Organic light-emitting compound and organic electroluminescent device containing the same

Abstract

The present invention relates to a novel compound having excellent carrier transport ability, light emitting ability, and thermal stability, and to an organic electroluminescence device having improved properties such as light emitting efficiency, driving voltage, and life span by incorporating the compound in one or more organic layers.

Description

[Technical field]

[0001] The present invention relates to a novel organic compound and an organic electroluminescence device using the same, and more particularly to a novel compound having excellent carrier transport ability, light emitting ability, and heat resistance, and an organic electroluminescence device including the compound in one or more organic layers, thereby improving properties such as light emitting efficiency, driving voltage, and life span. [Background technology]

[0002] Since the discovery of organic thin film luminescence by Bernanose in the 1950s, research on organic electroluminescent elements, which led to blue electric luminescence using anthracene single crystals in 1965, led to the presentation of an organic electroluminescent element with a layered structure consisting of functional layers of a hole layer and an emission layer by Tang in 1987. Since then, in order to obtain organic electroluminescent elements with high efficiency and long life, developments have been made to contain each of the characteristic organic layers within the element, which led to the development of special materials to achieve this.

[0003] In an organic electroluminescence element, when a voltage is applied between the two electrodes, holes are injected from the positive electrode and electrons are injected from the negative electrode into the organic layer. When the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons return to the ground state. At this time, the materials used in the organic layer are classified according to their functions into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc.

[0004] The light-emitting layer materials of organic electroluminescence devices can be classified into blue, green, and red light-emitting materials according to the light-emitting color. Furthermore, yellow and orange light-emitting materials are also used as light-emitting materials to realize better natural colors. In addition, host / dopant systems are used as light-emitting materials to improve color purity and improve light-emitting efficiency by energy transfer. The dopant materials are broadly classified into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. Such phosphorescent materials can theoretically improve the light-emitting efficiency by four times compared to fluorescence, so interest is focused not only on phosphorescent dopants but also on phosphorescent host materials. Currently, materials used for the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer include NPB, BCP, Alq 3 As for luminescent materials, anthracene derivatives have been reported as fluorescent dopant / host materials. In particular, phosphorescent materials that have a great advantage in terms of improving efficiency include Firpic and Ir(ppy). 3 , (acac)Ir(btp) 2 Metal complex compounds containing Ir, such as the above, are used as blue, green, and red dopant materials. Currently, CBP shows excellent properties as a phosphorescent host material.

[0005] However, although conventional luminescent materials have advantages in terms of luminescent properties, they have low glass transition temperatures and poor thermal stability, resulting in an unsatisfactory life span in organic electroluminescent devices. Therefore, there is a demand for the development of luminescent materials with superior performance.

[0006] Deuterium has a natural abundance of about 0.015%. Deuterium compounds with high deuterium concentrations are well known. Deuterated aromatic compounds have been used to study chemical reactions and metabolic pathways, and as raw materials for pharmaceuticals, agrochemicals, functional materials, and analytical tracers. Some deuterated electroluminescent materials have been reported to have improved performance (efficiency, lifetime) compared to non-deuterated isotopic isomers. See, for example, Tong, et al., J.Phys.Chem.C 2007,111,3490-4). Currently, methods for synthesizing deuterated compounds may require a self-weighting process to achieve a high level of deuteration. Such methods are not suitable in terms of cost and efficiency because of their high cost or time. Therefore, there is a need for improved manufacturing methods for synthesizing deuterated aromatic compounds. Summary of the Invention [Problem to be solved by the invention]

[0007] The present invention has been devised to solve the above-mentioned problems, and an object of the present invention is to provide a novel compound which has excellent carrier transport ability, light emitting ability, heat resistance, etc. and can be used as an organic layer material of an organic electroluminescence element, specifically, as a host material for the light emitting layer.

[0008] Another object of the present invention is to provide an organic electroluminescence device that contains the above-mentioned novel compound and thus has a low driving voltage, high luminous efficiency and improved life span.

[0009] Other objects and advantages of the present invention will become more apparent from the following detailed description and claims. [Means for solving the problem]

[0010] In order to achieve the above technical objectives, the present invention provides a compound represented by the following [Chemical Formula 1], specifically, a deuterated triscarbazole compound. [ka] (In the above formula, Ar 1 and Ar 2 are the same or different, and each independently represents C 1 ~C 40 Alkyl groups of C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 6 ~C 40 aryl groups, heteroaryl groups having 5 to 40 ring atoms, C 6 ~C 40 Aryloxy groups, C 1 ~C 40 Alkyloxy groups, C 6 ~C 40 Arylamine groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 1 ~C 40 Alkylsilyl group, C 1 ~C 40 Alkylboron group, C 6 ~C 40 Arylboron groups, C 6 ~C 40 Arylphosphine groups, C 6 ~C 40 and C 6 ~C 40 and wherein the arylsilyl group is selected from the group consisting of a, d, and f each independently represent 1 to 3; b, c, and e each independently represent 1 to 4, provided that a+b+c+d+e+f≧15; The hydrogen in the benzene ring of carbazole, which is unsubstituted with deuterium (D), is C 1 ~C 40 Alkyl groups of C 6 ~C 40 and a heteroaryl group having 5 to 40 ring atoms, The above Ar 1 ~Ar 2 The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylsilyl group each independently include deuterium (D), halogen, cyano group, nitro group, C 1 ~C 40 Alkyl groups of C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 6 ~C 40 aryl groups, heteroaryl groups having 5 to 40 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy groups, C 1 ~C 40 Alkylsilyl group, C 6 ~C 40 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C 40 Arylboron groups, C 6 ~C 40 Arylphosphine groups, C 6 ~C 40 and C 6 ~C 40 and when there are a plurality of the above-mentioned substituents, they may be the same or different from each other.)

[0011] The present invention also provides an organic electroluminescence device comprising a positive electrode, a negative electrode, and one or more organic layers interposed between the positive electrode and the negative electrode, wherein at least one of the one or more organic layers contains a compound represented by the above [Chemical Formula 1].

[0012] In one embodiment, the one or more organic layers include at least one selected from the group consisting of an emitting layer, an emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and an electron transport auxiliary layer, and the emitting layer may include the compound represented by the above [Chemical Formula 1] as a host.

[0013] In one embodiment, the electron transport layer can include an electron transport compound containing at least two electron withdrawing groups (EWGs). Effect of the Invention

[0014] In one embodiment of the present invention, the compound represented by the above [Chemical Formula 1] has excellent carrier transport ability, light emitting ability, and heat resistance, and therefore can be used as an organic layer material of an organic electroluminescence device.

[0015] In particular, when the compound represented by [Chemical Formula 1] of the present invention is used as a host material in the light-emitting layer, higher thermal stability, lower driving voltage, higher mobility, higher current efficiency, and longer life characteristics can be obtained compared to conventional host materials.

[0016] Therefore, the organic electroluminescence device including the compound represented by the above [Chemical Formula 1] has excellent light-emitting performance, low driving voltage, long life, and high efficiency, and can be effectively applied to full-color display panels, etc.

[0017] The effects of the present invention are not limited to the above-mentioned contents, and more various effects are included in the present specification. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0018] The present invention will be described in detail below.

[0019] <Organic compounds> The present invention provides a novel electroluminescent material that contains at least three carbazole groups (Cz), and improves the carrier transport ability, light emitting ability, and stability of the chemical structure by substituting deuterium (D) in such carbazole groups, thereby simultaneously achieving device characteristics such as low voltage, high efficiency, and long life characteristics of the device.

[0020] Specifically, the compound represented by [Chemical Formula 1] of the present invention has a basic structure that contains at least three carbazole groups (Cz) as an essential component and at least 15 deuteriums (D) substituted on the carbazole groups. This compound is a new P-type host composed of triscarbazole, and has higher hole character than existing host materials, making it possible to maximize the performance of the N-type host. In addition, since the hole stability is improved compared to existing P-type host materials, the device can continue to maintain stable life characteristics even in the initial characteristics. Therefore, when a P-type host composed of at least three carbazole groups is provided, the hole stability of the device itself is increased, making it possible to manufacture a high-performance OLED device.

[0021] From the viewpoint of potential energy, deuterium (D) has a higher molecular mass and a lower zero-point energy than hydrogen (H), so that deuterium is relatively difficult to dissociate during a reaction. This low zero-point energy increases the bond dissociation energy and reduces reactivity, which increases the stability of molecules containing deuterium (Molecules 2014, 19 Chem.Commun.2014, 50, 14870-14872 J.Org.Chem.2004, 69, 7212-7219). Thus, according to the compound represented by [Chemical Formula 1] of the present invention, which contains at least three carbazole groups and has at least 15 or more deuteriums (D) substituted thereon, the green color purity is maximized compared to a compound having the same structure but without deuterium, and the weakened intramolecular bond between carbon and hydrogen is strengthened, improving the stability of the material and significantly improving the life characteristics of the element.

[0022] In addition, in the present invention, by forming an emission layer containing the compound represented by the above [Chemical Formula 1] and using a dual EWG type electron transport layer containing at least two EWG groups and having high electron transport ability in combination, it is possible to improve the hole stability of the emission layer (EML) and maximize the electron transport ability of the electron transport layer (ETL), thereby optimizing the performance of the organic electroluminescence device.

[0023] Specifically, the compound represented by [Chemical Formula 1] of the present invention has a basic skeleton structure that essentially contains at least three carbazole groups (Cz) and contains at least 15 deuteriums (D) substituted by such carbazole groups. As an example, the number of deuteriums (D) contained in the basic skeleton structure is 15 or more, specifically, a, d, and f in [Chemical Formula 1] are each independently 1 to 3, and b, c, and e are each independently 1 to 4, with the proviso that a+b+c+d+e+f≧15. Preferably, a=d=f=3, b=c=e=4 in the above [Chemical Formula 1], and the number of deuteriums (D) is 21 or more.

[0024] In this case, the hydrogen atoms in the benzene ring of the carbazole group that is not substituted with a deuterium (D) are each independently C 1 ~C 40 Alkyl groups of C 6 ~C 40 and heteroaryl groups having 5 to 40 ring atoms.

