Organic compound and organic electroluminescent device comprising same

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device comprising same and, more specifically, to: an organic compound that is excellent in terms of characteristics such as electron injection and transport ability, light emission ability, electrochemical stability, and thermal stability; and an organic electroluminescent device which includes the organic compound in one or more organic material layers, and thus is improved in terms of characteristics such as luminous efficiency, driving voltage, and lifespan.

Description

Organic compounds and organic electroluminescent devices containing the same

[0001] The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more specifically, to a novel compound and an organic electroluminescent device in which characteristics such as luminous efficiency, driving voltage, and lifespan are improved by including the same in one or more organic layers.

[0002] In an organic electroluminescent device, when a voltage is applied between two electrodes, 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 light is emitted when these excitons fall to the ground state. At this time, the materials used as the organic layer can be classified according to their function into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc.

[0003] Luminous materials can be classified according to their emission color into blue, green, and red luminous materials, and yellow and orange luminous materials for realizing better natural colors. In addition, host / dopant systems can be used as luminous materials to increase color purity and luminescence efficiency through energy transfer.

[0004] Dopant materials can be divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. At this time, since the development of phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescence, research is being conducted extensively not only on phosphorescent dopants but also on phosphorescent host materials.

[0005] To date, NPB, BCP, and Alq3 are widely known as materials for hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, and anthracene derivatives are reported as materials for emissive layers. In particular, metal complex compounds containing Ir, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, which have advantages in terms of efficiency improvement among emissive layer materials, are used as blue, green, and red phosphorescent dopant materials, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.

[0006] However, while conventional organic layer materials offer advantages in terms of luminescence properties, their low glass transition temperatures result in very poor thermal stability, which is unsatisfactory in terms of the lifespan of organic electroluminescent devices. Therefore, the development of high-performance organic layer materials is required.

[0007] The present invention aims to provide a novel compound that has excellent heat resistance, carrier transport capacity, luminescence capacity, etc., and can be used as an organic layer material for an organic electroluminescent device, specifically as a light-emitting layer material, a lifespan improvement layer material, a light-emitting auxiliary layer material, or an electron transport layer material.

[0008] In addition, the present invention also aims to provide an organic electroluminescent device comprising the novel compound described above, having a low driving voltage, high luminous efficiency, and an improved lifespan.

[0009] The present invention has a technical objective of providing a novel compound that has excellent heat resistance, carrier transport capacity, luminescence capacity, etc., and can be used as an organic layer material for an organic electroluminescent device, specifically as an electron transport layer, an electron transport auxiliary layer, or a luminescent layer.

[0010] In addition, the present invention has another technical objective of providing an organic electroluminescent device comprising the novel compound described above, having a low driving voltage, high luminous efficiency, and improved lifespan.

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

[0012] The present invention aims to provide a novel organic compound that can be applied to organic electroluminescent devices and exhibits excellent hole, electron injection and transport capabilities, and luminescence capabilities.

[0013] In addition, another objective of the present invention is to provide an organic electroluminescent device comprising the novel organic compound described above, which exhibits a low driving voltage and high luminous efficiency and has an improved lifespan.

[0014] To achieve the above objective, the present invention provides a compound represented by the following chemical formula 1.

[0015] [Chemical Formula 1]

[0016]

[0017] In the above chemical formula 1,

[0018] X1 to X 14 They are identical or different from each other, and 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 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 It is an aryl group or a heteroaryl group having 5 to 60 nuclei, and

[0019] X1 to X 14 At least one of them is cyanobacteria, and

[0020] X1 to X 14One of them combines with L, and

[0021] L is a single bond or C5~C 60 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 40 nuclei,

[0022] The above A is selected from the moiety of A-1 to A-4 below, and

[0023]

[0024] * represents the part connected to L of the above chemical formula 1, and

[0025] Y1 to Y 21 They are identical or different from one another, and each independently is CR' or N, wherein Y1 to Y5 comprise 1 to 3 Ns, Y6 and Y7 comprise 1 or 2 Ns, and Y8 to Y 14 It includes 1 to 3 Ns, and Y 15 to Y 21 It includes 1 to 3 Ns. The R's are identical or different from each other and 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 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 an aryl group, a heteroaryl group having 5 to 60 nuclei, and

[0026] The above X1 to X 14 C1~C of 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 The aryl group of, a heteroaryl group having 5 to 60 nuclei, and the C5~C of the above L 60The arylene group and the heteroarylene group having 5 to 40 nuclei, and the moiety of A-1 to A-4 of A 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 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei. In this case, if there are multiple substituents, they may be identical or different from each other, may combine or condense to form a condensed ring, and 1 to 3 carbons may be substituted with N, O, S, or Se.

[0027] In addition, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by the chemical formula 1.

[0028] Here, the organic layer comprising the compound represented by Chemical Formula 1 may be selected from the group consisting of a light-emitting layer, a light-emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, a lifetime improvement layer, an electron transport layer, and an electron transport auxiliary layer. In this case, the compound represented by Chemical Formula 1 may be included as at least one material among the phosphorescent host material of the light-emitting layer, the electron transport layer, and the electron transport auxiliary layer.

[0029] For example, in one embodiment of the present invention, the compound represented by Chemical Formula 1 can be used as an organic layer material for an organic electroluminescent device because it has excellent electron transport ability, luminescence ability, heat resistance, etc.

[0030] In particular, when a compound represented by Chemical Formula 1 of the present invention is used as an electron transport layer or an electron transport auxiliary layer material, it can exhibit high thermal stability, low driving voltage, fast mobility, high current efficiency, and long lifespan characteristics compared to conventional electron transport materials.

[0031] Accordingly, an organic electroluminescent device containing the compound of Chemical Formula 1 can have excellent luminescence performance, low driving voltage, long lifespan, and high efficiency, and thus can be effectively applied to full-color display panels, etc.

[0032] The effects according to the present invention are not limited to those exemplified above, and a wider variety of effects are included in this specification.

[0033] The present invention will be described in detail below.

[0034] <New Organic Compounds>

[0035] The present invention provides a novel compound that exhibits excellent electron transport capacity, luminescence capacity, and thermal stability, thereby enabling the device to display low voltage, high luminescence efficiency, and long lifespan characteristics.

