Organic electroluminescent device

Abstract

The present invention may provide an organic electroluminescent device comprising: a light emitting layer including multiple types of hosts and multiple types of dopants; and an electron transport auxiliary layer disposed between the light emitting layer and an electron transport region, wherein, as the aforementioned hosts, dopants, and electron transport auxiliary layer are organically controlled to have predetermined energy levels and appropriate energy gaps, respectively, driving voltage, luminescent efficiency, and lifetime characteristics of the device are optimized.

Description

organic electroluminescent devices

[0001] The present invention relates to an organic electroluminescent device comprising a light-emitting layer including a plurality of hosts and a plurality of dopants, and an electron transport auxiliary layer disposed between the light-emitting layer and an electron transport region, wherein the host, dopant, and electron transport auxiliary layer are organically controlled to have predetermined energy levels and appropriate energy gaps, respectively, thereby optimizing the driving voltage, luminous efficiency, and lifespan characteristics of the device.

[0002]

[0003] Research on organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') that led to blue electroluminescence using anthracene single crystals in 1965 continued, and in 1987, Tang proposed an organic EL device with a two-layer laminated structure consisting of a hole-producing layer (NPB) and a light-emitting layer (Alq3). Since then, in order to implement the high efficiency and long life characteristics required for commercialization, multilayer laminated structures have been proposed in which each layer has a unique and detailed function, 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 by the combination of holes and electrons. The introduction of multilayer laminated structures has improved the performance of organic EL devices to commercial characteristics, and is attempting to expand their application range to include display devices for portable information displays and TVs, starting with vehicle radio display products in 1997.

[0004] The demand for larger, higher-resolution displays is placing increasing demands on organic EL devices to improve efficiency and extend their lifespan. In particular, higher resolution, achieved by increasing the number of pixels per unit area, reduces the light-emitting area of ​​the organic EL pixels, inevitably shortening their lifespan. This has become the most critical technological challenge for organic EL devices.

[0005] When current or voltage is applied to two electrodes in 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 and emit light. At this time, 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, depending on the type of electron spin of the formed excitons.

[0006] The electron spin of excitons formed by the recombination of electrons and holes is generated as singlet excitons and triplet excitons at a ratio of 25% and 75%, respectively. The fluorescent EL device that emits light by singlet excitons cannot theoretically exceed 25% in internal quantum efficiency depending on the generation ratio, and the external quantum efficiency is accepted as the limit at 5%. The phosphorescent EL device that emits light by triplet excitons can improve the luminescence efficiency by up to four times compared to fluorescent devices when a metal complex compound containing heavy atoms of transition metals such as Ir and Pt is used as a phosphorescent dopant.

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

[0008] Research has been reported to improve the characteristics of the aforementioned organic EL devices by preventing hole diffusion into the electron transport layer and thereby increasing device stability. However, satisfactory results have not yet been achieved.

[0009]

[0010] The present invention has been devised to solve the above-mentioned problems, and has as its technical task the provision of an organic electroluminescent device that simultaneously exhibits high efficiency, low voltage, and long life by precisely controlling the light-emitting layer and the electron transport auxiliary layer to have a predetermined energy level and an appropriate energy gap therebetween.

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

[0012]

[0013] In order to achieve the above technical task, 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 laminated.

[0014] Including an electron transport auxiliary layer disposed between the above light-emitting layer and the electron transport region,

[0015] The above light-emitting layer includes different first hosts, second hosts, first dopants, and second dopants,

[0016] The above first dopant is a phosphorescent dopant containing platinum,

[0017] The second dopant is a fluorescent dopant containing boron,

[0018] The overlapping emission wavelength of the first dopant and the second dopant is 10 nm or more,

[0019] The first host (H1), the second host (H2), the first dopant (D1) and the second dopant (D2) each satisfy the conditions of the following equations (i) to (iv):

[0020] (i) HOMO H1 < 5.5 eV

[0021] (ii) HOMO H2 ≥ 5.5 eV

[0022] (iii) 440 ≤ λmax D1 ≤ 490

[0023] (iv) 450 ≤ λmax D2 ≤ 500

[0024] (In the above formula, HOMO H1 and HOMO H2 are the absolute values ​​of the HOMO energy levels of the first and second host materials, respectively, calculated according to Gaussian, and λmax D1 and λmax D2 are the maximum emission wavelengths of the first dopant material and the second dopant material, respectively.

[0025] The above electron transport auxiliary layer includes a compound represented by the following chemical formula 5,

[0026] The triplet energy (T1) of the first host H1 ), the triplet energy (T1) of the second host H2 ), and the triplet energy (T1) of the electron transport auxiliary layer aETL ) provides an organic electroluminescent device characterized by having a luminescence intensity of 2.7 eV or higher.

[0027] [Chemical Formula 5]

[0028]

[0029] In the above chemical formula 5,

[0030] Y4 to Y6 are identical or different and are each independently N or CR. 31 However, at least one of Y4 to Y6 is N,

[0031] R 12 , R 31 , Ar8 and Ar9 are the same or different from each other, and each independently represents hydrogen, deuterium, 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 40Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or can be combined with any adjacent group to form a condensed ring,

[0032] v is an integer from 1 to 4,

[0033] L is a single bond, or C6~C 18 is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms,

[0034] A is C, Si, 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60is selected from the group consisting of arylamine groups, or can be combined with any adjacent group to form a condensed ring,

[0035] The arylene group, heteroarylene group of the above L, and the above R 12 , R 31 , Ar8~Ar9 and A's alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 It may be substituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0036] In one embodiment of the present invention, the singlet energy (S1) of the first host H1 ) and the singlet energy of the second host (S1 H2 ) energies can all be greater than 3.2 eV.

[0037] In one embodiment of the present invention, the triplet energy (T1) of the first host H1 ) and the triplet of the second host (T1 H2 ) energies can all be greater than 2.8 eV.

[0038] In one embodiment according to the present invention, the mixing ratio of the first host and the second host may be a weight ratio of 2:8 to 8:2.

[0039] In one embodiment of the present invention, the first host may be a hole transporting compound that does not include an electron transporting moiety, and the second host may be an electron transporting compound that includes at least one electron transporting moiety.

[0040] In one embodiment according to the present invention, the second dopant may have an absorption wavelength that overlaps the emission wavelength of the first dopant by 10 nm or more.

[0041] In one embodiment of the present invention, the first dopant may be included in an amount of 15 wt% or less based on 100 wt% of the light-emitting layer.

[0042] In one embodiment of the present invention, the second dopant may be included in an amount of 4 wt% or less based on 100 wt% of the light-emitting layer.

[0043] In one embodiment of the present invention, the content ratio of the entire host and the entire dopant in the light-emitting layer may be a weight ratio of 70:30 to 99.5:0.5.

[0044] In one embodiment of the present invention, the electron transport auxiliary layer (aETL) may include a material satisfying the conditions of the following formulas (v) to (vii).

[0045] (v) HOMO aETL ≥ 5.5 eV

[0046] (vi) LUMO aETL ≤ 2.0 eV

[0047] (vii) T1 aETL ≥ 2.8 eV

[0048] (In the above formula, HOMO aETL , LUMO aETL and T1 aETL are the absolute value of the HOMO energy level, the absolute value of the LUMO energy level, and the triplet energy of the electron transport auxiliary layer material, respectively, calculated according to Gaussian.

[0049] In one embodiment according to the present invention, the first host (H1) and the electron transport auxiliary layer (aETL) can satisfy the condition of the following equation (viii).

[0050] (viii) HOMO aETL - HOMO H1 ≥ 0.3 eV

[0051] (In the above formula, HOMO aETL silver The absolute value of the HOMO energy level of the electron transport auxiliary layer material calculated according to Gaussian, HOMO H1 is the absolute value of the HOMO energy level of the first host material calculated according to Gaussian).

[0052] In one embodiment of the present invention, the first host (H1) and the electron transport auxiliary layer (aETL) can satisfy the condition of the following equation (ix).

[0053] (ix) LUMO aETL - LUMO H1 ≥ 0.3 eV

[0054] (In the above formula, LUMO aETL silver The absolute value of the LUMO energy level of the electron transport auxiliary layer material calculated according to Gaussian, LUMO H1 is the absolute value of the LUMO energy level of the first host material calculated according to Gaussian).

[0055] In one embodiment according to the present invention, the second host (H2) and the electron transport auxiliary layer (aETL) can satisfy the condition of the following equation (x).

[0056] (x) LUMO aETL - LUMO H2 ≤ 0.2 eV

[0057] (In the above formula, LUMO aETL silver The absolute value of the LUMO energy level of the electron transport auxiliary layer material calculated according to the Gaussian calculation formula, and LUMO H2 is the absolute value of the LUMO energy level of the second host material calculated according to Gaussian.

[0058] In one embodiment of the present invention, the electron transport region may include at least one of an electron transport layer and an electron injection layer.

[0059] 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.

[0060] In one embodiment according to the present invention, the organic electroluminescent device comprises a plurality of light-emitting layer stacks including at least one light-emitting layer, wherein the at least one light-emitting layer may include the first host, the second host, the first dopant, and the second dopant.

[0061]

[0062] According to one embodiment of the present invention, by controlling the light-emitting layer and the electron transport auxiliary layer to have properties such as predetermined HOMO energy, triplet (T1) energy, and LUMO energy, respectively, and precisely controlling the energy gap between them, an organic electroluminescent device having optimized driving voltage, luminous efficiency, and lifespan characteristics can be provided.

[0063] The effects according to the present invention are not limited to those exemplified above, and more diverse effects are included in this specification.

[0064]

[0065] FIG. 1 is a cross-sectional view showing the structure of an organic electroluminescent device according to one embodiment of the present invention.

[0066] <Explanation of symbols>

[0067] 100: Organic electroluminescent device

[0068] A: Organic layer

[0069] 10: First electrode

[0070] 20: Second electrode

[0071] 30: Hole transport region

[0072] 31: Hole injection layer

[0073] 32: Hole transport layer

[0074] 40: Emissive layer

[0075] 50: Electron transport region

[0076] 53: Electron transport auxiliary layer

[0077] 52: Electron transport layer

[0078] 51: Electron injection layer

[0079]

[0080] The advantages and features of the present invention, and the methods for achieving them, will become clearer with reference to the embodiments described in detail below 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 only 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 ambiguity in the interpretation of the present invention. Like reference numerals refer to like elements throughout the specification.

[0081] Unless otherwise defined, all terms (including technical and scientific terms) used herein may be used in their common sense to those of ordinary skill in the art to which the present invention pertains. Furthermore, terms defined in commonly used dictionaries are not to be interpreted ideally or excessively unless explicitly and specifically defined otherwise.

[0082] Furthermore, throughout the specification, when a part is said to "include" a component, this does not exclude other components, unless otherwise specifically stated, but rather means that other components may be included. Furthermore, throughout the specification, the terms "above" or "on" include not only cases where the target part is located above or below it, but also cases where there is another part in between, and do not necessarily mean that the target part is located above it in the direction of gravity. In addition, terms such as "first" and "second" in the specification do not indicate any arbitrary order or importance, but are used to distinguish between components.

[0083] In this specification, HOMO (Highest Occupied Molecular Orbital) energy, LUMO (Lowest Unoccupied Molecular Orbital) energy, triplet (T1) energy, and singlet (S1) energy each mean values ​​converted to absolute values ​​calculated according to the Gaussian calculation formula (#B3LYP / 6-31G*). In addition, in this specification, the maximum emission wavelength (λmax) means the emission wavelength range based on the maximum emission peak.

[0084] Also, in the present invention, the "number of nuclear atoms" means the number of ring atoms constituting a ring structure, and the nuclear atoms may be carbon or a heteroatom selected from the group consisting of N, O, S, and Se. For example, the number of nuclear atoms of pyridine means 6, including 5 C and 1 N constituting the pyridine ring.

[0085] In the present invention, "alkyl" means a monovalent substituent derived from a straight or branched 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.

[0086] In the present invention, "alkenyl" means a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

[0087] In the present invention, "alkynyl" means a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0088] In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms, which is a single ring or a combination of two or more rings. Furthermore, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0089] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At this time, at least one carbon atom in the ring, preferably 1 to 3 carbon atom, is substituted with a heteroatom selected from the group consisting of N, O, S, and Se. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may be included, and a form 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.

[0090] In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.

[0091] In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and may include a linear, branched, or cyclic structure. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0092] In the present invention, “arylamine” means an amine substituted with an aryl having 6 to 40 carbon atoms.

[0093] In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0094] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon atom in the ring, preferably 1 to 3 carbon atom(s), is substituted with a heteroatom such as N, O, S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

[0095] In the present invention, “alkylsilyl” means silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” means silyl substituted with aryl having 5 to 40 carbon atoms.

[0096] In the present invention, “condensed ring or condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

[0097]

[0098] Organic electroluminescent devices

[0099] Hereinafter, preferred embodiments of an organic electroluminescent device according to the present invention will be described with reference to the attached drawings. However, the 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.

[0100] 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.

[0101] Referring to FIG. 1, the organic electroluminescent device (100) includes a first electrode (10); a second electrode (20); a light-emitting layer (40) positioned between the first electrode (10) and the second electrode (20); a hole transport region (30) positioned between the first electrode (10) and the light-emitting layer (40); and an electron transport region (50) positioned between the light-emitting layer (40) and the second electrode (20), and further includes an electron transport auxiliary layer (53) between the light-emitting layer (40) and the electron transport region (50), and is characterized in that a plurality of hosts, a plurality of dopants, and the electron transport auxiliary layer (53) constituting the light-emitting layer (40) are organically controlled to have physical properties such as predetermined HOMO energy, triplet (T1) energy, LUMO energy, maximum emission wavelength, etc., and an appropriate energy gap therebetween.

[0102] Specifically, in the present invention, a light-emitting layer, an electron transport auxiliary layer, and an electron transport region are sequentially arranged, and the light-emitting layer includes, as essential components, a first host (H1) and a second host (H2) having predetermined HOMO energies, and a first dopant (D1) and a second dopant (D2) having predetermined maximum emission wavelengths, and the electron transport auxiliary layer includes a specific compound described below, and at the same time, each material of the first host, the second host, and the electron transport auxiliary layer is precisely controlled to have a specific triplet energy, for example, 2.7 eV or more, thereby optimizing the overall efficiency and lifespan characteristics of the device.

[0103] Currently, the red and green emitting layers of organic electroluminescent devices utilize phosphorescent materials, and their technology is highly mature. In contrast, blue phosphorescent materials are still under development, posing a high barrier to entry. While blue emitting layers offer significant development potential, their technological complexity is relatively high, limiting the overall performance of blue phosphorescent devices utilizing them.

[0104] Meanwhile, when the organic electroluminescent device is a blue phosphorescent device, the color purity and luminous efficiency of the device vary depending on the triplet energy levels of each material constituting the first host, the second host, and the electron transport auxiliary layer. As described above, when the triplet (T1) energy of the first host, the second host, and the electron transport auxiliary layer materials constituting the luminescent layer are all adjusted to 2.7 eV or higher, sky blue light can be emitted among blue light, and specifically, when it is 2.8 eV or higher, deep blue light with higher color purity can be emitted. Accordingly, the present invention can significantly improve the luminescence and color purity characteristics of conventional blue phosphorescent devices, which have had limitations in development.

[0105] Hereinafter, the configuration of an organic electroluminescent device (100) according to one embodiment of the present invention having the aforementioned configuration will be described in more detail.

[0106] substrate

[0107] In the organic electroluminescent device according to the present invention, the substrate 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 waterproofness of the organic electroluminescent device, it is preferable to use a glass substrate or a transparent plastic substrate.

[0108] first electrode

[0109] In the organic electroluminescent device (100) according to the present invention, the first electrode (10) is disposed on the substrate and serves as an anode that injects holes into the organic layer (A).

[0110] This first electrode (10) may be made of a material having a relatively high work function, and thus becomes an anode that injects holes into the 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 the adjacent electron transport region (50). However, this is not limited thereto, and in some cases, the first electrode (10) may become a cathode, and the second electrode (20) may become an anode.

[0111] The material forming the first electrode (10) is not particularly limited, and a conventional material known in the art can be used. Non-limiting examples thereof 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, 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.

[0112] The method for manufacturing the above first electrode (10) is not particularly limited, and can be manufactured according to a conventional method known in the art. For example, a method of coating a positive electrode material on a substrate made of a silicon wafer, quartz, glass plate, metal plate, or plastic film can be exemplified.

[0113] Second electrode

[0114] 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, and is specifically positioned on the electron transport region (50) to act as a cathode that injects electrons into the organic layer (A).

[0115] The material forming the second electrode (20) is not particularly limited, and conventional materials known in the art can be used. Non-limiting examples thereof include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; alloys thereof; and multilayered materials such as LiF / Al and LiO2 / Al.