[0025] In the above [chemical formula 1], among at least three carbazole groups (Cz), the N-positions of the two carbazole groups located at both ends have various substituents such as Ar 1 and Ar 2 This Ar may be introduced. 1 and Ar 2 may be the same or different, and each independently represents C 1 ~C 40 Alkyl groups of C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 6 ~C 40 aryl groups, heteroaryl groups having 5 to 40 ring atoms, C 6 ~C 40 Aryloxy groups, C 1 ~C 40 Alkyloxy groups, C 6 ~C 40 Arylamine groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 1 ~C 40 Alkylsilyl group, C 1 ~C 40 Alkylboron group, C 6 ~C 40 Arylboron groups, C 6 ~C 40 Arylphosphine groups, C 6 ~C 40 and C 6 ~C 40 Specifically, the arylsilyl group may be selected from the group consisting of Ar 1 and Ar2 may be the same or different, and each independently represents C 6 ~C 40 and heteroaryl groups having 5 to 40 ring atoms. More specifically, Ar 1 and Ar 2 are each independently 6 ~C 40 is an aryl group represented by the formula Ar 1 and Ar 2 The aryl groups are each independently deuterium (D), 6 ~C 40 and heteroaryl groups having 5 to 40 ring atoms, and when there are a plurality of the above-mentioned substituents, they may be the same or different. 1 and Ar 2 The aryl group may be unsubstituted with deuterium (D) or partially substituted with at least one deuterium (D), provided that Ar 1 and Ar 2 It is also possible to exclude any of the aryl groups being substituted with deuterium (D).

[0026] In particular, in order to confirm the deuteration effect, it is preferable that the compound represented by the above [Chemical Formula 1] has a deuterium ratio of at least 67%, and there is no particular upper limit.

[0027] In one embodiment, Ar 1 and Ar 2 may be the same or different and each independently may be any one selected from the group consisting of the following substituents S1 to S9, but is not limited thereto. [ka] In the above formula, * is a bonding site with the above [Chemical Formula 1]. Although not shown in the above structural formula, at least one deuterium (D) may be substituted. In addition, a substituent known in the art (for example, R 1 The definition of is the same as that of the above. At least one ) may be substituted.

[0028] In the above [chemical formula 1], the Ar 1 ~Ar 2 The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylsilyl group each independently include deuterium (D), halogen, cyano group, nitro group, C 1 ~C 40 Alkyl groups of C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 6 ~C 40 aryl groups, heteroaryl groups having 5 to 40 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy groups, C 1 ~C 40 Alkylsilyl group, C 6 ~C 40 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C 40 Arylboron groups, C 6 ~C 40 Arylphosphine groups, C 6 ~C 40 and C 6 ~C 40and when there are a plurality of the above-mentioned substituents, they may be the same or different.

[0029] In one embodiment of the present invention, the compound represented by the above [Chemical Formula 1] may be embodied as any one of the following [Chemical Formula 2] to [Chemical Formula 17] depending on the bonding positions between at least three carbazole groups. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] In the above formula, Ar 1 , Ar 2 , a, b, c, d, e, and f are as defined above in [Chemical Formula 1].

[0030] In the present invention, the compounds represented by [Chemical Formula 2] to [Chemical Formula 17] are triscarbazole-type materials in which one carbazole is added to an existing biscarbazole, and the additional carbazole bonded can maximize the hole stability more than the existing biscarbazole-type materials. This contributes to optimizing the device performance. In addition, the thermal stability of the material itself can be maximized by deuterizing the main skeleton of the material. All of the compounds represented by [Chemical Formula 2] to [Chemical Formula 17] above can obtain the effect of improving the hole stability described above, but among them, the compounds represented by [Chemical Formula 6] to [Chemical Formula 9] are preferably used to obtain structurally more excellent hole stability. More preferably, at least three carbazole groups are bonded, but the compound represented by [Chemical Formula 8] bonded to the 3-position, which is the active site of the carbazole group, may be used.

[0031] The compound represented by [Chemical Formula 1] according to the present invention as described above can be embodied as any one of the following compounds A-1 to U-1. However, the compound represented by [Chemical Formula 1] according to the present invention is not limited to these examples.

[0032] [ka] [ka] [ka] [ka]

[0033] In the present invention, "alkyl" refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

[0034] In the present invention, "alkenyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon double bonds. Examples of this include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, etc.

[0035] In the present invention, "alkynyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon triple bonds. Examples of this include, but are not limited to, ethynyl, 2-propynyl, etc.

[0036] 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 thereof include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

[0037] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 ring atoms, in which one or more carbons, preferably 1 to 3 carbons, in the ring are substituted with a heteroatom such as N, O, S or Se. Examples include, but are not limited to, morpholine, piperazine, etc.

[0038] In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. The two or more rings may be in a pendant or condensed form. Examples of such groups include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0039] In the present invention, "heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 ring atoms. In this case, one or more carbons, preferably 1 to 3 carbons, in the ring are substituted with a heteroatom such as N, O, S or Se. In addition, two or more rings may be in a pendant or condensed form, and further in a condensed form with an aryl group. Examples of this include, but are not limited to, 6-membered monocyclic rings such as pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.

[0040] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' is an alkyl group having 1 to 40 carbon atoms. Such alkyloxy may have 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.

[0041] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, where R means an aryl having 6 to 60 carbon atoms. Examples of this include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

[0042] In the present invention, the term "alkylsilyl" refers to a silyl substituted with an alkyl having 1 to 40 carbon atoms, and the term "arylsilyl" refers to a silyl substituted with an aryl having 6 to 60 carbon atoms.

[0043] In the present invention, the term "alkylboron" refers to boron substituted with an alkyl group having 1 to 40 carbon atoms, and the term "arylboron" refers to boron substituted with an aryl group having 6 to 60 carbon atoms.

[0044] In the present invention, the term "arylphosphine" refers to a phosphine substituted with an aryl having 6 to 60 carbon atoms, and the term "arylphosphine oxide group" refers to a phosphine substituted with an aryl having 6 to 60 carbon atoms that contains O.

[0045] In the present invention, the term "fused ring" means a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

[0046] In the present invention, the term "arylamine" refers to an amine substituted with an aryl having 6 to 60 carbon atoms.

[0047] The compound represented by the formula 1 of the present invention can be produced according to a conventional method in the art without any restrictions. For example, it can be synthesized in various ways based on the synthesis process in the examples described later.

[0048] <Organic electroluminescence element> The present invention provides an organic electroluminescence device comprising the compound represented by the above [Chemical Formula 1].

[0049] Specifically, the organic electroluminescence device according to the present invention comprises a positive electrode (anode), a negative electrode (cathode), and one or more organic layers interposed between the positive electrode and the negative electrode, and at least one of the one or more organic layers comprises the compound represented by the above [Chemical Formula 1].

[0050] The one or more organic layers include at least one 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, an electron transport layer, and an electron transport auxiliary layer, and at least one of these organic layers includes a compound represented by the above [Chemical Formula 1]. More specifically, the organic layer including the compound represented by the above [Chemical Formula 1] is a light-emitting layer, and in this case, the compound of the above [Chemical Formula 1] is included as a host material.

[0051] Such an emission layer contains a host material and / or a dopant material, and in this case, the compound of [Chemical Formula 1] above can be used as a P-type host material. The emission layer can further contain at least one of a general P-type host and an N-type host known in the art, in addition to the host material of [Chemical Formula 1] above. Also, it may further contain a dopant known in the art without any restrictions. The content ratio (mixing ratio) of these is not particularly limited and can be appropriately adjusted within the range of the content known in the art. As an example, the emission layer can contain 70 to 99.9 parts by weight of a host and 0.1 to 30 parts by weight of a dopant based on the total weight of the emission layer.

[0052] The dopant contained in the light-emitting layer is not particularly limited as long as it is known in the art, and may include at least one of a fluorescent dopant and a phosphorescent dopant, for example. Usable dopants include, but are not limited to, anthracene derivatives, pyrene derivatives, arylamine derivatives, metal complex compounds containing iridium (Ir) or platinum (Pt), etc. Such dopants are classified into red dopants, green dopants, and blue dopants, and any red dopants, green dopants, and blue dopants known in the art may be used without any particular limitation.

[0053] The organic electroluminescence device according to the present invention may include both an emission layer (EML) containing the compound of [Chemical Formula 1] as a host and a dual EWG type electron transport layer (ETL) containing at least two EWG groups and having high electron transport ability. In this case, the performance of the organic electroluminescence device can be optimized by improving the hole stability of the emission layer (EML) and maximizing the electron transport ability of the electron transport layer (ETL).

[0054] The electron transport layer is not particularly limited as long as it is a compound containing at least two EWG groups (electron-withdrawing groups), and specific examples thereof include compounds represented by the following [chemical formula 18].

[0055] [ka] (In the above formula, L is for C 6 ~C 40 and heteroarylene groups having 5 to 40 ring atoms, X 1 ~X 10 are each independently N or (CR 1 ) and Above C(R 1 ) is multiple, multiple R 1 are the same or different, and each independently represents C 1~C 40 Alkyl groups of C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 6 ~C 40 aryl groups, heteroaryl groups having 5 to 40 ring atoms, C 6 ~C 40 Aryloxy groups, C 1 ~C 40 Alkyloxy groups, C 6 ~C 40 Arylamine groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 1 ~C 40 Alkylsilyl group, C 1 ~C 40 Alkylboron group, C 6 ~C 40 Arylboron groups, C 6 ~C 40 Arylphosphine groups, C 6 ~C 40 and C 6 ~C 40 and wherein the arylsilyl group is selected from the group consisting of The arylene group and heteroarylene group of L and the R 1 The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylsilyl group each independently include deuterium (D), halogen, cyano group, nitro group, C 1 ~C 40 Alkyl groups of C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 6 ~C60 aryl groups, heteroaryl groups having 5 to 60 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy groups, C 1 ~C 40 Alkylsilyl group, C 6 ~C 60 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C 60 Arylboron groups, C 6 ~C 60 Arylphosphine groups, C 6 ~C 60 and C 6 ~C 60 and when there are a plurality of the above-mentioned substituents, they may be the same or different.)

