having a uniform mixed composition while physically interacting with each other, by including at least one first organic compound and at least one second organic compound and controlling the composition thereof.

[0190] Unlike conventional simple mixtures, such homogeneous mixtures not only have a uniform mixed composition but can also exhibit physicochemical and / or optical properties different from each individual organic compound constituting the homogeneous mixture or from a heterogeneous mixture in which they are simply mixed. Here, a simply mixed organic mixture refers to a simple mixture having a heterogeneous composition in which each compound is physically mixed.

[0191] For example, the maximum emission wavelength (λmax) of the homogeneous mixture may be shifted to a longer wavelength region than the maximum emission wavelength of the first organic compound, the second organic compound, and the heterogeneous organic mixture in which the first organic compound and the second organic compound are simply mixed. In this case, the value of the longer wavelength shift of the maximum emission wavelength exhibited by the homogeneous mixture is not particularly limited.

[0192] As another specific example, the bandgap energy of the homogeneous mixture may be smaller than the bandgap energy of the first organic compound, the second organic compound, and the simple organic mixture of the first organic compound and the second organic compound. In this case, the range of bandgap energy exhibited by the homogeneous mixture is not particularly limited as long as it satisfies the aforementioned physical properties.

[0193] The homogeneous mixture constituting the electron transport auxiliary layer of the present invention comprises a first organic compound and a second organic compound having the aforementioned predetermined moiety (e.g., EDG, EWG). Since no separate pre-treatment such as heat treatment or mechanical mixing is required, thermal damage to organic materials caused by the application of conventional pre-melting methods is fundamentally avoided. Furthermore, since a solid homogeneous mixture having a desired size and shape can be freely formulated, an organic electroluminescent device with high efficiency and long lifespan can be provided through the simplicity and simplification of the manufacturing process.

[0194] The electron transport assisting layer material of the present invention comprising the aforementioned homogeneous mixture may be solid at room temperature and does not contain other inorganic and / or metallic components known in the art. Such a homogeneous mixture can be prepared by a pre-mixed method known in the art, and specifically, it may be prepared according to the following two embodiments. However, it is not particularly limited thereto.

[0195] The first embodiment is to form a pre-mix having a homogeneous composition in a liquid phase using the solubility properties of at least two organic compounds, including a first organic compound and a second organic compound, with an organic solvent, and then obtain a homogeneous mixture in a solid phase by removing the solvent.

[0196] In one specific example, the homogeneous mixture may be obtained by completely dissolving a first organic compound and a second organic compound in at least one organic solvent to form a homogeneous phase, and then solidifying this homogeneous phase as is. Since the homogeneous mixture according to the first embodiment is solidified after being mixed intermolecularly under a suitable solvent, it is possible to fundamentally prevent minimal non-uniform composition caused by mixing between solids, as in the conventional pre-melting method. Furthermore, since mixing is performed using a solvent, mixing can be carried out without thermal damage at a significantly lower temperature than the pre-melting method.

[0197] To prepare such a homogeneous mixture, it is appropriate to use at least one organic solvent having a solubility index similar to that of at least two organic compounds to be mixed. The at least one organic solvent is not particularly limited as long as it is a substance capable of dissolving the first organic compound and the second organic compound to form a homogeneous phase. For example, a conventional organic solvent known in the art may be used alone, or a mixed solvent comprising two or more types may be used. Non-limiting examples of usable organic solvents include, but are not limited to, Tetrahydrofuran, Methylene chloride, Ethyl acetate, Acetone, Dimethyl Ether, benzene, toluene, 1,2-dichlorobenzene, monochlorobenzene, methanol, ethanol, and isopropyl alcohol. The mixing ratio between the two solvents is not particularly limited and may be included in a molar ratio of, for example, 1:99 to 99:1. In addition, the appropriate solvent can be selected by using two or more co-solvents.

[0198] The above solidification method is not particularly limited, and as long as the organic solvent contained in the liquid homogeneous mixture can be removed, the specific method and / or conditions thereof are not particularly limited. For example, a conventional drying method known in the art may be used, or a spray drying method may be used. The shape of the homogeneous mixture solidified in this way is not particularly limited, and may be, for example, in the form of a powder or a stick. If necessary, the homogeneous mixture obtained as a solid, such as a lump, may be physically ground using a mixer or the like.

[0199] A second embodiment involves homogeneously mixing at least two types of organic compounds, including a first organic compound and a second organic compound, in a gaseous state to form a pre-mix, and then cooling to obtain a solid homogeneous mixture. When a pre-mix having a gaseous homogeneous composition is formed in this way, it can have a homogeneous mixture composition at the molecular level compared to organic compounds or simply mixed heterogeneous mixtures produced by conventional solid / liquid methods.

[0200] For example, the homogeneous mixture may be formed by heating a mixture containing a first organic compound and a second organic compound under a vacuum atmosphere to create a pre-mixture of a homogeneous composition that has been vaporized, and then solidifying it as is. The method for manufacturing a homogeneous mixture using such a vaporization process may have two embodiments described below depending on the number of vacuum chambers used.

[0201] For example, at least two types of organic compounds, a first organic compound and a second organic compound, are introduced into a vacuum chamber and heated under a vacuum atmosphere to form a vaporized homogeneous mixture, and then the vaporized homogeneous mixture is cooled to recover a solidified homogeneous mixture.

[0202] As another example, a first organic compound and a second organic compound are introduced into one of a plurality of vacuum chambers in which the internal spaces are interconnected, and then heated under a vacuum atmosphere to form a homogeneous mixture that has been vaporized. Subsequently, the homogeneous mixture that has been vaporized is transferred to a second chamber connected to the first chamber, and then cooled to recover a solidified homogeneous mixture. In this way, when a vaporization process is carried out by providing at least two interconnected vacuum chambers, vapor purification is performed through movement between the interconnected vacuum chambers without the need for an additional manufacturing process. This fundamentally removes impurities, inorganic materials, and other impurities that may be generated by the application of heat, thereby ensuring high purity and providing an organic electroluminescent device with high efficiency and a long lifespan.

[0203] Here, the vaporization process conditions are not particularly limited, and for example, after introducing the first organic compound and the second organic compound into a vacuum chamber, they are heated to a temperature above the vaporization / sublimation temperature of the first and second organic compounds. At this time, the vacuum atmosphere is not particularly limited and can be appropriately controlled within the ordinary range known in the art. For example, 10 -2 to 10 -7 It can be a pressure reduction condition of torr.

[0204] When the above-described vaporization process is carried out, a homogeneous gaseous mixture mixed at the molecular level is formed, and at the same time, the impurities contained in the first and second organic compounds are purified, thereby producing an synergistic effect in purity. In particular, in the present invention, by vaporizing / sublimating the first and second organic compounds into a pre-mixture state without separate purification, rearrangement of molecules and subsequent structural / compositional changes at the molecular level can occur during mixed purification. Accordingly, not only is a superior improvement effect in removing chelate-derived impurities that occur when each organic substance is purified separately in the conventional manner, but the homogeneous mixture exhibits unique properties distinct from the first organic compound, the second organic compound, and the heterogeneous organic mixture in which the first and second organic compounds are simply mixed.

[0205] Subsequently, cooling is performed by controlling the temperature of the vacuum chamber, and accordingly, the vaporized homogeneous mixture is condensed and recrystallized through reverse sublimation to obtain a solid-phase homogeneous mixture. At this time, the cooling conditions are not particularly limited as long as the temperature is below the crystallization temperature of the first and second organic compounds.

[0206] The solid-phase homogeneous mixture obtained according to the two embodiments described above may be in the form of a powder or a stick. In addition, the average particle size (D 50 ) is 10 to 1000 μm, and more specifically, may be 100 to 500 μm. However, it is not particularly limited thereto.

[0207] If necessary, the present invention may crush the recovered solid homogeneous mixture into a predetermined size and shape according to conventional grinding and crushing methods known in the art. The average particle size of the homogeneous mixture crushed in this way has a smaller average particle size than that of the solidified homogeneous mixture. For example, the average particle size (D) of the crushed homogeneous mixture 50 ) is 5 to 500 μm, and specifically can be 10 to 100 μm.

[0208] In the present invention, a homogeneous thin film of an electron transport assisting layer provided in an organic electroluminescent device must be formed using the obtained solid-phase homogeneous mixture. Accordingly, it is desirable to process the solid-phase homogeneous mixture in powder or stick form into an appropriate shape and size suitable for conventional vacuum deposition (evaporation), sputtering, or other processes known in the art.

[0209] For example, the homogeneous mixture may be obtained by press-molding a solidified homogeneous mixture under non-heat treatment conditions.

[0210] In this case, the pressure molding method is not particularly limited, and conventional molding methods known in the art may be used without restriction. For example, 20,000 to 40,000 kgf / cm² 2 It can be injection molded under pressure. The shape of the homogeneous mixture thus pressure-molded is not particularly limited and, for example, may be a pellet shape selected from the group consisting of polyhedra, cylinders, and spheres. Alternatively, it can be freely modified into a solid having a shape and / or size desired by the user. For example, it may have the shape and / or size of a conventional sputtering target known in the art.

