KR20220086223A - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel compound having excellent light emitting ability and an organic electroluminescent device comprising the same, wherein the compound according to the present invention is an organic material layer material of an organic electroluminescent device, preferably when used as a phosphorescent host of the light emitting layer, light emitting performance, driving voltage, Efficiency and lifetime characteristics can be improved.

Description

Organic light emitting compound and organic electroluminescent device using same

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, to a compound having excellent electron transport ability and an organic compound having improved characteristics such as luminous efficiency, driving voltage, and lifespan by including the compound in one or more organic material layers. It relates to an electroluminescent device.

Recently, as an image display device, an organic electroluminescence display has been actively developed. An organic electroluminescent display device is different from a liquid crystal display device, and by recombination of holes and electrons injected from the first electrode and the second electrode in the light emitting layer, the light emitting material containing the organic compound is emitted in the light emitting layer to realize display. It is a so-called self-emission type display device.

In applying the organic electroluminescent device to a display device, low driving voltage, high luminous efficiency, and long life of the organic electroluminescent device are required, and the development of a material for an organic electroluminescent device that can stably implement this is continuously required. have.

In particular, in recent years, in order to realize a high-efficiency organic electroluminescent device, phosphorescence emission using triplet state energy or delayed fluorescence using triplet-triplet annihilation (TTA) in which singlet excitons are generated by collision of triplet excitons The technology for light emission is being developed, and the development of a thermally activated delayed fluorescence (TADF) material using delayed fluorescence is in progress.

Republic of Korea Patent Publication No. 10-2015-0033082 (published date: 04. 01, 2015)

An object of the present invention is to provide an excellent novel organic compound that can apply a novel organic compound to an organic electroluminescent device, and improves high efficiency and long life characteristics by using the novel organic compound in an organic layer of an organic electroluminescent device.

Another object of the present invention is to provide an organic electroluminescent device including a thermally activated delayed fluorescence emitting material and a thermally activated delayed fluorescence emitting material including the novel organic compound.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

Ar ₁ To Ar ₅ Are the same as or different from each other, and each independently a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₃₀ aryl group, heteroaryl group having 2 to 30 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphine group , C ₆ ~ C ₆₀ Mono or diarylphosphinyl group and C ₆ ~ C ₆₀ Selected from the group consisting of an arylamine group,

The Ar ₁ To Ar ₅ Alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group , mono or diarylphosphinyl group and arylamine group are each independently a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Arylox Period, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Arylphos Pin group, C ₆ ~ C ₆₀ Mono or diarylphosphinyl group and C ₆ ~ C ₆₀ When substituted with one or more substituents selected from the group consisting of an arylamine group or unsubstituted, and substituted with a plurality of substituents, they are the same as each other or may be different,

Y ₁ To Y ₃ Are the same as or different from each other, and each independently a direct bond, O or S,

m and n are 0 or 2.

In addition, the present invention is an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is the first It provides an organic electroluminescent device comprising the compound represented by the formula (1) of claim 1.

The organic material layer may include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and a light emitting layer.

The light emitting layer may emit delayed fluorescence.

The emission layer may be a delayed fluorescence emission layer including a host and a dopant, and the dopant may include the compound represented by Formula 1 of claim 1 .

The light emitting layer may be a thermally activated delayed fluorescent light emitting layer that emits blue light.

In the present invention, "substituted or unsubstituted" means a deuterium atom, a halogen atom, a cyano group, a nitro group, an amine group, a silyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an aryl group, and It may mean unsubstituted or substituted with one or more substituents selected from the group consisting of heterocyclic groups. In addition, each of the exemplified substituents may be substituted or unsubstituted, but is not limited thereto. Preferably, the biphenyl group may mean an aryl group or a phenyl group.

Examples of the halogen atom in the present invention may be a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, but is not limited thereto.

In the present invention, the alkyl group may be linear, branched or cyclic. Carbon number of an alkyl group is 1 or more and 50 or less, 1 or more and 30 or less, 1 or more and 20 or less, 1 or more and 10 or less, or 1 or more and 6 or less. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, t-butyl group, i-butyl group, 2-ethylbutyl group, 3, 3-dimethylbutyl group , n-pentyl group, i-pentyl group, neopentyl group, t-pentyl group, cyclopentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, 4-methyl-2-pentyl group , n-hexyl group, 1-methylhexyl group, 2-ethylhexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl group, n-heptyl group, 1 -Methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyl group Siloctyl group, 3,7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-ox Tyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n -Pentadecyl group, n-hexadecyl group, 2-ethyl hexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group , n-nonadecyl group, n-icosyl group, 2-ethyl icosyl group, 2-butyl icosyl group, 2-hexyl icosyl group, 2-octyl icosyl group, n-henicosyl group, n-docosyl group, n-tricho It may be a practical group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, and n-triacontyl group, but is limited thereto. it doesn't happen

In the present invention, the aryl group means any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms of the aryl group may be 6 or more and 30 or less, 6 or more and 20 or less, or 6 or more and 15 or less. Examples of the aryl group include a phenyl group, a naphthyl group, a fluorenyl group, an anthracenyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a quinkphenyl group, a sexyphenyl group, a triphenylenyl group, a pyrenyl group, a benzofluoranthenyl group , may be a chrysenyl group, but is not limited thereto.

In the present invention, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure, but is not limited thereto. Preferably, when the fluorenyl group is substituted, it may have the following structure, but is not limited thereto.

In the present invention, the heteroaryl group may be a heteroaryl group including at least one of O, N, P, Si, and S as a heterogeneous element. The number of ring carbon atoms in the heteroaryl group is 2 or more and 30 or less, or 2 or more and 20 or less. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The polycyclic heteroaryl group may have, for example, a bicyclic or tricyclic structure. Examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, a triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phenoxazyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , isoquinoline group, indole group, carbazole group, N-arylcarbazole group, N-heteroarylcarbazole group, N-alkylcarbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophenyl group, thienothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, di It may be a benzosilol group and a dibenzofuranyl group, but is not limited thereto.

In the present invention, the number of carbon atoms in the amine group is not particularly limited, but may be 1 or more and 30 or less. The amine group may include an alkyl amine group and an aryl amine group. Examples of the amine group include, but are not limited to, a methylamine group, a dimethylamine group, a phenylamine group, a naphthylamine group, a 9-methyl-anthracenylamine group, and a triphenylamine group.

The organic compound of the present invention can be used as a material for an organic material layer of an organic electroluminescent device because it improves high efficiency and long life characteristics. In particular, when the organic compound of the present invention is used as a phosphorescent host of the light emitting layer, an organic electroluminescent device having excellent light emitting performance, driving voltage, efficiency and lifespan characteristics can be manufactured, and furthermore, a full color display panel with improved performance and lifespan can be manufactured. can

1 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
2 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

1. Organic Compounds

Since the present invention can have various changes and can have various forms, specific embodiments are illustrated in the drawings and described in detail in the text. However, this is not intended to limit the present invention to the specific disclosed form, it should be understood to include all modifications, equivalents and substitutes included in the spirit and scope of the present invention.

The organic compound of the present invention is a compound in which N-B-N is condensed to an aromatic ring to form a parent nucleus, and various substituents are bonded to the parent nucleus, and is represented by Formula 1 above.

In the organic compound of the present invention, a portion of the ring structure formed by N-B-N is an electron donor, and a portion bonded to nitrogen and/or a portion of the electron donor serves as an electron acceptor.

The organic compound includes an electron acceptor bonded to nitrogen of the electron donor site, thereby localizing the electron density in the molecule, and the absolute value (ΔEst) of the difference between the singlet energy level (S1) and the triplet energy level (T1) is small. The rate constant of reverse intersystem crossing (RISC) in which the triplet energy level (T1) is converted to the singlet energy level (S1) increases, thereby contributing to the long lifespan of the organic electroluminescent device.

Therefore, when the organic compound of the present invention is applied to the organic material layer of the organic electroluminescent device, the light emitting characteristics of the organic electroluminescent device are improved, and the hole injection/transport ability and electron injection/transport ability are improved, so that the driving voltage is low and the lifespan is reduced. It is possible to provide an organic electroluminescent device.

The organic compound of the present invention may be applied to an organic material layer of an organic electroluminescent device, and the compound represented by Formula 1 may be a delayed fluorescence emitting material. Preferably, the organic compound may be a thermally activated delayed fluorescence material.

In addition, the organic compound of the present invention has a small difference between the singlet energy level (S1) and the triplet energy level (T1), so that it can be used as a thermally activated delayed fluorescent light emitting material. Preferably, the organic compound may be a thermally activated delayed fluorescent material emitting blue light, green light or red light. More preferably, the compound represented by Formula 1 may be used as a blue light emitting material emitting thermally activated delayed fluorescence, but is not limited thereto.

The compound represented by Formula 1 of the present invention may be embodied as a compound represented by Formula 2 below.

[Formula 2]

In Formula 2,

Ar ₁ to Ar ₄ , Y ₁ to Y ₃ , m and n are as defined in Formula 1 above.

Also, in the compound represented by Formula 1 of the present invention, Y ₃ may be O or S.