[0056] In the above [chemical formula 18], X 1 ~X 5 Ring containing and X 6 ~X 10 Each of the ring-containing rings is included as an EWG group. 1 ~X 5 Ring containing and X 6 ~X 10 The ring-containing groups may be the same or different and can each independently be embodied as any one selected from the group consisting of the following substituents A-1 to A-5.

[0057] [ka] (In the above formula, * indicates the bonding site with the above [Chemical Formula 18]. Z 1 and Z 2 may be the same or different, and each independently represents C 6 ~C 40and heteroaryl groups having 5 to 40 ring atoms, R 1 are each independently hydrogen, C 1 ~C 40 Alkyl groups of C 6 ~C 40 and heteroaryl groups having 5 to 40 ring atoms, Above Z 1 ~Z 2 The aryl and heteroaryl groups of the above R 1 The alkyl group, aryl group, and heteroaryl group each independently include deuterium (D), halogen, cyano group, C 6 ~C 40 and heteroaryl groups having 5 to 40 ring atoms, and in this case, when there are a plurality of the above-mentioned substituents, they may be the same or different.)

[0058] In one embodiment, Z 1 and Z 2 may be the same or different, and each independently may be embodied as any one selected from the following structural formulas: [ka]

[0059] The two EWG groups are linked via a linker (L). Such a linker is a typical divalent group linker known in the art, specifically, 6 ~C 25 and heteroarylene groups having 5 to 18 ring atoms.

[0060] In one embodiment, L can be embodied as a linker selected from, but not limited to, the following structural formulas: [ka] In the above formula, * is a bonding site with the above [Chemical Formula 18]. Although not shown in the above structural formula, a substituent known in the art (e.g., R 1 The definition of is the same as that of .) may be replaced by at least one.

[0061] The structure of the organic electroluminescence element of the present invention having the above-mentioned configuration is not particularly limited, and can have a structure known in the art.For example, it can 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, an electron injection layer, and a negative electrode are sequentially stacked.The structure of the organic electroluminescence element according to 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.

[0062] The organic electroluminescence device according to the present invention can be manufactured by forming the organic layers and electrodes using materials and methods known in the art, except that at least one of the organic layers contains the compound represented by the above [Chemical Formula 1].

[0063] The organic layer can be formed by a vacuum deposition method or a solution coating method, such as, but not limited to, a spin coating method, a deep coating method, a doctor flame method, an inkjet printing method, or a thermal transfer method.

[0064] The substrate used in the production of the organic electroluminescence element according to the present invention is not particularly limited, and examples thereof include a silicon wafer, quartz, a glass plate, a metal plate, and a plastic film or sheet.

[0065] The positive electrode material may be a metal such as vanadium, chromium, copper, zinc, or gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); ZnO:Al, or SnO 2Examples of suitable conductive materials include, but are not limited to: a combination of a metal such as Sb with an oxide; a conductive polymer such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiopene] (PEDT), polypyrrole, or polyaniline; and carbon black.

[0066] In addition, the negative electrode material may be a metal or an alloy thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead; and LiF / Al or LiO 2 Examples of the material include, but are not limited to, those having a multi-layer structure such as / Al.

[0067] The hole injection layer, the hole transport layer, and the electron injection layer are not particularly limited, and any material known in the art can be used. EXAMPLES

[0068] The present invention will be described in detail below with reference to examples. However, the examples described below are merely illustrative of the present invention, and the present invention is not limited to these examples.

[0069] <Preparation Example 1> Synthesis of Cz-D1 [ka] Under a nitrogen stream, 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (134.3 g, 530.6 mmol), iodobenzene (130.0 g, 636.7 mmol), Cu (16.8 g, 265.3 mmol), and K 2 CO 3 (146.7 g, 1,061.3 mmol) and toluene (1000 ml) were mixed and stirred at 110° C. for 12 hours.

[0070] After the reaction was completed, the mixture was extracted with ethyl acetate and then cooled to 100° C. 4The water was removed by filtration and the residue was purified by column chromatography (hexane:EA=5:1 (v / v)) to obtain Cz-D1 (125.7 g, yield 72%). Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0071] <Preparation Example 1-2> Synthesis of Cz-D2 [ka] The target compound Cz-D2 (135.5 g, 63% yield) was obtained in the same manner as in Preparation Example 1-1 above, except that 4-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0072] <Preparation Example 1-3> Synthesis of Cz-D3 [ka] The target compound Cz-D3 (148.4 g, 69% yield) was obtained in the same manner as in Preparation Example 1-1 above, except that 3-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0073] <Preparation Example 1-4> Synthesis of Cz-D4 [ka] The target compound Cz-D4 (96.8 g, 45% yield) was obtained in the same manner as in Preparation Example 1-1 above, except that 2-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0074] <Preparation Example 2-1> Synthesis of Cz-D5 [ka] The target compound Cz-D5 (117.1 g, yield 67%) was obtained in the same manner as in Preparation Example 1-1 above, except that 4-bromo-9H-carbazole-1,2,3,5,6,7,8-d7 (134.3 g, 530.6 mmol) was used instead of 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7. Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0075] <Preparation Example 2-2> Synthesis of Cz-D6 [ka] The target compound Cz-D6 (139.8 g, 65% yield) was obtained in the same manner as in Preparation Example 2-1 above, except that 4-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0076] <Preparation Example 2-3> Synthesis of Cz-D7 [ka] The target compound Cz-D7 (152.7 g, 71% yield) was obtained in the same manner as in Preparation Example 2-1 above, except that 3-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0077] <Preparation Example 2-4> Synthesis of Cz-D8 [ka] The target compound Cz-D8 (75.2 g, 35% yield) was obtained in the same manner as in Preparation Example 2-1 above, except that 2-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0078] <Preparation Example 3-1> Synthesis of Cz-D9 [ka] The target compound Cz-D9 (134.5 g, 77% yield) was obtained in the same manner as in Preparation Example 1-1 above, except that 2-bromo-9H-carbazole-1,3,4,5,6,7,8-d7 (134.3 g, 530.6 mmol) was used instead of 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7. Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0079] <Preparation Example 3-2> Synthesis of Cz-D10 [ka] The target compound Cz-D10 (159.1 g, 74% yield) was obtained in the same manner as in Preparation Example 3-1 above, except that 4-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0080] <Preparation Example 3-3> Synthesis of Cz-D11 [ka] The target compound Cz-D11 (163.4 g, 76% yield) was obtained in the same manner as in Preparation Example 3-1 above, except that 3-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0081] <Preparation Example 3-4> Synthesis of Cz-D12 [ka] The target compound Cz-D12 (92.4 g, 43% yield) was obtained in the same manner as in Preparation Example 3-1 above, except that 2-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0082] <Preparation Example 4-1> Synthesis of Cz-D13 [ka] The target compound Cz-D13 (94.3 g, 54% yield) was obtained in the same manner as in Preparation Example 1-1 above, except that 1-bromo-9H-carbazole-2,3,4,5,6,7,8-d7 (134.3 g, 530.6 mmol) was used instead of 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7. Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0083] <Preparation Example 4-2> Synthesis of Cz-D14 [ka] The target compound Cz-D14 (122.6 g, 57% yield) was obtained in the same manner as in Preparation Example 4-1 above, except that 4-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0084] <Preparation Example 4-3> Synthesis of Cz-D15 [ka] The target compound Cz-D15 (111.8 g, 52% yield) was obtained in the same manner as in Preparation Example 4-1 above, except that 3-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0085] <Preparation Example 4-4> Synthesis of Cz-D16 [ka] The target compound Cz-D16 (68.8 g, 32% yield) was obtained in the same manner as in Preparation Example 4-1 above, except that 2-iodo-1,1'-biphenyl (178.3 g, 636.7 mmol) was used instead of iodobenzene. Mass (theoretical value: 405.35, measured value: 405g / mol)

[0086] <Preparation Example 5-1> Synthesis of BCz-D1 <Step 5-1-1> Synthesis of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 [ka] Under a nitrogen stream, Cz-D1 (100.0 g, 303.7 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (84.8 g, 334.1 mmol), and Pd(dppf)Cl 2 (26.6 g, 30.3 mmol), KOAc (85.8 g, 911.1 mmol), and 1,4-dioxane (1000 ml) were mixed and stirred at 130° C. for 12 hours.

[0087] After the reaction was completed, the mixture was extracted with ethyl acetate and then cooled to 100° C. 4 The water was removed by filtration and the residue was purified by column chromatography (hexane:EA=8:1 (v / v)) to obtain 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 (96.0 g, yield 84%). Mass (theoretical value: 376.3, measured value: 376 g / mol)

[0088] <Preparation Example 5-1-2> Synthesis of BCz-D1 [ka] Under a nitrogen stream, 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 (96.0 g, 255.1 mmol), 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (77.5 g, 306.1 mmol), Pd(PPh 3 ) 4 (14.7g, 12.7mmol), K 2 CO 3 (88.1 g, 637.8 mmol), and 1,4-dioxane / H 2 O (1000 ml / 250 ml) was mixed and stirred at 120° C. for 4 hours.

[0089] After the reaction was completed, the mixture was extracted with methylene chloride and then washed with MgSO 4 After removing the solvent from the obtained organic layer, the residue was purified by column chromatography (hexane:EA=7:1 (v / v)) to obtain BCz-D1 (71.1 g, yield 66%). Mass (theoretical value: 422.59, measured value: 422 g / mol)

[0090] <Preparation Example 5-2> Synthesis of BCz-D2 [ka] The target compound BCz-D2 (66.4 g, final yield 54.0%) was obtained in the same manner as in Preparation Example 5-1 above, except that Cz-D2 (100 g, 246.7 mmol) was used instead of Cz-D1. Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0091] <Preparation Example 5-3> Synthesis of BCz-D3 [ka] The target compound BCz-D3 (59.7 g, final yield 48.5%) was obtained in the same manner as in Preparation Example 5-1 above, except that Cz-D3 (100 g, 246.7 mmol) was used instead of Cz-D1. Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0092] <Preparation Example 5-4> Synthesis of BCz-D4 [ka] The target compound BCz-D4 (59.7 g, final yield 48.3%) was obtained in the same manner as in Preparation Example 5-1 above, except that Cz-D4 (100 g, 246.7 mmol) was used instead of Cz-D1. Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0093] <Preparation Example 6-1> Synthesis of BCz-D5 <Step 6-1-1> Synthesis of 9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,3,5,6,7,8-d7 [ka] Under a nitrogen stream, Cz-D5 (100.0 g, 303.7 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (84.8 g, 334.1 mmol), and Pd(dppf)Cl 2 (26.6 g, 30.3 mmol), KOAc (85.8 g, 911.1 mmol), and 1,4-dioxane (1000 ml) were mixed and stirred at 130° C. for 12 hours.

