Organic electroluminescent compound and organic electroluminescent device comprising the same

Abstract

Organic electroluminescent compounds and organic electroluminescent devices comprising the same. An organic electroluminescent device is provided, wherein an organic electroluminescent compound represented by the following formula 1 is included in an electron transport layer: --- (1).

Description

[0001] This invention patent application is a divisional application of the invention patent application entitled "Organic electroluminescent compound and organic electroluminescent device comprising the same". The application number is PCT / KR2019 / 003537, the application number entering the Chinese national phase is 201980016644.0, the application date is March 27, 2019. Technical Field

[0002] This disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. Background Technology

[0003] Electroluminescent devices (EL devices) are self-emissive display devices that offer advantages such as a wider viewing angle, a higher contrast ratio, and a faster response time. The first organic EL device was developed by Eastman Kodak in 1987 using small aromatic diamine molecules and aluminum complexes as materials for forming the luminescent layer [Appl. Phys. Lett. 51, 913, 1987].

[0004] The most important factor determining the luminescence efficiency in organic electroluminescent devices is the luminescent material. Fluorescent materials have been widely used as luminescent materials to date. However, given the electroluminescence mechanism, phosphorescent materials have been extensively studied because they theoretically enhance luminescence efficiency by four (4) times compared to fluorescent materials. Iridium (III) complexes are well-known as phosphorescent materials, including bis(2-(2'-benzothiophene)-pyridine-N,C-3')(acetylacetone)iridium[(acac)Ir(btp)2], tris(2-phenylpyridine)iridium[Ir(ppy)3], and bis(4,6-difluorophenylpyridine-N,C2)pyridinecarboxyiridium (Firpic), which are luminescent in red, green, and blue, respectively.

[0005] In conventional technologies, 4,4'-N,N'-dicarbazole-biphenyl (CBP) is the most well-known host material for phosphorescence. Recently, Pioneer Corporation (Japan) and others have developed a high-performance organic electroluminescent device using copper bath (BCP), a hole-blocking material, and aluminum(III)bis(2-methyl-8-quinoline) (4-phenylphenol) (BAlq) as host materials.

[0006] While these materials offer good luminescence characteristics, they have the following drawbacks: (1) Due to their low glass transition temperature and poor thermal stability, they may degrade during high-temperature deposition processes in a vacuum, potentially shortening the device's lifespan. (2) The power efficiency of organic electroluminescent devices is derived from [(π / voltage) × current efficiency], and power efficiency is inversely proportional to voltage. Although organic electroluminescent devices containing phosphorescent host materials offer higher current efficiency (cd / A) than those containing fluorescent materials, they require considerably higher driving voltages. Therefore, there is no advantage in terms of power efficiency (lm / W). (3) Furthermore, organic electroluminescent devices have short operating lifetimes, and there is still a need to improve luminescence efficiency.

[0007] Furthermore, electron transport materials actively transport electrons from the cathode to the emissive layer and suppress the transport of holes that have not recombinated in the emissive layer, thereby increasing the recombination opportunities between holes and electrons in the emissive layer. Therefore, electron affinity materials are used as electron transport materials. Organometallic complexes with luminescent properties, such as Alq3, are conventionally used as electron transport materials. However, Alq3 has the problem of migrating to other layers and exhibiting a decrease in color purity when used in devices emitting blue light. Therefore, there is a need for new electron transport materials that do not have the aforementioned problems, are highly electron-affinity, and rapidly transport electrons in organic EL devices to provide organic EL devices with high luminous efficiency.

[0008] Various materials or concepts for organic layers in organic electroluminescent devices have been proposed to improve luminous efficiency, driving voltage, and / or lifetime; however, their application in practical applications has not been satisfactory.

[0009] Korean Patent No. 1052973 B1 discloses fused benzimidazole derivatives as organic electroluminescent compounds. However, the aforementioned document does not disclose fused aza-indene derivatives, nor does it specifically disclose organic electroluminescent devices containing the aforementioned compounds. Summary of the Invention

[0010] Technical issues

[0011] The purpose of this disclosure is firstly to provide an organic electroluminescent compound that is effectively used to produce an organic electroluminescent device having a low driving voltage and / or high luminous efficiency, and secondly to provide an organic electroluminescent device comprising the organic electroluminescent compound.

[0012] Solution to the problem

[0013] Thin films made of materials with low glass transition temperatures may experience morphological deformation even at low temperatures due to heat generated during driving, and may reduce charge mobility in the film, thereby degrading the performance of the OLED device. In this regard, as a result of in-depth research, the inventors of this invention have discovered that the organic electroluminescent compounds of this disclosure can provide excellent structural and thermal stability by reducing internal steric hindrance. The compounds according to this disclosure have high glass transition temperatures (Tg) relative to their molecular weight due to their highly fused ring structure. Materials with high glass transition temperatures in OLEDs can be advantageous due to their good morphological stability. Specifically, the inventors of this invention have discovered that the above-mentioned objective can be achieved by an organic electroluminescent compound represented by the following formula: ---(1) in, At least one of R1, R2, and R3 is represented by the following equation 2: ---(2) in, L represents a single bond, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene, or a substituted or unsubstituted (C3-C30) cycloalkylene; Ar represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl (C (6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyl di(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino; R1 to R3 are each independently represented by Formula 2, or represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl (C6... -C30) arylsilyl, substituted or unsubstituted (C1-C30) alkylbis(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino; or may be linked with adjacent substituents to form a ring; p to r each independently represent an integer from 1 to 4; s and t each independently represent integers from 1 to 3; and When p to t is 2 or greater, each R1, each R2, each R3, each L, or each Ar can be the same or different.