In the compound represented by Formula 1 of the present invention, Ar ₁ , Ar ₂ , and Ar ₅ are the same as or different from each other, and it is preferable that each independently be represented by any one of Formulas A-1 to A-2.

[Formula A-1]

[Formula A-2]

In Formulas A-1 to A-2,

The dotted line means the part where the condensation takes place,

Z ₁ are the same as or different from each other, each independently C or N,

R ₁ To R ₂ Are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted C ₁ ~ C ₃₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₃₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₃₀ alkynyl group, substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₃₀ A substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having 2 to 30 nuclear atoms.

In the compound represented by Formula 1 of the present invention, Ar ₃ to Ar ₄ are the same as or different from each other, and it is preferable that each independently be represented by any one of Formulas B-1 to B-2.

[Formula B-1]

[Formula B-2]

In the above formulas B-1 to B-2,

* is the part where the bond is made,

Z ₂ are the same as or different from each other, each independently C or N,

R ₃ To R ₄ Are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted C ₁ ~ C ₃₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₃₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₃₀ alkynyl group, substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₃₀ A substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having 2 to 30 nuclear atoms.

In the compound represented by Formula 1 of the present invention, when Z ₁ to Z ₂ of Ar ₁ to Ar ₅ are all C, at least one of R ₁ to R ₅ is substituted or unsubstituted with 2 to 30 nuclear atoms It is preferred that the compound is a heteroaryl group.

Specific examples of the compound represented by Formula 1 of the present invention may be further specified as a compound represented by any one selected from the group consisting of the compounds exemplified below. However, the compound represented by Formula 1 of the present invention is not limited by those exemplified below.

2. Organic electroluminescent device

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

The organic compound of the present invention can be used in an organic electroluminescent device to improve the efficiency and lifespan of the organic electroluminescent device. Specifically, the organic compound of the present invention can be used in the light emitting layer (EML) of the organic electroluminescent device to improve the luminous efficiency and lifespan of the organic electroluminescent device.

The organic electroluminescent device may include a first electrode EL1 , a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2 that are sequentially stacked. The first electrode EL1 and the second electrode EL2 may face each other, and a plurality of organic layers may be disposed between the first electrode EL1 and the second electrode EL2 . The plurality of organic layers may include a hole transport region HTR, an emission layer EML, and an electron transport region ETR. Preferably, the organic electroluminescent device may include the compound represented by Formula 1 in the light emitting layer (EML).

In addition, in the organic electroluminescent device, the first electrode EL1 has conductivity. The first electrode EL1 may be formed of a metal alloy or a conductive compound. The first electrode EL1 may be an anode.

The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, the first electrode EL1 is preferably a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc (ITZO). oxide) and the like. When the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, or a compound or mixture thereof (eg, a mixture of Ag and Mg). Alternatively, a plurality of transparent conductive layers including a reflective or semi-transmissive layer formed of the above-described material and a transparent conductive layer formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. It may have a layer structure. Preferably, the first electrode EL1 may include a plurality of layers of ITO/Ag/ITO.

In the organic electroluminescent device, the hole transport region HTR is provided on the first electrode EL1 . The hole transport region HTR may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a hole buffer layer, and an electron blocking layer (EBL). The hole transport region HTR may include a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

The hole transport region HTR may have a single-layer structure of the hole injection layer HIL or the hole transport layer HTL, or may have a single-layer structure including a hole injection material and a hole transport material. In addition, the hole transport region HTR has a single layer structure made of a plurality of different materials, or a hole injection layer HIL/hole transport layer HTL, which are sequentially stacked from the first electrode EL1 , hole injection layer (HIL) / hole transport layer (HTL) / hole buffer layer, hole injection layer (HIL) / hole buffer layer, hole transport layer (HTL) / hole buffer layer, or hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL), but is not limited thereto.

The hole transport region (HTR) may be formed by various methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, an inkjet printing method, a laser printing method, and a laser induced thermal imaging (LITI) method. can be formed using

Meanwhile, the hole injection layer (HIL) of the organic electroluminescent device may include a known hole injection material. Preferably, the hole injection layer (HIL) is triphenylamine-containing polyetherketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodoniumtetrakis(pentafluorophenyl)borate (PPBI), N, N Phthalocyanine compounds, such as '-diphenyl-N, N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-phenyl-4, 4'-diamine (DNTPD), copper phthalocyanine, 4, 4 ',4''-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), N ,N'-bis(1-naphthyl)-N,N'-diphenyl-4,4'-diamine (α-NPD), 4,4',4''-tris{N,N diphenyl amino} Triphenylamine (TDATA), 4,4',4''-tris(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA) , poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI) /PSS) and HAT-CN (dipyrazino[2,3-f: 2',3'-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile) It is not limited.

The hole transport layer (HTL) of the organic electroluminescent device may include a known hole transport material. Preferably, the hole transport layer (HTL) is 1,1-bis[(di-4-trilamino)phenyl]cyclohexane (TAPC), N-phenylcarbazole (N-Phenylcarbazole), polyvinyl carbazole (Polyvinyl carbazole) carbazole derivatives such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), 4,4', 4''-tris(N-carbazolyl)triphenylamine (TCTA) N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB) and N,N'-bis( 1-naphthyl)-N,N'-diphenyl-4,4'-diamine (α-NPD) may be included, but is not limited thereto.

Meanwhile, the hole transport region HTR may further include an electron blocking layer EBL, and the electron blocking layer EBL may be disposed between the hole transport layer HTL and the emission layer EML. The electron blocking layer EBL serves to prevent electron injection from the electron transport region ETR to the hole transport region HTR.

The electron blocking layer (EBL) may include a general material known in the art to which the present invention pertains. The electron blocking layer (EBL) is, for example, a carbazole-based derivative such as N-phenylcarbazole or polyvinylcarbazole, a fluorine-based derivative, or TPD (N,N'-bis(3-methylphenyl)-N). Triphenylamine derivatives such as ,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine), TCTA(4,4',4"-tris(Ncarbazolyl)triphenylamine), NPD(N, N'-di(naphthalene-l-yl)-N,N'-diplienyl-benzidine), TAPC(4,4'-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), HMTPD(4, 4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl) and mCP In addition, the electron blocking layer (EBL) is an organic compound of the present invention may include

The hole transport region HTR may have a thickness of about 100 Å to about 10000 Å. Preferably, it may be from about 100 Angstroms to about 5000 Angstroms. The thickness of the hole injection layer (HIL) may be about 30 Å to about 1000 Å, the thickness of the hole transport layer (HTL) may be about 30 Å to about 1000 Å, and the thickness of the electron blocking layer (EBL) may be about 10 Å to about 1000 Å. can When the thickness of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) satisfies the above ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage. have.

In addition to the aforementioned materials, the hole transport region HTR may further include a charge generating material to improve conductivity. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region HTR. Preferably, the charge generating material may be a p-dopant. The p-dopant may be any one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. Preferably, non-limiting examples of the p-dopant include quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-tetracyanoquinodimethane), and metal oxides such as tungsten oxide and molybdenum oxide. may be mentioned, but is not limited thereto.

The hole transport region (HTR) may further include any one or more of a hole buffer layer and an electron blocking layer (EBL) in addition to the hole injection layer (HIL) and the hole transport layer (HTL). The hole buffer layer may increase light emission efficiency by compensating for a resonance distance according to a wavelength of light emitted from the emission layer EML. As a material included in the hole buffer layer, a material capable of being included in the hole transport region (HTR) may be used.

In the organic electroluminescent device, the emission layer EML is provided on the hole transport region HTR. Preferably, the thickness of the emission layer EML may be greater than or equal to about 100 Å and less than or equal to 600 Å. The emission layer EML may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

The emission layer EML may emit one of red light, green light, blue light, white light, yellow light, and cyan light. The emission layer EML may include a fluorescent light emitting material or a phosphorescent light emitting material.

The emission layer EML may be a fluorescent emission layer. Some of the light emitted from the emission layer EML may be due to thermally activated delayed fluorescence (TADF). Preferably, the light emitting layer (EML) may include a light emitting component that emits thermally activated delayed fluorescence, and more preferably, the light emitting layer (EML) may be a light emitting layer that emits thermally activated delayed fluorescence that emits green light or red light.

The emission layer EML may include a host and a dopant, the host may be a host for delayed fluorescence emission, and the dopant may be a dopant for delayed fluorescence emission. Meanwhile, the organic compound of the present invention may be included as a dopant material of the emission layer (EML). Preferably, the organic compound of the present invention may be one used as a TADF dopant.