[0036] According to the present invention, a compound represented by the following chemical formula 1 is an o-terphenyl having an electron donating group (EDG) (e.g., X1 to X 14 It has a basic framework structure centered on an aromatic ring substituted with a cyano group having an electron withdrawing group (EWG) in a moiety containing a ring, wherein a nitrogen-containing heteroaromatic ring (e.g., azine, Y1~Y5 containing ring) represented by A of Chemical Formula 1 below is directly connected or connected through a separate linker (e.g., L).

[0037] [Chemical Formula 1]

[0038]

[0039] Specifically, the compound of Chemical Formula 1 above is an o-terphenyl (e.g., X1~X) having EDG properties in its molecular skeleton structure. 14 It includes a ring containing a cyano group (CN) substituted on the o-terphenyl group, and a moiety unit (nitrogen-containing heteroaromatic ring) selected from the following structural formulas is introduced on one side of the o-terphenyl group.

[0040]

[0041] * represents the part connected to L of the above chemical formula 1.

[0042] Here, the aromatic ring corresponding to the o-terphenyl group, when unsubstituted, possesses electron-donating properties, allowing it to readily accept electrons from the cathode and smoothly transfer electrons to the light-emitting layer. This affects the transfer speed and, at the same time, minimizes damage that may occur due to excess holes that are not used in the light-emitting layer, thereby lowering the driving voltage of the device and inducing high efficiency and a long lifespan.

[0043] In addition, if one or more of the hydrogens of the o-terphenyl group are substituted with cyano groups, the cyano group exhibits bipolar characteristics due to its properties as an electron acceptor. Furthermore, the nitrogen-containing heteroaromatic ring represented by A in Chemical Formula 1 is used as an electron acceptor. Accordingly, the compound of Chemical Formula 1 plays a role in controlling the LUMO value suitable for an electron transport layer or an electron transport auxiliary layer, and plays a role in enabling the smooth transfer of electrons to the light-emitting layer, thereby improving the efficiency and lifespan characteristics of the device.

[0044] As described above, when the compound represented by Formula 1 of the present invention is applied as an organic layer material, preferably a light-emitting layer material (a blue, green and / or red phosphorescent host material), an electron transport layer / injection layer material, a light-emitting auxiliary layer material, or a lifespan improvement layer material of an organic electroluminescent device, the performance and lifespan characteristics of the organic electroluminescent device can be improved. In particular, when the compound of the present invention is utilized as an electron transport layer or an electron transport auxiliary layer material, a significantly superior performance improvement effect can be expected in terms of the efficiency, driving voltage, and lifespan characteristics of the device. Consequently, such an organic electroluminescent device can maximize the performance of a full-color organic light-emitting panel.

[0045] According to the present invention, the compound represented by the following chemical formula 1 has a basic skeletal structure centered on a moiety in which a cyano group with excellent electron transport capacity and EWG characteristics is substituted on an o-terphenyl group, wherein a moiety represented by A in chemical formula 1, such as a nitrogen-containing heteroaromatic ring (e.g., azine, a ring containing Y1 to Y5), is directly connected or connected through a separate linker (e.g., L).

[0046] [Chemical Formula 1]

[0047]

[0048] The aromatic ring containing the ortho-terphenyl group is a bipolar aromatic ring substituted with at least one cyano group. One example of the aromatic ring is X1 to X 14 They are identical or different from each other, and 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 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 It is an aryl group or a heteroaryl group having 5 to 60 nuclei, and X1 to X 14 At least one of 1 to 3, 1 or 2, one may be a cyano group, and X1 to X 14 Any one of them can combine with L. In this case, X1 to X that become a cyano group 14 X1 to X that combine with at least one of L and L 14 None of them are identical.

[0049] In this way, a dipolar compound combining the electron-donating properties of an o-terphenyl group and the electron-attracting properties of a cyano group can enable efficient electron transport by having the o-terphenyl group provide an electron-rich π-electron system and the cyano group act as a strong electron-attractor, thereby increasing the electron affinity of the molecule and regulating the LUMO energy level.

[0050] As an example of one embodiment of the nitrogen-containing heteroaromatic ring A represented by A of Chemical Formula 1 above, the nitrogen-containing hetero ring (e.g., a ring containing Y1 to Y5) can be further specified as any one selected from the moiety A-1 to A-4 below. However, it is not limited thereto.

[0051]

[0052] * represents the part connected to L of the above chemical formula 1, and

[0053] Y1 to Y 21 They are identical or different from one another, and each independently is CR' or N, wherein Y1 to Y5 comprise 1 to 3 Ns, Y6 and Y7 comprise 1 or 2 Ns, and Y8 to Y 14 It includes 1 to 3 Ns, and Y 15 to Y 21 It may include 1 to 3 Ns.

[0054] At this time, the above R' are identical or different from each other, and 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 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 It can be an aryl group, or a heteroaryl group with 5 to 60 nuclei.

[0055] Also, here, the above X1 to X 14 C1~C of 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 The aryl group of, a heteroaryl group having 5 to 60 nuclei; C5~C of the above L 60 The arylene group and the heteroarylene group having 5 to 40 nuclei; the moiety of A-1 to A-4 of the above A; 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 40cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 The aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It can be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei. In this case, if there are multiple substituents, they may be identical or different from each other, and may combine or condense to form a condensed ring, and 1 to 3 carbons may be substituted with N, O, S, or Se. That is, a heteroaromatic ring may be formed.

[0056] For example, the compound represented by Chemical Formula 1 above may be embodied as a compound represented by any one of Chemical Formulas 2 to 7 below. However, it is not limited thereto.

[0057] [Chemical Formula 2]

[0058]

[0059] [Chemical Formula 3]

[0060]

[0061] [Chemical Formula 4]

[0062]

[0063] [Chemical Formula 5]

[0064]

[0065] [Chemical Formula 6]

[0066]

[0067] [Chemical Formula 7]

[0068]

[0069] For example, the linker L connecting the o-terphenyl group and the nitrogen-containing heterocyclic group in Chemical Formula 1 above may be embodied in any one of the following structural formulas. However, it is not limited thereto.