[0014] Beneficial effects of the present invention

[0015] By using the organic electroluminescent compound according to the present disclosure, organic electroluminescent devices with low driving voltage and / or high luminous efficiency can be prepared. Attached Figure Description

[0016] Figure 1 The molecular structure of the core of the compound represented by Formula 1 of this disclosure is shown in 3D form.

[0017] Figure 2 The molecular structure of the core of a conventional compound in 3D form is shown. Detailed Implementation

[0018] This disclosure will now be described in detail. However, the following description is intended to explain the invention and is not intended to limit the scope of the invention in any way.

[0019] The term "organic electroluminescent compound" in this disclosure means a compound that can be used in an organic electroluminescent device and, if necessary, can be included in any material layer constituting the organic electroluminescent device.

[0020] The term "organic electroluminescent material" in this disclosure refers to a material that can be used in an organic electroluminescent device and may contain at least one compound. If desired, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material, etc.

[0021] The organic electroluminescent material disclosed herein may comprise at least one of the compounds represented by Formula 1 above. The organic electroluminescent compound having Formula 1 may be included in the luminescent layer and / or the electron transport layer, but is not limited thereto. When used in the luminescent layer, the organic electroluminescent compound having Formula 1 may be included as a host, and when used in the electron transport layer, the organic electroluminescent compound having Formula 1 may be included as an electron transport material.

[0022] In this document, "(C1-C30)alkyl" refers to a straight-chain or branched alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The aforementioned alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. "(C2-C30)alkenyl" refers to a straight-chain or branched alkenyl group having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The aforementioned alkenyl group may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. "(C2-C30)ynyl" refers to a straight-chain or branched ynyl group having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The aforementioned alkynyl groups may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpentan-2-ynyl, etc. "(C3-C30)cycloalkylene" is a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms in its cyclic skeleton, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The aforementioned cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. "(3- to 7-membered)heterocyclic alkylene" is a cycloalkyl group having 3 to 7, preferably 5 to 7, cyclic skeleton atoms, including at least one heteroatom selected from B, N, O, S, Si, and P, and preferably O, S, and N. The aforementioned heteroalkyl groups may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, etc.

[0023] "(C6-C30) (aryl) group" is a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in the ring skeleton, wherein the number of carbon atoms in the ring skeleton is preferably 6 to 25, more preferably 6 to 18, and may be partially saturated and may contain a spirostructure. Examples of aryl groups include phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, binatyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzo[fluorenyl], diphenylbenzo[fluorenyl], dibenzo[fluorenyl], phenanthrene, benzo[phenanthrene], phenylphenanthrene, anthracene, benzo[anthrene], indole, triphenylene, pyrene, tetraphenyl, perylene, benzo[benzo[fluorenyl], naphthyl, fluoranyl, benzo[fluoranyl], tolyl, xylene, mesitylene, isopropylphenyl, spiro[fluorenyl-fluorenyl], spiro[fluorenyl-benzo[fluorenyl]], azulene, etc. More specifically, the aryl group can be o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylelel, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4'-tert-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-tetraphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9, 9-Dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 1-anthrayl, 2-anthrayl, 9-anthrayl, 1-phenanthyl, 2 -Phenylenyl, 3-Phenylenyl, 4-Phenylenyl, 9-Phenylenyl, 1-Hylenyl, 2-Hylenyl, 3-Hylenyl, 4-Hylenyl, 5-Hylenyl, 6-Hylenyl, benzo[c]phenylenyl, benzo[g]Hylenyl, 1-Tripylenyl, 2-Tripylenyl, 3-Tripylenyl, 4-Tripylenyl, 3-Fluoranthryl, 4-Fluoranthryl, 8-Fluoranthryl, 9-Fluoranthryl, benzo[fluoranthryl], etc.

[0024] "(3- to 30-membered) (hybrid)aryl" is an aryl group having 3 to 30 cyclic skeleton atoms, comprising at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, P, and Ge. The heteroaryl group can be monocyclic or a fused ring condensed with at least one benzene ring; and can be partially saturated. The heteroatoms can be linked to at least one substituent selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (5- to 30-membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted dialkylsilyl, etc. (C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-30)arylamino. Furthermore, the aforementioned heteroaryl groups can be heteroaryl groups formed by attaching at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds; and may contain a spirostructure. Examples of heteroaryl groups specifically include monocyclic heteroaryl groups, including furanyl, thiopheneyl, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazonyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc.; and fused-ring heteroaryl groups, including benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl, dibenzothiopheneyl, benzimidazolyl, etc. Benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridyl, isoindolyl, indolyl, benzoindolyl, indazole, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinolinyl, quinazolinyl, quinoxolinyl, carbazole, azacarbazole, benzocarbazole, dibenzocarbazole, phenoxazinyl, phenanthidyl, benzodioxacyclopentenyl, indolizidyl, acrylidine, silylfluorenyl, germanylfluorenyl, etc. More specifically, the heteroaryl group can be 1-pyrrolithyl, 2-pyrrolithyl, 3-pyrrolithyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidyl, 2-indolizidyl, 3-indolizidyl, 5-indolizidyl, 6-indolizidyl, 7-indolizidyl, 8-indolizidyl,2-Imidazolopyridyl, 3-Imidazolopyridyl, 5-Imidazolopyridyl, 6-Imidazolopyridyl, 7-Imidazolopyridyl, 8-Imidazolopyridyl, 1-Indolyl, 2-Indolyl, 3-Indolyl, 4-Indolyl, 5-Indolyl, 6-Indolyl, 7-Indolyl, 1-Isoindolyl, 2-Isoindolyl, 3-Isoindolyl, 4-Isoindolyl, 5-Isoindolyl, 6-Isoindolyl, 7-Isoindolyl, 2-Furanyl, 3-Furanyl, 2-Benzofuranyl, 3-Benzofuranyl, 4-Benzofuranyl, 5-Benzofuranyl, 6-Benzofuranyl, 7-Benzofuranyl, 1-Isobenzofuranyl, 3-Isobenzofuranyl, 4-Isobenzofuranyl, 5-Isobenzofuranyl Furanyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, 4-carbazoleyl, 9-carbazoleyl, azacarbazole-1-yl, azacarbazole-2-yl, azacarbazole-3-yl, azacarbazole-4-yl, azacarbazole-5-yl, azacarbazole-6-yl, azacarbazole-7-yl, azacarbazole-8-yl, nitrogen Xacarbazole-9-yl, 1-phenanthridyl, 2-phenanthridyl, 3-phenanthridyl, 4-phenanthridyl, 6-phenanthridyl, 7-phenanthridyl, 8-phenanthridyl, 9-phenanthridyl, 10-phenanthridyl, 1-acridyl, 2-acridyl, 3-acridyl, 4-acridyl, 9-acridyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrole-1-yl, 2-methylpyrrole-3-yl, 2-methylpyrrole-4-yl, 2-methylpyrrole-5-yl, 3-methylpyrrole-1-yl, 3-methylpyrrole-2-yl, 3-methylpyrrole-4-yl, 3-methylpyrrole-5-yl, 2-tert-butylpyrrole 4-pyrroloyl, 3-(2-phenylpropyl)pyrroloyl-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-diphenyl Fiberyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-siliconyl, 2-siliconyl, 3-siliconyl, 4-siliconyl, 1-germanium fluorenyl, 2-germanium fluorenyl, 3-germanium fluorenyl, and 4-germanium fluorenyl, etc.