[0211] Meanwhile, when the electron transport auxiliary layer material according to the present invention is composed of a homogeneous mixture, the first organic compound and the second organic compound, which are the raw materials, form a homogeneous mixture through a liquid phase homogeneous mixing and drying process, a vapor phase homogeneous mixing and cooling / recrystallization process, and subsequently form at least one homogeneous organic layer thin film provided in an organic electroluminescent device through a conventional deposition method known in the art, so it is desirable to satisfy the following physical property conditions.

[0212] For example, the first organic compound and the second organic compound are 10 -2to 10 -7 It may have a sublimation or vaporization temperature difference of 30°C or less under a pressure of torr, specifically 10 -5 to 10 -6 The sublimation temperature difference under a pressure of torr is 20 ℃ or less, preferably 10 -6 It is 1 to 10 ℃ under a pressure of torr.

[0213] To give another specific example, the first organic compound and the second organic compound are 10 -2 to 10 -7 It may have a crystallization temperature difference of 30°C or less under a pressure of torr, preferably 10 -5 to 10 -6 Under a pressure of torr, the crystallization temperature difference is 20℃ or less, preferably 10 -6 It is 1 to 10 ℃ under a pressure of torr.

[0214] Specifically, the first organic compound and the second organic compound constituting the above-mentioned premix comprise at least one type of first organic compound and at least one type of second organic compound that are different from each other, and these may each be a sublimable organic material that is solid at room temperature.

[0215] Here, a preliminary mixture may be formed by mixing the first organic compound and the second organic compound in a molar ratio of about 1:99 to 99:1, for example, a molar ratio of 5:95 to 95:5, specifically a molar ratio of 10:90 to 90:10, more specifically a molar ratio of 20:80 to 80:20, or a molar ratio of 30:70 to 70:30. The aforementioned mixing ratio may also be expressed as a weight ratio. For example, the mixing ratio of the first organic compound and the second organic compound may be a weight ratio of 10:90 to 90:10, specifically a weight ratio of 20:80 to 80:20, more specifically a weight ratio of 30:70 to 70:30.

[0216] In the present invention, at least two types of organic compounds constituting a homogeneous mixture, a compound with strong electronic properties and a compound with strong hole properties are mixed to improve the mobility of electrons and holes, and simultaneously improve hole and electron barrier performance. For example, the first organic compound may be a compound with relatively strong hole properties, and the second organic compound may be a compound with relatively strong electronic properties. As such, the homogeneous mixture composed of the first organic compound with relatively strong hole properties and the second organic compound with relatively strong electronic properties has bipolar properties, and thus can significantly improve hole and electron barrier performance compared to the case where the first compound or the second compound is used alone.

[0217] Meanwhile, in the present invention, it is desirable to control the electron transport auxiliary layer to have an appropriate energy gap compared to the adjacent light-emitting layer and electron transport layer by ensuring that the first organic compound and the second organic compound constituting the electron transport auxiliary layer material each have physical properties such as a predetermined HOMO energy (HOMO), LUMO energy (LUMO), and triplet (T1) energy.

[0218] For example, the HOMO energy level of the first organic compound may be -5.0 eV or less, specifically -5.1 eV or less, and more specifically -5.3 eV or less. In this case, the minimum value of the HOMO energy level of the first organic compound is not particularly limited.

[0219] As another specific example, the LUMO energy level of the second organic compound may be -3.0 eV or higher, specifically -2.9 eV or higher, and more specifically -2.8 eV or higher. In this case, the maximum value of the LUMO energy level of the second organic compound is not particularly limited.

[0220] When a first organic compound and a second organic compound having the aforementioned properties are used in combination, and / or a homogeneous mixture composed including these is used as an electron transport auxiliary layer material, the characteristics utilizing the LUMO of the first organic compound and the HOMO of the second organic compound are exhibited. Accordingly, by realizing the characteristics of an electron transport auxiliary layer utilizing a wide range of energy barriers that cannot be realized in an electron transport auxiliary layer using a single organic material, the diffusion of electrons and holes injected into the light-emitting layer is prevented more efficiently, thereby enabling the improvement of the overall performance characteristics of an organic electroluminescent device containing the same.

[0221] As another specific example, the singlet energy (S1) of the electron transport assist layer material may be 3.0 eV or less, specifically 2.9 eV or less, and more specifically 2.8 eV or less. Here, the singlet energy (S1) is the singlet energy of the homogeneous mixture constituting the electron transport assist layer material, and the homogeneous mixture forms a new energy level while exciplexing, meaning that the singlet energy is 3.0 eV or less.

[0222] As another specific example, the triplet (T1) energy of the electron transport assisting layer material may be 2.6 eV or higher.

[0223] Since the singlet (S1) and triplet (T1) energy values ​​in the aforementioned electron transport auxiliary layer are higher than the singlet and triplet energy values ​​of the light-emitting layer, the phenomenon in which energy generated by exciton generation in the light-emitting layer is transferred to other layers within the organic electroluminescent device can be suppressed more efficiently. This means that the energy generated by excitons in the light-emitting layer is not converted into other forms but is entirely expressed as light, thereby improving the overall characteristics of the device. Here, the upper limit of the singlet (S1) energy and triplet (T1) energy of the electron transport auxiliary layer (53) is not specifically limited.

[0224] The first organic compound and the second organic compound, which can be used as electron transport auxiliary layer materials of the present invention as described above, can be further specified by the exemplary compounds described below. However, the first organic compound and the second organic compound constituting the electron transport auxiliary layer material according to the present invention are not limited to those exemplified below, and compounds with various modified chemical structures also fall within the scope of the present invention.

[0225]

[0226] Organic Electroluminescent Device

[0227] Meanwhile, another example of the present invention relates to an organic electroluminescent device (organic EL device) having an electron transport auxiliary layer comprising the electron transport auxiliary layer material described above.

[0228] Hereinafter, preferred embodiments of an organic electroluminescent device according to the present invention will be described with reference to the attached drawings. However, embodiments of the present invention may be modified in various other forms, and the scope of the present invention is not limited to the embodiments described below.

[0229] FIG. 1 is a cross-sectional view schematically showing the structure of an organic electroluminescent device (100) according to one embodiment of the present invention.

[0230] Referring to FIG. 1, the organic electroluminescent device (100) comprises: a first electrode (10); a second electrode (20); a light-emitting layer (40) located between the first electrode (10) and the second electrode (20); a hole transport region (30) located between the first electrode (10) and the light-emitting layer (40); and an electron transport region (50) located between the light-emitting layer (40) and the second electrode (20), and further comprises an electron transport auxiliary layer (53) between the light-emitting layer (40) and the electron transport region (50), wherein the electron transport auxiliary layer (53) comprises an electron transport auxiliary layer material composed of a homogeneous mixture including a first organic compound and a second organic compound.

[0231] Hereinafter, the configuration of an organic electroluminescent device (100) according to one embodiment of the present invention having the above-described configuration will be explained in more detail.

[0232] substrate

[0233] In the organic electroluminescent device according to the present invention, the substrate (not shown) may be any substrate commonly used in the field of organic electroluminescent devices without limitation. Considering the mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance of the organic electroluminescent device, it is preferable to use a glass substrate or a transparent plastic substrate.

[0234] First electrode

[0235] In the organic electroluminescent device (100) according to the present invention, the first electrode (10) is disposed on a substrate and acts as an anode that injects holes into the organic layer (A).

[0236] This first electrode (10) may be made of a material with a relatively high work function and, accordingly, becomes an anode that injects holes into an adjacent hole transport region (30). In this case, the second electrode (20) positioned opposite the first electrode (10) becomes a cathode that injects electrons into an adjacent electron transport region (50). However, it is not limited thereto, and depending on the case, the first electrode (10) may be a cathode and the second electrode (20) may be an anode.

[0237] The material forming the first electrode (10) is not particularly limited and may use conventional materials known in the industry. Non-limiting examples include metals such as vanadium, chromium, copper, zinc, and gold; alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al and SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline; and carbon black.

[0238] The method of manufacturing the first electrode (10) is not particularly limited and can be manufactured according to conventional methods known in the industry. For example, a method of coating an anode material on a substrate made of a silicon wafer, quartz, glass plate, metal plate, or plastic film may be used.

[0239] Second electrode

[0240] In the organic electroluminescent device (100) according to the present invention, the second electrode (20) is a portion positioned opposite to the first electrode (10) described above, specifically positioned on an electron transport region (50) and serves as a cathode that injects electrons into the organic layer (A).

[0241] The material forming the second electrode (20) is not particularly limited and can use conventional materials known in the industry. Non-limiting examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; alloys thereof; and multilayer materials such as LiF / Al and LiO2 / Al.

[0242] In this case, the second electrode (20) is a (semi)transparent electrode, and the organic electroluminescent device including the second electrode (20) may have a front-emitting structure. At this time, light generated from the light-emitting layer (40) may pass through the second electrode (20), but may also be reflected from the lower surface of the second electrode (20), and accordingly, may be repeatedly reflected between the upper surface of the first electrode (10) and the lower surface of the second electrode (20).

[0243] The method of manufacturing the second electrode (20) is also not particularly limited and can be manufactured according to methods known in the industry.

[0244] organic layer

[0245] The organic layer (A) included in the organic electroluminescent device according to the present invention may use a conventional configuration used as an organic layer of a conventional organic EL device without limitation, and may include, for example, one or more selected from the group consisting of a hole transport region (30), a light-emitting layer (40), and an electron transport region (50). At this time, considering the characteristics of the organic electroluminescent device, it is preferable to include all of the aforementioned organic layers.