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081] * represents X1 to X of the above chemical formula 1. 14 It refers to the part connected to any one of them.

[0082] For example, (e.g., A of Chemical Formula 1) may be any one selected from the following structural formulas. However, it is not limited thereto.

[0083]

[0084]

[0085]

[0086]

[0087] * represents the part connected to chemical formula 1.

[0088] In addition, the above moiety is 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 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei. As a more specific example, the compound of Formula 1 may be embodied in any one selected from the group consisting of compounds 001 to 416.

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115] In the present invention, “number of nuclei” refers to the number of ring atoms constituting a ring structure, and said nuclei may be carbon or heteroatoms selected from the group consisting of N, O, S, and Se. For example, the number of nuclei of pyridine refers to 6, including 5 C and 1 N constituting the pyridine ring.

[0116] In the present invention, “alkyl” means a monovalent substituent derived from a straight-chain or side-chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

[0117] In the present invention, “alkenyl” refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

[0118] In the present invention, “alkynyl” refers to a monovalent substituent derived from a straight-chain or side-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.

[0119] In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms, consisting of a single ring or a combination of two or more rings. Additionally, forms in which two or more rings are simply penantated or condensed may also be included. Examples of such aryls include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0120] In the present invention, “heteroaryl” refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclei. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Additionally, forms in which two or more rings are simply penant or condensed with each other may be included, and furthermore, forms condensed with an aryl group may also be included. Examples of such heteroaryls include, but are not limited to, 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl.

[0121] In the present invention, “aryloxy” refers to a monovalent substituent represented by RO-, where R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, etc., but are not limited thereto.

[0122] In the present invention, “alkyloxy” refers to a monovalent substituent represented by R’O-, where R’ means an alkyl group 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, pentoxy, etc.

[0123] In the present invention, “arylamine” means an amine substituted with an aryl group having 6 to 40 carbon atoms.

[0124] In the present invention, “cycloalkyl” refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0125] In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclei, wherein one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Examples of such heterocycloalkyls include, but are not limited to, morpholine and piperazine.

[0126] In the present invention, “alkylsilyl” means a silyl substituted with an alkyl group having 1 to 40 carbon atoms, and “arylsilyl” means a silyl substituted with an aryl group having 5 to 40 carbon atoms.

[0127] In the present invention, “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

[0128]

[0129] Electron Transport Layer Material

[0130] The present invention provides an electron transport layer comprising a compound represented by the above chemical formula 1.

[0131] The electron transport layer (ETL) described above serves to move electrons injected from the cathode to an adjacent layer, specifically the light-emitting layer.

[0132] The compound represented by the above chemical formula 1 may be used alone as an electron transport layer (ETL) material, or may be used in combination with electron transport layer materials known in the art. Preferably, it is used alone.

[0133] The electron transport layer material that can be mixed with the compound of Formula 1 above includes electron transport materials commonly known in the art. Non-limiting examples of usable electron transport materials include oxazole compounds, isooxazole compounds, triazole compounds, isothiazole compounds, oxadiazole compounds, thiadiazole compounds, perylene compounds, aluminum complexes (e.g., Alq3 (tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. These may be used individually or in combination of two or more types.

[0134] In the present invention, when the compound of Formula 1 and the electron transport layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0135]

[0136] Electron Transport Auxiliary Layer Material

[0137] In addition, the present invention provides an electron transport assisting layer comprising a compound represented by the above chemical formula 1.

[0138] The electron transport layer is positioned between the light-emitting layer and the electron transport layer and serves to prevent excitons or holes generated in the light-emitting layer from diffusing into the electron transport layer.

[0139] The compound represented by the above chemical formula 1 may be used alone as an electron transport auxiliary layer material, or may be used in combination with electron transport layer materials known in the art. Preferably, it is used alone.

[0140] The electron transport auxiliary layer material that can be mixed with the compound of Chemical Formula 1 above includes electron transport materials commonly known in the art. For example, the electron transport auxiliary layer may include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), nitrogen-containing heterocyclic derivatives, etc.

[0141] In the present invention, when the compound of Formula 1 and the electron transport assisting layer material are mixed, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0142]

[0143] Organic Electroluminescent Device

[0144] Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising a compound represented by Formula 1 according to the present invention described above.

[0145] Specifically, the present invention relates to an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises a compound represented by Chemical Formula 1. In this case, the compound may be used alone or in a mixture of two or more types.

[0146] The above one or more organic layers may be one or more of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, a lifespan improvement layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one of the organic layers comprises a compound represented by Chemical Formula 1. Specifically, the organic layer comprising the compound of Chemical Formula 1 may be a light-emitting layer, a light-emitting auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and / or a lifespan improvement layer, and more specifically, it is preferably an electron transport layer or an electron transport auxiliary layer.

[0147] The light-emitting layer of the organic electroluminescent device according to the present invention comprises a host material and a dopant material, wherein the host material may include a compound of Formula 1. In addition, the light-emitting layer of the present invention may include a compound known in the art other than the compound of Formula 1 as a host.

[0148] When the compound represented by Chemical Formula 1 above is included as a material for the light-emitting layer of an organic electroluminescent device, preferably as a blue, green, or red phosphorescent host material, the binding force between holes and electrons in the light-emitting layer is increased, thereby improving the efficiency (luminous efficiency and power efficiency), lifespan, brightness, and driving voltage of the organic electroluminescent device. Specifically, it is preferable that the compound represented by Chemical Formula 1 above be included in the organic electroluminescent device as a green and / or red phosphorescent host, fluorescent host, or dopant material. In particular, it is preferable that the compound represented by Chemical Formula 1 of the present invention be a green phosphorescent exciplex N-type host material for the light-emitting layer having high efficiency.

[0149] The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially stacked. In this case, one or more of the hole injection layer, the hole transport layer, the light-emitting auxiliary layer, the light-emitting layer, the electron transport layer, and the electron injection layer may include a compound represented by Chemical Formula 1, and preferably, the light-emitting layer, more preferably, the phosphorescent host may include a compound represented by Chemical Formula 1. Meanwhile, an electron injection layer may be additionally stacked on the electron transport layer.

