Organic compounds and organic electroluminescent elements using the same

Abstract

This invention provides a novel organic compound that is applicable to organic electroluminescent devices and exhibits excellent hole / electron injection and transport capabilities, as well as luminescence. [Solution] A compound represented by chemical formula 1 is provided. JPEG2026086487000101.jpg69160

Description

[Technical Field]

[0001] This invention relates to a novel organic light-emitting compound and an organic electroluminescent element using the same. For more details, see Compounds with excellent electron transport ability, luminescence ability, and thermal stability, and By incorporating it into one or more organic layers, the characteristics such as luminescence efficiency, driving voltage, and lifespan are improved. Regarding lectroluminescent elements. [Background technology]

[0002] Following Bernanose's discovery of luminescence in organic thin films in the 1950s, 1965 Organic electroluminescent cells that led to blue emission using anthracene single crystals in 2018 Research on electroluminescent elements began in 1987 in Ta An organic electroluminescent material having a laminated structure divided into a hole layer and a light-emitting layer, as described by ng et al. A fluorine element has been proposed. Subsequently, high-efficiency, long-life organic electroluminescent elements have been developed. To obtain the element, developments have progressed to introduce characteristic organic layers within the element. Therefore, specialized materials for use in this purpose are being developed.

[0003] In an organic electroluminescent device, when a voltage is applied between the two electrodes, holes are generated from the anode. However, electrons are injected into the organic layer from the cathode. The injected holes and electrons combine to form excitons. An exciton is formed, and when this exciton returns to the ground state, it emits light. The materials used as material layers are classified according to their function as luminescent materials, hole-injecting materials, and hole-transporting materials. They are classified into substances, electron transport materials, electron injection materials, etc.

[0004] The light-emitting layer forming material for organic electroluminescent elements is classified by light emission color as blue, green, etc. It is classified as a red luminescent material. In addition, to achieve better natural colors, it is used as a luminescent material. Yellow and orange light-emitting materials are sometimes used. In addition, to improve color purity and energy To improve luminescence efficiency through movement, host-dopant type materials are used as luminescent materials. It is used. Dopant substances include fluorescent dopants that use organic materials, and Ir, Pt, etc. Which heavy atoms are used in the phosphorescent dopant metal complex compound? They can be divided into two categories. Such phosphorescent materials theoretically have four times the luminescence efficiency of fluorescence. Improvements have been achieved, and interest is growing not only in the development of phosphorescent dopants but also in the development of phosphorescent host materials. To date, the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer have been NPB, B CP and Alq3 are widely known, and as for luminescent materials, anthracene derivatives are used in fireflies. It has been reported as a photodopant-host material, particularly in terms of improving efficiency among luminescent materials. Phosphorescent materials with significant advantages include Firpic, Ir(ppy)3, (aca c) Metal complex compounds containing Ir, such as Ir(btp)2, produce blue, green, and red colors. It is used as a pant material. Currently, CBP has excellent properties as a phosphorescent host material. This indicates that.

[0005] However, conventional organic layer materials have advantages in terms of luminescence properties, but their glass transition temperature is low. Furthermore, due to its inferior thermal stability, it is not satisfactory in terms of the lifespan of the organic electroluminescent element. This is not the case. Therefore, there is a need for the development of high-performance organic layer materials. [Overview of the Initiative] [Problems that the invention aims to solve]

[0006] The object of the present invention is to provide an organic electroluminescent device that is applicable to holes and electric fields. The objective is to provide novel organic compounds that exhibit excellent molecular injection and transport capabilities, as well as luminescence.

[0007] Another object of the present invention is that, by including the novel organic compounds described above, it is possible to achieve a low drive voltage and high To provide an organic electroluminescent element that exhibits high luminescence efficiency and achieves a long lifespan. It is about that.

[0008] Other objects and advantages of the present invention are described in the detailed description of the invention and the claims below. It is explained very clearly. [Means for solving the problem]

[0009] To achieve the above-mentioned objectives, the present invention provides a compound represented by the following chemical formula 1. ru.

[0010] [ka] (In the above chemical formula 1, Multiple X values ​​may be identical or different from each other, and each can independently be CR2 or N. However, at least two of the multiple X values ​​are N. R2 is hydrogen, deuterium (D), halogen, cyano group, nitro group, C1-C 40 no Arki group, C2~C 40 alkenyl group, C2~C 40 Alkynyl group, C3~C 40 no Shik chloroalkyl groups, heterocycloalkyl groups with 3 to 40 nuclear atoms, C6-C6 60 Ariel Groups, heteroaryl groups with 5 to 60 nuclear atoms, C1 to C 40 alkyloxy group, C6~ C 60 aryl oxy group of C3 - C 40 alkylsilyl group of C6 - C 60 aryl silyl group of C1 - C 40 alkylboron group of C6 - C 60 arylboron group of C6 - C 60 arylphosphanyl group of C6 - C 60 monoarylphosphinyl group of C6 - C 60 diarylphosphinyl group of C6 - C 60 arylamine group of C5 - C 60 of aryl heteroarylamine group, and a heteroarylamine group having 5 - 60 nuclear atoms, or selected from the group consisting of L is a single bond, or an arylene group of C6 - C 18 a heteroarylene group having 5 - 18 nuclear atoms, selected from the group consisting of selected from the group consisting of R1 is an aryl group of C6 - C 60 and a heteroaryl group having 5 - 60 nuclear atoms, selected from the group consisting of selected from the group consisting of m is an integer of 1 or more, n is an integer of 0 - 3, Ar2 is an alkyl group of C1 - C 40 an alkenyl group of C2 - C 40 an alkynyl group of C2 - C 40 of an alkynyl group of C3 - C 40 a cycloalkyl group of C3 - C<0​​​​​​​​​​​​​​​​​​​60 The arylboron group, C6~C 60 The arylphosphanyl group, C6~C 60 no mo Noarylphosphenyl group, C6~C 60 diarylphosphenyl group, C6~C 60 of Arylamine group, C5~C 60 The aryl heteroarylamine group, and the number of nuclear atoms is 5~ Selected from a group consisting of 60 heteroarylamine groups, Ar1 is the moiety represented by the following chemical formula 2. [ka] In the above chemical formula 2, * represents the bonding site with chemical formula 1 above. Y is O, S, or NR 11 And, Circles A and B may be identical or different from each other, and each may independently contain heteroatoms. C5~C (not containing or not containing) 18 It is a monocyclic or polycyclic hydrocarbon ring group, R 11 and R 12 They may be the same or different from each other, and each can be independent of C1~C 12 alkyl groups, C6~C 12 The aryl group and the heteroaryl group with 5 to 12 nuclear atoms. These may be lig groups, or they may bond with adjacent groups to form a fused ring. a is between 0 and 2. The above L is an arylene group, and a heteroarylene group, the above R1 is an aryl group, and a hetero Aryl group, and the above R2, R 11 ~R 12 , and alkyl and alkenyl groups of Ar2 , alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl aryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, Alkylboron group, arylboron group, arylphosphanyl group, monoarylphosphine Nyl group, diarylphosphinyl group, arylamine group, arylheteroarylamine The group and the heteroarylamine group are each independently composed of deuterium (D), halogen, and cyanoacrylate. Nitro group, C1-C 40 alkyl groups, C2~C 40 alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclo groups with 3 to 40 nuclear atoms. Alkyl alkyl groups, C6-C 60 aryl group, heteroaryl group with 5-60 nuclear atoms, C1 ~C 40 alkyloxy group, C6~C 60 The aryloxy group, C1~C 40 no Arki Lucilyl group, C6~C 60 The arylsilyl group, C1~C 40 alkylboron group, C6 ~C 60 The arylboron group, C6~C 60 The arylphosphine group, C6~C 60 no A Reelphosphine oxide group, C6~C 60 The arylamine group, C5~C 60 Ally It consists of a heteroarylamine group and a heteroarylamine group with 5 to 60 nuclear atoms. It may be substituted with one or more substituents selected from the group, in which case the substituents are multiple If there are several, they may be identical or different from one another. However, the total number of carbon atoms contained in Ar1 that is substituted or unsubstituted with substituents is There are 16 to 24 of them.

[0011] Furthermore, the present invention relates to an anode, a cathode, and one or more organic layers interposed between the anode and the cathode. It includes, and at least one of the above one or more organic layers is the chemical represented by the above chemical formula 1. We provide organic electroluminescence containing a compound.

