Polycyclic aromatic derivative compounds and organic electroluminescent devices using the same

Abstract

The present invention relates to polycyclic aromatic derivative compounds and organic electroluminescent devices comprising the same. The present invention can realize high-efficiency and long-life organic electroluminescent devices having significantly improved luminous efficiency, and thus can be effectively used for industrial applications including flat panel display devices, flexible display devices, monochrome or white flat lighting devices, and monochrome or white flexible lighting devices.

Description

Technical Field

[0001] This invention relates to polycyclic aromatic derivatives and efficient and durable organic electroluminescent devices using said polycyclic aromatic derivatives with significantly improved luminescence efficiency. Background Technology

[0002] Organic electroluminescent devices are self-emissive devices in which electrons injected from an electron injection electrode (cathode) recombine with holes injected from a hole injection electrode (anode) in the emissive layer to form excitons, which emit light while releasing energy. Such organic electroluminescent devices have advantages such as low driving voltage, high brightness, wide viewing angle, and short response time, and can be applied to full-color light-emitting flat panel displays. Due to these advantages, organic electroluminescent devices have attracted attention as a next-generation light source.

[0003] The above-mentioned characteristics of organic electroluminescent devices are achieved through structural optimization of the organic layer of the device, and are supported by stable and effective materials used for the organic layer (e.g., hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, and electron blocking materials). However, further research is still needed to develop structurally optimized organic layers for organic electroluminescent devices and stable and effective materials for the organic layers of organic electroluminescent devices.

[0004] Therefore, there is a continuous need to develop structures for organic electroluminescent devices that are optimized to improve their luminescence properties, as well as new materials that can support the optimized structures of organic electroluminescent devices. Summary of the Invention

[0005] Technical issues

[0006] Therefore, the present invention aims to provide an organic layer for an organic electroluminescent device to achieve high efficiency and long lifetime of the device using polycyclic aromatic derivatives. The present invention also aims to provide an organic electroluminescent device comprising said polycyclic aromatic derivatives.

[0007] Technical solution

[0008] One aspect of the present invention provides a polycyclic aromatic derivative represented by formula A:

[0009] [Formula A]

[0010]

[0011] The structure of Formula A, specific compounds that can be represented by Formula A, and the limitations of rings Q1 to Q3, X, Y1, and Y2 are described below.

[0012] The present invention also provides an organic electroluminescent device comprising a first electrode, a second electrode opposite to the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein one of the organic layers comprises at least one of a specific polycyclic aromatic compound that can be represented by formula A.

[0013] Beneficial effects

[0014] The polycyclic aromatic derivatives of the present invention can be used in the organic layer of organic electroluminescent devices to achieve high efficiency and long lifespan of the devices. Detailed Implementation

[0015] The invention will now be described in more detail.

[0016] This invention relates to polycyclic aromatic derivatives represented by formula A for use in organic electroluminescent devices:

[0017] [Formula A]

[0018]

[0019] Q1 is selected from substituted or unsubstituted C6-C. 50 Monocyclic or polycyclic aromatic hydrocarbon rings, substituted or unsubstituted C2-C 50 Monocyclic or polycyclic aromatic heterocycles, substituted or unsubstituted C6-C 50 Monocyclic or polycyclic aliphatic hydrocarbon rings, and substituted or unsubstituted C2-C 50 Monocyclic or polycyclic aliphatic heterocycles, where Q2 and Q3 may be the same or different from each other, and each is independently selected from substituted or unsubstituted C6-C. 50 Monocyclic or polycyclic aromatic hydrocarbon rings and substituted or unsubstituted C2-C 50 Monocyclic or polycyclic aromatic heterocycles, where X is selected from B, P, P=O, P=S, and Al, and Y1 and Y2 are identical or different from each other, and each is independently a single bond or selected from [the group consisting of different elements]. -O-, -S-, and -Se-, and R1 through R5 may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C1-C 30 Alkenyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C2-C 30 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 heteroaryl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C5-C 30 The arylthio group, substituted or unsubstituted amino group, substituted or unsubstituted silyl group, nitro group, cyano group, and halogen are provided that each of R1 to R5 is optionally bonded to at least one of rings Q1 to Q3 to form an alicyclic or aromatic monocyclic or polycyclic ring, R2 and R3 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, and R4 and R5 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring.