[0150] The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0151] The organic electroluminescent device of the present invention can be manufactured by forming an organic layer and an electrode using materials and methods known in the art, except that one or more of the aforementioned organic layers include a compound represented by Chemical Formula 1.

[0152] The above organic layer can be formed by vacuum deposition or solution coating. Examples of the above solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

[0153] The substrate used in the manufacture of the organic electroluminescent device of the present invention is not particularly limited, and examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

[0154] In addition, the anode material may be any anode material known in the art without limitation. Examples include metals or alloys thereof such as vanadium, chromium, copper, zinc, and gold; 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 or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited thereto.

[0155] In addition, the cathode material may be any cathode material known in the art without limitation. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multilayer structural materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0156] In addition, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not specifically limited, and ordinary materials known in the industry may be used without restriction.

[0157]

[0158] The present invention will be described in detail below through examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by the following examples.

[0159]

[0160] [Synthetic Example]

[0161]

[0162] [Synthesization Example 1] Synthesis of 3'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 009)

[0163]

[0164] 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0g, 25.8mmol), 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (9.8g, 25.8mmol), Pd(PPh3)4 (0.9g, 0.8mmol), and K2CO3 (10.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 3'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (11.4g, 20.3mmol, yield 79%).

[0165]

[0166] Mass : [(M+H) + ] :564

[0167]

[0168] [Synthesization Example 2] Synthesis of 5'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 015)

[0169]

[0170] 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0g, 25.8mmol), 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (9.8g, 25.8mmol), Pd(PPh3)4 (0.9g, 0.8mmol), and K2CO3 (10.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 5'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (11.3g, 20.1mmol, yield 78%).

[0171]

[0172] Mass : [(M+H) + ] :564

[0173]

[0174] [Synthesization Example 3] Synthesis of 4'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 018)

[0175]

[0176] 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0g, 25.8mmol), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (9.8g, 25.8mmol), Pd(PPh3)4 (0.9g, 0.8mmol), and K2CO3 (10.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 4'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (11.6 g, 20.6 mmol, yield 80%).

[0177]

[0178] Mass : [(M+H) + ] :564

[0179]

[0180] [Synthesization Example 4] Synthesis of 5'-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 033)

[0181]

[0182] 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0g, 25.8mmol), 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (9.8g, 25.8mmol), Pd(PPh3)4 (0.9g, 0.8mmol), and K2CO3 (10.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 5'-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (11.7 g, 20.9 mmol, yield 81%).

[0183]

[0184] Mass : [(M+H) + ] :564

[0185]

[0186] [Synthesization Example 5] Synthesis of 4'-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 036)

[0187]

[0188] 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0g, 25.8mmol), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (9.8g, 25.8mmol), Pd(PPh3)4 (0.9g, 0.8mmol), and K2CO3 (10.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 4'-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (11.3g, 20.1mmol, yield 78%).

[0189]

[0190] Mass : [(M+H) + ] :564

[0191]

[0192] [Synthesization Example 6] Synthesis of 5'-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 051)

[0193]

[0194] 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0g, 25.8mmol), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (9.8g, 25.8mmol), Pd(PPh3)4 (0.9g, 0.8mmol), and K2CO3 (10.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 5'-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (11.6 g, 20.6 mmol, yield 80%).

[0195]

[0196] Mass : [(M+H) + ] :564

[0197]

[0198] [Synthesization Example 7] Synthesis of 4'-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 054)

[0199]

[0200] 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0g, 25.8mmol), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (9.8g, 25.8mmol), Pd(PPh3)4 (0.9g, 0.8mmol), and K2CO3 (10.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 4'-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (11.3g, 20.1mmol, yield 78%).

[0201]

[0202] Mass : [(M+H) + ] :564

[0203]

[0204] [Synthesization Example 8] Synthesis of 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':2'',1'''-quaterphenyl]-4''-carbonitrile (Compound 061)

[0205]

[0206] 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0g, 25.8mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4'-carbonitrile (9.8g, 25.8mmol), Pd(PPh3)4 (0.9g, 0.8mmol), and K2CO3 (10.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':2'',1'''-quaterphenyl]-4''-carbonitrile (10.9 g, 19.3 mmol, yield 75%).

[0207]

[0208] Mass : [(M+H) + ] :564

[0209]

[0210] [Synthesization Example 9] Synthesis of 2'''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':2'',1'''-quaterphenyl]-4-carbonitrile (Compound 065)

[0211]

[0212] 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0g, 25.8mmol), 2''-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (9.8g, 25.8mmol), Pd(PPh3)4 (0.9g, 0.8mmol), and K2CO3 (10.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2'''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':2'',1'''-quaterphenyl]-4-carbonitrile (10.7 g, 19.1 mmol, yield 74%).

[0213]

[0214] Mass : [(M+H) + ] :564

[0215]

[0216] [Synthesization Example 10] Synthesis of 2'''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':3'',1'''-quaterphenyl]-5'-carbonitrile (Compound 072)

[0217]

[0218] 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0g, 25.8mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4'-carbonitrile (9.8g, 25.8mmol), Pd(PPh3)4 (0.9g, 0.8mmol), and K2CO3 (10.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2'''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':3'',1'''-quaterphenyl]-5'-carbonitrile (10.7 g, 19.1 mmol, yield 74%).

[0219]

[0220] Mass : [(M+H) + ] :564

[0221]

[0222] [Synthesization Example 11] Synthesis of 3'''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':3'',1'''-quaterphenyl]-4-carbonitrile (Compound 107)

[0223]

[0224] 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0g, 25.8mmol), 3''-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (9.8g, 25.8mmol), Pd(PPh3)4 (0.9g, 0.8mmol), and K2CO3 (10.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 3'''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':3'',1'''-quaterphenyl]-4-carbonitrile (10.7g, 19.1mmol, yield 74%).

[0225]

[0226] Mass : [(M+H) + ] :564

[0227]

[0228] [Synthesization Example 12] Synthesis of 3'''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':4'',1'''-quaterphenyl]-4-carbonitrile (Compound 116)

[0229]

[0230] 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0g, 25.8mmol), 4''-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (9.8g, 25.8mmol), Pd(PPh3)4 (0.9g, 0.8mmol), and K2CO3 (10.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 3'''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':4'',1'''-quaterphenyl]-4-carbonitrile (10.9g, 19.3mmol, yield 75%).