[0012] Furthermore, the organic layer containing the compound represented by the above chemical formula 1 is a light-emitting layer, a light-emitting auxiliary layer, and a hole injection layer. It consists of an infill layer, a hole transport layer, an electron injection layer, a lifetime improvement layer, an electron transport layer, and an electron transport auxiliary layer. A selection can be made from the group. In this case, the compound represented by the above chemical formula 1 is the phosphorescent host of the luminescent layer. The material is included as at least one of the materials, electron transport layer, and electron transport auxiliary layer. That's fine. [Effects of the Invention]

[0013] According to one embodiment of the present invention, the compound represented by the above chemical formula 1 has electron transport ability, luminescence ability, Because of its excellent heat resistance and other properties, it is used as an organic layer material for organic electroluminescent elements. It can be used.

[0014] In particular, the compound represented by chemical formula 1 of the present invention is used as a phosphorescent host, an electron transport layer, or an electron transport layer. When used as an auxiliary layer material, it offers higher thermal performance compared to conventional host materials or electron transport materials. Stability, low drive voltage, high mobility, high current efficiency, and long lifespan are achieved.

[0015] This results in an organic electroluminescent element containing the compound represented by the above chemical formula 1. It has been greatly improved in terms of superior light emission performance, low drive voltage, long lifespan, and high efficiency, therefore It can be effectively used in full-color display panels and the like.

[0016] The effects of the present invention are not limited to those described above, and a wider variety of effects are described herein. It is included in this. [Modes for carrying out the invention]

[0017] The present invention will be described in detail below.

[0018] <Novel Organic Compounds> The present invention relates to a novel aryl compound with excellent thermal stability, carrier transport ability, and luminescence. , and by including this, we aim to simultaneously achieve low voltage, high efficiency, and long life characteristics of the element. They are doing it.

[0019] Specifically, the novel organic compound represented by chemical formula 1 of the present invention has a number of aryl groups, and Ring compounds having lone pairs of electrons, for example, dibenzo / carbazole moiety (moie It contains an electron-withdrawing group (ty) which has excellent electron transport ability. The rawing group (EWG) combines to form the basic framework.

[0020] Compounds represented by chemical formula 1, which have this structure, are azines, which are a type of electron-withdrawing group. Cyclization is a cyclization in which a group (e.g., triazine, pyrimidine, etc.) has a shared electron pair on one side. By substituting numerous aryl groups in the compound and on the other side, electron-transporting electron-withdrawing groups are created. By structurally increasing electron density, electron transport capability is improved compared to existing known material structures. As a result, an effect of increased efficiency can be obtained. In addition, a dibenzo-based or ka bonded to an electron-withdrawing group can be obtained. Due to its rigid chemical structure caused by the bazole ring compound, it has a high glass transition temperature (T g) and is excellent in terms of thermal stability. Also, dibenzo-based / ka The conjugation length is relatively different due to bazole ring compounds. Increased chemical design can enhance molecular stability, thereby improving conventional techniques. Compared to other methods, this method yields devices with a longer lifespan. Furthermore, to improve the electron transfer speed, strong electrons are used. By introducing an azine group, which is a functional group with attractive force (EWG), electron injection and This will result in physicochemical properties that are even more suitable for electron transport.

[0021] Furthermore, the compound represented by chemical formula 1 of the present invention has a high triplet energy, therefore, The process by which excitons generated in the photolayer diffuse (move) to the adjacent electron transport layer or hole transport layer. This can be prevented. Therefore, the number of excitons contributing to light emission in the light-emitting layer increases, and the light emission efficiency of the device increases. Improved design enhances the durability and stability of the element, resulting in a more efficient increase in element lifespan. Most of the materials are capable of low-voltage operation, which improves their lifespan due to their physical properties. It is showing signs.

[0022] As described above, the compound represented by chemical formula 1 of the present invention is organically electroluminescent. Organic layer material of the element, preferably light-emitting layer material (blue, green and / or red phosphorescent host material) Materials, electron transport layer / injection layer materials, hole transport layer / injection layer materials, light emission auxiliary layer materials, life improvement layer When used as a material, the performance and lifespan characteristics of organic electroluminescent elements are greatly improved. This can be improved. Such organic electroluminescent elements can, as a result, produce full color. This allows for maximizing the performance of the EL panel.

[0023] The compound represented by chemical formula 1 according to the present invention is an electron-withdrawing group (EWG) with excellent electron transport ability. For example, a dibenzo / cabazole system centered around a nitrogen-containing heterocycle (e.g., an X-containing ring) A ring compound (e.g., Ar1) is bonded to a number of aryl groups (e.g., an R1-containing ring). These form the basic skeleton.

[0024] The above nitrogen-containing heterocycle (e.g., X-containing ring) is a monocyclic ring containing at least two nitrogen atoms. This is a nitrogen-containing heteroaryl group. An example of a nitrogen-containing heteroaromatic ring (e.g., an X-containing ring). So, multiple X values ​​may be the same or different from each other, and each can be independently N or CR2 And, however, at least two of the multiple Xs are N. In one specific example, multiple X contains 2 to 3 nitrogen atoms, preferably 3 nitrogen atoms. In this way, 2 to 3 nitrogen atoms The inclusion of heterocycles results in superior electron absorption properties, which are advantageous for electron injection and transport. That is the case.

[0025] In one specific example, the nitrogen-containing heterocycle (X-containing ring) is selected from the following structural formulas. One of the following options may be selected, but is not limited to this. [ka] In the above formula, * indicates the bonding site with chemical formula 1 above.

[0026] Here, even if there are multiple CR2 atoms located in a nitrogen-containing heterocycle (e.g., an X-containing ring), Often, in this case, R2 may be the same or different from each other, and each independently contains hydrogen. Deuterium (D), halogen, cyano group, nitro group, C1-C 40 alkyl groups, C2-C4 0 alkenyl group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl groups, nucleus Heterocycloalkyl groups with 3 to 40 atoms, C6-C 60 The aryl group, with 5 or more nuclei 60 heteroaryl groups, C1-C 40 alkyloxy group, C6~C 60 Ariel Oxy group, C3~C 40 alkylsilyl group, C6~C 60 The arylsilyl group, C1~ C 40 alkylboron group, C6~C 60 The arylboron group, C6~C 60 Ariel Phosphanyl group, C6~C 60 monoarylphosphenyl group, C6~C 60 The Diary Luphosphenyl group, C5~C 60 The arylamine group, C5~C 60 aryl heterogene Selected from the group consisting of a reelamine group and a heteroarylamine group with 5 to 60 nuclear atoms. It is possible. Specifically, R2 is hydrogen, deuterium (D), cyano group, C1~C 40 no Arki group, C6~C 60 It consists of an aryl group and a heteroaryl group with 5 to 60 nuclear atoms. It is preferable to select from the group.

[0027] The nitrogen-containing heterocycle (X-containing ring) according to the present invention includes various substitutions such as Ar1 and Ar2 It may be substituted. In this case, Ar1 and Ar2 may be different from each other. Either one of the above Ar1 and Ar2 has a dibenzo / carbazole ring. That's good too.

[0028] In one specific example, Ar1 has a moiety represented by the following chemical formula 2. . [ka] In the above formula, * represents the bonding site with chemical formula 1. Y is O, S, or NR 11 And, Circles A and B may be identical or different from each other, and each may independently contain heteroatoms. C5~C (not containing or not containing) 18 It can be a monocyclic or polycyclic hydrocarbon ring group. Rings A and B are monocyclic or polycyclic carbonized water molecules, respectively, which are condensed or fused monocyclic or polycyclic, as is well known in this field. It is a primary ring or a nitrogen-containing ring, for example, a monocyclic or polycyclic alicyclic ring, monocyclic or polycyclic It may be a heteroalicyclic ring, a monocyclic or polycyclic heteroaromatic ring. Preferably, the number of carbon atoms 6 to 12 monocyclic or polycyclic aromatic rings, or nuclear atoms containing at least one heteroatom. It can be a monocyclic or polycyclic heteroaromatic ring with 5 to 12 rings. Here, the heteroatoms are It can be N, O, or S. R 11 and R 12 They may be the same or different from each other, and each can be independent of C1~C 12 alkyl groups, C6~C 12 The aryl group and the heteroaryl group with 5 to 12 nuclear atoms. These may be lig groups, or they may bond with adjacent groups to form a fused ring. a is between 0 and 2. Here, if a is 0, R 12 This means that is hydrogen, a If it is 1 or 2, R 12 R can have the substituents described above. 12 multiple In this case, these may be identical or different from one another. However, Ar1 represented by the above chemical formula 2 is either substituted with the substituent described below or substituted with It is not necessary for it to be substituted in this way, and it is contained in Ar1 that is substituted or unsubstituted in this manner. The total number of carbon atoms is between 16 and 24.