[0094] After the reaction was completed, the mixture was extracted with ethyl acetate and then cooled to 100° C. 4The water was removed by filtration and the residue was purified by column chromatography (hexane:EA=8:1 (v / v)) to obtain 9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,3,5,6,7,8-d7 (74.3 g, yield 65%). Mass (theoretical value: 376.3, measured value: 376 g / mol)

[0095] <Preparation Example 6-1-2> Synthesis of BCz-D5 [ka] Under a nitrogen stream, 9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,3,5,6,7,8-d7 (74.3 g, 197.4 mmol), 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (60.0 g, 236.9 mmol), Pd(PPh 3 ) 4 (11.4g, 9.9mmol), K 2 CO 3 (68.2 g, 493.5 mmol), and 1,4-dioxane / H 2 O (1000 ml / 250 ml) was mixed and stirred at 120° C. for 4 hours.

[0096] After the reaction was completed, the mixture was extracted with methylene chloride and then washed with MgSO 4 After removing the solvent from the obtained organic layer, the residue was purified by column chromatography (hexane:EA=7:1 (v / v)) to obtain BCz-D5 (63.4 g, yield 76%). Mass (theoretical value: 422.59, measured value: 422 g / mol)

[0097] <Preparation Example 6-2> Synthesis of BCz-D6 [ka] The target compound BCz-D6 (55.4 g, final yield 45.1%) was obtained in the same manner as in Preparation Example 6-1 above, except that Cz-D6 (100 g, 246.7 mmol) was used instead of Cz-D5. Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0098] <Preparation Example 6-3> Synthesis of BCz-D7 [ka] The target compound BCz-D7 (43.1 g, final yield 35.1%) was obtained in the same manner as in Preparation Example 6-1 above, except that Cz-D7 (100 g, 246.7 mmol) was used instead of Cz-D5. Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0099] <Preparation Example 6-4> Synthesis of BCz-D8 [ka] The target compound BCz-D8 (28.2 g, final yield 22.9%) was obtained in the same manner as in Preparation Example 6-1 above, except that Cz-D8 (100 g, 246.7 mmol) was used instead of Cz-D5. Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0100] <Preparation Example 7-1> Synthesis of BCz-D9 <Step 7-1-1> Synthesis of 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,3,4,5,6,7,8-d7 [ka] Under a nitrogen stream, Cz-D9 (100.0 g, 303.7 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (84.8 g, 334.1 mmol), and Pd(dppf)Cl 2(26.6 g, 30.3 mmol), KOAc (85.8 g, 911.1 mmol), and 1,4-dioxane (1000 ml) were mixed and stirred at 130° C. for 12 hours.

[0101] After the reaction was completed, the mixture was extracted with ethyl acetate and then cooled to 100° C. 4 The water was removed by filtration and the residue was purified by column chromatography (hexane:EA=8:1 (v / v)) to obtain 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,3,4,5,6,7,8-d7 (81.1 g, yield 71%). Mass (theoretical value: 376.3, measured value: 376 g / mol)

[0102] <Preparation Example 7-1-2> Synthesis of BCz-D9 [ka] Under a nitrogen stream, 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,3,4,5,6,7,8-d7 (81.1 g, 215.6 mmol), 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (65.5 g, 258.8 mmol), Pd(PPh 3 ) 4 (12.5g, 10.8mmol), K 2 CO 3 (74.5 g, 539.1 mmol), and 1,4-dioxane / H 2 O (1000 ml / 250 ml) was mixed and stirred at 120° C. for 4 hours.

[0103] After the reaction was completed, the mixture was extracted with methylene chloride and then washed with MgSO 4 After removing the solvent from the obtained organic layer, the residue was purified by column chromatography (hexane:EA=7:1 (v / v)) to obtain BCz-D9 (67.4 g, yield 74%). Mass (theoretical value: 422.59, measured value: 422 g / mol)

[0104] <Preparation Example 7-2> Synthesis of BCz-D10 [ka] The target compound BCz-D10 (65.2 g, final yield 53.0%) was obtained in the same manner as in Preparation Example 7-1 above, except that Cz-D10 (100 g, 246.7 mmol) was used instead of Cz-D9. Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0105] <Preparation Example 7-3> Synthesis of BCz-D11 [ka] The target compound BCz-D11 (68.2 g, final yield 55.4%) was obtained in the same manner as in Preparation Example 7-1 above, except that Cz-D11 (100 g, 246.7 mmol) was used instead of Cz-D9. Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0106] <Preparation Example 7-4> Synthesis of BCz-D12 [ka] The target compound BCz-D12 (51.1 g, final yield 41.6%) was obtained in the same manner as in Preparation Example 7-1 above, except that Cz-D12 (100 g, 246.7 mmol) was used instead of Cz-D9. Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0107] <Preparation Example 8-1> Synthesis of BCz-D13 <Step 8-1-1> Synthesis of 9-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-2,3,4,5,6,7,8-d7 [ka] Under a nitrogen stream, Cz-D9 (100.0 g, 303.7 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (84.8 g, 334.1 mmol), and Pd(dppf)Cl 2 (26.6 g, 30.3 mmol), KOAc (85.8 g, 911.1 mmol), and 1,4-dioxane (1000 ml) were mixed and stirred at 130° C. for 12 hours.

[0108] After the reaction was completed, the mixture was extracted with ethyl acetate and then cooled to 100° C. 4 The water was removed by filtration and the residue was purified by column chromatography (hexane:EA=8:1 (v / v)) to obtain 9-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-2,3,4,5,6,7,8-d7 (64.0 g, yield 56%). Mass (theoretical value: 376.3, measured value: 376 g / mol)

[0109] <Preparation Example 8-1-2> Synthesis of BCz-D13 [ka] Under a nitrogen stream, 9-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-2,3,4,5,6,7,8-d7 (64.0 g, 170.0 mmol), 3-bromo-9H-carbazole-1,2,4,5,6,7,8-d7 (51.7 g, 204.1 mmol), Pd(PPh 3 ) 4 (9.8g, 8.5mmol), K 2 CO 3 (58.8 g, 425.2 mmol), and 1,4-dioxane / H 2 O (1000 ml / 250 ml) was mixed and stirred at 120° C. for 4 hours.

[0110] After the reaction was completed, the mixture was extracted with methylene chloride and then washed with MgSO 4After removing the solvent from the obtained organic layer, the residue was purified by column chromatography (hexane:EA=7:1 (v / v)) to obtain BCz-D13 (37.3 g, yield 52%). Mass (theoretical value: 422.59, measured value: 422 g / mol)

[0111] <Preparation Example 8-2> Synthesis of BCz-D14 [ka] The target compound BCz-D14 (33.2 g, final yield 27.0%) was obtained in the same manner as in Preparation Example 8-1 above, except that Cz-D14 (100 g, 246.7 mmol) was used instead of Cz-D13. Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0112] <Preparation Example 8-3> Synthesis of BCz-D15 [ka] The target compound BCz-D15 (32.2 g, final yield 26.2%) was obtained in the same manner as in Preparation Example 8-1 above, except that Cz-D15 (100 g, 246.7 mmol) was used instead of Cz-D13. Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0113] <Preparation Example 8-4> Synthesis of BCz-D16 [ka] The target compound BCz-D16 (27.0 g, final yield 21.9%) was obtained in the same manner as in Preparation Example 8-1 above, except that Cz-D16 (100 g, 246.7 mmol) was used instead of Cz-D13. Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0114] <Preparation Example 9-1> Synthesis of BCz-D17 [ka] Under a nitrogen stream, 9-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-2,3,4,5,6,7,8-d7 (100.0 g, 170.0 mmol), 1-bromo-9H-carbazole-2,3,4,5,6,7,8-d7 (80.7 g, 318.8 mmol), Pd(PPh 3 ) 4 (15.3g, 13.2mmol), K 2 CO 3 (91.8 g, 664.2 mmol), and 1,4-dioxane / H 2 O (1000 ml / 250 ml) was mixed and stirred at 120° C. for 4 hours.

[0115] After the reaction was completed, the mixture was extracted with methylene chloride and then washed with MgSO 4 After removing the solvent from the obtained organic layer, the residue was purified by column chromatography (hexane:EA=7:1 (v / v)) to obtain BCz-D17 (50.5 g, yield 45%). Mass (theoretical value: 422.59, measured value: 422 g / mol)

[0116] <Preparation Example 9-2> Synthesis of BCz-D18 [ka] Under a nitrogen stream, 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,3,4,5,6,7,8-d7 (100.0 g, 170.0 mmol), 2-bromo-9H-carbazole-1,3,4,5,6,7,8-d7 (80.7 g, 318.8 mmol), Pd(PPh 3 ) 4 (15.3g, 13.2mmol), K 2 CO 3 (91.8 g, 664.2 mmol), and 1,4-dioxane / H 2 O (1000 ml / 250 ml) was mixed and stirred at 120° C. for 4 hours.

[0117] After the reaction was completed, the mixture was extracted with methylene chloride and then washed with MgSO 4 The organic layer was filtered after removing the solvent, and the residue was purified by column chromatography (hexane:EA=7:1 (v / v)) to obtain BCz-D18 (70.7 g, yield 63%). Mass (theoretical value: 422.59, measured value: 422 g / mol)

[0118] <Preparation Example 9-3> Synthesis of BCz-D19 [ka] Under a nitrogen stream, 9-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,3,5,6,7,8-d7 (100.0 g, 170.0 mmol), 4-bromo-9H-carbazole-1,2,3,5,6,7,8-d7 (80.7 g, 318.8 mmol), Pd(PPh 3 ) 4 (15.3g, 13.2mmol), K 2 CO 3 (91.8 g, 664.2 mmol), and 1,4-dioxane / H 2 O (1000 ml / 250 ml) was mixed and stirred at 120° C. for 4 hours.

