Polycyclic aromatic derivative compounds and organic light emitting device using the same

Abstract

The polycyclic aromatic derivative compound according to the present application is used for an organic layer in a device, and thus can achieve an organic light emitting device of high efficiency, and thus can be used in industry and effectively for various display devices such as flexible displays and lighting devices, such as monochrome flat lighting or white flat lighting and monochrome flexible lighting or white flexible lighting.

Description

TECHNICAL FIELD

[0001] The present application relates to polycyclic aromatic derivatives and high-efficiency organic electroluminescent devices having significantly improved luminous efficiency using the same. BACKGROUND

[0002] An organic electroluminescent device is a self-light-emitting device in which an electron injected from an electron injection electrode (cathode) and a hole injected from a hole injection electrode (anode) recombine in a light-emitting layer to form an exciton, and the exciton emits light while releasing energy. Such an organic electroluminescent device has advantages of low driving voltage, high brightness, large viewing angle, and short response time, and can be applied to a full-color light-emitting flat panel display. Due to these advantages, the organic electroluminescent device is attracting attention as a next-generation light source.

[0003] The above characteristics of the organic electroluminescent device are achieved by optimization of the structure of the organic layer of the device, and are supported by stable and efficient materials for the organic layer, such as a hole injection material, a hole transport material, a light-emitting material, an electron transport material, an electron injection material, and an electron blocking material. However, further research is still needed to develop a structurally optimized organic layer for an organic electroluminescent device and a stable and efficient material for the organic layer of the organic electroluminescent device.

[0004] Therefore, there is a continuous need to develop a structure of an organic electroluminescent device optimized to improve its light-emitting characteristics, and a new material capable of supporting the optimized structure of the organic electroluminescent device. SUMMARY

[0005] TECHNICAL PROBLEM

[0006] Therefore, the present application aims to provide an organic electroluminescent compound for use in an organic layer of an organic electroluminescent device to achieve high efficiency of the device. The present application also aims to provide an organic electroluminescent device comprising the same.

[0007] TECHNICAL SOLUTION

[0008] One aspect of the present application provides a compound represented by Formula A:

[0009] [Formula A]

[0010]

[0011] More specific structures of Formula A, the limitations of Q1 to Q5, X, and Y in Formula A, and specific polycyclic aromatic compounds that can be represented by Formula A are described below.

[0012] Another aspect of the present application provides an organic electroluminescent device including a first electrode, a second electrode opposite to the first electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein one of the organic layers comprises at least one of specific polycyclic aromatic compounds which can be represented by Formula A.

[0013] Advantages

[0014] The polycyclic aromatic derivatives of the present application can be used in the organic layer of an organic electroluminescent device to achieve high efficiency of the device. DETAILED DESCRIPTION

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

[0016] The present application relates to polycyclic aromatic derivatives for use in an organic electroluminescent device represented by Formula A:

[0017] [Formula A]

[0018]

[0019] wherein Q1to Q5are the same as or different from each other and each is independently a substituted or unsubstituted C6-C 50 aromatic hydrocarbon ring, or a substituted or unsubstituted C2-C 50 aromatic heterocycle, each X is independently selected from B, P, P=O and P=S, each Y is independently selected from N-R1, CR2R3, O, S, Se and SiR4R5, and R1to R5are the same as or different from each other and each is independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C 30 alkyl, a substituted or unsubstituted C6-C 50 aryl, a substituted or unsubstituted C3-C 30 cycloalkyl, a substituted or unsubstituted C2-C 50 heteroaryl, a substituted or unsubstituted C1-C 30 alkoxy, a substituted or unsubstituted C6-C 30 aryloxy, a substituted or unsubstituted C1-C 30 alkylthio, a substituted or unsubstituted C5-C 30 arylthio, a substituted or unsubstituted C1-C 30 alkylamino, a substituted or unsubstituted C5-C 30 arylamino, a substituted or unsubstituted C1-C 30 alkylsilyl, a substituted or unsubstituted C5-C 30aryl, substituted or unsubstituted C1-C20alkyl, substituted or unsubstituted C5-C20cycloalkyl, substituted or unsubstituted C2-C20alkenyl, substituted or unsubstituted C6-C20aryl, substituted or unsubstituted C1-C20alkoxy, substituted or unsubstituted C6-C20aryloxy, substituted or unsubstituted C1-C20alkylthio, substituted or unsubstituted C6-C20arythio, substituted or unsubstituted C1-C20alkylamino, substituted or unsubstituted C6-C20arylamino, substituted or unsubstituted C1-C20alkylsilyl, nitro, cyano, and halogen, with the proviso that each of R1to R5is optionally bonded to one of rings Q1and Q5to form an alicyclic or aromatic mono- or polycyclic ring, R2and R3are optionally connected to each other to form an alicyclic or aromatic mono- or polycyclic ring, and R4and R5are optionally connected to each other to form an alicyclic or aromatic mono- or polycyclic ring.

[0020] According to one embodiment of the present application, X in Formula A can be boron (B). The presence of boron (B) in the structure of the polycyclic aromatic derivative ensures high efficiency and long lifetime of the organic electroluminescent device.