[0029] In one specific example of the present invention, Ar1 is any one selected from the following structural formulas and can be embodied in these, but is not limited thereto.

Chemical formula

[0030] As a specific example of the above Ar1, the following structural formulas can be mentioned.

Chemical formula

Chemical formula

Chemical formula

[0031] Ar2 introduced into the above nitrogen-containing heterocyclic ring (X-containing ring) is an alkyl group of C1 to C 40 , an alkenyl group of C2 to C 40 , an alkynyl group of C2 to C 40 , a cycloalkyl group of C3 to C 40 , a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group of C6 to C 60 , nuclear ​​​A heteroaryl group having 5 to 60 atoms, C1 to C 40 an alkyloxy group of, C6 to C 60 an aryloxy group of, C3 to C 40 an alkylsilyl group of, C6 to C 60 an arylsilyl group, C1 to C 40 an alkylboron group of, C6 to C 60 an arylboron group of, C6 to C 60 an arylphosphanyl group of, C6 to C 60 a monoarylphosphinyl group of, C6 to C 60 a diarylphosphinyl group of, C6 to C 60 an arylamine group of, C5 to C 60 an aryl a heteroarylamine group, and a heteroarylamine group having 5 to 60 nuclear atoms can be selected from the group consisting of. Specifically, Ar2 is a C6 to C 60 aryl group, and the number of nuclear atoms selected from the group consisting of 5 to 60 heteroaryl groups, and more specifically, each independently to, C6 to C 18 aryl group, and a heteroaryl group having 5 to 18 nuclear atoms is preferred.

[0032] As a specific example of Ar2 described above, the following structural formulas can be mentioned.

Chemical formula

[0033] The nitrogen-containing heterocycle (for example, X-containing ring) according to the present invention is linked to a large number of aryl groups (R1), but is linked directly (n = 0) or via a separate linker (for example, L). Thus, a linker (L) exists between a large number of aryl group sites and the nitrogen-containing aromatic ring ​​In this case, the HOMO region is extended to give a gain to the HOMO-LUMO distribution, and HOMO -The appropriate superposition of LUMOs can improve charge transfer efficiency.

[0034] The linker (e.g., L) is not particularly limited and is a common divalent (dival) known in the art. It can be a linker in the ent) group. Specifically, L is a single bond, or C6~C 18 Selected from the group consisting of arylene groups and heteroarylene groups with 5 to 18 nuclear atoms. To obtain. More specifically, independently of each, C6~C 12 The arylene group and the nucleus with 5 atoms. It can be selected from a group consisting of ~12 heteroarylene groups.

[0035] n is an integer from 0 to 3. Here, when n is 0, L is a simple associativity, and when n is 1 to 2... In this case, there may be multiple Ls, which may be the same or different from one another.

[0036] Specific examples of allylene group linkers include phenylene groups, biphenylene groups, and naphthylene groups. n group, anthracenylene group, indenylene group, pyrantrenylene group, carbasolylene group, Thiophenylene group, indolylene group, prynylene group, quinolinylene group, pyrrolylene group, i Midazolylene group, oxazolylene group, thiazolylen group, pyridinylene group, pyrimidinylene Examples include groups such as phenylene groups or biphenylene groups. More specifically, they must be phenylene groups or biphenylene groups. Preferred. Also, as a specific example of a heteroarylene group linker, the dibenzofuran group Examples include the dibenzothiophene moiety and / or dibenzoselenophenone moiety. It can be done.

[0037] The compound of chemical formula 1 according to the present invention has a large number of nitrogen-containing heterocycles (e.g., X-containing rings) on one side. It may also contain an aryl group / heteroaryl group (e.g., an R1-containing ring).

[0038] Specifically, R1 is C6~C 60 The aryl group and the heteronuclear group with 5 to 60 atoms. The number of aryl / heteroaryl groups to be introduced can be selected from the group consisting of reel groups. (m) is an integer greater than or equal to 1, preferably between 1 and 5. In this case, when m is between 2 and 5 In some cases, multiple R1s may be identical or different from one another.

[0039] In one specific example, R1 is C6~C 12 It is an aryl group, and m is an integer from 1 to 5. The carbon contained in R1 is either substituted with the substituents described later or is not substituted. The number is at least 18.

[0040] In the above chemical formula 1, the above L is an arylene group, and the above R1 is an arylene group. A heteroaryl group, and the above R2, R 11 ~R 12 , and Ar2's Alky Alkenyl group, Alkinyl group, Cycloalkyl group, Heterocycloalkyl group, Alkinyl group aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, Arylsilyl group, alkylboron group, arylboron group, arylphosphanyl group, mo Noarylphosphenyl group, diarylphosphenyl group, arylamine group, aryl The teloarylamine group and the heteroarylamine group are each independently composed of deuterium (D) , halogen, cyano group, nitro group, C1~C 40 alkyl groups, C2~C 40 of Archen group, C2~C 40 Alkynyl group, C3~C 40 Cycloalkyl groups, with 3-4 nuclear atoms. 0 heterocycloalkyl groups, C6~C 60 The aryl group, the hetyl group with 5 to 60 nuclei Roaryl group, C1~C 40 alkyloxy group, C6~C 60 The aryloxy group, C 1~C 40 alkylsilyl group, C6~C 60 The arylsilyl group, C1~C 40 Al quilborone group, C6~C 60 The arylboron group, C6~C 60 arylphosphine group , C6~C 60 The arylphosphine oxide group, C6~C 60 The arylamine group, C 5~C 60 The aryl heteroarylamine group, and the heteroaryl group with 5 to 60 nuclear atoms. It may be substituted with one or more substituents selected from the group consisting of luamine groups, and If there are multiple substituents, they may be identical or different from one another.

[0041] In one embodiment of the present invention, the compound represented by the above chemical formula 1 is a linker (L) and non Ring compounds having a shared electron pair, specifically, dibenzo / carbazole moieties (for example, Depending on the type of Ar1), it can be expressed as one of the following chemical formulas 3 to 9. However, it is not limited to these. [ka] [ka] [ka] [ka] [ka] [ka] [ka] In the above formula, X, Y, Ar2, R1, n, and m are as defined in claim 1, respectively. Circle D is a monocyclic or polycyclic hydrocarbon ring group that may or may not contain a heteroatom.

[0042] In another embodiment of the present invention, the compound represented by the above chemical formula 1 is introduced into the molecule. Depending on the number of aryl groups (R1) and their bonding positions, the following chemical formulas 10~ It can be materialized in any one of the formulas in Equation 21, but is not limited to these. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] In the above formula, X, Ar1, Ar2, L, R1, and n are as defined in claim 1, respectively.

[0043] The compound represented by chemical formula 1 of the present invention as described above is a compound exemplified below, for example, This can be embodied in compounds represented by 1 to 93, but is not limited to these. [ka] [ka] [ka] [ka] [ka] [ka]

[0044] In this invention, "alkyl" refers to a linear or branched saturated carbonate containing 1 to 40 carbon atoms. This refers to monovalent substituents derived from an element. Examples include methyl, ethyl, propyl, and ethyl. Examples include sorbyl, sec-butyl, pentyl, iso-amyl, and hexyl, This is not limited to these.

[0045] In this invention, "alkenyl" refers to a carbon atom having one or more carbon-carbon double bonds. This refers to monovalent substituents derived from 2 to 40 linear or branched unsaturated hydrocarbons. Examples include vinyl, allyl, isopropenyl, and 2-butenyl, but It is limited to others.

[0046] In this invention, "alkynyl" refers to a carbon atom having one or more carbon-carbon triple bonds. This refers to monovalent substituents derived from 2 to 40 linear or branched unsaturated hydrocarbons. Examples include ethinyl and 2-propynyl, but are not limited to these.

[0047] In this invention, "aryl" refers to a single ring or a combination of two or more rings with 6 carbon atoms. This refers to monovalent substituents derived from aromatic hydrocarbons up to 40. Note that two or more rings are penetrovalent. It may also be in the form of a pendant or condensed form. Examples include phenyl Examples include naphthyl, phenanthryl, and anthrill, but the term is not limited to these.