[0119] After the reaction was completed, the mixture was extracted with methylene chloride and then washed with MgSO 4 The organic layer was filtered after removing the solvent, and the residue was purified by column chromatography (hexane:EA=7:1 (v / v)) to obtain BCz-D19 (59.5 g, yield 53%). Mass (theoretical value: 422.59, measured value: 422 g / mol)

[0120] [Synthesis Example 1] Synthesis of A-1 [ka] Under a nitrogen stream, BCz-D1 (10.0 g, 23.6 mmol), Cz-D1 (9.3 g, 28.3 mmol), and Pd(OAc) were2 (1.36 g, 1.18 mmol), P(t-Bu) 3 (0.57 ml, 2.36 mmol), NaO(t-Bu) (4.55 g, 47.3 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound A-1 (13.0 g, yield 82%). Mass (theoretical value: 670.93, measured value: 670g / mol)

[0121] [Synthesis Example 2] Synthesis of A-2 [ka] The target compound A-2 (13.8 g, 78% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D2 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0122] [Synthesis Example 3] Synthesis of A-3 [ka] The target compound A-3 (13.8 g, 75% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D3 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0123] [Synthesis Example 4] Synthesis of A-4 [ka] The target compound A-4 (12.2 g, 69% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D4 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0124] [Synthesis Example 5] Synthesis of A-5 [ka] The target compound A-5 (8.73 g, 55% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D5 (9.3 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 670.93, measured value: 670g / mol)

[0125] [Synthesis Example 6] Synthesis of A-6 [ka] The target compound A-6 (7.42 g, 42% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D6 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0126] [Synthesis Example 7] Synthesis of A-7 [ka] The target compound A-7 (8.83 g, 50% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D7 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0127] [Synthesis Example 8] Synthesis of A-8 [ka] The target compound A-8 (9.89 g, 56% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D8 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0128] [Synthesis Example 9] Synthesis of A-9 [ka] The target compound A-9 (8.41 g, 53% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D9 (9.3 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 670.93, measured value: 670g / mol)

[0129] [Synthesis Example 10] Synthesis of A-10 [ka] The target compound A-10 (8.66 g, 49% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D10 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0130] [Synthesis Example 11] Synthesis of A-11 [ka] The target compound A-11 (9.01 g, 51% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D11 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0131] [Synthesis Example 12] Synthesis of A-12 [ka] The target compound A-12 (9.19 g, 52% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D12 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0132] [Synthesis Example 13] Synthesis of A-13 [ka] The target compound A-13 (9.52 g, 60% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D13 (9.3 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 670.93, measured value: 670g / mol)

[0133] [Synthesis Example 14] Synthesis of A-14 [ka] The target compound A-14 (10.78 g, 61% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D14 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0134] [Synthesis Example 15] Synthesis of A-15 [ka] The target compound A-15 (11.13 g, 63% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D15 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0135] [Synthesis Example 16] Synthesis of A-16 [ka] The target compound A-16 (9.02 g, 51% yield) was obtained in the same manner as in Synthesis Example 1 above, except that Cz-D16 (10.0 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0136] [Synthesis Example 17] Synthesis of B-1 [ka] Under a nitrogen stream, BCz-D2 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), and Pd(OAc) were 2 (1.15 g, 1.0 mmol), P(t-Bu) 3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound B-1 (10.2 g, yield 62%). Mass (theoretical value: 747.02, measured value: 747g / mol)

[0137] [Synthesis Example 18] Synthesis of B-2 [ka] The target compound B-2 (11.9 g, 72% yield) was obtained in the same manner as in Synthesis Example 5 above, except that Cz-D2 (9.75 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 823.12, measured value: 823 g / mol)

[0138] [Synthesis Example 19] Synthesis of B-3 [ka] The target compound B-3 (10.9 g, 66% yield) was obtained in the same manner as in Synthesis Example 5 above, except that Cz-D3 (9.75 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 823.12, measured value: 823 g / mol)

[0139] [Synthesis Example 20] Synthesis of B-4 [ka] The target compound B-4 (9.6 g, 58% yield) was obtained in the same manner as in Synthesis Example 5 above, except that Cz-D4 (9.75 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 823.12, measured value: 823 g / mol)

[0140] [Synthesis Example 21] Synthesis of B-5 [ka] The target compound B-5 (8.5 g, 48% yield) was obtained in the same manner as in Synthesis Example 17 above, except that Cz-D5 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0141] [Synthesis Example 22] Synthesis of B-6 [ka] The target compound B-6 (11.1 g, 63% yield) was obtained in the same manner as in Synthesis Example 17 above, except that Cz-D9 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0142] [Synthesis Example 23] Synthesis of B-7 [ka] The target compound B-7 (7.42 g, 42% yield) was obtained in the same manner as in Synthesis Example 17 above, except that Cz-D13 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0143] [Synthesis Example 24] Synthesis of C-1 [ka] Under a nitrogen stream, BCz-D3 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), and Pd(OAc) were 2 (1.15 g, 1.0 mmol), P(t-Bu) 3(0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound C-1 (9.4 g, yield 63%). Mass (theoretical value: 747.02, measured value: 747g / mol)

[0144] [Synthesis Example 25] Synthesis of C-2 [ka] The target compound C-2 (12.2 g, 74% yield) was obtained in the same manner as in Synthesis Example 24 above, except that Cz-D2 (9.75 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 823.12, measured value: 823 g / mol)

[0145] [Synthesis Example 26] Synthesis of C-3 [ka] The target compound C-3 (12.9 g, 78% yield) was obtained in the same manner as in Synthesis Example 24 above, except that Cz-D3 (9.75 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 823.12, measured value: 823 g / mol)

[0146] [Synthesis Example 27] Synthesis of C-4 [ka] The target compound C-4 (10.1 g, 61% yield) was obtained in the same manner as in Synthesis Example 24 above, except that Cz-D4 (9.75 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 823.12, measured value: 823 g / mol)

[0147] [Synthesis Example 28] Synthesis of C-5 [ka] The target compound C-5 (7.78 g, 44% yield) was obtained in the same manner as in Synthesis Example 24 above, except that Cz-D5 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0148] [Synthesis Example 29] Synthesis of C-6 [ka] The target compound C-6 (11.67 g, 66% yield) was obtained in the same manner as in Synthesis Example 24 above, except that Cz-D9 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0149] [Synthesis Example 30] Synthesis of C-7 [ka] The target compound C-7 (6.89 g, 39% yield) was obtained in the same manner as in Synthesis Example 24 above, except that Cz-D13 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0150] [Synthesis Example 31] Synthesis of D-1 [ka] Under a nitrogen stream, BCz-D4 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), and Pd(OAc) were 2 (1.15 g, 1.0 mmol), P(t-Bu) 3(0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound D-1 (8.1 g, yield 54%). Mass (theoretical value: 747.02, measured value: 747g / mol)

[0151] [Synthesis Example 32] Synthesis of D-2 [ka] The target compound D-2 (10.9 g, 66% yield) was obtained in the same manner as in Synthesis Example 31 above, except that Cz-D2 (9.75 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 823.12, measured value: 823 g / mol)

[0152] [Synthesis Example 33] Synthesis of D-3 [ka] The target compound D-3 (9.1 g, 55% yield) was obtained in the same manner as in Synthesis Example 31 above, except that Cz-D3 (9.75 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 823.12, measured value: 823 g / mol)

[0153] [Synthesis Example 34] Synthesis of D-4 [ka] The target compound D-4 (7.1 g, 43% yield) was obtained in the same manner as in Synthesis Example 31 above, except that Cz-D4 (9.75 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 823.12, measured value: 823 g / mol)

[0154] [Synthesis Example 35] Synthesis of D-5 [ka] The target compound D-5 (7.24 g, 41% yield) was obtained in the same manner as in Synthesis Example 31 above, except that Cz-D5 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0155] [Synthesis Example 36] Synthesis of D-6 [ka] The target compound D-6 (8.41 g, 51% yield) was obtained in the same manner as in Synthesis Example 31 above, except that Cz-D9 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0156] [Synthesis Example 37] Synthesis of D-7 [ka] The target compound D-7 (5.47 g, 31% yield) was obtained in the same manner as in Synthesis Example 31 above, except that Cz-D13 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0157] [Synthesis Example 38] Synthesis of E-1 [ka] Under a nitrogen stream, BCz-D5 (10.0 g, 23.6 mmol), Cz-D1 (9.3 g, 28.3 mmol), and Pd(OAc) were 2 (1.36 g, 1.18 mmol), P(t-Bu) 3(0.57 ml, 2.36 mmol), NaO(t-Bu) (4.55 g, 47.3 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound E-1 (11.43 g, yield 72%). Mass (theoretical value: 670.93, measured value: 670g / mol)

[0158] [Synthesis Example 39] Synthesis of E-2 [ka] The target compound E-2 (10.00 g, yield 63%) was obtained in the same manner as in Synthesis Example 38 above, except that Cz-D5 (9.3 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 670.93, measured value: 670g / mol)

[0159] [Synthesis Example 40] Synthesis of E-3 [ka] The target compound E-3 (8.73 g, 55% yield) was obtained in the same manner as in Synthesis Example 38 above, except that Cz-D9 (9.3 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 670.93, measured value: 670g / mol)

[0160] [Synthesis Example 41] Synthesis of E-4 [ka] The target compound E-4 (9.21 g, 58% yield) was obtained in the same manner as in Synthesis Example 38 above, except that Cz-D13 (9.3 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 670.93, measured value: 670g / mol)

[0161] [Synthesis Example 42] Synthesis of F-1 [ka] Under a nitrogen stream, BCz-D6 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), and Pd(OAc) were 2 (1.15 g, 1.0 mmol), P(t-Bu) 3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound F-1 (13.79 g, 78% yield). Mass (theoretical value: 747.02, measured value: 747g / mol)