[0116] In this case, the second electrode (20) is a (semi)transmissive 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 transmit through the second electrode (20), but may also be reflected from the lower surface of the second electrode (20), and thus may be repeatedly reflected between the upper surface of the first electrode (10) and the lower surface of the second electrode (20).

[0117] The method for manufacturing the second electrode (20) is also not particularly limited, and can be manufactured according to a method known in the art.

[0118] organic layer

[0119] The organic layer (A) included in the organic electroluminescent device according to the present invention can use a typical configuration used as an organic layer of a conventional organic EL device without limitation, and for example, can include at least one 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 above-described organic layers.

[0120] hole transport region

[0121] 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 at least one 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 a hole injection layer (31) and a hole transport layer (32).

[0122] The materials forming the aforementioned hole injection layer (31) and hole transport layer (32) are not particularly limited as long as they have a low hole injection barrier and high hole mobility, and any hole injection layer / transport layer material used in the art can be used without limitation. In this case, the materials forming the hole injection layer (31) and hole transport layer (32) may be the same or different from each other.

[0123] The hole-injecting material may be any hole-injecting material known in the art without limitation. Non-limiting examples of usable hole-injecting 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)), These include PANI / DBSA (Polyaniline / Dodecylbenzenesulfonic acid), PANI / CSA (Polyaniline / Camphor sulfonicacid), and PANI / PSS ((Polyaniline) / Poly(4-styrenesulfonate)). It can be used alone or in combination of two or more types.

[0124] In addition, the hole transport material may be any hole transport material known in the art without limitation. Non-limiting examples of hole transport materials that can be used 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), TAPC (4,4'-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), etc. These may be used alone or in combination of two or more.

[0125] The hole transport region (30) can be manufactured using a conventional method known in the art. Examples thereof include, but are not limited to, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) printing, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0126] The thickness of the hole transport region (30) can be appropriately adjusted within a conventional range known in the art, and may be, for example, from 100 Å to about 2000 Å. When 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) may be from about 50 Å to about 400 Å, and in this case, the thickness of the hole transport layer (32) may be from 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 above-described ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

[0127] luminescent layer

[0128] 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 element may vary depending on the material forming the light-emitting layer (40).

[0129] In general, a light-emitting layer is configured using a single host and dopant, or including multiple types of hosts and a single dopant, or including a single host and multiple types of dopants. In contrast, the light-emitting layer (40) of the present invention essentially includes multiple types of hosts and multiple types of dopants, and is differentiated from a conventional organic electroluminescent device in that the multiple types of hosts and the multiple types of dopants are controlled to have properties such as predetermined HOMO energy levels (HOMO), triplet (T1) energies, and / or maximum emission wavelengths.

[0130] The plurality of hosts constituting the light-emitting layer (40) of the present invention include at least two different hosts, specifically a first host (H1) and a second host (H2).

[0131] For example, the first host (H1) and the second host (H2) may satisfy the conditions of the following equations (i) and (ii), respectively.

[0132] (i) HOMO H1 < 5.5 eV

[0133] (ii) HOMO H2 ≥ 5.5 eV

[0134] In the above formula, HOMO H1 and HOMO H2 are the absolute values ​​of the HOMO energy levels of the first host material and the second host material, respectively, calculated according to Gaussian.

[0135] When the first host (H1) and the second host (H2) have the HOMO energy levels described above, the charge balance inside the light-emitting layer can be improved and efficient charge recombination characteristics can be exhibited due to the mixing of multiple hosts. Specifically, the HOMO energy level [HOMO (H1)] of the first host (H1) can be 5.4 eV or less, and the HOMO energy level [HOMO (H1)] of the second host (H2) can be 5.51 eV or more. Here, the lower limit of the HOMO energy level of the first host (H1) and the upper limit of the HOMO energy level of the second host (H2) are not particularly limited.

[0136] For another specific example, the singlet energy of the first host (S1 H1 ) and the singlet energy (S1) of the second host (H2) H2 ) can all be greater than 3.2 eV.

[0137] When the first host (H1) and the second host (H2) have the singlet (S1) energy values ​​described above, the singlet exciton generated in the light-emitting layer is prevented from diffusing to an adjacent interface and / or another layer, or the phenomenon of light emission occurring at the interface is prevented, and the singlet exciton is efficiently confined. Accordingly, the amount of excitons increases, and the light-emitting efficiency of the organic electroluminescent device can be improved. Specifically, the singlet energy (S1) of the first host (H1) H1 ) is the singlet energy (S1) of the second host (H2) H2 ) may be equal to or higher than . For example, the difference between the singlet energy of the first host (H1) and the singlet energy of the second host (H2) [Δ(S1 H1 - S1 H2 )] can be 0.01 eV or more. Here, the upper energy limits of the singlet (S1) of the first host and the second host are not particularly limited.

[0138] For another specific example, the triplet energy (T1) of the first host H1 ) and the triplet energy (T1) of the second host H2 ) can all be greater than 2.8 eV.

[0139] When the first host (H1) and the second host (H2) have the triplet (T1) energy values ​​described above, the exciton is prevented from moving to other layers, thereby increasing the efficiency of the device. Specifically, the triplet energy (T1) of the first host (H1) H1 ) is the triplet energy (T1) of the second host (H2) H2 ) may be equal to or less than. For example, the difference between the triplet energy of the first host (H1) and the triplet energy of the second host (H2) may be 0.01 eV or less, and specifically, may be 0 eV or less. Here, the lower limits of the triplet (T1) energies of the first host and the second host are not particularly limited.

[0140] In the light-emitting layer (40) according to the present invention, the content ratio of the first host (H1) and the second host (H2) can be appropriately adjusted within a range known in the art. For example, the weight ratio of the first host (H1) and the second host (H2) may be 2:8 to 8:2, specifically 3:7 to 7:3, more specifically 4:6 to 6:4, or 5:5.

[0141] As long as the first host (H1) and the second host (H2) above satisfy the above-described HOMO energy level (HOMO), singlet (S1) energy, and triplet (T1) energy properties, there are no particular limitations on the detailed composition of the compound constituting the first host and the second host, such as the type of moiety included in the compound and its bonding position, whether a linker is introduced and its bonding position, etc.

[0142] For example, the first host may be a hole transporting compound that does not include an electron transporting moiety but includes a hole transporting moiety, and the second host may be an electron transporting compound that includes at least one electron transporting moiety.

[0143] When using a conventional single host, a charge imbalance within the light-emitting layer (40) may occur due to the inherent difference in charge mobility of the material. In contrast, in the present invention, the charge balance within the light-emitting layer (40) can be improved by using a first host (H1) with high hole mobility and a second host (H2) with high electron mobility in combination.

[0144] Here, the electron transport moiety may be a conventional electron withdrawing group (EWG) known in the art, and specifically may be a monocyclic or polycyclic nitrogen-containing heteroaromatic ring (e.g., an azine group) containing at least one nitrogen (N). This electron transport moiety (EWG) may be further specified as any one selected from the following structural formula group, but is not particularly limited thereto.

[0145]

[0146] In the above formula,

[0147] * indicates a portion that is bonded to the compound. Although not specifically indicated in the structural formula above, at least one substituent known in the art (e.g., the same as the definition of R1 to R2 described below) may be substituted. In addition, although only one portion (*) that is bonded to the compound is indicated in the structural formula above, if the electron transport moiety is included as a linker, a case where 2 to 3 * portions are included also falls within the scope of the present invention.

[0148] In addition, the hole transport moiety may be a conventional electron donating group (EDG) known in the art, and may mean, for example, a conventional electron donating group (EDG) moiety that is different from the electron withdrawing group (EWG) described above and has a higher electron donating property than the electron withdrawing group (EWG).

[0149] For example, a compound that can be used as the first host (H1) can be represented by the following chemical formula 1.

[0150] [Chemical Formula 1]

[0151]

[0152] In the above chemical formula 1,

[0153] X1 is a single bond, or C, O, SNR 11 and CR12 R 13 is selected from the group consisting of,

[0154] Ar1 is hydrogen, deuterium, 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or can be combined with any adjacent group to form a condensed ring,

[0155] R1 and R2 are the same or different and each independently represent hydrogen, deuterium, 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups,

[0156] R 11 Inland R 13 are the same or different from each other, and each independently represents hydrogen, deuterium, 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or can be combined with any adjacent group to form a condensed ring,

[0157] m and o are the same or different and are each independently an integer from 0 to 4,

[0158] The above Ar1, R1~R2, R 11 ~R 13 The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, C1~C 40Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 It may be substituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0159] In a preferred specific example of the above chemical formula 1, X1 is a single bond, or C, O, SNR 11 and CR 12 R 13 is selected from the group consisting of,

[0160] Ar1 is C1~C 30 Alkyl group of C6~C 60 An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C6~C 60 is selected from the group consisting of arylsilyl groups,

[0161] R1 and R2 are the same or different and are each independently C1~C 30 Alkyl group of C6~C 60 An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C6~C 60 is selected from the group consisting of arylsilyl groups, or may be combined with any adjacent group to form a condensed ring,

[0162] R11 Inland R 13 are identical or different from each other, and each independently represents hydrogen, C1~C 30 Alkyl group of C6~C 60 An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C6~C 60 is selected from the group consisting of arylsilyl groups, or may be combined with any adjacent group to form a condensed ring,

[0163] m and o are each independently integers from 0 to 4,

[0164] The above Ar1, R1~R2, R 11 ~R 13 The alkyl group, aryl group, heteroaryl group, and arylsilyl group of each independently represent deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C6~C 60 Arylsilyl group of, and C6~C 60 It may be substituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0165] The first host represented by the chemical formula 1 described above can be further specified as compounds represented by BPH-01 to BPH-24 as exemplified below. However, the first host of the present invention is not limited to those exemplified below.

[0166]

[0167]

[0168] As another specific example, a compound that can be used as the second host (H2) can be represented by the following chemical formula 2.

[0169] [Chemical Formula 2]

[0170]

[0171] In the above chemical formula 2,

[0172] X2 is a single bond, or C, O, SNR 21 and CR 22 R 23 is selected from the group consisting of,

[0173] Y1 to Y3 are identical or different and are each independently N or CR. 24 and at least one of Y1 to Y3 contains N,

[0174] Ar2 and Ar3 are the same or different from each other, and each independently represents hydrogen, deuterium, 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or can be combined with any adjacent group to form a condensed ring,

[0175] R3 and R4 are the same or different and each independently represent hydrogen, deuterium, 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 40Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 Selected from the group consisting of arylamine groups,

[0176] R 21 Inland R 24 are identical or different from each other, and each independently represents hydrogen, deuterium, 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or can be combined with any adjacent group to form a condensed ring,

[0177] p and q are equal to or different from each other and are each independently an integer from 0 to 4,

[0178] The above Ar2~Ar3, R3~R4, R 21 ~R 24 The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 It may be substituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0179] In a preferred specific example of the above chemical formula 2, X2 is a single bond, or C, O, SNR 21 and CR 22 R 23 is selected from the group consisting of,

[0180] Y1 to Y3 are identical or different and are each independently N or CR. 24 , and at least one of Y1 to Y3 is N,

[0181] Ar2 and Ar3 are the same or different, and are each independently C1~C 30 Alkyl group of C6~C 60 An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C6~C 60 is selected from the group consisting of arylsilyl groups,

[0182] R3 and R4 are the same or different and are each independently C1~C 30 Alkyl group of C6~C 60 An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C6~C 60 is selected from the group consisting of arylsilyl groups, or may be combined with any adjacent group to form a condensed ring,

[0183] R 21 Inland R 24 are identical or different from each other, and each independently represents hydrogen, C1~C 30 Alkyl group of C6~C 60 An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C6~C 60 is selected from the group consisting of arylsilyl groups, or may be combined with any adjacent group to form a condensed ring,

[0184] p and q are each independently integers from 0 to 4,

[0185] The above Ar2~Ar3, R3~R4, R 21 ~R 24 The alkyl group, aryl group, heteroaryl group, and arylsilyl group of each independently represent deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C6~C 60 Arylsilyl group of, and C6~C 60 It may be substituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0186] The second host represented by the chemical formula 2 described above can be further specified as compounds represented by BNH-01 to BNH-24 as exemplified below. However, the second host of the present invention is not limited to those exemplified below.

[0187]

[0188]

[0189] The light-emitting layer (40) of the present invention includes two or more different dopants, a first dopant (D1) and a second dopant (D2). Specifically, the first dopant (D1) and the second dopant (D2) have different light-emitting wavelength ranges centered on the maximum light-emitting peak, but at least a portion of these light-emitting wavelength ranges overlap.

[0190] For example, the maximum emission wavelength (λmax) of the first dopant (D1) D1 ) is 440 nm to 490 nm, and the maximum emission wavelength (λmax) of the second dopant (D2) D2 ) is 450 nm to 500 nm, and the emission wavelengths of the first dopant and the second dopant include an identical wavelength region that overlaps by 10 nm or more. For example, the long wavelength section of the first dopant (D1) and the short wavelength section of the second dopant (D2) may overlap by 10 nm or more, and specifically, the emission wavelength of the first dopant and the absorption wavelength of the second dopant overlap by 10 nm or more.

[0191] The first dopant (D1) and the second dopant (D2) may be dopants commonly used in the art. Specifically, the first dopant (D1) may be a phosphorescent dopant, and the second dopant (D2) may be a fluorescent dopant or a thermally activated delayed fluorescence (TADF) dopant. Here, the delayed fluorescence dopant (TADF) refers to a material that causes a triplet (T1) exciton to annihilate into a singlet (S1) exciton through reverse intersystem crossing (REX) and then emits fluorescence (e.g., T1 -> S1 -> S0).

[0192] Typically, holes and electrons meet to generate excitons, of which 25% are singlet (S1) excitons and 75% are triplet (T1) excitons. Singlet (S1) excitons emit light through fluorescence (S1 -> S0), but the fluorescence efficiency is very low. Accordingly, most organic electroluminescent devices utilize light emission through phosphorescence (T1 -> S0) of highly efficient triplet excitons, and the internal quantum efficiency (IQE) of this phosphorescence emission is up to about 75%.

[0193] In contrast, when the first dopant that emits phosphorescence and the second dopant that emits fluorescence are mixed and adjusted to appropriate physical properties as in the present invention, 75% of phosphorescence emission and 25% of fluorescence emission can be utilized through reverse intersystem transition, so that the internal quantum efficiency of the device can be increased to 100%, and the efficiency characteristics of the device can be significantly improved.

[0194] In the light-emitting layer (40) according to the present invention, the first dopant (D1) may be included in an amount of 15 wt% or less, specifically 13 wt% or less, and more specifically 12 wt% or less, based on 100 wt% of the light-emitting layer. In addition, the second dopant (D2) may be included in an amount of 4 wt% or less, specifically 3.5 wt% or less, and more specifically 3 wt% or less, based on 100 wt% of the light-emitting layer. At this time, the lower limit of the content of the first dopant and the second dopant is not particularly limited, and may be, for example, greater than 0 wt%.

[0195] In addition, the content ratio of the first dopant (D1) and the second dopant (D2) can be appropriately adjusted within a range known in the art. For example, the weight ratio of the first dopant (D1) and the second dopant (D2) can be 9.5:0.5 to 7:3, and specifically, the weight ratio can be 9:1 to 7.5:2.5.

[0196] As long as the first dopant (D1) and the second dopant (D2) above satisfy the above-described maximum emission wavelength (λmax) and their overlapping wavelength range properties, there are no particular limitations on the detailed composition of the compound constituting the first dopant and the second dopant, such as the type of moiety included in the compound and its bonding position, whether a linker is introduced and its bonding position, etc.

[0197] For example, the first dopant (D1) is a phosphorescent dopant comprising a metal (M), for example, platinum (Pt). Specifically, the first dopant may be an organic complex comprising platinum (Pt). The metal may be a transition metal capable of forming multidentate chemical bonds with organic substances (e.g., ligands), including platinum. In this case, the chemical bonds include conventional bonds known in the art, and for example, may be at least one of a covalent bond and a coordinate bond.

[0198] For example, a compound that can be used as the first dopant (D1) can be represented by the following chemical formula 3.

[0199] [Chemical Formula 3]

[0200]

[0201] In the above chemical formula 3,

[0202] M is a metal atom capable of two covalent bonds and two coordinate bonds, and is platinum (Pt).