[0048] In the present invention, "heteroaryl" refers to a monoheterocycle or poly(poly) with 5 to 40 nuclear atoms. This refers to a monovalent substituent derived from a heterocyclic aromatic hydrocarbon. In this case, one or more substituents in the ring The upper carbon atoms, preferably 1 to 3 carbon atoms, are substituted with heteroatoms such as N, O, S, or Se. It is done. Furthermore, two or more rings are in the form of a pendant or condensation, and consequently the aryl group and It may also be in the form of a condensation. Examples of this include pyridinyl, pyrazinyl, and pyrimidinyl. , pyridazinyl, triazinyl, and other 6-membered monocyclic rings, phenoxatienyl (phen oxathienyl), indolizinyl, indolyl (i ndolyl, purinyl, quinolyl, benzo Thiazoles (benzothiazole), carbazolyl Polycyclic rings such as 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pi Examples include lysinyl and 2-pyrimidinyl, but the term is not limited to these.

[0049] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, and the above R This refers to aryl atoms with 5 to 40 carbon atoms. Examples include phenyloxy and naphthyl. Examples include oxy and diphenyloxy, but are not limited to these.

[0050] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, as described above. R' stands for alkyl, which has 1 to 40 carbon atoms, and can be linear or branched. It may also be nched, or cyclic in structure. An example of this is Metoki C, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pent Examples include, but are not limited to, kishi.

[0051] In the present invention, "arylamine" refers to an aryl substituted with an aryl group having 6 to 40 carbon atoms. It means "min".

[0052] In this invention, "cycloalkyl" refers to a monocyclic or polycyclic non-aromatic compound having 3 to 40 carbon atoms. This refers to monovalent substituents derived from hydrocarbons. Examples include cyclopropyl and cyclo Examples include pentyl, cyclohexyl, norbornyl, and adamantine, but these Not limited.

[0053] In this invention, "heterocycloalkyl" refers to non-aromatic carbonate water with 3 to 40 nuclear atoms. This refers to a monovalent substituent derived from an element, and one or more carbon atoms in the ring, preferably 1 to 3 carbon atoms. This is replaced by a heteroatom such as N, O, S, or Se. An example of this is morpholine. Examples include piperazine, but are not limited to these.

[0054] In the present invention, "alkylsilyl" refers to a alkyl substituted with an alkyl group having 1 to 40 carbon atoms. It means lyl, and "arylsilyl" refers to a compound that is substituted with an aryl group having 5 to 40 carbon atoms. It means Cyril.

[0055] In this invention, "condensed ring" refers to a condensed aliphatic ring, a condensed aromatic ring, or a condensed heteroaliphatic ring. This refers to condensed heteroaromatic rings, or combinations thereof.

[0056] <Electron transport layer material> The present invention provides an electron transport layer containing the compound represented by the above chemical formula 1.

[0057] The electron transport layer (ETL) described above transports electrons injected from the cathode to the adjacent layer, specifically, Its role is to move the light-emitting layer.

[0058] The compound represented by the above chemical formula 1 can be used alone as an electron transport layer (ETL) material, or This material may be mixed with electron transport layer materials well known in this field, but it is preferable to use it alone.

[0059] The electron transport layer material that can be mixed with the compound of chemical formula 1 above is an electron transport material well known in this field. Includes. Usable electron transport materials include, for example, oxazole compounds and isoxazo Al-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds Compounds, thiadiazole compounds, perylene compounds, aluminum complexes (e.g., Alq 3(tris(8-quinolinol)-aluminum(tris(8-quinolinol) ato)-aluminium), BAlq, SAlq, Almq3, gallium complex (example) Examples include Gaq'2OPiv, Gaq'2OAc, and 2(Gaq'2)). These are not limited to these. They may be used individually or in combination of two or more.

[0060] In the present invention, when the compound of chemical formula 1 and the electron transport layer material are mixed, these The mixing ratio is not particularly limited and can be adjusted as appropriate within the scope of what is well known in this field.

[0061] <Electron transport auxiliary layer material> Furthermore, the present invention provides an electron transport auxiliary layer containing the compound represented by the above chemical formula 1.

[0062] The electron transport layer is placed between the light-emitting layer and the electron transport layer, and excitation generated in the light-emitting layer It plays a role in preventing the diffusion of punctures or holes into the electron transport layer.

[0063] The compound represented by the above chemical formula 1 can be used alone or partially as an electron transport auxiliary layer material. It may be mixed with electron transport layer materials that are well known in the field, but it is preferable to use it alone.

[0064] The electron transport auxiliary layer material that can be mixed with the compound of chemical formula 1 above is an electron transport material well known in this field. It contains quality. Examples of the electron transport auxiliary layer include oxadiazole derivatives and triazoles. Examples include leu derivatives, penanthroline derivatives (e.g., BCP), and nitrogen-containing heterocyclic derivatives. It can be listed.

[0065] In the present invention, when the compound of chemical formula 1 and the electron transport auxiliary layer material are mixed, The mixing ratio is not particularly limited and can be adjusted as appropriate within the scope known in this field.

[0066] <Organic electroluminescent element> Furthermore, in other aspects, the present invention relates to the chemical formula represented by the above-described chemical formula 1. This concerns organic electroluminescent devices (organic EL elements) that include composite materials.

[0067] Specifically, the present invention relates to an anode, a cathode, and the anode and cathode. An organic electroluminescent element comprising one or more organic layers interposed between, At least one of the one or more organic layers described above contains the compound represented by the above chemical formula 1. It includes. In this case, the above compounds may be used alone or in a mixture of two or more.

[0068] The above one or more organic layers include a hole injection layer, a hole transport layer, a light emission layer, a light emission auxiliary layer, and a lifespan improvement layer. It consists of one or more of the following: an electron transport layer, an electron transport auxiliary layer, and an electron injection layer. At least one organic layer contains the compound represented by the above chemical formula 1. Specifically, The organic layer containing the compound of chemical formula 1 is a light-emitting layer (more specifically, a phosphorescent host material). Preferably, it is an electron transport layer and an electron transport auxiliary layer.

[0069] The light-emitting layer of the organic electroluminescent element according to the present invention comprises a host material and a dopant The material includes a component, and in this case, the host material may include the compound of chemical formula 1 described above. Furthermore, the light-emitting layer of the present invention contains, in addition to the compound of chemical formula 1 above, a compound well known in the art. It may be included as a to.

[0070] The compound represented by the above chemical formula 1 is used as a light-emitting layer material for an organic electroluminescent element. Furthermore, when included as a blue, green, or red phosphorescent host material, the interaction between holes and electrons in the light-emitting layer Because the bonding force is increased, the efficiency of the organic electroluminescent element (luminescence efficiency and power efficiency) is increased. The efficiency, lifespan, brightness, and drive voltage can be improved. Specifically, represented by the above chemical formula 1 The compounds are used as green and / or red phosphorescent hosts, fluorescent hosts, or dopant materials. It is preferable that it be included in an organic electroluminescent element. In particular, the chemical formula 1 of the present invention The compound shown is an excyplex N-type with high efficiency green phosphorescence in the luminescent layer. It is preferable that it be a host material.

[0071] The structure of the organic electroluminescent element of the present invention is not particularly limited, but The substrate, anode, hole injection layer, hole transport layer, light emission auxiliary layer, light emission layer, electron transport layer, and cathode are It may be a structure in which layers are stacked in order. In this case, the hole injection layer, hole transport layer, light emission auxiliary layer, One or more of the light-emitting layer, electron transport layer, and electron injection layer are the compound represented by the above chemical formula 1. It contains a substance, preferably a light-emitting layer, and more preferably a phosphorescent host represented by the above chemical formula 1. It may contain compounds. Furthermore, an electron injection layer is further laminated on top of the electron transport layer. It's fine if you do that.

[0072] The structure of the organic electroluminescent element of the present invention has an insulating layer at the interface between the electrode and the organic material layer. It may be a structure in which layers or adhesive layers are inserted.

[0073] The organic electroluminescent element of the present invention has one or more of the above-mentioned organic layers Aside from containing the compound represented by the above chemical formula 1, the materials and methods are known in the industry. It can be manufactured by forming a material layer and electrodes.

[0074] The above organic layer can be formed by vacuum deposition or solution coating. Examples of methods include spin coating, deep coating, and doctor blade coating. Examples include, but are not limited to, the printing method, inkjet printing method, or thermal transfer method. do not have.

[0075] Substrates that can be used in the manufacture of the organic electroluminescent element of the present invention include: Not particularly limited, for example, silicon wafers, quartz, glass plates, metal plates, plastic sheets Examples include, but are not limited to, films and sheets.

