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

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent element using the same, and more specifically, to a novel compound having excellent thermal stability and luminescence ability and an organic electroluminescent element having improved characteristics such as thermal stability, high luminescence efficiency, low driving voltage, and long life by including the compound in one or more organic layers.

Description

Technical Field

[0001] The present invention relates to a novel organic compound and an organic electroluminescent element using the same, and more particularly to a novel compound having excellent thermal stability and luminescence ability and an organic electroluminescent element having improved characteristics such as luminescence efficiency, driving voltage, and life by including the compound in one or more organic layers. Background Art

[0002] Starting from Bernanose's observation of organic thin film luminescence in the 1950s, research on organic electroluminescent devices developed from the blue electroluminescence of anthracene single crystals in 1965 was conducted, followed by Tang's proposal of an organic electroluminescent device with a stacked structure of two functional layers, a hole layer and a light-emitting layer, in 1987. Later, in order to manufacture high-efficiency and long-life organic electroluminescent devices, a form of introducing various characteristic organic layers into the device was developed, and then the development of special materials for this purpose was carried out.

[0003] When voltage is applied between two electrodes of an organic electroluminescent element, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons transition to the ground state, light is emitted. At this time, the substances used for the organic layer can be divided into luminescent substances, hole injection substances, hole transport substances, electron transport substances, electron injection substances, etc. according to their functions.

[0004] The light-emitting layer materials of organic electroluminescent elements can be divided into blue, green, and red light-emitting materials according to the light-emitting color. In addition, yellow and orange light-emitting materials are also used as light-emitting materials for presenting more natural colors. In addition, in order to increase the luminous efficiency by increasing the color purity and energy transfer, a host / dopant system can be used as a light-emitting material. The above-mentioned dopant substances can be divided into fluorescent dopants using organic substances and phosphorescent dopants using metal coordination compounds containing heavy atoms such as Ir and Pt. Since the development of such phosphorescent materials can theoretically increase the luminous efficiency by up to 4 times compared with fluorescence, not only phosphorescent dopants, but also phosphorescent host materials have received attention. So far, as the substances used in the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, NPB, BCP, Alq3, etc. are widely known, and as light-emitting substances, anthracene derivatives have been reported as fluorescent dopants / host materials. In particular, as phosphorescent materials with great advantages in improving efficiency among luminescent materials, metal coordination compounds containing Ir such as Firpic, Ir(ppy)3, (acac)Ir(btp)2, etc. have been used as blue, green, and red dopant materials. Currently, CBP shows excellent characteristics as a phosphorescent host material.

[0005] However, although conventional luminescent materials have advantages in luminescent properties, they have low glass transition temperatures and very poor thermal stability, and therefore cannot achieve satisfactory lifespans for organic electroluminescent elements. Therefore, there is a demand for the development of luminescent materials with excellent performance.

[0006] On the other hand, the natural existence ratio of deuterium is about 0.015%. Deuterated compounds with abundant deuterium concentration are well known. Deuterated aromatic compounds have been used to study chemical reactions and metabolic pathways, and have also been used as raw materials for medicine, agricultural chemicals, functional substances and analytical tracers. It has also been reported that some deuterated electroluminescent materials show higher performance (efficiency, life) compared with non-deuterated isotopes (for example, with reference to Tong et al. J. Phys. Chem. C 2007, 111, 3490-4). At present, as a method for synthesizing deuterated compounds, multiple treatments must be performed to achieve a high level of deuteration. Such methods are expensive or time-consuming, so they are not suitable in terms of cost and efficiency. Therefore, there is a continuous need for improved manufacturing methods for synthesizing deuterated aromatic compounds. Summary of the invention

[0007] Technical issues

[0008] The present invention is proposed to solve the above-mentioned problems. More specifically, its technical problem is to provide a new organic compound that can be applied to organic electroluminescent elements and has excellent thermal stability and luminescence ability, hole injection ability, hole transport ability, luminescence ability, electron transport ability, electron injection ability, etc., preferably a blue fluorescent light-emitting layer material with excellent thermal stability and luminescence ability.

[0009] Another technical object of the present invention is to provide an organic electroluminescent device which contains the novel organic compound and exhibits thermal stability, low driving voltage, high luminous efficiency, and improved life.

[0010] Other objects and advantages of the present invention will be further clarified by the following detailed description of the invention and the scope of the claims.

[0011] Solution to the problem

[0012] In order to achieve the above object, the present invention provides a compound represented by the following Chemical Formula 1.

[0013] [Chemical formula 1]

[0014]

[0015] In the above chemical formula 1,

[0016] R1 to R8 are the same as or different from each other and are independently hydrogen or deuterium, wherein at least one of R1 to R8 is deuterium,

[0017] X is O, S or CR a R b ,

[0018] R a and R b are the same or different from each other, and are independently C1 to C 40 Alkyl or C6~C 60 The aromatic groups are combined to form a condensed ring,

[0019] R9 to R 14 are the same as or different from each other and are independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C1~C 40 Phosphine, C1~C 40 The phosphine oxide group, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 A group consisting of arylamine groups,

[0020] L is a single bond or selected from C6~C 18 and a heteroarylene group having an atomic nucleus number of 5 to 18,

[0021] n is an integer from 0 to 2,

[0022] A1 is a substituent represented by the following chemical formula 2,

[0023] [Chemical formula 2]

[0024]

[0025] In the above chemical formula 2,

[0026] R 17 To R 24 Any one of them is connected to Chemical Formula 1, and any one of the others is connected to an aryl group (A2) having at least one deuterium,

[0027] Wherein, the above chemical formula 1 and the above aromatic group (A2) having deuterium are connected at the ortho position,

[0028] R not connected to the above chemical formula 1 and the above aromatic group having deuterium 17 To R 24 are the same as or different from each other and are independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C1~C40 Phosphine, C1~C 40 The phosphine oxide group, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 A group consisting of arylamine groups,

[0029] The arylene group and heteroarylene group of the above L and the above R9 to R 14 , R a , R b , R not connected to the above chemical formula 1 and the aromatic group (A2) having deuterium 17 To R 24 The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamine, alkylsilyl, alkylboryl, arylboryl, phosphino, phosphine oxide and arylamine groups in the alkyl group may be independently selected from hydrogen, deuterium (D), halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 The amino group may be substituted with one or more substituents selected from the group consisting of the arylamine group. In this case, when there are multiple substituents, they may be the same as or different from each other.