[0021] The use of the polycyclic aromatic derivative makes the organic electroluminescent device highly efficient and durable.

[0022] The polycyclic aromatic derivative represented by Formula A according to the present application has the following structural features:

[0023] (i) either one or both of Q1and Q5is selected from the structures represented by structural formulas B-1 to B-3:

[0024]

[0025] wherein each Y is independently selected from N-R1, CR2R3, O, S, Se, and SiR4R5, R1to R5are as defined in Formula A, Q6is a substituted or unsubstituted C6-C 50 aromatic hydrocarbon ring or a substituted or unsubstituted C2-C 50 aromatic heterocycle, each R is independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C 30 alkyl, a substituted or unsubstituted C6-C 50 aryl, a substituted or unsubstituted C3-C 30 cycloalkyl, a substituted or unsubstituted C2-C 50 heteroaryl, a substituted or unsubstituted C1-C 30 alkoxy, a substituted or unsubstituted C6-C 30 aryloxy, a substituted or unsubstituted C1-C 30 alkylthio, a substituted or unsubstituted C5-C 30 arythio, a substituted or unsubstituted C1-C 30 alkylamino, a substituted or unsubstituted C5-C 30 arylamino, a substituted or unsubstituted C1-C 30 alkylsilyl, a substituted or unsubstituted C5-C 30aryl silyl groups, nitro groups, cyano groups, and halogen, provided that the groups R are optionally bonded to each other or are each independently optionally bonded to one of the rings Q1and Q5to form an alicyclic or aromatic mono- or polycyclic ring, and each * indicates the position at which the corresponding ring Q1or Q5in formula A is bonded to adjacent X and Y;

[0026] (ii) Q3 is selected from the structures represented by structural formulae B-4 to B-6:

[0027]

[0028] wherein Y and Q6 are as defined above, and each * indicates the position at which the ring Q3 in formula A is bonded to adjacent X and Y; or

[0029] (iii) either one or both of Q1and Q5is / are selected from the structures represented by structural formulae B-1 to B-3, and Q3 is selected from the structures represented by structural formulae B-4 to B-6.

[0030] In accordance with the structural features of the polycyclic aromatic derivatives represented by formula A according to the present application, when Q1or Q5is selected from the structures represented by structural formulae B-1 to B-3, formula A can have one of the following skeletal structures represented by formulae A-1 to A-6:

[0031]

[0032] wherein X, Y, R, and Q2to Q6are as defined in formula A.

[0033] In accordance with the structural features of the polycyclic aromatic derivatives represented by formula A according to the present application, when Q1and Q5are both selected from the structures represented by structural formulae B-1 to B-3, formula A can have one of the following skeletal structures represented by formulae A-7 to A-15:

[0034]

[0035] wherein X, Y, R, Q2, Q3, Q4, and Q6are as defined in formula A.

[0036] In accordance with the structural features of the polycyclic aromatic derivatives represented by formula A according to the present application, when Q3 is selected from the structures represented by structural formulae B-4 to B-6, formula A can have one of the following skeletal structures represented by formulae A-16 to A-21:

[0037]

[0038] wherein X, Y, Q1, Q2, Q4, Q5, and Q6are as defined in formula A.

[0039] According to the structural feature of the polycyclic aromatic derivative represented by Formula A according to the present application, when Q3 is selected from the structure represented by Structural Formula B-4 to B-6 and Q1 or Q5 is selected from the structure represented by Structural Formula B-1 to B-3, Formula A can have one of the following backbone structures represented by Formulas A-22 to A-53:

[0040]

[0041]

[0042] wherein X, Y, Q1, Q2, Q4, Q5, and Q6 are as defined in Formula A.

[0043] According to the structural feature of the polycyclic aromatic derivative represented by Formula A according to the present application, when Q3 is selected from the structure represented by Structural Formula B-4 to B-6 and Q1 and Q5 are both selected from the structure represented by Structural Formula B-1 to B-3, Formula A can have one of the following backbone structures represented by Formulas A-54 to A-79:

[0044]

[0045]

[0046] wherein X, Y, R, Q2, Q4, and Q6 are as defined in Formula A.

[0047] Although not illustrated in Formulas 1 to 79, it is understood that Q1 and Q5 are the same as or different from each other, and each is independently selected from the structure represented by Structural Formula B-1 to B-3.

[0048] The use of various polycyclic aromatic backbone structures, such as the structures represented by Formulas A-1 to A-79, satisfies the desired requirements of achieving high efficiency and long lifespan of the organic electroluminescent device for the plurality of organic layers of the device.