[0020] The use of the aforementioned polycyclic aromatic derivatives makes the organic electroluminescent device efficient and durable.

[0021] The specific structure of Formula A and the modified structure of Formula A with additional rings contained within the substituents can be found in the specific compounds illustrated below.

[0022] As used herein, the term "substituted" in the definitions of rings Q1 to Q3 and R1 to R5 means substituted with one or more substituents selected from: deuterium, cyano, halogen, hydroxyl, nitro, alkyl, haloalkyl, cycloalkyl, alkenyl, ynyl, heteroalkyl, aryl, arylalkyl, alkylaryl, heteroaryl, heteroarylalkyl, alkoxy, amino, silyl, aryloxy, and a mixture of aliphatic-aromatic cyclic groups, or combinations thereof. As used herein, the term "unsubstituted" in the same definitions means without substituents.

[0023] In "substituted or unsubstituted C1-C" 30 Alkyl group, substituted or unsubstituted C6-C 50 In the aryl group, the number of carbon atoms in the alkyl or aryl group indicates the number of carbon atoms constituting the unsubstituted alkyl or aryl moiety, regardless of the number of carbon atoms in the substituents. For example, a phenyl group substituted with butyl at the para position corresponds to a C6 aryl group substituted with C4 butyl.

[0024] As used herein, the expression "forming a ring with an adjacent substituent" means that the corresponding substituent combines with an adjacent substituent to form a substituted or unsubstituted alicyclic or aromatic ring, and the term "adjacent substituent" can mean a substituent on an atom directly bonded to the atom substituted with the corresponding substituent, a substituent located spatially closest to the corresponding substituent, or another substituent on the atom substituted with the corresponding substituent. For example, two substituents substituted at the ortho position on a benzene ring or two substituents on the same carbon atom in an alicyclic ring can be considered "adjacent" to each other.

[0025] The alkyl group can be straight-chain or branched, and specific examples include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0026] The alkenyl group is intended to include straight-chain alkenyl and branched alkenyl groups, and may optionally be substituted with one or more additional substituents. The alkenyl group may specifically be vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, or styryl, but is not limited thereto.

[0027] The alkynyl group is intended to include straight-chain alkynyl and branched-chain alkynyl, and may optionally be substituted with one or more additional substituents. The alkynyl group may be, for example, ethynyl or 2-propynyl, but is not limited thereto.

[0028] Cycloalkyl is intended to include both monocyclic and polycyclic cycloalkyl groups, and may optionally be substituted with one or more additional substituents. As used herein, the term "polycyclic" means that the cycloalkyl group may be directly attached to or fused with one or more additional cyclic groups. The additional cyclic groups may be cycloalkyl, and other examples include heterocyclic, aryl, and heteroaryl groups. Cycloalkyl groups may specifically be, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, adamantyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, or cyclooctyl.

[0029] Heterocyclic alkyl groups are intended to include monocyclic and polycyclic heterocyclic alkyl groups interrupted by heteroatoms such as O, S, Se, N, or Si, and may optionally be substituted with one or more additional substituents. As used herein, the term "polycyclic" means that a heterocyclic alkyl group may be directly attached to or fused with one or more additional cyclic groups. The additional cyclic groups may be heterocyclic alkyl groups, and other examples include cycloalkyl, aryl, and heteroaryl groups.

[0030] Aromatic hydrocarbon rings or aryl groups can be monocyclic or polycyclic. Examples of monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, and styrene. Examples of polycyclic aryl groups include naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, and tetraphenyl. The compounds used include methyl, fluorenyl, acenaphathcenyl, triphenylene, and fluoranyl, but the scope of the invention is not limited thereto.

[0031] Aromatic heterocycles or heteroaryl groups refer to aromatic rings interrupted by one or more heteroatoms. Examples of aromatic heterocycles or heteroaryl groups include, but are not limited to, thiophene, furanyl, pyrrole, imidazolyl, and thiazolyl. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Triazolyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Pyrazenopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, dibenzofuranyl, phenanthrolinel, thiazolyl, iso azole group, Diazolyl, thiadiazolyl, benzothiazolyl, and phenthiazinyl.