[0076] Furthermore, any anode material well-known in this field can be used without restriction as the anode material. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; zinc oxide Indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO) Metal oxides such as ZnO:Al or SnO2:Sb; combinations of metals and oxides Combination; polythiopene, poly(3-methylthiophene), poly[3,4-(ethylene-1 Conductive materials such as ,2-dioxy)thiopene (PEDT), polypyrrole, or polyaniline Examples include, but are not limited to, polymers and carbon black.

[0077] Furthermore, any cathode material well known in this field can be used without restriction as the cathode material. For example, magnesium, calcium, sodium, potassium, titanium, indium, and Thorium, lithium, gadolinium, aluminum, silver, tin, or metals such as lead Examples include these alloys; and multilayer materials such as LiF / Al or LiO2 / Al. However, it is not limited to these.

[0078] In addition, the hole injection layer, hole transport layer, electron injection layer, and electron transport layer are not particularly limited, and substances well-known in the art can be used.

Examples

[0079] Hereinafter, the present invention will be described in detail based on examples. However, the examples described below are merely illustrative of the present invention, and the present invention is not limited by these examples.

[0080] [Preparation Example 1] <Step 1>Synthesis of 3’-chloro-5’-phenyl-1,1’:2’,1’’-terphenyl

Chemical formula

[0081] ​ <Step 2> Synthesis of Core1 [ka] 3'-Chloro-5'-phenyl-1,1':2',1''-terphenyl 75.6g ( 221.7 mmol), 4,4,4',4',5,5,5',5'-Octamethyl-2, 2'-bi(1,3,2-dioxaborolane) 73.2g (288.3 mmol), and P d2(dba)36.1g(6.7mmol), KOAc65.3g(665.4mm Add 6.3g (13.3 mmol) of Xphos to 750ml of 1,4-dioxane. The mixture was added and heated under reflux for 12 hours. After the reaction was complete, it was extracted with dichloromethane to obtain MgSO4. After adding the solvent and removing the water, filtration was performed. After filtration, the solvent in the organic layer was concentrated under reduced pressure and dichloroethylene was used. After purification by column chromatography using romethane and hexane, methanol was used. It solidified. The solid was filtered, washed with methanol, and dried in an oven to obtain Cor 72.7 g of e1 was obtained (yield 75.8%). Mass:[(M+H)] + ]:433

[0082] [Preparation Example 2] <Step 1> 5'-Chloro-1,1':3',1'':3'',1'''-Quatelf Enyl synthesis [ka] 3-Bromo-5-chloro-1,1'-biphenyl 70g (261.6 mmol), and [1,1'-Biphenyl]-3-Ilboronic acid 54.4g (274.7mmol), Pd (PPh3)49.1g(7.8mmol), K2CO3108.5g(784.9 (mmol) was placed in 870 ml of THF and 220 ml of H2O, and 5'-chloro-1,1':3',1'':3'',1''' - quaterphenyl was obtained in the same manner as in <Step 1> of [Preparation Example 1]. 74.1 g (yield 83.1%) of was obtained. Mass: [(M + H) + : 341

[0083] <Step 2> Synthesis of Core2

Chemical Structure

[0084] [Preparation Example 3] <Step 1> Synthesis of 5'-chloro - 3'-phenyl - 1,1':2',1'' - terphenyl

Chemical Structure

[0085] <Step 2> Core3 synthesis [ka] 5'-Chloro-3'-phenyl-1,1':2',1''-terphenyl 47.5g ( 139.3 mmol), 4,4,4',4',5,5,5',5'-Octamethyl-2, 2'-bi(1,3,2-dioxaborolane) 45.9g (181.1 mmol), and P d2(dba)33.8g(4.2mmol), KOAc41.0g(417.9mm Add 4.0g (8.3 mmol) of Xphos to 470ml of 1,4-dioxane. Then, using the same synthesis method as for Core1 in [Preparation Example 1], 45.25 g of Core3 was produced (yield 75.1% was obtained. Mass:[(M+H)] + ]:433

[0086] [Preparation Example 4] <Step 1> 5''-Chloro-1,1':3',1'':3'',1''':4'' Synthesis of ',1''''-Kinkiphenyl [ka] 3-Bromo-5-chloro-1,1':4',1''-terphenyl 50g (145.5 mmol), and [1,1'-biphenyl]-3-ylboronic acid 30.2 g (152.8 mmol), Pd(PPh3)45.0g(4.4mmol), K2CO360.3 Add g (436.5 mmol) to 490 ml of THF and 125 ml of H2O, [Preparation example] 5''-Chloro-1,1':3',1'':3'' 53.9 g of ,1''':4''',1''''-quinkiphenyl was obtained (yield 88.9%). Ta. Mass:[(M+H)] + ]:417

[0087] <Step 2> Core4 synthesis [ka] 5''-Chloro-1,1':3',1'':3'',1''':4''',1''' '-Kinkiphenyl 53.9g (129.3 mmol), 4,4,4',4',5,5, 5',5'-Octamethyl-2,2'-bi(1,3,2-dioxaborolane) 45.9g (181.1mmol), and Pd2(dba)33.6g(3.9mmol), KO Ac38.1g (388.0 mmol), Xphos3.7g (7.8 mmol), 1 Place in 430 ml of ,4-dioxane and proceed in the same manner as the synthesis method for Core 1 in [Preparation Example 1]. We obtained 41.96g of Core4 (63.8% yield). Mass:[(M+H)] + ]:508

[0088] [Preparation Example 5] <Step 1> 2-(5'-chloro-[1,1':3',1''-terphenyl]-4- Synthesis of ylnaphthalene [ka] 3-Bromo-5-chloro-1,1'-biphenyl 50g (186.9 mmol), and (4-Naphthalene-2-yl)phenyl)boronic acid 48.9g (196.2 mmol), Pd(PPh3)46.5g(5.6mmol), K2CO377.5g(560. Add 6 mmol) to 625 ml of THF and 155 ml of H2O, and then add the <Stage> from [Preparation Example 1]. Similar to step 1, 2-(5'-chloro-[1,1':3',1''-terphenyl] 55.9 g of -4-yl)naphthalene was obtained (yield 76.6%). Mass:[(M+H)] + ]:391

[0089] <Step 2> Core5 synthesis [ka] 2-(5'-chloro-[1,1':3',1''-terphenyl]-4-yl)naphtha Len 55.9g (143.1 mmol), 4,4,4',4',5,5,5',5'-O Kutamethyl-2,2'-bi(1,3,2-dioxaborolane) 47.2g (186.1mg) mol), and Pd2(dba)33.9g (4.3mmol), KOAc42.1g (429.4 mmol), Xphos 4.1 g (8.6 mmol), 1,4-dioxa Place in 480ml and combine Core5 in the same way as the synthesis method for Core1 in [Preparation Example 1]. 0.26 g (yield 58.3%) was obtained. Mass:[(M+H)] + ]:483

[0090] [Preparation Example 6] <Step 1> 3-(5-chloro-[1,1'-biphenyl]-3-yl)dibenzo[b ,d] Synthesis of furan [ka] 3-Bromo-5-chloro-1,1'-biphenyl 50g (186.9 mmol), and Dibenzo[b,d]furan-3-ylboronic acid 41.6g (196.2 mmol), Pd (PPh3)46.5g(5.6mmol), K2CO377.5g(560.6m Add (mol) to 625 ml of THF and 155 ml of H2O, and follow the steps in [Preparation Example 1]. 1> Similarly, 3-(5-chloro-[1,1'-biphenyl]-3-yl)dibenzo[ 56.4 g of [b,d] furan was obtained (yield 85.1%). Mass:[(M+H)] + ]:355

[0091] <Step 2> Core6 Synthesis [ka] 3-(5-chloro-[1,1''-biphenyl]-3-yl)dibenzo[b,d]furan 56.4g (159.0 mmol), 4,4,4',4',5,5,5',5'-octa Methyl-2,2'-bi(1,3,2-dioxaborolane) 52.5g (206.7mmo l), and Pd2(dba)34.4g(4.7mmol), KOAc46.8g(4 77.1 mmol), Xphos 4.5 g (9.5 mmol), 1,4-dioxane 5 Add to 30 ml and synthesize Core 6 using the same method as for Core 1 in [Preparation Example 1]. 7g (79.9% yield) was obtained. Mass:[(M+H)] + ]:447