[0049] According to one embodiment of the present application, Q1 to Q6 can be the same as or different from each other, and can each be independently represented by Structural Formula Q-1:

[0050] [Structural Formula Q-1]

[0051]

[0052] wherein each Z is independently CR or N, and each R is independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C 30 alkyl, a substituted or unsubstituted C6-C 50 aryl, a substituted or unsubstituted C3-C 30 cycloalkyl, a substituted or unsubstituted C2-C 50heteroaryl, substituted or unsubstituted C1-C 30 alkoxy, substituted or unsubstituted C6-C 30 aryloxy, substituted or unsubstituted C1-C 30 alkylthio, substituted or unsubstituted C5-C 30 arylthio, substituted or unsubstituted C1-C 30 alkylamino, substituted or unsubstituted C5-C 30 arylamino, substituted or unsubstituted C1-C 30 alkylsilyl, substituted or unsubstituted C5-C 30 arylsilyl, nitro, cyano, and halogen, with the proviso that the groups R are optionally bonded to one another or are each independently optionally connected to an adjacent substituent to form an alicyclic or aromatic monocyclic or polycyclic ring, one or more carbon atoms of which are optionally replaced with a heteroatom selected from N, S, and O, and Z bonded structurally to each of X and Y is C-H, unless otherwise defined.

[0053] As used herein, the term “substituted” in the definitions of Q1to Q3, R, R1to R 13 and R 21 to R 24 in the definitions of R1to R 24 alkyl, C3-C 24 cycloalkyl, C1-C 24 haloalkyl, C1-C 24 alkenyl, C1-C 24 alkynyl, C1-C 24 heteroalkyl, C1-C 24 heterocycloalkyl, C6-C 24 aryl, C6-C 24 arylalkyl, C2-C 24 heteroaryl, C2-C 24 heteroarylalkyl, C1-C 24 alkoxy, C1-C 24 alkylamino, C1-C 24 arylamino, C1-C 24 heteroarylamino, C1-C 24 alkylsilyl, C1-C 24 arylsilyl, and C1-C 24 aryloxy, or combinations thereof. As used herein, the term “unsubstituted” means no substituents.

[0054] In “substituted or unsubstituted C1-C 10Alkyl group, substituted or unsubstituted C6-C 30 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.

[0055] As used herein, the phrase "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, the substituent 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.

[0056] Alkyl groups can be straight-chain or branched. The number of carbon atoms in an alkyl group is not particularly limited, but is preferably from 1 to 20. Specific examples of alkyl groups 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.

[0057] The alkenyl group is intended to include both straight-chain and branched alkenyl groups, and may optionally be substituted with one or more other substituents. Specifically, the alkenyl group may 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, piperyl, or styryl, but is not limited thereto.

[0058] The alkynyl group is intended to include both straight-chain and branched alkynyl groups, and may optionally be substituted with one or more other substituents. The alkynyl group may be, for example, ethynyl or 2-propynyl, but is not limited thereto.

[0059] Cycloalkyl is intended to include monocyclic cycloalkyl and polycyclic cycloalkyl, and can be optionally substituted with one or more other substituents. As used herein, the term "polycyclic" means that the cycloalkyl group can be directly connected or fused to one or more other cyclic groups. The other cyclic groups can be cycloalkyl, and further examples thereof include heterocycloalkyl, aryl, and heteroaryl. The cycloalkyl group can specifically be cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, or cyclooctyl, but is not limited thereto.

[0060] Heterocycloalkyl is intended to include monocyclic heterocycloalkyl and polycyclic heterocycloalkyl, which are inserted with a heteroatom such as O, S, Se, N, or Si, and can be optionally substituted with one or more other substituents. As used herein, the term "polycyclic" means that the heterocycloalkyl group can be directly connected or fused to one or more other cyclic groups. The other cyclic groups can be heterocycloalkyl, and further examples thereof include cycloalkyl, aryl, and heteroaryl.

[0061] Aryl can be monocyclic aryl or polycyclic aryl. Examples of monocyclic aryl include, but are not limited to, phenyl, biphenyl, terphenyl, and stilbenyl. Examples of polycyclic aryl include naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, tetracenyl, fluorenyl, acenaphathcenyl, triphenylenyl, and fluoranthenyl, but the scope of the present application is not limited thereto.

[0062] Heteroaryl refers to a heterocyclic group inserted with one or more heteroatoms. Examples of heteroaryl include, but are not limited to, thienyl, furanyl, pyrrolyl, imidazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benz oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, dibenzofuranyl, phenanthrolinyl, thiazolyl, iso oxazolyl, oxadiazolyl, thiodiazolyl, benzothiazolyl, and phenothiazinyl.

[0063] Alkoxy can specifically be methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isopentyloxy, or hexyloxy, but is not limited thereto.

[0064] Silyl groups are intended to include alkyl-substituted silyl groups and aryl-substituted silyl groups. Particular examples of such silyl groups include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, and dimethylfurylsilyl.

[0065] Amino groups can be, for example, -NH2, alkylamino groups, and heteroaryl amino groups. Arylamino groups are aryl-substituted amino groups and alkylamino groups are alkyl-substituted amino groups. Examples of arylamino groups include substituted or unsubstituted monoaryl amino groups, substituted or unsubstituted diaryl amino groups, and substituted or unsubstituted triaryl amino groups. The aryl moieties in arylamino groups can be monocyclic or polycyclic aryl groups. Arylamino groups can contain two or more aryl moieties. In this case, the aryl moieties can all be monocyclic or polycyclic aryl groups. Alternatively, the arylamino groups can contain one or more monocyclic aryl moieties and one or more polycyclic aryl moieties. The aryl moieties in arylamino groups can be selected from those exemplified above for aryl groups.