[0030] In addition, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, wherein at least one of the one or more organic layers comprises the compound represented by Chemical Formula 1.

[0031] Among them, at least one layer of the organic layer containing the compound represented by Chemical Formula 1 can be selected from the group consisting of a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent layer, an electron transport layer and an electron injection layer, and is preferably a luminescent layer. In this case, the compound represented by Chemical Formula 1 can be used as a blue fluorescent host material of the luminescent layer.

[0032] Effects of the Invention

[0033] According to an embodiment of the present invention, the compound represented by the above Chemical Formula 1 has excellent thermal stability and luminescent properties, and thus can be used as a material for an organic layer of an organic electroluminescent element.

[0034] In particular, when the compound represented by Chemical Formula 1 of the present invention is used as a fluorescent host material, an organic electroluminescent element having low voltage, high efficiency and long life characteristics can be manufactured compared to previous host materials, and further a full-color display panel with improved performance and life can be manufactured.

[0035] The effects of the present invention are not limited to the above-exemplified contents, and this specification includes more various effects. DETAILED DESCRIPTION

[0036] Hereinafter, the present invention will be described in detail.

[0037] <Organic compounds>

[0038] The present invention intends to provide a deuterated electroluminescent material having a novel structure capable of simultaneously achieving low voltage, high efficiency and long life characteristics of a device.

[0039] The compound represented by Chemical Formula 1 of the present invention has the following basic skeleton structure: while having a deuterated anthracene portion and a non-deuterated naphthalene (e.g., A1) portion as a core, another deuterated aryl group (e.g., A2) is substituted at the ortho position of the above-mentioned naphthyl (A1), and one phenyl ring of the above-mentioned deuterated anthracene is directly connected to the dibenzoyl portion (e.g., containing an X ring) or connected through an independent connecting group (e.g., L).

[0040] Specifically, the anthracene nucleus of the compound of the chemical formula 1 is substituted with deuterium, so the life characteristics of the device can be improved, and the voltage and efficiency characteristics of the device can be further improved by introducing a naphthyl group (A1) with high carrier mobility into the deuterated anthracene nucleus. When the naphthyl group is substituted with deuterium, according to the Marcus theory, the bond dissociation energy (bond dissociation energy) increases, so the stability of the device is improved compared to the material containing the naphthyl group not substituted with deuterium, and the life characteristics can be further improved.

[0041] In particular, in the present invention, a deuterated aryl group (A2) is introduced into the naphthyl group (A1) in order to improve the lifespan, and two deuterated moieties, such as deuterated anthracene, are combined with the deuterated aryl group (A2) in an ortho-position based on the naphthyl group (A1) in order to provide a steric effect. The introduction of the adjacent binding position of the deuterated aryl group (A2) in this way blocks the packing between molecules, thereby being able to show an efficiency improvement effect. In addition, by introducing a dibenzo-based moiety, particularly a dibenzofuranyl group, which is well known as a blue fluorescent material, the blue fluorescent properties can be maximized.

[0042] In addition, in the present invention, since a plurality of deuterium atoms are contained in the basic skeleton structure, the color purity can be further maximized compared to a compound of the same structure not containing deuterium, and the lifetime characteristics can be significantly improved by further strengthening the weakened intramolecular bonding force between carbon and hydrogen.

[0043] Furthermore, the red and green light-emitting layers of the organic electroluminescent element respectively utilize phosphorescent materials, and their current technical maturity is in a high state. In contrast, the blue light-emitting layer has fluorescent materials and phosphorescent materials, among which the fluorescent material is in a state where performance needs to be improved, and the blue phosphorescent material is still under development, so it is a state with high barriers to entry. That is, the development possibility of the blue light-emitting layer is high, but the technical difficulty is relatively large, so there are limitations in improving the performance (e.g., driving voltage, efficiency, life, etc.) of the blue organic light-emitting element with a blue light-emitting layer. Under the above viewpoint, the compound of Chemical Formula 1 of the present invention can be effectively used as a blue fluorescent light-emitting layer material, and therefore has the advantages of being able to simultaneously improve the performance of the blue light-emitting layer and the low voltage, high efficiency and long life characteristics of the organic electroluminescent element having it.

[0044] Due to the above reasons, the compound represented by the above chemical formula 1 can improve the electron injection / transport capability, luminous efficiency, driving voltage, life characteristics, etc. while improving the luminescent characteristics of the organic electroluminescent element. Therefore, the compound of the chemical formula 1 of the present invention can be used as a material of any one of the organic layer, i.e., hole injection layer, hole transport layer, luminescent layer, electron transport layer and electron injection layer of the organic electroluminescent element, and preferably can be used as a luminescent layer material (blue fluorescent host material). In particular, when the compound represented by the chemical formula 1 of the present invention is used as a blue fluorescent host material, compared with the previous luminescent host material (e.g., CBP), an organic electroluminescent element with low driving voltage, high efficiency and long life can be manufactured, and then a full-color display panel with improved high efficiency and long life characteristics can also be manufactured.

[0045] Specifically, the compound represented by Chemical Formula 1 of the present invention has the following basic skeleton structure: while having a deuterated anthracene portion and a non-deuterated naphthalene (e.g., A1) portion as a core, the ortho position of the naphthyl (A1) is substituted with another deuterated aryl group (e.g., A2), and one phenyl ring of the deuterated anthracene is directly connected to the dibenzoyl portion (e.g., containing an X ring) or connected through an independent connecting group (e.g., L).

[0046] The anthracene contains at least one deuterium (D). According to one embodiment of anthracene, R1 to R8 are the same or different from each other and are independently hydrogen or deuterium, wherein at least one of R1 to R8 is deuterium. Specifically, at least one of R1 to R8 may be deuterium, and the rest may be hydrogen, and more specifically, all of R1 to R8 may be deuterium. By containing a plurality of deuteriums in this way, the life characteristics of the element can be improved.

[0047] A non-deuterated naphthyl (A1) portion having excellent carrier properties is connected to the deuterated anthracene, and a deuterated aryl (A2) is connected to a specific position of the above-mentioned naphthalene (A1) group. Specifically, the deuterated anthracene and the deuterated aryl (A2) are bonded to each other in an ortho position relative to the carbon of the naphthyl (A1). In this way, the two deuterated portions [anthracene, aryl (A2)] bonded in an ortho position with the naphthyl (A1) as the center can simultaneously improve the voltage characteristics and efficiency characteristics of the element through the steric hindrance effect and the intermolecular stacking prevention effect.