[0032] Aliphatic hydrocarbon rings are non-aromatic rings consisting only of carbon and hydrogen atoms. Aliphatic hydrocarbon rings are intended to include monocyclic and polycyclic aliphatic hydrocarbon rings and may optionally be substituted with one or more additional substituents. As used herein, the term "polycyclic" means that the aliphatic hydrocarbon ring can be directly attached to or fused with one or more additional cyclic groups. These additional cyclic groups can be aliphatic hydrocarbon rings, and other examples include aliphatic heterocyclic groups, aryl groups, and heteroaryl groups. Specific examples of aliphatic hydrocarbon rings include, but are not limited to, cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, adamantyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl; cycloalkanes such as cyclohexane and cyclopentane; and cycloalkenes such as cyclohexene and cyclopentene.

[0033] Aliphatic heterocycles are aliphatic rings interrupted by one or more heteroatoms such as O, S, Se, N, and Si. Aliphatic heterocycles are intended to include monocyclic or polycyclic aliphatic heterocycles and may optionally be substituted with one or more additional substituents. As used herein, the term "polycyclic" means that an aliphatic heterocycle, such as a heterocyclic alkyl, heterocyclic alkane, or heterocyclic alkene, can be directly attached to or fused with one or more additional cyclic groups. These additional cyclic groups can be aliphatic heterocycles, and other examples include aliphatic hydrocarbon rings, aryl groups, and heteroaryl groups.

[0034] A mixed aliphatic-aromatic ring is a ring in which at least one aliphatic ring and at least one aromatic ring are connected or fused together and the ring as a whole is non-aromatic. A mixed aliphatic-aromatic polycyclic ring may contain one or more heteroatoms selected from N, O, P and S, other than carbon (C).

[0035] Alkoxy groups can be specifically methoxy, ethoxy, propoxy, isobutoxy, sec-butoxy, pentoxy, isopentoxy, or hexoxy, but are not limited thereto.

[0036] The silyl group can be, for example, -SiH3, alkylsilyl, arylsilyl, alkylarylsilyl, and arylheteroarylsilyl. Specific examples of silyl groups include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, and dimethylfuranylsilyl.

[0037] The amino group can be, for example, -NH2, alkylamino, arylamino, and arylheteroarylamino. An arylamino is an aryl-substituted amino group, an alkylamino is an alkyl-substituted amino group, and an arylheteroarylamino is an amino group substituted with both aryl and heteroaryl groups. Examples of arylamino groups include substituted or unsubstituted monoarylamino groups, substituted or unsubstituted diarylamino groups, and substituted or unsubstituted triarylamino groups. The aryl and heteroaryl moieties in arylamino and arylheteroarylamino groups can be monocyclic or polycyclic aryl and heteroaryl. An arylamino group can contain two or more aryl moieties, and an arylheteroarylamino group can contain two or more heteroaryl moieties. In this case, the aryl moieties can be monocyclic or polycyclic aryl moieties, or can be composed of both monocyclic and polycyclic aryl moieties. The heteroaryl moieties can be monocyclic or polycyclic heteroaryl moieties, or can be composed of both monocyclic and polycyclic heteroaryl moieties. The aryl and heteroaryl moieties in arylamine and arylheteroarylamine groups can be selected from those exemplified above.

[0038] The aryl moiety in aryloxy and arylthio groups is the same as that described above for aryl groups. Specific examples of aryloxy groups include, but are not limited to, phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethylphenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenoxy, 4-biphenoxy, 1-naphthoxy, 2-naphthoxy, 4-methyl-1-naphthoxy, 5-methyl-2-naphthoxy, 1-anthraoxy, 2-anthraoxy, 9-anthraoxy, 1-phenanthoxy, 3-phenanthoxy, and 9-phenanthoxy. The arylthio group can be, for example, phenylthio, 2-methylphenylthio, or 4-tert-butylphenylthio, but is not limited thereto.

[0039] The halogen group can be, for example, fluorine, chlorine, bromine or iodine.