The emission layer EML may include a known host material. Preferably, the light emitting layer (EML) is a host material, Alq3 (tris (8-hydroxyquinolino) aluminum), CBP (4,4'-bis (N-carbazolyl) -1,1'-biphenyl), PVK (poly (n) -vinylcabazole), ADN(9,10-di(naphthalene-2-yl)anthracene), TCTA(4,4',4''-Tris(carbazol-9-yl)-triphenylamine), TPBi(1,3, 5-tris(N-phenylbenzimidazole-2-yl)benzene), TBADN(3-tert-butyl-9,10-di(naphth-2-yl)anthracene), DSA(distyrylarylene), CDBP(4,4'- bis(9-carbazolyl)-2,2'-dimethyl-biphenyl), MADN(2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), DPEPO (bis[2-(diphenylphosphino)phenyl] ether oxide), CP1 (Hexaphenyl cyclotriphosphazene), UGH2 (1,4-Bis(triphenylsilyl)benzene), DPSiO3 (Hexaphenylcyclotrisiloxane), DPSiO4 (Octaphenylcyclotetrasiloxane) and PPF (2,8-Bis(diphenylphosphoryl)dibenzofuran) On the other hand, in addition to the host material, a known delayed fluorescence emission host material may be included.

The emission layer EML may further include a known dopant material. Preferably, the emission layer (EML) is a dopant, and a styryl derivative (eg, 1,4-bis[2-(3-Nethylcarbazoryl)vinyl]benzene(BCzVB), 4-(di-p-tolylamino)-4 '-[(di-p-tolylamino)styryl]stilbene(DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl) vinyl)phenyl)phenylbenzenamine (NBDAVBi), perylene and its derivatives (eg 2, 5, 8, 11-Tetra-t-butylperylene (TBP)) and pyrene and its derivatives (eg 1, 1 2,5,8,11-Tetra-tbutylperylene (TBP)) such as -dipyrene, 1,4-dipyrenylbenzene, 1,4-Bis(N,N-Diphenylamino)pyrene), etc. It is not limited.

In addition, in the organic electroluminescent device, the electron transport region ETR is provided on the emission layer EML. The electron transport region ETR may include at least one of an electron blocking layer, an electron transport layer ETL, and an electron injection layer EIL, but is not limited thereto.

The electron transport region ETR may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials. Preferably, the electron transport region ETR may have a single layer structure of the electron injection layer EIL or the electron transport layer ETL, or may have a single layer structure including an electron injection material and an electron transport material. In addition, the electron transport region ETR has a single layer structure made of a plurality of different materials, or an electron transport layer ETL/electron injection layer EIL and hole blocking layer sequentially stacked from the first electrode EL1 . It may have a layer/electron transport layer (ETL)/electron injection layer (EIL) structure, but is not limited thereto. Preferably, the thickness of the electron transport region ETR may be about 100 Å to about 1500 Å.

Meanwhile, the electron transport region (ETR) is formed by various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, and laser induced thermal imaging (LITI). can be formed using

When the electron transport region ETR includes the electron transport layer ETL, the electron transport region ETR includes Alq3 (Tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)- phen-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzoimidazolyl) -1-ylphenyl)-9,10-dinaphthylanthracene, TPBi(1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), BCP(2,9-Dimethyl-4 ,7-diphenyl-1,10-phenanthroline), Bphen(4,7-Diphenyl-1,10-phenanthroline), TAZ(3-(4-Biphenylyl)-4-phenyl-5-tertbutylphenyl-1,2,4 -triazole), NTAZ(4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD(2-(4-Biphenylyl)-5-(4- tert-butylphenyl)-1,3,4-oxadiazole), BAlq(Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-Biphenyl-4-olato)aluminum), Bebq2(berylliumbis( benzoquinolin-10-olate), ADN (9,10-di(naphthalene-2-yl)anthracene), and mixtures thereof, but is not limited thereto.

When the electron transport region ETR includes the electron transport layer ETL, the thickness of the electron transport layers ETL may be about 100 Å to about 1000 Å. Preferably, the thickness of the electron transport layers (ETL) may be about 150 Å to about 500 Å. When the thickness of the electron transport layers ETL satisfies the above-described range, a satisfactory electron transport characteristic may be obtained without a substantial increase in driving voltage.

When the electron transport region ETR includes the electron injection layer EIL, the electron transport region ETR includes a lanthanide metal such as LiF, lithium quinolate (LiQ), Li O, BaO, NaCl, CsF, Yb, or A metal halide such as RbCl, RbI, or KI may be used, but is not limited thereto.

The electron injection layer EIL may also be made of a material in which an electron transport material and an insulating organo metal salt are mixed. The organometallic salt may be a material having an energy band gap of about 4 eV or more. Preferably, the organometallic salt may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate.

When the electron transport region ETR includes the electron injection layer EIL, the electron injection layers EIL may have a thickness of about 1 Å to about 100 Å. Preferably, the thickness of the electron injection layers EIL may be about 3 Å to about 90 Å. When the thickness of the electron injection layers EIL satisfies the above-described range, a satisfactory electron injection characteristic may be obtained without a substantial increase in driving voltage.

The electron transport region ETR may include a hole blocking layer, which includes 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 4,7-diphenyl- (Bphen). 1,10-phenanthroline), but is not limited thereto.

Meanwhile, the second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 has conductivity. The second electrode EL2 may be formed of a metal alloy or a conductive compound. The second electrode EL2 may be a cathode. The second electrode EL2 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the second electrode EL2 DL is a transmissive electrode, the second electrode EL2 is preferably a transparent metal oxide, preferably indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc (ITZO). oxide) and the like. When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, or a compound or mixture thereof (eg, a mixture of Ag and Mg). Alternatively, a plurality of transparent conductive layers including a reflective or semi-transmissive layer formed of the above-described material and a transparent conductive layer formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. It may have a layer structure. The second electrode EL2 may be connected to the auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

In the organic electroluminescent device, as a voltage is applied to each of the first electrode EL1 and the second electrode EL2 , holes injected from the first electrode EL1 pass through the hole transport region HTR Electrons moved to the emission layer EML and injected from the second electrode EL2 move to the emission layer EML through the electron transport region ETR. Electrons and holes recombine in the light emitting layer (EML) to generate excitons, and the excitons fall from the excited state to the ground state and emit light. When the organic electroluminescent device is a top emission type, the first electrode EL1 may be a reflective electrode, and the second electrode EL2 may be a transmissive electrode or a transflective electrode. When the organic EL device 10 is a bottom emission type, the first electrode EL1 may be a transmissive electrode or a transflective electrode, and the second electrode EL2 may be a reflective electrode.

The organic electroluminescent device may exhibit improved luminous efficiency and lifetime characteristics by using the organic compound of the present invention as a light emitting layer material.

Hereinafter, the present invention will be described in more detail through specific examples and comparative examples. The following examples are only examples to help the understanding of the present invention, and the scope of the present invention is not limited thereto.

[Preparation Example 1]

Synthesis of 2-bromo-N1,N1,N3,N3-tetra(naphthalen-2-yl)dibenzo[b,d]furan-1,3-diamine

2-bromo-1,3-difluorodibenzo[b,d]furan (117.0g, 414mmol), di(naphthalen-2-yl)amine (234.3g, 869.4mmol), Cs2CO3 (364g, 1117.8gmmol) under a nitrogen stream 300ml of DMF was added and stirred at 155°C for 12 hours. When the reaction was completed, 68 g (85%) of the target compound was obtained by recrystallization after completion of the reaction by adding water.

GC-Mass (theoretical: 780.18 g/mol, measured: 781.15 g/mol)

1H-NMR: δ 7.88 (dd, 1H), 7.78 to 7.71 (m, 8H), 7.5 to 7.4 (m, 16H), 7.11 (s, 4H),

[Preparation Example 2]

Synthesis of 7-(2-bromo-1-(7H-dibenzo[c,g]carbazol-7-yl)dibenzo[b,d]furan-3-yl)-7H-dibenzo[b,g]carbazole

23g of the target compound was obtained in the same manner as in [Preparation Example 1] except that 7H-dibenzo[b,g]carbazole was used as a reactant;

GC-Mass (theoretical: 776.15 g/mol, measured: 777.72 g/mol)

[Preparation Example 3]

Synthesis of N-(2-bromo-3-(7H-dibenzo[b,g]carbazol-7-yl)phenyl)-N-(naphthalen-2-yl)naphthalen-2-amine

a-1

2-bromo-1,3-difluorodibenzo[b,d]furan (117.0g, 414mmol), 7H-dibenzo[b,g]carbazole (122.3g, 455mmol), Cs2CO3 (364g, 1117.8gmmol) was added with 300ml of DMF Then, it was heated and refluxed at 155 °C for 12 hours. After completion of the reaction, the mixture was extracted with MC 500 mL, and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 155 g (yield 85%) of the target compound.

GC-Mass (theoretical: 529.05 g/mol, measured: 530.40 g/mol)

1H-NMR: δ 8.54 (dd, 1H), 8.28 (dd, 1H), 8.11 (dd, 1H), 7.99 to 7.94 (m, 4H), 7.75 to 7.51 (m, 6H), 7.40 to 7.31 (m, 3H), 7.20(s, 1H)

a-2

7-(2-bromo-1-fluorodibenzo[b,d]furan-3-yl)-7H-dibenzo[b,g]carbazole (155.0g, 68mmol), Diphenylamine (11.5g, 68mmol), Cs2CO3 under nitrogen stream (59g, 183.6gmmol) was added to 300ml of DMF and stirred at 155°C for 12 hours. When the reaction was completed, 31 g (78%) of the target compound was obtained by recrystallization after completion of the reaction by adding water.