[0203] R5 to R7 are the same or different and each independently represent a single bond, O, S, C2~C 30 alkylene group, C6~C 18 is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms,

[0204] B, C, D and E are the same or different from each other and each independently represent hydrogen, deuterium, 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups,

[0205] However, at least one of B, C, D and E comprises a moiety represented by 3A below,

[0206] [Chemical Formula 3A]

[0207]

[0208] In the above chemical formula 3A,

[0209] * indicates the position where it combines with M,

[0210] r can be an integer from 0 to 4,

[0211] R8 is hydrogen, deuterium, 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or may be combined with any adjacent group to form a condensed ring, wherein when r is 2 or more, multiple R8s are the same or different from each other,

[0212] Ar4 and Ar5 are the same or different from each other, and each independently represents hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C40 Cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or can form a condensed ring with any one selected from adjacent B, C, D and E,

[0213] G is C6~C 60 Aryl group of C6~C 60 is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclear atoms, wherein when r is 2 or more, multiple Gs are the same or different from each other,

[0214] B, C, D, E of the above chemical formula 3, and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group of R8, Ar4~Ar5 in the above chemical formula 3A; and the aryl group, arylene group and heteroarylene group of G in the above chemical formula 3A; each independently represent deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 It may be substituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0215] A preferred specific example of the above chemical formula 3 and chemical formula 3A is that M is platinum,

[0216] R5 to R7 are each independently a single bond or O,

[0217] B, C, D and E are each independently C6~C 60 An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C6~C 60 is selected from the group consisting of arylsilyl groups, provided that at least one of B, C, D and E comprises a moiety represented by 3A below,

[0218] R8 is C1~C 30 Alkyl group of C6~C 60 An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C6~C 60 is selected from the group consisting of arylsilyl groups, or may be combined with any adjacent group to form a condensed ring,

[0219] Ar4 and Ar5 can each independently form a condensed ring with any one selected from adjacent B, C, D and E, provided that when Chemical Formula 3A is B or E, C1~C 30 Alkyl group of C6~C 60 An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C6~C60 is selected from the group consisting of arylsilyl groups, or may be combined with any adjacent group to form a condensed ring,

[0220] G is C6~C 60 Aryl group of C6~C 60 It can be selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclear atoms, and when r is 2 or more, multiple Gs are the same or different from each other,

[0221] B, C, D, E of the above chemical formula 3, and the alkyl group, aryl group, heteroaryl group, arylsilyl group of R8, Ar4~Ar5 in the above chemical formula 3A; and the aryl group, arylene group, and heteroarylene group of G in the above chemical formula 3A; each independently represent deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C6~C 60 Arylsilyl group of, and C6~C 60 It may be substituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0222] The first dopant (D1) represented by the chemical formula 3 described above can be further specified as a compound represented by PTB-01 to PTB-10 as exemplified below. However, the first dopant of the present invention is not limited to those exemplified below.

[0223]

[0224] Additionally, the second dopant (D2) may be a fluorescent dopant containing boron (B), and specifically, one having an absorption wavelength that overlaps the emission wavelength of the first dopant by 10 nm or more may be used.

[0225] For example, a compound that can be used as a second dopant (D2) can be represented by the following chemical formula 4.

[0226] [Chemical Formula 4]

[0227]

[0228] In the above chemical formula 4,

[0229] R9 to R 11 , Ar6 and Ar7 are the same or different from each other, and each independently represents hydrogen, deuterium, 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or can be combined with any adjacent group to form a condensed ring,

[0230] s and t are integers from 0 to 4, respectively.

[0231] u is an integer from 0 to 3,

[0232] R9~R above 11, Ar6~Ar7, alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40 A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 It may be substituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0233] A preferred specific example of the above chemical formula 4 is R9 to R 11 , Ar6 and Ar7 are the same or different from each other, and are each independently C1~C 30 Alkyl group of C6~C 60 An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C6~C 60 is selected from the group consisting of arylsilyl groups, or may be combined with any adjacent group to form a condensed ring,

[0234] When s is 0, R9 is hydrogen, and when s is not 0, it may have any of the aforementioned substituents except hydrogen without limitation. The same may also apply to t and u. Specifically, s, t, and u may each be an integer from 0 to 2.

[0235] R9~R above 11 , Ar6~Ar7, alkyl group, aryl group, heteroaryl group, arylsilyl group are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C6~C 60 Arylsilyl group of, and C6~C 60 It may be substituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0236] The second dopant (D2) represented by the chemical formula 4 described above can be further specified as compounds represented by BD-01 to BD-10 as exemplified below. However, the second dopant of the present invention is not limited to those exemplified below.

[0237]

[0238] The light-emitting layer (40) according to the present invention is configured to include the first host (H1), the second host (H2), the first dopant (D1), and the second dopant (D2) described above. At this time, the mixing ratio thereof can be appropriately adjusted within a range known in the art. For example, the content ratio of the entire host and the entire dopant in the light-emitting layer (40) may be a weight ratio of 70:30 to 99.5:0.5, specifically, a weight ratio of 75:25 to 97:3, and more specifically, a weight ratio of 80:20 to 95:5.

[0239] The aforementioned light-emitting layer (40) may be formed as a single layer composed of a plurality of different hosts and dopants, or as multiple layers of two or more. For example, when the light-emitting layer is composed of multiple layers, the organic electroluminescent device can emit light of various colors. 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 remains constant, thereby providing an organic electroluminescent device with improved light-emitting efficiency corresponding to the number of light-emitting layers.

[0240] The above-mentioned light-emitting layer (40) can be manufactured by a conventional method known in the art. Examples thereof include, but are not limited to, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0241] In addition, the thickness of the light-emitting layer (40) can be appropriately adjusted within a conventional range known in the art, and for example, can be from 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.

[0242] 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.

[0243] The plurality of light-emitting layers included in the light-emitting stack may be light-emitting layers that each emit light of a different color, or light-emitting layers that emit light of the same color. That is, the light-emitting color may vary depending on the material that constitutes the light-emitting layer. For example, the plurality of light-emitting stacks may include materials that emit light of blue, green, red, yellow, white, etc., and may be formed using a phosphorescent or fluorescent material. In this case, the colors exhibited by each light-emitting layer may be complementary to each other. In addition, the color may be selected as a combination of colors that can emit white light. Each of the light-emitting layers may include phosphorescent dopants or fluorescent dopants corresponding to the selected color, respectively.

[0244] For example, at least one of the plurality of light-emitting layers may include the first host, the second host, the first dopant, and the second dopant described above.

[0245] In addition, although not shown in the drawing, the organic electroluminescent device (100) may further include a charge generation layer (not shown) that is arranged between adjacent stacks among a plurality of light-emitting stacks and connects them.

[0246] A charge generation layer (CGL) is a layer that separates adjacently arranged light-emitting stacks without directly contacting positive electrodes (e.g., anode and cathode) in an organic light-emitting device having multiple light-emitting stacks. The charge generation layer is arranged between two adjacent light-emitting stacks, and acts as a cathode by generating electrons for one light-emitting stack and as an anode by generating holes for the other light-emitting stack. 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. In addition, the charge generation layer may be formed by doping a material known in the art with a conventional n-type material and / or p-type material.

[0247] electron transport auxiliary layer

[0248] The organic electroluminescent device according to the present invention includes an electron transport auxiliary layer (53) disposed between the light-emitting layer (40) and the electron transport region (50).

[0249] This electron transport auxiliary layer (53) serves to more efficiently transfer electrons transferred from the electron transport region (50) described below, for example, the electron transport layer (52), to the light-emitting layer (40), while simultaneously confining excitons generated within the light-emitting layer (40) and preventing excess holes within the light-emitting layer (40) from being transferred to the electron transport region (50), for example, the electron transport layer (52). Accordingly, in the present invention, not only can the light-emitting efficiency in the light-emitting layer (40) be increased, but also hole leakage from the light-emitting layer (40) to the electron transport region (50) can be prevented, thereby improving the lifespan characteristics of the device.

[0250] In particular, the electron transport auxiliary layer (53) according to the present invention is differentiated from the conventional organic electroluminescent device in that it not only has properties such as a predetermined HOMO energy (HOMO), LUMO energy (LUMO), and triplet (T1) energy, but also organically and precisely controls an appropriate energy gap compared to the light-emitting layer (40) including both the aforementioned multiple types of hosts and multiple types of dopants.

[0251] For example, the electron transport auxiliary layer (53) may satisfy the following equations (v) to (vii).

[0252] (v) HOMO aETL ≥ 5.5 eV

[0253] (vi) LUMO aETL ≤ 2.0 eV

[0254] (vii) T1 aETL ≥ 2.8 eV

[0255] In the above formula, HOMO aETL , LUMO aETLand T1 aETL are the absolute value of the HOMO energy level, the absolute value of the LUMO energy level, and the triplet energy of the electron transport auxiliary layer material, respectively, calculated according to Gaussian.

[0256] The electron transport auxiliary layer (53) has the HOMO energy level (HOMO) mentioned above. aETL ) value, it is possible to block the phenomenon that the holes transferred to the light-emitting layer (40) diffuse or pass over to the electron transport region (50), for example, the electron transport layer (52). Accordingly, the probability of recombination where holes and electrons meet inside the light-emitting layer (40) can be increased, thereby further increasing the luminous efficiency of the organic electroluminescent device. In addition, it is possible to improve the lifespan characteristics of the device by resolving the irreversible decomposition reaction due to oxidation and the resulting decrease in the lifespan of the organic electroluminescent device when the holes diffuse or move over the light-emitting layer (40) to the electron transport layer (52). Specifically, the absolute value of the HOMO energy level of the electron transport auxiliary layer (53) (HOMO aETL ) is 5.51 eV or more, and more specifically, may be 5.2 eV or more. Here, the upper limit of the HOMO energy of the electron transport auxiliary layer (53) is not particularly limited.

[0257] Electrons move along the LUMO energy level. The electron transport layer (53) moves along the LUMO energy level (LUMO) mentioned above. aETL ) has a numerical value, the electrons transferred from the electron transport region (50) can smoothly move to the light-emitting layer (40), so that the efficiency of the organic electroluminescent device can be increased. Specifically, the absolute value of the LUMO energy level of the electron transport auxiliary layer (53) (LUMO aETL ) is 1.97 eV or less, and more specifically, may be 1.95 eV or less. Here, the lower limit of the LUMO energy of the electron transport auxiliary layer (53) is not particularly limited.

[0258] In addition, when the electron transport auxiliary layer (53) has the triplet (T1) energy value described above, it is possible to prevent excitons in the light-emitting layer (40) from moving to other layers, thereby significantly increasing the efficiency of the organic electroluminescent device. Specifically, the triplet (T1) energy of the electron transport auxiliary layer (53) may be 2.81 eV or more. Here, the upper limit of the triplet (T1) energy of the electron transport auxiliary layer (53) is not particularly limited.

[0259] For another specific example, the first host (H1) and the electron transport auxiliary layer (53) included in the light-emitting layer (40) can satisfy the following equation (viii).

[0260] (viii) HOMO aETL - HOMO H1 ≥ 0.3 eV

[0261] In the above formula, HOMO aETL silver The absolute value of the HOMO energy level of the electron transport auxiliary layer material calculated according to Gaussian, HOMO H1 is the absolute value of the HOMO energy level of the first host material calculated according to Gaussian.

[0262] When the difference between the absolute value of the HOMO energy level of the electron transport auxiliary layer (53) and the absolute value of the HOMO energy level of the first host (H1) is in the above-mentioned range, the HOMO of the electron transport auxiliary layer (53) is formed deep, so that it can have sufficient electrical properties to prevent excess holes in the light-emitting layer from moving to the electron transport layer (Hole Block) and to efficiently confine excitons within the light-emitting layer. Specifically, the absolute value of the HOMO energy level of the electron transport auxiliary layer (HOMO aETL ) and the absolute value of the HOMO energy level of the first host (H1) included in the light-emitting layer (40) (HOMO H1 ) can be more than 0.32 eV.

[0263] For another specific example, the first host (H1) and the electron transport auxiliary layer (53) included in the light-emitting layer (40) can satisfy the following equation (ix).

[0264] (ix) LUMO aETL - LUMO H1 ≥ 0.3 eV

[0265] In the above formula, LUMO aETL silver The absolute value of the LUMO energy level of the electron transport auxiliary layer material calculated according to Gaussian, LUMO H1 is the absolute value of the LUMO energy level of the first host material calculated according to Gaussian.

[0266] When the difference between the absolute value of the LUMO energy level of the electron transport auxiliary layer (53) and the absolute value of the LUMO energy level of the first host (H1) is in the above-mentioned range, since the LUMO energy level of the first host (H1) is sufficiently high, it helps the electrons transferred from the electron transport auxiliary layer (53) to be smoothly transferred to the second host (H2) without being transferred to the first host (H1), and at the same time, it prevents the electrons from leaving the light-emitting layer (40) and flowing to the hole transport region (30), thereby improving the efficiency characteristics and lifespan characteristics of the device at the same time. Specifically, the absolute value of the LUMO energy level of the electron transport auxiliary layer (53) (LUMO aETL ) and the absolute value of the LUMO energy level of the first host (H1) included in the light-emitting layer (40) (LUMO H1 ) can be more than 0.5 eV.

[0267] For another specific example, the second host (H2) and the electron transport auxiliary layer (53) included in the light-emitting layer (40) can satisfy the following equation (x).

[0268] (x) LUMO aETL - LUMO H2 ≤ 0.2 eV

[0269] In the above formula, LUMOaETL Is The absolute value of the LUMO energy level of the electron transport auxiliary layer material calculated according to the Gaussian calculation formula, and LUMO H2 is the absolute value of the LUMO energy level of the second host material calculated according to Gaussian.

[0270] When the difference between the absolute value of the LUMO energy level of the electron transport auxiliary layer (53) and the absolute value of the LUMO energy level of the second host (H2) is within the above-mentioned range, since the LUMO energy level of the second host (H2) is lower than that of the electron transport auxiliary layer (53), electrons are smoothly transferred from the electron transport region (50) to the light-emitting layer (40), which has a favorable effect on the driving voltage characteristics of the device. Specifically, the absolute value of the LUMO energy level of the electron transport auxiliary layer (53) (LUMO aETL ) and the absolute value of the LUMO energy level of the second host (H2) included in the light-emitting layer (40) (LUMO H2 ) may be less than 0.19 eV. This can be judged as a value of an energy level that is easy to transfer electrons from one layer to another while sufficiently increasing the electron density at the interface between the electron transport auxiliary layer (53) and the light-emitting layer (40).

[0271] The electron transport auxiliary layer (53) according to the present invention has the HOMO energy (HOMO) described above. aETL ), LUMO energy (LUMO aETL ), triplet (T1 aETL ) If the energy gap properties and the appropriate energy gap properties compared to the host included in the light-emitting layer (40) are satisfied, the detailed composition of the compound constituting the electron transport auxiliary layer (53), such as the type of moiety included in the compound and its bonding position, whether a linker is introduced and its bonding position, etc., are not particularly limited.

[0272] For example, the electron transport auxiliary layer (53) may include an electron transport compound that is different from the second host (H2) and includes at least one conventional electron transport moiety known in the art.

[0273] For example, the electron transport auxiliary layer (53) may include a compound represented by the following chemical formula 5.

[0274] [Chemical Formula 5]

[0275]

[0276] In the above chemical formula 5,

[0277] Y4 to Y6 are identical or different and are each independently N or CR. 31 However, at least one of Y4 to Y6 is N,

[0278] R 12 , R 31 , Ar8 and Ar9 are the same or different from each other, and each independently represents hydrogen, deuterium, 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or can be combined with any adjacent group to form a condensed ring,

[0279] v is an integer from 1 to 4,

[0280] L is a single bond, or C6~C 18 is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms,

[0281] A is C, Si, 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 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group, C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or can be combined with any adjacent group to form a condensed ring,

[0282] The arylene group, heteroarylene group of the above L, and the above R 12 , R 31 , Ar8~Ar9 and A's alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group, C2~C 40 Alkynyl group, C3~C 40A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 It may be substituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0283] In a preferred specific example of the above chemical formula 5, Y4 to Y6 are the same or different from each other, and each independently represents N or CR. 31 However, at least one of Y4 to Y6 is N,

[0284] R 12 , R 31 , Ar8 and Ar9 are the same or different from each other, and are each independently C1~C 30 Alkyl group of C6~C 60 An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C6~C 60 is selected from the group consisting of arylsilyl groups, or may be combined with any adjacent group to form a condensed ring,

[0285] L is a single bond, or C6~C 18 is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms,

[0286] A is C, Si, C6~C 60 An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, and a C6~C 60It may be selected from the group consisting of arylsilyl groups, or may be combined with any adjacent group to form a condensed ring, and may be specifically selected from C, Si, benzene, naphthalene, dibenzofuran, etc.

[0287] v is an integer from 1 to 4, but when A is C or Si, v is 4, and when A is the above-mentioned substituent other than C and Si, v is an integer from 1 to 3,

[0288] The arylene group, heteroarylene group of the above L, and the above R 12 , R 31 , Ar8~Ar9 and the alkyl group, aryl group, heteroaryl group and arylsilyl group of A are each independently selected from the group consisting of deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C6~C 60 Aryl group of, heteroaryl group of 5 to 60 nuclear atoms, C6~C 60 Arylsilyl group of, and C6~C 60 It may be substituted with one or more substituents selected from the group consisting of arylamine groups, and in this case, when there are multiple substituents, they may be the same or different from each other.