[0231]

[0232] Mass : [(M+H) + ] :564

[0233]

[0234] [Synthesization Example 13] Synthesis of 3''''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':2'',1''':2'',1''''-quinquephenyl]-4-carbonitrile (Compound 187)

[0235]

[0236] 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0g, 25.8mmol), 2''-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (9.8g, 25.8mmol), Pd(PPh3)4 (0.9g, 0.8mmol), and K2CO3 (10.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 3''''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':2'',1''':2'',1''''-quinquephenyl]-4-carbonitrile (11.2g, 19.8mmol, yield 77%).

[0237]

[0238] Mass : [(M+H) + ] :564

[0239]

[0240] [Synthesization Example 14] Synthesis of 3'''-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-phenyl-[1,1':3',1'':3'',1'''-quaterphenyl]-4-carbonitrile (Compound 195)

[0241]

[0242] 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (10.0g, 21.5mmol), 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':4',1''-terphenyl]-4-carbonitrile (8.2g, 21.5mmol), Pd(PPh3)4 (0.7g, 0.6mmol), and K2CO3 (8.9g, 64.6mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 3'''-(4,6-diphenyl-1,3,5-triazin-2-yl)-4'-phenyl-[1,1':3',1'':3'',1'''-quaterphenyl]-4-carbonitrile (9.2g, 16.4mmol, yield 76%).

[0243]

[0244] Mass : [(M+H) + ] :564

[0245]

[0246] [Synthesization Example 15] Synthesis of 4''''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':2'',1''':2'',1''''-quinquephenyl]-4-carbonitrile (Compound 218)

[0247]

[0248] 2-(2'-bromo-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (10.0g, 21.5mmol) and 3-(4,4,5,5-tetramethyl-1,32''-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4'-carbonitrile (8.2g, 21.5mmol) and Pd(PPh3)4 (0.7g, 0.6mmol) and K2CO3 (8.9g, 64.6mmol) in 150ml of Toluene and Ethanol. 22.5 ml was added to 22.5 ml of water and heated and stirred under reflux for 2 hours. After the reaction was complete, it was extracted with methylene chloride, the extracted organic layer was dehydrated with magnesium sulfate, concentrated, and purified by column chromatography to obtain 4''''-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1':2',1'':2'',1''':2'',1''''-quinquephenyl]-4-carbonitrile (9.1 g, 16.2 mmol, yield 75%).

[0249]

[0250] Mass : [(M+H) + ] :564

[0251]

[0252] [Synthesization Example 16] Synthesis of 5'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 297)

[0253]

[0254] 2-([1,1'-biphenyl]-4-yl)-4-(2-bromophenyl)-6-phenyl-1,3,5-triazine (10.0g, 21.5mmol), 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (8.2g, 21.5mmol), Pd(PPh3)4 (0.7g, 0.6mmol), and K2CO3 (8.9g, 64.6mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 5'-(2-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (9.5 g, 16.8 mmol, yield 78%).

[0255]

[0256] Mass : [(M+H) + ] :564

[0257]

[0258] [Synthesization Example 17] Synthesis of 5'-(2-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 303)

[0259]

[0260] 2-(2-bromophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (10.0g, 22.8mmol), 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (8.7g, 22.8mmol), Pd(PPh3)4 (0.8g, 0.7mmol), and K2CO3 (9.5g, 68.4mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 5'-(2-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (10.8 g, 17.6 mmol, yield 77%).

[0261]

[0262] Mass : [(M+H) + ] :614

[0263]

[0264] [Synthesization Example 18] Synthesis of 4'-(2-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 306)

[0265]

[0266] 2-(2-bromophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (10.0g, 22.8mmol), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (8.7g, 22.8mmol), Pd(PPh3)4 (0.8g, 0.7mmol), and K2CO3 (9.5g, 68.4mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 4'-(2-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (10.6 g, 17.3 mmol, yield 76%).

[0267]

[0268] Mass : [(M+H) + ] :614

[0269]

[0270] [Synthesization Example 19] Synthesis of 5'-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 309)

[0271]

[0272] 2-([1,1'-biphenyl]-4-yl)-4-(2-bromophenyl)-6-phenyl-1,3,5-triazine (10.0g, 21.5mmol), 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (8.2g, 21.5mmol), Pd(PPh3)4 (0.7g, 0.6mmol), and K2CO3 (8.9g, 64.6mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 5'-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (10.2g, 15.9mmol, yield 74%).

[0273]

[0274] Mass : [(M+H) + ] :640

[0275]

[0276] [Synthesization Example 20] Synthesis of 4'-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 312)

[0277]

[0278] 2-([1,1'-biphenyl]-4-yl)-4-(2-bromophenyl)-6-phenyl-1,3,5-triazine (10.0g, 21.5mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4'-carbonitrile (8.2g, 21.5mmol), Pd(PPh3)4 (0.7g, 0.6mmol), and K2CO3 (8.9g, 64.6mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 4'-(3-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (10.2g, 15.7mmol, yield 73%).

[0279]

[0280] Mass : [(M+H) + ] :640

[0281]

[0282] [Synthesization Example 21] Synthesis of 5'-(3-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 315)

[0283]

[0284] 2-(3-bromophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (10.0g, 22.8mmol), 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (8.7g, 22.8mmol), Pd(PPh3)4 (0.8g, 0.7mmol), and K2CO3 (9.5g, 68.4mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 5'-(3-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (10.5 g, 17.1 mmol, yield 75%).

[0285]

[0286] Mass : [(M+H) + ] :614

[0287]

[0288] [Synthesization Example 22] Synthesis of 4'-(3-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 318)

[0289]

[0290] 2-(3-bromophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (10.0g, 25.8mmol), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (9.8g, 25.8mmol), Pd(PPh3)4 (0.9g, 0.8mmol), and K2CO3 (10.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 4'-(3-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (11.0 g, 19.6 mmol, yield 76%).