GC-Mass (theoretical: 688.15 g/mol, measured: 689.66 g/mol)

1H-NMR: 8.54 (dd, 1H), 8.28 (dd, 1H), 8.11 (dd, 1H), 7.81 to 7.30 (m, 21H), 7.28 (dd, 1H), 7.11 (s, 2H), 7.03 ( dd, 1H)

[Preparation Example 4]

Synthesis of 7-(2-bromo-1-(7H-dibenzo[c,g]carbazol-7-yl)dibenzo[b,d]furan-3-yl)-7H-dibenzo[b,g]carbazole

21 g of the target compound was obtained in the same manner as in [Preparation Example 3] except that di(naphthalen-2-yl)amine and diphenylamine were used as reactants;

GC-Mass (theoretical: 680.15 g/mol, measured: 681.63 g/mol)

[Preparation Example 5]

Synthesis of 2-bromo-3-(7H-dibenzo[b,g]carbazol-7-yl)-N,N-diphenyldibenzo[b,d]furan-1-amine

26 g of the target compound was obtained in the same manner as in [Preparation Example 3] except that 7H-dibenzo[b,g]carbazole and diphenylamine were used as reactants;

GC-Mass (theoretical: 678.13 g/mol, measured: 679.62 g/mol)

[Preparation Example 6]

Synthesis of 2-bromo-1-(9H-carbazol-9-yl)-N,N-di(naphthalen-2-yl)dibenzo[b,d]furan-3-amine

24 g of the target compound was obtained in the same manner as in [Preparation Example 4] except that 9H-carbazole was used as a reactant;

GC-Mass (theoretical: 678.13 g/mol, measured: 679.62 g/mol)

[Preparation Example 7]

Synthesis of 7-(2-bromo-1-(9H-carbazol-9-yl)dibenzo[b,d]furan-3-yl)-7H-dibenzo[b,g]carbazole

24 g of the target compound was obtained in the same manner as in [Preparation Example 5] except that 9H-carbazole was used as a reactant;

GC-Mass (theoretical: 676.12 g/mol, measured: 677.60 g/mol)

[Preparation Example 8]

Synthesis of 2-bromo-N1,N1-bis(4-(tert-butyl)phenyl)-N3,N3-di(naphthalen-2-yl)dibenzo[b,d]furan-1,3-diamine

22 g of the target compound was obtained in the same manner as in [Preparation Example 4] except that bis(4-(tert-butyl)phenyl)amine was used as a reactant;

GC-Mass (theoretical: 792.27 g/mol, measured: 793.85 g/mol)

[Preparation Example 9]

Synthesis of 2-bromo-N,N-bis(4-(tert-butyl)phenyl)-3-(7H-dibenzo[b,g]carbazol-7-yl)dibenzo[b,d]furan-1-amine

20 g of the target compound was obtained in the same manner as in [Preparation Example 5] except that bis(4-(tert-butyl)phenyl)amine was used as a reactant;

GC-Mass (theoretical: 790.26 g/mol, measured: 791.83 g/mol)

[Preparation example 10]

2-bromo-1-(3,6-di-tert-butyl-9H-carbazol-9-yl)-N,N-di(naphthalen-2-yl)dibenzo[b,d]furan-3-amine synthesis

22 g of the target compound was obtained in the same manner as in [Preparation Example 4] except that 3,6-di-tert-butyl-9H-carbazole was used as a reactant;

GC-Mass (theoretical: 790.26 g/mol, measured: 791.83 g/mol)

[Preparation Example 11]

7-(2-bromo-1-(3,6-di-tert-butyl-9H-carbazol-9-yl)dibenzo[b,d]furan-3-yl)-7H-dibenzo[b,g]carbazole synthesis of

20 g of the target compound was obtained in the same manner as in [Preparation Example 5] except that 3,6-di-tert-butyl-9H-carbazole was used as a reactant;

GC-Mass (theoretical: 788.24 g/mol, measured: 789.82 g/mol)

[Preparation Example 12]

of N1,N1-di([1,1'-biphenyl]-4-yl)-2-bromo-N3,N3-di(naphthalen-2-yl)dibenzo[b,d]furan-1,3-diamine synthesis

25 g of the target compound was obtained in the same manner as in [Preparation Example 4] except that di([1,1'-biphenyl]-4-yl)amine was used as a reactant;

GC-Mass (theoretical: 732.21 g/mol, measured: 733.83 g/mol)

[Preparation Example 13]

N,N-di([1,1'-biphenyl]-4-yl)-2-bromo-3-(7H-dibenzo[b,g]carbazol-7-yl)dibenzo[b,d]furan-1 -amine synthesis

23 g of the target compound was obtained in the same manner as in [Preparation Example 5] except that di([1,1'-biphenyl]-4-yl)amine was used as a reactant;

GC-Mass (theoretical: 830.19 g/mol, measured: 731.81 g/mol)

[Preparation Example 14]

Synthesis of 2-bromo-1-(3,6-diphenyl-9H-carbazol-9-yl)-N,N-di(naphthalen-2-yl)dibenzo[b,d]furan-3-amine

21 g of the target compound was obtained in the same manner as in [Preparation Example 4] except that 3,6-diphenyl-9H-carbazole was used as a reactant;

GC-Mass (theoretical: 830.19 g/mol, measured: 831.81 g/mol)

[Preparation Example 15]

Synthesis of 7-(2-bromo-1-(3,6-diphenyl-9H-carbazol-9-yl)dibenzo[b,d]furan-3-yl)-7H-dibenzo[b,g]carbazole

25 g of the target compound was obtained in the same manner as in [Preparation Example 5] except that 3,6-diphenyl-9H-carbazole was used as a reactant;

GC-Mass (theoretical: 828.18 g/mol, measured: 829.80 g/mol)

[Preparation Example 16]

Synthesis of 2-bromo-N3,N3-di(naphthalen-2-yl)-N1,N1-bis(4-(trifluoromethyl)phenyl)dibenzo[b,d]furan-1,3-diamine

26 g of the target compound was obtained in the same manner as in [Preparation Example 4] except that bis(4-(trifluoromethyl)phenyl)amine was used as a reactant;

GC-Mass (theoretical: 816.12 g/mol, measured: 817.63 g/mol)

[Preparation Example 17]

Synthesis of 2-bromo-3-(7H-dibenzo[b,g]carbazol-7-yl)-N,N-bis(4-(trifluoromethyl)phenyl)dibenzo[b,d]furan-1-amine

22 g of the target compound was obtained in the same manner as in [Preparation Example 5] except that bis(4-(trifluoromethyl)phenyl)amine was used as a reactant;

GC-Mass (theoretical: 814.11 g/mol, measured: 815.61 g/mol)

[Preparation Example 18]

Synthesis of 1-(3,6-bis(trifluoromethyl)-9H-carbazol-9-yl)-2-bromo-N,N-di(naphthalen-2-yl)dibenzo[b,d]furan-3-amine

23 g of the target compound was obtained in the same manner as in [Preparation Example 4] except that 3,6-bis(trifluoromethyl)-9H-carbazole was used as a reactant;

GC-Mass (theoretical: 814.11 g/mol, measured: 815.61 g/mol)

[Preparation Example 19]

Synthesis of 7-(1-(3,6-bis(trifluoromethyl)-9H-carbazol-9-yl)-2-bromodibenzo[b,d]furan-3-yl)-7H-dibenzo[b,g]carbazole

21 g of the target compound was obtained in the same manner as in [Preparation Example 5] except that 3,6-bis(trifluoromethyl)-9H-carbazole was used as a reactant;

GC-Mass (theoretical: 812.09 g/mol, measured: 813.60 g/mol)

[Preparation Example 20]

Synthesis of 2-bromo-N1,N1,N3,N3-tetra(isoquinolin-6-yl)dibenzo[b,d]furan-1,3-diamine

16 g of the target compound was obtained in the same manner as in [Preparation Example 1] except that di(isoquinolin-6-yl)amine was used as a reactant;

GC-Mass (theoretical: 784.16 g/mol, measured: 785.71 g/mol)

[Preparation Example 21]

Synthesis of 2-bromo-N3,N3-di(isoquinolin-6-yl)-N1,N1-di(naphthalen-2-yl)dibenzo[b,d]furan-1,3-diamine

20 g of the target compound was obtained in the same manner as in [Preparation Example 3] except that di(isoquinolin-6-yl)amine and di(naphthalen-2-yl)amine were used as reactants;

GC-Mass (theoretical: 782.17 g/mol, measured: 783.73 g/mol)

[Preparation Example 22]

N-(2-bromo-1-(7H-dibenzo[c,g]carbazol-7-yl)dibenzo[b,d]furan-3-yl)-N-(isoquinolin-6-yl)isoquinolin-6- Synthesis of amines

21 g of the target compound was obtained in the same manner as in [Preparation Example 3] except that di(isoquinolin-6-yl)amine and 7H-dibenzo[b,g]carbazole were used as reactants;

GC-Mass (theoretical: 780.15 g/mol, measured: 781.71 g/mol)

[Preparation Example 23]