[0246] Precision transport area

[0247] The hole transport region (30) included in the organic layer (A) of the present invention serves to move holes injected from the first electrode (10) to the light-emitting layer (40). This hole transport region (30) may include one or more selected from the group consisting of a hole injection layer (31), a hole transport layer (32), an electron blocking layer (hole transport auxiliary layer, not shown), and a light-emitting auxiliary layer (not shown). At this time, considering the characteristics of the organic electroluminescent device, it is preferable to include the hole injection layer (31) and the hole transport layer (32).

[0248] The material forming the aforementioned hole injection layer (31) and hole transport layer (32) is not particularly limited as long as it is a material with a low hole injection barrier and high hole mobility, and any hole injection layer / transport layer material used in the industry can be used without limitation. At this time, the material forming the hole injection layer (31) and hole transport layer (32) may be the same or different from each other.

[0249] The hole injection material mentioned above may be any hole injection material known in the art without limitation. Non-limiting examples of usable hole injection materials include phthalocyanine compounds such as copper phthalocyanine; DNTPD (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA (4,4',4"-tris(3-methylphenylphenylamino) triphenylamine), TDATA(4,4'4"-Tris(N,N-diphenylamino)triphenylamine), 2TNATA(4,4',4"-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine), PEDOT / PSS(Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate)), PANI / DBSA (Polyaniline / Dodecylbenzenesulfonic acid), PANI / CSA (Polyaniline / Camphor sulfonicacid), and PANI / PSS ((Polyaniline) / Poly(4-styrenesulfonate)) can be used individually. Or, two or more types can be mixed.

[0250] In addition, the hole transport material mentioned above may be any hole transport material known in the art without limitation. Non-limiting examples of usable hole transport materials include carbazole derivatives such as phenylcarbazole and polyvinylcarbazole, fluorene derivatives, triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine) and TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), NPB (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine), and TAPC (4,4'-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]). These may be used individually or in combination of two or more types.

[0251] The hole transport region (30) can be manufactured using conventional methods known in the art. Examples include vacuum deposition, spin coating, casting, LB method (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI), but are not limited thereto.

[0252] The thickness of the hole transport region (30) can be appropriately adjusted within a normal range known in the art, for example, from 100 Å to about 2000 Å. If the hole transport region (30) includes an electron blocking layer (hole transport auxiliary layer), a hole transport layer, or any combination thereof, the thickness of the electron blocking layer (hole transport auxiliary layer) is about 50 Å to about 400 Å, and in this case, the thickness of the hole transport layer (32) can be about 50 Å to about 1600 Å. When the thicknesses of the hole transport region (30), the electron blocking layer (hole transport auxiliary layer), and the hole transport layer (32) satisfy the aforementioned ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

[0253] light-emitting layer

[0254] The light-emitting layer (40) included in the organic layer (A) of the present invention is a layer in which holes and electrons meet to form excitons, and the color of light emitted by the organic electroluminescent device may vary depending on the material forming the light-emitting layer (40).

[0255] The light-emitting layer (40) may include at least one host and at least one dopant, and the mixing ratio thereof can be appropriately adjusted within a range known in the art. For example, the light-emitting layer (40) may include 70 to 99.9 parts by weight of a host and 0.1 to 30 parts by weight of a dopant based on the total weight of the light-emitting layer (40). More specifically, if the light-emitting layer (40) is blue fluorescence, green fluorescence, or red fluorescence, it may include 80 to 99.9 parts by weight of a host and 0.1 to 20 parts by weight of a dopant. Additionally, if the light-emitting layer (40) is blue fluorescence, green fluorescence, or red phosphorescence, it may include 70 to 99 parts by weight of a host and 1 to 30 parts by weight of a dopant.

[0256] The host included in the light-emitting layer (40) of the present invention is not particularly limited as long as it is known in the art, and non-limiting examples thereof include alkali metal complexes; alkaline earth metal complexes; or condensed aromatic ring derivatives. More specifically, as the host material, it is preferable to use aluminum complexes, beryllium complexes, anthracene derivatives, pyrene derivatives, triphenylene derivatives, carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, or a combination of one or more of these, which can increase the light-emitting efficiency and lifespan of the organic electroluminescent device.

[0257] In one specific example, the light-emitting layer (40) comprises at least one type of host, and at least one of the first organic compound and the second organic compound of the electron transport auxiliary layer (53) described later may be different from each other. Specifically, at least one type of host material of the light-emitting layer (40); and the first organic compound and the second organic compound of the electron transport auxiliary layer (53) may all be different.

[0258] In addition, the dopant included in the light-emitting layer (40) of the present invention is not particularly limited as long as it is known in the art, and non-limiting examples thereof include anthracene derivatives, pyrene derivatives, arylamine derivatives, metal complex compounds including iridium (Ir) or platinum (Pt), etc.

[0259] The above dopants may be classified into red dopants, green dopants, and blue dopants, and red dopants, green dopants, and blue dopants that are ordinarily known in the relevant technical field may be used without particular restriction.

[0260] Specifically, non-limiting examples of red dopants include PtOEP (Pt(II) octaethylporphine), Ir(piq)3 (tris(2-phenylisoquinoline)iridium), Btp2Ir(acac) (bis(2-(2'-benzothienyl)-pyridinato-N,C3')iridium(acetylacetonate)), or mixtures of two or more of these.

[0261] In addition, non-limiting examples of green dopants include Ir(ppy)3 (tris(2-phenylpyridine) iridium), Ir(ppy)2(acac) (Bis(2-phenylpyridine)(Acetylacetonato)iridium(III)), Ir(mppy)3 (tris(2-(4-tolyl)phenylpyridine)iridium), C545T (10-(2-benzothiazolyl)-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-[1]benzopyrano [6,7,8-ij]-quinolizin-11-one: There are 10-(2-benzothiazoleyl)-1,1,7,7-tetramethyl-2,3,6,7,-tetrahydro-1H,5H,11H-[1]benzopyrano [6,7,8-ij]-quinolizine-11-one), or mixtures of two or more of these.

[0262] In addition, non-limiting examples of blue dopants include F2Irpic (Bis[3,5-difluoro-2-(2-pyridyl)phenyl](picolinato)iridium(III)), (F2ppy)2Ir(tmd), Ir(dfppz)3, DPVBi (4,4'-bis(2,2'-diphenylethen-1-yl)biphenyl), DPAVBi (4,4'-Bis[4-(diphenylamino)styryl]biphenyl), and TBPe (2,5,8,11-tetra-tert-butyl perylene: There are 2,5,8,11-tetra-tert-butylperylene), or mixtures of two or more of these.

[0263] The light-emitting layer (40) according to the present invention may be a red light-emitting layer comprising a red phosphorescent material; a green light-emitting layer comprising a green phosphorescent material; or a blue light-emitting layer comprising a blue phosphorescent material or a blue fluorescent material. Preferably, it may be a light-emitting layer comprising a blue fluorescent material.

[0264] The aforementioned light-emitting layer (40) may be composed of a single layer made of one type of material, a single layer made of multiple different materials, or multiple layers of two or more layers each made of different materials. Here, when the light-emitting layer (40) consists of multiple layers, the organic electroluminescent device can emit light of various colors. Specifically, the present invention can provide an organic electroluminescent device that exhibits mixed colors by providing multiple light-emitting layers made of different materials in series. In addition, when multiple light-emitting layers are included, the driving voltage of the device increases, while the current value within the organic electroluminescent device becomes constant, thereby providing an organic electroluminescent device with improved light-emitting efficiency proportional to the number of light-emitting layers.

[0265] The light-emitting layer (40) can be manufactured using conventional methods known in the art. Examples include vacuum deposition, spin coating, casting, LB method (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI), but are not limited thereto.

[0266] In addition, the thickness of the light-emitting layer (40) can be appropriately adjusted within a conventional range known in the art, for example, about 100 Å to about 500 Å. When the thickness of the light-emitting layer (40) satisfies the range described above, excellent light-emitting characteristics can be exhibited.

[0267] Meanwhile, although not shown in the drawing, the organic electroluminescent device (100) may have a plurality of light-emitting stacks (not shown) including at least one light-emitting layer.

[0268] A plurality of light-emitting layers included in such a light-emitting stack may each be light-emitting layers that emit light of different colors or light-emitting layers that emit light of the same color. That is, the color of light emitted may vary depending on the material constituting the light-emitting layer. For example, a plurality of light-emitting stacks may include materials that emit blue, green, red, yellow, white, etc., and may be formed using phosphorescent or fluorescent materials. In this case, the colors exhibited by each light-emitting layer may be complementary colors to one another. Additionally, colors may be selected as a combination of colors capable of emitting white light. Each of these light-emitting layers may each include phosphorescent dopants or fluorescent dopants corresponding to the selected color.

[0269] Additionally, although not shown in the drawing, the organic electroluminescent device (100) may further include a charge generation layer (not shown) that is disposed between adjacent stacks among a plurality of light-emitting stacks and connects them.

[0270] A charge generation layer (CGL) refers to a layer that separates adjacent light-emitting stacks without directly contacting both electrodes (e.g., anode, cathode) in an organic light-emitting device having multiple light-emitting stacks. This charge generation layer is positioned between two adjacent light-emitting stacks to generate electrons for one light-emitting stack and act as a cathode, and generates holes for the other light-emitting stack and acts as an anode. The charge generation layer may be formed using any material known in the art that can be used as a charge generation layer material without limitation. Additionally, the material used for the charge generation layer may be formed by doping it with a conventional n-type material and / or p-type material known in the art.