[0162] [Synthesis Example 43] Synthesis of F-2 [ka] The target compound F-2 (11.84 g, 67% yield) was obtained in the same manner as in Synthesis Example 42 above, except that Cz-D5 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0163] [Synthesis Example 44] Synthesis of F-3 [ka] The target compound F-3 (11.31 g, 64% yield) was obtained in the same manner as in Synthesis Example 42 above, except that Cz-D9 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0164] [Synthesis Example 45] Synthesis of F-4 [ka] The target compound F-4 (9.90 g, 56% yield) was obtained in the same manner as in Synthesis Example 42 above, except that Cz-D13 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0165] [Synthesis Example 46] Synthesis of G-1 [ka] Under nitrogen flow, BCz-D7 (10.0g, 20.1mmol), Cz-D1 (7.9g, 24.1mmol), Pd(OAc) 2 (1.15 g, 1.0 mmol), P(t-Bu) 3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound G-1 (12.90 g, 73% yield). Mass (theoretical value: 747.02, measured value: 747g / mol)

[0166] [Synthesis Example 47] Synthesis of G-2 [ka] The target compound G-2 (12.55 g, 71% yield) was obtained in the same manner as in Synthesis Example 46 above, except that Cz-D5 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0167] [Synthesis Example 48] Synthesis of G-3 [ka] The target compound G-3 (13.08 g, 74% yield) was obtained in the same manner as in Synthesis Example 46 above, except that Cz-D9 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0168] [Synthesis Example 49] Synthesis of G-4 [ka] The target compound G-4 (9.37 g, 53% yield) was obtained in the same manner as in Synthesis Example 46 above, except that Cz-D13 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0169] [Synthesis Example 50] Synthesis of H-1 [ka] Under a nitrogen stream, BCz-D8 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), and Pd(OAc) were 2 (1.15 g, 1.0 mmol), P(t-Bu) 3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound H-1 (13.42 g, 76% yield). Mass (theoretical value: 747.02, measured value: 747g / mol)

[0170] [Synthesis Example 51] Synthesis of H-2 [ka] The target compound H-2 (11.84 g, 67% yield) was obtained in the same manner as in Synthesis Example 50 above, except that Cz-D5 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0171] [Synthesis Example 52] Synthesis of H-3 [ka] The target compound H-3 (13.26 g, 75% yield) was obtained in the same manner as in Synthesis Example 50 above, except that Cz-D9 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0172] [Synthesis Example 53] Synthesis of H-4 [ka] The target compound H-4 (9.19 g, 52% yield) was obtained in the same manner as in Synthesis Example 50 above, except that Cz-D13 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0173] [Synthesis Example 54] Synthesis of I-1 [ka] Under a nitrogen stream, BCz-D9 (10.0 g, 23.6 mmol), Cz-D1 (9.3 g, 28.3 mmol), and Pd(OAc) were 2 (1.36 g, 1.18 mmol), P(t-Bu) 3 (0.57 ml, 2.36 mmol), NaO(t-Bu) (4.55 g, 47.3 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and purified by recrystallization to obtain the target compound I-1 (11.27 g, 71% yield). Mass (theoretical value: 670.93, measured value: 670g / mol)

[0174] [Synthesis Example 55] Synthesis of I-2 [ka] The target compound I-2 (10.63 g, 67% yield) was obtained in the same manner as in Synthesis Example 54 above, except that Cz-D5 (9.3 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 670.93, measured value: 670g / mol)

[0175] [Synthesis Example 56] Synthesis of I-3 [ka] The target compound I-3 (8.25 g, 52% yield) was obtained in the same manner as in Synthesis Example 54 above, except that Cz-D9 (9.3 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 670.93, measured value: 670g / mol)

[0176] [Synthesis Example 57] Synthesis of I-4 [ka] The target compound I-4 (8.10 g, 51% yield) was obtained in the same manner as in Synthesis Example 54 above, except that Cz-D13 (9.3 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 670.93, measured value: 670g / mol)

[0177] [Synthesis Example 58] Synthesis of J-1 [ka] Under a nitrogen stream, BCz-D10 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), and Pd(OAc) were 2 (1.15 g, 1.0 mmol), P(t-Bu) 3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound J-1 (12.90 g, 73% yield). Mass (theoretical value: 747.02, measured value: 747g / mol)

[0178] [Synthesis Example 59] Synthesis of J-2 [ka] The target compound J-2 (11.49 g, 65% yield) was obtained in the same manner as in Synthesis Example 58 above, except that Cz-D5 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0179] [Synthesis Example 60] Synthesis of J-3 [ka] The target compound J-3 (10.95 g, 62% yield) was obtained in the same manner as in Synthesis Example 58 above, except that Cz-D9 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0180] [Synthesis Example 61] Synthesis of J-4 [ka] The target compound J-4 (10.25 g, 58% yield) was obtained in the same manner as in Synthesis Example 58 above, except that Cz-D13 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0181] [Synthesis Example 62] Synthesis of K-1 [ka] Under a nitrogen stream, BCz-D11 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), and Pd(OAc) were 2 (1.15 g, 1.0 mmol), P(t-Bu) 3(0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound K-1 (12.37 g, 70% yield). Mass (theoretical value: 747.02, measured value: 747g / mol)

[0182] [Synthesis Example 63] Synthesis of K-2 [ka] The target compound K-2 (13.61 g, 77% yield) was obtained in the same manner as in Synthesis Example 62 above, except that Cz-D5 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0183] [Synthesis Example 64] Synthesis of K-3 [ka] The target compound K-3 (12.55 g, 71% yield) was obtained in the same manner as in Synthesis Example 62 above, except that Cz-D9 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0184] [Synthesis Example 65] Synthesis of K-4 [ka] The target compound K-4 (10.61 g, 60% yield) was obtained in the same manner as in Synthesis Example 62 above, except that Cz-D13 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0185] [Synthesis Example 66] Synthesis of L-1 [ka] Under a nitrogen stream, BCz-D12 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), and Pd(OAc) were 2 (1.15 g, 1.0 mmol), P(t-Bu) 3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound L-1 (13.42 g, 76% yield). Mass (theoretical value: 747.02, measured value: 747g / mol)

[0186] [Synthesis Example 67] Synthesis of L-2 [ka] The target compound L-2 (11.84 g, 67% yield) was obtained in the same manner as in Synthesis Example 66 above, except that Cz-D5 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0187] [Synthesis Example 68] Synthesis of L-3 [ka] The target compound L-3 (13.26 g, 75% yield) was obtained in the same manner as in Synthesis Example 66, except that Cz-D9 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0188] [Synthesis Example 69] Synthesis of L-4 [ka] The target compound L-4 (9.19 g, 52% yield) was obtained in the same manner as in Synthesis Example 66 above, except that Cz-D13 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747g / mol)

[0189] [Synthesis Example 70] Synthesis of M-1 [ka] Under a nitrogen stream, BCz-D13 (10.0 g, 23.6 mmol), Cz-D1 (9.3 g, 28.3 mmol), and Pd(OAc) were 2 (1.36 g, 1.18 mmol), P(t-Bu) 3 (0.57 ml, 2.36 mmol), NaO(t-Bu) (4.55 g, 47.3 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound M-1 (10.16 g, yield 64%). Mass (theoretical value: 670.93, measured value: 670g / mol)

[0190] [Synthesis Example 71] Synthesis of M-2 [ka] The target compound M-2 (9.37 g, 59% yield) was obtained in the same manner as in Synthesis Example 70 above, except that Cz-D5 (9.3 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 670.93, measured value: 670g / mol)

[0191] [Synthesis Example 72] Synthesis of M-3 [ka] The target compound M-3 (7.78 g, 49% yield) was obtained in the same manner as in Synthesis Example 70 above, except that Cz-D9 (9.3 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 670.93, measured value: 670g / mol)

[0192] [Synthesis Example 73] Synthesis of M-4 [ka] The target compound M-4 (6.82 g, 43% yield) was obtained in the same manner as in Synthesis Example 70 above, except that Cz-D13 (9.3 g, 23.6 mmol) was used instead of Cz-D1. Mass (theoretical value: 670.93, measured value: 670g / mol)

[0193] [Synthesis Example 74] Synthesis of N-1 [ka] Under a nitrogen stream, BCz-D14 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), and Pd(OAc) were 2 (1.15 g, 1.0 mmol), P(t-Bu) 3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound N-1 (11.49 g, yield 65%). Mass (theoretical value: 747.02, measured value: 747g / mol)

[0194] [Synthesis Example 75] Synthesis of N-2 [ka] The target compound N-2 (10.96 g, 62% yield) was obtained in the same manner as in Synthesis Example 74 above, except that Cz-D5 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0195] [Synthesis Example 76] Synthesis of N-3 [ka] The target compound N-3 (9.55 g, 54% yield) was obtained in the same manner as in Synthesis Example 74 above, except that Cz-D9 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0196] [Synthesis Example 77] Synthesis of N-4 [ka] The target compound N-4 (8.84 g, 50% yield) was obtained in the same manner as in Synthesis Example 74 above, except that Cz-D13 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0197] [Synthesis Example 78] Synthesis of O-1 [ka] Under a nitrogen stream, BCz-D15 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), and Pd(OAc) were 2 (1.15 g, 1.0 mmol), P(t-Bu) 3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound O-1 (11.14 g, yield 63%). Mass (theoretical value: 747.02, measured value: 747g / mol)

[0198] [Synthesis Example 79] Synthesis of O-2 [ka] The target compound O-2 (11.49 g, 65% yield) was obtained in the same manner as in Synthesis Example 78 above, except that Cz-D5 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0199] [Synthesis Example 80] Synthesis of O-3 [ka] The target compound O-3 (10.07 g, 57% yield) was obtained in the same manner as in Synthesis Example 78 above, except that Cz-D9 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0200] [Synthesis Example 81] Synthesis of O-4 [ka] The target compound O-4 (8.49 g, 48% yield) was obtained in the same manner as in Synthesis Example 78 above, except that Cz-D13 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0201] [Synthesis Example 82] Synthesis of P-1 [ka] Under a nitrogen stream, BCz-D16 (10.0 g, 20.1 mmol), Cz-D1 (7.9 g, 24.1 mmol), and Pd(OAc) were 2 (1.15 g, 1.0 mmol), P(t-Bu) 3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound P-1 (10.95 g, 62% yield). Mass (theoretical value: 747.02, measured value: 747g / mol)