[0291]

[0292] Mass : [(M+H) + ] :564

[0293]

[0294] [Synthesization Example 23] Synthesis of 4'-(3-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 321)

[0295]

[0296] 2-([1,1'-biphenyl]-4-yl)-4-(4-bromophenyl)-6-phenyl-1,3,5-triazine (10.0g, 21.5mmol), 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (8.2g, 21.5mmol), Pd(PPh3)4 (0.7g, 0.6mmol), and K2CO3 (8.9g, 64.6mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 5'-(4-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (10.6 g, 16.6 mmol, yield 77%).

[0297]

[0298] Mass : [(M+H) + ] :640

[0299]

[0300] [Synthesization Example 24] Synthesis of 4'-(4-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 324)

[0301]

[0302] 2-([1,1'-biphenyl]-4-yl)-4-(4-bromophenyl)-6-phenyl-1,3,5-triazine (10.0g, 21.5mmol), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (8.2g, 21.5mmol), Pd(PPh3)4 (0.7g, 0.6mmol), and K2CO3 (8.9g, 64.6mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 4'-(4-(4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (10.5 g, 16.4 mmol, yield 76%).

[0303]

[0304] Mass : [(M+H) + ] :640

[0305]

[0306] [Synthesization Example 25] Synthesis of 5'-(4-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 327)

[0307]

[0308] 2-(4-bromophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (10.0g, 22.8mmol), 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (8.7g, 22.8mmol), Pd(PPh3)4 (0.8g, 0.7mmol), and K2CO3 (9.5g, 68.4mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 5'-(4-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (10.5 g, 17.1 mmol, yield 75%).

[0309]

[0310] Mass : [(M+H) + ] :614

[0311]

[0312] [Synthesization Example 26] Synthesis of 4'-(4-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 330)

[0313]

[0314] 2-(4-bromophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (10.0g, 22.8mmol), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (8.7g, 22.8mmol), Pd(PPh3)4 (0.8g, 0.7mmol), and K2CO3 (9.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 4'-(4-(4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (10.9 g, 17.8 mmol, yield 78%).

[0315]

[0316] Mass : [(M+H) + ] :614

[0317]

[0318] [Synthesization Example 27] Synthesis of 4'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4,4''-dicarbonitrile (Compound 349)

[0319]

[0320] 2-(2-bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.0g, 25.8mmol), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4,4''-dicarbonitrile (10.5g, 25.8mmol), Pd(PPh3)4 (0.9g, 0.8mmol), and K2CO3 (10.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 4'-(2-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4,4''-dicarbonitrile (11.2 g, 19.1 mmol, yield 74%).

[0321]

[0322] Mass : [(M+H) + ] :589

[0323]

[0324] [Synthesization Example 28] Synthesis of 6''-(4,6-diphenyl-1,3,5-triazin-2-yl)-6'-phenyl-[1,1':3',1'':3'',1'''-quaterphenyl]-4-carbonitrile (Compound 356)

[0325]

[0326] 2-(3-bromo-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (10.0g, 25.8mmol), 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (9.8g, 25.8mmol), Pd(PPh3)4 (0.9g, 0.8mmol), and K2CO3 (10.7g, 77.3mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 6''-(4,6-diphenyl-1,3,5-triazin-2-yl)-6'-phenyl-[1,1':3',1'':3'',1'''-quaterphenyl]-4-carbonitrile (11.4g, 20.3mmol, yield 79%).

[0327]

[0328] Mass : [(M+H) + ] :564

[0329]

[0330] [Synthesization Example 29] Synthesis of 4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-3''-phenyl-[1,1':3',1'':4'',1'''-quaterphenyl]-4'''-carbonitrile (Compound 357)

[0331]

[0332] 2-(3-bromo-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (10.0g, 21.5mmol), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (8.2g, 21.5mmol), Pd(PPh3)4 (0.7g, 0.6mmol), and K2CO3 (8.9g, 64.6mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-3''-phenyl-[1,1':3',1'':4'',1'''-quaterphenyl]-4'''-carbonitrile (10.9 g, 17.0 mmol, yield 79%).

[0333]

[0334] Mass : [(M+H) + ] :640

[0335]

[0336] [Synthesization Example 30] Synthesis of 2''-(4,6-diphenyl-1,3,5-triazin-2-yl)-6'-phenyl-[1,1':3',1'':4'',1'''-quaterphenyl]-4-carbonitrile (Compound 368)

[0337]

[0338] 2-(4-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (10.0g, 21.5mmol), 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (8.2g, 21.5mmol), Pd(PPh3)4 (0.7g, 0.6mmol), and K2CO3 (8.9g, 64.6mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 2''-(4,6-diphenyl-1,3,5-triazin-2-yl)-6'-phenyl-[1,1':3',1'':4'',1'''-quaterphenyl]-4-carbonitrile (10.7 g, 16.8 mmol, yield 78%).

[0339]

[0340] Mass : [(M+H) + ] :640

[0341]

[0342] [Synthesization Example 31] Synthesis of 4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-3''-phenyl-[1,1':3',1'':4'',1'''-quaterphenyl]-4'''-carbonitrile (Compound 369)

[0343]

[0344] 2-(3-bromo-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine (10.0g, 21.5mmol), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-3-carbonitrile (8.2g, 21.5mmol), Pd(PPh3)4 (0.7g, 0.6mmol), and K2CO3 (8.9g, 64.6mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 4'-(4,6-diphenyl-1,3,5-triazin-2-yl)-3''-phenyl-[1,1':3',1'':4'',1'''-quaterphenyl]-3'''-carbonitrile (10.6 g, 16.6 mmol, yield 77%).

[0345]

[0346] Mass : [(M+H) + ] :640

[0347]

[0348] [Synthesization Example 32] Synthesis of 5'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 404)

[0349]

[0350] 2-([1,1'-biphenyl]-3-yl)-4-(2-bromophenyl)-6-phenyl-1,3,5-triazine (10.0g, 21.5mmol), 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (8.2g, 21.5mmol), Pd(PPh3)4 (0.7g, 0.6mmol), and K2CO3 (8.9g, 64.6mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 5'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (10.7 g, 16.8 mmol, yield 78%).