[0092] [Synthesis Example 1] Synthesis of Compound 1 [ka] 2-(4-chlorophenyl)-4-phenyl-6-(1-phenyldibenzo[b,d] 15.0g (leq, 29.4 mmol) fran-3-yl-1,3,5-triazine [Preparation Example 1] Core1 13.4g (1.05eq, 30.9 mmol), Pd( OAc)20.2g(0.03eq, 0.9mmol), Cs2CO328.7g( 3.0eq, 88.2mmol), Xphos0.8g(0.06eq, 1.8mmol) ) is placed in 100 ml of toluene, 25 ml of ethanol, and 25 ml of H2O, and heated for 12 hours. The reaction was carried out under reflux. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The process was carried out. After removing the solvent from the filtered organic layer, dichloromethane and hexane were used to color the mixture. After chromatography, compound 1 was recrystallized in toluene and acetone, and the compound was converted to 15.8 g (68.8% yield) was obtained. Mass:[(M+H)] + ]:780

[0093] [Synthesis Example 2] Synthesis of Compound 3 [ka] 2-(4-chlorophenyl)-4-phenyl-6-(phenyldibenzo[b,d]fura Instead of 1,3,5-triazine, use 4-(3-chlorophenyl)-2 -Phenyl-6-(1-phenyldibenzo[b,d]furan-4-yl)pyrimidine 15 Except for using 0.0g (29.5 mmol), the process was the same as in [Synthesis Example 1], using the same equivalent ratio. This yielded 12.7 g of compound 3 (55.2% yield). Mass:[(M+H)] + ]:779

[0094] [Synthesis Example 3] Synthesis of Compound 11 [ka] 2-(4-chlorophenyl)-4-phenyl-6-(phenyldibenzo[b,d]fura Instead of 2-(4-chlorophenyl)-4 (-3-yl)-1,3,5-triazine, use 2-(4-chlorophenyl)-4 -(naphtho[2,1-b]benzofuran-9-yl)-6-phenyl-1,3,5-tri Except for using 15.0g (30.9 mmol) of adin, the equivalent ratio was the same as in [Synthesis Example 1]. By a similar process, 19.0 g of compound 11 (yield 81.4%) was obtained. Mass:[(M+H)] + ]:754

[0095] [Synthesis Example 4] Synthesis of Compound 16 [ka] 4'-(4-(benzo[b]naphtho[2,1-d]thiophen-9-yl)-6-(3 -Chlorophenyl)-1,3,5-triazine-2-yl)-[1,1'-biphenyl] -3-Carbonitrile 10.0g (leq, 16.6 mmol), [1,1':3',1 ''-Terphenyl]-5'-Ilboronic acid 4.78g (1.05eq, 17.4mO) l), Pd(OAc)20.1g(0.03eq, 0.5mmol), Cs2CO3 16.26g(3.0eq, 49.9mmol), Xphos0.5g(0.06eq, Add 1.0 mmol) to 130 ml of toluene, 30 ml of ethanol, and 30 ml of H2O. The reaction was carried out under heating and reflux for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was obtained. The mixture was added and filtered. After removing the solvent from the filtered organic layer, dichloromethane and hexane were added. After performing column chromatography using [the specified method], the compound was recrystallized with toluene and acetone. 5.7 g of 16 was obtained (yield 42.8%). Mass:[(M+H)] + ]:795

[0096] [Synthesis Example 5] Synthesis of Compound 17 [ka] 2-(4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine-2-i (Lu)-4-(naphthalene-2-yl)-9-phenyl-9H-carbazole 15.0g leq, 23.6 mmol), Core2 10.7 g (1.05 eq, [Preparation Example 2] 24.8mmol), Pd(OAc)20.16g(0.03eq, 0.7mmol) , Cs2CO323.1g(3.0eq, 70.8mmol), Xphos0.67g (0.06 eq, 1.4 mmol) in 100 ml toluene, 25 ml ethyl OH, H2O The mixture was placed in 25 ml of water and heated under reflux for 8 hours to allow the reaction to proceed. After the reaction was complete, it was extracted with dichloromethane. Then, MgSO4 was added and filtration was performed. After removing the solvent from the filtered organic layer, dichloro After performing column chromatography using methane and hexane, the following steps were performed using toluene and acetone. The compound was recrystallized to obtain 10.9 g of compound 17 (yield 51.2%). Mass:[(M+H)] + ]:906

[0097] [Synthesis Example 6] Synthesis of Compound 28 [ka] 4-(benzo[b]naphtho[1,2-d]thiophen-6-yl)-6-(5-chloro -[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine 15.0g (leq Core3 11.8g (1.05eq, 27) [Preparation Example 3] (26.08 mmol), .39mmol), Pd(OAc)20.18g(0.03eq, 0.8mmol), Cs2CO325.5g(3.0eq, 78.2mmol), Xphos0.74g( (0.06 eq, 1.6 mmol) in 100 ml of toluene, 30 ml of ethanol, H2O3 The mixture was placed in 0 ml of water and heated under reflux for 8 hours to allow the reaction to proceed. After the reaction was complete, it was extracted with dichloromethane. MgSO4 was added and filtration was performed. After removing the solvent from the filtered organic layer, dichloromethyl After performing column chromatography using tan and hexane, re-spectrum chromatography was performed using toluene and acetone. Crystallization was performed, yielding 15.7 g of compound 28 (71.1% yield). Mass:[(M+H)] + ]:845

[0098] [Synthesis Example 7] Synthesis of Compound 37 [ka] 2-(4-chlorophenyl)-4-phenyl-6-(1-phenyldibenzo[b,d] Instead of furan-3-yl)-1,3,5-triazine, use 2-(4-chlorophenyl) -4-(naphtho[2,1-b]benzofuran-9-yl)-6-phenyl-1,3,5- Except for using 15.0 g (30.9 mmol) of triazine, the equivalent amounts are the same as in [Synthesis Example 1]. Compound 37 was obtained in 17.8 g (76.5% yield) by a similar process. Mass:[(M+H)] + ]:754

[0099] [Synthesis Example 8] Synthesis of Compound 49 [ka] 2-([1,1'-biphenyl]-4-yl)-4-(6-chloro-[1,1'-biphenyl] [enyl]-3-yl)-6-(naphtho[2,1-b]benzofuran-5-yl)pyrimid 13.0g (leq, 20.5 mmol), [1,1':3',1''-terphenyl ]-5'-Ilboronic acid 5.9g (1.05eq, 21.5 mmol), Pd(OAc) 20.14g(0.03eq, 0.6mmol), Cs2CO320.0g(3.0 (eq, 61.4 mmol), Xphos 0.6 g (0.06 eq, 1.2 mmol), Add 130 ml of toluene, 30 ml of ethanol, and 30 ml of H2O, and heat under reflux for 10 hours. The reaction was carried out. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. After removing the solvent from the filtered organic layer, column chromatography was performed using dichloromethane and hexane. After matrixing, the compound 49 was recrystallized with toluene and acetone, yielding 8.3 g (amount). A rate of 48.9% was obtained. Mass:[(M+H)] + ]:830

[0100] [Synthesis Example 9] Synthesis of Compound 50 [ka] 2-(4-chlorophenyl)-4-phenyl-6-(1-phenyldibenzo[b,d] Instead of furan-3-yl)-1,3,5-triazine, use 3-(4-(3-chlorophenate (Nyl)-6-phenylpyrimidine-2-yl)-5-phenyl-5H-benzo[b]cal Except for using 14.0 g (25.1 mmol) of bazole, the equivalent ratio was the same as in [Synthesis Example 1]. A similar process yielded 11.1 g of compound 50 (yield 53.4%). Mass:[(M+H)] + ]:829

[0101] [Synthesis Example 10] Synthesis of Compound 58 [ka] 2-([1,1'-biphenyl]-4-yl)-4-(6-chloro-[1,1'-biphenyl] [enyl]-3-yl)-6-(naphtho[2,1-b]benzofuran-5-yl)pyrimid Instead of n, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl (Lu)-6-(2-phenyldibenzo[b,d]thiophen-4-yl)-1,3,5-to Except for using 14.0 g (25.1 mmol) of lyazin, the equivalent ratio is the same as in [Synthesis Example 8]. A similar process yielded 12.4 g of compound 58 (62.5% yield). Mass:[(M+H)] + ]:797