[0048] The naphthyl group (A1) can be represented by the following Chemical Formula 2.

[0049] [Chemical formula 2]

[0050]

[0051] R in the above chemical formula 2 17 To R 24 In the formula, the two binding positions to the chemical formula 1 and the deuterated aryl group (A2) are not particularly limited as long as they are ortho positions. 17 To R 24 Any one of the above is connected to the chemical formula 1, and any one of the remaining is connected to the aryl group (A2) having at least one deuterium, wherein the above chemical formula 1 is connected to the above aryl group (A2) having deuterium at the ortho position. Specifically, R of the above chemical formula 2 17 and R 18 One of them may be connected to the chemical formula 1, and the other may be connected to the aryl group (A2) having at least one deuterium. That is, in the substituent represented by the chemical formula 2, R 17 and R 18 Any one of them is connected to the chemical formula 1, R17 and R 18 The other one of them is connected to the deuterium-containing aryl group (A2).

[0052] In addition, R not respectively connected to the chemical formula 1 and the aromatic group (A2) having deuterium 17 To R 24 The same or different from each other, each independently can be selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C1~C 40 Phosphine, C1~C 40 The phosphine oxide group, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 Specifically, R9 to R1 that are not respectively connected to the chemical formula 1 and the aryl group (A2) having deuterium 14 The same or different from each other, each independently can be selected from hydrogen, deuterium, C1~C 40 Alkyl and C6~C 60 A group composed of aromatic groups.

[0053] The deuterated aryl group (A2) introduced into the naphthyl group (A1) of Chemical Formula 2 may be a C6-C8 aryl group known in the art substituted with at least one deuterium (D). 60 There is no particular limitation on the aryl group. 12 of phenyl or naphthyl.

[0054] According to a specific example, the deuterated aryl group (A2) can be selected from the structural formulas represented by the following chemical formulas 3a to 3c, but is not particularly limited thereto.

[0055] [Chemical formula 3a]

[0056]

[0057] [Chemical formula 3b]

[0058]

[0059] [Chemical formula 3c]

[0060]

[0061] In the above chemical formulas 3a to 3c,

[0062] * means the part that forms a bond with chemical formula 2.

[0063] a is an integer of 0-5, and b is an integer of 0-7.

[0064] Such an aryl group (A2) having deuterium can be specifically represented by the following structural formula, but is not particularly limited thereto.

[0065]

[0066] As a specific example of the part of Chemical Formula 2 (naphthyl group, A1) into which the aryl group (A2) having deuterium is introduced according to one embodiment of the present invention, it can be represented by the following structural formula.

[0067]

[0068] In this case, although not shown in the above structural formula, it may be substituted with at least one substituent known in the art (for example, the same as the definition of R9).

[0069] The deuterated anthracene of the present invention is directly bonded to a dibenzo moiety (e.g., containing an X ring) or introduced into the dibenzo moiety (e.g., containing an X ring) through an independent linking group (e.g., L). The above-mentioned dibenzo moiety (e.g., containing an X ring) is excellent in terms of high glass transition temperature (Tg) and thermal stability. As an example of such a dibenzo moiety (e.g., containing an X ring), Y is O, S or CR a R b , specifically O (dibenzofuran) or S (dibenzothiophene), preferably O.

[0070] Among them, R a and R b are the same or different from each other, and are independently C1 to C 40 Alkyl or C6~C 60 The aromatic groups may be combined to form a condensed ring (eg, a spiro ring).

[0071] In addition, the dibenzoyl moiety may be substituted with various substituents R9 to R 16 . Such R9 to R 16 are the same as or different from each other and are independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C1~C 40 Phosphine, C1~C 40 The phosphine oxide group, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 The arylamine group may be composed of a group of arylamine groups, or may be combined with adjacent groups (for example, R 13 To R 16 Specifically, R9 to R 16 The same or different from each other, each independently selected from hydrogen, deuterium, C1-C 40 Alkyl and C6~C 60 wherein R9 to R 16 At least one of, specifically R 13 To R 16 At least one of them can be C6~C 60 or a C6-C 60 The aromatic group.

[0072] The dibenzoyl moiety (e.g., containing an X ring) is directly bonded to the deuterated anthracene or bonded via a linking group (L). In this way, when there is an independent linking group between the dibenzoyl moiety and the deuterated anthracene, the HOMO region can be expanded to facilitate the HOMO-LUMO distribution, and the charge transfer efficiency can be improved by appropriate overlap of HOMO-LUMO.

[0073] Such a linking group (e.g., L) is not particularly limited and may be a single bond or a commonly used divalent linking group (Linker) known in the art. Specifically, L is the same or different from each other and each independently may be a single bond (e.g., direct bonding) or a group selected from C6 to C 18The group consisting of an arylene group having an atomic nucleus number of 5 to 18 and a heteroarylene group having an atomic nucleus number of 5 to 18. Specific examples of the arylene group and the heteroarylene group include phenylene, biphenylene, pyrrolylene, imidazolylene, More specifically, L is the same or different from each other, and each L is independently a single bond or a C6 to C 12 A group consisting of an arylene group having 5 to 12 atomic nuclei and a heteroarylene group having 5 to 12 atomic nuclei.

[0074] In this case, the number of linking groups (e.g., n) may be an integer from 0 to 2. For example, when n is 0, L may be a single bond. In addition, when n is greater than 0 and equal to or less than 2, L may be a substituent remaining in the definition of the linking group except for the single bond.

[0075] According to a specific example, L can be a single bond or a connecting group selected from the following structural formulas.

[0076]

[0077] In the above structural formula,

[0078] * means a part that forms a bond with the above chemical formula 1. In addition, although not shown in the above structural formula, it may be substituted with at least one substituent known in the art (for example, the same as the definition of R9).

[0079] In the above chemical formula 1, the arylene group and heteroarylene group of L and the above R9 to R 14 , R a , R b , R not connected to the above chemical formula 1 and the aromatic group (A2) having deuterium 17 To R 24 The alkyl, alkenyl, alkynyl, aryl, heteroaryl, aryloxy, alkoxy, cycloalkyl, heterocycloalkyl, arylamine, alkylsilyl, alkylboryl, arylboryl, phosphino, phosphine oxide and arylamine groups in the alkyl group may be independently selected from hydrogen, deuterium (D), halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 The amino group may be substituted with one or more substituents selected from the group consisting of the arylamine groups. In this case, when there are multiple substituents, they may be the same as or different from each other.