[0351]

[0352] Mass : [(M+H) + ] :640

[0353]

[0354] [Synthesization Example 33] Synthesis of 4'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 406)

[0355]

[0356] 2-([1,1'-biphenyl]-3-yl)-4-(2-bromophenyl)-6-phenyl-1,3,5-triazine (10.0g, 21.5mmol), 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (8.2g, 21.5mmol), Pd(PPh3)4 (0.7g, 0.6mmol), and K2CO3 (8.9g, 64.6mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 4'-(2-(4-([1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (10.7 g, 16.8 mmol, yield 78%).

[0357]

[0358] Mass : [(M+H) + ] :640

[0359]

[0360] [Synthesization Example 34] Synthesis of 5'-(2-(4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (Compound 409)

[0361]

[0362] 2-(2-bromophenyl)-4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazine (10.0g, 21.5mmol), 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1''-terphenyl]-4-carbonitrile (8.2g, 21.5mmol), Pd(PPh3)4 (0.7g, 0.6mmol), and K2CO3 (8.9g, 64.6mmol) were added to 150ml of toluene, 22.5ml of ethanol, and 22.5ml of water, and heated and stirred under reflux for 2 hours. After the reaction was completed, the mixture was extracted with Methylene Chloride, the extracted organic layer was dehydrated with Magnesium Sulfate, concentrated, and purified by column chromatography to obtain 5'-(2-(4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazin-2-yl)phenyl)-[1,1':2',1''-terphenyl]-4-carbonitrile (10.2g, 16.8mmol, yield 77%).

[0363]

[0364] Mass : [(M+H) + ] :613

[0365]

[0366] [Example 1] Fabrication of a Blue Organic Electroluminescent Device

[0367] Compound 009 synthesized in Synthesis Example 1 was purified by high-purity sublimation using a commonly known method, and a blue organic electroluminescent device was fabricated as follows.

[0368] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0369] On the ITO transparent electrode prepared as described above, a hole injection layer with a thickness of 100 Å was formed by co-depositing compound A and compound B in a weight ratio of 98:2, and then compound A was deposited on top of the hole injection layer to form a hole transport layer with a thickness of 1400 Å. Subsequently, a hole transport auxiliary layer was formed by depositing compound C with a thickness of 50 Å on top of the hole transport layer, and a emitting layer with a thickness of 200 Å was formed by co-depositing compound D and compound E in a weight ratio of 98:2. Subsequently, an electron transport auxiliary layer with a thickness of 50 Å was formed by depositing compound F on top of the emitting layer, and then an electron transport layer with a thickness of 300 Å was formed by co-depositing compound 001 and compound H in a weight ratio of 1:1. Subsequently, an organic light-emitting diode was fabricated by depositing LiF on the electron transport layer to form an electron injection layer with a thickness of 10 Å, and then depositing Al on the electron injection layer to form a cathode with a thickness of 1000 Å.

[0370] The structures of compounds A to H used at this time are as follows.

[0371]

[0372]

[0373]

[0374] [Examples 2 to 34] Fabrication of Blue Organic Electroluminescent Devices

[0375] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound 009, which was used as the electron transport layer material in Example 1.

[0376]

[0377] [Comparative Examples 1 to 4] Fabrication of Blue Organic Electroluminescent Devices

[0378] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 1, except that compounds I to L were used instead of compound 009 as the electron transport layer material. At this time, the structures of compounds I, J, K, and L are as follows.

[0379]

[0380]

[0381] [Evaluation Example 1]

[0382] For the blue organic electroluminescent devices fabricated in Examples 1 to 31 and Comparative Examples 1 to 4, respectively, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA / cm² were measured, and the results are shown in Table 1 below.

[0383]

[0384] Sample Electron Transport Layer Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 1 Compound 009 3.34548.9 Example 2 Compound 015 3.44528.8 Example 3 Compound 018 3.44538.7 Example 4 Compound 033 3.54528.7 Example 5 Compound 036 3.64528.8 Example 6 Compound 051 3.44548.7 Example 7 Compound 054 3.64538.7 Example 8 Compound 061 3.74528.6 Example 9 Compound 065 3.64548.8 Example 10 Compound 072 3.74538.8 Example 11 Compound 1073.54548.9 Example 12 Compound 1163.84558.7 Example 13 Compound 1873.54528.6 Example 14 Compound 1953.44548.7 Example 15 Compound 2183.64538.8 Example 16 Compound 2973.54548.9 Example 17 Compound 3033.64538.7 Example 18 Compound 3063.44558.7 Example 19 Compound 3093.34538.6 Example 20 Compound 3123.54558.8 Example 21 Compound 3153.74558.8 Example 22 Compound 3183.54528.7 Example 23 Compound 3213.64538.6 Example 24 Compound 3243.84548.7 Example 25 Compound 3273.64558.8 Example 26 Compound 3303.34548.7 Example 27 Compound 3493.44558.9 Example 28 Compound 3563.44538.7 Example 29 Compound 3573.64568.9 Example 30 Compound 3683.54558.6 Example 31 Compound 3693.54528.8 Example 32 Compound 4043.54548.8 Example 33 Compound 4063.64538.9 Example 34 Compound 4093.54548.8 Comparative Example 1 Compound I 4.04558.1 Comparative Example 2 Compound J 4.34547.5 Comparative Example 3 Compound K 4.14557.7 Comparative Example 4 Compound L 4.14547.6

[0385] As shown in Table 1 above, it was found that the blue organic electroluminescent devices of Examples 1 to 34, which used the compounds of the present invention in the electron transport layer, exhibited superior performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic electroluminescent devices of Comparative Examples 1 to 4, which used compounds I to L in the electron transport layer.

[0386] In addition, it was found that the blue organic electroluminescent devices of Examples 1 to 34 exhibited superior performance in terms of driving voltage and current efficiency compared to the blue organic electroluminescent device of Comparative Example 1, which used a compound (e.g., Compound I) in the electron transport layer, in which a triazine and a terphenyl containing a cyano group were bonded as a naphthyl linker, in which an aryl moiety containing a terphenyl based on a triazine ortho-bonded to an arzine group with excellent electron transport capacity and stability were bonded; the blue organic electroluminescent device of Comparative Example 2, in which a compound (e.g., Compound J) in the electron transport layer was bonded to an asymmetric triazine with a cyano group and a terphenyl in an ortho-bonded structure; and the blue organic electroluminescent devices of Comparative Examples 3 and 4, in which a compound (e.g., Compounds K, L) in the electron transport layer was bonded to a triazine and an aryl group that is not a terphenyl containing a cyano group.