[0066] The aryl moieties in aryloxy and arylthio groups are the same as those described above for aryl groups. Particular examples of aryloxy groups include, but are not limited to, phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethylphenoxy, 2,4,6-trimethylphenoxy, p-t- butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1- naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryloxy, 9-anthryloxy, 1- phenanthryloxy, 3-phenanthryloxy, and 9-phenanthryloxy. The arylthio group can be, for example, phenylthio, 2-methylphenylthio, or 4-t-butylphenylthio, but is not limited thereto.

[0067] Halogen groups can be, for example, fluorine, chlorine, bromine, or iodine.

[0068] More specifically, the polycyclic aromatic derivative represented by Formula A according to the present application can be selected from the following compounds 1 to 267:

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085] Specific substituents in Formula A can be clearly seen from the structures of Compounds 1 to 267, but are not intended to limit the scope of the compounds represented by Formula A.

[0086] As can be seen from the above specific compounds, the polycyclic aromatic derivatives of the present application contain B, P, or P=O and have a polycyclic aromatic structure. The introduction of substituents into the polycyclic aromatic structure enables the synthesis of organic light-emitting materials having inherent properties of the substituents. For example, the substituents are designed to be used 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 for organic electroluminescent devices. This introduction satisfies the requirements of materials for organic layers, making the organic electroluminescent device highly efficient.

[0087] Another aspect of the present application relates to an organic electroluminescent device including a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein one of the organic layers contains at least one of the organic electroluminescent compounds that can be represented by Formula A.

[0088] That is, according to one embodiment of the present application, the organic electroluminescent device has a structure in which one or more organic layers are arranged between a first electrode and a second electrode. The organic electroluminescent device of the present application can be manufactured using suitable materials known in the art by suitable methods known in the art, with the exception that the corresponding organic layers are formed using the organic electroluminescent compounds of Formula A.

[0089] The organic layer of the organic electroluminescent device according to the present application can form 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 application will be explained in more detail in the following Examples section.

[0090] The organic electroluminescent device of the present application will be described in more detail with reference to exemplary embodiments.

[0091] The organic electroluminescent device of the present application 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 application can also 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 application can also include one or two intermediate layers such as a hole blocking layer or an electron blocking layer. The organic electroluminescent device of the present application can also include one or more organic layers having various functions according to the desired characteristics of the device.

[0092] The light-emitting layer of the organic electroluminescent device according to the present application comprises an anthracene derivative represented by Formula C as a host compound:

[0093] [Formula C]

[0094]

[0095] wherein R 21 to R 28 are the same as or different from each other and are as defined in Formula A in regard to R1to R5, Ar9and Ar 10 are the same as or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C1-C 30 alkyl, a substituted or unsubstituted C6-C 50 aryl, a substituted or unsubstituted C2-C 30 alkenyl, a substituted or unsubstituted C2-C 20 alkynyl, a substituted or unsubstituted C3-C 30 cycloalkyl, a substituted or unsubstituted C5-C 30 cycloalkenyl, a substituted or unsubstituted C2-C 50 heteroaryl, a substituted or unsubstituted C2-C 30 heterocycloalkyl, a substituted or unsubstituted C1-C 30 alkoxy, a substituted or unsubstituted C6-C 30 aryloxy, a substituted or unsubstituted C1-C 30substituted or unsubstituted C6-C 30 substituted or unsubstituted C6-C 30 substituted or unsubstituted C6-C 30 substituted or unsubstituted C6-C 30 substituted or unsubstituted C6-C 30 substituted or unsubstituted C6-C 13 substituted or unsubstituted C6-C 20 substituted or unsubstituted C6-C 20 substituted or unsubstituted C6-C 20 substituted or unsubstituted C6-C 13 substituted or unsubstituted C6-C

[0096] Ar9in formula C is represented by formula C-1:

[0097] [Formula C-1]

[0098]

[0099] wherein R 31 to R 35 are identical to or different from each other and are as defined for R1to R5in formula A, and R 31 to R 35 each optionally be bonded to an adjacent substituent to form a saturated or unsaturated ring.

[0100] The compounds of formula C for use in the inventive organic electroluminescent device can specifically be selected from the group consisting of compounds of formulae C1 to C48:

[0101]

[0102]

[0103]

[0104] The specific structure of the organic electroluminescent device according to the present application, the method for manufacturing the device, and the material for the organic layer will be described below.

[0105] First, an anode material is coated on a substrate to form an anode. The substrate can be any substrate used in general electroluminescent devices. The substrate is preferably an organic substrate or a transparent plastic substrate which is excellent in transparency, surface flatness, handleability, and water resistance. A highly transparent and conductive metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (Sn02), or zinc oxide (ZnO) is used as the anode material.

[0106] A hole injection material is coated on the anode by vacuum thermal evaporation or spin coating to form a hole injection layer. Then, a hole transport material is coated on the hole injection layer by vacuum thermal evaporation or spin coating to form a hole transport layer.