[0289] The compound constituting the electron transport auxiliary layer (53) represented by the chemical formula 5 described above can be further specified as a compound represented by ETA-1 to ETA-24 as exemplified below. However, the electron transport auxiliary layer material of the present invention is not limited to those exemplified below.

[0290]

[0291]

[0292] The above electron transport auxiliary layer (53) can be manufactured using a conventional method known in the art. Examples thereof include, but are not limited to, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) printing, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0293] In addition, the thickness of the electron transport auxiliary layer (53) can be appropriately adjusted within a conventional range known in the art, and for example, can be from about 50 Å to about 200 Å. When the thickness of the electron transport auxiliary layer (53) satisfies the range described above, not only can the luminescence efficiency of the light-emitting layer be increased, but hole leakage from the light-emitting layer to the electron transport region can be prevented, thereby securing an effect of increasing the efficiency and lifespan characteristics of the device.

[0294] 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 broad sense, it can be understood as being included in a part of the electron transport region (50) described later.

[0295] electron transport region

[0296] 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).

[0297] This electron transport region (50) may include at least one of an electron transport layer (52) and an electron injection layer (51). At this time, considering the characteristics of the organic electroluminescent device, it is preferable to include an electron transport layer (52) and an electron injection layer (51).

[0298] This electron transport layer (53) can be formed using any material known in the art with conventional electron transport properties without limitation. For example, it can include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), and heterocyclic derivatives containing nitrogen.

[0299] The electron transport region (50) according to the present invention, specifically the electron injection layer, may be co-deposited with an n-type dopant 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 thereof include alkali metals, alkaline earth metals, or rare earth metals.

[0300] The above electron transport region (50) can be manufactured using a conventional method known in the art. Examples thereof include, but are not limited to, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) printing, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0301] 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 above-described range, a satisfactory level of electron transport characteristics can be obtained without a substantial increase in driving voltage.

[0302] luminescent auxiliary layer

[0303] The organic light-emitting device (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).

[0304] The light-emitting auxiliary layer transports holes moving from the hole transport region (30) to the light-emitting layer (30), and also controls the thickness of the organic layer (A). This light-emitting auxiliary layer has a high LUMO value, which prevents electrons from moving to the hole transport layer, and has a high triplet energy, which prevents excitons in the light-emitting layer from diffusing to the hole transport layer.

[0305] These light-emitting auxiliary layers 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 the red, green, and blue organic light-emitting devices may be made of the same material.

[0306] The material of the light-emitting auxiliary layer is not particularly limited, and examples thereof 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, MTDATA (4, 4', 4″-Tris(N-3-methylphenyl-Nphenyl-amino)- triphenylamine), etc. 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 above-mentioned materials. As the p-type dopant, a known p-type dopant used in the relevant technical field may be used.

[0307] capping layer

[0308] 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.

[0309] The capping layer may include 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), 1,1′-bis(di-4-tolylaminophenyl) cyclohexane (TAPC).

[0310] The capping layer may be a single layer, or may include two or more layers having different refractive indices, such that the refractive index gradually changes as it passes through the two or more layers.

[0311] The above capping layer can be manufactured by a conventional method known in the art, and various methods such as vacuum deposition, spin coating, casting, or LB (Langmuir-Blodgett) method can be used, for example.

[0312] The organic electroluminescent device (100) of the present invention including the above-described configuration can be manufactured according to a conventional method 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 sequentially 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 on the anode.

[0313] 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 laminated, 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 life characteristics because the half-life time of the initial brightness is increased while maintaining the maximum luminous efficiency when voltage, current, or both are applied.

[0314] Hereinafter, the present invention will be described in detail through examples. However, the following examples are only illustrative of the present invention, and the present invention is not limited to the following examples.

[0315]

[0316] <First Host Synthesis>

[0317] [Synthesis Example 1] Synthesis of BPH-01

[0318]

[0319] Under a nitrogen stream, 9-([1,1'-biphenyl]-3-yl)-9H,9'H-3,3'-bicarbazole (4.84 g, 10 mmol), (3-bromophenyl)triphenylsilane (4.15 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), P(t-Bu)3 (0.47 ml, 2 mmol), NaO(t-Bu) (1.92 g, 20 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 3 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then column chromatography was used to obtain the target compound BPH-01 (3.76 g, yield 46%).

[0320] Mass: [(M+H) + ] : 819

[0321]

[0322] [Synthesis Example 2] Synthesis of BPH-02

[0323]

[0324] Under a nitrogen stream, 9-phenyl-9H,9'H-3,3'-bicarbazole (4.08 g, 10 mmol), (3-bromophenyl)triphenylsilane (4.15 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), P(t-Bu)3 (0.47 ml, 2 mmol), NaO(t-Bu) (1.92 g, 20 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 3 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then column chromatography was used to obtain the target compound BPH-02 (3.49 g, yield 47%).

[0325] Mass: [(M+H) + ] : 743

[0326]

[0327] [Synthesis Example 3] Synthesis of BPH-03

[0328]

[0329] Under a nitrogen stream, 4-(9H-carbazol-3-yl)-N,N-diphenylaniline (4.10 g, 10 mmol), (3-bromophenyl)triphenylsilane (4.15 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), P(t-Bu)3 (0.47 ml, 2 mmol), NaO(t-Bu) (1.92 g, 20 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 3 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then column chromatography was used to obtain the target compound BPH-03 (3.65 g, yield 49%).

[0330] Mass: [(M+H) + ] : 745

[0331]

[0332] [Synthesis Example 4] Synthesis of BPH-04

[0333]

[0334] Under a nitrogen stream, 3'-phenyl-9H-3,9'-bicarbazole (4.08 g, 10 mmol), (3-bromophenyl)trimethylsilane (2.29 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), P(t-Bu)3 (0.47 ml, 2 mmol), NaO(t-Bu) (1.92 g, 20 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 3 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then column chromatography was used to obtain the target compound BPH-04 (2.33 g, yield 42%).

[0335] Mass: [(M+H) + ] : 556

[0336]

[0337] [Synthesis Example 5] Synthesis of BPH-05

[0338]

[0339] (3,5-di(9H-carbazol-9-yl)phenyl)boronic acid (4.52 g, 10 mmol), (3-bromophenyl)trimethylsilane (2.29 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100°C for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound BPH-05 (3.06 g, yield 55%) was obtained using column chromatography.

[0340] Mass: [(M+H) + ] : 556

[0341]

[0342] [Synthesis Example 6] Synthesis of BPH-06

[0343]

[0344] 9-(3-bromophenyl)-9H-carbazole (3.22 g, 10 mmol) was dissolved in an excess of THF, the temperature was lowered to -78℃, and 2.5 M n-BuLi (1 eq) was added dropwise to obtain reactant-1. 9-(3-bromophenyl)-3-phenyl-9H-carbazole (3.98 g, 10 mmol) was dissolved in an excess of THF in another flask, the temperature was lowered to -78℃, 2.5 M n-BuLi (1 eq) was added dropwise, and the mixture was stirred for 3 hours, after which dichlorodiphenylsilane (2.53 g, 10 mmol) was added to obtain reactant-2. To the generated reactant-2, the previously generated reactant-1 was added dropwise, and the mixture was slowly warmed to room temperature and stirred for 10 hours. After the reaction was completed, water was added and extracted to remove the solvent in the organic layer, and then silica column chromatography was used to obtain the target compound BPH-06 (2.45 g, yield 33%).

[0345] Mass: [(M+H) + ] : 743

[0346]

[0347] [Synthesis Example 7] Synthesis of BPH-07

[0348]

[0349] 3-bromo-9-(3-(triphenylsilyl)phenyl)-9H-carbazole (5.80 g, 10 mmol), (7-(naphthalen-2-yl)-7H-benzo[c]carbazol-10-yl)boronic acid (3.87 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 1,4-dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, compound BPH-07 (4.29 g, yield 51%) was obtained using column chromatography.

[0350] Mass: [(M+H) + ] : 843

[0351]

[0352] [Synthesis Example 8] Synthesis of BPH-08

[0353]

[0354] Under a nitrogen stream, (3-bromophenyl)triphenylsilane (4.15 g, 10 mmol), 5-phenyl-5,7-dihydroindolo[2,3-b]carbazole (3.32 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), P(t-Bu)3 (0.47 ml, 2 mmol), NaO(t-Bu) (1.92 g, 20 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 3 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then column chromatography was used to obtain the target compound BPH-08 (3.20 g, yield 48%).

[0355] Mass: [(M+H) + ] : 666

[0356]

[0357] [Synthesis Example 9] Synthesis of BPH-09

[0358]

[0359] Under a nitrogen stream, (3-bromophenyl)triphenylsilane (4.15 g, 10 mmol), 5-(naphthalen-2-yl)-5,7-dihydroindolo[2,3-b]carbazole (3.82 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), P(t-Bu)3 (0.47 ml, 2 mmol), NaO(t-Bu) (1.92 g, 20 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 3 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then column chromatography was used to obtain the target compound BPH-09 (3.22 g, yield 45%).

[0360] Mass: [(M+H) + ] : 716

[0361]

[0362] [Synthesis Example 10] Synthesis of BPH-10

[0363]

[0364] Under a nitrogen stream, (3-bromophenyl)triphenylsilane (4.15 g, 10 mmol), 7-phenyl-7H,7'H-10,10'-bibenzo[c]carbazole (5.08 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), P(t-Bu)3 (0.47 ml, 2 mmol), NaO(t-Bu) (1.92 g, 20 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 3 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then column chromatography was used to obtain the target compound BPH-10 (3.54 g, yield 42%).

[0365] Mass: [(M+H) + ] : 843

[0366]

[0367] [Synthesis Example 11] Synthesis of BPH-11

[0368]

[0369] Under a nitrogen stream, (3-bromophenyl)di(naphthalen-2-yl)(phenyl)silane (5.15 g, 10 mmol), 9-phenyl-9H,9'H-3,3'-bicarbazole (4.08 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), P(t-Bu)3 (0.47 ml, 2 mmol), NaO(t-Bu) (1.92 g, 20 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 3 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then column chromatography was used to obtain the target compound BPH-11 (3.37 g, yield 40%).

[0370] Mass: [(M+H) + ] : 843

[0371]

[0372] [Synthesis Example 12] Synthesis of BPH-12

[0373] <Step 1> Synthesis of (3-bromophenyl)tri(naphthalen-2-yl)silane

[0374]

[0375] 1,3-dibromobenzene (2.35 g, 10 mmol) was dissolved in an excess of THF, the temperature was lowered to -78°C, and 2.5 M n-BuLi (1 eq) was added dropwise to obtain reactant-1. 2-bromonaphthalene (2.07 g, 10 mmol) was dissolved in an excess of THF in another flask, the temperature was lowered to -78°C, 2.5 M n-BuLi (1 eq) was added dropwise, and the mixture was stirred for 3 hours. Then, dichlorodi(naphthalen-2-yl)silane (3.53 g, 10 mmol) was added to obtain reactant-2. To the generated reactant-2, the previously generated reactant-1 was added dropwise, and the mixture was slowly warmed to room temperature and stirred for 10 hours. After the reaction was completed, water was added and extracted to remove the solvent in the organic layer, and then silica column chromatography was used to obtain the target compound (3-bromophenyl)tri(naphthalen-2-yl)silane (2.09 g, yield 37%).

[0376] Mass: [(M+H) + ] : 565

[0377] <Step 2> Synthesis of BPH-12

[0378]

[0379] Under a nitrogen stream, (3-bromophenyl)di(naphthalen-2-yl)(phenyl)silane (5.65 g, 10 mmol), N-(4-(9H-carbazol-3-yl)phenyl)-N-phenylnaphthalen-1-amine (4.60 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), P(t-Bu)3 (0.47 ml, 2 mmol), NaO(t-Bu) (1.92 g, 20 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 3 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then column chromatography was used to obtain the target compound BPH-12 (4.15 g, yield 44%).

[0380] Mass: [(M+H) + ] : 945

[0381]

[0382] <Second Host Synthesis>

[0383] [Synthesis Example 13] Synthesis of BNH-01

[0384]

[0385] 9-(4,6-dichloro-1,3,5-triazin-2-yl)-9H-carbazole (3.15 g, 10 mmol), (3-(triphenylsilyl)phenyl)boronic acid (7.60 g, 20 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 1,4-dioxane (100 ml) / H2O (25 ml) and stirred at 100°C for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and compound BNH-01 (3.75 g, yield 41%) was obtained using column chromatography.

[0386] Mass: [(M+H) +] : 915

[0387]

[0388] [Synthesis Example 14] Synthesis of BNH-02

[0389]

[0390] 10-(4,6-dichloro-1,3,5-triazin-2-yl)-10H-phenoxazine (3.31 g, 10 mmol), (3-(triphenylsilyl)phenyl)boronic acid (7.60 g, 20 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), K2CO3 (2.76 g, 20 mmol) were added to 1,4-dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent of the filtered organic layer, compound BNH-02 (3.72 g, yield 40%) was obtained using column chromatography.

[0391] Mass: [(M+H) + ] : 931

[0392]

[0393] [Synthesis Example 15] Synthesis of BNH-03

[0394] <Step 1> Synthesis of (2'-nitro-[1,1'-biphenyl]-2-yl)triphenylsilane

[0395]

[0396] Triphenyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (4.62 g, 10 mmol), 1-bromo-2-nitrobenzene (2.02 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent in the filtered organic layer, the compound (2'-nitro-[1,1'-biphenyl]-2-yl)triphenylsilane (2.33 g, yield 51%) was obtained using column chromatography.

[0397] Mass: [(M+H) + ] : 457

[0398] <Step 2> Synthesis of 4-(triphenylsilyl)-9H-carbazole

[0399]

[0400] (2'-nitro-[1,1'-biphenyl]-2-yl)triphenylsilane (4.57 g, 10 mmol) and PPh3 (6.55 g, 25 mmol) were added to 50 ml of 1,2-dichlorobenzene and stirred at 150℃ for 18 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound 4-(triphenylsilyl)-9H-carbazole (1.83 g, yield 43%) was obtained using column chromatography.

[0401] Mass: [(M+H) + ] : 425

[0402] <Step 3> Synthesis of BNH-03

[0403]

[0404] Under a nitrogen stream, 4-(triphenylsilyl)-9H-carbazole (4.25 g, 10 mmol), 2-chloro-4-phenyl-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (5.26 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), P(t-Bu)3 (0.47 ml, 2 mmol), NaO(t-Bu) (1.92 g, 20 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 3 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then column chromatography was used to obtain the target compound BNH-03 (4.48 g, yield 49%).

[0405] Mass: 915

[0406]

[0407] [Synthesis Example 16] Synthesis of BNH-04

[0408]

[0409] 9-(2,6-dichloropyrimidin-4-yl)-9H-carbazole (3.14 g, 10 mmol), (3-(triphenylsilyl)phenyl)boronic acid (7.60 g, 20 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), and K2CO3 (2.76 g, 20 mmol) were added to 1,4-dioxane (100 ml) / H2O (25 ml) and stirred at 100°C for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. The solvent in the filtered organic layer was removed, and compound BNH-04 (4.02 g, yield 44%) was obtained using column chromatography.

[0410] Mass: [(M+H) + ] : 914

[0411]

[0412] [Synthesis Example 17] Synthesis of BNH-05

[0413]

[0414] (3-(9H-carbazol-9-yl)phenyl)boronic acid (2.87 g, 10 mmol), 2-chloro-4-phenyl-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (5.26 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), K2CO3 (2.76 g, 20 mmol) were added to 1,4-dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent of the filtered organic layer, compound BNH-05 (3.81 g, yield 52%) was obtained using column chromatography.

[0415] Mass: [(M+H) + ] : 732

[0416]

[0417] [Synthesis Example 18] Synthesis of BNH-06

[0418]

[0419] 9-(4-([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazin-2-yl)-9H-carbazole (4.32 g, 10 mmol), (3-(triphenylsilyl)phenyl)boronic acid (3.80 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtered. After removing the solvent of the filtered organic layer, compound BNH-06 (4.03 g, yield 55%) was obtained using column chromatography.

[0420] Mass: [(M+H) + ] : 732

[0421]

[0422] [Synthesis Example 19] Synthesis of BNH-07

[0423]

[0424] 9-(4-chloro-6-(phenanthren-9-yl)-1,3,5-triazin-2-yl)-9H-carbazole (4.56 g, 10 mmol), (3-(triphenylsilyl)phenyl)boronic acid (3.80 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), K2CO3 (2.76 g, 20 mmol) were added to 1,4-Dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent of the filtered organic layer, compound BNH-07 (3.93 g, yield 52%) was obtained using column chromatography.