[0025] Halogens include F, Cl, Br, and I.

[0026] Furthermore, "ortho (o)," "meta (m)," and "para (p)" indicate the substitution positions of all substituents. The ortho position is a compound with substituents adjacent to each other, such as at positions 1 and 2 on benzene. The meta position is the next substitution position after the immediately adjacent substitution position; for example, a compound with substituents at positions 1 and 3 on benzene. The para position is the next substitution position after the meta position; for example, a compound with substituents at positions 1 and 4 on benzene.

[0027] In this document, "a ring formed by linking with adjacent substituents" refers to a substituted or unsubstituted (3-membered to 30-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or combination thereof formed by linking or fused two or more adjacent substituents; preferably, it can be a substituted or unsubstituted (3-membered to 26-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or combination thereof. Furthermore, at least one carbon atom in the formed ring can be replaced by at least one heteroatom selected from B, N, O, S, Si, and P, preferably from the group consisting of N, O, and S. According to one embodiment, the ring formed by linking with adjacent substituents can be a (5-membered to 20-membered) polycyclic aromatic ring, which may contain at least one heteroatom selected from the group consisting of N, O, and S.

[0028] Furthermore, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or functional group (i.e., a substituent). Substituted (C1-C30)alkyl, substituted (C6-C30)(aryl)alkyl, substituted (3- to 30-membered)(heteroaryl), substituted (C3-C30)(cycloalkyl)alkyl, substituted (C1-C30)alkoxy, substituted tri(C1-C30)alkylsilyl, substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted tri(C6-C30)arylsilyl, substituted mono- or The substituents of the di-(C1-C30)alkylamino, substituted mono- or di-(C6-C30)arylamino, and substituted (C1-C30)alkyl(C6-C30)arylamino groups are each independently selected from at least one of the following groups: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, ( (3- to 7-membered) heterocyclic alkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (C6-C30) aryl-substituted or unsubstituted (3- to 30-membered) heteroaryl, (3- to 30-membered) heteroaryl-substituted or unsubstituted (C6-C30) aryl, tri(C1-C30) alkylsilyl, tri(C6-C30) arylsilyl, di(C1-C30) alkyl(C6-C30) arylsilyl, (C1-C30) alkyldi(C6-C30) arylsilyl, amino, mono- or di-(C1-C30) alkylamino The substituents are mono- or di-(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylborylcarbonyl, di(C1-C30)alkylborylcarbonyl, (C1-C30)alkyl(C6-C30)arylborylcarbonyl, (C6-C30)aryl(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl. According to one embodiment, each substituent is independently at least one selected from (C1-C6)alkyl, (C6-C15)aryl, and (5- to 15-membered) heteroaryl. Specifically, each of the substituents can be at least one of methyl, phenyl, naphthyl, biphenyl, dibenzothiophene, and dibenzofuranyl.

[0029] Organic electroluminescent compounds having Formula 1 can be represented by any one of the following Formulas 1-1 to 1-3: ---(1-1) ---(1-2) ---(1-3) In equations 1-1 to 1-3, L, Ar, R1 to R3 and p to t are defined as in Equation 1.

[0030] In Equation 1, at least one of R1, R2, and R3 is represented by Equation 2: ---(2) In Formula 2, L represents a single bond, a substituted or unsubstituted (C6-C30) arylene, a substituted or unsubstituted (3- to 30-membered) heteroarylene, or a substituted or unsubstituted (C3- to C30) cycloalkylene. In one embodiment of this disclosure, L represents a single bond, a substituted or unsubstituted (C6-C15) arylene, or a substituted or unsubstituted (5- to 15-membered) heteroarylene. In another embodiment of this disclosure, L represents a single bond, an unsubstituted (C6-C15) arylene, or an unsubstituted (5- to 15-membered) heteroarylene. Specifically, L represents a single bond, phenylene, naphthylene, biphenylene, pyridylene, pyrimidinyl, triazineyl, quinazolinyl, quinoxalinyl, benzoquinoxalinyl, etc.