[0040] More specifically, the polycyclic aromatic derivatives represented by formula A according to the present invention may be selected from, but are not limited to, the following compounds 1 to 72:

[0041]

[0042]

[0043]

[0044]

[0045]

[0046] The specific substituents in Formula A can be clearly seen from the structures of compounds 1 to 72, but are not intended to limit the range of compounds represented by Formula A.

[0047] As can be seen from the specific compounds above, the polycyclic aromatic derivatives of the present invention contain B, P, P=O, P=S, or Al, and have a polycyclic aromatic structure. Introducing substituents into the polycyclic aromatic structure enables the synthesis of organic materials possessing the inherent properties of the substituents. For example, the substituents are designed for use in materials for hole injection layers, hole transport layers, light-emitting layers, electron transport layers, electron injection layers, electron blocking layers, and hole blocking layers in organic electroluminescent devices. This introduction satisfies the requirements for materials used in organic layers, resulting in highly efficient organic electroluminescent devices.

[0048] Another aspect of the present invention relates to an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers between the first electrode and the second electrode, wherein one of the organic layers comprises at least one of an organic electroluminescent compound that can be represented by formula A.

[0049] That is, according to one embodiment of the present invention, the organic electroluminescent device has a structure in which one or more organic layers are disposed between a first electrode and a second electrode. The organic electroluminescent device of the present invention can be manufactured by suitable methods known in the art using suitable materials known in the art, except that an organic electroluminescent compound of formula A is used to form the corresponding organic layers.

[0050] The organic layer of the organic electroluminescent device according to the present invention can be formed into a single-layer structure. Alternatively, the organic layer can have a multi-layer stacked structure. For example, the organic layer can have a structure including a hole injection layer, a hole transport layer, a hole blocking layer, a light-emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer, but is not limited to this structure. The number of organic layers is not limited and can be increased or decreased. The preferred structure of the organic layer of the organic electroluminescent device according to the present invention will be described in more detail in the following embodiment section.

[0051] The organic electroluminescent device of the present invention includes an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode. The organic electroluminescent device of the present invention may optionally include a hole injection layer between the anode and the hole transport layer, and an electron injection layer between the electron transport layer and the cathode. If necessary, the organic electroluminescent device of the present invention may also include one or two intermediate layers, such as a hole blocking layer or an electron blocking layer.

[0052] According to a preferred embodiment of the present invention, one of the organic layers between the first electrode and the second electrode may be a light-emitting layer composed of a host and a compound represented by formula A as a dopant.

[0053] Based on approximately 100 parts by weight of the substrate, the dopant content in the light-emitting layer is typically in the range of approximately 0.01 parts by weight to approximately 20 parts by weight, but is not limited to this range.

[0054] According to a preferred embodiment of the present invention, the main component may be an anthracene derivative represented by formula C:

[0055] [Formula C]

[0056]

[0057] Among them, R 21 To R 28 Whether they are the same or different from each other, and as defined by any of R1 to R5 in [Equation A], Ar9 and Ar 10 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C2-C 30Alkenyl, substituted or unsubstituted C2-C 20 Alkyne group, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted C2-C 50 heteroaryl, substituted or unsubstituted C2-C 30 Heterocyclic alkyl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C6-C 30 Arylthio, halogen, substituted or unsubstituted amino groups and substituted or unsubstituted silyl groups, L 13 It is a single bond or selected from substituted or unsubstituted C6-C. 20 aryl and substituted or unsubstituted C2-C 20 The heteroaryl group, and k is an integer from 1 to 3, provided that when k is 2 or greater, the linking group L... 13 They are the same or different from each other.

[0058] According to one embodiment of the present invention, Ar9 in formula C may be a substituted or unsubstituted phenyl or a substituted or unsubstituted naphthyl group.

[0059] According to one embodiment of the present invention, the subject represented by formula C may be selected from, but is not limited to, compounds of formulas C1 to C69:

[0060]

[0061]

[0062]

[0063]

[0064] The specific structure of the organic electroluminescent device according to the present invention, the method for manufacturing the device, and the materials used for the organic layer will be described below.