[0271] Electron transport auxiliary layer

[0272] An organic electroluminescent device according to the present invention comprises an electron transport auxiliary layer (53) disposed between a light-emitting layer (40) and an electron transport region (50), wherein the electron transport auxiliary layer (53) comprises an electron transport auxiliary layer material containing the aforementioned first organic compound and second organic compound.

[0273] For example, the electron transport auxiliary layer (53) may be formed by depositing the aforementioned electron transport auxiliary layer material through a single deposition source. More specifically, the electron transport auxiliary layer material may be composed of a solid-phase homogeneous mixture.

[0274] Furthermore, since each component constituting the electron transport auxiliary layer material that constitutes the electron transport auxiliary layer (53) according to the present invention is identical to the above description, individual descriptions thereof are omitted.

[0275] The electron transport auxiliary layer (53) can be manufactured using conventional methods known in the art. Examples include vacuum deposition, spin coating, casting, LB method (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI), but are not limited thereto.

[0276] In addition, the thickness of the electron transport auxiliary layer (53) can be appropriately adjusted within a normal range known in the field, for example, about 50 Å to about 200 Å. When the thickness of the electron transport auxiliary layer (53) satisfies the range described above, not only is the light emission efficiency of the light-emitting layer increased, but hole leakage from the light-emitting layer to the electron transport region and electron leakage from the light-emitting layer to the hole transport region are simultaneously prevented, thereby securing an synergistic effect on the efficiency and lifespan characteristics of the device.

[0277] Meanwhile, in the present invention, the electron transport auxiliary layer (53) is described as a separate layer, but this is described as an example for convenience, and in a broader sense, it can be understood as being included in a part of the electron transport region (50) described later.

[0278] Electronic transport area

[0279] In the organic electroluminescent device (100) according to the present invention, the electron transport region (50) included in the organic layer (A) serves to move electrons injected from the second electrode (20) to the light-emitting layer (40).

[0280] This electron transport region (50) may include at least one of an electron transport layer (52) and an electron injection layer (51). In this case, considering the characteristics of the organic electroluminescent device, it is preferable to include an electron transport layer (52) and an electron injection layer (51).

[0281] The electron transport region (50) according to the present invention may include the aforementioned electron transport auxiliary layer (53) when judged based on the electron transport capability. In this case, the electron transport region (50) may have a structure in which the electron transport auxiliary layer (53) and the electron transport layer (52) are arranged based on the light-emitting layer (40), the electron transport auxiliary layer (53) and the electron injection layer (51) are arranged, or the electron transport auxiliary layer (53), the electron transport layer (52), and the electron injection layer (51) are arranged sequentially.

[0282] In one specific example, the electron transport region (50) includes an electron transport layer (52), and at least one of the material of the adjacent electron transport layer (52); and the first organic compound and the second organic compound of the electron transport auxiliary layer (53) may be different from each other. Specifically, the material of the electron transport layer (52); and the first organic compound and the second organic compound of the electron transport auxiliary layer (53) may both be different.

[0283] The material constituting the electron transport layer (52) above may be any material having conventional electron transport properties known in the art without limitation. For example, it may include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), nitrogen-containing heterocyclic derivatives, etc.

[0284] The electron transport region (50) according to the present invention, specifically the electron injection layer (51), may use an electron transport capacity material in which an n-type dopant and an electron transport capacity material are co-deposited to facilitate the injection of electrons from the cathode. In this case, the n-type dopant may be any alkali metal complex known in the art without limitation, and examples include alkali metals, alkaline earth metals, or rare earth metals.

[0285] The above electron transport region (50) can be manufactured through conventional methods known in the art. Examples include vacuum deposition, spin coating, casting, LB method (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI), but are not limited thereto.

[0286] The electron transport region (50) may be composed of an electron transport layer (52) and the electron transport auxiliary layer (53) described above, and the total thickness may be 150 Å to 600 Å. At this time, the thickness of the electron transport layer (52) may be about 100 Å to 400 Å, and the thickness of the electron transport auxiliary layer (53) may be about 50 Å to about 200 Å as described above. When the thickness of the electron transport region (50) satisfies the aforementioned range, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage.

[0287] light-emitting auxiliary layer

[0288] Optionally, the organic light-emitting element (100) of the present invention may further include a light-emitting auxiliary layer (not shown) disposed between the hole transport region (30) and the light-emitting layer (40).

[0289] The light-emitting auxiliary layer serves to transport holes moving from the hole transport region (30) to the light-emitting layer (30) and to control the thickness of the organic layer (A). This light-emitting auxiliary layer has a high LUMO value to prevent electrons from moving to the hole transport layer and has a high triplet energy to prevent excitons from the light-emitting layer from diffusing into the hole transport layer.

[0290] This light-emitting auxiliary layer may include a hole transport material and may be made of the same material as the hole transport region. Additionally, the light-emitting auxiliary layers of red, green, and blue organic light-emitting devices may be made of the same material.

[0291] The material for the light-emitting auxiliary layer is not particularly limited, and examples include carbazole derivatives or arylamine derivatives. Non-limiting examples of usable light-emitting auxiliary layers include NPD (N, N-dinaphthyl-N, N'-diphenyl benzidine), TPD (N, N'-bis-(3-methylphenyl)-N, N'-bis(phenyl)-benzidine), s-TAD, and MTDATA (4, 4', 4″-Tris(N-3-methylphenyl-Nphenyl-amino)-triphenylamine). These may be used alone or in a mixture of two or more. In addition, the light-emitting auxiliary layer may include a p-type dopant in addition to the aforementioned materials. Known p-type dopants used in the relevant technical field may be used as such p-type dopants.

[0292] capping layer

[0293] Optionally, the organic electroluminescent device (100) according to the present invention may further include a capping layer (not shown) disposed on the second electrode (20). This capping layer protects the organic electroluminescent device and helps light generated from the organic layer (A) to be efficiently emitted to the outside.

[0294] The capping layer may comprise at least one selected from the group consisting of tris-8-hydroxyquinoline aluminum (Alq3), ZnSe, 2,5-bis(6′-(2′,2″-bipyridyl))-1,1-dimethyl-3,4-diphenylsilole, 4′-bis[N-(1-napthyl)-N-phenyl-amion] biphenyl (α-NPD), N,N′-diphenyl-N,N′-bis(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine (TPD), and 1,1′-bis(di-4-tolylaminophenyl) cyclohexane (TAPC). The material forming this capping layer is inexpensive compared to the material of other layers constituting the organic electroluminescent device.

[0295] The capping layer may be a single layer, or may include two or more layers having different refractive indices, so that the refractive index gradually changes as it passes through two or more layers.

[0296] The above capping layer can be manufactured through conventional methods known in the art, and various methods such as vacuum deposition, spin coating, casting, or the Langmuir-Blodgett (LB) method can be used.

[0297] The organic electroluminescent device (100) of the present invention, comprising the above-described configuration, can be manufactured according to conventional methods known in the art. For example, an organic light-emitting device can be manufactured by vacuum depositing an anode material on a substrate, and then vacuum depositing materials of a hole transport region material, a light-emitting layer material, an electron transport auxiliary layer material, an electron transport region material, and a cathode material in sequence on the anode.

[0298] In addition, the organic electroluminescent device (100) according to the present invention has a structure in which a first electrode (10), an organic layer (A), and a second electrode (20) are sequentially stacked, and may further include an insulating layer or an adhesive layer between the first electrode (10) and the organic layer (A) or between the second electrode (20) and the organic layer (A). The organic electroluminescent device of the present invention may have excellent lifespan characteristics because, when voltage, current, or both are applied, the lifespan of the initial brightness is increased while maintaining maximum luminous efficiency.

[0299]

[0300] The present invention will be described in detail below through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.

[0301]

[0302] [Preparation Example 1] Synthesis of DBF-1

[0303] <Step 1> Synthesis of 4-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan

[0304]

[0305] 4,4,5,5-tetramethyl-2-(6-phenyldibenzo[b,d]furan-4-yl)-1,3,2-dioxaborolane (100.0 g, 270.0 mmol), 1-bromo-3-chlorobenzene (62.0 g, 324.1 mmol), Pd(PPh3)4 (15.6 g, 13.5 mmol), K2CO3 (93.3 g, 675.2 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed under a nitrogen stream and stirred at 120°C for 4 hours.

[0306] After the reaction was completed, the mixture was extracted with methylene chloride, MgSO4 was added, and the solution was filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:DCM = 9:1 (v / v)) to obtain 4-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan (48.9 g, yield 51%).

[0307] Mass (Theoretical value: 354.83, Measured value: 354 g / mol)

[0308] <Step 2> Synthesis of DBF-1

[0309]

[0310] 4-(3-chlorophenyl)-6-phenyldibenzo[b,d]furan (48.9 g, 137.7 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (38.5 g, 151.5 mmol), Pd(dppf)Cl2 (12.1 g, 13.8 mmol), KOAc (38.9 g, 413.2 mmol), and 1,4-Dioxane (1000 ml) were mixed under a nitrogen stream and stirred at 130°C for 12 hours.