[0080] According to an embodiment of the present invention, the compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 4 to 9 according to the types of the naphthyl group (A1) and the deuterated aryl group (A2) of Chemical Formula 2.

[0081] [Chemical formula 4]

[0082]

[0083] [Chemical formula 5]

[0084]

[0085] [Chemical formula 6]

[0086]

[0087] [Chemical formula 7]

[0088]

[0089] [Chemical formula 8]

[0090]

[0091] [Chemical formula 9]

[0092]

[0093] In the above chemical formulas 4 to 9,

[0094] X, L, R1 to R 16 , R 19 To R 24 , n, a and b are each the same as defined in Chemical Formula 1.

[0095] The compounds represented by the above Chemical Formulae 4 to 9 may be further embodied as any one of the following Chemical Formulae 4a to 9a.

[0096] [Chemical formula 4a]

[0097]

[0098] [Chemical Formula 5a]

[0099]

[0100] [Chemical formula 6a]

[0101]

[0102] [Chemical Formula 7a]

[0103]

[0104] [Chemical formula 8a]

[0105]

[0106] [Chemical Formula 9a]

[0107]

[0108] According to another embodiment of the present invention, the compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 10 to 13 according to the binding position of the dibenzoyl moiety (eg, X-containing ring).

[0109] [Chemical formula 10]

[0110]

[0111] [Chemical formula 11]

[0112]

[0113] [Chemical formula 12]

[0114]

[0115] [Chemical formula 13]

[0116]

[0117] In the above chemical formulas 10 to 13,

[0118] A1, X, L, R1 to R 16 , R 19 To R 24 , n, a and b are each the same as defined in Chemical Formula 1.

[0119] According to yet another embodiment of the present invention, the compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 14 to 16 depending on the type of the dibenzoyl moiety (eg, X-containing ring).

[0120] [Chemical formula 14]

[0121]

[0122] [Chemical formula 15]

[0123]

[0124] [Chemical formula 16]

[0125]

[0126] In the above chemical formulas 14 to 16,

[0127] A1, X, L, R1 to R 16 , R 19 To R 24 , Ra, Rb and n are each the same as defined in Chemical Formula 1.

[0128] According to another embodiment of the present invention, the compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 17 or 18 depending on the type of substituent introduced into the dibenzoyl moiety (eg, X-containing ring).

[0129] [Chemical formula 17]

[0130]

[0131] [Chemical formula 18]

[0132]

[0133] In the above chemical formula 17 or 18,

[0134] A1, X, L, R1 to R 12 and n are each the same as defined in Chemical Formula 1.

[0135] The compound represented by the above-described Chemical Formula 1 of the present invention can be further embodied as a compound represented by any one of the following compounds 1 to 64. However, the compound represented by the Chemical Formula 1 of the present invention is not limited to the compounds exemplified below.

[0136]

[0137]

[0138]

[0139] In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples of such alkyl groups include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, and hexyl.

[0140] In the present invention, "alkenyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples of such alkenyl groups include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

[0141] In the present invention, "alkynyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples of such alkynyl groups include, but are not limited to, ethynyl and 2-propynyl.

[0142] In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0143] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclei, wherein one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted with heteroatoms such as N, O, S or Se. Examples of such heterocycloalkyl include morpholinyl and piperazinyl, but are not limited thereto.

[0144] In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms and composed of a single ring or a combination of two or more rings. In addition, it may also include a form in which two or more rings are simply attached (pendant) or condensed to each other. Examples of such aryl groups include, but are not limited to, phenyl, naphthyl, phenanthrenyl, anthracenyl, etc.

[0145] In the present invention, "heteroaryl" means a monovalent substituent derived from a monocyclic heterocyclic or polycyclic aromatic hydrocarbon having 5 to 60 atomic nuclei. In this case, one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted by heteroatoms such as N, O, S or Se. In addition, it may also include a form in which two or more rings are simply attached (pendant) or condensed to each other, and further may include a form condensed with an aromatic group. Examples of such heteroaryl groups include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazole, 2-isothiazolyl, and 2-isothiazolyl. oxazolyl, 2-pyridyl, 2-pyrimidinyl, etc., but are not limited thereto.

[0146] In the present invention, "alkoxy" means a monovalent substituent represented by R'O-, wherein R' is an alkyl group having 1 to 40 carbon atoms. Such an alkoxy group may include a linear, branched or cyclic structure. Examples of such an alkoxy group include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, pentoxy, and the like.

[0147] In the present invention, "aryloxy" means a monovalent substituent represented by RO-, wherein R is an aryl group having 6 to 60 carbon atoms. Examples of such aryloxy groups include, but are not limited to, phenoxy, naphthoxy, and diphenoxy.

[0148] In the present invention, an "alkylsilyl group" means a silyl group substituted by an alkyl group having 1 to 40 carbon atoms, and an "arylsilyl group" means a silyl group substituted by an aryl group having 6 to 60 carbon atoms.

[0149] In the present invention, the "alkylboryl group" means a boron group substituted by an alkyl group having 1 to 40 carbon atoms, and the "arylboryl group" means a boron group substituted by an aryl group having 6 to 60 carbon atoms.

[0150] In the present invention, the "arylphosphino group" means a phosphino group substituted with an aryl group having 6 to 60 carbon atoms, and the "arylphosphine oxide group" means a group containing O in the phosphino group substituted with an aryl group having 6 to 60 carbon atoms.

[0151] In the present invention, the "condensed ring" means a condensed aliphatic ring, a condensed aromatic ring, a condensed aliphatic heterocycle, a condensed aromatic heterocycle or a combination thereof.

[0152] In the present invention, the "arylamino group" means an amine group substituted with an aryl group having 6 to 60 carbon atoms.

[0153] The compound represented by Chemical Formula 1 of the present invention can be prepared without limitation according to methods known in the art. For example, various syntheses can be performed with reference to the synthesis processes of the following examples.

[0154] <Organic electroluminescent element>

[0155] The present invention provides an organic electroluminescent device comprising the compound represented by the above Chemical Formula 1.

[0156] More specifically, the organic electroluminescent element of the present invention comprises an anode, a cathode, and one or more organic layers between the anode and the cathode, and at least one of the one or more organic layers comprises the compound represented by the above chemical formula 1. In this case, the above compounds can be used alone or in combination of two or more.