[0425] Mass: [(M+H) + ] : 756

[0426]

[0427] [Synthesis Example 20] Synthesis of BNH-08

[0428] <Step 1> Synthesis of 2-chloro-4-(naphthalen-2-yl)-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine

[0429]

[0430] 2,4-dichloro-6-(naphthalen-2-yl)-1,3,5-triazine (5.52 g, 20 mmol), (3-(triphenylsilyl)phenyl)boronic acid (3.80 g, 10 mmol), PdCl2(PPh3)2 (0.14 g, 0.2 mmol), K2CO3 (2.76 g, 20 mmol) were added to 100 ml of toluene / 25 ml of H2O and stirred at 100℃ for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent in the filtered organic layer, the compound 2-chloro-4-(naphthalen-2-yl)-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (2.76 g, yield 48%) was obtained using column chromatography.

[0431] Mass: [(M+H) + ] : 576

[0432] <Step 2> Synthesis of BNH-08

[0433]

[0434] Under a nitrogen stream, 2-chloro-4-(naphthalen-2-yl)-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (5.76 g, 10 mmol), 5H-benzo[b]carbazole (2.17 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), P(t-Bu)3 (0.47 ml, 2 mmol), NaO(t-Bu) (1.92 g, 20 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 3 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then column chromatography was used to obtain the target compound BNH-08 (3.33 g, yield 44%).

[0435] [Mass]: 756

[0436]

[0437] [Synthesis Example 21] Synthesis of BNH-09

[0438]

[0439] Under a nitrogen stream, 2-chloro-4-phenyl-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (5.26 g, 10 mmol), 6H-dibenzo[b,h]carbazole (2.67 g, 10 mmol), Pd(OAc)2 (0.22 g, 1 mmol), P(t-Bu)3 (0.47 ml, 2 mmol), NaO(t-Bu) (1.92 g, 20 mmol) and 100 ml of toluene were mixed and stirred at 110°C for 3 hours. After the reaction was completed, toluene was concentrated, the solid salt was filtered, and then column chromatography was used to obtain the target compound BNH-09 (2.95 g, yield 39%).

[0440] [Mass]: 756

[0441]

[0442] [Synthesis Example 22] Synthesis of BNH-10

[0443] <Step 1> Synthesis of (3-bromophenyl)di(naphthalen-2-yl)(phenyl)silane

[0444]

[0445] 1,3-dibromobenzene (2.35 g, 10 mmol) was dissolved in an excess of THF, the temperature was lowered to -78°C, and 2.5 M n-BuLi (1 eq) was added dropwise to obtain reactant-1. In another flask, bromobenzene (1.57 g, 10 mmol) was dissolved in an excess of THF, the temperature was lowered to -78°C, 2.5 M n-BuLi (1 eq) was added dropwise, and the mixture was stirred for 3 hours. Then, dichlorodi(naphthalen-2-yl)silane (3.53 g, 10 mmol) was added to obtain reactant-2. To the generated reactant-2, the previously generated reactant-1 was added dropwise, and the mixture was slowly warmed to room temperature and stirred for 10 hours. After the reaction was completed, water was added and extracted to remove the solvent in the organic layer, and then silica column chromatography was used to obtain the target compound (3-bromophenyl)di(naphthalen-2-yl)(phenyl)silane (1.80 g, yield 35%).

[0446] Mass: [(M+H) + ] : 515

[0447] <Step 2> Synthesis of di(naphthalen-2-yl)(phenyl)(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane

[0448]

[0449] (3-bromophenyl)di(naphthalen-2-yl)(phenyl)silane (5.15 g, 10 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (3.80 g, 15 mmol), Pd(dppf)Cl2 (0.36 g, 0.5 mmol), and KOAc (1.96 g, 20 mmol) were added to 100 ml of 1,4-Dioxane and stirred at 100°C for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound di(naphthalen-2-yl)(phenyl)(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (2.86 g, yield 51%) was obtained using column chromatography.

[0450] Mass: [(M+H) + ] : 562

[0451] <Step 3> Synthesis of 2-chloro-4-(3-(di(naphthalen-2-yl)(phenyl)silyl)phenyl)-6-(naphthalen-1-yl)-1,3,5-triazine

[0452]

[0453] Di(naphthalen-2-yl)(phenyl)(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (5.52 g, 10 mmol), 2,4-dichloro-6-(naphthalen-1-yl)-1,3,5-triazine (5.52 g, 20 mmol), PdCl2(PPh3)2 (0.14 g, 0.2 mmol), K2CO3 (2.76 g, 20 mmol) were added to 100 ml of toluene / 25 ml of H2O and stirred at 100°C for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgSO4 was added, and filtered. After removing the solvent from the filtered organic layer, the compound 2-chloro-4-(3-(di(naphthalen-2-yl)(phenyl)silyl)phenyl)-6-(naphthalen-1-yl)-1,3,5-triazine (2.09 g, yield 31%) was obtained using column chromatography.

[0454] Mass: [(M+H) + ] : 676

[0455] <Step 4> Synthesis of BNH-10

[0456]

[0457] 2-chloro-4-(3-(di(naphthalen-2-yl)(phenyl)silyl)phenyl)-6-(naphthalen-1-yl)-1,3,5-triazine (6.76 g, 10 mmol), (4-(9H-carbazol-9-yl)naphthalen-1-yl)boronic acid (3.37 g, 10 mmol), Pd(PPh3)4 (0.34 g, 0.3 mmol), K2CO3 (2.76 g, 20 mmol) were added to 1,4-dioxane 100 ml / H2O 25 ml and stirred at 100℃ for 8 hours. After completion of the reaction, extraction was performed with methylene chloride, MgSO4 was added, and filtration was performed. After removing the solvent of the filtered organic layer, compound BNH-10 (5.03 g, yield 54%) was obtained using column chromatography.

[0458] Mass: [(M+H) + ] : 933

[0459]

[0460] <First dopant synthesis>

[0461] [Synthesis Example 23: Synthesis of PTB-05]

[0462] <Step 1> Synthesis of 3-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)aniline

[0463]

[0464] Under a nitrogen stream, 2-bromo-9-(pyridin-2-yl)-9H-carbazole (32.3 g, 100.0 mmol), 3-aminophenol (13.1 g, 120.0 mmol), CuI (1.9 g, 10.0 mmol), L-proline (2.3 g, 20.0 mmol), and Cs2CO3 (65.2 g, 200.0 mmol) were added to 200 mL of DMSO and stirred at 120°C for 72 h. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and ethyl acetate was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain compound 3-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)aniline (25.5 g, 72.6 mmol, yield 73%).

[0465] Mass [(M+H) + ] : 352

[0466] <Step 2> N 1 -phenyl-N 2 -Synthesis of (3-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)phenyl)benzene-1,2-diamine

[0467]

[0468] Under a nitrogen atmosphere, 2-bromo-N-phenylaniline (16.4 g, 66.1 mmol) and 3-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)aniline (25.5 g, 72.6 mmol), Pd(OAc)2 (815 mg, 3.6 mmol), CyJohnPhos (2.5 g, 7.3 mmol), t-BuONa (10.5 g, 108.9 mmol) were added to 360 mL of toluene and heated under reflux for 18 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and ethyl acetate was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography to obtain compound N. 1 -phenyl-N 2 -(3-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)phenyl)benzene-1,2-diamine (29.5 g, 56.9 mmol, yield 78%) was obtained.

[0469] Mass [(M+H) + ] : 519

[0470] <Step 3> Synthesis of PTB-05

[0471]

[0472] N under nitrogen atmosphere 1 -phenyl-N 2-(3-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)phenyl)benzene-1,2-diamine (29.5 g, 56.9 mmol) and NH4PF6 (10.2 g, 62.6 mmol) were added to 115 mL of triethyl orthoformate and stirred at 120°C for 12 hours. After completion of the reaction, ethyl acetate was added and stirred at room temperature, and the precipitated solid was filtered to obtain 3-phenyl-1-(3-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)phenyl)-1H-benzo[d]imidazol-3-ium hexafluorophosphate (22.3 g, 33.0 mmol). Subsequently, 3-phenyl-1-(3-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)phenyl)-1H-benzo[d]imidazol-3-ium hexafluorophosphate (22.3 g, 33.0 mmol), Pt(COD)Cl2 (11.2 g, 30.0 mmol), and NaOAc (2.8 g, 34.7 mmol) were added to 66 mL of THF under a nitrogen flow and heated under reflux for 68 h. After completion of the reaction, the mixture was concentrated and purified by column chromatography filled with silica gel to obtain compound PTB-05 (7.9 g, 10.9 mmol, yield 19%).

[0473] Mass [(M+H) + ] : 722

[0474]

[0475] [Synthesis Example 24: Synthesis of PTB-06]

[0476] <Step 1> Synthesis of [Pt2(μ-Cl)2(ppb)2]

[0477]

[0478] N under nitrogen atmosphere 1 ,N 2-Diphenylbenzene-1,2-diamine (26.0 g, 100.0 mmol) and NH4BF4 (10.5 g, 100.0 mmol) were added to 300 mL of triethyl orthoformate and stirred at 120°C for 18 hours. After completion of the reaction, the mixture was stirred at room temperature, and the precipitated solid was filtered and washed with triethyl orthoformate and petroleum ether to obtain 1,3-diphenyl-1H-benzo[d]imidazol-3-ium tetrafluoroborate (29.9 g, 83.6 mmol). Then, 1,3-diphenyl-1H-benzo[d]imidazol-3-ium tetrafluoroborate (29.9 g, 83.6 mmol) was added to 3.1 L of DCM under a nitrogen atmosphere, and Ag2O (9.7 g, 41.8 mmol) was added, followed by stirring at room temperature for 3 h. Then, [{Pt(ㅅ-Cl)(η 3 -2-Me-C3H4)}2] (22.9 g, 40.1 mmol) was added and stirred at room temperature for 3 hours. The reaction mixture was filtered through celite, the solution was concentrated, 850 mL of 2-methoxyethanol was added, and the mixture was heated and stirred under reflux for 3 hours. After the reaction was completed, the mixture was stirred at room temperature, the precipitated solid was filtered, and washed with diethyl ether to obtain compound [Pt2(μ-Cl)2(ppb)2] (21.6 g, 21.6 mmol, yield 43%).

[0479] Mass [(M+H) + ] : 999

[0480] <Step 2> Synthesis of PTB-06

[0481]

[0482] [Pt2(μ-Cl)2(ppb)2] (21.6 g, 21.6 mmol) and 9-(pyridin-2-yl)-9H-carbazole (13.2 g, 54.0 mmol) were added to 45 mL of 2-methoxyethanol and heated and refluxed for 24 hours. After completion of the reaction, the mixture was stirred at room temperature, filtered, washed with diethyl ether, and purified by column chromatography filled with silica gel to obtain compound PTB-06 (xx g, xx mmol, yield xx%).

[0483] Mass [(M+H) + ] : 708

[0484]

[0485] [Synthesis Example 25: Synthesis of PTB-07]

[0486] <Step 1> Synthesis of 3-(tert-butyl)-5-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)aniline

[0487]

[0488] Under a nitrogen stream, 2-bromo-9-(pyridin-2-yl)-9H-carbazole (32.3 g, 100.0 mmol), 3-amino-5-(tert-butyl)phenol (19.8 g, 120.0 mmol), CuI (1.9 g, 10.0 mmol), L-proline (2.3 g, 20.0 mmol), and Cs2CO3 (65.2 g, 200.0 mmol) were added to 200 mL of DMSO and stirred at 120°C for 72 h. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and ethyl acetate was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain compound 3-(tert-butyl)-5-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)aniline (30.3 g, 74.3 mmol, yield 73%).

[0489] Mass [(M+H) + ] : 408

[0490] <Step 2> N 1 -(3-(tert-butyl)-5-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)phenyl)-N 2 -Synthesis of phenylbenzene-1,2-diamine

[0491]

[0492] Under a nitrogen atmosphere, 2-bromo-N-phenylaniline (16.8 g, 67.6 mmol) and 3-(tert-butyl)-5-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)aniline (30.3 g, 74.3 mmol), Pd(OAc)2 (834 mg, 3.7 mmol), CyJohnPhos (2.6 g, 7.4 mmol), t-BuONa (10.7 g, 111.5 mmol) were added to 370 mL of toluene and heated under reflux for 18 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and ethyl acetate was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography to obtain compound N. 1 -(3-(tert-butyl)-5-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)phenyl)-N 2 -Phenylbenzene-1,2-diamine (32.6 g, 56.8 mmol, yield 76%) was obtained.

[0493] Mass [(M+H) + ] : 575

[0494] <Step 3> Synthesis of PTB-07

[0495]

[0496] N under nitrogen atmosphere 1 -(3-(tert-butyl)-5-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)phenyl)-N 2-Phenylbenzene-1,2-diamine (32.6 g, 56.8 mmol) and NH4PF6 (10.2 g, 62.4 mmol) were added to 110 mL of triethyl orthoformate and stirred at 120°C for 12 hours. After completion of the reaction, ethyl acetate was added and stirred at room temperature, and the precipitated solid was filtered to obtain 1-(3-(tert-butyl)-5-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)phenyl)-3-phenyl-1H-benzo[d]imidazol-3-ium hexafluorophosphate (25.0 g, 34.2 mmol). Then, under a nitrogen stream, 1-(3-(tert-butyl)-5-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)phenyl)-3-phenyl-1H-benzo[d]imidazol-3-ium hexafluorophosphate (25.0 g, 34.2 mmol), Pt(COD)Cl2 (11.6 g, 31.1 mmol), and NaOAc (2.9 g, 35.9 mmol) were added to 70 mL of THF and heated under reflux for 65 h. After completion of the reaction, the mixture was concentrated and purified by column chromatography filled with silica gel to obtain compound PTB-07 (9.4 g, 12.1 mmol, yield 21%).

[0497] Mass [(M+H) + ] : 778

[0498]

[0499] [Synthesis Example 26: Synthesis of PTB-08]

[0500] <Step 1> Synthesis of 6-((9-phenyl-9H-carbazol-2-yl)oxy)pyridin-2-amine

[0501]

[0502] Under a nitrogen stream, 2-bromo-9-phenyl-9H-carbazole (32.3 g, 100.0 mmol), 6-aminopyridin-2-ol (13.2 g, 120.0 mmol), CuI (1.9 g, 10.0 mmol), L-proline (2.3 g, 20.0 mmol), and Cs2CO3 (65.2 g, 200.0 mmol) were added to 200 mL of DMSO and stirred at 120°C for 72 h. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and ethyl acetate was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain compound 6-((9-phenyl-9H-carbazol-2-yl)oxy)pyridin-2-amine (22.0 g, 62.6 mmol, yield 63%).

[0503] Mass [(M+H) + ] : 352

[0504] <Step 2> N 1 -phenyl-N 2 -Synthesis of (6-((9-phenyl-9H-carbazol-2-yl)oxy)pyridin-2-yl)benzene-1,2-diamine

[0505]

[0506] Under a nitrogen atmosphere, 2-bromo-N-phenylaniline (14.1 g, 57.0 mmol) and 6-((9-phenyl-9H-carbazol-2-yl)oxy)pyridin-2-amine (22.0 g, 62.6 mmol), Pd(OAc)2 (703 mg, 3.1 mmol), CyJohnPhos (2.2 g, 6.3 mmol), t-BuONa (9.0 g, 93.9 mmol) were added to 315 mL of toluene and heated under reflux for 18 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and ethyl acetate was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography to obtain compound N. 1 -phenyl-N 2 -(6-((9-phenyl-9H-carbazol-2-yl)oxy)pyridin-2-yl)benzene-1,2-diamine (25.8 g, 49.7 mmol, yield 79%) was obtained.

[0507] Mass [(M+H) + ] : 519

[0508] <Step 3> Synthesis of PTB-08

[0509]

[0510] N under nitrogen atmosphere 1 -phenyl-N 2-(6-((9-phenyl-9H-carbazol-2-yl)oxy)pyridin-2-yl)benzene-1,2-diamine (25.8 g, 49.7 mmol) and NH4PF6 (8.9 g, 54.7 mmol 1.1 eq) were added to 100 mL of triethyl orthoformate and stirred at 120°C for 12 hours. After completion of the reaction, ethyl acetate was added and stirred at room temperature, and the precipitated solid was filtered to obtain 3-phenyl-1-(6-((9-phenyl-9H-carbazol-2-yl)oxy)pyridin-2-yl)-1H-benzo[d]imidazol-3-ium hexafluorophosphate (22.1 g, 32.7 mmol). Subsequently, 3-phenyl-1-(6-((9-phenyl-9H-carbazol-2-yl)oxy)pyridin-2-yl)-1H-benzo[d]imidazol-3-ium hexafluorophosphate (22.1 g, 32.7 mmol), Pt(COD)Cl2 (11.1 g, 29.8 mmol), and NaOAc (2.8 g, 34.3 mmol) were added to 65 mL of THF under a nitrogen flow and heated under reflux for 70 h. After completion of the reaction, the mixture was concentrated and purified by column chromatography filled with silica gel to obtain compound PTB-08 (6.2 g, 8.7 mmol, yield 17%).