Synthesis of 2-bromo-N3,N3-di(isoquinolin-6-yl)-N1,N1-di(naphthalen-2-yl)dibenzo[b,d]furan-1,3-diamine

20 g of the target compound was obtained in the same manner as in [Preparation Example 3] except that di(isoquinolin-6-yl)amine and diphenylamine were used as reactants;

GC-Mass (theoretical: 682.14 g/mol, measured: 683.61 g/mol)

[Preparation Example 24]

N-(2-bromo-1-(7H-dibenzo[c,g]carbazol-7-yl)dibenzo[b,d]furan-3-yl)-N-(isoquinolin-6-yl)isoquinolin-6- Synthesis of amines

21 g of the target compound was obtained in the same manner as in [Preparation Example 3] except that di(isoquinolin-6-yl)amine and 9H-carbazole were used as reactants;

GC-Mass (theoretical: 680.12 g/mol, measured: 681.59 g/mol)

[Preparation Example 25]

Synthesis of 2-bromo-N1,N1-bis(4-(tert-butyl)phenyl)-N3,N3-di(isoquinolin-6-yl)dibenzo[b,d]furan-1,3-diamine

20 g of the target compound was obtained in the same manner as in [Preparation Example 3] except that di(isoquinolin-6-yl)amine and bis(4-(tert-butyl)phenyl)amine were used as reactants;

GC-Mass (theoretical: 794.26 g/mol, measured: 795.83 g/mol)

[Preparation Example 26]

N-(2-bromo-1-(3,6-di-tert-butyl-9H-carbazol-9-yl)dibenzo[b,d]furan-3-yl)-N-(isoquinolin-6-yl) Synthesis of isoquinolin-6-amine

23 g of the target compound was obtained in the same manner as in [Preparation Example 3] except that di(isoquinolin-6-yl)amine and 3,6-di-tert-butyl-9H-carbazole were used as reactants;

GC-Mass (theoretical: 792.25 g/mol, measured: 793.81 g/mol)

[Preparation example 27]

of N1,N1-di([1,1'-biphenyl]-4-yl)-2-bromo-N3,N3-di(isoquinolin-6-yl)dibenzo[b,d]furan-1,3-diamine synthesis

27 g of the target compound was obtained in the same manner as in [Preparation Example 3] except that di(isoquinolin-6-yl)amine and di([1,1'-biphenyl]-4-yl)amine were used as reactants. .;

GC-Mass (theoretical: 834.20 g/mol, measured: 835.81 g/mol)

[Preparation Example 28]

N-(2-bromo-1-(3,6-diphenyl-9H-carbazol-9-yl)dibenzo[b,d]furan-3-yl)-N-(isoquinolin-6-yl)isoquinolin-6- Synthesis of amines

22 g of the target compound was obtained in the same manner as in [Preparation Example 3] except that di(isoquinolin-6-yl)amine and 3,6-diphenyl-9H-carbazole were used as reactants;

GC-Mass (theoretical: 832.18 g/mol, measured: 833.79 g/mol)

[Preparation Example 29]

of N1,N1-di([1,1'-biphenyl]-4-yl)-2-bromo-N3,N3-di(naphthalen-2-yl)dibenzo[b,d]thiophene-1,3-diamine synthesis

22 g of the target compound was obtained in the same manner as in [Preparation Example 1] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 848.19 g/mol, measured: 849.89 g/mol)

[Preparation example 30]

Synthesis of 7,7'-(2-bromodibenzo[b,d]thiophene-1,3-diyl)bis(7H-dibenzo[b,g]carbazole)

23 g of the target compound was obtained in the same manner as in [Preparation Example 2] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 792.12 g/mol, measured: 783.78 g/mol)

[Preparation Example 31]

Synthesis of 2-bromo-3-(7H-dibenzo[b,g]carbazol-7-yl)-N,N-di(naphthalen-2-yl)dibenzo[b,d]thiophen-1-amine

22 g of the target compound was obtained in the same manner as in [Preparation Example 3] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 794.14 g/mol, measured: 795.80 g/mol)

[Preparation example 32]

Synthesis of 2-bromo-N3,N3-di(naphthalen-2-yl)-N1,N1-diphenyldibenzo[b,d]thiophene-1,3-diamine

21 g of the target compound was obtained in the same manner as in [Preparation Example 4] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 696.16 g/mol, measured: 697.69 g/mol)

[Preparation Example 33]

Synthesis of 2-bromo-3-(7H-dibenzo[b,g]carbazol-7-yl)-N,N-diphenyldibenzo[b,d]thiophen-1-amine

26 g of the target compound was obtained in the same manner as in [Preparation Example 5] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 694.11 g/mol, measured: 695.68 g/mol)

[Preparation Example 34]

Synthesis of 2-bromo-1-(9H-carbazol-9-yl)-N,N-di(naphthalen-2-yl)dibenzo[b,d]thiophen-3-amine

24 g of the target compound was obtained in the same manner as in [Preparation Example 6] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 694.11 g/mol, measured: 695.68 g/mol)

[Preparation Example 35]

Synthesis of 7-(2-bromo-1-(9H-carbazol-9-yl)dibenzo[b,d]thiophen-3-yl)-7H-dibenzo[b,g]carbazole

24 g of the target compound was obtained in the same manner as in [Preparation Example 7] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 692.09 g/mol, measured: 693.66 g/mol)

[Preparation Example 36]

Synthesis of 2-bromo-N1,N1-bis(4-(tert-butyl)phenyl)-N3,N3-di(naphthalen-2-yl)dibenzo[b,d]thiophene-1,3-diamine

22 g of the target compound was obtained in the same manner as in [Preparation Example 8] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 808.25 g/mol, measured: 809.91 g/mol)

[Preparation Example 37]

Synthesis of 2-bromo-N,N-bis(4-(tert-butyl)phenyl)-3-(7H-dibenzo[b,g]carbazol-7-yl)dibenzo[b,d]thiophen-1-amine

20 g of the target compound was obtained in the same manner as in [Preparation Example 9] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 806.23 g/mol, measured: 807.89 g/mol)

[Preparation Example 38]

2-bromo-1-(3,6-di-tert-butyl-9H-carbazol-9-yl)-N,N-di(naphthalen-2-yl)dibenzo[b,d]thiophen-3-amine synthesis

22 g of the target compound was obtained in the same manner as in [Preparation Example 10] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 806.23 g/mol, measured: 807.89 g/mol)

[Preparation Example 39]

7-(2-bromo-1-(3,6-di-tert-butyl-9H-carbazol-9-yl)dibenzo[b,d]thiophen-3-yl)-7H-dibenzo[b,g]carbazole synthesis of

20 g of the target compound was obtained in the same manner as in [Preparation Example 11] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 804.22 g/mol, measured: 805.88 g/mol)

[Preparation Example 40]

of N1,N1-di([1,1'-biphenyl]-4-yl)-2-bromo-N3,N3-di(naphthalen-2-yl)dibenzo[b,d]thiophene-1,3-diamine synthesis

25 g of the target compound was obtained in the same manner as in [Preparation Example 12] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 848.19 g/mol, measured: 849.89 g/mol)

[Preparation Example 41]

N,N-di([1,1'-biphenyl]-4-yl)-2-bromo-3-(7H-dibenzo[b,g]carbazol-7-yl)dibenzo[b,d]thiophen-1 -amine synthesis

23 g of the target compound was obtained in the same manner as in [Preparation Example 13] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 846.17 g/mol, measured: 747.87 g/mol)

[Preparation Example 42]

Synthesis of 2-bromo-1-(3,6-diphenyl-9H-carbazol-9-yl)-N,N-di(naphthalen-2-yl)dibenzo[b,d]thiophen-3-amine

21 g of the target compound was obtained in the same manner as in [Preparation Example 14] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 846.17 g/mol, measured: 747.87 g/mol)

[Preparation Example 43]

Synthesis of 7-(2-bromo-1-(3,6-diphenyl-9H-carbazol-9-yl)dibenzo[b,d]thiophen-3-yl)-7H-dibenzo[b,g]carbazole

25 g of the target compound was obtained in the same manner as in [Preparation Example 15] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 844.15 g/mol, measured: 845.86 g/mol)

[Preparation Example 44]

Synthesis of 2-bromo-N3,N3-di(naphthalen-2-yl)-N1,N1-bis(4-(trifluoromethyl)phenyl)dibenzo[b,d]thiophene-1,3-diamine

26 g of the target compound was obtained in the same manner as in [Preparation Example 16] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 832.10 g/mol, measured: 833.69 g/mol)

[Preparation Example 45]

Synthesis of 2-bromo-3-(7H-dibenzo[b,g]carbazol-7-yl)-N,N-bis(4-(trifluoromethyl)phenyl)dibenzo[b,d]thiophen-1-amine

22 g of the target compound was obtained in the same manner as in [Preparation Example 17] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 830.08 g/mol, measured: 831.67 g/mol)

[Preparation Example 46]

Synthesis of 1-(3,6-bis(trifluoromethyl)-9H-carbazol-9-yl)-2-bromo-N,N-di(naphthalen-2-yl)dibenzo[b,d]thiophen-3-amine