[0107] The hole injection material is not particularly limited as long as it is generally used in the art. Specific examples of such materials include 4,4',4"-tris(2-naphthylphenyl-phenylamino)triphenylamine (2-TNATA), N,N'-di(l-naphthyl)-N,N'-diphenylbenzidine (NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-l,l'-biphenyl-4,4'-diamine (TPD), and N,N'-diphenyl-N,N'-bis[4-(phenyl-m-tolylamino)phenyl]biphenyl-4,4'-diamine (DNTPD).

[0108] The hole transport material is not particularly limited as long as it is generally used in the art. Examples of such materials include N,N'-bis(3-methylphenyl)-N,N'-diphenyl-(l,l-biphenyl)-4,4'-diamine (TPD) and N,N'-di(naphthalen-l-yl)-N,N'-diphenylbenzidine (a-NPD).

[0109] Subsequently, a hole auxiliary layer and a light-emitting layer are sequentially formed on the hole transport layer. A hole blocking layer can be optionally formed on the light-emitting layer by vacuum thermal evaporation or spin coating. The hole blocking layer is formed as a thin film and blocks holes from passing through the organic light-emitting layer into the cathode. This action of the hole blocking layer prevents degradation in the lifetime and efficiency of the device. A material having a very low highest occupied molecular orbital (HOMO) level is used for the hole blocking layer. The hole blocking material is not particularly limited 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.

[0110] Examples of the material for the hole blocking layer include, but are not limited to, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq2, OXD-7, and Liq.

[0111] An electron transport layer is deposited on the 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 deposited on the electron injection layer by vacuum thermal evaporation to form a cathode, thereby completing the manufacture of the organic electroluminescent device.

[0112] 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 emission type. In this case, a transmissive material such as ITO or IZO can be used to form the cathode.

[0113] The material for the electron transport layer functions to stably transport electrons injected from the cathode. The electron transport material can be any electron transport material known in the art, and examples thereof include, but are not limited to, quinoline derivatives, particularly tris(8-hydroxyquinoline)aluminum (Alq3), TAZ, Balq, bis(benzothiazole-10-yl)beryllium (Bebq2), ADN, and Oxadiazole derivatives, such as PBD, BMD, and BND.

[0114] Each of the organic layers can be formed by a monomolecular deposition method or a solution method. According to the monomolecular deposition method, the material for each layer is evaporated into a thin film under heat and vacuum or reduced pressure. According to the solution method, 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, spray coating, dip coating, or spin coating.

[0115] The organic electroluminescent device of the present application can be used in a display or a lighting system selected from a flat panel display, a flexible display, a monochromatic flat panel lighting system, a white flat panel lighting system, a flexible monochromatic lighting system, and a flexible white lighting system.

[0116] Embodiment of Invention

[0117] The present application will be explained more specifically with reference to the following examples. However, it will be apparent to those skilled in the art that these examples are in no way intended to limit the scope of the present application.

[0118] Synthesis Example 1. Synthesis of compound 25

[0119] (1) Synthesis Example 1-1. Synthesis of 1-a

[0120] 1-a was synthesized by Reaction 1.

[0121] [Reaction 1]

[0122]

[0123] Into a 1000 mL reactor was placed 50 g (188 mmol) of 1,3-dibromo-5- methoxybenzene, 31.8 g (188 mmol) of diphenylamine, 36.1 g (376 mmol) of sodium tert-butoxide, 1.9 g (4 mmol) of bis(tri-tert-butylphosphine)Pd(0), and 500 mL of toluene. The mixture was stirred at reflux for 12 hours. After the reaction was completed, the reaction solution was allowed to stand for layer separation. The organic layer was concentrated under reduced pressure and separated by column chromatography to give 33.3 g of 1-a (yield 50%).

[0124] (2) Synthesis Example 1-2. Synthesis of 1-b

[0125] 1-b was synthesized by Reaction 2.

[0126] [Reaction 2]

[0127]

[0128] Into a 1000 mL reactor was placed 50 g (235 mmol) of 3-bromobenzothiophene, 21.9 g (235 mmol) of aniline, 1.1 g (5 mmol) of palladium acetate, 45.1 g (469 mmol) of sodium tert-butoxide, 2 g (5 mmol) of bis(diphenylphosphino)-1,1'-binaphthalene, and 500 mL of toluene. The mixture was stirred at reflux for 12 hours. After the reaction was completed, the reaction solution was filtered. The filtrate was concentrated and separated by column chromatography to give 50 g of 1-b (yield 92%).

[0129] (3) Synthesis Example 1-3. Synthesis of 1-c

[0130] 1-c was synthesized by Reaction 3.

[0131] [Reaction 3]

[0132]

[0133] Into a 1000 mL reactor was placed 33.3 g (94 mmol) of 1-a, 21.2 g (94 mmol) of 1-b, 18.1 g (188 mmol) of sodium tert-butoxide, 1 g (2 mmol) of bis(tri-tert-butylphosphine)Pd(0), and 400 mL of toluene. The mixture was stirred at reflux for 12 hours. After the reaction was completed, the reaction solution was allowed to stand for layer separation. The organic layer was concentrated under reduced pressure and separated by column chromatography to give 39.5 g of 1-c (yield 80%).