[0511] Mass [(M+H) + ] : 722

[0512]

[0513] <Second dopant synthesis>

[0514] [Synthesis Example 27] Synthesis of BD-05

[0515] <Step 1> N 1 ,N 3 -bis(3-(tert-butyl)phenyl)-2-chloro-N 1 ,N 3-Synthesis of diphenylbenzene-1,3-diamine

[0516]

[0517] Under a nitrogen atmosphere, 1-Bromo-2,3-dichlorobenzene (22.6 g, 100 mmol) and 3-(tert-butyl)-N-phenylaniline (49.6 g, 220.0 mmol), (AMPHOS)2PdCl2 (779 mg, 1.1 mmol), t-BuONa (24.0 g, 250.0 mmol) were added to 225 mL of o-xylene and stirred at 80°C for 2 hours and then at 120°C for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and ethyl acetate was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound N. 1 ,N 3 -bis(3-(tert-butyl)phenyl)-2-chloro-N 1 ,N 3 -Diphenylbenzene-1,3-diamine (36.6 g, 65.4 mmol, yield 65%) was obtained.

[0518] Mass [(M+H) + ] : 559

[0519] <Step 2> Synthesis of BD-05

[0520]

[0521] N under nitrogen atmosphere 1 ,N 3 -bis(3-(tert-butyl)phenyl)-2-chloro-N 1 ,N 3-Diphenylbenzene-1,3-diamine (36.6 g, 65.4 mmol) was added to 220 mL of tert-butylbenzene, and tert-butyllithium (46.2 mL, 78.5 mmol, 1.70 M sol. in pentane) was slowly added at -30°C, and the mixture was stirred at 60°C for 3 hours. Next, the mixture was concentrated to remove pentane, cooled to -30°C, and BBr3 (7.6 mL, 78.5 mmol) was slowly added. The reaction mixture was stirred at room temperature for 30 minutes, cooled again to 0°C, and N,N-Diisopropylethylamine (22.8 mL, 130.8 mmol) was added. The mixture was stirred at 120°C for 2 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and ethyl acetate was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound 3,11-di-tert-butyl-5,9-diphenyl-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene (9.9 g, 18.6 mmol, yield 28%).

[0522] Mass [(M+H) + ] : 533

[0523]

[0524] [Synthesis Example 28] Synthesis of BD-06

[0525] <Step 1> Synthesis of 2,3-dichloro-N-(m-tolyl)-N-(p-tolyl)aniline

[0526]

[0527] Under a nitrogen stream, 1-Bromo-2,3-dichlorobenzene (22.6 g, 100 mmol), 3-methyl-N-(p-tolyl)aniline (19.7 g, 100.0 mmol), (AMPHOS)2PdCl2 (354 mg, 0.5 mmol), and t-BuONa (14.4 g, 150.0 mmol) were added to 225 mL of o-xylene and stirred at 90°C for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and ethyl acetate was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 2,3-dichloro-N-(m-tolyl)-N-(p-tolyl)aniline (26.6 g, 77.6 mmol, yield 78%).

[0528] Mass [(M+H) + ] : 342

[0529] <Step 2> N 1 -(4-(9H-carbazol-9-yl)phenyl)-2-chloro-N 1 -phenyl-N 3 -(m-tolyl)-N 3 Synthesis of -(p-tolyl)benzene-1,3-diamine

[0530]

[0531] Under a nitrogen atmosphere, 2,3-dichloro-N-(m-tolyl)-N-(p-tolyl)aniline (26.6 g, 77.6 mmol) and 4-(9H-carbazol-9-yl)-N-phenylaniline (26.0 g, 77.6 mmol), (AMPHOS)2PdCl2 (604 mg, 0.9 mmol), t-BuONa (11.2 g, 116.4 mmol) were added to 175 mL of o-xylene and stirred at 120°C for 2 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and ethyl acetate was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound N. 1 -(4-(9H-carbazol-9-yl)phenyl)-2-chloro-N 1 -phenyl-N 3 -(m-tolyl)-N 3 -(p-tolyl)benzene-1,3-diamine (40.4 g, 63.2 mmol, yield 81%) was obtained.

[0532] Mass [(M+H) + ] : 640

[0533] <Step 3> Synthesis of BD-06

[0534]

[0535] N under nitrogen atmosphere 1 -(4-(9H-carbazol-9-yl)phenyl)-2-chloro-N 1 -phenyl-N 3 -(m-tolyl)-N 3-(p-tolyl)benzene-1,3-diamine (40.4 g, 63.2 mmol) was added to 420 mL of tert-butylbenzene, and tert-butyllithium (44.6 mL, 75.8 mmol, 1.70 M sol. in pentane) was slowly added at -30°C, and the mixture was stirred at 60°C for 3 h. Next, the mixture was concentrated to remove pentane, cooled to -30°C, and BBr3 (7.3 mL, 75.8 mmol) was slowly added. The reaction mixture was stirred at room temperature for 30 min, cooled again to 0°C, and N,N-Diisopropylethylamine (22.0 mL, 126.3 mmol) was added. The mixture was stirred at 120°C for 2 h. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and ethyl acetate was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound 9-(4-(9H-carbazol-9-yl)phenyl)-3-methyl-5-(p-tolyl)-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene (11.4 g, 18.6 mmol, yield 29%).

[0536] Mass [(M+H) + ] : 614

[0537]

[0538] [Synthesis Example 29] Synthesis of BD-07

[0539] <Step 1> N 1 ,N 3 -bis(4-(tert-butyl)phenyl)-2-chloro-N 1 ,N 3 -Synthesis of diphenylbenzene-1,3-diamine

[0540]

[0541] Under a nitrogen atmosphere, 1-Bromo-2,3-dichlorobenzene (22.6 g, 100 mmol) and 4-(tert-butyl)-N-phenylaniline (49.6 g, 220.0 mmol), (AMPHOS)2PdCl2 (779 mg, 1.1 mmol), t-BuONa (24.0 g, 250.0 mmol) were added to 225 mL of o-xylene and stirred at 80°C for 2 hours and then at 120°C for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and ethyl acetate was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound N. 1 ,N 3 -bis(4-(tert-butyl)phenyl)-2-chloro-N 1 ,N 3 -diphenylbenzene-1,3-diamine (42.1 g, 75.3 mmol, yield 75%) was obtained.

[0542] Mass [(M+H) + ] : 559

[0543] <Step 2> Synthesis of BD-07

[0544]

[0545] N under nitrogen atmosphere 1 ,N 3 -bis(4-(tert-butyl)phenyl)-2-chloro-N 1 ,N 3-Diphenylbenzene-1,3-diamine (42.1 g, 75.3 mmol) was added to 250 mL of tert-butylbenzene, and tert-butyllithium (53.2 mL, 90.4 mmol, 1.70 M sol. in pentane) was slowly added at -30°C, and the mixture was stirred at 60°C for 3 hours. Next, the mixture was concentrated to remove pentane, cooled to -30°C, and BBr3 (8.7 mL, 90.4 mmol) was slowly added. The reaction mixture was stirred at room temperature for 30 minutes, cooled again to 0°C, and N,N-Diisopropylethylamine (26.2 mL, 150.6 mmol) was added. The mixture was stirred at 120°C for 2 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and ethyl acetate was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain the compound 5,9-bis(4-(tert-butyl)phenyl)-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene (10.5 g, 19.7 mmol, yield 26%).

[0546] Mass [(M+H) + ] : 533

[0547]

[0548] [Synthesis Example 30] Synthesis of BD-08

[0549] <Step 1> N 1 ,N 1 ,N 3 ,N 3 -Synthesis of tetrakis(4-(tert-butyl)phenyl)-2-chlorobenzene-1,3-diamine

[0550]

[0551] Under a nitrogen atmosphere, 1-Bromo-2,3-dichlorobenzene (22.6 g, 100 mmol), bis(4-(tert-butyl)phenyl)amine (61.9 g, 220.0 mmol), (AMPHOS)2PdCl2 (779 mg, 1.1 mmol), t-BuONa (24.0 g, 250.0 mmol) were added to 225 mL of o-xylene and stirred at 80°C for 2 hours and then at 120°C for 3 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and ethyl acetate was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography. After concentration, the solid obtained by stirring in a small amount of toluene and hexane was filtered to obtain compound N. 1 ,N 1 ,N 3 ,N 3 -tetrakis(4-(tert-butyl)phenyl)-2-chlorobenzene-1,3-diamine (49.4 g, 73.6 mmol, yield 74%) was obtained.

[0552] Mass [(M+H) + ] : 671

[0553] <Step 2> Synthesis of BD-08

[0554]

[0555] N under nitrogen atmosphere 1 ,N 1 ,N 3 ,N 3-Tetrakis(4-(tert-butyl)phenyl)-2-chlorobenzene-1,3-diamine (49.4 g, 73.6 mmol) was added to 245 mL of tert-butylbenzene, and tert-butyllithium (52.0 mL, 88.3 mmol, 1.70 M sol. in pentane) was slowly added at -30°C, and the mixture was stirred at 60°C for 3 hours. Next, the mixture was concentrated to remove pentane, cooled to -30°C, and BBr3 (8.5 mL, 88.3 mmol) was slowly added. The reaction mixture was stirred at room temperature for 30 minutes, cooled to 0°C, and N,N-Diisopropylethylamine (25.6 mL, 147.2 mmol) was added. The mixture was then stirred at 120°C for 2 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and ethyl acetate was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. After concentration, the mixture was stirred in a small amount of toluene and hexane, and the obtained solid was filtered to obtain the compound 2,12-di-tert-butyl-5,9-bis(4-(tert-butyl)phenyl)-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene (10.3 g, 16.0 mmol, yield 22%).

[0556] Mass [(M+H) + ] : 645

[0557]

[0558] <Synthesis of electron transport auxiliary layer materials>

[0559] [Synthesis Example 31] Synthesis of compound ETA-01

[0560]

[0561] <Step 1> Synthesis of ETA-1-i

[0562] 2-chloro-4,6-diphenyl-1,3,5-triazine 25g (93.4mmol, 1eq) and (2-(8-chlorodibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 36.8g (112.1mmol, 1.2eq), Pd(PPh3)4 4.3g (3.7mmol, 0.04eq), K2CO3 25.8g (186.8mmol, 2eq) were added to 375ml of THF and 125ml of H2O and heated and stirred under reflux for 4 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water and transferred to a separatory funnel. MC was added, and the organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. Compound ETA-1-i, 2-(8-chlorodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine (34.4 g, yield 85%) was obtained.

[0563] Mass: [(M+H) + ] : 434

[0564] NMR( 1 H): σ= 8.46(4H, m), 8.08(1H, d), 7.88(1H, d), 7.54-7.43(9H, m), 7.20(1H, d)

[0565] <Step 2> Synthesis of ETA-1

[0566] 34.4 g (79.4 mmol, 1 eq) of 2-(8-chlorodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine, 40.4 g (87.3 mmol, 1.1 eq) of triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 0.5 g (2.4 mmol, 0.03 eq) of Pd(OAc)2, 3.8 g (7.9 mmol, 0.1 eq) of Xphos, and 24.1 g (174.6 mmol, 2 eq) of K2CO3 were added to 500 ml of toluene, 120 ml of EtOH, and 120 ml of H2O, and heated and stirred under reflux for 10 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. After dissolving in toluene and adding hexane dropwise, the resulting white crystals were filtered to obtain compound ETA-1, 72,4-diphenyl-6-(8-(4-(triphenylsilyl)phenyl)dibenzo[b,d]furan-4-yl)-1,3,5-triazine (44.3 g, yield 76%).

[0567] Mass: [(M+H) + ] : 734

[0568]

[0569] [Synthesis Example 32] Synthesis of compound ETA-2

[0570]

[0571] 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine, 25 g (57.4 mmol, 1 eq), 9-chlorospiro[benzo[c]fluorene-7,9'-xanthene], 28.7 g (68.9 mmol, 1.2 eq), Pd(OAc)2, 0.4 g (1.7 mmol, 0.03 eq), Xphos, 2.7 g (5.7 mmol, 0.1 eq), and K2CO3, 15.9 g (114.9 mmol, 2 eq) were added to toluene ml, EtOH ml, and H2O ml, and heated and stirred under reflux for 10 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. After dissolving in toluene and adding hexane dropwise, the resulting white crystals were filtered to obtain compound ETA-2, 2,4-diphenyl-6-(3-(spiro[benzo[c]fluorene-7,9'-xanthen]-9-yl)phenyl)-1,3,5-triazine (31.7 g, yield 80%).

[0572] Mass: [(M+H) + ] : 690

[0573]

[0574] [Synthesis Example 33] Synthesis of compound ETA-3

[0575]

[0576] 25 g (61.3 mmol, 1 eq) of 2-chloro-4-(naphtho[2,1-b]benzofuran-10-yl)-6-phenyl-1,3,5-triazine, 34.0 g (73.6 mmol, 1.2 eq) of triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 2.8 g (2.5 mmol, 0.04 eq) of Pd(PPh3)4, and 16.9 g (122.6 mmol, 2 eq) of K2CO3 were added to 375 ml of toluene, 100 ml of EtOH, and 100 ml of H2O, and the mixture was heated and stirred under reflux for 8 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography. After dissolving in toluene and adding hexane dropwise, the resulting white crystals were filtered to obtain compound ETA-3, 2-(naphtho[2,1-b]benzofuran-10-yl)-4-phenyl-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (33.0 g, yield 76%).

[0577] Mass: [(M+H)+]: 708

[0578]

[0579] [Synthesis Example 34] Synthesis of compound ETA-4

[0580]

[0581] 25 g (46.1 mmol, 1 eq) of 4-([1,1'-biphenyl]-4-yl)-6-(3,5-dibromophenyl)-2-phenylpyrimidine, 17.7 g (106.0 mmol, 2.3 eq) of 9H-carbazole, 2.1 g (2.3 mmol, 0.05 eq) of Pd2(dba)3, 3.3 g (6.9 mmol, 0.15 eq) of Xphos, and 18.1 g (184.4 mmol, 4.0 eq) of NaOtBu were added to 500 ml of toluene and heated under reflux for 12 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the precipitated solid was filtered and dried. The obtained solid was dissolved in a sufficient amount of MCB, filtered through silica gel, and purified by column chromatography to obtain compound ETA-4, 9,9'-(5-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis(9H-carbazole) (23.7 g, yield 72%).

[0582] Mass: [(M+H)+]: 715

[0583]

[0584] [Synthesis Example 35] Synthesis of compound ETA-5

[0585]

[0586] <Step 1> Synthesis of ETA-5-i

[0587] 25g (73.2mmol, 1eq) of 2'-bromo-6'-chloro-1,1':4',1''-terphenyl and 38.2g (87.8mmol, 1.2eq) of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine, 3.4g (2.9mmol, 0.04eq) of Pd(PPh3)4, and 20.2g (146.3mmol, 2eq) of K2CO3 were added to 375ml of THF and 125ml of H2O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain compound ETA-5-i, 2-(3'-chloro-5'-phenyl-[1,1':2',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (35.6 g, yield 85%).

[0588] Mass: [(M+H)+]: 572

[0589] NMR(1H): σ= 8.36(4H, m), 8.26(1H, s), 8.01(1H, s), 7.94(1H, s), 7.75-7.73(3H, m), 7.61(1H, d), 7.51-7.41(14H, m)

[0590] <Step 2> Synthesis of ETA-5

[0591] 35.6 g (62.2 mmol, 1 eq) of 2-(3'-chloro-5'-phenyl-[1,1':2',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine and 31.6 g (68.4 mmol, 1.1 eq) of triphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 0.4 g (1.9 mmol, 0.03 eq) of Pd(OAc)2, 3.0 g (6.2 mmol, 0.1 eq) of Xphos, and 18.9 g (136.8 mmol, 2 eq) of K2CO3 were added to 530 ml of toluene, 140 ml of EtOH, and 140 ml of H2O, and heated and stirred under reflux for 10 hours. After the reaction was completed, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, adsorbed on silica gel, and purified by column chromatography. After dissolving in toluene and adding hexane dropwise, the resulting white crystals were filtered to obtain compound ETA-5, 2,4-diphenyl-6-(5'-phenyl-3'-(4-(triphenylsilyl)phenyl)-[1,1':2',1''-terphenyl]-3-yl)-1,3,5-triazine (37.4 g, yield 69%).