[0311] After the reaction was completed, the mixture was extracted with ethyl acetate, water was removed with MgSO4, and purified by column chromatography (Hexane:DCM = 4:1 (v / v)) to obtain DBF-1 (26.4 g, yield 43%).

[0312] Mass (Theoretical value: 446.35, Measured value: 446 g / mol)

[0313]

[0314] [Preparation Example 2] Synthesis of DBF-2

[0315] <Step 1-2> Synthesis of DBF-2

[0316]

[0317] The target compound DBF-2 (56.4 g, final yield 46.9%) was obtained by performing the same process as in steps 1 and 2, except that 4,4,5,5-tetramethyl-2-(6-phenyldibenzo[b,d]furan-4-yl)-1,3,2-dioxaborolane (100 g, 251.6 mmol) was used instead of 4,4,5,5-tetramethyl-2-(6-(phenyl-d5)dibenzo[b,d]thiophen-4-yl-1,2,3,7,8,9-d6)-1,3,2-dioxaborolane (100 g, 251.6 mmol) and 1-bromo-3-chlorobenzene-2,4,5,6-d4 (59.0 g, 302.0 mmol) was used instead of 1-bromo-3-chlorobenzene.

[0318] Mass (Theoretical value: 477.51, Measured value: 477 g / mol)

[0319]

[0320] [Synthesization Example 1] Synthesis of A-1

[0321]

[0322] DBF-1 (10.0 g, 22.4 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (9.6 g, 26.9 mmol), Pd(PPh3)4 (1.3 g, 1.1 mmol), K2CO3 (7.7 g, 56.0 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed under a nitrogen stream and stirred at 120°C for 4 hours.

[0323] After the reaction was completed, the mixture was extracted with methylene chloride, MgSO4 was added, and the solution was filtered. After removing the solvent from the obtained organic layer, the solution was purified by column chromatography (Hexane:EA = 4:1 (v / v)) to obtain the target compound A-1 (11.8 g, yield 82%).

[0324] Mass (Theoretical value: 641.73, Measured value: 641 g / mol)

[0325]

[0326] [Synthesization Example 2] Synthesis of A-2

[0327]

[0328] The target compound A-2 (11.9 g, yield 74%) was obtained by performing the same process as in Synthesis Example 1, except that 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.9 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine.

[0329] Mass (Theoretical value: 717.83, Measured value: 717 g / mol)

[0330]

[0331] [Synthesization Example 3] Synthesis of A-3

[0332]

[0333] The target compound A-3 (11.4 g, yield 71%) was obtained by performing the same process as in Synthesis Example 1, except that 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (12.9 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine.

[0334] Mass (Theoretical value: 717.83, Measured value: 717 g / mol)

[0335]

[0336] [Synthesization Example 4] Synthesis of A-4

[0337]

[0338] The target compound A-4 (12.7 g, yield 79%) was obtained by performing the same process as in Synthesis Example 1, except that 2-(4-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.9 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine.

[0339] Mass (Theoretical value: 717.83, Measured value: 717 g / mol)

[0340]

[0341] [Synthesization Example 5] Synthesis of A-5

[0342]

[0343] The target compound A-5 (10.9 g, yield 61%) was obtained by performing the same process as in Synthesis Example 1, except that 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (14.9 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine.

[0344] Mass (Theoretical value: 793.93, Measured value: 793 g / mol)

[0345]

[0346] [Synthesization Example 6] Synthesis of A-6

[0347]

[0348] The target compound A-6 (9.6 g, yield 54%) was obtained by performing the same process as in Synthesis Example 1, except that 2-([1,1':3',1''-terphenyl]-5'-yl)-4-chloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (13.7 g, 26.9 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine.

[0349] Mass (Theoretical value: 793.93, Measured value: 793 g / mol)

[0350]

[0351] [Synthesization Example 7] Synthesis of B-1

[0352]

[0353] DBF-2 (10.0 g, 20.9 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (9.0 g, 25.1 mmol), Pd(PPh3)4 (1.2 g, 1.0 mmol), K2CO3 (7.2 g, 52.4 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed under a nitrogen stream and stirred at 120°C for 4 hours.

[0354] After the reaction was completed, extraction with methylene chloride was performed, MgSO4 was added, and the mixture was filtered. After removing the solvent from the obtained organic layer, the solution was purified by column chromatography (Hexane:EA = 4:1 (v / v)) to obtain the target compound B-1 (8.7 g, yield 62%).

[0355] Mass (Theoretical value: 672.88, Measured value: 672 g / mol)

[0356]

[0357] [Synthesization Example 8] Synthesis of B-2

[0358]

[0359] The target compound B-2 (9.2 g, yield 67%) was obtained by performing the same process as in Synthesis Example 7, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (8.6 g, 25.1 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine.

[0360] Mass (Theoretical value: 658.90, Measured value: 658 g / mol)

[0361]

[0362] [Synthesization Example 9] Synthesis of B-3

[0363]

[0364] The target compound B-3 (9.5 g, yield 69%) was obtained by performing the same process as in Synthesis Example 7, except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (8.6 g, 25.1 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine.

[0365] Mass (Theoretical value: 658.90, Measured value: 658 g / mol)

[0366]

[0367] [Synthesization Example 10] Synthesis of B-4

[0368]

[0369] The target compound B-4 (11.3 g, yield 72%) was obtained by performing the same process as in Synthesis Example 7, except that 2-chloro-4-phenyl-6-(9-phenyldibenzo[b,d]furan-3-yl)-1,3,5-triazine (10.9 g, 25.1 mmol) was used instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine.

[0370] Mass (Theoretical value: 748.98, Measured value: 748 g / mol)

[0371]

[0372] [Preparation Example 3] Synthesis of Cz-D1, Cz-D2, Cz-D3, and Cz-D4

[0373] <Step 1-1> Synthesis of Cz-D1

[0374]

[0375] 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (134.3 g, 530.6 mmol), iodobenzene (130.0 g, 636.7 mmol), Cu (16.8 g, 265.3 mmol), K2CO3 (146.7 g, 1,061.3 mmol), and toluene (1000 ml) were mixed under a nitrogen stream and stirred at 110°C for 12 hours.

[0376] After the reaction was completed, the product was extracted with ethyl acetate, water was removed with MgSO4, and purified by column chromatography (Hexane:EA = 5:1 (v / v)) to obtain Cz-D1 (125.7 g, yield 72%).

[0377] Mass (Theoretical value: 329.25, Measured value: 329 g / mol)

[0378] <Step 1-2> Synthesis of Cz-D2

[0379]

[0380] The same process as in step 1-1 was performed, except that 4-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene, to obtain the target compound Cz-D2 (135.5 g, yield 63%).

[0381] Mass (Theoretical value: 405.35, Measured value: 405 g / mol)

[0382] <Step 1-3> Synthesis of Cz-D3

[0383]

[0384] The same process as in step 1-1 was performed to obtain the target compound Cz-D3 (148.4 g, yield 69%), except that 3-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene.

[0385] Mass (Theoretical value: 405.35, Measured value: 405 g / mol)

[0386] <Step 1-4> Synthesis of Cz-D4

[0387]

[0388] The target compound Cz-D4 (96.8 g, yield 45%) was obtained by performing the same process as in step 1-1, except that 2-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene.

[0389] Mass (Theoretical value: 405.35, Measured value: 405 g / mol)

[0390]

[0391] [Preparation Example 4] Synthesis of BCz-D1, BCz-D2, BCz-D3, and BCz-D4

[0392] <Step 1> Synthesis of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7

[0393]

[0394] Cz-D1 (100.0 g, 303.7 mmol), 4,4,4',4',5,5, 5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (84.8 g, 334.1 mmol), Pd(dppf)Cl2 (26.6 g, 30.3 mmol), KOAc (85.8 g, 911.1 mmol), and 1,4-Dioxane (1000 ml) were mixed under a nitrogen stream and stirred at 130°C for 12 hours.

[0395] After the reaction was completed, the mixture was extracted with ethyl acetate, water was removed with MgSO4, and purified by column chromatography (Hexane:EA = 8:1 (v / v)) to obtain 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 (96.0 g, yield 84%).

[0396] Mass (Theoretical value: 376.3, Measured value: 376 g / mol)

[0397] <Step 2-1> Synthesis of BCz-D1

[0398]

[0399] 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 (96.0 g, 255.1 mmol), 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (77.5 g, 306.1 mmol), Pd(PPh3)4 (14.7 g, 12.7 mmol), K2CO3 (88.1 g, 637.8 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed under a nitrogen stream and stirred at 120°C for 4 hours.

[0400] After the reaction was completed, it was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the obtained organic layer, it was purified by column chromatography (Hexane:EA = 7:1 (v / v)) to obtain BCz-D1 (71.1 g, yield 66%).

[0401] Mass (Theoretical value: 422.59, Measured value: 422 g / mol)

[0402] <Step 2-2> Synthesis of BCz-D2

[0403]

[0404] The same process as in Step 1 and Step 2-1 was performed, except that Cz-D2 (100 g, 246.7 mmol) was used instead of Cz-D1, to obtain the target compound BCz-D2 (66.4 g, final yield 54.0%).

[0405] Mass (Theoretical value: 498.69, Measured value: 498 g / mol)

[0406] <Step 2-3> Synthesis of BCz-D3

[0407]

[0408] The same process as in Step 1 and Step 2-1 was performed, except that Cz-D3 (100 g, 246.7 mmol) was used instead of Cz-D1, to obtain the target compound BCz-D3 (59.7 g, final yield 48.5%).