[0102] [Synthesis Example 11] Synthesis of Compound 72 [ka] 2-([1,1'-biphenyl]-4-yl)-4-(6-chloro-[1,1'-biphenyl] [enyl]-3-yl)-6-(naphtho[2,1-b]benzofuran-5-yl)pyrimid Instead of n, 2-(4-chlorophenyl)-4-(7,8-diphenyldibenzo[b, Use 14.0g (25.1 mmol) of [d]furan-2-yl)-6-phenylpyrimidine. Except for the use of [Synthesis Example 8], 14.4 g of compound 72 was obtained by the same equivalent ratio and similar process. A yield of 72.1% was obtained. Mass:[(M+H)] + ]:799

[0103] [Synthesis Example 12] Synthesis of Compound 80 [ka] 2-(4-chlorophenyl)-4-(7-(naphthalene-2-yl)dibenzo[b,d 12.0 g (leq, 21.5 mmol) furan-2-yl-6-phenylpyrimidine ), [Preparation Example 4] Core4 9.7g (1.05eq, 22.5 mmol), Pd( OAc)20.14g(0.03eq, 0.6mmol), Cs2CO321.0g (3.0eq, 64.4mmol), Xphos0.61g(0.06eq, 1.3mm Add (ol) to 140 ml of toluene, 35 ml of ethanol, and 35 ml of H2O, and heat for 8 hours. The reaction was carried out under reflux. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The following procedure was performed. After removing the solvent from the filtered organic layer, dichloromethane and hexane were used to extract the solution. After performing Lamb chromatography, the compound 80 was recrystallized with toluene and acetone, and 10 0.1g (yield 51.8%) was obtained. Mass:[(M+H)] + ]:906

[0104] [Synthesis Example 13] Synthesis of Compound 81 [ka] 4-(benzo[b]-naphtho[1,2-d]thiophene-6-yl)-6-(5-chloro Instead of lo-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine, 2- (4-chlorophenyl)-4-(naphtho[1,2-b]benzofuran-8-yl)-6- Except for using 15.0 g (31.0 mmol) of phenyl-1,3,5-triazine, [Synthesis Example 6] Compound 81 was synthesized in the same equivalent ratio and process as above, yielding 19.2 g (82.2%). ) obtained. Mass:[(M+H)] + ]:755

[0105] [Synthesis Example 14] Synthesis of Compound 82 [ka] 2-(3-chlorophenyl)-4-phenyl-6-(1-phenyldibenzo[b,d] Thiofen-4-yl)-1,3,5-triazine 13.0g (leq, 24.7mmo) l), Core5 12.5g (1.05eq, 25.9 mmol) from [Preparation Example 5], P d(OAc)20.17g(0.03eq, 0.67mmol), Cs2CO324 .1g(3.0eq, 74.1mmol), Xphos0.7g(0.06eq, 1.5 Place mmol) in 150 ml of toluene, 40 ml of ethyl OH, and 40 ml of H2O, and leave for 8 hours. The reaction was carried out by heating under reflux. After the reaction was complete, the mixture was extracted with dichloromethane, and MgSO4 was added. Filtration was performed. After removing the solvent from the filtered organic layer, dichloromethane and hexane were used. After performing column chromatography, the compound 82 was recrystallized in toluene and acetone. 13.2g (yield 63.3%) was obtained. Mass:[(M+H)] + ]:847

[0106] [Synthesis Example 15] Synthesis of Compound 83 [ka] 4-(4-chlorophenyl)-6-(naphtho[2,1-b]benzofuran-9-yl) -2-phenylpyrimidine 15.0 g (leq, 31.1 mmol), C of [Preparation Example 6] ore6 14.6g(1.05eq, 25.9mmol), Pd(OAc)20.2 1g(0.03eq, 0.93mmol), Cs2CO330.4g(3.0eq, 9 3.2 mmol), Xphos 0.9 g (0.06 eq, 1.9 mmol), toluene Add 150 ml of ethanol, 40 ml of ethoxide, and 40 ml of H2O, and heat under reflux for 10 hours to react. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. After removing the solvent from the organic layer, column chromatography was performed using dichloromethane and hexane. After the procedure, the compound 83 was recrystallized with toluene and acetone, yielding 19.5 g (yield 81%). 0.9% was obtained. Mass:[(M+H)] + ]:768

[0107] [Examples 1-10] Fabrication of a blue organic electroluminescent element Compounds 1-93 were purified to high purity by conventional sublimation methods, and then, as shown below, blue organic elements were obtained. We fabricated an octoluminescent element. First, ITO (Indium Tin Oxide) is used as a thin film coating with a thickness of 1500 Å. The coated glass substrate was cleaned using ultrasonic cleaning with distilled water. After the cleaning with distilled water was completed, Ultrasonic cleaning is performed using solvents such as isopropyl alcohol, acetone, and methanol, followed by drying. After that, use a UV ozone cleaner (Power sonic 405, manufactured by Fascintech). After transfer, the substrate was cleaned using UV light for 5 minutes, and then transferred to a vacuum deposition machine. On the transparent ITO electrode prepared as described above, HT-1 + 2% HAT-CN(100 Å) / HT-1(1400Å) / HT-2(50Å) / BH+2%BD(200Å) / E T-2(50Å) / each compound from compound 1 to 87:LiQ=1:1(300Å) / Li By stacking F (10 Å) / Al (1000 Å) in that order, an organic electroluminescent element is created. I made it.

[0108] The HT-1, HAT-CN, HT-2, BH, BD, ET-1, and E were used at this time. The structures of T-2 and LiQ are as follows: [ka] [ka] [ka]

[0109] [Comparative Example 1] Fabrication of a blue organic electroluminescent element Instead of compounds 1-87 used as electron transport layer material, ET-1 was used at a thickness of 300 Å. A blue organic electroluminescent element was produced in the same manner as in Example 1, except that it was deposited using a different method. I made it.

[0110] [Evaluation Example 1] Blue organic electroluminescents produced in Examples 1-10 and Comparative Example 1, respectively. Regarding the element, the current density is 10 mA / cm². 2 The drive voltage, current efficiency, and light emission peak at The measurements were taken, and the results are shown in Table 1 below.

[0111] [Table 1]

[0112] As shown in Table 1 above, the compound according to the present invention is used as an electron transport layer material in the implementation. The blue organic electroluminescent elements in Examples 1-10 are used in electron transport compared to conventional ET-1. Compared to the blue organic electroluminescent element used in Comparative Example 1 for the layer, the driving voltage, It was found to exhibit excellent performance in terms of luminescence peak and current efficiency.

[0113] [Examples 11-33] Fabrication of a blue organic electroluminescent element Compounds 1-93 were purified to high purity by conventional sublimation methods, and then, as shown below, blue organic elements were obtained. We fabricated an octoluminescent element. ITO (Indium Tin Oxide) thin film coating with a thickness of 1500 Å The glass substrate, which had been treated with [a specific coating], was cleaned with ultrasonic waves using distilled water. After the cleaning with distilled water was complete, [another specific coating] was used. After ultrasonic cleaning with solvents such as ropil alcohol, acetone, or methanol, and then drying, Then, it is transferred to a UV ozone cleaning machine (Power sonic 405, manufactured by Fascintech). Afterward, the substrate was cleaned using UV light for 5 minutes and then transferred to a vacuum deposition machine. On the transparent ITO electrode prepared as described above, HT-1 + 2% HAT-CN(100 ) / HT-1(1400Å) / HT-2(50Å) / BH+2%BD(200Å) / Compound 1~93(50Å) / ET-1:LiQ=1:1(300Å) / LiF(10Å) / An organic electroluminescent device was fabricated by stacking layers of Al (1000 Å) in that order. The HT-1, HAT-CN, HT-2, BH, BD, ET-1, and E were used at this time. The structures of T-2 and LiQ are as described in [Examples 1-10] above.

[0114] [Comparative Examples 2-5] Fabrication of a blue organic electroluminescent element Without using compounds 1-93 which were used as electron transport auxiliary layer materials in Example 11, Except for depositing the auxiliary transport layer material ET-2 to ET-6 to a thickness of 50 Å, the process was the same as in Example 11. A blue organic electroluminescent element was fabricated in a similar manner. The structures of ET-2 to ET-6 used at that time are as follows: [ka]

[0115] [Evaluation Example 2] Blue organic electroluminescent material produced in Examples 11-33 and Comparative Example 2 For the saturation element, the current density is 10 mA / cm². 2 Driving voltage, current efficiency, and emission peak The following measurements were taken, and the results are shown in Table 2 below.

