KR20160142918A - Compound for organic electroluminescent device and organic electroluminescent device comprising the same - Google Patents

Compound for organic electroluminescent device and organic electroluminescent device comprising the same Download PDF

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KR20160142918A
KR20160142918A KR1020150078446A KR20150078446A KR20160142918A KR 20160142918 A KR20160142918 A KR 20160142918A KR 1020150078446 A KR1020150078446 A KR 1020150078446A KR 20150078446 A KR20150078446 A KR 20150078446A KR 20160142918 A KR20160142918 A KR 20160142918A
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electroluminescent device
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이순창
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머티어리얼사이언스 주식회사
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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Abstract

The present invention relates to a novel compound for an organic electroluminescent device and an organic electroluminescent device comprising the same and, more specifically, to a novel triphenylene-based compound used in an organic electroluminescent device and to an organic electroluminescent device having excellent properties such as low driving voltage, high light emitting efficiency, and long lifespan.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound for an organic electroluminescent device and an organic electroluminescent device including the same.

The present invention relates to a novel compound for organic electroluminescent devices and an organic electroluminescent device comprising the same, and more particularly to a novel triphenylene compound which can be used for an organic electroluminescent device, An organic electroluminescent device having excellent characteristics such as light emitting efficiency and long life.

The organic electroluminescent device is simple in structure and has various advantages in manufacturing process compared to other flat panel display devices such as a liquid crystal display (LCD), a plasma display panel (PDP) and a field emission display (FED) And has a high response speed and a low driving voltage, so that it is being actively developed to be used as a light source for a flat panel display such as a wall-mounted TV or a backlight of a display, a lighting, and a billboard.

In general, when a direct current voltage is applied to an organic electroluminescent device, holes injected from the anode recombine with electrons injected from the cathode to form an electron-hole pair exciton, and the exciton returns to a stable ground state, It is converted into light by transmission to the material.

In order to improve the efficiency and stability of the organic electroluminescent device, CW Tang, et al. (Kaw Tang, SA Vanslyke, et al.) Reported a low-voltage driving organic electroluminescent device by forming a laminated organic thin film between two opposite electrodes Applied Physics Letters, vol. 51, p. 913, 1987), research on organic materials for multilayer thin film structure organic electroluminescent devices is actively under way. The efficiency and lifetime of such a stacked organic electroluminescent device are closely related to the molecular structure of the material constituting the thin film. For example, the structure of the host material, the hole transporting layer material, or the electron transporting layer material in the material constituting the thin film affects the thermal stability of the device. In general, stability should be ensured even at a temperature of 100 ° C or higher. Otherwise, the crystallization of the material lowers the efficiency and shortens the lifetime of the device. This is because the chemical structure of the material greatly affects the power efficiency of the device. The power efficiency of the device is as follows.

P??? Phi / V

?: the ratio of holes to electrons in the light emitting layer

ψ: quantum efficiency of the luminescent material

φ: electron spin state contributing to light emission

V: drive voltage

Here, ψ and φ are values due to the luminescent material, respectively, and are determined by the quantum efficiency and the spin state of the material. However, the driving voltage and the combination ratio of the holes and electrons are determined by the charge injection barrier and the charge mobility, respectively. Therefore, in order to improve the power efficiency in the state where the light emitting layer is determined, the driving voltage should be lowered by using a material having a high charge mobility, and the ratio of holes and electrons in the light emitting layer must be increased. As the hole transporting material which has been used so far, there is NPD, and the hole transporting speed of this material has a value of 10 -3 cm 2 / Vs.

On the other hand, Alq 3 used as an electron transport material has a value of about 10 -5 cm 2 / Vs, so that holes are dominant in the light emitting layer. Of course, BCP (APL. 76, 197, 2000) and dimethylsilole derivative (JACS, 118, 11974, 1996) showing electron mobility of 10-4 cm2 / Vs have been reported, There is a limit.

Therefore, development of materials having high thermal stability and high electron mobility is required. In the case of blue luminescence, the light is emitted in all directions of the cathode and the anode, so that the absorption of the electron transport layer in the blue color must be minimized, which is also a requirement of the electron transport material.

It is an object of the present invention to provide an organic electroluminescent device which can be applied to an organic electroluminescent device and which has high electrical stability, excellent electron injection and transportation ability, minimal blue absorption and is used for an electron transfer layer (ETL) A compound for an organic electroluminescence device.