[0031] In Formula 2, Ar represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl. (C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino. In one embodiment of this disclosure, Ar represents substituted or unsubstituted (C6-C20)aryl, substituted or unsubstituted (5- to 15-membered) heteroaryl, or substituted or unsubstituted di(C6-C15)arylamino. In another embodiment of this disclosure, Ar represents (C1-C6) alkyl-substituted or unsubstituted (C6-C20) aryl, unsubstituted (5- to 15-membered) heteroaryl, or (C1-C6) alkyl-substituted or unsubstituted di(C6-C15) arylamino. Specifically, Ar can be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthylphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted fluoranyl group, a substituted or unsubstituted triazine group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted benzothiophene-pyrimidinyl group, a substituted or unsubstituted acenaphthopyrimidinyl group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted benzoquinazoline group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted dibenzoquinoxalinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, or a substituted or unsubstituted isoquinoxalinyl group. Substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted benzothiophenequinolinyl, substituted or unsubstituted benzofuranoquinolinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphridyl, substituted or unsubstituted benzothiazolinyl, substituted or unsubstituted phenanthimidazole, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylbiphenylamino, substituted or unsubstituted fluorenylphenylamino, substituted or unsubstituted dibenzothiophene phenylamino, or substituted or unsubstituted dibenzofuranylphenylamino, etc.

[0032] In Formula 1, R1 to R3 are each independently represented by Formula 2, or represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-membered to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl. (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl, substituted or unsubstituted mono- or di-(C1-C30) alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl(C6-C30) arylamino; or may be linked with adjacent substituents to form a ring. In one embodiment of this disclosure, R1 to R3 are each independently represented by Formula 2, or represent hydrogen, substituted or unsubstituted (C6-C15) aryl, or substituted or unsubstituted (5-membered to 15-membered) heteroaryl; or may be linked with adjacent substituents to form a ring. In another embodiment of this disclosure, R1 to R3 are each independently represented by Formula 2, or represent hydrogen, an unsubstituted (C6-C15) aryl, or an unsubstituted (5-membered to 15-membered) heteroaryl; or they may be connected with adjacent substituents to form a ring. Specifically, R1 to R3 can each be independently hydrogen, phenyl, pyridyl, or dibenzofuranyl; or they may be connected with adjacent substituents to form a ring. For example, two adjacent R1s, two adjacent R2s, two adjacent R3s, R1 and R2, R2 and R3, and / or R1 and R3 can be connected to each other to form one or more fused rings with adjacent substituents.

[0033] When at least one of R1 to R3 can be connected with an adjacent substituent to form a ring, at least one ring having the following formulas 3 to 7 can be formed.

[0034] ---(3) ---(4) ---(5) ---(6) ---(7) In equations 6 and 7, R4 to R6 each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and R5 and R6 may be linked to form a ring.

[0035] In Equation 1, p to r each independently represent an integer from 1 to 4; in Equation 2, s and t each independently represent an integer from 1 to 3. When p to t are 2 or greater, each R1, each R2, each R3, each L, or each Ar can be the same or different. In one embodiment of this disclosure, p to s each independently represent 1 or 2; t represents 1 to 3.

[0036] According to one embodiment of this disclosure, in Formulas 1 and 2, L represents a single bond, a substituted or unsubstituted (C6-C15) aryl group, or a substituted or unsubstituted (5- to 15-membered) heteroaryl group; Ar represents a substituted or unsubstituted (C6-C20) aryl group, a substituted or unsubstituted (5- to 15-membered) heteroaryl group, or a substituted or unsubstituted di(C6-C15) arylamino group; R1 to R3 are each independently represented by Formula 2, or represent hydrogen, a substituted or unsubstituted (C6-C15) aryl group, or a substituted or unsubstituted (5- to 15-membered) heteroaryl group; or may be connected with adjacent substituents to form a ring.

[0037] According to another embodiment of this disclosure, in Formulas 1 and 2, L represents a single bond, an unsubstituted (C6-C15) aryl group, or an unsubstituted (5- to 15-membered) heteroaryl group; Ar represents a (C1-C6) alkyl-substituted or unsubstituted (C6-C20) aryl group, an unsubstituted (5- to 15-membered) heteroaryl group, or a (C1-C6) alkyl-substituted or unsubstituted di(C6-C15) arylamino group; R1 to R3 are each independently represented by Formula 2, or represent hydrogen, an unsubstituted (C6-C15) aryl group, or an unsubstituted (5- to 15-membered) heteroaryl group; or may be connected with adjacent substituents to form a ring.

[0038] In the formulas of this disclosure, when adjacent substituents are linked together to form a ring, the ring may be a substituted or unsubstituted (3-membered to 30-membered) monocyclic or polycyclic alicyclic or aromatic ring, or a combination thereof. Furthermore, the formed ring may contain at least one heteroatom selected from nitrogen, oxygen, and sulfur.

[0039] In the formula disclosed herein, each (hetero)aryl group may independently contain at least one heteroatom selected from B, N, O, S, Si, and P. Furthermore, the heteroatom may be linked to at least one substituent selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (5-membered to 30-membered)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted... Di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-30)arylamino.

[0040] The compounds represented by Formula 1 can be further illustrated by the following compounds, but are not limited to: .

[0041] The compounds having Formula 1 according to this disclosure can be produced by synthetic methods known to those skilled in the art and, for example, by referring to the following reaction scheme, but are not limited thereto: [Reaction Scheme 1]

[0042] [Reaction Scheme 2]

[0043] [Reaction Scheme 3]

[0044] [Reaction Scheme 4]

[0045] [Reaction Scheme 5]

[0046] In reaction schemes 1 to 5, R1 to R3 and p to r are as defined in Equation 1.