[0409] Mass (Theoretical value: 498.69, Measured value: 498 g / mol)

[0410] <Step 2-4> Synthesis of BCz-D4

[0411]

[0412] The same process as in Step 1 and Step 2-1 was performed, except that Cz-D4 (100 g, 246.7 mmol) was used instead of Cz-D1, to obtain the target compound BCz-D4 (59.4 g, final yield 48.3%).

[0413] Mass (Theoretical value: 498.69, Measured value: 498 g / mol)

[0414]

[0415] [Synthesization Example 11] Synthesis of C-1

[0416]

[0417] BCz-D1 (10.0 g, 23.6 mmol), Cz-D1 (9.3 g, 28.3 mmol), Pd(OAc)2 (1.36 g, 1.18 mmol), P(t-Bu)3 (0.57 ml, 2.36 mmol), NaO(t-Bu) (4.55 g, 47.3 mmol), and toluene (100 ml) were mixed under a nitrogen stream and stirred at 110°C for 5 hours. After the reaction was complete, the toluene was concentrated, the solid salt was filtered, and the mixture was purified by recrystallization to obtain the target compound, C-1 (13.0 g, yield 82%).

[0418] Mass (Theoretical value: 670.93, Measured value: 670 g / mol)

[0419]

[0420] [Synthesization Example 12] Synthesis of C-2

[0421]

[0422] The target compound C-2 (13.8 g, yield 78%) was obtained by performing the same process as in Synthesis Example 11, except that Cz-D2 (11.4 g, 28.3 mmol) was used instead of Cz-D1.

[0423] Mass (Theoretical value: 747.02, Measured value: 747 g / mol)

[0424]

[0425] [Synthesization Example 13] Synthesis of C-3

[0426]

[0427] The target compound F-3 (13.2 g, yield 75%) was obtained by performing the same process as in Synthesis Example 11, except that Cz-D3 (11.4 g, 28.3 mmol) was used instead of Cz-D1.

[0428] Mass (Theoretical value: 747.02, Measured value: 747 g / mol)

[0429]

[0430] [Synthesization Example 14] Synthesis of C-4

[0431]

[0432] The target compound F-4 (12.2 g, yield 69%) was obtained by performing the same process as in Synthesis Example 11, except that Cz-D4 (11.4 g, 28.3 mmol) was used instead of Cz-D1.

[0433] Mass (Theoretical value: 747.02, Measured value: 747 g / mol)

[0434]

[0435] [Synthesization Example 15] Synthesis of C-5

[0436]

[0437] BCz-D2 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), Pd(OAc)2 (1.15 g, 1.0 mmol), P(t-Bu)3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed under a nitrogen stream and stirred at 110°C for 5 hours. After the reaction was complete, the toluene was concentrated, the solid salt was filtered, and the mixture was purified by recrystallization to obtain the target compound, C-5 (10.2 g, yield 62%).

[0438] Mass (Theoretical value: 747.02, Measured value: 747 g / mol)

[0439]

[0440] [Synthesization Example 16] Synthesis of C-6

[0441]

[0442] BCz-D3 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), Pd(OAc)2 (1.15 g, 1.0 mmol), P(t-Bu)3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed under a nitrogen stream and stirred at 110°C for 5 hours. After the reaction was complete, the toluene was concentrated, the solid salt was filtered, and the mixture was purified by recrystallization to obtain the target compound, C-6 (9.4 g, yield 63%).

[0443] Mass (Theoretical value: 747.02, Measured value: 747 g / mol)

[0444]

[0445] [Synthesization Example 17] Synthesis of C-7

[0446]

[0447] BCz-D4 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), Pd(OAc)2 (1.15 g, 1.0 mmol), P(t-Bu)3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed under a nitrogen stream and stirred at 110°C for 5 hours. After the reaction was complete, the toluene was concentrated, the solid salt was filtered, and the mixture was purified by recrystallization to obtain the target compound, C-7 (8.1 g, yield 54%).

[0448] Mass (Theoretical value: 747.02, Measured value: 747 g / mol)

[0449]

[0450] [Synthesization Example 18] Synthesis of C-8

[0451]

[0452] The target compound C-8 (9.9 g, yield 73%) was obtained by performing the same process as in Synthesis Example 11, except that 4-bromo-1,1'-biphenyl (6.6 g, 28.3 mmol) was used instead of Cz-D1.

[0453] Mass (Theoretical value: 574.79, Measured value: 574 g / mol)

[0454]

[0455] [Synthesization Example 19] Synthesis of C-9

[0456]

[0457] The target compound C-9 (10.2 g, yield 78%) was obtained by performing the same process as in Synthesis Example 15, except that 4-bromo-1,1'-biphenyl (5.6 g, 24.1 mmol) was used instead of Cz-D1.

[0458] Mass (Theoretical value: 650.88, Measured value: 650 g / mol)

[0459]

[0460] [Synthesization Example 20] Synthesis of C-10

[0461]

[0462] The target compound C-10 (9.8 g, yield 75%) was obtained by performing the same process as in Synthesis Example 16, except that 4-bromo-1,1'-biphenyl (5.6 g, 24.1 mmol) was used instead of Cz-D1.

[0463] Mass (Theoretical value: 650.88, Measured value: 650 g / mol)

[0464]

[0465] [Synthesization Example 21] Synthesis of C-11

[0466]

[0467] The target compound C-11 (8.1 g, yield 62%) was obtained by performing the same process as in Synthesis Example 16, except that 3-bromo-1,1'-biphenyl (5.6 g, 24.1 mmol) was used instead of Cz-D1.

[0468] Mass (Theoretical value: 650.88, Measured value: 650 g / mol)

[0469]

[0470] [Example 1] Fabrication of a Blue Organic EL Device

[0471] After purifying the second organic compound A-1 synthesized in Synthesis Example 1 and the first organic compound C-1 synthesized in Synthesis Example 11 to high purity using a commonly known method, a green organic EL device was fabricated according to the following process.

[0472] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1500 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0473] An organic electroluminescent device was fabricated by stacking 98 wt% HI + 2 wt% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / 98 wt% BH + 2 wt% BD (20 nm) / 70% compound C-1 + 30% compound A-1 (5 nm) / ET + Liq (1:1 weight ratio) (30 nm) / LiF (1 nm) / Al (100 nm) in that order on the prepared ITO transparent electrode. At this time, the structures of HI, HAT-CN6, EB, BH, BD, ET, and Liq are as follows.

[0474]

[0475]

[0476] [Examples 2] ~ [Examples 110] Preparation of Blue Organic EL Devices

[0477] A blue organic EL device was manufactured in the same manner as Example 1 below, except that the first organic compound and the second organic compound were used as electron transport auxiliary layer materials as shown in Table 1 below.

[0478]

[0479] [Comparative Examples 1–10] Fabrication of Blue Organic EL Devices

[0480] A blue organic EL device was fabricated using the same process as in Example 1, except that a second organic compound (e.g., A-1 to B-4) was used alone as the electron transport auxiliary layer material.

[0481]

[0482] [Comparative Examples 11–14] Fabrication of Blue Organic EL Devices

[0483] A blue organic EL device was fabricated using the same process as in Example 1, except that a combination of two different types of second organic compounds was used as the electron transport auxiliary layer material.

[0484]

[0485] [Evaluation Example 1]

[0486] For the green organic EL devices prepared in Examples 1 to 110 and Comparative Examples 1 to 14, respectively, the driving voltage, current efficiency, emission peak, and lifetime at a current density of 10 mA / cm² were measured, and the results are shown in Table 1 below.