Another object of the present invention is to provide an organic electroluminescent device including the above-described compounds and having characteristics such as low driving voltage, high luminous efficiency and long life.

According to an embodiment of the present invention, there is provided a compound for an organic electroluminescent device represented by the following Formula 1:

[Chemical Formula 1]

Figure pat00001

In Formula 1,

R 1 and R 2 are each independently a C 1 to C 10 alkyl group, a C 2 to C 10 alkenyl group, a C 2 to C 10 alkynyl group, a C 3 to C 10 cycloalkyl group, one heterocycloalkyl group, C 6 ~ C 30 aryl group, the number of nuclear atoms of 5 to 30 heteroaryl group, C 1 ~ C 10 of alkyloxy and C 6 ~ C 10 of the aryloxy group is selected from the group consisting of;

L 1 is selected from the group consisting of a single bond, a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;

m and n are each independently an integer of 0 to 3;

R 3 is a substituent represented by the following formula (2);

(2)

Figure pat00002

In Formula 2,

R 4 and R 5 are each independently a C 1 to C 10 alkyl group, a C 2 to C 10 alkenyl group, a C 2 to C 10 alkynyl group, a C 3 to C 10 cycloalkyl group, of a heterocycloalkyl group, C 6 ~ C 30 aryl group, the number of nuclear atoms of 5 to 30 heteroaryl group, a fluorenyl group, a spiro-fluorene group, a C 1 ~ C 10 alkyloxy group of and C 6 ~ C 10 An aryloxy group, an aryloxy group,

In the above formulas (1) and (2)

An alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, a fluorene group, an alkyloxy group and an aryloxy group of the R 1 to R 2 and R 4 to R 5 are C 1 to C 10 alkyl group, C 2 ~ C 10 alkenyl group, C 2 ~ C 10 alkynyl group, C 3 ~ C 10 cycloalkyl group, the number of nuclear atoms of 3 to 10 heterocycloalkyl group, C 6 ~ C 30 of the aryl group , A heteroaryl group having 5 to 30 nuclear atoms, a fluorene group, a spirofluorene group, an alkyloxy group having 1 to 10 carbon atoms, and an aryloxy group having 6 to 20 carbon atoms Or not.

According to one preferred embodiment of the present invention, L < 1 > may be selected from the group consisting of a single bond, phenylene, naphthalene and pyridinyl.

According to a preferred embodiment of the present invention, R 4 and R 5 are each independently a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted A spirofluorene group and a substituted or unsubstituted heteroaryl group having 5 to 30 nucleus atoms.

According to a preferred embodiment of the present invention, R 4 and R 5 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthalenyl, substituted or unsubstituted Substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted spirofluorene, substituted or unsubstituted imidazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, And unsubstituted carbazolyl.

According to another embodiment of the present invention, there is provided an organic electroluminescent device including a first electrode, a second electrode, and at least one organic material layer between the first electrode and the second electrode,

At least one of the single or plural organic layers includes the compound for an organic electroluminescence device according to the present invention.

Here, the organic material layer including the compound for an organic electroluminescence device may be selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, a hole transporting layer, a hole injecting layer, an electron transporting layer and an electron injecting layer, And the organic electroluminescent compound may be used as a phosphorescent host.

In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 10 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.

In the present invention, "alkenyl" means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 10 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

In the present invention, "alkynyl" means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 10 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

"Aryl" in the present invention means a monovalent substituent derived from a C6-C20 aromatic hydrocarbon having a single ring or a combination of two or more rings. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 30 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, and R represents an aryl group having 6 to 20 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

In the present invention, "alkyloxy" means a monovalent substituent group represented by R'O-, wherein R 'represents alkyl having 1 to 10 carbon atoms, and may be linear, branched or cyclic . ≪ / RTI > Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.

"Cycloalkyl" in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 10 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and the like.

"Heterocycloalkyl" in the present invention means a monovalent substituent derived from 3 to 10 non-aromatic hydrocarbons having 3 to 10 nuclear atoms, wherein at least one carbon, preferably 1 to 3 carbons, of the ring is N, O, S Or < RTI ID = 0.0 > Se. ≪ / RTI > Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

The compound provided in the present invention is excellent in electrical stability, injection or transportability of electrons or holes, and light emission characteristics, and is preferably used as an organic material layer of an organic electroluminescent device, particularly in an electron transport layer.