[0157] The one or more organic layers may include one or more of a hole injection layer, a hole transport layer, a light-assisting layer, a light-emitting layer, an electron transport layer, and an electron injection layer, wherein at least one organic layer may include the compound represented by the above chemical formula 1. Specifically, the organic layer including the compound of the above chemical formula 1 may be a light-emitting layer, more specifically, may be a blue fluorescent light-emitting layer material.

[0158] On the one hand, in the light-emitting layer of the organic electroluminescent element, with respect to the main substance, the triplet energy gap of the main body should be higher than that of the dopant. That is, in order to effectively provide phosphorescent luminescence from the dopant, the lowest excited state of the main body should have a higher energy than the lowest emission state of the dopant. The compound represented by the above chemical formula 1 has a high triplet energy, and the energy level can be adjusted to be higher than that of the dopant, so it can be used as a main substance. Such a compound represented by chemical formula 1 can prevent the excitons generated in the light-emitting layer from diffusing to the electron transport layer or the hole transport layer adjacent to the light-emitting layer. Therefore, the luminous efficiency of the element can be improved by increasing the number of excitons that contribute to luminescence in the light-emitting layer, and the durability and stability of the element can be improved, so that the life of the element is also effectively improved.

[0159] The light-emitting layer of the organic electroluminescent element of the present invention comprises a host material and a dopant material, and in this case, the compound of the above chemical formula 1 can be used as a fluorescent host material. In addition to the host material of the above chemical formula 1, the above light-emitting layer can contain a common host and / or dopant known in the art without limitation. Their content ratio (mixing ratio) is not particularly limited and can be appropriately adjusted within the content range known in the art.

[0160] The structure of the organic electroluminescent element of the present invention is not particularly limited. As a non-limiting example, it can be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent layer, an electron transport layer, an electron injection layer and a cathode are stacked in sequence. At this time, one or more of the hole injection layer, the hole transport layer, the luminescence auxiliary layer, the luminescent layer, the electron transport layer and the electron injection layer may contain the compound represented by the above chemical formula 1, and preferably the luminescent layer may contain the compound represented by the above chemical formula 1. In addition, the structure of the organic electroluminescent element of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer.

[0161] On the other hand, the organic electroluminescent element of the present invention can be formed and manufactured by 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.

[0162] The organic layer may be formed by vacuum deposition or solution coating, and examples of the solution coating include spin coating, dip coating, blade coating, inkjet printing, thermal transfer, etc., but are not limited thereto.

[0163] The substrate used in producing the organic electroluminescent element of the present invention is not particularly limited, and a silicon wafer, quartz, a glass plate, a metal plate, a plastic film or sheet, etc. can be used.

[0164] In addition, examples of anode materials include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited to these.

[0165] In addition, cathode materials include, but are not limited to: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead, or alloys thereof; and multilayer structure materials such as LiF / Al or LiO2 / Al.

[0166] In addition, the hole injection layer, the hole transport layer, the electron injection layer, and the electron transport layer are not particularly limited, and common materials known in the art can be used.

[0167] Hereinafter, the present invention will be described in detail by way of examples, which are as follows. However, the following examples are merely illustrative of the present invention, and the present invention is not limited to the following examples.

[0168] Preparation Example

[0169] [Preparation Example 1] Synthesis of Core 1

[0170] <Step 1> Synthesis of Core 1-1

[0171]

[0172] (1-Chloronaphthalene-2-yl)boric acid (41 g, 200 mmol), 1-bromobenzene-2,3,4,5,6-d5 (32 g, 200 mmol), Pd(PPh3)4 (9 g, 8 mmol), and NaOH (24 g, 600 mmol) were added to 1,000 ml of THF and 500 ml of H2O, and stirred at 80°C for 8 hours. After the reaction, 500 ml of water was added and stirred. After the reaction, the organic layer was separated by extraction and concentrated. The concentrated organic layer was dissolved in toluene, filtered through silica gel, and recrystallized with ethanol to obtain the target compound core 1-1 (42 g, yield 88%).

[0173] 1 H-NMR: δ7.51(t,1H),7.59(t,1H),7.62(d,1H),7.88(d,1H),8.24(d,1H),8.25(d,1H)

[0174] <Step 2> Synthesis of Core 1-2

[0175]

[0176] Core 1-1 (37 g, 150 mmol), (anthraquinone-9-yl-d9) boronic acid (35 g, 150 mmol), Pd(PPh3)4 (7 g, 6 mmol), and NaOH (18 g, 450 mmol) were added to 500 ml of THF and 250 ml of H2O, and stirred at 80°C for 8 hours. After the reaction, 200 ml of water was added and stirred. After the reaction, the organic layer was separated by extraction and concentrated. The concentrated organic layer was dissolved in toluene, filtered on silica gel, and recrystallized with ethanol to obtain the target compound Core 1-2 (47 g, yield 79%).

[0177] 1 H-NMR: δ7.40(t,1H),7.54(t,1H),7.72(d,1H),8.26(d,1H),8.31(d,1H),8.93(d,1H)

[0178] <Step 3> Synthesis of Core 1

[0179]

[0180] Core 1-2 (39 g, 100 mmol) and N-bromosuccinimide (18 g, 100 mmol) were dissolved in 400 ml of dimethylformamide and stirred at room temperature for 4 hours. After the reaction was completed, 400 ml of water was added and the generated solid was filtered. The filtered solid was dissolved in dichloromethane and filtered through silica gel. The organic solvent was concentrated and recrystallized with ethanol to obtain the target compound core 1 (40 g, yield 93%).

[0181] 1 H-NMR: δ7.40(t,1H),7.54(t,1H),7.72(d,1H),8.26(d,1H),8.31(d,1H),8.93(d,1H)

[0182] [Preparation Example 2] Synthesis of Core 2

[0183] <Step 1> Synthesis of Core 2-1

[0184]

[0185] (2-Chloronaphthalene-1-yl)boric acid (41 g, 200 mmol), 1-bromobenzene-2,3,4,5,6-d5 (32 g, 200 mmol), Pd(PPh3)4 (9 g, 8 mmol), and NaOH (24 g, 600 mmol) were added to 1,000 ml of THF and 500 ml of H2O, and stirred at 80°C for 8 hours. After the reaction, 500 ml of water was added and stirred. After the reaction, the organic layer was separated by extraction and concentrated. The concentrated organic layer was dissolved in toluene, filtered through silica gel, and recrystallized with ethanol to obtain the target compound core 2-1 (41 g, yield 85%).