23 g of the target compound was obtained in the same manner as in [Preparation Example 18] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 830.08 g/mol, measured: 831.67 g/mol)

[Preparation Example 47]

Synthesis of 7-(1-(3,6-bis(trifluoromethyl)-9H-carbazol-9-yl)-2-bromodibenzo[b,d]thiophen-3-yl)-7H-dibenzo[b,g]carbazole

21 g of the target compound was obtained in the same manner as in [Preparation Example 19] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 828.07 g/mol, measured: 829.66 g/mol)

[Preparation example 48]

Synthesis of 2-bromo-N1,N1,N3,N3-tetra(isoquinolin-6-yl)dibenzo[b,d]thiophene-1,3-diamine

16 g of the target compound was obtained in the same manner as in [Preparation Example 20] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 800.14 g/mol, measured: 801.77 g/mol)

[Preparation Example 49]

Synthesis of 2-bromo-N3,N3-di(isoquinolin-6-yl)-N1,N1-di(naphthalen-2-yl)dibenzo[b,d]thiophene-1,3-diamine

20 g of the target compound was obtained in the same manner as in [Preparation Example 21] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 798.15 g/mol, measured: 799.79 g/mol)

[Preparation example 50]

N-(2-bromo-1-(7H-dibenzo[b,g]carbazol-7-yl)dibenzo[b,d]thiophen-3-yl)-N-(isoquinolin-6-yl)isoquinolin-6- Synthesis of amines

21 g of the target compound was obtained in the same manner as in [Preparation Example 22] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 796.13 g/mol, measured: 797.77 g/mol)

[Preparation Example 51]

Synthesis of 2-bromo-N3,N3-di(isoquinolin-6-yl)-N1,N1-diphenyldibenzo[b,d]thiophene-1,3-diamine

20 g of the target compound was obtained in the same manner as in [Preparation Example 23] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 698.11 g/mol, measured: 699.67 g/mol)

[Preparation example 52]

Synthesis of N-(2-bromo-1-(9H-carbazol-9-yl)dibenzo[b,d]thiophen-3-yl)-N-(isoquinolin-6-yl)isoquinolin-6-amine

21 g of the target compound was obtained in the same manner as in [Preparation Example 24], except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 696.10 g/mol, measured: 697.65 g/mol)

[Preparation Example 53]

Synthesis of 2-bromo-N1,N1-bis(4-(tert-butyl)phenyl)-N3,N3-di(isoquinolin-6-yl)dibenzo[b,d]thiophene-1,3-diamine

20 g of the target compound was obtained in the same manner as in [Preparation Example 25] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 810.24 g/mol, measured: 811.89 g/mol)

[Preparation Example 54]

N-(2-bromo-1-(3,6-di-tert-butyl-9H-carbazol-9-yl)dibenzo[b,d]thiophen-3-yl)-N-(isoquinolin-6-yl) Synthesis of isoquinolin-6-amine

23 g of the target compound was obtained in the same manner as in [Preparation Example 26] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 808.22 g/mol, measured: 809.87 g/mol)

[Preparation Example 55]

of N1,N1-di([1,1'-biphenyl]-4-yl)-2-bromo-N3,N3-di(isoquinolin-6-yl)dibenzo[b,d]thiophene-1,3-diamine synthesis

27 g of the target compound was obtained in the same manner as in [Preparation Example 27] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 850.18 g/mol, measured: 851.87 g/mol)

[Preparation Example 56]

N-(2-bromo-1-(3,6-diphenyl-9H-carbazol-9-yl)dibenzo[b,d]thiophen-3-yl)-N-(isoquinolin-6-yl)isoquinolin-6- Synthesis of amines

22 g of the target compound was obtained in the same manner as in [Preparation Example 28] except that 2-bromo-1,3-difluorodibenzo[b,d]thiophene was used as a reactant;

GC-Mass (theoretical: 848.16 g/mol, measured: 849.85 g/mol)

[Synthesis Example 1] Synthesis of Mat 1

에서 2시간 가열환류 하였다. 반응온도를 -40℃로 낮춘 후 Boron tribromide 10.8g(43.35mmol)을 천천히 첨가한 후 반응온도를 상온으로 천천히 올린다. 상온에서 30분 교반 후 온도를 0℃로 낮춘다. 0℃에서 N,N-Diisopropylethylamine 69g(68mmol)을 천천히 적가한 후 온도를 상온으로 올린다. 추가로 120℃에서 5시간 가열환류 한 후 온도를 상온으로 낮추고 sodium acetate dichloromethane용액으로 반응을 종결한다. 혼합액을 M.C 500 mL로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO₄로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 4.9g(수율 55%)을 얻었다. 1H-NMR: 7.98(dd, 1H), 7.79~7.71 (m, 9H), 7.54~7.39(m, 17H), 7.11(s, 4H)[Preparation Example 1] A mixed solution of 11.29 g (14.45 mmol) and 250 mL of tert-butylbenzene was slowly added to a tert-butyllithium pentane solution (25.5 ml, 1.7M, 43.35 mmol) cooled to 0° C. under a nitrogen stream. 60 after adding the solution

It was heated and refluxed for 2 hours. After lowering the reaction temperature to -40°C, 10.8 g (43.35 mmol) of boron tribromide was slowly added thereto, and then the reaction temperature was slowly raised to room temperature. After stirring at room temperature for 30 minutes, lower the temperature to 0°C. At 0°C, 69 g (68 mmol) of N,N-Diisopropylethylamine was slowly added dropwise, and then the temperature was raised to room temperature. Further, after heating and refluxing at 120°C for 5 hours, the temperature was lowered to room temperature and the reaction was terminated with sodium acetate dichloromethane solution. The mixture was extracted with MC 500 mL, and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 4.9 g (yield 55%) of the target compound. 1H-NMR: 7.98 (dd, 1H), 7.79 to 7.71 (m, 9H), 7.54 to 7.39 (m, 17H), 7.11 (s, 4H)

[Synthesis Example 2] Synthesis of Mat 2

[Preparation Example 2] A mixed solution of 11.29 g (12.8 mmol) and 250 mL of tert-butylbenzene was slowly added to a tert-butyllithium pentane solution (25.5 ml, 1.7M, 43.35 mmol) cooled to 0° C. under a nitrogen stream. After the solution was added, it was heated and refluxed at 60 °C for 2 hours. After lowering the reaction temperature to -40°C, 10.8 g (43.35 mmol) of boron tribromide was slowly added thereto, and then the reaction temperature was slowly raised to room temperature. After stirring at room temperature for 30 minutes, lower the temperature to 0°C. At 0°C, 69 g (68 mmol) of N,N-Diisopropylethylamine was slowly added dropwise, and then the temperature was raised to room temperature. Further, after heating and refluxing at 120°C for 5 hours, the temperature was lowered to room temperature and the reaction was terminated with sodium acetate dichloromethane solution. The mixture was extracted with MC 500 mL, and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 4.9 g (yield 54%) of the target compound. 1H-NMR: 7.98 (dd, 1H), 7.79 to 7.71 (m, 9H), 7.54 to 7.39 (m, 17H), 7.11 (s, 4H)

[Synthesis Example 3] Synthesis of Mat 3

1 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 3] was used as a reactant; HRMS [M]+: 708.63

[Synthesis Example 4] Synthesis of Mat 4

1.3 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 4] was used as a reactant; HRMS [M]+: 610.52

[Synthesis Example 5] Synthesis of Mat 5

1.1 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 5] was used as a reactant; HRMS [M]+: 608.51

[Synthesis Example 6] Synthesis of Mat 6

0.8 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 6] was used as a reactant; HRMS [M]+: 608.61

[Synthesis Example 7] Synthesis of Mat 7

0.5 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 7] was used as a reactant; HRMS [M]+: 606.49

[Synthesis Example 8] Synthesis of Mat 8

0.4 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 8] was used as a reactant; HRMS [M]+: 722.74

[Synthesis Example 9] Synthesis of Mat 9

0.35 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 9] was used as a reactant; HRMS [M]+: 720.72

[Synthesis Example 10] Synthesis of Mat 10

0.6 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 10] was used as a reactant; HRMS [M]+: 720.72

[Synthesis Example 11] Synthesis of Mat 11

0.8 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 11] was used as a reactant; HR1MS [M]+: 718.21

[Synthesis Example 12] Synthesis of Mat 12

0.32 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 12] was used as a reactant; HRMS [M]+: 762.72

[Synthesis Example 13] Synthesis of Mat 13

0.40 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 13] was used as a reactant; HRMS [M]+: 760.70

[Synthesis Example 14] Synthesis of Mat 14

0.51 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 14] was used as a reactant; HRMS [M]+: 760.70

[Synthesis Example 15] Synthesis of Mat 15

0.22 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 15] was used as a reactant; HRMS [M]+: 758.69

[Synthesis Example 16] Synthesis of Mat 16

0.47 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 16] was used as a reactant; HRMS [M]+: 746.52

[Synthesis Example 17] Synthesis of Mat 17

0.25 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 17] was used as a reactant; HRMS [M]+: 744.50