In addition, when an organic electroluminescent device is manufactured using the compound provided in the present invention, low driving voltage, high luminous efficiency, and long life characteristics can be secured.

Figs. 1 (a) to 1 (b) are graphs showing the results of evaluating the voltage-current characteristics of the organic electroluminescent devices of Example 1 and Comparative Example 1 in Evaluation Example 1. Fig.

Hereinafter, the present invention will be described in detail.

The present invention relates to a novel compound for organic electroluminescent devices and an organic electroluminescent device comprising the same, and more particularly to a novel triphenylene compound which can be used for an organic electroluminescent device, An organic electroluminescent device having excellent characteristics such as light emitting efficiency and long life.

1. New organic compounds

The compound for an organic electroluminescence device provided by the present invention is characterized by being represented by the following formula (1).

[Chemical Formula 1]

Figure pat00003

In Formula 1,

R 1 and R 2 are each independently a C 1 to C 10 alkyl group, a C 2 to C 10 alkenyl group, a C 2 to C 10 alkynyl group, a C 3 to C 10 cycloalkyl group, one heterocycloalkyl group, C 6 ~ C 30 aryl group, the number of nuclear atoms of 5 to 30 heteroaryl group, C 1 ~ C 10 of alkyloxy and C 6 ~ C 10 of the aryloxy group is selected from the group consisting of;

L 1 is selected from the group consisting of a single bond, a C 6 to C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;

m and n are each independently an integer of 0 to 3;

R 3 is a substituent represented by the following formula (2);

(2)

Figure pat00004

In Formula 2,

R 4 and R 5 are each independently a C 1 to C 10 alkyl group, a C 2 to C 10 alkenyl group, a C 2 to C 10 alkynyl group, a C 3 to C 10 cycloalkyl group, of a heterocycloalkyl group, C 6 ~ C 30 aryl group, the number of nuclear atoms of 5 to 30 heteroaryl group, a fluorenyl group, a spiro-fluorene group, a C 1 ~ C 10 alkyloxy group of and C 6 ~ C 10 An aryloxy group, an aryloxy group,

In the above formulas (1) and (2)

An alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, a fluorene group, an alkyloxy group and an aryloxy group of the R 1 to R 2 and R 4 to R 5 are C 1 to C 10 alkyl group, C 2 ~ C 10 alkenyl group, C 2 ~ C 10 alkynyl group, C 3 ~ C 10 cycloalkyl group, the number of nuclear atoms of 3 to 10 heterocycloalkyl group, C 6 ~ C 30 of the aryl group , A heteroaryl group having 5 to 30 nuclear atoms, a fluorene group, a spirofluorene group, an alkyloxy group having 1 to 10 carbon atoms, and an aryloxy group having 6 to 20 carbon atoms Or not.

According to one preferred embodiment of the present invention, L < 1 > may be selected from the group consisting of a single bond, phenylene, naphthalene and pyridinyl.

According to a preferred embodiment of the present invention, R 4 and R 5 are each independently a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted spirofluor And a substituted or unsubstituted heteroaryl group having 5 to 30 nucleus atoms.

According to a preferred embodiment of the present invention, R 4 and R 5 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene Substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted imidazolyl, A substituted quinolinyl group and a substituted or unsubstituted carbazolyl group.

According to a preferred embodiment of the present invention, when L 1 is phenylene, each of R 4 and R 5 independently represents a substituted or unsubstituted substituted or unsubstituted C 6 -C 30 aryl group, Or a heteroaryl group having 5 to 30 ring atoms in number.

In the present invention, the compound represented by Formula 1 may be represented by the following structure, but is not limited thereto.

Figure pat00005

Figure pat00006

Figure pat00007

Figure pat00008

Figure pat00009

Figure pat00010

Figure pat00011

Figure pat00012

Figure pat00013

Figure pat00014

Figure pat00015

Figure pat00016

Figure pat00017

Figure pat00018
Figure pat00019

Figure pat00020

Figure pat00021

Figure pat00022

Figure pat00023

Figure pat00024

In the present invention, the compound represented by Formula 1 may be synthesized according to a general synthesis method. Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

2. Organic electroluminescent device

According to another embodiment of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic material layer between the first electrode and the second electrode, wherein at least one of the organic material layers An organic electroluminescent device comprising the compound for an organic electroluminescent device according to the present invention is provided.