[0047] As described above, exemplary synthetic examples of compounds represented by Formula 1 according to one embodiment have been described, but they are based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-montage-mediated etherification reactions, Miyaura borylation reactions, Suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, Pd(II)-catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, dehydration cyclization reactions, SN1 substitution reactions, SN2 substitution reactions, and phosphine-mediated reductive cyclization reactions, etc. Those skilled in the art will understand that the above reactions will continue even if other substituents defined in Formula 1 are bonded besides those described in the specific synthetic examples.

[0048] This disclosure provides an organic electroluminescent material comprising an organic electroluminescent compound having Formula 1, and an organic electroluminescent device comprising said organic electroluminescent material. The material may consist solely of the organic electroluminescent compound of this disclosure, or may further comprise conventional materials commonly used in organic electroluminescent materials.

[0049] Furthermore, this disclosure provides a composite material for an organic electroluminescent device, comprising a compound having Formula 1 and at least one type of organic electroluminescent compound.

[0050] The organic electroluminescent device according to this disclosure includes a first electrode; a second electrode; and at least one organic layer inserted between the first electrode and the second electrode. The organic layer may contain at least one organic electroluminescent compound having Formula 1. The organic layer may further contain at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds. Furthermore, in the organic electroluminescent device of this disclosure, the organic layer may further contain at least one metal selected from the group consisting of: metals of Group 1, Group 2, transition metals of Period 4, transition metals of Period 5, lanthanides, and organometallic compounds of d-transition elements, or at least one complex compound containing such metal.

[0051] According to one embodiment, the organic electroluminescent material can be used as a luminescent material for white organic light-emitting devices. Various structures have been proposed for white organic light-emitting devices based on the arrangement of R (red), G (green), B (blue), or YG (yellow-green) luminescent units, such as parallel side-by-side arrangements, stacked arrangements, or CCM (color conversion material) methods. Furthermore, the organic electroluminescent material according to one embodiment can also be applied to organic electroluminescent devices containing QDs (quantum dots).

[0052] One of the first electrode and the second electrode can be an anode, and the other can be a cathode. The first electrode and the second electrode can each be formed using a transmissive conductive material, a transmissive-reflective conductive material, or a reflective conductive material. Depending on the type of material forming the first electrode and the second electrode, the organic electroluminescent device can be a top-emitting, bottom-emitting, or side-emitting type. The organic layer can include a light-emitting layer, and may further include at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer.

[0053] The organic electroluminescent compound having Formula 1 can be contained in at least one of the following layers: a light-emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. Preferably, the organic electroluminescent compound represented by Formula 1 can be contained in at least one of the light-emitting layer and the electron transport layer. When used in the light-emitting layer, the organic electroluminescent compound having Formula 1 can be contained as a host material. When used in the electron transport layer, the organic electroluminescent compound having Formula 1 can be contained as an electron transport material. If desired, the organic electroluminescent compound of this disclosure can be used as a co-host material. That is, the light-emitting layer can further contain compounds other than the organic electroluminescent compound having Formula 1 of this disclosure (the first host material) as a second host material. In this document, the weight ratio of the first host material to the second host material is 1:99 to 99:1.

[0054] The second host material can be any known host material, and the second host material can preferably be a compound represented by formulas 21 to 23 below: ---(twenty one) ---(twenty two) ---(twenty three) In equations 21 to 23, Ma represents substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted mono- or di-(C6-C30) arylamino, or substituted or unsubstituted (3- to 30-membered) heteroaryl; La represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; A represents S, O, NR7, or CR8R9; Ra to Rd each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) ynyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or Unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or substituted or unsubstituted mono- or di-(C6-C30)arylamino; or may be linked with adjacent substituents to form a ring; R7 to R9 independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) ) arylsilyl, substituted or unsubstituted (C1-C30)alkylbis(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; and R8 and R9 may be linked to each other to form a ring; a to c each independently represent integers from 1 to 4, and d represents integers from 1 to 3; and The (hybrid)aryl group contains at least one heteroatom selected from B, N, O, S, Si, and P.

[0055] Specifically, a compound represented by any one of formulas 21 to 23 can be described by, but is not limited to, the following compounds: .

[0056] [Where TPS stands for triphenylsilyl]

[0057] The dopant included in the organic electroluminescent device of this disclosure may be at least one phosphorescent dopant or fluorescent dopant. Preferably, the phosphorescent dopant material used in the organic electroluminescent device of this disclosure is not particularly limited, but it may preferably be one or more metallized complexes of one or more metal atoms selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably one or more ortho-metallized complexes of one or more metal atoms selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and even more preferably one or more ortho-metallized iridium complexes.

[0058] The dopants included in the organic electroluminescent devices of this disclosure may be compounds represented by formula 101, but are not limited thereto: ---(101) In Equation 101, Wherein, L is selected from either structure 1 or 2: ---Structure (1) ---Structure (2) R 100 To R 103 Each independently represents hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or R 100 To R 103It can be linked with adjacent substituents to form substituted or unsubstituted fused rings, such as substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothiophenopyridine, substituted or unsubstituted indenepyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothiophenoquinoline, or substituted or unsubstituted indenequinoline; R 104 To R 107 Each of these elements independently represents hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or R 104 To R 107 It can be linked to adjacent substituents to form substituted or unsubstituted fused rings with benzene, such as substituted or unsubstituted naphthyl, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indopyridine, substituted or unsubstituted benzofuran-pyridine, or substituted or unsubstituted benzothiophene-pyridine. R 201 To R 211 Each independently represents hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or R 201 To R 211 It can connect with adjacent substituents to form substituted or unsubstituted fused rings; and n represents an integer from 1 to 3.