[0065] First, an anode material is coated onto a substrate to form the anode. The substrate can be any substrate used in general organic electroluminescent devices. Preferably, the substrate is an organic substrate or a transparent plastic substrate that excels in transparency, surface smoothness, ease of handling, and water resistance. Highly transparent and conductive metal oxides such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO) are used as the anode material.

[0066] Hole injection material is coated onto the anode by vacuum thermal evaporation or spin coating to form a hole injection layer. Then, hole transport material is coated onto the hole injection layer by vacuum thermal evaporation or spin coating to form a hole transport layer.

[0067] There are no specific limitations on the hole injection material, as long as it is commonly used in the art. Specific examples of such materials include 4,4',4”-tris(2-naphthylphenyl-phenylamino)triphenylamine (2-TNATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-bis(4-(phenyl-m-tolylamino)phenyl]biphenyl-4,4'-diamine (DNTPD), and 1,4,5,8,9,11-hexaazabenzophenanthrenehexanitrile (HAT-CN).

[0068] There are no specific limitations on the hole transport material, as long as it is commonly used in the art. Examples of such materials include N,N'-bis(3-methylphenyl)-N,N'-diphenyl-(1,1-biphenyl)-4,4'-diamine (TPD) and N,N'-bis(naphthyl-1-yl)-N,N'-diphenylbenzidine (α-NPD).

[0069] Subsequently, a hole-assist layer and a light-emitting layer are sequentially formed on the hole transport layer. A hole-blocking layer can optionally be formed on the light-emitting layer by vacuum thermal evaporation or spin coating. The hole-blocking layer is formed as a thin film. The hole-blocking layer functions to prevent holes from passing through the organic light-emitting layer into the cathode. This function prevents degradation of the device's lifetime and efficiency. For this purpose, materials with very low highest occupied molecular orbital (HOMO) energy levels are used for the hole-blocking layer. There are no particular limitations on the hole-blocking material, as long as it can transport electrons and has a higher ionization potential than the light-emitting compound. Representative examples of suitable hole-blocking materials include BAlq, BCP, and TPBI.

[0070] Examples of materials used for hole blocking layers include, but are not limited to, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq2, OXD-7, and Liq.

[0071] An electron transport layer is deposited on a hole-blocking layer by vacuum thermal evaporation or spin coating, and an electron injection layer is formed on the electron transport layer. A cathode metal is then deposited on the electron injection layer by vacuum thermal evaporation to form a cathode, thus completing the fabrication of the organic electroluminescent device.

[0072] For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) can be used as the metal for forming the cathode. The organic electroluminescent device can be a top-emitting type. In this case, a transmissive material such as ITO or IZO can be used to form the cathode.

[0073] The material used in the electron transport layer serves to stably transport electrons injected from the cathode. The electron transport material can be any material known in the art, and examples include, but are not limited to, quinoline derivatives, particularly tris(8-hydroxyquinoline)aluminum (Alq3), TAZ, Balq, bis(benzoquinoline-10-hydroxy)beryllium (Bebq2); and Diazole derivatives, such as PBD, BMD and BND.

[0074] Each of the organic layers can be formed by single-molecule deposition or solution deposition. According to single-molecule deposition, the material for each layer is vapor-deposited into a thin film under heat and vacuum or reduced pressure. According to solution deposition, the material for each layer is mixed with a suitable solvent, and then the mixture is formed into a thin film by a suitable method such as inkjet printing, roll-to-roll coating, screen printing, spraying, dip coating, or spin coating.

[0075] The organic electroluminescent device of the present invention can be used in displays or lighting systems selected from the following: flat panel displays, flexible displays, monochrome flat panel lighting systems, white flat panel lighting systems, flexible monochrome lighting systems, and flexible white lighting systems.

[0076] Invention Embodiments

[0077] The invention will be explained and illustrated in more detail with reference to the following embodiments. However, it will be apparent to those skilled in the art that these embodiments are by no means intended to limit the scope of the invention.

[0078] Synthesis Example 1. Preparation of Compound 64

[0079] Synthesis Example 1-1. Synthesis of Intermediate A-1

[0080]

[0081] Reference (Tetrahedron Letters, 2011, Vol. 52, #11, pp. 1161-1164) describes the synthesis of A-1c using A-1a and A-1b. Reference (Dyes and Pigments, 2016, Vol. 133, pp. 114-119) describes the synthesis of A-1 (37.3 g, 83.2%) from A-1c.