Here, the organic compound layer including the organic electroluminescence compound may be selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, a hole transporting layer, a hole injecting layer, an electron transporting layer, and an electron injecting layer. However, the compound for an organic electroluminescence device of the present invention has a high electrical stability, an excellent electron injecting and transporting ability, a minimum absorption of blue, and is preferably used for an electron transfer layer (ETL) Or as a phosphorescent host of the light emitting layer.

The organic electroluminescent device is preferably supported by a transparent substrate. The material of the transparent substrate is not particularly limited as long as it has good mechanical strength, thermal stability and transparency. Specific examples thereof include glass, transparent plastic film, and the like.

As the cathode material of the organic electroluminescent device of the present invention, a metal, an alloy, an electroconductive compound or a mixture thereof having a work function of 4 eV or more can be used. Specifically, transparent conductive materials such as Au or CuI, ITO (indium tin oxide), SnO2 and ZnO which are metals can be cited. The thickness of the positive electrode film is preferably 10 to 200 nm.

As the anode material of the organic electroluminescent device of the present invention, a metal, an alloy, an electrically conductive compound or a mixture thereof having a work function of less than 4 eV may be used. Specifically, Na, Na-K alloy, calcium, magnesium, lithium, lithium alloy, indium, aluminum, magnesium alloy and aluminum alloy can be mentioned. In addition, aluminum / AlO2, aluminum / lithium, magnesium / silver or magnesium / indium may also be used. The thickness of the negative electrode film is preferably 10 to 200 nm.

In order to increase the luminous efficiency of the organic electroluminescent device, it is preferable that at least one electrode has a light transmittance of preferably 10% or more. The sheet resistance of the electrode is preferably several hundreds? / Mm or less. The thickness of the electrode is 10 nm to 1 탆, more preferably 10 to 400 nm. Such an electrode can be manufactured by forming the electrode material into a thin film by a vapor deposition method such as chemical vapor deposition (CVD) or physical vapor deposition (PVD) or a sputtering method.

When the compound for an organic electroluminescence device of the present invention is used for the purpose of the present invention, the known hole transporting material, hole injecting material, light emitting layer material, host material of the light emitting layer, electron transporting material, May be used alone in each organic layer or may be used in combination with the organic electroluminescent device compound of the present invention.

As the hole transporting material, there may be mentioned N, N-dicarbazolyl-3,5-benzene (mCP), poly (3,4-ethylenedioxythiophene): polystyrene sulfonate (PEDOT: PSS) (NPD), N, N'-diphenyl-N, N'-di (3-methylphenyl) -4,4'- diaminobiphenyl (TPD ), N, N'-diphenyl-N, N'-dinaphthyl-4,4'-diaminobiphenyl, N, N, N'N'-tetra- (II) 1,10,15,20-tetraphenyl-21H, 23H-porphyrin and the like such as N, N, N'N'-tetraphenyl-4,4'-diaminobiphenyl, porphyrin compound derivatives, polymers having aromatic tertiary amines in the main chain or side chain, 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane, N, N, Triarylamine derivatives such as 4,4 ', 4'-tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, Metal phthalocyanine, phthalo such as copper phthalocyanine There may be mentioned non-derivatives, starburst amine derivatives, enamine stilbene derivatives, derivatives of aromatic tertiary amines and styrylamine compounds, polysilane and the like.

As the electron transporting material, diphenylphosphine oxide-4- (triphenylsilyl) phenyl (TSPO1), Alq3, 2,5-diarylsilole derivative (PyPySPyPy), perfluorinated compound (PF- And octasubstituted cyclooctatetraene compounds (COTs).

In the organic electroluminescent device of the present invention, the electron injecting layer, the electron transporting layer, the hole transporting layer, and the hole injecting layer may be formed of a single layer containing at least one kind of the above-mentioned compounds, And the like.