[0592] Mass: [(M+H)+]: 872

[0593]

[0594] [Synthesis Example 36] Synthesis of compound ETA-6

[0595]

[0596] 25 g (55.8 mmol, 1 eq) of 2-chloro-4,6-bis(dibenzo[b,d]furan-4-yl)-1,3,5-triazine, 31.0 g (67.0 mmol, 1.2 eq) of triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 2.6 g (2.2 mmol, 0.04 eq) of Pd(PPh3)4, and 15.4 g (111.6 mmol, 2 eq) of K2CO3 were added to 375 ml of THF and 125 ml of H2O, and the mixture was heated and stirred under reflux for 4 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the precipitated solid was filtered and dried. The obtained solid was dissolved in a sufficient amount of MCB, filtered through silica gel, and purified by column chromatography to obtain compound ETA-6, 2,4-bis(dibenzo[b,d]furan-4-yl)-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (34.2 g, yield 82%).

[0597] Mass: [(M+H)+]: 748

[0598]

[0599] [Synthesis Example 37] Synthesis of compound ETA-7

[0600]

[0601] 25 g (40.6 mmol, 1 eq) of 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-(4-(triphenylsilyl)phenyl)-1,3,5-triazine, 22.5 g (48.7 mmol, 1.2 eq) of triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane, 1.9 g (1.6 mmol, 0.04 eq) of Pd(PPh3)4, and 11.2 g (81.1 mmol, 2 eq) of K2CO3 were added to 375 ml of THF and 125 ml of H2O, and the mixture was heated and stirred under reflux for 5 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, transferred to a separatory funnel, and MC was added. The organic layer was separated and extracted. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain compound ETA-7, 2-(dibenzo[b,d]furan-2-yl)-4-(3-(triphenylsilyl)phenyl)-6-(4-(triphenylsilyl)phenyl)-1,3,5-triazine (27.9 g, yield 75%).

[0602] Mass: [(M+H)+]: 916

[0603]

[0604] [Synthesis Example 38] Synthesis of compound ETA-8

[0605]

[0606] 25 g (59.5 mmol, 1 eq) of 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)-6-phenyl-1,3,5-triazine, 32.6 g (71.4 mmol, 1.2 eq) of 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-2'-yl)-1,3,2-dioxaborolane, 0.4 g (1.8 mmol, 0.03 eq) of Pd(OAc)2, 2.8 g (6.0 mmol, 0.1 eq) of Xphos, and 16.5 g (119.1 mmol, 2 eq) of K2CO3 were added to 375 ml of THF and 125 ml of H2O, and heated and stirred under reflux for 6 hours. After completion of the reaction, the precipitated solid was filtered and dried after being deactivated with a sufficient amount of water. The obtained solid was dissolved in a sufficient amount of MCB, filtered through silica gel, and purified by column chromatography to obtain compound ETA-8, 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(2-(spiro[fluorene-9,9'-xanthen]-2'-yl)phenyl)-1,3,5-triazine (32.0 g, yield 75%).

[0607] Mass: [(M+H)+]: 716

[0608]

[0609] [Synthesis Example 39] Synthesis of compound ETA-9

[0610]

[0611] 25 g (44.1 mmol, 1 eq) of 2-(3,5-dibromophenyl)-4,6-di(naphthalen-2-yl)-1,3,5-triazine, 16.9 g (101.4 mmol, 2.3 eq) of 9H-carbazole, 2.0 g (2.2 mmol, 0.05 eq) of Pd2(dba)3, 3.2 g (6.6 mmol, 0.15 eq) of Xphos, and 17.3 g (176.3 mmol, 4.0 eq) of NaOtBu were added to 500 ml of toluene and heated and stirred under reflux for 12 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the precipitated solid was filtered and dried. The obtained solid was dissolved in a sufficient amount of MCB, filtered through silica gel, and purified by column chromatography to obtain compound ETA-9, 9,9'-(5-(4,6-di(naphthalen-2-yl)-1,3,5-triazin-2-yl)-1,3-phenylene)bis(9H-carbazole) (23.2 g, yield 68%).

[0612] Mass: [(M+H)+]: 740

[0613]

[0614] [Synthesis Example 40] Synthesis of compound ETA-10

[0615]

[0616] 25 g (56.3 mmol, 1 eq) of 2-(2-chlorophenyl)-4,6-di(naphthalen-2-yl)-1,3,5-triazine, 31.0 g (67.6 mmol, 1.2 eq) of 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-2'-yl)-1,3,2-dioxaborolane, 0.4 g (1.7 mmol, 0.03 eq) of Pd(OAc)2, 2.7 g (5.6 mmol, 0.1 eq) of Xphos, and 15.6 g (112.6 mmol, 2 eq) of K2CO3 were added to 375 ml of THF and 125 ml of H2O, and heated and stirred under reflux for 6 hours. After completion of the reaction, the precipitated solid was filtered and dried after being deactivated with a sufficient amount of water. The obtained solid was dissolved in a sufficient amount of MCB, filtered through silica gel, and purified by column chromatography to obtain compound ETA-10, 2,4-di(naphthalen-2-yl)-6-(2-(spiro[fluorene-9,9'-xanthen]-2'-yl)phenyl)-1,3,5-triazine (27.5 g, yield 66%).

[0617] Mass: [(M+H)+]: 740

[0618]

[0619] [Synthesis Example 41] Synthesis of compound ETA-11

[0620]

[0621] 2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 20 g (58.2 mmol, 1 eq), 2-(9,9'-spirobi[xanthen]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 33.1 g (69.8 mmol, 1.2 eq), Pd(OAc)2 0.4 g (1.7 mmol, 0.03 eq), Xphos 2.8 g (5.8 mmol, 0.1 eq), and K2CO3 16.1 g (116.3 mmol, 2 eq) were added to 400 ml of THF and 150 ml of H2O, and the mixture was heated and stirred under reflux for 6 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the precipitated solid was filtered and dried. The obtained solid was dissolved in a sufficient amount of MCB, filtered through silica gel, and purified by column chromatography to obtain compound ETA-11, 2-(2-(9,9'-spirobi[xanthen]-2-yl)phenyl)-4,6-diphenyl-1,3,5-triazine (29.0 g, yield 76%).

[0622] Mass: [(M+H)+]: 656

[0623]

[0624] [Synthesis Example 42] Synthesis of compound ETA-12

[0625]

[0626] 20 g (51.5 mmol, 1 eq) of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine, 36.1 g (61.8 mmol, 1.2 eq) of 4,4,5,5-tetramethyl-2-(3',4',5'-triphenyl-[1,1':2',1''-terphenyl]-3-yl)-1,3,2-dioxaborolane, 2.4 g (2.1 mmol, 0.04 eq) of Pd(PPh3)4, and 14.2 g (103.0 mmol, 2 eq) of K2CO3 were added to 400 ml of THF and 150 ml of H2O, and the mixture was heated and stirred under reflux for 6 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the precipitated solid was filtered and thoroughly dried. The solid was dissolved in MCB, filtered through silica gel, and purified by column chromatography to obtain compound ETA-12, 2,4-diphenyl-6-(4',5',6'-triphenyl-[1,1':2',1'':3'',1'''-quaterphenyl]-3'''-yl)-1,3,5-triazine (31.6 g, yield 80%).

[0627] Mass: [(M+H)+]: 766

[0628]

[0629] [Synthesis Example 43] Synthesis of compound ETA-13

[0630]

[0631] 20 g (43.2 mmol, 1 eq) of 4-([1,1'-biphenyl]-4-yl)-6-(3-bromophenyl)-2-phenylpyrimidine and 22.4 g (51.8 mmol, 1.2 eq) of 2-([1,1':2',1'':2'',1'''-quaterphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2.0 g (1.7 mmol, 0.04 eq) of Pd(PPh3)4, and 11.9 g (86.3 mmol, 2 eq) of K2CO3 were added to 400 ml of THF and 150 ml of H2O, and the mixture was heated and stirred under reflux for 6 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the precipitated solid was filtered and thoroughly dried. The solid was dissolved in MCB, filtered through silica gel, and purified by column chromatography to obtain compound ETA-13, 4-([1,1'-biphenyl]-4-yl)-6-([1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-3-yl)-2-phenylpyrimidine (22.0 g, yield 74%).

[0632] Mass: [(M+H)+]: 689

[0633]

[0634] [Synthesis Example 44] Synthesis of compound ETA-14

[0635]

[0636] 20 g (45.6 mmol, 1 eq) of 2-(3-bromophenyl)-4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazine and 23.7 g (54.8 mmol, 1.2 eq) of 2-([1,1':2',1'':2'',1'''-quaterphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2.1 g (1.8 mmol, 0.04 eq) of Pd(PPh3)4, and 12.6 g (91.3 mmol, 2 eq) of K2CO3 were added to 400 ml of THF and 150 ml of H2O, and the mixture was heated and stirred under reflux for 6 hours. After completion of the reaction, the mixture was deactivated with a sufficient amount of water, and the precipitated solid was filtered and thoroughly dried. The solid was dissolved in MCB, filtered through silica gel, and purified by column chromatography to obtain compound ETA-14, 2-([1,1':2',1'':2'',1''':2''',1''''-quinquephenyl]-3-yl)-4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazine (21.2 g, yield 70%).

[0637] Mass: [(M+H)+]: 664

[0638]

[0639] [Synthesis Example 45] Synthesis of compound ETA-15

[0640]

[0641] 25 g (59.5 mmol, 1 eq) of 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine, 21.0 g (65.5 mmol, 1.1 eq) of 2-(9,9-dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.4 g (1.8 mmol, 0.03 eq) of Pd(OAc)2, 2.8 g (6.0 mmol, 0.10 eq) of Xphos, and 16.5 g (119.1 mmol, 2 eq) of K2CO3 were added to 400 ml of toluene, 100 ml of EtOH, and 100 ml of H2O, and heated and stirred under reflux for 7 hours. After the reaction was completed, the precipitated solid was filtered and thoroughly dried after being deactivated with a sufficient amount of water. The solid was dissolved in MCB, filtered through silica gel, purified by column chromatography, and concentrated. The concentrated solid was dissolved in toluene, and HX was added dropwise. The obtained solid was filtered to obtain compound ETA-15, 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (26.5 g, yield 77%).

[0642] Mass: [(M+H)+]: 578

[0643]

[0644] [Synthesis Example 46] Synthesis of compound ETA-16

[0645]

[0646] 2-(3-(3-chloronaphthalen-1-yl)phenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine 25g (48.1mmol, 1eq) and 2-(9,9-dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 16.9g (52.9mmol, 1.1eq), Pd(OAc)2 0.3g (1.4mmol, 0.03eq), Xphos 2.3g (4.8mmol, 0.10eq), K2CO3 13.3g (96.1mmol, 2eq) were added to 400ml of toluene, 100ml of EtOH, and 100ml of H2O, and heated and stirred under reflux for 7 hours. After completion of the reaction, the precipitated solid was filtered and thoroughly dried after being inactivated with a sufficient amount of water. The solid was dissolved in MCB, filtered through silica gel, purified by column chromatography, and concentrated. The concentrated solid was dissolved in toluene, and HX was added dropwise. The obtained solid was filtered to obtain compound ETA-16, 2-(3-(3-(9,9-dimethyl-9H-fluoren-2-yl)naphthalen-1-yl)phenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (24.4 g, yield 75%).

[0647] Mass: [(M+H)+]: 678

[0648]

[0649] [Preparation (calculation) example]

[0650] The physical properties of the compound synthesized in the above synthetic example were calculated according to the method described below and are shown in Table 1 below.

[0651] Specifically, the HOMO energy level, LUMO energy level, and singlet (S1) and triplet (T1) energies of the compounds used in the present invention were each calculated according to the Gaussian calculation formula (#B3LYP / 6-31G*). In addition, the HOMO energy level and LUMO energy level of each compound were each expressed as an absolute value. At this time, the basic calculation method of each property was used using the Schrödinger program (Schrㆆdinger software release 2022-3), and among the density functional theory (Density Functional Theory, DFT), the B3LYP (Becke, 3-parameter, Lee-Yang-Parr) functional calculation method was used, and 6-31G* was used as the basis set.

[0652] Material HOMOLUMOS1T1 First host BPH-014.940.933.583.02 BPH-024.930.743.723.02 BPH-034.750.773.582.85 BPH-045.060.953.583.08 BPH-055.441.253.623.10 BPH-065.260.883.853.0 8BPH-074.971.323.242.58BPH-084.920.783.612.82BPH-094.921.273.152.63 BPH-105.011.033.482.58BPH-114.931.133.522.71BPH-124.761.193.122.492nd HostBNH-015.751.863.323.12BNH-025.551.703.253.06BNH-035.661.883.203.05BNH-045.611.643.402.97BNH-055.391.942.972.80BNH-065.771.903.293.03BNH-075.751.953.252.47BNH-085.321.932.892.41BNH-095.351.872.932.32BNH-105.392.012.902.391st DopantPTB-054.711.312.842.61PTB-064.811.352.782.58PTB-074.671.292.822.60PTB-084.531.702.372.172nd Dopant BD-054.681.043.112.64BD-064.771.083.152.67BD-074.681.023.132.63BD-084.580.983.082.59Electron transport auxiliary layer ETA-015.891.893.572.83ETA-025.411.793.262.34ETA-035.661.803.452.57ETA-045.521.973.032.82ETA-055.821.76 3.612.99ETA-066.001.863.662.82ETA-076.101.843.762.96ETA-085.601.813.252.81ETA-095.452.142.902.44ET A-105.561.853.202.48ETA-115.581.743.362.99ETA-125.811.793.692.97ETA-135.941.653.802.85ETA-145.811.813.492.47ETA-155.581.823.442.83ETA-165.431.923.192.49.

[0653] At this time, the structure of each compound used in Examples 1 to 27 of the present invention is as follows.

[0654]

[0655]

[0656]

[0657]

[0658]

[0659] In addition, each compound used in the present examples and comparative examples is as follows.

[0660]

[0661]

[0662] [Examples 1-27] Fabrication of blue organic electroluminescent devices

[0663] After the compound synthesized in the above synthesis example was purified by high purity sublimation using a commonly known method, a blue organic electroluminescent device was manufactured according to the process below.

[0664] First, a glass substrate coated with a 1200 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then transferred to a UV OZONE cleaner (Power Sonic 405, Hwasin Tech). The substrate was then cleaned for 5 minutes using UV and transferred to a vacuum deposition machine.

[0665] On the ITO transparent electrode prepared as above, an organic electroluminescent device was manufactured by stacking HI + 2% HAT-CN6 (10 Å) / HI (600 Å) / EB (200 Å) / 88 wt% host (first host: second host = 40:60 weight ratio) + 10 wt% first dopant + 2 wt% second dopant (300 Å) / electron transport auxiliary layer (50 Å) / T2T + Liq (1:1)(300 Å) / LiF (10 Å) / Al (200 Å) in that order.

[0666] At this time, the first host, second host, first dopant, second dopant, and electron transport auxiliary layer materials of the light-emitting layer used in Examples 1 to 27 are as shown in Table 2 below.

[0667]

[0668] [Comparative Examples 1-11] Fabrication of Blue Organic Electroluminescent Devices

[0669] Organic electroluminescent devices of Comparative Examples 1 to 11 were manufactured in the same manner as in Example 1, except that the materials of the light-emitting layer and the electron transport auxiliary layer were changed as shown in Table 2 below.

[0670]

[0671] [Comparative Examples 12-20] Fabrication of Blue Organic Electroluminescent Devices

[0672] Organic electroluminescent devices of Comparative Examples 12 to 20 were manufactured in the same manner as in Example 1, except that the electron transport auxiliary layer was not included and the device configuration was changed as follows.

[0673] Comparative Examples 12 to 20 were prepared by stacking HI + 2% HAT-CN6 (10 Å) / HI (600 Å) / EB (200 Å) / 88 wt% host (first host: second host = 40:60 weight ratio) + 10 wt% first dopant + 2 wt% second dopant (300 Å) / T2T + Liq (1:1)(300 Å) / LiF (10 Å) / Al (200 Å) in that order on an ITO transparent electrode prepared as described above, thereby manufacturing an organic electroluminescent device.

[0674]

[0675] [Evaluation example]

[0676] For the organic electroluminescent devices manufactured in Examples 1 to 27 and Comparative Examples 1 to 20, the driving voltage, current efficiency, lifespan, emission wavelength, and half-width at a current density of 10 mA / cm2 were measured, and the results are shown in Table 2 below.