[0082] Chemical formula: C 18 H18 The calculated MS (ESI) value of BrClN(Pos) is 362.03, and the measured value is 362.0. Synthesis Example 1-2. Synthesis of intermediate A-2

[0083]

[0084] A-2a was synthesized with reference to US Patent Publication No. 2020 / 172558A1. A-2 (15.3 g, yield 91.1%) was synthesized from A-1 and A-2a with reference to document (Korean Patent Publication No. 2017 / 52777A).

[0085] Chemical formula: C 38 H 43 The MS (ESI) calculated value of Cl2N2(Pos) is 597.28, and the measured value is 597.2.

[0086] Synthesis Example 1-3. Synthesis of Intermediate A-3

[0087]

[0088] A-2 (21.7 g), A-3a (6.65 g), bis(tri-tert-butylphosphine)palladium(0) (0.56 g), sodium tert-butoxide (10.5 g), and xylene (200 mL) were placed in a reactor. The mixture was stirred under reflux for 24 hours. The reaction mixture was cooled to room temperature and water (200 mL) was added. The organic layer was extracted with ethyl acetate, concentrated under reduced pressure, and purified by silica gel column chromatography to give A-3 (6.0 g, 23.3% yield).

[0089] Chemical formula: C 50 H 50 The calculated MS (ESI) value for N3O(Pos) is 708.40, and the measured value is 708.4.

[0090] Synthesis Examples 1-4. Synthesis of Compound 64

[0091]

[0092] A-3 (13.6 g) and dichlorobenzene (140 mL) were placed in a reactor, and boron tribromide (1.8 mL) was added dropwise at room temperature. The mixture was stirred under reflux for 16 hours. The reaction mixture was cooled to room temperature and water (60 mL) and sodium acetate (4.7 g) were added. The organic layer was extracted with ethyl acetate, concentrated under reduced pressure, purified by silica gel column chromatography, and subsequently recrystallized to give compound 64 (1.40 g, 10.2% yield).

[0093] Chemical formula: C 50 H47 The calculated MS (ESI) value for BN3O(Pos) is 716.38, and the measured value is 716.3.

[0094] Synthesis Example 2. Synthesis of Compound 65

[0095] Synthesis Example 2-1. Synthesis of Intermediate B-1

[0096]

[0097] Intermediate B-1c was synthesized from intermediate B-1a in the same manner as in Synthesis Example 1, and intermediate B-1 (88.1%) was synthesized from intermediate B-1c.

[0098] Chemical formula: C 46 H 43 The MS (ESI) calculated value of Cl2N2(Pos) is 693.28, and the measured value is 693.2.

[0099] Synthesis Example 2-2. Synthesis of Compound 65

[0100]

[0101] Intermediate B-2c was synthesized from intermediate B-2a in the same manner as in Synthesis Example 1, and compound 65 (9.4%) was synthesized from intermediate B-2c.

[0102] Chemical formula: C 62 H 57 The calculated MS (ESI) value for BN3(Pos) is 854.47, and the measured value is 854.4.

[0103] Synthesis Example 3. Synthesis of Compound 66

[0104] Synthesis Example 3-1. Synthesis of Intermediate C-1

[0105]

[0106] Intermediate C-1c was synthesized from intermediate C-1a in the same manner as in Synthesis Example 1, and intermediate C-1 (90.1%) was synthesized from intermediate C-1c.

[0107] Chemical formula: C 56 H 56 The MS (ESI) calculated value of Cl2N3(Pos) was 840.39, and the measured value was 840.3.

[0108] Synthesis Example 3-2. Synthesis of Compound 66

[0109]

[0110] Intermediate C-2c was synthesized from intermediate C-2a in the same manner as in Synthesis Example 1, and compound 66 (14.1%) was synthesized from intermediate C-2c.

[0111] Chemical formula: C 68 H 62 The calculated MS (ESI) value for BN4(Pos) is 945.51, and the measured value is 945.5.