Examples of the light emitting material include a phosphorescent fluorescent material, a fluorescent whitening agent, a laser dye, an organic scintillator, and a reagent for fluorescence analysis. Specifically, there may be mentioned a carbazole-based compound, a phosphine oxide-based compound, a carbazole-based phosphine oxide compound, bis ((3,5-difluoro-4-cyanophenyl) pyridine) iridium picolinate (FCNIrpic) 8-hydroxyquinoline) Polyaromatic compounds such as aluminum (Alq3), anthracene, phenanthrene, pyrene, chrysene, perylene, coronene, rubrene and quinacridone, oligophenylene compounds such as quaterphenyl, Benzene, 1,4-bis (4-methylstyryl) benzene, 1,4-bis (4-methylstyryl) Bis (5-t-butyl-2-benzoxazolyl) thiophene, 1,4-diphenyl-1,3-butadiene, Liquid scintillation scintillators such as 6-diphenyl-1,3,5-hexatriene and 1,1,4,4-tetraphenyl-1,3-butadiene, metal complexes of oxine derivatives, coumarin dyes, Methylene pyran pigment, dicyanomethylene cyopyran pigment, polymer A tin dye, an oxobenzanthracene dye, a xanthene dye, a carbostyryl dye, a perylene dye, an oxazine compound, a stilbene derivative, a spiro compound, and an oxadiazole compound.

Each layer constituting the organic electroluminescent device of the present invention can be formed into a thin film through a known method such as vacuum deposition, spin coating or casting, or can be manufactured using materials used in each layer. The thickness of each of these layers is not particularly limited and may be appropriately selected according to the characteristics of the material, but may be determined usually in the range of 2 nm to 5,000 nm.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

Example

[Preparation Example 1] Triphenylene-2-ylboronic acid

<Reaction Scheme 1>

Figure pat00025

Under nitrogen, 10 mmol of 2-bromotriphenylene was dissolved in THF, and 11 mmol of n-BuLi (n-Butyllithium, 2.5M in n-hexane) was gradually added while maintaining the temperature at -78 with an acetone / dry ice bath. After 30 minutes, 12 mmol of TMB was added dropwise, the bath was removed, and the mixture was stirred at room temperature for 30 minutes.

The organic layer was extracted with 1N HCl and MC and recrystallized with Hex / MC to obtain triphenylene-2-ylboronic acid in a yield of 74%.

MS (FAB): 272 (M &lt; + &gt;).

Synthesis Example 1 Synthesis of N - ([1,1'-biphenyl] -4-yl) -N- (4- (triphenylene-2-yl) phenyl) pyridin-

Figure pat00026

Step 1. Preparation of 2- (4-bromophenyl) triphenylene

<Reaction Scheme 2>

Figure pat00027

10 mmol of triphenylene-2-ylboronic acid and 12 mmol of 1-bromo-4-iodobenzene were dissolved in toluene under nitrogen, and 30 mmol of Pd (PPh 3 ) 4 and 2M K 2 CO 3 were added and heated / refluxed . After completion of the reaction for 12 hours, the reaction was completed. The organic layer was extracted with H 2 O / MC and recrystallized from Hex / MC to obtain 2- (4-bromophenyl) triphenylene in a yield of 85%.

MS (FAB): 383 (M &lt; + &gt;).

Step 2. Preparation of [l, l'-biphenyl] -4-amine

<Reaction Scheme 3>

Figure pat00028

After the nick 15mmol acid 4-bromoaniline 10mmol, phenyl beam under nitrogen was dissolved in toluene, Pd (PPh 3) and heated / refluxed by the addition of 4 0.2mmol, 2M K 2 CO 3 30mmol. After completion of the reaction for 4 hours, the reaction was completed. The organic layer was extracted with H 2 O and MC, and the product was subjected to column chromatography using MC to obtain [1,1'-biphenyl] -4-amine in a yield of 79%.

MS (FAB): 169 (M &lt; + &gt;).

Step 3. Preparation of N - ([1,1'-biphenyl] -4-yl) pyridin-

<Reaction Scheme 4>

Figure pat00029

10 mmol of [1,1'-biphenyl] -4-amine and 10 mmol of 3-bromopyridine were dissolved in toluene under nitrogen, and then 0.2 mmol of Pd (OAc) 2 , 0.4 mmol of BINAP and 30 mmol of t- Respectively. After confirming the completion of the reaction 24 hours later, the organic layer was extracted with H 2 O / MC and then subjected to column chromatography and recrystallization using Hex / EA to obtain N - ([1,1'- biphenyl] -4-yl) pyridin- %. &Lt; / RTI &gt;

MS (FAB): 246 (M &lt; + &gt;).