[0677] Experimental Example 1 Host Second Host Second Dopant First Dopant Electron Transport Auxiliary Layer Voltage (V) Efficiency (cd / A) Lifetime (T90) Emission Wavelength (nm) Half-width (nm) Comparative Example 1 BPH-07BNH-05BD-05PTB-05ETA-014.61019946046 Comparative Example 2 BPH-06BNH-05BD-05PTB-07ETA-084.6989446348 Comparative Example 3 BPH-07BNH-05BD-06PTB-05ETA-114.610010146247 Comparative Example 4 BPH-07BNH-09BD-08PTB-07ETA-114.7856 946547Comparative Example 5BPH-01BNH-02BD-06PTB-06ETA-024.7655746948Comparative Example 6BPH-02BNH-04BD-06PTB-05ETA-034.7747246548Comparative Example 7BPH-09BNH-08BD-07PTB-05ETA-064.7836646551Comparative Example 8BPH-09BNH-08BD-06PTB-05ETA-074.7806046551Comparative Example 9BPH-01BNH-01BD-08PTB-07ETA-094.8543346347Comparative Example 10BPH-01B NH-02BD-08PTB-06ETA-144.9675946347Comparative Example 11BPH-07BNH-05BD-06PTB-05ETA-164.8635446447Comparative Example 12BPH-01BNH-01BD-05PTB-05-4.4759146046Comparative Example 13BPH-01BNH-01BD-08PTB-07-4.5809746046Comparative Example 14BPH-04BNH-06BD-06PTB-05-4.48310146046Comparative Example 15BPH-01BNH-02BD-05PTB-07-4.48410546 046Comparative Example 16BPH-06BNH-03BD-06PTB-05-4.4889246046Comparative Example 17BPH-08BNH-06BD-05PTB-07-4.3899946046Comparative Example 18BPH-02BNH-03BD-06PTB-06-4.4909246046Comparative Example 19BPH-02BNH-03BD-05PTB-07-4.4858846046Comparative Example 20BPH-04BNH-06BD-06PTB-05-4.3809046046Example 1BPH-01BNH-01BD-05PTB-05ETA-014.312314046046Embodiment 2BPH-01BNH-02BD-05PTB-07ETA-014.313715746046Embodiment 3BPH-02BNH-03BD-06PTB-05ETA-014.312812946046Embodiment 4BPH-01BNH-01BD-08PTB-07ETA-044.412612746046Embodiment 5BPH-02BNH-03BD-06PTB-06ETA-044.414215546046Embodiment 6BPH-02BNH-03BD-06PTB-05ETA-044.313614746046Embodiment 7BPH-04BNH-06BD-06PTB-05ETA-054.214415046046Example 8BPH-02BNH-03BD-07PTB-05ETA-054.213514446046Example 9BPH-08BNH-04BD-06PTB-05ETA-054.413816146046Example 10BPH-01BNH-02BD-05PTB-07ETA-064.414215546046Example 11BPH-02BNH-03BD-06PTB-05ETA-064.313513946046Example 12BPH-06BNH-0 3BD-06PTB-05ETA-074.314513346046Example 13BPH-01BNH-02BD-05PTB-05ETA-074.414014846046Example 14BPH-02BNH-03BD-05PTB-07ETA-084.213213846046Example 15BPH-06BNH-03BD-06PTB-05ETA-084.313614446046Example 16BPH-01BNH-02BD-05PTB-05ETA-084.313915346046Example 17BPH-08BNH-06BD-05PTB- 07ETA-114.213816146046Example 18BPH-04BNH-06BD-06PTB-05ETA-114.214814646046Example 19BPH-02BNH-03BD-06PTB-06ETA-124.213912846046Example 20BPH-08BNH-04BD-06PTB-05ETA-124.313514246046Example 21BPH-01BNH-02BD-07PTB-05ETA-124.314512646046Example 22BPH-02BNH-03BD-05PTB-07ETA-134.213613346046Embodiment 23BPH-02BNH-04BD-06PTB-05ETA-134.313414346046Embodiment 24BPH-04BNH-06BD-06PTB-06ETA-134.214115746046Embodiment 25BPH-04BNH-06BD-06PTB-05ETA-154.312412946046Embodiment 26BPH-01BNH-02BD-05PTB-05ETA-154.412914046046Embodiment 27BPH-01BNH-01BD-08PTB-07ETA-154.312612746046.

[0678] As described in Table 2 above, it was confirmed that the organic electroluminescent devices of Examples 1 to 27, which essentially include the first and second hosts, the first and second dopants, and the electron transport auxiliary layers, which are adjusted to predetermined properties, have remarkable effects in terms of driving voltage, efficiency characteristics, and lifespan characteristics of the devices, compared to the organic electroluminescent devices of Comparative Examples 1 to 20, which do not include at least one of the essential components of the present invention. Specifically, in the case of Comparative Examples 7 to 8, which include an emission layer having a low triplet (T1) energy level of the host material, it was confirmed that the efficiency and lifespan characteristics of the devices were significantly reduced. In addition, in the case of Comparative Examples 5 to 6 and 9 to 11, in which the T1 of the electron transport auxiliary layer is low, it was confirmed that the lifespan characteristics of the devices tended to decrease rapidly.

[0679] And in the case of Comparative Example 9 where the LUMO energy of the electron transport auxiliary layer is deep, the efficiency characteristics of the device tended to decrease or the driving voltage tended to increase. This is because the emission wavelength and half-width are maintained and the color deviation is not large due to the presence of the first dopant and the second dopant in the LUMO energy level of the first host that accepts electrons in the light-emitting layer, but it can be confirmed that the efficiency characteristics of the device are reduced when the energy level of the host is not within a certain range. In other words, it can be inferred that the energy transfer from the host to the dopant is not smooth, resulting in an overall increase in voltage, decrease in efficiency, and reduction in lifespan of the device.

[0680] In addition, as in Comparative Examples 2 to 4 and 7 to 8, it can be confirmed that the changes in the emission wavelength and the half-width are more prominent depending on the energy level of the host. This can be seen as the cause that the self-luminescence and triplet (T1) energy levels of the host are low, so that energy transfer to the dopant is not smooth, and therefore the wavelength of light is not uniform, the half-width increases, the color purity decreases, and the efficiency characteristics of the device decrease. In particular, when the energy levels of the first host and the second host are not controlled within a predetermined range, the device exhibits a disadvantage in terms of driving voltage. It can be seen that the driving voltage becomes disadvantageous due to the charge barrier generated by the difference in energy levels.

[0681] Likewise, when the triplet (T1) energy level of the host is low, the overall efficiency characteristics of the device decrease and the lifetime characteristics are greatly affected. This is because even if a sufficient amount of excitons are generated, the low triplet (T1) level causes self-luminescence of the host or loss due to triplet-triplet annihilation (TTA), which has a great impact on the decrease in the efficiency of the device. This non-radiative energy transfer releases heat energy throughout the device, accelerating the deterioration of the device. In addition, the voltage of the device is mainly affected by the LUMO energy, and the efficiency characteristics and lifetime characteristics of the device show prominent deviations depending on the triplet (T1) energy level.

[0682] In the light-emitting system of the above-described type, the energy levels and deviations between the layers constituting the device are important, and if even one of them does not satisfy the essential property values ​​according to the present invention, it is difficult to actually realize an excellent blue light-emitting device. Accordingly, the present invention includes a plurality of hosts, a plurality of hosts, and an electron transport auxiliary layer, and simultaneously has an appropriate HOMO energy level (HOMO), a LUMO energy level (LUMO), and a triplet (T1) energy level at which excitons are not inverted, and at the same time has a specific gap between each energy level as an essential component, so that optimized characteristics in terms of luminescence efficiency and lifespan characteristics of the blue phosphorescent light-emitting device can be secured, and in particular, it was confirmed that there is a large improvement in the overall efficiency and lifespan characteristics of the device depending on the LUMO energy level (LUMO), triplet (T1) energy level, and electron transfer performance of the electron transport auxiliary layer.

[0683] While the present invention has been described with reference to the aforementioned synthetic examples and working examples, it should be understood that these are merely illustrative and not limiting. Therefore, those skilled in the art will appreciate that various modifications and equivalent embodiments are possible. Consequently, the technical protection scope of the present invention should be defined by the technical spirit of the appended claims.

Claims

1. In 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 laminated, Including an electron transport auxiliary layer disposed between the above light-emitting layer and the electron transport region, The above light-emitting layer comprises different first hosts, second hosts, first dopants and second dopants, The above first dopant is a phosphorescent dopant containing platinum, The second dopant is a fluorescent dopant containing boron, The overlapping emission wavelength of the first dopant and the second dopant is 10 nm or more, The first host (H1), the second host (H2), the first dopant (D1) and the second dopant (D2) satisfy the conditions of the following equations (i) to (iv), respectively: (i) HOMO H1 < 5.5 eV (ii) HOMO H2 ≥ 5.5 eV (iii) 440 ≤ λmax D1 ≤ 490 (iv) 450 ≤ λmax D2 ≤ 500 (In the above formula, HOMO H1 and HOMO H2 are the absolute values ​​of the HOMO energy levels of the first and second host materials, respectively, calculated according to Gaussian, and λmax D1 and λmax D2 are the maximum emission wavelengths of the first dopant material and the second dopant material, respectively. The above electron transport auxiliary layer comprises a compound represented by the following chemical formula 5, The triplet energy (T1) of the first host H1 ), the triplet energy (T1) of the second host H2 ), and the triplet energy (T1) of the electron transport auxiliary layer aETL) are all characterized by an organic electroluminescent device having a luminescence intensity of 2.7 eV or higher: [Chemical Formula 5] In the above chemical formula 5, Y4 to Y6 are identical or different from each other and are each independently N or CR. 31 However, at least one of Y4 to Y6 is N, R 12 , R 31 , Ar8 and Ar9 are the same or different from each other, and each independently represents hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or can form a condensed ring by combining with any adjacent group, v is an integer from 1 to 4, L is a single bond, or C6~C 18 is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms, A is C, Si, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40Alkynyl group, C3~C 40 Cycloalkyl group of , heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or can form a condensed ring by combining with any adjacent group, The above L's arylene group, heteroarylene group, and the above R 12 , R 31 , Ar8~Ar9 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylamine group of A are each independently deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C60 Arylphosphine oxide group and C6~C 60 It may be substituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they may be the same or different from each other.

2. In paragraph 1, The singlet energy of the first host (S1) H1 ) and the singlet of the second host (S1) H2 ) Organic electroluminescent devices, all of which have energies of 3.2 eV or higher.

3. In paragraph 1, The triplet energy (T1) of the first host H1 ) and the triplet of the second host (T1 H2 ) Organic electroluminescent devices, all of which have energies of 2.8 eV or higher.

4. In paragraph 1, An organic electroluminescent device, wherein the mixing ratio of the first host and the second host is 2:8 to 8:2 by weight.

5. In paragraph 1, The above first host is a hole transporting compound that does not contain an electron transporting moiety, An organic electroluminescent device, wherein the second host is an electron-transporting compound comprising at least one electron-transporting moiety.

6. In paragraph 1, The above first dopant is an organic electroluminescent device which is a compound represented by the following chemical formula 3: [Chemical Formula 3] In the above chemical formula 3, M is platinum, R5 to R7 are the same or different and each independently represents a single bond, O, S, C2~C. 30 Alkylene group, C6~C 18 is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 18 nuclear atoms, B, C, D and E are the same or different from each other and each independently represents hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, However, at least one of B, C, D and E comprises a moiety represented by 3A below, [Chemical Formula 3A] In the above chemical formula 3A, * indicates the position where it is combined with M, r can be an integer from 0 to 4, R8 is hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C3~C 40Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or can form a condensed ring by combining with any adjacent group, wherein when r is 2 or more, multiple R8s are the same or different from each other, Ar4 and Ar5 are the same or different from each other, and each independently represents hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or can form a condensed ring with any one selected from adjacent B, C, D and E, G is C6~C 60 Aryl group of C6~C 60 is selected from the group consisting of an arylene group and a heteroarylene group having 5 to 60 nuclear atoms, wherein when r is 2 or more, multiple Gs are the same or different from each other, B, C, D, E of the above chemical formula 3, and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group of R8, Ar4~Ar5 in the above chemical formula 3A; and the aryl group, arylene group and heteroarylene group of G in the above chemical formula 3A; each independently represent deuterium (D), halogen, cyano group, nitro group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 It can be substituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they can be the same or different from each other.

7. In paragraph 1, An organic electroluminescent device, wherein the second dopant has an absorption wavelength that overlaps the emission wavelength of the first dopant by 10 nm or more.

8. In paragraph 1, The above second dopant is an organic electroluminescent device which is a compound represented by the following chemical formula 4: [Chemical Formula 4] In the above chemical formula 4, R9 to R 11 , Ar6 and Ar7 are the same or different from each other, and each independently represents hydrogen, deuterium, halogen, cyano group, nitro group, amino group, C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of , heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C 40 Alkyloxy group, C6~C 60 Aryloxy group of C3~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 is selected from the group consisting of arylamine groups, or can form a condensed ring by combining with any adjacent group, s and t are integers from 0 to 4, respectively. u is an integer from 0 to 3, Above R9~R 11 , Ar6~Ar7, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group, and an arylamine group are each independently deuterium (D), a halogen, a cyano group, a nitro group, a C1~C 40 Alkyl group of C2~C 40 Alkenyl group of C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl group of, heterocycloalkyl group having 3 to 40 nuclear atoms, C6~C 60 Aryl group of , heteroaryl group having 5 to 60 nuclear atoms, C1~C40 Alkyloxy group, C6~C 60 Aryloxy group of C1~C 40 Alkylsilyl group, C6~C 60 Arylsilyl group, C1~C 40 Alkyl boron group, C6~C 60 Aryl boron group, C6~C 60 Arylphosphine group, C6~C 60 Arylphosphine oxide group and C6~C 60 It can be substituted with one or more substituents selected from the group consisting of arylamine groups, and when there are multiple substituents, they can be the same or different from each other.

9. In paragraph 1, An organic electroluminescent device, wherein the first dopant is included in an amount of 15 wt% or less based on 100 wt% of the light-emitting layer.

10. In paragraph 1, An organic electroluminescent device, wherein the second dopant is included in an amount of 4 wt% or less based on 100 wt% of the light-emitting layer.

11. In paragraph 1, An organic electroluminescent device, wherein the content ratio of the entire host and the entire dopant in the above-mentioned light-emitting layer is 70:30 to 99.5:0.5 by weight.

12. In paragraph 1, The above electron transport auxiliary layer (aETL) is an organic electroluminescent device satisfying the conditions of the following formulas (v) to (vii): (v) HOMO aETL ≥ 5.5 eV (vi) LUMO aETL ≤ 2.0 eV (vii) T1 aETL ≥ 2.8 eV (In the above formula, HOMO aETL , LUMO aETL and T1 aETLare the absolute value of the HOMO energy level, the absolute value of the LUMO energy level, and the triplet energy of the electron transport auxiliary layer material, respectively, calculated according to Gaussian.

13. In paragraph 1, An organic electroluminescent device, wherein the first host (H1) and the electron transport auxiliary layer (aETL) satisfy the condition of the following formula (viii). (viii) HOMO aETL - HOMO H1 ≥ 0.3 eV (In the above formula, HOMO aETL silver The absolute value of the HOMO energy level of the electron transport auxiliary layer material calculated according to Gaussian, and HOMO H1 is the absolute value of the HOMO energy level of the first host material calculated according to Gaussian.

14. In paragraph 1, An organic electroluminescent device, wherein the first host (H1) and the electron transport auxiliary layer (aETL) satisfy the condition of the following equation (ix). (ix) LUMO aETL - LUMO H1 ≥ 0.3 eV (In the above formula, LUMO aETL silver The absolute value of the LUMO energy level of the electron transport auxiliary layer material calculated according to Gaussian, LUMO H1 is the absolute value of the LUMO energy level of the first host material calculated according to Gaussian.

15. In paragraph 1, An organic electroluminescent device, wherein the second host (H2) and the electron transport auxiliary layer (aETL) satisfy the condition of the following equation (x). (x) LUMO aETL - LUMO H2 ≤ 0.2 eV (In the above formula, LUMO aETL silver The absolute value of the LUMO energy level of the electron transport auxiliary layer material calculated according to the Gaussian calculation formula, and LUMO H2 is the absolute value of the LUMO energy level of the second host material calculated according to Gaussian.

16. In paragraph 1, An organic electroluminescent device, wherein the electron transport region includes at least one of an electron transport layer and an electron injection layer.

17. In paragraph 1, An organic electroluminescent device, wherein the hole transport region includes at least one of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer.

18. In paragraph 1, The above organic electroluminescent device comprises a plurality of light-emitting layer stacks including at least one light-emitting layer, An organic electroluminescent device, wherein at least one light-emitting layer comprises the first host, the second host, the first dopant and the second dopant.

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