[0487] Sample 1 Organic Compound 2 Organic Compound Driving Voltage (V) PL Peak (nm) Current Efficiency (cd / A) Lifetime (hr, T 97Example 1 C-1A-13.24452 10.4182 Example 2 C-2A-13.24450 10.9181 Example 3 C-3A-13.15453 10.1184 Example 4 C-4A-13.27453 11.1181 Example 5 C-5A-13.21450 10.8188 Example 6 C-6A-13.18453 10.7180 Example 7 C-7A-13.16453 10.6184 Example 8 C-8A-13.39453 10.5181 Example 9 C-9A-13.16453 10.2181 Example 10C-10A-13.1145210.4177 Example 11C-11A-13.3445210.8188 Example 12C-1A-23.1545010.1174 Example 13C-2A-23.2445310.1172 Example 14C-3A-23.1545310.2171 Example 15C-4A-23.2545210.1179 Example 16C-5A-23.3945010.7172 Example 17C-6A-23.2745310.4173 Example 18C-7A-23.2145310.2182 Example 19C-8A-23.1845310.8189 Example 20C-9A-23.1645210.6182 Example 21C-10A-23.3945010.3181 Example 22C-11A-23.4845010.7189 Example 23C-1A-33.1645310.7184 Example 24C-2A-33.3945310.4181 Example 25C-3A-33.4845010.9188 Example 26C-4A-33.2145310.2180 Example 27C-5A-33.2545310.6184 Example 28C-6A-33.1545310.5181 Example 29C-7A-33.2445210.4181 Example 30C-8A-33.4845010.2184 Example 31C-9A-33.2145010.7186 Example 32C-10A-33.2545310.8181 Example 33C-11A-33.1545010.9181 Example 34C-1A-43.2445310.1184 Example 35C-2A-43.4845210.5192 Example 36C-3A-43.1645010.7194 Example 37C-4A-43.3945310.5173 Example 38C-5A-43.4845010.4182 Example 39C-6A-43.2144910.4189 Example 40C-7A-43.2545010.2182 Example 41C-8A-43.1545310.2181 Example 42C-9A-43.2445410.2184 Example 43C-10A-43.4844610.6181 Example 44C-11A-43.2144610.5189 Example 45C-1A-53.1645010.6188 Example 46C-2A-53.3945510.7191 Example 47C-3A-53.4844610.3192 Example 48C-4A-53.2144910.4191 Example 49C-5A-53.2545010.2190 Example 50C-6A-53.1545010.2193 Example 51C-7A-53.2445310.7184 Example 52C-8A-53.4844810.8199 Example 53C-9A-53.2145310.4193 Example 54C-10A-53.1845010.7191 Example 55C-11A-53.1645010.8193 Example 56C-1A-63.3945310.9201 Example 57C-2A-63.4845310.1200 Example 58C-3A-63.1645210.5203 ​​Example 59C-4A-63.3945010.7192 Example 60C-5A-63.4845010.5194 Example 61C-6A-63.2145310.4173 Example 62C-7A-63.2545310.4182 Example 63C-8A-63.1544610.2189 Example 64C-9A-63.2444910.2182 Example 65C-10A-63.4845010.2181 Example 66C-11A-63.2145010.6182 Example 67C-1B-13.2545010.5249 Example 68C-2B-13.1545310.2246 Example 69C-3B-13.2444610.1253 Example 70C-4B-13.4844910.7256 Example 71C-5B-13.1645010.4257 Example 72C-6B-13.3945010.2256 Example 73C-7B-13.4845310.8255 Example 74C-8B-13.2144810.6258 Example 75C-9B-13.2545310.3257 Example 76C-10B-13.1545010.7257 Example 77C-11B-13.2445010.7257 Example 78 C-1B-23.4845310.4255 Example 79 C-2B-23.2145210.9249 Example 80 C-3B-23.1645210.2246 Example 81 C-4B-23.3945010.6236 Example 82 C-5B-23.4845310.5246 Example 83 C-6B-23.2145210.4249 Example 84 C-7B-23.2545310.2251 Example 85 C-8B-23.1545210.7246 Example 86C-9B-23.2445010.8249 Example 87C-10B-23.4844810.9249 Example 88C-11B-23.2144810.1249 Example 89C-1B-33.1544910.5246 Example 90C-2B-33.2445010.7236 Example 91C-3B-33.4845110.5244 Example 92C-4B-33.2144610.4243 Example 93C-5B-33.1644810.2237 Example 94C-6B-33.3945310.2238 Example 95C-7B-33.4845010.2242 Example 96C-8B-33.2145310.6241 Example 97C-9B-33.2545310.5240 Example 98C-10B-33.1545210.6242 Example 99C-11B-33.2445210.7241 Example 100C-1B-43.4845010.3246 Example 101C-2B-43.2145010.4239 Example 102C-3B-43.2445310.2250 Example 103C-4B-43.4844610.2245 Example 104C-5B-43.2144910.7249 Example 105C-6B-43.2545010.8247 Example 106C-7B-43.1545010.4250 Example 107C-8B-43.2445310.7242 Example 108C-9B-43.4844810.8239 Example 109C-10B-43.1545310.9237 Example 110C-11B-43.2445310.1253 Comparative Example 1-A-14.154466.9136 Comparative Example 2-A-24.224497.2144 Comparative Example 3-A-34.214507.3137 Comparative Example 4-A-44.314507.1138 Comparative Example 5-A-54.194536.7147 Comparative Example 6-A-64.184486.8154 Comparative Example 7-B-14.414536.4147 Comparative Example 8-B-24.424506.9146 Comparative Example 9-B-34.414536.4149 Comparative Example 10-B-44.464527.1146 Comparative Example 11A-1B-14.414536.4136 Comparative Example 12A-2B-24.424506.9144 Comparative Example 13A-3B-34.414536.4137 Comparative Example 14A-4B-44.464527.1138.

[0488] As shown in Table 1 above, in the case of Examples 1 to 110, in which a combination of a first organic compound (e.g., C-1 to C-11) and a second organic compound (e.g., A-1 to B-4) according to the present invention is used as an electron transport auxiliary layer material for a blue organic EL device, it was found that the device exhibits superior performance in terms of efficiency, driving voltage, and lifespan characteristics when compared to the device of Comparative Examples 1 to 10, in which the second organic compound (A-1 to B-4) is used alone as an electron transport auxiliary layer material, and Comparative Examples 11 to 14, in which a combination of two different types of second organic compounds is used as an electron transport auxiliary layer material. In the case of an electron transport assist layer composed of a homogeneous mixture of a first organic compound (e.g., C-1 to C-11) and a second organic compound (e.g., A-1 to B-4), a new electron transport assist layer characteristic using the LUMO energy level of the first organic compound and the HOMO energy level of the second organic compound appears, and compared with Comparative Examples 1 to 10 using the LUMO energy level and HOMO energy level of the second organic compound used alone, and Comparative Examples 11 to 14 using a combination of two types of second organic compounds, it can more efficiently prevent the phenomenon of electrons and holes diffusing to other layers in the light-emitting layer, and accordingly, it can be confirmed that it is more advantageous for the overall device characteristics.

[0489]

[0490] [Example 111] Fabrication of a Blue Organic EL Device

[0491] The second organic compound A-1 synthesized in Synthesis Example 1 and the first organic compound C-1 synthesized in Synthesis Example 11 were subjected to high-purity sublimation purification by a conventionally known method and uniformly mixed in a weight ratio of 7:3, then completely dissolved in tetrahydrofuran (THF) and stirred for one day. After stirring was finished, the solvent was removed from the mixture using a spray drying method to obtain a homogeneous organic complex HOC-1, and a green organic EL device was fabricated according to the following process. At this time, compound A-1 is merely an example of the first organic compound having hole characteristics and compound C-1 is merely an example of the second organic compound having electronic characteristics, and the present invention is not limited to the types and weight ratios of the aforementioned compounds.

[0492] Specifically, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1500 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0493] An organic electroluminescent device was fabricated by stacking 98 wt% HI + 2 wt% HAT-CN6 (10 nm) / HI (140 nm) / EB (5 nm) / 98 wt% BH + 2 wt% BD (20 nm) / HOC-1 (5 nm) / ET + Liq (1:1 weight ratio) (30 nm) / LiF (1 nm) / Al (100 nm) in that order on the prepared ITO transparent electrode. At this time, the structures of HI, HAT-CN6, EB, BH, BD, ET, and Liq are as follows.

[0494]

[0495]

[0496] [Examples 112–120] Preparation of Blue Organic EL Devices

[0497] A blue organic EL device was manufactured in the same manner as in Example 111, except that instead of HOC-1 used as the electron transport auxiliary layer material in Example 111, a mixture of the first organic compound and the second organic compound of Table 2 below was used, and a homogeneous mixture HOC-2 to HOC-10 formed through the manufacturing process of Example 111 was used.

[0498]

[0499] [Examples 121–130] Fabrication of Blue Organic EL Devices

[0500] A blue organic EL device was fabricated using the same process as in Example 111, except that a mixture of the first organic compound and the second organic compound listed in Table 2 below was used instead of HOC-1, which was used as the electron transport auxiliary layer material in Example 111.

[0501]

[0502] [Evaluation Example 2: Spectroscopic Analysis]

[0503] The maximum emission wavelength was measured for each homogeneous mixture prepared in Examples 111 to 130, and the results are shown in Table 2. At this time, the maximum emission wavelength of each raw material, the first organic compound, the second organic compound, and a simple mixture thereof, was measured.

[0504]

[0505] As shown in Table 2 above, it was confirmed that the homogeneous mixture HOC-1 in the form of an organic complex of the present invention prepared in Example 111 exhibits characteristics of a maximum emission wavelength in a relatively long wavelength region when compared to its raw materials, namely the second organic compound A-1, the first organic compound C-1, and a simple mixture of said compounds A-1 and C-1 (Example 121). This proves that the homogeneous mixture formed a more electrically stable organic complex. Similarly, it was found that the homogeneous mixtures HOC-2 to HOC-10 according to Examples 112 to 120 of the present invention also exhibit characteristics of a maximum emission wavelength in a relatively long wavelength region when compared to their respective raw materials and mixtures thereof.

[0506]

[0507] [Evaluation Example 3: Evaluation of Physical Properties of Organic EL Devices]

[0508] For the blue organic EL devices fabricated in Examples 111 to 130, respectively, the driving voltage, current efficiency, and lifetime T at a current density of 10 mA / cm² 97 ...was measured, and the results are shown in Table 3 below.

[0509]

[0510] As shown in Table 3 above, in the case of Examples 111 to 120, which use organic composites HOC-1 to HOC-10 as the electron transport auxiliary layer material of a blue organic EL device, it was found that they exhibited superior performance in terms of device efficiency, driving voltage, and lifespan when compared to Examples 121 to 130, which use a simple mixture of the first and second organic mixtures as the electron transport auxiliary layer material.