[Synthesis Example 18] Synthesis of Mat 18

0.33 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 18] was used as a reactant; HRMS [M]+: 744.50

[Synthesis Example 19] Synthesis of Mat 19

0.59 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 19] was used as a reactant; HRMS [M]+: 742.49

[Synthesis Example 20] Synthesis of Mat 20

0.47 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 20] was used as a reactant; HRMS [M]+: 714.60

[Synthesis Example 21] Synthesis of Mat 21

0.28 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 21] was used as a reactant; HRMS [M]+: 712.62

[Synthesis Example 22] Synthesis of Mat 22

0.22 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 22] was used as a reactant; HRMS [M]+: 710.60

[Synthesis Example 23] Synthesis of Mat 23

0.29 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 23] was used as a reactant; HRMS [M]+: 612.50

[Synthesis Example 24] Synthesis of Mat 24

0.17 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 24] was used as a reactant; HRMS [M]+: 610.48

[Synthesis Example 25] Synthesis of Mat 25

0.31 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 25] was used as a reactant; HRMS [M]+: 724.72

[Synthesis Example 26] Synthesis of Mat 26

0.44 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 26] was used as a reactant; HRMS [M]+: 722.70

[Synthesis Example 27] Synthesis of Mat 27

0.58 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 27] was used as a reactant; HRMS [M]+: 764.70

[Synthesis Example 28] Synthesis of Mat 28

0.49 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 28] was used as a reactant; HRMS [M]+: 762.68

[Synthesis Example 29] Synthesis of Mat 29

[Preparation Example 29] A mixed solution of 11.29 g (12.8 mmol) and 250 mL of tert-butylbenzene was slowly added to a tert-butyllithium pentane solution (25.5ml, 1.7M, 43.35mmol) cooled to 0°C under a nitrogen stream. After the solution was added, it was heated and refluxed at 60 °C for 2 hours. After lowering the reaction temperature to -40°C, 10.8 g (43.35 mmol) of boron tribromide was slowly added thereto, and then the reaction temperature was slowly raised to room temperature. After stirring at room temperature for 30 minutes, lower the temperature to 0°C. At 0°C, 69 g (68 mmol) of N,N-Diisopropylethylamine was slowly added dropwise, and then the temperature was raised to room temperature. Further, after heating and refluxing at 120°C for 5 hours, the temperature was lowered to room temperature and the reaction was terminated with sodium acetate dichloromethane solution. The mixture was extracted with MC 500 mL, and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 4.9 g (yield 54%) of the target compound. 1H-NMR: 7.98 (dd, 1H), 7.79 to 7.71 (m, 9H), 7.54 to 7.39 (m, 17H), 7.11 (s, 4H)

[Synthesis Example 30] Synthesis of Mat 30

[Preparation Example 30] 11.29g (12.8mmol) and 250 mL of tert-butylbenzene mixed solution was slowly added to a tert-butyllithium pentane solution (25.5ml, 1.7M, 43.35mmol) cooled to 0°C under a nitrogen stream. After the solution was added, it was heated and refluxed at 60 °C for 2 hours. After lowering the reaction temperature to -40°C, 10.8 g (43.35 mmol) of boron tribromide was slowly added thereto, and then the reaction temperature was slowly raised to room temperature. After stirring at room temperature for 30 minutes, lower the temperature to 0°C. At 0°C, 69 g (68 mmol) of N,N-Diisopropylethylamine was slowly added dropwise, and then the temperature was raised to room temperature. Further, after heating and refluxing at 120°C for 5 hours, the temperature was lowered to room temperature and the reaction was terminated with sodium acetate dichloromethane solution. The mixture was extracted with MC 500 mL, and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 4.9 g (yield 54%) of the target compound. 1H-NMR: 7.98 (dd, 1H), 7.79 to 7.71 (m, 9H), 7.54 to 7.39 (m, 17H), 7.11 (s, 4H)

[Synthesis Example 31] Synthesis of Mat 31

0.31 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 31] was used as a reactant; HRMS [M]+: 724.69

[Synthesis Example 32] Synthesis of Mat 32

0.50 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 32] was used as a reactant; HRMS [M]+: 626.58

[Synthesis Example 33] Synthesis of Mat 33

0.41 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 33] was used as a reactant; HRMS [M]+: 624.57

[Synthesis Example 34] Synthesis of Mat 34

0.38 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 34] was used as a reactant; HRMS [M]+: 624.57

[Synthesis Example 35] Synthesis of Mat 35

0.26 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 35] was used as a reactant; HRMS [M]+: 622.55

[Synthesis Example 36] Synthesis of Mat 36

0.37 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 36] was used as a reactant; HRMS [M]+: 738.80

[Synthesis Example 37] Synthesis of Mat 37

0.44 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 37] was used as a reactant; HRMS [M]+: 736.78

[Synthesis Example 38] Synthesis of Mat 38

0.36 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 38] was used as a reactant; HRMS [M]+: 736.78

[Synthesis Example 39] Synthesis of Mat 39

0.7 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 39] was used as a reactant; HRMS [M]+: 734.77

[Synthesis Example 40] Synthesis of Mat 40

0.52 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 40] was used as a reactant; HRMS [M]+: 778.78

[Synthesis Example 41] Synthesis of Mat 41

0.41 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 41] was used as a reactant; HRMS [M]+: 776.76

[Synthesis Example 42] Synthesis of Mat 42

0.41 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 42] was used as a reactant; HRMS [M]+: 776.76

[Synthesis Example 43] Synthesis of Mat 43

0.35 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 43] was used as a reactant; HRMS [M]+: 774.75

[Synthesis Example 44] Synthesis of Mat 44

0.28 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 44] was used as a reactant; HRMS [M]+: 762.58

[Synthesis Example 45] Synthesis of Mat 45

0.41 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 45] was used as a reactant; HRMS [M]+: 760.56

[Synthesis Example 46] Synthesis of Mat 46

0.23 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 46] was used as a reactant; HRMS [M]+: 760.56

[Synthesis Example 47] Synthesis of Mat 47

0.18 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 47] was used as a reactant; HRMS [M]+: 758.55

[Synthesis Example 48] Synthesis of Mat 48

[Preparation Example 48] A mixed solution of 11.29 g (12.8 mmol) and 250 mL of tert-butylbenzene was slowly added to a tert-butyllithium pentane solution (25.5 ml, 1.7 M, 43.35 mmol) cooled to 0° C. under a nitrogen stream. After the solution was added, it was heated and refluxed at 60 °C for 2 hours. After lowering the reaction temperature to -40°C, 10.8 g (43.35 mmol) of boron tribromide was slowly added thereto, and then the reaction temperature was slowly raised to room temperature. After stirring at room temperature for 30 minutes, lower the temperature to 0°C. At 0°C, 69 g (68 mmol) of N,N-Diisopropylethylamine was slowly added dropwise, and then the temperature was raised to room temperature. Further, after heating and refluxing at 120°C for 5 hours, the temperature was lowered to room temperature and the reaction was terminated with sodium acetate dichloromethane solution. The mixture was extracted with MC 500 mL, and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 4.9 g (yield 54%) of the target compound. 1H-NMR: 9.02 (s, 4H), 8.65 (dd, 1H), 8.25 (dd, 4H), 7.93 (dd, 1H), 7.79 to 7.71 (m, 13H), 5.83 to 5.73 (m, 4H)

[Synthesis Example 49] Synthesis of Mat 49

0.54 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 49] was used as a reactant; HRMS [M]+: 728.68

[Synthesis Example 50] Synthesis of Mat 50

0.62 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 50] was used as a reactant; HRMS [M]+: 726.66

[Synthesis Example 51] Synthesis of Mat 51

0.23 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 51] was used as a reactant; HRMS [M]+: 628.56

[Synthesis Example 52] Synthesis of Mat 52

0.15 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 52] was used as a reactant; HRMS [M]+: 626.54

[Synthesis Example 53] Synthesis of Mat 53

0.21 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 53] was used as a reactant; HRMS [M]+: 740.78

[Synthesis Example 54] Synthesis of Mat 54

0.31 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 54] was used as a reactant; HRMS [M]+: 738.76

[Synthesis Example 55] Synthesis of Mat 55

0.17 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 55] was used as a reactant; HRMS [M]+: 780.76

[Synthesis Example 56] Synthesis of Mat 56

0.22 g of the target compound was obtained in the same manner as in [Synthesis Example 1] except that [Preparation Example 56] was used as a reactant; HRMS [M]+: 778.74

[Examples 1 to 11] Preparation of green organic EL device

After high-purity sublimation purification of the compound synthesized in the above synthesis example by a commonly known method, a green organic EL device was manufactured according to the following procedure.

First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing with distilled water, it is ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, ethanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech). The substrate was transferred to

A hole injection layer was formed with a thickness of 80 nm DS-205 (Doosan) on the prepared ITO transparent electrode, and a-NPB (N,N`-Di(1-naphthyl)-N,N`-diphenyl) on the hole transport layer. -(1,1′-biphenyl)-4,4′-diamine) was vacuum deposited to a thickness of 30 nm to form a hole transport layer.