[0387]

[0388] [Example 35] Fabrication of a Blue Organic Electroluminescent Device

[0389] Compound 195 synthesized in Synthesis Example 14 was purified by high-purity sublimation using a commonly known method, and a blue organic electroluminescent device was fabricated as follows.

[0390] First, a glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1200 Å was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol and dried, then transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), cleaned with UV light for 5 minutes, and then transferred to a vacuum deposition machine.

[0391] On the ITO transparent electrode prepared as described above, compound A and compound B were co-deposited in a weight ratio of 98:2 to form a hole injection layer with a thickness of 100 Å, and then compound A was deposited on top of the hole injection layer to form a hole transport layer with a thickness of 1400 Å. Subsequently, compound C was deposited to a thickness of 50 Å on top of the hole transport layer to form a hole transport auxiliary layer, and compound D and compound E were co-deposited in a weight ratio of 98:2 to form a emitting layer with a thickness of 200 Å. Subsequently, compound F was deposited on top of the emitting layer to form an electron transport auxiliary layer with a thickness of 50 Å, and then compound G and compound H were co-deposited in a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å. Subsequently, an organic light-emitting diode was fabricated by depositing LiF on the electron transport layer to form an electron injection layer with a thickness of 10 Å, and then depositing Al on the electron injection layer to form a cathode with a thickness of 1000 Å.

[0392] The structures of compounds A, B, C, D, E, F, G, and H used at this time are as follows, respectively.

[0393]

[0394]

[0395]

[0396] [Examples 36 and 37] Fabrication of Blue Organic Electroluminescent Devices

[0397] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 35, except that the compounds listed in Table 2 below were used instead of Compound 195, which was used as the electron transport auxiliary layer material in Example 35.

[0398]

[0399] [Comparative Example 5] Fabrication of a blue organic electroluminescent device

[0400] A blue organic electroluminescent device was fabricated by performing the same procedure as in Example 35, except that compound F was used instead of compound 195 as the electron transport auxiliary layer material.

[0401]

[0402] [Evaluation Example 2]

[0403] For the blue organic electroluminescent devices fabricated in Examples 35 to 37 and Comparative Example 5, respectively, the driving voltage, current efficiency, and emission wavelength at a current density of 10 mA / cm² were measured, and the results are shown in Table 2 below.

[0404]

[0405] Sample Electron Transport Assisted Layer Driving Voltage (V) Luminescence Peak (nm) Current Efficiency (cd / A) Example 35 Compound 1953.74537.8 Example 36 Compound 2183.64557.9 Example 37 Compound 3683.74547.8 Comparative Example 5 Compound F4.44556.8

[0406] As shown in Table 2 above, it was found that the blue organic electroluminescent devices of Examples 35 to 37, which used the compound of the present invention in the electron transport assist layer, exhibited superior performance in terms of driving voltage and current efficiency compared to the blue organic electroluminescent device of Comparative Example 5, which used compound F in the electron transport assist layer.

Claims

Compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X1 to X 14 They are identical or different from each other, and 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 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 It is an aryl group or a heteroaryl group having 5 to 60 nuclei, and X1 to X 14 One of them is bonded to L, and at least one of the remainder not bonded to L is a cyano group, and L is a single bond or C5~C 60 Selected from the group consisting of an arylene group and a heteroarylene group having 5 to 40 nuclei, The above A is selected from the moiety of A-1 to A-4 below, and * represents the part connected to L of the above chemical formula 1, and Y1 to Y 21 They are identical or different from one another, and each independently is CR' or N, wherein Y1 to Y5 comprise 1 to 3 Ns, Y6 and Y7 comprise 1 or 2 Ns, and Y8 to Y 14 It includes 1 to 3 Ns, and Y 15 to Y 21 It includes 1 to 3 Ns. The above R' are identical or different from each other and 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 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 an aryl group, a heteroaryl group having 5 to 60 nuclei, and The above X1 to X 14 C1~C of 40 alkyl group of, C2~C 40 alkenyl group, C2~C 40 alkynyl group, C3~C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 The aryl group of, a heteroaryl group having 5 to 60 nuclei, and the C5~C of the above L 60 The arylene group and the heteroarylene group having 5 to 40 nuclei, and the moiety of A-1 to A-4 of A 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 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 aryl group, heteroaryl group having 5 to 60 nuclei, C1~C 40 alkyloxy group of, C6~C 60 aryloxy group of, C1~C 40 alkylsilyl group of, C6~C 60 arylsilyl group of, C1~C 40 alkylboron group of, C6~C 60 arylboron group of, C6~C 60 arylphosphine group of, C6~C 60 arylphosphine oxide group, C6~C 60 The arylamine group of, C5~C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl heteroarylamine group and a heteroarylamine group having 5 to 60 nuclei. In this case, if there are multiple substituents, they may be identical or different from each other, may combine or condense to form a condensed ring, and 1 to 3 carbons may be substituted with N, O, S, or Se. In paragraph 1, A compound represented by the above chemical formula 1, wherein the compound is represented by any one of the following chemical formulas 2 to 7: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] In the above chemical formulas 2 to 7, X1 to X 14 , L and A are each as defined in Paragraph 1. In paragraph 1, A compound in which L of Chemical Formula 1 is any one selected from the following structural formulas: * represents X1 to X of the above chemical formula 1. 14 It refers to the part connected to any one of them, and A is as defined in Paragraph 1. In paragraph 1, The above A is a compound selected from any one of the following moiety: * indicates a region connected to Chemical Formula 1, and the above moiety is 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 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclei, C6~C 60 It can be substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclei. In paragraph 1, Compound represented by the above chemical formula 1 is selected from the group consisting of the following compounds 001 to 416: Anode; cathode; and one or more organic layers interposed between the anode and the cathode, comprising An organic electroluminescent device comprising at least one of the above one or more organic layers, wherein the organic compound described in any one of claims 1 to 5. In paragraph 6, An organic electroluminescent device in which the organic layer containing the above organic compound is an electron transport layer or an electron transport auxiliary layer.

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