[0202] [Synthesis Example 83] Synthesis of P-2 [ka] The target compound P-2 (11.31 g, 64% yield) was obtained in the same manner as in Synthesis Example 82 above, except that Cz-D5 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0203] [Synthesis Example 84] Synthesis of P-3 [ka] The target compound P-3 (11.84 g, 67% yield) was obtained in the same manner as in Synthesis Example 82 above, except that Cz-D9 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0204] [Synthesis Example 85] Synthesis of P-4 [ka] The target compound P-4 (9.55 g, 54% yield) was obtained in the same manner as in Synthesis Example 82 above, except that Cz-D13 (7.9 g, 24.1 mmol) was used instead of Cz-D1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0205] [Synthesis Example 86] Synthesis of Q-1 [ka] Under a nitrogen stream, BCz-D17 (10.0 g, 23.6 mmol), Cz-D1 (9.3 g, 28.3 mmol), and Pd(OAc) were 2 (1.36 g, 1.18 mmol), P(t-Bu) 3(0.57 ml, 2.36 mmol), NaO(t-Bu) (4.55 g, 47.3 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound Q-1 (6.67 g, 42% yield). Mass (theoretical value: 670.93, measured value: 670g / mol)

[0206] [Synthesis Example 87] Synthesis of R-1 [ka] Under a nitrogen stream, BCz-D18 (10.0 g, 23.6 mmol), Cz-D1 (9.3 g, 28.3 mmol), and Pd(OAc) were 2 (1.36 g, 1.18 mmol), P(t-Bu) 3 (0.57 ml, 2.36 mmol), NaO(t-Bu) (4.55 g, 47.3 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound R-1 (11.27 g, 71% yield). Mass (theoretical value: 670.93, measured value: 670g / mol)

[0207] [Synthesis Example 88] Synthesis of S-1 [ka] Under a nitrogen stream, BCz-D19 (10.0 g, 23.6 mmol), Cz-D1 (9.3 g, 28.3 mmol), and Pd(OAc) were 2 (1.36 g, 1.18 mmol), P(t-Bu) 3 (0.57 ml, 2.36 mmol), NaO(t-Bu) (4.55 g, 47.3 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound S-1 (11.75 g, 74% yield). Mass (theoretical value: 670.93, measured value: 670g / mol)

[0208] [Synthesis Example 89] Synthesis of T-1 [ka] Under a nitrogen stream, BCz-D3 (10.0 g, 20.1 mmol), 3-bromo-9-phenyl-9H-carbazole (7.8 g, 24.1 mmol), and Pd(OAc) 2 (1.15 g, 1.0 mmol), P(t-Bu) 3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound T-1 (10.8 g, 73% yield). Mass (theoretical value: 739.98, measured value: 739 g / mol)

[0209] [Synthesis Example 90] Synthesis of U-1 [ka] Under a nitrogen stream, BCz-D3 (10.0 g, 20.1 mmol), 9-([1,1'-biphenyl]-4-yl-2',3',4',5',6'-d5)-3-bromo-9H-carbazole (9.7 g, 24.1 mmol), and Pd(OAc) were 2 (1.15 g, 1.0 mmol), P(t-Bu) 3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 mmol), and toluene (100 ml) were mixed and stirred at 110° C. for 5 hours. After the reaction was completed, the toluene was concentrated, and the solid salt was filtered and then purified by recrystallization to obtain the target compound U-1 (10.7 g, yield 65%). Mass (theoretical value: 821.11, measured value: 821g / mol)

[0210] [Reference example] In the examples and evaluation examples described later, the compounds HT, HA, PA, and Ir(ppy) used in the manufacture of the organic EL device 3, E.A., E.T., (piq) 2 The structures of Ir(acac) and CBP are as follows: [ka]

[0211] [Example 1: Fabrication of green organic EL element] Compound A-1 synthesized in Synthesis Example 1 was purified to high purity by sublimation in a conventional manner, and then a green organic EL device was fabricated according to the following process.

[0212] First, a glass substrate coated with a thin film of ITO (Indium Tin Oxide) at a thickness of 1500 Å was ultrasonically cleaned with distilled water. After cleaning with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, and the substrate was then dried and transferred to a UV ozone cleaner (Power sonic 405, manufactured by Fashintech Co., Ltd.) where it was cleaned with UV for 5 minutes and then transferred to a vacuum deposition machine.

[0213] On the ITO transparent electrode thus prepared, HT+2%PA(100Å) / HT(1200Å) / HA(300Å) / 60% compound A-1+30%Solus E-typeHOST+10%Ir(ppy) 3 An organic electroluminescence (EL) element was fabricated by stacking the layers in the following order: (400 Å) / EA(50 Å) / ET+LiQ(300 Å_1:1 molar ratio) / LiF(10 Å) / Al(1000 Å).

[0214] [Examples 2 to 88] Fabrication of green organic EL elements Green organic EL devices of Examples 2 to 90 were produced in the same manner as in Example 1 above, except that compounds A-2 to U-1 synthesized in Synthesis Examples 2 to 9, respectively, were used as the light-emitting host material instead of compound A-1 when forming the light-emitting layer (see Tables 1 and 2 below).

[0215] [Comparative Example 1] Fabrication of green organic EL element A green organic EL device of Comparative Example 1 was fabricated in the same manner as in Example 1, except that in forming the light-emitting layer, compound A-1-1, which has the same structure as compound A-1 but is not deuterium (D)-substituted, was used instead of compound A-1 as the light-emitting host material. The structure of compound A-1-1 used is as follows: [ka]

[0216] [Comparative Example 2] Fabrication of green organic EL element A green organic EL device of Comparative Example 2 was fabricated in the same manner as in Example 2, except that in forming the light-emitting layer, compound A-2-1, which has the same structure as compound A-2 but is not substituted with deuterium (D), was used instead of compound A-2 as the light-emitting host material. The structure of compound A-2-1 used is as follows: [ka]

[0217] [Comparative Example 3] Fabrication of green organic EL element A green organic EL device of Comparative Example 3 was fabricated in the same manner as in Example 3, except that in forming the light-emitting layer, compound A-3-1, which has the same structure as compound A-3 but is not deuterium (D)-substituted, was used instead of compound A-3 as the light-emitting host material. The structure of compound A-3-1 is as follows: [ka]

[0218] [Comparative Example 4] Fabrication of green organic EL element A green organic EL device of Comparative Example 4 was fabricated in the same manner as in Example 4, except that in forming the light-emitting layer, compound A-4-1, which has the same structure as compound A-4 but is not deuterium (D)-substituted, was used instead of compound A-4 as the light-emitting host material. The structure of compound A-4-1 used is as follows: [ka]

[0219] [Evaluation example 1] For the green organic EL devices produced in Examples 1 to 4 and Comparative Examples 1 to 4, a current density of 10 mA / cm 2 The driving voltage, current efficiency, emission peak, and lifetime were measured at 1000 Hz, and the results are shown in Table 1 below.

[0220] [Table 1]

[0221] As shown in Table 1 above, the green organic EL devices obtained in Examples 1 to 4 using Compounds A-1 to A-4 according to the present invention as the light-emitting layer material were superior in terms of device efficiency, driving voltage, and life characteristics to those obtained in Comparative Examples 1 to 4 using Compounds A-1-1 to A-4-1 having the same structure but unsubstituted with deuterium (d).

[0222] [Evaluation example 2] For the green organic EL devices fabricated in Examples 5 to 90 described below, a current density of 10 mA / cm 2 The driving voltage, current efficiency, emission peak, and lifetime were measured at 1000 Hz, and the results are shown in Table 2 below.

[0223] [Table 2] JPEG2025515662000163.jpg255165

[0224] As shown in Table 2 above, the green organic EL devices obtained in Examples 5 to 90 using the compounds A-1 to S-1 according to the present invention as the light-emitting layer material were confirmed to be excellent in terms of device efficiency, driving voltage, and life characteristics, similar to the green organic EL devices obtained in Examples 1 to 4 described above.

[0225] [Example 91] Fabrication of red organic EL element Compound A-1 synthesized in Synthesis Example 1 was purified by sublimation to a high purity by a conventional method, and then a red organic EL device was fabricated according to the following process.

[0226] First, a glass substrate coated with a thin film of ITO (Indium Tin Oxide) at a thickness of 1500 Å was ultrasonically cleaned with distilled water. After cleaning with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, and the substrate was then dried and transferred to a UV ozone cleaner (Power sonic 405, manufactured by Fashintech Co., Ltd.) where it was cleaned with UV for 5 minutes and then transferred to a vacuum deposition machine.

[0227] On the ITO transparent electrode thus prepared, HT+2%PA(100Å) / HT(1200Å) / HA(300Å) / 50% compound A-1+40%Solus E-typeHOST+10%(piq) 2 An organic electroluminescence (EL) device was fabricated by stacking Ir(acac)(400 Å) / EA(50 Å) / ET+LiQ(300 Å_1:1 molar ratio) / LiF(10 Å) / Al(1000 Å) in that order.

[0228] [Examples 92 to 106] Fabrication of red organic EL elements A red organic EL device was produced in the same manner as in Example 89, except that, in forming the light-emitting layer, instead of compound A-1, compounds A-2 to A-16 synthesized in Synthesis Examples 2 to 16 were used as light-emitting host materials (see Table 3 below).

[0229] [Comparative Example 5] A red organic electroluminescent device of Comparative Example 5 was produced in the same manner as in Example 91, except that, in forming the light-emitting layer, CBP was used as the light-emitting host material instead of Compound A-1.

[0230] [Evaluation example 3] For the organic EL devices fabricated in Examples 91 to 106 and Comparative Example 5, a current density of 10 mA / cm 2 The driving voltage and current efficiency were measured at 1000 V and the results are shown in Table 3 below.