[0112] Synthesis Example 4. Synthesis of Compound 67

[0113] Synthesis Example 4-1. Synthesis of Intermediate D-1

[0114]

[0115] Intermediate D-1c was synthesized from intermediate D-1a in the same manner as in Synthesis Example 1, and intermediate D-1 (81.2%) was synthesized from intermediate D-1c.

[0116] Chemical formula: C 54 H 42 The MS (ESI) calculated value of Cl2N3O,(Pos) was 834.25, and the measured value was 834.2. Synthesis Example 4-2. Synthesis of compound 67

[0117]

[0118] Intermediate D-2c was synthesized from intermediate D-2a in the same manner as in Synthesis Example 1, and compound 67 (9.3%) was synthesized from intermediate D-2c.

[0119] Chemical formula: C 64 H 52 The calculated MS (ESI) value for BN4S (Pos) is 919.40, and the measured value is 919.4.

[0120] Synthesis Example 5. Synthesis of Compound 68

[0121] Synthesis Example 5-1. Synthesis of Intermediate E-1

[0122]

[0123] Intermediate E-1c was synthesized from intermediate E-1a in the same manner as in Synthesis Example 1, and intermediate E-1 (76.5%) was synthesized from intermediate E-1c.

[0124] Chemical formula: C 44 H 47 The MS (ESI) calculated value of Cl2N2(Pos) is 673.31, and the measured value is 673.3.

[0125] Synthesis Example 5-2. Synthesis of Compound 68

[0126]

[0127] Intermediate E-2c was synthesized from intermediate E-2a in the same manner as in Synthesis Example 1, and compound 68 (8.9%) was synthesized from intermediate E-2c.

[0128] Chemical formula: C 60 H 61 The calculated MS (ESI) value for BN3(Pos) is 834.50, and the measured value is 834.5.

[0129] Synthesis Example 6. Synthesis of Compound 69

[0130] Synthesis Example 6-1. Synthesis of Intermediate F-1

[0131]

[0132] Intermediate F-1c was synthesized from intermediate F-1a in the same manner as in Synthesis Example 1, and intermediate F-1 (72.4%) was synthesized from intermediate F-1c.

[0133] Chemical formula: C 54 H 56 The MS (ESI) calculated value of Cl2N3(Pos) is 816.39, and the measured value is 816.3.

[0134] Synthesis Example 6-2. Synthesis of Compound 69

[0135]

[0136] Intermediate F-2c was synthesized from intermediate F-2a in the same manner as in Synthesis Example 1, and compound 69 (8.5%) was synthesized from intermediate F-2c.

[0137] Chemical formula: C 72 H 66 The calculated MS (ESI) value for BN4(Pos) is 997.54, and the measured value is 997.5.

[0138] Examples 1 to 10: Fabrication of Organic Electroluminescent Devices

[0139] The ITO glass was patterned to have a 2mm × 2mm luminescent area, followed by cleaning. After the cleaned ITO glass was installed in the vacuum chamber, the base pressure was adjusted to 1 × 10⁻⁶. -7 To. DNTPD and compounds represented by formula H The compounds were deposited on ITO in this order. A mixture of the main component, represented by BH1, and the compounds of the present invention shown in Table 1 (3% by weight) was used to form... A thick luminescent layer. Subsequently, a mixture of the compound represented by formula E-1 and the compound represented by formula E-2, in a 1:1 ratio, is formed on the luminescent layer. A thick electron transport layer. A compound represented by formula E-1 is used to form the electron transport layer. A thick electron-injected layer. Al is used to form the electron-injected layer. A thick Al electrode was used to fabricate the organic electroluminescent device. The luminescence characteristics of the organic electroluminescent device were measured at 0.4 mA.

[0140]

[0141]

[0142] Comparative Example 1

[0143] The organic electroluminescent device was manufactured in the same manner as in Example 1, except that BD1 was used instead of the compound of the present invention. The luminescence characteristics of the organic electroluminescent device were measured at 0.4 mA.

[0144] [BD1]

[0145]

[0146] The external quantum efficiency and lifetime of the organic electroluminescent devices of Examples 1 to 10 and Comparative Example 1 were measured. The results are shown in Table 1.