[0059] Specific examples of dopant compounds include, but are not limited to, the following: .

[0060] Furthermore, the organic electroluminescent device of this disclosure, in addition to the compounds disclosed herein, further includes at least one luminescent layer comprising a blue, red, or green luminescent compound known in the art, such that the organic electroluminescent device can emit white light. Additionally, if desired, it may further include a yellow or orange luminescent layer. In the organic electroluminescent device of this disclosure, preferably, at least one layer selected from chalcogenide layers, metal halide layers, and metal oxide layers (hereinafter, "surface layer") may be placed on one or more inner surfaces of one or two electrodes. Specifically, it is preferred to place silicon and aluminum chalcogenide (including oxide) layers on the anode surface of the electroluminescent dielectric layer, and preferably to place a metal halide layer or metal oxide layer on the cathode surface of the electroluminescent dielectric layer. The operational stability of the organic electroluminescent device can be achieved through the surface layer. Preferably, the chalcogenide includes SiO₂. X (1 ≤ X ≤ 2), AlO X (1 ≤ X ≤ 1.5), SiON, SiAlON, etc.; metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc.; and metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0061] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. The hole injection layer can be multilayered to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, wherein each of the multilayers can use two compounds simultaneously. The hole transport layer or electron blocking layer can be multilayered. Furthermore, the hole injection layer can be doped with a p-type dopant.

[0062] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. The electron buffer layer can be multilayered to control electron injection and improve the interface properties between the light-emitting layer and the electron injection layer, wherein each of the multilayers can use two compounds simultaneously. The hole blocking layer or electron transport layer can also be multilayered, wherein each layer can use multiple compounds. Furthermore, the electron injection layer can be doped with an n-type dopant.

[0063] A light-emitting auxiliary layer can be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When placed between the anode and the light-emitting layer, it can promote hole injection and / or hole transport, or prevent electron overflow. When placed between the cathode and the light-emitting layer, it can promote electron injection and / or electron transport, or prevent hole overflow. Furthermore, a hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can effectively promote or limit the hole transport rate (or hole injection rate), thereby enabling charge balance control. When an organic electroluminescent device includes two or more hole transport layers, the further included hole transport layers can serve as hole auxiliary layers or electron blocking layers. The light-emitting auxiliary layer, hole auxiliary layer, or electron blocking layer can improve the efficiency and / or lifetime of the organic electroluminescent device.

[0064] In the organic electroluminescent device of this disclosure, a mixed region of electron transport compound and reducing dopant, or a mixed region of hole transport compound and oxidizing dopant, can be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anion, and thus it becomes easier to inject and transport electrons from the mixed region into the electroluminescent medium. Furthermore, the hole transport compound is oxidized to cation, and thus it becomes easier to inject and transport holes from the mixed region into the electroluminescent medium. Preferably, the oxidizing dopant includes various Lewis acids and acceptor compounds, and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reducing dopant layer can be used as a charge-generating layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.

[0065] To form each layer of the organic electroluminescent device of this disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating, etc., or wet film-forming methods such as spin coating, dip coating, flow coating, etc., can be used. When forming layers from the first and second host compounds of this disclosure, co-evaporation or mixed evaporation can be used.

[0066] When using a wet film-forming method, a thin film can be formed by dissolving or diffusing the material forming each layer into any suitable solvent (such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent can be any solvent in which the material forming each layer can dissolve or diffuse and in which there are no problems with film-forming ability.

[0067] Furthermore, the organic electroluminescent device disclosed herein can be used to manufacture display devices such as smartphones, tablets, laptops, PCs, TVs, or vehicle display devices, or lighting devices such as outdoor or indoor lighting.

[0068] In the following, the preparation methods of the main compounds according to the present disclosure and the characteristics of the apparatus comprising them will be explained in detail with reference to representative compounds of the present disclosure in order to provide a detailed understanding of the present disclosure.

[0069] [Example 1] Preparation of compound A-21

[0070] 1) Preparation of Compound 1

[0071] Benzaldehyde (80 g, 666 mmol), N-bromosuccinimide (118.5 g, 666 mmol), p-toluenesulfonic acid monohydrate (190 g, 999 mmol), and 1000 mL of acetonitrile were added to a flask and dissolved, and then refluxed at 130°C for 2 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate. The residual water was removed with magnesium sulfate and then dried, and then purified by column chromatography to obtain compound 1 (120 g, yield: 91%).

[0072] 2) Preparation of compound 2

[0073] Compound 1 (120 g, 603 mmol), 2-aminopyridine (58 g, 904 mmol), sodium bicarbonate (50 g, 603 mmol), and 2,000 mL of ethanol were added to a flask and dissolved, and then refluxed for 2 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate. The residual water was removed with magnesium sulfate and then dried, and then purified by column chromatography to obtain compound 2 (81.3 g, yield: 56%).

[0074] 3) Preparation of compound 3

[0075] Compound 2 (81.3 g, 419 mmol), N-bromosuccinimide (89.4 g, 502 mmol), and 1,100 mL of acetonitrile were added to a flask and refluxed at room temperature for 3 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate. The residual water was removed with magnesium sulfate and then dried, and subsequently purified by column chromatography to obtain compound 3 (110 g, yield: 96%).

[0076] 4) Preparation of compound 4

[0077] Compound 3 (110 g, 403 mmol), 2,4-dichlorophenylboronic acid (92 g, 483 mmol), tetrakis(triphenylphosphine)palladium(0) (23 g, 20 mmol), potassium carbonate (139 g, 1007 mmol), 1,800 mL of toluene, 710 mL of ethanol, and 710 mL of water were added to a flask and dissolved. The mixture was then refluxed at 120°C for 12 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate. The residual water was removed with magnesium sulfate and then dried. The mixture was then purified by column chromatography to obtain compound 4 (109.5 g, yield: 56%).