[0134] (4) Synthesis Example 1-4. Synthesis of 1-d

[0135] 1-d was synthesized by Reaction 4.

[0136] [Reaction 4]

[0137]

[0138] In a dry 500 mL reactor, place 39.5 g (1.1 mmol) of 1-c, 200 mL of acetic acid and 200 mL of hydrogen bromide. Stir the mixture under reflux for 24 hours. After completion of the reaction, precipitate the reaction solution in excess water. Collect the solid by filtration and separate by column chromatography to obtain 35 g of 1-d (yield 81.5%).

[0139] (5) Synthesis Example 1-5. Synthesis of 1-e

[0140] Synthesize 1-e by Reaction 5.

[0141] [Reaction 5]

[0142]

[0143] In a 250 mL reactor, place 35 g (95 mmol) of 1-d, 25 g (120 mmol) of potassium carbonate, 25 g (142.5 mmol) of 1-bromo-3-fluorobenzene and 400 mL of 1-methyl-2-pyrrolidinone. Stir the mixture under reflux for 24 hours. After completion of the reaction, precipitate the reaction solution in excess water. Collect the solid by filtration and separate by column chromatography to obtain 31 g of 1-e (yield 85.4%).

[0144] (6) Synthesis Example 1-6. Synthesis of 1-f

[0145] Synthesize 1-f by Reaction 6.

[0146] [Reaction 6]

[0147]

[0148] In a 1000 mL reactor, place 30 g (111 mmol) of 1,3-dibromo-5-chlorobenzene, 39.4 g (233 mmol) of diphenylamine, 32 g (333 mmol) of sodium tert-butoxide, 1.7 g (3 mmol) of bis(tris-tert-butylphosphine)Pd(0) and 400 mL of toluene. Stir the mixture under reflux for 12 hours. After completion of the reaction, let the reaction solution stand for layer separation. Concentrate the organic layer under reduced pressure and separate by column chromatography to obtain 38.5 g of 1-f (yield 82.3%).

[0149] (7) Synthesis Example 1-7. Synthesis of 1-g

[0150] Synthesize 1-g by Reaction 7.

[0151] [Reaction 7]

[0152]

[0153] Into a 1000 mL reactor was placed 38.5 g (83 mmol) of 1-f, 8 g (83 mmol) of aniline, 16.6 g (172 mmol) of sodium tert-butoxide, 0.9 g (2 mmol) of bis(tri-tert-butylphosphine)Pd(0), and 400 mL of toluene. The mixture was stirred at reflux for 12 hours. After the reaction was completed, the reaction solution was allowed to stand for layer separation. The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 40.2 g of 1-g (yield 92.3%).

[0154] (8) Synthesis Example 1-8. Synthesis of 1-h

[0155] Compound 25 was synthesized by Reaction 9.

[0156] [Reaction 9]

[0157]

[0158] Into a 1000 mL reactor was placed 43.4 g (41 mmol) of 1-h and 450 mL of dichlorobenzene, and 20.5 g (82 mmol) of boron tribromide was added dropwise thereto at 0°C. The mixture was stirred at room temperature for 2 hours and at 180°C for 18 hours. After the reaction was completed, an aqueous sodium acetate solution was added to the reaction mixture at room temperature. The resulting mixture was stirred and extracted with ethyl acetate. The organic layer was concentrated and separated by column chromatography to obtain 5.3 g of compound 25 (yield 15.7%).

[0159] (9) Synthesis Example 1-9. Synthesis of compound 25

[0160] Compound 25 was synthesized by Reaction 9.

[0161] [Reaction 9]

[0162]

[0163] Into a 1000 mL reactor was placed 43.4 g (41 mmol) of 1-h and 450 mL of dichlorobenzene, and 20.5 g (82 mmol) of boron tribromide was added dropwise thereto at 0°C. The mixture was stirred at room temperature for 2 hours and at 180°C for 18 hours. After the reaction was completed, an aqueous sodium acetate solution was added to the reaction mixture at room temperature. The resulting mixture was stirred and extracted with ethyl acetate. The organic layer was concentrated and separated by column chromatography to obtain 5.3 g of compound 25 (yield 15.7%).

[0164] Synthesis Example 2: Synthesis of compound 42

[0165] (1) Synthesis Example 2-1. Synthesis of 2-a

[0166] 2-a was synthesized by Reaction 10.

[0167] [Reaction 10]

[0168]

[0169] 2-a was synthesized in the same manner as in Synthesis Example 1-3, except that 3-bromo-5-chloro-N,N-diphenyl aniline was used instead of 1-a, in an amount of 18.5 g (yield 74.1%).

[0170] (2) Synthesis Example 2-2. Synthesis of 2-b

[0171] 2-b was synthesized by Reaction 11.

[0172] [Reaction 11]

[0173]

[0174] 2-b was synthesized in the same manner as in Synthesis Example 1-7, except that 2-a was used instead of 1-f, in an amount of 24.1 g (yield 84%).

[0175] (3) Synthesis Example 2-3. Synthesis of 2-c

[0176] 2-c was synthesized by Reaction 12.