[0231] [Table 3]

[0232] As shown in Table 3 above, the red organic EL devices obtained in Examples 91 to 106 using the compounds A-1 to A16 according to the present invention as the light-emitting layer material were superior in terms of device efficiency and driving voltage to those obtained in Comparative Example 5 using the conventional CBP.

[0233] [Examples 107-110] Fabrication of green organic EL elements Compound A-1 synthesized in Synthesis Example 1 was purified to high purity by sublimation in a conventional manner, and then a green organic EL device was fabricated according to the following process.

[0234] First, a glass substrate coated with a thin film of ITO (Indium Tin Oxide) at a thickness of 1200 Å was ultrasonically cleaned in distilled water. After cleaning with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, and the substrate was then dried and transferred to a UV ozone cleaner (Power sonic 405, manufactured by Fashintech Co., Ltd.) where it was cleaned with UV for 5 minutes before being transferred to a vacuum deposition machine.

[0235] On the ITO transparent electrode thus prepared, HT+2%PA(100Å) / HT(1200Å) / HA(300Å) / 60% compound A-1+30%Solus E-typeHOST+10%Ir(ppy) 3 The organic electroluminescence (EL) element was fabricated by stacking the layers in the order of (400 Å) / EA(50 Å) / ET-1 to ET-4+LiQ(300 Å_1:1 molar ratio) / LiF(10 Å) / Al(1000 Å).

[0236] At this time, the compounds ET-1, ET-2, ET-3, and ET-4 used as the electron transport layer materials are dual electron transfer type materials, and their structures are as follows: [ka]

[0237] [Examples 111 to 114] A green organic EL device was manufactured in the same manner as in Examples 107 to 110, except that the compound A-2 synthesized in Synthesis Example 2 was used as the light-emitting host material instead of the compound A-1 when forming the light-emitting layer (see Table 4 below).

[0238] [Examples 115 to 118] A green organic EL device was produced in the same manner as in Examples 107 to 110, except that the compound A-3 synthesized in Synthesis Example 3 was used as the light-emitting host material instead of the compound A-1 when forming the light-emitting layer (see Table 4 below).

[0239] [Examples 119 to 122] A green organic EL device was manufactured in the same manner as in Examples 107 to 110, except that compound A-4 synthesized in Synthesis Example 4 was used as the light-emitting host material instead of compound A-1 when forming the light-emitting layer (see Table 4 below).

[0240] [Comparative Examples 6 to 9] Fabrication of green organic EL elements A green organic EL device was fabricated in the same manner as in Example 107, except that a single electron transport type material ET having one EWG was used instead of ET-1 as the electron transport layer material, and A-1 to A-4 were used as the light-emitting host materials, respectively. [ka]

[0241] [Evaluation example 4] For the organic EL devices fabricated in Examples 107 to 122 and Comparative Examples 6 to 9, a current density of 10 mA / cm 2 The driving voltage, current efficiency, emission wavelength, and lifetime (T 97 ) were measured, and the results are shown in Table 4 below.

[0242] [Table 4]

[0243] As can be seen from Table 4 above, the green organic EL devices obtained in Examples 107 to 122 using the emitting layer material containing the deuterated compounds A-1 to A-4 and the dual EWG type electron transport layer material were significantly improved in terms of device driving voltage, current efficiency, and life characteristics compared to those obtained in Comparative Examples 6 to 9 using the deuterated compound and the existing single EWG type electron transport layer. This shows that a great synergy effect is realized in terms of device performance characteristics by combining the excellent hole stability derived from the deuterated compound of the present invention used as the emitting layer material and the high electron transport ability derived from the dual EWG type electron transport layer material. As a result, it was found that in the present invention, by using the emitting layer containing the compound represented by the above [Chemical Formula 1] in combination with the dual EWG type electron transport layer containing at least two EWG groups, the hole stability of the emitting layer (EML) can be improved and the electron transport ability of the electron transport layer (ETL) can be maximized, thereby optimizing the performance of the organic EL device.

Claims

1. A compound represented by the following [chemical formula 1]: 【Chemistry 1】 (In the formula, Ar １ and Ar ２ are the same or different, and each independently represents １ ~C ４０ Alkyl groups of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ６ ~C ４０ an aryl group having 5 to 40 ring atoms; ６ ~C ４０ an aryloxy group of C １ ~C ４０ an alkyloxy group of C ６ ~C ４０ an arylamine group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; １ ~C ４０ an alkylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ４０ an arylboron group of C ６ ~C ４０ an arylphosphine group of C ６ ~C ４０ and an arylphosphine oxide group of C ６ ~C ４０ and wherein the arylsilyl group is selected from the group consisting of a, d, and f each independently represent 1 to 3; b, c, and e each independently represent 1 to 4, provided that a+b+c+d+e+f≧15; The hydrogen in the benzene ring of carbazole, which is unsubstituted with deuterium (D), is C １ ~C ４０ Alkyl groups of C ６ ~C ４０ and heteroaryl groups having 5 to 40 ring atoms, The above Ar １ ~Ar ２ The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylsilyl group each independently represent a deuterium (D), a halogen, a cyano group, a nitro group, a C １ ~C ４０ Alkyl groups of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; ６ ~C ４０ an aryl group having 5 to 40 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ４０ an arylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ４０ an arylboron group of C ６ ~C ４０ an arylphosphine group of C ６ ~C ４０ and an arylphosphine oxide group of C ６ ~C ４０ and wherein, when there are a plurality of the above-mentioned substituents, they may be the same or different from each other.)

2. The compound according to claim 1, wherein the compound represented by the above [Chemical Formula 1] contains 21 or more deuterium (D).

3. Ar １ and Ar ２ are the same or different, and each independently represents ６ ~C ４０ and heteroaryl groups having 5 to 40 ring atoms, The above Ar １ ~Ar ２ The aryl group and the heteroaryl group each independently represent deuterium (D), a halogen, a cyano group, C ６ ~C ４０ and heteroaryl groups having 5 to 40 ring atoms, or are unsubstituted or substituted with one or more substituents selected from the group consisting of aryl groups having the formula:

4. Ar １ and Ar ２ are each independently selected from the group consisting of the following substituents S1 to S9. 【Chemistry 2】 (In the formula, * indicates the bonding site with the above [Chemical Formula 1].)

5. The compound represented by the above [Chemical Formula 1] is represented by any one of the following [Chemical Formula 2] to [Chemical Formula 17]. The compound according to claim 1. 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 (In the formula, Ar １ , Ar ２ , a, b, c, d, e, and f are each as defined in claim 1.

6. The compound according to claim 1 , wherein the compound represented by the above [Chemical Formula 1] is a host material for a light-emitting layer.

7. The compound according to claim 1, wherein the compound represented by the above [Chemical Formula 1] is selected from the group consisting of the following compounds A-1 to U-1. 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemical 22】

8. The battery includes a positive electrode, a negative electrode, and one or more organic layers interposed between the positive electrode and the negative electrode, An organic electroluminescence device, wherein at least one of the one or more organic layers comprises the compound according to any one of claims 1 to 7.

9. the one or more organic layers include at least one 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, an electron transport layer, and an electron transport auxiliary layer; The organic electroluminescence device according to claim 8 , wherein the light-emitting layer contains the compound represented by the formula 1 as a host.

10. The organic electroluminescence device according to claim 9 , wherein the light-emitting layer further comprises at least one of a P-type host material, an N-type host material, a fluorescent dopant, and a phosphorescent dopant.

11. The organic electroluminescence device according to claim 9 , wherein the electron transport layer contains a compound represented by the following [Chemical Formula 18]: 【Chemistry 23】 (In the formula, L is C ６ ~C ４０ and substituted or unsubstituted heteroarylene groups having 5 to 40 ring atoms, X １ ~X １０ Each independently represents N or (CR １ ) and The above C(R １ When there are a plurality of R １ are the same or different, and each independently represents １ ~C ４０ Alkyl groups of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ６ ~C ４０ an aryl group having 5 to 40 ring atoms; ６ ~C ４０ an aryloxy group of C １ ~C ４０ an alkyloxy group of C ６ ~C ４０ an arylamine group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; １ ~C ４０ an alkylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ４０ an arylboron group of C ６ ~C ４０ an arylphosphine group of C ６ ~C ４０ and an arylphosphine oxide group of C ６ ~C ４０ and wherein the arylsilyl group is selected from the group consisting of The arylene group and heteroarylene group of L and the R １ The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, and arylsilyl group each independently represent a deuterium (D), a halogen, a cyano group, a nitro group, a C １ ~C ４０ Alkyl groups of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; ６ ~C ６０ an aryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ６０ an arylboron group of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ and an arylphosphine oxide group of C ６ ~C ６０ In this case, when there are a plurality of the above-mentioned substituents, they may be the same or different from each other.)

12. Above X １ ~X ５ Containing ring and X ６ ~X １０ The organic electroluminescence device according to claim 11, wherein the containing rings are the same or different and each is independently selected from the group consisting of the following substituents A-1 to A-5: 【Chemistry 24】 (In the formula, Z １ and Z ２ are the same or different, and each independently represents ６ ~C ４０ and heteroaryl groups having 5 to 40 ring atoms, R １ are each independently hydrogen, C １ ~C ４０ Alkyl groups of C ６ ~C ４０ and heteroaryl groups having 5 to 40 ring atoms, Above Z １ ~Z ２ The aryl and heteroaryl groups of the above R １ The alkyl group, aryl group, and heteroaryl group each independently represent deuterium (D), halogen, cyano group, C ６ ~C ４０ and heteroaryl groups having 5 to 40 ring atoms, and in this case, when there are a plurality of the above-mentioned substituents, they may be the same or different.)

13. Above Z １ and Z ２ The organic electroluminescence device according to claim 12 , wherein each of the groups is independently selected from the following structural formulas: 【Chemistry 25】 (In the formula, * is the bonding site with the above [Chemical Formula 18].)

14. The organic electroluminescence device according to claim 11 , wherein L is a linker selected from the following structural formulas: 【Chemistry 26】 (In the formula, * is the bonding site with the above [Chemical Formula 18].)

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