[0078] 5) Preparation of compound 5

[0079] Compound 4 (30 g, 88 mmol), 2,4-dimethyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl]1,3,5-triazine (46 g, 106 mmol), tetrakis(triphenylphosphine)palladium(0) (5 g, 4 mmol), potassium carbonate (31 g, 138 mmol), 440 mL of toluene, 110 mL of ethanol, and 110 mL of water were added to a flask and dissolved. The mixture was then refluxed at 120°C for 12 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate. The residual water was removed with magnesium sulfate and then dried. The mixture was then purified by column chromatography to obtain compound 5 (7.8 g, yield: 14%).

[0080] 6) Preparation of compound A-21

[0081] Compound 5 (7.6 g, 12 mmol), palladium(II) acetate (0.56 g, 2 mmol), tricyclohexylphosphine tetrafluoroborate (1.8 g, 5 mmol), cesium carbonate (12 g, 37 mmol), and 60 mL of dimethylacetamide (DMA) were added to a flask and dissolved, and then refluxed at 130°C for 12 hours. After the reaction was complete, the solvent was removed, and the mixture was then purified by column chromatography to obtain compound A-21 (3.5 g, yield: 49%).

[0082]

[0083] [Example 2] Preparation of compound A-19

[0084] 1) Preparation of compounds 1 to 4

[0085] Same as Example 1.

[0086] 2) Preparation of compound 6

[0087] Compound 4 (30 g, 88 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2-bis(1,3,2-dioxacyclopentaborane) (27 g, 106 mmol), tris(dibenzylacetone)dipalladium(0) (4 g, 4 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (s-phos) (3.6 g, 9 mmol), potassium acetate (22 g, 221 mmol), and 440 mL of 1,4-dioxane were added to a flask and refluxed at 120°C for 12 h. After the reaction was complete, the organic layer was extracted with ethyl acetate. The residual water was removed with magnesium sulfate and then dried, and subsequently purified by column chromatography to obtain compound 6 (36.1 g, yield: 95%).

[0088] 3) Preparation of compound 7

[0089] Compound 6 (35.5 g, 82 mmol), 1-([1,1'-biphenyl]3-yl)4-chloro-6-phenyl-1,3,5-triazine (23.6 g, 69 mmol), tetrakis(triphenylphosphine)palladium(0) (4 g, 3.4 mmol), potassium carbonate (24 g, 172 mmol), 340 mL of toluene, 86 mL of ethanol, and 86 mL of water were added to a flask and refluxed at 120°C for 12 hours. After the reaction was complete, the organic layer was extracted with ethyl acetate. The residual water was removed with magnesium sulfate and then dried, and subsequently purified by column chromatography to obtain compound 7 (10.3 g, yield: 25%).

[0090] 4) Preparation of compound A-19

[0091] Compound 7 (9.8 g, 16 mmol), palladium(II) acetate (0.72 g, 3 mmol), tricyclohexylphosphine tetrafluoroborate (2.4 g, 6 mmol), cesium carbonate (15.7 g, 48 mmol), and 80 mL of DMA were added to a flask and dissolved. The mixture was then refluxed at 130°C for 12 hours. After the reaction was complete, the solvent was removed, and the mixture was subsequently purified by column chromatography to obtain compound A-19 (1.7 g, yield: 18%).

[0092]

[0093] [Device Example 1] Production of an organic electroluminescent device emitting blue light according to this disclosure

[0094] An OLED device comprising the compounds disclosed herein is produced. First, a transparent electrode indium tin oxide (ITO) film (10 Ω / sq) (GEOMATEC CO., LTD., Japan) on a glass substrate for the OLED device is subjected to ultrasonic washing sequentially with acetone and isopropanol, and then stored in isopropanol. The ITO substrate is then mounted on a substrate holder of a vacuum phase deposition apparatus. Compound HI-1 is introduced into the chamber of the vacuum phase deposition apparatus, and the pressure in the chamber is then controlled to 10 Ω / sq. -7 The process involves applying a current to a chamber to evaporate the introduced material, thereby forming a first hole injection layer with a thickness of 60 nm on the ITO substrate. Next, compound HI-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying a current to the chamber, thereby forming a second hole injection layer with a thickness of 5 nm on the first hole injection layer. Then, compound HT-1 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying a current to the chamber, thereby forming a first hole transport layer with a thickness of 20 nm on the second hole injection layer. Then, compound HT-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying a current to the chamber, thereby forming a second hole transport layer with a thickness of 5 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer is formed thereon as follows: compound BH-1 is introduced as the host in one chamber of the vacuum vapor deposition apparatus, and compound BD-1 is introduced as a dopant in the other chamber. Two materials were evaporated at different rates, and a dopant was deposited at a dopant concentration of 2 wt% based on the total weight of the host and dopant to form a 20 nm thick light-emitting layer on the second hole transport layer. Next, as an electron transport material, compound A-21 was introduced into one chamber and compound EIL-1 into another chamber, and A-21 and EIL-1 were evaporated at a 1:1 ratio and deposited to form a 35 nm thick electron transport layer on the light-emitting layer. After depositing compound EIL-1 as a 2 nm thick electron injection layer on the electron transport layer, an 80 nm thick Al cathode was deposited on the electron injection layer using another vacuum phase deposition apparatus. Thus, an OLED device was produced. All materials used in the production of the OLED device were used in 10... -6 Purification is achieved through vacuum sublimation.