[0186] 1 H-NMR: δ7.34(t,1H),7.44(d,2H),7.49(t,1H),7.98(d,1H),8.10(d,1H),8.94(d,1H)

[0187] <Step 2> Synthesis of Core 2-2

[0188]

[0189] Core 2-1 (37 g, 150 mmol), (anthraquinone-9-yl-d9) boronic acid (35 g, 150 mmol), Pd(PPh3)4 (7 g, 6 mmol), and NaOH (18 g, 450 mmol) were added to 500 ml of THF and 250 ml of H2O, and stirred at 80°C for 8 hours. After the reaction, 200 ml of water was added and stirred. After the reaction, the organic layer was separated by extraction and concentrated. The concentrated organic layer was dissolved in toluene, filtered on silica gel, and recrystallized with ethanol to obtain the target compound core 2-2 (45 g, yield 76%).

[0190] 1 H-NMR: δ7.40(t,1H),7.54(t,1H),7.72(d,1H),8.26(d,1H),8.31(d,1H),8.93(d,1H)

[0191] <Step 3> Synthesis of Core 2

[0192]

[0193] Core 2-2 (39 g, 100 mmol) and N-bromosuccinimide (18 g, 100 mmol) were dissolved in 400 ml of dimethylformamide and stirred at room temperature for 4 hours. After the reaction was completed, 400 ml of water was added and the generated solid was filtered. The filtered solid was dissolved in dichloromethane and filtered through silica gel. The organic solvent was concentrated and recrystallized with ethanol to obtain the target compound core 2 (41 g, yield 96%).

[0194] 1 H-NMR: δ7.40(t,1H),7.54(t,1H),7.72(d,1H),8.26(d,1H),8.31(d,1H),8.93(d,1H)

[0195] [Preparation Example 3] Synthesis of Core 3

[0196] <Step 1> Synthesis of Core 3-1

[0197]

[0198] (2-Chloronaphthalene-1-yl)boric acid (41 g, 200 mmol) and 2-bromonaphthalene-1,3,4,5,6,7,8-d7 (43 g, 200 mmol) as well as Pd(PPh3)4 (9 g, 8 mmol) and NaOH (24 g, 600 mmol) were added to 1,000 ml of THF and 500 ml of H2O and stirred at 80°C for 8 hours. After the reaction was completed, 500 ml of water was added and stirred. After the reaction was completed, the organic layer was separated by extraction and concentrated. The concentrated organic layer was dissolved in toluene, filtered through silica gel and recrystallized with ethanol to obtain the target compound core 3-1 (50 g, yield 85%).

[0199] 1 H-NMR: δ7.34(t,1H),7.44(d,2H),7.49(t,1H),7.98(d,1H),8.10(d,1H),8.94(d,1H)

[0200] <Step 2> Synthesis of Core 3-2

[0201]

[0202] Core 3-1 (44 g, 150 mmol), (anthraquinone-9-yl-d9) boronic acid (35 g, 150 mmol), Pd(PPh3)4 (7 g, 6 mmol), and NaOH (18 g, 450 mmol) were added to 500 ml of THF and 250 ml of H2O, and stirred at 80°C for 8 hours. After the reaction, 200 ml of water was added and stirred. After the reaction, the organic layer was separated by extraction and concentrated. The concentrated organic layer was dissolved in toluene, filtered on silica gel, and recrystallized with ethanol to obtain the target compound core 3-2 (50 g, yield 75%).

[0203] 1 H-NMR: δ7.40(t,1H),7.54(t,2H),7.72(d,1H),8.26(d,1H),7.31(d,1H),8.93(d,1H)

[0204] <Step 3> Synthesis of Core 3

[0205]

[0206] Core 3-2 (45 g, 100 mmol) and N-bromosuccinimide (18 g, 100 mmol) were dissolved in 400 ml of dimethylformamide and stirred at room temperature for 4 hours. After the reaction was completed, 400 ml of water was added and the generated solid was filtered. The filtered solid was dissolved in dichloromethane and filtered through silica gel. The organic solvent was concentrated and recrystallized with ethanol to obtain the target compound core 3 (47 g, yield 89%).

[0207] 1 H-NMR: δ7.40(t,1H),7.54(t,2H),7.72(d,1H),8.26(d,1H),7.31(d,1H),8.93(d,1H)

[0208] [Preparation Example 4] Synthesis of Core 4

[0209] <Step 1> Synthesis of Core 4-1

[0210]

[0211] (1-Chloronaphthalene-2-yl)boric acid (37 g, 150 mmol) and 2-bromonaphthalene-1,3,4,5,6,7,8-d7 (43 g, 200 mmol) as well as Pd(PPh3)4 (7 g, 6 mmol) and NaOH (18 g, 450 mmol) were added to 500 ml of THF and 250 ml of H2O and stirred at 80°C for 8 hours. After the reaction was completed, 500 ml of water was added and stirred. After the reaction was completed, the organic layer was separated by extraction and concentrated. The concentrated organic layer was dissolved in toluene, filtered through silica gel and recrystallized with ethanol to obtain the target compound core 4-1 (50 g, yield 85%).

[0212] 1 H-NMR: δ7.51(t,1H),7.59(t,1H),7.62(d,1H),7.88(d,1H),8.24(d,1H),8.25(d,1H)

[0213] <Step 2> Synthesis of Core 4-2

[0214]

[0215] Core 4-1 (44 g, 150 mmol), (anthraquinone-9-yl-d9) boronic acid (35 g, 150 mmol), Pd(PPh3)4 (7 g, 6 mmol), and NaOH (18 g, 450 mmol) were added to 500 ml of THF and 250 ml of H2O, and stirred at 80°C for 8 hours. After the reaction, 200 ml of water was added and stirred. After the reaction, the organic layer was separated by extraction and concentrated. The concentrated organic layer was dissolved in toluene, filtered on silica gel, and recrystallized with ethanol to obtain the target compound core 4-2 (50 g, yield 74%).

[0216] 1 H-NMR: δ7.40(t,1H),7.54(t,2H),7.72(d,1H),8.26(d,1H),7.31(d,1H),8.93(d,1H)

[0217] <Step 3> Synthesis of Core 4

[0218]

[0219] Core 4-2 (39 g, 100 mmol) and N-bromosuccinimide (18 g, 100 mmol) were dissolved in 400 ml of dimethylformamide and stirred at room temperature for 4 hours. After the reaction was completed, 400 ml of water was added and the generated solid was filtered. The filtered solid was dissolved in dichloromethane and filtered through silica gel. The organic solvent was concentrated and recrystallized with ethanol to obtain the target compound core 4 (47 g, yield 88%).