[0116] [Table 2]

[0117] As shown in Table 2 above, an embodiment comprising the compound according to the present invention as an electron transport auxiliary layer material The blue organic electroluminescent elements in Examples 11-33 are contained within the dibenzo-based moiety. Comparative Examples 2-6 containing compounds with a different number of carbon atoms than those of the present invention showed organic electroluminescence It was found to exhibit superior performance in terms of current efficiency and drive voltage compared to amperage elements.

Claims

1. The compound represented by the following chemical formula 1: 【Chemistry 1】 (In chemical formula 1, Multiple Xs may be the same or different from each other, and each can be independent of CR ２ Or N However, at least two of the multiple X values ​​are N. R ２ These are hydrogen, deuterium (D), halogen, cyano group, nitro group, and C １ ~C ４０ no Arki Ru group, C ２ ~C ４０ alkenyl group of, C ２ ~C ４０ alkynyl group of, C ３ ~C ４０ of cyclo cycloalkyl groups, heterocycloalkyl groups with 3 to 40 nuclear atoms, C ６ ~C ６０ Ariel Group, heteroaryl group with 5 to 60 nuclear atoms, C １ ~C ４０ The alkyloxy group, C ６ ~ C ６０ The aryloxy group, C ３ ~C ４０ alkylsilyl group, C ６ ~C ６０ Ariel Silyl group, C １ ~C ４０ alkylboron group, C ６ ~C ６０ The arylboron group, C ６ ~ C ６０ The arylphosphanyl group, C ６ ~C ６０ monoarylphosphenyl group, C ６ ~ C ６０ diarylphosphinyl group, C ６ ~C ６０ The arylamine group, C ５ ~C ６０ of Aryl heteroarylamine groups, and heteroarylamine groups with 5 to 60 nuclear atoms. Selected from the following groups, L is a single bond, or C ６ ~C １８ The arylene group and the heteronuclear group with 5 to 18 atoms. Selected from the group consisting of rielene groups, R １ C ６ ~C ６０ From the aryl group and the heteroaryl group with 5 to 60 nuclear atoms Selected from the following groups, m is an integer greater than or equal to 1, and n is an integer between 0 and 3. Ar ２ C １ ~C ４０ alkyl group, C ２ ~C ４０ The alkenyl group, C ２ ~C ４０ of Alkynyl group, C ３ ~C ４０ Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 nuclear atoms. Lukil group, C ６ ~C ６０ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C １ ~ C ４０ The alkyloxy group, C ６ ~C ６０ The aryloxy group, C ３ ~C ４０ alkyl Silyl group, C ６ ~C ６０ The arylsilyl group, C １ ~C ４０ alkylboron group, C ６ ~ C ６０ The arylboron group, C ６ ~C ６０ The arylphosphanyl group, C ６ ~C ６０ no mo Noarylphosphinyl group, C ６ ~C ６０ diarylphosphinyl group, C ６ ~C ６０ of Arylamine group, C ５ ~C ６０ The aryl heteroarylamine group, and the number of nuclear atoms is 5- Selected from a group consisting of 60 heteroarylamine groups, Ar １ This is the moiety represented by the following chemical formula 2. 【Chemistry 2】 (In chemical formula 2, * indicates the bonding site with chemical formula 1. Y is O, S, or NR １１ And, Circles A and B may be identical or different from each other, and each may independently contain heteroatoms. C does not contain or ５ ~C １８ It is a monocyclic or polycyclic hydrocarbon ring group, R １１ and R １２ They may be the same or different from each other, and each may be independent of C １ ~C １２ alkyl group, C ６ ~C １２ The aryl group and the heteroaryl group with 5 to 12 nuclear atoms. These may be lig groups, or they may bond with adjacent groups to form a fused ring. a is between 0 and 2. The above L is an arylene group and a heteroarylene group, and the above R １ The aryl group and hetero Aryl group, and the above R ２ , R １１ ~R １２ , and Ar ２ alkyl groups, alkenyl groups , alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl aryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, Alkylboron group, arylboron group, arylphosphanyl group, monoarylphosphine Nyl group, diarylphosphinyl group, arylamine group, arylheteroarylamine The group and the heteroarylamine group are each independently composed of deuterium (D), halogen, and cyanoacrylate. a base, a nitro group, C １ ~C ４０ alkyl group of, C ２ ~C ４０ alkenyl group of, C ２ ~C ４０ The alkynyl group, C ３ ~C ４０ Cycloalkyl groups, heterocyclo groups with 3 to 40 nuclear atoms. an alkyl group, C ６ ~C ６０ aryl group of, a heteroaryl group having 5 to 60 nuclear atoms, C １ ~C ４０ The alkyloxy group, C ６ ~C ６０ The aryloxy group, C １ ~C ４０ no Arki Lucilyl group, C ６ ~C ６０ The arylsilyl group, C １ ~C ４０ alkylboron group, C ６ ~C ６０ The arylboron group, C ６ ~C ６０ The arylphosphine group, C ６ ~C ６０ no A Reelphosphine oxide group, C ６ ~C ６０ The arylamine group, C ５ ~C ６０ Ally It consists of a heteroarylamine group and a heteroarylamine group with 5 to 60 nuclear atoms. It may be substituted with one or more substituents selected from the group, in which case the substituents are multiple If there are several, they may be identical or different from each other, provided they are substituted with substituents. Ar that is either present or not replaced １ The total number of carbon atoms contained in it is between 16 and 24.

2. The above Ar １ The is selected from the group of substituted compounds represented by the following chemical formulas, according to claim 1. The compounds listed: 【Transformation 3】 In the above chemical formula, * indicates the bonding site with the above chemical formula 1. Circles D may be identical or different from each other, and each independently may contain a heteroatom or It is a monocyclic or polycyclic hydrocarbon ring group that does not contain, Y and R １２ These are as defined in claim 1, respectively.

3. The above Ar １ The is selected from the group of substituted compounds represented by the following chemical formulas, according to claim 1. The compounds listed: 【Chemistry 4】 【Transformation 5】 【Transformation 6】 In the above chemical formula, R １１ and R １２ These are as defined in claim 1, respectively.

4. R １ C ６ ~C １２ It is an aryl group, m is an integer between 1 and 5. R is substituted or unsubstituted １ The total number of carbon atoms contained in it is small. The compound according to claim 1, wherein each compound has 18 elements.

5. The X-containing ring described above is selected from the group of substituted compounds represented by the following chemical formula, claim 1 The compounds listed: 【Transformation 7】 In the above chemical formula, * indicates the bonding site with the above chemical formula 1. R ２ Ar １ , and Ar ２ These are as defined in claim 1, respectively.

6. Ar ２ C ６ ~C ６０ The aryl group, and the heteroaryl group with 5 to 60 nuclear atoms. The compound according to claim 1, which is selected from the group.

7. The above Ar ２ The is selected from the group of substituted compounds represented by the following chemical formulas, according to claim 1. The compound described. 【Transformation 8】

8. The compound represented by the above chemical formula 1 is represented by any one of the following chemical formulas 3 to 9. The compound described in claim 1 is: 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 In the above chemical formula, X, Y, Ar ２ , R １ n and m are as defined in claim 1, respectively. Circle D is a monocyclic or polycyclic hydrocarbon ring group that may or may not contain a heteroatom.

9. The compound represented by the above chemical formula 1 is one of the following chemical formulas 10 to 21. The compound according to claim 1, which is represented by: 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 In the above chemical formula, X, Ar １ Ar ２ , L, R １ , and n are as defined in claim 1, respectively.

10. The compound represented by the above chemical formula 1 is also represented by one of the following chemical formulas 1 to 93. The compound according to claim 1, wherein the compound is as described above. 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 【Transformation 33】

11. The compound represented by the above chemical formula 1 is a material for a light-emitting layer, an electron transport layer, or an electron transport auxiliary layer. The compound according to claim 1.

12. The anode, cathode, and one or more organic layers interposed between the anode and cathode, the above 1 At least one of the organic layers of 1 or more layers is described in any one of claims 1 to 11. An organic electroluminescent element containing the compound shown.

13. The organic layer containing the above compound comprises a light-emitting layer, a light-emitting auxiliary layer, a hole injection layer, a hole transport layer, and an electron injection layer. It is selected from the group consisting of an infill layer, a life improvement layer, an electron transport layer, and an electron transport auxiliary layer. The organic electroluminescent element according to claim 12.

14. The above compound is a small portion of the phosphorescent host material of the light-emitting layer, the electron transport layer, and the electron transport auxiliary layer. The organic electroluminescence described in claim 13, which is included as at least one material. element.

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