Claims

1. As an electron transport auxiliary layer material disposed between the light-emitting layer and the electron transport layer of an organic electroluminescent device, The electron transport auxiliary layer material comprises at least one first organic compound and at least one second organic compound, and The above first organic compound is represented by the following chemical formula 1, and The electron transport assisting layer material, wherein the second organic compound is represented by the following chemical formula 2: [Chemical Formula 1] In the above chemical formula 1, Ar1 to Ar3 are identical or different from one another, and each independently contains hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, C1 to C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is selected from the group consisting of arylamines, or they can combine with any adjacent group to form a condensation ring, However, at least one of Ar1 to Ar3 is C6~C 60 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, R1 and R2 are identical or different from each other, and each independently consists of hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, and C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is selected from the group consisting of arylamines, or they can combine with any adjacent group to form a condensation ring, o and p are each independently integers from 0 to 3, and The alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkyloxy groups, aryloxy groups, alkylsilyl groups, arylsilyl groups, alkylboron groups, arylboron groups, alkylphosphine oxide groups, arylphosphine groups, arylphosphine oxide groups, arylamine groups, and condensation rings of the above Ar1 to Ar3 and R1 to R2 are each independently deuterium, halogen, cyano groups, nitro groups, C2 to C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C1~C 40 alkyl group of, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, and if there are multiple substituents, they are identical or different from each other. [Chemical Formula 2] In the above chemical formula 2, Multiple Xs are identical or different from one another, and each independently N or C(R 10 ) and, however, at least one of the multiple X is N, R 10 It consists of hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is selected from the group consisting of arylamines, or they may combine with any adjacent group to form a condensation ring, and the R 10 In this case of multiple individuals, multiple Rs 10 They are identical or different from each other, L is a single bond, or C6~C 18 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclei, n is an integer from 0 to 3, and Ar4 consists of hydrogen, deuterium (D), halogen, cyano group, nitro group, amino group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is selected from the group consisting of arylamines, or they can combine with any adjacent group to form a condensation ring, The arylene group and heteroarylene group of the above L, and the above R 10 and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, alkylphosphine oxide group, arylphosphine group, arylphosphine oxide group, arylamine group, and condensation ring of Ar4 are each independently deuterium, halogen, cyano group, nitro group, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C1~C 40 alkyl group of, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, and if there are multiple substituents, they are identical or different from each other.

2. In Paragraph 1, The above first organic compound is a hole-transporting compound that does not contain an electron-accepting moiety represented by the following structural formula, and The electron transport auxiliary layer material, wherein the second organic compound is an electron transport compound comprising at least one electron acceptor moiety represented by the following structural formula: In the above formula, * represents the part connected to the above chemical formula 2, and f is an integer from 0 to 3, and R 10 is as defined in Paragraph 1.

3. In Paragraph 1, An electron transport auxiliary layer material in which, in the above chemical formula 1, at least one of Ar1 to Ar3 comprises a carbazole group.

4. In Paragraph 1, An electron transport assisting layer material wherein the first organic compound is represented by any one of the following chemical formulas 1A to 1B: [Chemical Formula 1A] [Chemical Formula 1B] In the above chemical formulas 1A to 1B, Y1 and Y2 are identical or different from each other, and each independently consists of hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, and C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamines, provided that at least one of Y1 and Y2 is C6~C 60 It is Arilgi of, and R3 to R6 are identical or different from one another, and each independently hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C1~C 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group, phosphine oxide group, C1~C 40 alkylphosphine oxide group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is selected from the group consisting of arylamines, or they can combine with any adjacent group to form a condensation ring, q and t are each independently integers from 0 to 4, and r and s are each independently integers from 0 to 3, and Ar1, Ar3, R1 to R2, o and p are each as defined in Paragraph 1.

5. In Paragraph 1, The electron transport assisting layer material comprising a compound represented by any one of the following C-1 to C-11, wherein the first organic compound is:

6. In Paragraph 1, In the above chemical formula 2, Ar4 is C6~C 60 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, The above aryl group and heteroaryl group are each independently deuterium, halogen, cyano group, nitro group, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C1~C 40 alkyl group of, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 An electron transport assisting layer material that is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, and where there are multiple substituents, these are identical or different from each other.

7. In Paragraph 1, The electron transport assisting layer material, wherein the second organic compound is represented by the following chemical formula 3: [Chemical Formula 3] In the above chemical formula 3, Ar 12 and Ar 13 They are identical or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, or they may combine with any adjacent group to form a condensation ring, Y1 is O or S, and R 11 , R 12 and R 15 are identical or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C6~C 60 The aryl group of and heteroaryl groups having 5 to 60 nuclei are selected from the group consisting of, or they may combine with any adjacent group to form a condensation ring, and the R 11 and R 12 If there are multiple individuals, multiple R 11 and R 12 are identical or different from each other, a is an integer from 0 to 3, and b and e are each independently integers from 0 to 4, and The above R 11 , R 12 and R 15 Wow, the above Ar 12 and Ar 13 The alkyl groups, aryl groups, heteroaryl groups, and condensation rings are each independently deuterium, halogen, cyano group, nitro group, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C1~C 40 alkyl group of, C6~C 60 aryl group, heteroaryl group with 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 The arylphosphine oxide group and C6~C 60 It is substituted or unsubstituted with one or more substituents selected from the group consisting of arylamines, and if there are multiple substituents, they are identical or different from each other. X and n are each as defined in paragraph 1.

8. In Paragraph 7, The above second organic compound is an electron transport assisting layer material represented by any one of the following chemical formulas 3A to 3B: [Chemical Formula 3A] [Chemical Formula 3B] In the above chemical formulas 3A to 3B, Y2 is O or S, and R 13 and R 14 are identical or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C6~C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, or they may combine with any adjacent group to form a condensation ring, c is an integer from 0 to 4, and d is an integer from 0 to 3, and Ar 14 and Ar 15 They are identical or different from each other, and each independently hydrogen, deuterium (D), halogen, cyano group, C1~C 40 alkyl group of, C6~C 60 Selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei, X, Y1, R 11 , R 12 , R 15 , n, a, b and e are each as defined in Paragraph 7.

9. In Paragraph 8, The above second organic compound is an electron transport assisting layer material represented by any one of the following chemical formulas 4A to 4H: [Chemical Formula 4A] [Chemical Formula 4B] [Chemical Formula 4C] [Chemical Formula 4D] [Chemical Formula 4E] [Chemical Formula 4F] [Chemical Formula 4G] [Chemical Formula 4H] In the above chemical formulas 4A to 4H, X, Y1, Y2, R 11 to R 15 , Ar 14 or Ar 15 , a, c, d, e and n are each as defined in paragraph 8.

10. In Paragraph 1, The electron transport assisting layer material comprising a second organic compound represented by any one of A-1 to B-4 below:

11. In Paragraph 1, An electron transport auxiliary layer material in which the HOMO energy level of the first organic compound is -5.0 eV or less.

12. In Paragraph 1, An electron transport assisting layer material having a LUMO energy level of -3.0 eV or higher of the second organic compound.

13. In Paragraph 1, The electron transport assisting layer material is an electron transport assisting layer material composed of a homogeneous mixture of a first organic compound and a second organic compound that are different from each other.

14. In Paragraph 1, The above electron transport auxiliary layer material is an electron transport auxiliary layer material that does not contain metal.

15. In Paragraph 13, An electron transport assist layer material having a singlet (S1) energy of a homogeneous mixture constituting the electron transport assist layer material, wherein the singlet (S1) energy is 3.0 eV or less.

16. In Paragraph 9, An electron transport assisting layer material, wherein the maximum emission wavelength of the homogeneous mixture is formed in a longer wavelength region than the maximum emission wavelength of the first organic compound, the second organic compound, and the simple organic mixture of the first organic compound and the second organic compound.

17. An organic electroluminescent device having a structure in which a first electrode; a hole transport region; a light-emitting layer; an electron transport region and a second electrode are sequentially stacked, It includes an electron transport auxiliary layer disposed between the light-emitting layer and the electron transport region, The above electron transport auxiliary layer is an organic electroluminescent device comprising an electron transport auxiliary layer material described in any one of claims 1 to 16.

18. In Paragraph 17, An organic electroluminescent device in which the electron transport auxiliary layer is formed by depositing an electron transport auxiliary layer material through a single deposition source.

19. In Paragraph 18, An organic electroluminescent device in which the electron transport auxiliary layer material is composed of a solid-phase homogeneous mixture.

20. In Paragraph 17, The light-emitting layer comprises at least one type of host, and An organic electroluminescent device comprising: at least one host of an adjacently arranged light-emitting layer; and at least one of a first organic compound and a second organic compound of an electron transport assisting layer being different from each other.

21. In Paragraph 17, The above electron transport region includes an electron transport layer, and An organic electroluminescent device comprising: a material of an electron transport layer disposed adjacently; and at least one of a first organic compound and a second organic compound of an electron transport auxiliary layer being different from each other.

22. In Paragraph 17, The above electron transport region comprises at least one of an electron transport layer and an electron injection layer, in an organic electroluminescent device.

23. In Paragraph 17, The above-mentioned hole transport region comprises at least one of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, forming an organic electroluminescent device.

24. In Paragraph 17, The above-described organic field light-emitting device is an organic field light-emitting device having a plurality of light-emitting layer stacks, each stacking at least one light-emitting layer.

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