[0220] 1 H-NMR: δ7.40(t,1H),7.54(t,2H),7.72(d,1H),8.26(d,1H),7.31(d,1H),8.93(d,1H)

[0221] Synthesis example

[0222] [Synthesis Example 1] Synthesis of Compound 2

[0223]

[0224] Core 1 (4.7 g, 10.0 mmol), dibenzo[b,d]furan-2-ylboronic acid (2.1 g, 10.0 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), and NaOH (1.2 g, 30.0 mmol) were added to 50 ml of THF and 25 ml of H2O, and stirred at 80°C for 8 hours. After the reaction was completed, 20 ml of water was added and stirred. The generated solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica gel, and recrystallized with toluene to obtain compound 2 (3.5 g, yield 63%) as the target compound.

[0225] [LCMS]: 559

[0226] [Synthesis Example 2] Synthesis of Compound 3

[0227]

[0228] Core 1 (4.7 g, 10.0 mmol), dibenzo[b,d]furan-1-ylboronic acid (2.1 g, 10.0 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), and NaOH (1.2 g, 30.0 mmol) were added to 50 ml of THF and 25 ml of H2O, and stirred at 80°C for 8 hours. After the reaction was completed, 20 ml of water was added and stirred. The generated solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica gel, and recrystallized with toluene to obtain compound 3 (4.4 g, yield 78%) as the target compound.

[0229] [LCMS]: 559

[0230] [Synthesis Example 3] Synthesis of Compound 6

[0231]

[0232] Core 2 (4.7 g, 10.0 mmol), dibenzo[b,d]furan-1-ylboronic acid (2.1 g, 10.0 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), and NaOH (1.2 g, 30.0 mmol) were added to 50 ml of THF and 25 ml of H2O, and stirred at 80°C for 8 hours. After the reaction was completed, 20 ml of water was added and stirred. The generated solid was filtered. After filtration, the solid was dissolved in toluene, filtered on silica gel, and recrystallized with toluene to obtain compound 6 (4.5 g, yield 79%) as the target compound.

[0233] [LCMS]: 559

[0234] [Synthesis Example 4] Synthesis of Compound 9

[0235]

[0236] Core 3 (5.2 g, 10.0 mmol), dibenzo[b,d]furan-2-ylboronic acid (2.1 g, 10.0 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), and NaOH (1.2 g, 30.0 mmol) were added to 50 ml of THF and 25 ml of H2O, and stirred at 80°C for 8 hours. After the reaction was completed, 20 ml of water was added and stirred. The generated solid was filtered. After filtration, the solid was dissolved in toluene, filtered on silica gel, and recrystallized with toluene to obtain compound 9 (4.7 g, yield 77%) as the target compound.

[0237] [LCMS]: 611

[0238] [Synthesis Example 5] Synthesis of Compound 13

[0239]

[0240] Core 1 (4.7 g, 10.0 mmol), (4-(dibenzo[b,d]furan-1-yl)phenyl)boric acid (2.9 g, 10.0 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), and NaOH (1.2 g, 30.0 mmol) were added to 50 ml of THF and 25 ml of H2O, and stirred at 80°C for 8 hours. After the reaction was completed, 20 ml of water was added and stirred. The generated solid was filtered. After filtration, the solid was dissolved in toluene, filtered on silica gel, and recrystallized with toluene to obtain compound 13 (5.9 g, yield 89%) as the target compound.

[0241] [LCMS]: 635

[0242] [Synthesis Example 6] Synthesis of Compound 14

[0243]

[0244] Core 1 (4.7 g, 10.0 mmol), (3-(dibenzo[b,d]furan-2-yl)phenyl)boric acid (2.9 g, 10.0 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), and NaOH (1.2 g, 30.0 mmol) were added to 50 ml of THF and 25 ml of H2O, and stirred at 80°C for 8 hours. After the reaction was completed, 20 ml of water was added and stirred. The generated solid was filtered. After filtration, the solid was dissolved in toluene, filtered on silica gel, and recrystallized with toluene to obtain compound 14 (4.8 g, yield 75%) as the target compound.

[0245] [LCMS]: 635

[0246] [Synthesis Example 7] Synthesis of Compound 22

[0247]

[0248] Core 1 (4.7 g, 10.0 mmol), (4-(dibenzo[b,d]furan-1-yl)naphthalene-1-yl)boric acid (3.4 g, 10.0 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), and NaOH (1.2 g, 30.0 mmol) were added to 50 ml of THF and 25 ml of H2O, and stirred at 80°C for 8 hours. After the reaction was completed, 20 ml of water was added and stirred. The generated solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica gel, and recrystallized with toluene to obtain compound 22 (5.3 g, yield 77%) as the target compound.

[0249] [LCMS]: 685

[0250] [Synthesis Example 8] Synthesis of Compound 45

[0251]

[0252] Core 1 (4.7 g, 10.0 mmol), (4-phenyldibenzo[b, d]furan-2-yl)boronic acid (2.9 g, 10.0 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), and NaOH (1.2 g, 30.0 mmol) were added to 50 ml of THF and 25 ml of H2O, and stirred at 80°C for 8 hours. After the reaction was completed, 20 ml of water was added and stirred. The generated solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica gel, and recrystallized with toluene to obtain compound 45 (4.9 g, yield 76%) as the target compound.

[0253] [LCMS]: 635

[0254] [Synthesis Example 9] Synthesis of Compound 46

[0255]

[0256] Core 1 (4.7 g, 10.0 mmol), (4-(dibenzo[b,d]furan-1-yl)phenyl)boric acid (2.9 g, 10.0 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), and NaOH (1.2 g, 30.0 mmol) were added to 50 ml of THF and 25 ml of H2O, and stirred at 80°C for 8 hours. After the reaction was completed, 20 ml of water was added and stirred. The generated solid was filtered. After filtration, the solid was dissolved in toluene, filtered on silica gel, and recrystallized with toluene to obtain compound 46 (4.7 g, yield 73%) as the target compound.