[0177] [Reaction 12]

[0178]

[0179] 2-c was synthesized in the same manner as in Synthesis Example 1-8, except that 2-b was used instead of 1-g, in an amount of 30.5 g (yield 78.4%).

[0180] (4) Synthesis Example 2-4. Synthesis of compound 42

[0181] Compound 42 was synthesized by Reaction 13.

[0182] [Reaction 13]

[0183]

[0184] Compound 42 was synthesized in the same manner as in Synthesis Example 1-9, except that 2-c was used instead of 1-h, in an amount of 3.4 g (yield 12.5%).

[0185] Synthesis Example 3: Synthesis of compound 55

[0186] (1) Synthesis Example 3-1. Synthesis of 3-a

[0187] 3-a was synthesized by Reaction 14.

[0188] [Reaction 14]

[0189]

[0190] Synthesis of 23.4 g of 3-a (yield 69.5%) was performed in the same manner as in Synthesis Example 1-5, except that 3,4-dibromothiophene was used instead of 1-bromo-3-fluorobenzene.

[0191] (2) Synthesis Example 3-2. Synthesis of 3-b

[0192] Synthesis of 3-b was performed by Reaction 15.

[0193] [Reaction 15]

[0194]

[0195] Synthesis of 28.6 g of 3-b (yield 77.4%) was performed in the same manner as in Synthesis Example 1-8, except that 3-a was used instead of 1-e.

[0196] (3) Synthesis Example 3-3. Synthesis of compound 55

[0197] Synthesis of Compound 55 was performed by Reaction 16.

[0198] [Reaction 16]

[0199]

[0200] Synthesis of 4.1 g of Compound 55 (yield 14.5%) was performed in the same manner as in Synthesis Example 1-9, except that 3-b was used instead of 1-h.

[0201] Synthesis Example 4: Synthesis of compound 86

[0202] (1) Synthesis Example 4-1. Synthesis of 4-a

[0203] Synthesis of 4-a was performed by Reaction 17.

[0204] [Reaction 17]

[0205]

[0206] Synthesis of 35.6 g of 4-a (yield 67.1%) was performed in the same manner as in Synthesis Example 1-3, except that 3-bromo-5-chloro-N,N-diphenyl aniline and N-phenylbenzofuran-3-amine were used instead of 1-a and 1-b.

[0207] (2) Synthesis Example 4-2. Synthesis of 4-b

[0208] Synthesis of 4-b was performed by Reaction 18.

[0209] [Reaction 18]

[0210]

[0211] Synthesis of 28.6 g of 4-b (yield 74.8%) was performed in the same manner as in Synthesis Example 1-7, except that 4-a was used instead of 1-f.

[0212] (3) Synthesis Example 4-3. Synthesis of 4-c

[0213] Synthesis of 4-c was performed by Reaction 19.

[0214] [Reaction 19]

[0215]

[0216] Synthesis of 21.4 g of 4-c (yield 72.7%) was performed in the same manner as in Synthesis Example 1-8, except that 4-b was used instead of 1-g.

[0217] (4) Synthesis Example 4-4. Synthesis of compound 86

[0218] Synthesis of Compound 86 was performed by Reaction 20.

[0219] [Reaction 20]

[0220]

[0221] Synthesis of 2.7 g of Compound 86 (yield 12.5%) was performed in the same manner as in Synthesis Example 1-9, except that 4-c was used instead of 1-h.

[0222] Synthesis Example 5: Synthesis of compound 92

[0223] (1) Synthesis Example 5-1. Synthesis of 5-a

[0224] Synthesis of 1-a was performed by Reaction 21.

[0225] [Reaction 21]

[0226]

[0227] Synthesis of 35.7 g of 5-a (yield 78.1%) was performed in the same manner as in Synthesis Example 1-3, except that N-phenylbenzofuran-3-amine and 1-bromo-3-fluorobenzene were used instead of 1-a and 1-b.

[0228] (2) Synthesis Example 5-2. Synthesis of 5-b

[0229] Synthesis of 5-b was performed by Reaction 22.

[0230] [Reaction 22]

[0231]

[0232] 29.4 g of 5-b (yield 67.8%) was synthesized in the same manner as in Synthetic Examples 1-5, except that 1,3-dihydroxybenzene and 5-a were used instead of 1-bromo-3-fluorobenzene and 1-d.

[0233] Synthesis Example 5-3. Synthesis of compound 92

[0234] Compound 92 was synthesized through reaction 23.

[0235] [Reaction 23]

[0236]

[0237] Compound 92 (3.3 g) was synthesized in the same manner as in Synthetic Examples 1-9 (yield 22.5%), except that 5-b was used instead of 1-h.

[0238] Examples 1 to 5: Manufacture of organic electroluminescent devices

[0239] The ITO glass was patterned to have a 2mm × 2mm luminescent area, and then cleaned. 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 Deposited onto ITO in this order. Formed using a mixture of the main component represented by BH1 and the compounds of the present invention shown in Table 1 (3 wt%). 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 used to form a 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 on 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.