[0095] Table 1 below provides the driving voltage, efficiency, and color coordinates of the OLED device manufactured above at a brightness of 1,000 nits.

[0096] [Comparative Example 1] Production of an organic electroluminescent device that emits blue light and contains conventional organic electroluminescent compounds.

[0097] The OLED device was manufactured in the same manner as in Device Example 1, except that the electronic materials listed in Table 1 below were used instead of compound A-21 as the electron transport material. The evaluation results of the organic electroluminescent device of Comparative Example 1 are shown in Table 1 below.

[0098] Table 1

[0099] It can be confirmed that the performance of device example 1 is better than that of comparative example 1. The polarizability of the core of the disclosed compound is greater than that of the core of the conventional compound (disclosed in Korean Patent No. 1052973). The polarizability of the core can help to achieve π-π stacking in the vacuum deposition layer, thereby producing a faster charge mobility (not limited to theory).

[0100] Reference Figure 2 In the core of a conventional compound, one of the two nitrogen atoms (N2) is contained within phenanthrene, causing deformation due to steric hindrance between the hydrogen atoms of H1 and H2 (computer-calculated polarizability ratio: 240.030). In contrast, as... Figure 1 As shown, the core of the compounds of the present invention has a fused nitrogen-indene structure, thereby reducing steric hindrance (computer-calculated polarizability ratio: 247.080). Therefore, the compounds of the present invention can possess structural and thermal stability.

[0101] [Device Example 2] Production of an organic electroluminescent device wherein a compound according to the present disclosure is co-deposited as the host.

[0102] An OLED device comprising the compounds disclosed herein is produced. First, a transparent electrode indium tin oxide (ITO) film (10 Ω / sq) (Geoma Ltd., Japan) on a glass substrate for the OLED device is subjected to ultrasonic washing sequentially with acetone, ethanol, and distilled water, and then stored in isopropanol. The ITO substrate is then mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 is introduced into the chamber of the vacuum vapor deposition apparatus, and the pressure in the chamber is then controlled to 10 Ω / sq. -6The introduced material is then evaporated by applying current to a chamber, forming a first hole injection layer with a thickness of 80 nm on the ITO substrate. Next, compound HI-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying current to the chamber, forming a second hole injection layer with a thickness of 5 nm on the first hole injection layer. Then, compound HT-1 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying current to the chamber, forming a first hole transport layer with a thickness of 10 nm on the second hole injection layer. Then, compound HT-3 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying current to the chamber, forming a second hole transport layer with a thickness of 30 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer is formed thereon as follows: compounds H-8 and A-21 are introduced as hosts into one chamber of the vacuum vapor deposition apparatus, and compound D-50 is introduced as a dopant into another chamber. Two host materials were evaporated at a different rate of 2:1, and a dopant was deposited at a dopant concentration of 10 wt% based on the total weight of the host and dopant to form a 40 nm thick light-emitting layer on the second hole transport layer. Next, as an electron transport material, compound ETL-1 was introduced into one chamber and compound EIL-1 into another chamber, and ETL-1 and EIL-1 were evaporated at a rate of 4:6 and deposited to form an electron transport layer with a thickness of 35 nm on the light-emitting layer. After depositing compound EIL-1 as an electron injection layer with a thickness of 2 nm on the electron transport layer, an 80 nm thick Al cathode was deposited on the electron injection layer using another vacuum vapor deposition apparatus. Thus, an OLED device was produced.

[0103] The results show that an efficiency of 60.7 cd / A and 1000 nits of green light emission can be confirmed at a driving voltage of 2.9 V.

[0104] [Comparative Example 2] Production of an organic electroluminescent device in which conventional compounds are co-deposited as the host.

[0105] In addition to being used as a light-emitting material, an OLED device was fabricated in the same manner as in Device Example 2, by using compound CBP as the host and compound D-50 as a dopant to deposit a 40 nm thick light-emitting layer on the second hole transport layer; and by depositing BAlq as a 10 nm thick hole-blocking layer. Next, ETL-1 and EIL-1 were evaporated and deposited at a rate of 4:6 to form a 25 nm thick electron transport layer on the hole-blocking layer.

[0106] The results show that an efficiency of 43.2 cd / A and 1000 nits of green light emission can be confirmed at a driving voltage of 5.5 V.

[0107] The compounds used for the device examples and comparative examples are shown in Table 2 below.

[0108] Table 2

Claims

1. An organic electroluminescent device comprising an organic electroluminescent compound represented by Formula 1 in an electron transport layer: ---(1) in, At least one of R1, R2 and R3 is represented by the following equation 2; ---(2) in, L represents a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene, wherein the substituent of the substituted phenylene, the substituted naphthylene, or the substituted biphenylene represents at least one selected from the group consisting of: deuterium, halogen, and cyano. Ar represents a substituted or unsubstituted triazine group, wherein the substituent of the substituted triazine group represents at least one selected from the group consisting of: deuterium, cyano, and (3- to 30-membered) heteroaryl substituted or unsubstituted (C6-C30) aryl. R1 to R3 are each independently represented by Equation 2, or represent hydrogen or deuterium; p to r represent integers from 1 to 4; s and t each independently represent integers from 1 to 3; and When p to t is 2 or greater, each R1, each R2, each R3, each L, or each Ar can be the same or different.

2. The organic electroluminescent device according to claim 1, wherein, Equation 1 is represented by any one of the following equations 1-1 to 1-3: ---(1-1) ---(1-2) ---(1-3) in, L, Ar, R1 to R3 and p to t are as defined in claim 1.

3. The organic electroluminescent device according to claim 1, wherein, The compound represented by Formula 1 is selected from the group consisting of: 。

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