[0257] [LCMS]: 635

[0258] [Synthesis Example 10] Synthesis of Compound 51

[0259]

[0260] Core 4 (5.2 g, 10.0 mmol), (6-phenyldibenzo[b,d]furan-2-yl)boronic acid (2.9 g, 10.0 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), and NaOH (1.2 g, 30.0 mmol) were added to 50 ml of THF and 25 ml of H2O, and stirred at 80°C for 8 hours. After the reaction was completed, 20 ml of water was added and stirred. The generated solid was filtered. After filtration, the solid was dissolved in toluene, filtered through silica gel, and recrystallized with toluene to obtain compound 51 (5.9 g, yield 85%) as the target compound.

[0261] [LCMS]: 687

[0262] [Examples 1 to 10] Preparation of blue organic EL elements

[0263] Each compound synthesized in Synthesis Examples 1 to 10 was purified by sublimation to a high purity according to a generally known method, and then a blue organic EL device was produced according to the following process.

[0264] First, we will The glass substrate coated with a thin film of indium tin oxide (ITO) was washed with distilled water ultrasonic. After the distilled water washing, it was ultrasonically cleaned with isopropyl alcohol, acetone, methanol and other solvents and dried, and then transferred to a UV OZONE cleaning machine (Power sonic 405, Hwashintech), and then the substrate was cleaned with UV for 5 minutes, and then the substrate was transferred to a vacuum evaporator.

[0265] On the ITO transparent electrode prepared in this way, an organic electroluminescent element is manufactured by stacking in the order of DS-205 (Doosan Corporation) (80nm) / NPB (15nm) / each compound + ADN + 5% DS-405 (Doosan Corporation) (300nm) / BCP (10nm) / Alq3 (30nm) / LiF (1nm) / Al (200nm).

[0266] For reference, the structures of NPB, ADN, BCP, and compounds A-1 to A-4 used in the examples and comparative examples of the present application are shown below.

[0267]

[0268]

[0269] [Comparative Example 1] Preparation of Blue Organic EL Element

[0270] A blue organic electroluminescent element of Comparative Example 1 was produced in the same manner as in Example 1 except that the compound A-1 was used instead of the compound 2 used in Example 1.

[0271] [Comparative Example 2] Preparation of Blue Organic EL Element

[0272] A blue organic electroluminescent element of Comparative Example 2 was produced in the same manner as in Example 1 except that the compound A-2 was used instead of the compound 2 used in Example 1.

[0273] [Comparative Example 3] Preparation of Blue Organic EL Element

[0274] A blue organic electroluminescent element of Comparative Example 3 was produced in the same manner as in Example 1 except that the compound A-3 was used instead of the compound 2 used in Example 1.

[0275] [Comparative Example 4] Preparation of Blue Organic EL Element

[0276] A blue organic electroluminescent element of Comparative Example 4 was produced in the same manner as in Example 1 except that the compound A-4 was used instead of the compound 2 used in Example 1.

[0277] [Evaluation example]

[0278] For each of the blue organic electroluminescent devices prepared in Examples 1 to 10 and Comparative Examples 1 to 4, the current density of 10 mA / cm 2 The driving voltage, current efficiency and lifespan are shown in Table 1 below.

[0279] [Table 1]

[0280] sample Luminescent layer Driving voltage(V) Current efficiency (cd / A) <![CDATA[Lifetime T 95 (hr)]]> Example 1 2 3.6 9.2 300 Example 2 3 3.4 9.6 330 Example 3 6 3.5 9.2 310 Example 4 9 3.7 8.9 310 Example 5 13 3.2 9.3 305 Example 6 14 3.3 9.1 290 Example 7 22 3.7 9.0 270 Example 8 45 3.8 9.0 300 Example 9 46 3.4 9.7 330 Example 10 51 3.5 8.9 310 Comparative Example 1 A-1 5.0 6.4 100 Comparative Example 2 A-2 4.3 7.0 100 Comparative Example 3 A-3 4.7 7.2 150 Comparative Example 4 A-4 4.8 7.0 180

[0281] As shown in Table 1, the blue organic electroluminescent elements of Examples 1 to 10 using the compound represented by Chemical Formula 1 of the present invention as the luminescent layer material are more excellent in terms of driving voltage, current efficiency and life than the blue organic electroluminescent elements of Comparative Examples 1 and 2 which do not contain deuterium in the molecule and Comparative Examples 3 and 4 which use luminescent layer materials containing anthracene and naphthyl but the naphthyl is substituted at the meta-position and para-position. In particular, it can be confirmed that the effect is about 2 to 3 times more significant in terms of the life characteristics of the element.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, R1 to R8 are the same or different from each other and are independently hydrogen or deuterium, wherein, At least one of R1 to R8 is deuterium, X is O, R9 to R 16 The same or different from each other, each independently selected from hydrogen and C6~C 60 The aromatic group, L is a single bond or C6~C 18 The arylene group, n is an integer from 0 to 2, A1 is any one selected from the group of substituents represented by the following structural formulas, The R9 to R 16 The aryl groups can be independently selected from deuterium (D), C1~C 40 Alkyl and C6~C 60 The aryl group may be substituted by one or more substituents selected from the group consisting of the aryl group. In this case, when there are multiple substituents, they may be the same as or different from each other.

2. The compound according to claim 1, wherein L is a single bond or a substituent group selected from the group represented by the following structural formula: In the structural formula, * means a part that forms a bond with the chemical formula 1.

3. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 10 to 13: [Chemical formula 10] [Chemical formula 11] [Chemical formula 12] [Chemical formula 13] In the chemical formulas 10 to 13, A1, X, L, R1 to R 16 and n are the same as defined in claim 1.

4. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by the following Chemical Formula 14: [Chemical formula 14] In the chemical formula 14, A1, L, R1 to R 16 and n are each the same as defined in claim 1.

5. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by the following Chemical Formula 17 or Chemical Formula 18: [Chemical formula 17] [Chemical formula 18] In the chemical formula 17 or chemical formula 18, A1, X, L, R1 to R 12 and n are each the same as defined in claim 1, and a is an integer of 0-5.

6. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is selected from the group consisting of compounds represented by the following chemical formulas: The compound according to claim 1 , wherein the compound represented by Chemical Formula 1 is a fluorescent host material.

8. An organic electroluminescent element comprising an anode, a cathode and one or more organic layers between the anode and the cathode, At least one of the one or more organic layers comprises the compound according to any one of claims 1 to 7. 9 . The organic electroluminescent element according to claim 8 , wherein the organic layer containing the compound is selected from the group consisting of a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a light-emitting layer, an electron transport layer and an electron injection layer. 10 . The organic electroluminescent device according to claim 9 , wherein the organic layer containing the compound is a fluorescent light-emitting layer.

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