[0240]

[0241] Comparative Examples 1 to 2

[0242] The organic electroluminescent device was manufactured in the same manner as in Examples 1 to 5, except that BD1 or BD2 was used instead of the compound of the present invention. The luminescence characteristics of the organic electroluminescent device were measured at 0.4 mA. The structures of BD1 and BD2 are as follows:

[0243]

[0244]

[0245] The driving voltage and external quantum efficiency of the organic electroluminescent devices of Examples 1 to 5 and Comparative Examples 1 to 2 were measured. The results are shown in Table 1.

[0246] [Table 1]

[0247] Example No. Dopant Driving voltage (V) External quantum efficiency (%) Example 1 Compound 25 3.8 7.2 Example 2 Compound 42 3.8 7.1 Example 3 Compound 55 3.8 6.9 Example 4 Compound 86 3.8 7.0 Example 5 Compound 92 3.8 6.8 Comparative Example 1 BD1 3.8 5.3 Comparative Example 2 BD2 3.8 6.2

[0248] As can be seen from the results of Table 1, the organic electroluminescent devices of Examples 1 to 6 each using the compound of the present application have high luminous efficiency compared to the devices of Comparative Examples 1 and 2 each using BD1 and BD2, respectively.

[0249] Industrial applicability

[0250] The polycyclic aromatic derivative of the present application can be used in an organic layer of an organic electroluminescent device to achieve high efficiency of the device. Accordingly, the polycyclic aromatic derivative of the present application can find useful industrial applications in various displays including flat panel displays and flexible displays, and lighting systems including monochromatic flat lighting systems, white flat lighting systems, flexible monochromatic lighting systems, and flexible white lighting systems.

Claims

1. A polycyclic aromatic derivative selected from the following compounds:

2. An organic electroluminescence device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein one of the organic layers comprises the compound according to claim 1.

3. The organic electroluminescence device according to claim 2, wherein the organic layers comprise 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, at least one of which comprises the compound according to claim 1.

4. The organic electroluminescence device according to claim 3, wherein the light-emitting layer comprises an anthracene derivative represented by Formula C as a host compound: [Formula C] wherein R 21 to R 28 are the same or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1-C 30 alkyl, substituted or unsubstituted C6-C 50 aryl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C2-C 50 heteroaryl, substituted or unsubstituted C1-C 30 alkoxy, substituted or unsubstituted C6-C 30 aryloxy, substituted or unsubstituted C1-C 30 alkylthio, substituted or unsubstituted C5-C 30 arylthio, substituted or unsubstituted C1-C 30 alkylamino, substituted or unsubstituted C5-C 30 arylamino, substituted or unsubstituted C1-C 30 alkylsilyl, substituted or unsubstituted C5-C 30 arylsilyl, nitro, cyano, and halogen, Ar9 and Ar 10 They may be the same as or different from each other and are each independently selected from hydrogen, deuterium, C1-C 30 Alkyl, C6-C 50 Aryl, C2-C 30 alkenyl, C2-C 20 alkynyl group, C3-C 30 cycloalkyl, C5-C 30 Cycloalkenyl, C2-C 50 heteroaryl, C2-C 30 Heterocyclic alkyl, C1-C 30 Alkoxy, C6-C 30 aryloxy group, C1-C 30 Alkyl thio, C6-C 30 Arylthio, C1-C 30 Alkylamine group, C6-C 30 arylamine, C1-C 30 Alkyl silyl, and C6-C 30 Arylsilyl, L 13 is a single bond or is selected from C6-C 20 arylene and C2-C 20 heteroarylene, and k is an integer from 1 to 3, with the proviso that when k is 2 or more, the linking group L 13 the same or different from each other, "Substituted" indicates substitution by one or more of the following substituents: deuterium, cyano, halogen, hydroxyl, nitro, C1-C 24 Alkyl, C3-C 24 cycloalkyl, C1-C 24 Haloalkyl, C1-C 24 alkenyl, C1-C 24 Alkyne group, C1-C 24 Heteroalkyl, C1-C 24 Heterocyclic alkyl, C6-C 24 Aryl, C6-C 24 Arylalkyl, C2-C 24 heteroaryl, C2-C 24 Heteroarylalkyl, C1-C 24 Alkoxy, C1-C 24 Alkylamino, C1-C 24 arylamino, C1-C 24 heteroarylamino, C1-C 24 Alkyl silyl, C1-C 24 Arylsilyl and C1-C 24 Aryloxy groups, or combinations thereof.

5. The organic electroluminescence device according to claim 4, wherein Ar9 in Formula C is represented by Formula C-1: [Formula C-1] wherein R 31 to R 35 each independently hydrogen.

6. The organic electroluminescence device according to claim 3, wherein the light-emitting layer comprises an anthracene derivative selected from the compounds represented by Formulas C1 to C48 as a host compound:

7. The organic electroluminescence device according to claim 3, wherein one or more of the layers are formed by a deposition method or a solution method.

8. The organic electroluminescence device according to claim 2, wherein the organic electroluminescence device is used in a display or a lighting system selected from a flat panel display, a flexible display, a monochromatic flat panel lighting system, a white flat panel lighting system, a flexible monochromatic lighting system, and a flexible white lighting system.

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