[0147] [Table 1]

[0148]

[0149] As can be seen from the results in Table 1, the organic electroluminescent devices of Examples 1 to 10, which use the compounds of the present invention, exhibit higher luminous efficiency and longer lifetime than the organic electroluminescent device of Comparative Example 1.

[0150] Industrial applicability

[0151] The polycyclic aromatic derivatives of the present invention can be used to manufacture highly efficient and durable organic electroluminescent devices with significantly improved luminous efficiency. Therefore, the polycyclic aromatic derivatives of the present invention can find useful industrial applications in various displays (including flat panel displays and flexible displays) and lighting systems (including monochrome flat panel lighting systems, white flat panel lighting systems, flexible monochrome lighting systems, and flexible white lighting systems).

Claims

1. An organic compound represented by formula A: [Formula A] Q1 is selected from substituted or unsubstituted C6-C. 50 Monocyclic or polycyclic aromatic hydrocarbon rings, substituted or unsubstituted C2-C 50 Monocyclic or polycyclic aromatic heterocycles, substituted or unsubstituted C6-C 50 Monocyclic or polycyclic aliphatic hydrocarbon rings, and substituted or unsubstituted C2-C 50 Monocyclic or polycyclic aliphatic heterocycles, where Q2 and Q3 may be the same or different from each other, and each is independently selected from substituted or unsubstituted C6-C. 50 Monocyclic or polycyclic aromatic hydrocarbon rings and substituted or unsubstituted C2-C 50 Monocyclic or polycyclic aromatic heterocycles, where X is B, and Y1 and Y2 are identical or different and independently constitute [missing information]. R1 is selected from hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C1-C 30 Alkenyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C2-C 30 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 heteroaryl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C5-C 30 The R1 group may be an arylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a nitro group, a cyano group, or a halogen, provided that R1 is optionally bonded to at least one of rings Q1 to Q3 to form an alicyclic or aromatic monocyclic or polycyclic ring.

2. The organic compound according to claim 1, wherein the organic compound is selected from the following compounds: 。 3. An organic electroluminescent device, comprising a first electrode, a second electrode, and one or more organic layers between the first electrode and the second electrode, wherein one of the organic layers comprises an organic compound represented by formula A according to claim 1.

4. The organic electroluminescent device according to claim 3, wherein the organic layer comprises an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer and / or a light-emitting layer, wherein at least one of them comprises the organic compound represented by formula A.

5. The organic electroluminescent device according to claim 4, wherein the light-emitting layer is composed of a host and the compound represented by formula A as a dopant.

6. The organic electroluminescent device according to claim 5, wherein the main body is an anthracene derivative represented by formula C: [Formula C] Where R 21 To R 28 They are the same or different from each other, and as defined by R1 in [Equation A], Ar9 and Ar 10 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C2-C 30 Alkenyl, substituted or unsubstituted C2-C 20 Alkyne group, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted C2-C 50 heteroaryl, substituted or unsubstituted C2-C 30 Heterocyclic alkyl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C6-C 30 Arylthio, halogen, substituted or unsubstituted amino groups and substituted or unsubstituted silyl groups, L 13 It is a single bond or selected from substituted or unsubstituted C6-C. 20 aryl and substituted or unsubstituted C2-C 20 The heteroaryl group, and k is an integer from 1 to 3, provided that when k is 2 or greater, the linking group L... 13 They are the same or different from each other.

7. The organic electroluminescent device according to claim 6, wherein Ar9 in formula C is a substituted or unsubstituted phenyl or a substituted or unsubstituted naphthyl group.

8. The organic electroluminescent device according to claim 6, wherein the anthracene derivative represented by formula C is selected from compounds of formulas C1 to C69: 。 9. The organic electroluminescent device according to claim 4, wherein one or more of the layers are formed by deposition or solution processing.

10. The organic electroluminescent device according to claim 3, wherein the organic electroluminescent device is used for a display or lighting system, the display or the lighting system being selected from flat panel displays, flexible displays, monochrome flat panel lighting systems, white flat panel lighting systems, flexible monochrome lighting systems and flexible white lighting systems.

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