On it, the compounds prepared in Synthesis Examples 1 to 56 as a green dopant material and DS-H522 and DS-TD-002 as green light-emitting host materials were applied as common hosts to form a light-emitting layer with a thickness of 30 nm. At this time, the doping ratio of the light emitting layer (DS-H522:DS-TD-002:Synthesis Example 1-56 = 75%:20%:5%) was collectively applied.

An electron transport layer was formed on the light emitting layer by using an electron transport material, TPBi(2,2`,2``-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole)) to a thickness of 30 nm. did Then, an electron injection layer was formed using LiF with a thickness of 1 nm, and Al 200 nm was formed as a cathode to fabricate a device.

[Comparative example]

An organic electroluminescent device was fabricated in the same manner as in the device fabrication example except for using Alq3, C-545T, and Comparative Example 1, which are representative of green light-emitting materials, and the evaluation results of the fabricated devices are shown in Table 1 did

[Example of evaluation]

For each organic EL device manufactured in Examples 1 to 11 and Comparative Examples 1, 2, and 3, the driving voltage, current efficiency, and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below. indicated.

Sample green dopant drive voltage EL peak current efficiency (V) (nm) (cd/A) Example 1 Mat4 5.22 535 23.1 Example 2 Mat5 5.01 536 25.1 Example 3 Mat7 5.18 538 21.4 Example 4 Mat11 5.06 531 26.7 Example 5 Mat16 5.88 538 23.1 Example 6 Mat17 5.19 531 25.1 Example 7 Mat23 5.22 537 21.4 Example 8 Mat24 5.01 535 26.7 Example 9 Mat32 5.18 535 26.9 Example 10 Mat35 5.06 536 14.9 Example 11 Mat45 5.19 538 23.1 Comparative Example 1 Comparative Example 1 6.52 531 14.9 Comparative Example 2 C-545T 5.90 537 15.5 Comparative Example 3 Alq3 6.14 525 12.8

From Table 1, in the case of the organic light-emitting devices manufactured in Examples 1 to 11, the driving voltage, the emission peak, and the current efficiency were obtained in Comparative Examples 1, 2, and 3, respectively, due to the rigid chemical structure and the structure advantageous to the formation of excitons in the emission layer. It can be confirmed that it is superior to the driving voltage, emission peak, and current efficiency of the manufactured organic light emitting device.

[Examples 12 to 30] Preparation of red organic EL device

After high-purity sublimation purification of the compound synthesized in the above synthesis example by a commonly known method, a red organic EL device was manufactured according to the following procedure.

First, a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing with distilled water, it is ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, ethanol, etc., dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech). The substrate was transferred to

A hole injection layer was formed with a thickness of 80 nm DS-205 (Doosan) on the prepared ITO transparent electrode, and a-NPB (N,N`-Di(1-naphthyl)-N,N`-diphenyl) on the hole transport layer. -(1,1′-biphenyl)-4,4′-diamine) was vacuum deposited to a thickness of 30 nm to form a hole transport layer.

On it, the compounds prepared in Synthesis Examples 1 to 56 as a red dopant material and DS-H522 and DS-TD-018 as a red light-emitting host material were applied as a common host to form a light-emitting layer with a thickness of 30 nm. At this time, the doping ratio of the light emitting layer (DS-H522:DS-TD-018:Synthesis Example 1-56 = 75%:20%:5%) was collectively applied.

On the light emitting layer, TPBi(2,2`,2``-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole)), which is an electron transporting material, was applied to a thickness of 30 nm to form an electron transport layer. did Then, an electron injection layer was formed using LiF to a thickness of 1 nm, and Al 200 nm was formed as a cathode to fabricate a device.

[Comparative example]

An organic electroluminescent device was manufactured in the same manner as in the device fabrication example except for using DCM2, DCJTB, and DCDDC, which are representative of red light emitting materials, and the evaluation results of the manufactured devices are shown in Table 2.

[Example of evaluation]

For each organic EL device manufactured in Examples 12 to 30 and Comparative Examples 3, 4, and 5, the driving voltage, current efficiency, and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 2 below. indicated.

Sample red dopant drive voltage EL peak current efficiency (V) (nm) (cd/A) Example 19 Mat 1 5.81 620 23.8 Example 20 Mat 2 5.97 618 20.8 Example 21 Mat 3 5.93 619 23.2 Example 22 Mat 8 5.81 620 22.5 Example 23 Mat 9 5.97 618 23.8 Example 24 Mat 12 5.93 619 20.8 Example 25 Mat 13 6.03 618 23.2 Example 26 Mat 27 5.88 619 22.5 Example 27 Mat 29 5.69 620 18.3 Example 28 Mat 40 5.81 620 20.8 Example 29 Mat 41 5.97 620 20.8 Example 30 Mat 56 5.93 618 23.2 Comparative Example 4 DCDDC 6.12 620 18.3 Comparative Example 5 DCM2 5.76 623 17.7 Comparative Example 6 DCJTB 6.32 628 17.1

From Table 2, in the case of the organic light-emitting devices manufactured in Examples 12 to 30, the driving voltage, the emission peak, and the current efficiency were obtained in Comparative Examples 3, 4, and 5, respectively, due to the rigid chemical structure and the structure favorable to the formation of excitons in the emission layer. It can be confirmed that it is superior to the driving voltage, emission peak, and current efficiency of the manufactured organic light emitting device.

10: positive electrode 20: negative electrode
30: organic layer 31: hole transport layer
32: light emitting layer 33: hole transport auxiliary layer
34: electron transport layer 35: electron transport auxiliary layer
36: electron injection layer 37: hole injection layer

Claims (12)

A compound represented by the following formula (1):
[Formula 1]

In Formula 1,
Ar ₁ To Ar ₅ Are the same as or different from each other, and each independently a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, Heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ to C ₃₀ aryl group, heteroaryl group having 2 to 30 nuclear atoms, C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ aryloxy group , C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphine group , C ₆ ~ C ₆₀ Mono or diarylphosphinyl group and C ₆ ~ C ₆₀ Selected from the group consisting of an arylamine group,
The Ar ₁ To Ar ₅ Alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group , mono or diarylphosphinyl group and arylamine group are each independently a C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ Arylox Period, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Arylphos Pin group, C ₆ ~ C ₆₀ Mono or diarylphosphinyl group and C ₆ ~ C ₆₀ When substituted with one or more substituents selected from the group consisting of an arylamine group or unsubstituted, and substituted with a plurality of substituents, they are the same as each other or may be different,
Y ₁ To Y ₃ Are the same as or different from each other, and each independently a direct bond, O or S,
m and n are 0 or 2. The method of claim 1,
The compound represented by Formula 1 is a compound represented by Formula 2 below:
[Formula 2]

In Formula 2,
Ar ₁ to Ar ₄ , Y ₁ to Y ₃ , m and n are as defined in claim 1. According to claim 1,
The Y ₃ is O or S compound. According to claim 1,
Wherein Ar ₁ , Ar ₂ and Ar ₅ are the same as or different from each other, and each independently represent any one of Formulas A-1 to A-2:
[Formula A-1]

[Formula A-2]

In Formulas A-1 to A-2,
The dotted line means the part where the condensation takes place,
Z ₁ are the same as or different from each other, each independently C or N,
R ₁ To R ₂ Are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted C ₁ ~ C ₃₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₃₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₃₀ alkynyl group, substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₃₀ A substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having 2 to 30 nuclear atoms. According to claim 1,
Wherein Ar ₃ To Ar ₄ Are the same as or different from each other, each independently represented by any one of Formulas B-1 to B-2 Compound:
[Formula B-1]

[Formula B-2]

In Formulas B-1 to B-2,
* is the part where the bond is made,
Z ₂ are the same as or different from each other, each independently C or N,
R ₃ To R ₄ Are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, substituted or unsubstituted C ₁ ~ C ₃₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₃₀ alkenyl group, substituted or unsubstituted C ₂ ~ C ₃₀ alkynyl group, substituted or unsubstituted C ₃ ~ C ₄₀ cycloalkyl group, substituted or unsubstituted heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₃₀ A substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having 2 to 30 nuclear atoms. According to claim 1,
When Z _One To Z ₂ of Ar _One To Ar ₅ All are C, at least one of R _One To R ₅ Is a substituted or unsubstituted heteroaryl group having 2 to 30 nuclear atoms. According to claim 1,
The compound is a compound characterized in that it is selected from the group consisting of:

An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode,
At least one of the one or more organic material layers is an organic electroluminescent device comprising a compound represented by the formula (1) of claim 1. 9. The method of claim 8,
The organic material layer comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and a light emitting layer, an organic electroluminescent device. 10. The method of claim 9,
The light emitting layer is an organic electroluminescent device, characterized in that for emitting delayed fluorescence. 10. The method of claim 9,
The light emitting layer is a delayed fluorescent light emitting layer including a host and a dopant,
The dopant is an organic electroluminescent device comprising a compound represented by the formula (1) of claim 1. 10. The method of claim 9,
The light emitting layer is an organic electroluminescent device, characterized in that the thermally activated delayed fluorescent light emitting layer emitting blue light.

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