Step 4. Preparation of N - ([1,1'-biphenyl] -4- yl) -N- (4- (triphenylene-2- yl) phenyl) pyridin-

Figure pat00030
Under nitrogen of 2- (4-bromophenyl) triphenylene 10mmol, N - ([1,1'- biphenyl] -4-yl) pyridine Pd (OAc) after a 3-amine was dissolved in toluene, 10mmol 2 0.2 mmol, 0.4 mmol of BINAP and 30 mmol of t-BuONa were added and heated / refluxed. After completion of the reaction for 24 hours, the reaction was completed and the organic layer was extracted with H 2 O / MC. The organic layer was then subjected to column chromatography and recrystallization using Hex / EA to obtain N - ([1,1'- biphenyl] Yl) phenyl) pyridin-3-amine in a yield of 69%.

1 H NMR (CDCl 3, 300Hz ): δ (ppm) = 8.90-8.80 (s, 1H), 8.79-8.62 (m, 5H), 8.58-8.46 (d, 1H), 8.36-8.24 (d, 1H) , 7.96-7.84 (d, 1H), 7.82-7.73 (d, 2H), 7.73-7.65 (m, 4H), 7.63-7.51 (m, 5H), 7.49-7.41 (t, 2H), 7.38-7.14 m, 6H)

MS (FAB): 548 (M &lt; + &gt;).

[Example 1] Fabrication of organic electroluminescent device

([1,1'-biphenyl] -4-yl) -N- (4- (triphenylene-2-yl) phenyl) pyridin- , And then an organic electroluminescent device was fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.

Liq 2 nm was introduced on the prepared ITO transparent electrode to prevent injection of holes from ITO. The compound of Synthesis Example 1 was laminated to a thickness of 36 nm and laminated in the order of 1 nm of LiF and 200 nm of Al to prepare a device capable of moving only electrons.

[Comparative Example 1] Fabrication of an organic electroluminescent device

A device was fabricated in the same manner as in Example 1, except that only Alq 3 was used instead of the compound of Synthesis Example 1 in Example 1.

[Evaluation Example 1]

In general, the TOF method is used to measure the charge mobility. However, since the film thickness is more than 1 μm, there is a problem that the organic material consumption is large. Also, in the measurement of the electron mobility, There is a problem that it is not measured well.

Therefore, indirect relative comparison is useful. In this case, a method of making a diode that only emits electrons is used and a method of comparing with a reference material is used. That is, the organic EL device manufactured in each of Example 1 and Comparative Example 1 has a voltage- -Current characteristic) was evaluated, and the results are shown graphically in FIG. 1 (a) to FIG. 1 (b).

As shown in FIGS. 1 (a) to 1 (b), when Alq 3 was used in the prior art, the current density was 0.005 mA / cm 2 at 2.5 V. In the case of using the compound according to the present invention V has a current density of 0.1 mA / cm &lt; 2 &gt; so that the electron mobility is remarkably increased. Also, the Tg of the material is 129.58 ° C, which indicates that the material has excellent thermal stability.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, It will be obvious to those of ordinary skill in the art.

Claims (10)

1. An organic electroluminescent device compound represented by the following formula (1): &lt; EMI ID =
[Chemical Formula 1]
Figure pat00052

(2)
Figure pat00053

here,
R 1 and R 2 are the same or different and each independently represents a C 1 to C 10 alkyl group, a C 2 to C 10 alkenyl group, a C 2 to C 10 alkynyl group, a C 3 to C 10 cycloalkyl group, A cycloalkyl group having 3 to 10 nuclear atoms, a C 6 to C 20 aryl group, a heteroaryl group having 5 to 20 nuclear atoms, a C 1 to C 10 alkyloxy group and a C 6 to C 10 aryloxy group Selected from the group consisting of;
L 1 is a single bond, a C 6 to C 18 arylene group or a heteroarylene group having 5 to 18 nuclear atoms;
m, n and p are each independently an integer of 0 to 3;
R 3 is a substituent represented by the above formula (2);
R 4 and R 5 are the same or different and each independently represents a C 1 to C 10 alkyl group, a C 2 to C 10 alkenyl group, a C 2 to C 10 alkynyl group, a C 3 to C 10 cycloalkyl group, A cycloalkyl group having 3 to 10 nuclear atoms, a C 6 to C 20 aryl group, a heteroaryl group having 5 to 20 nuclear atoms, a C 1 to C 10 alkyloxy group and a C 6 to C 10 aryloxy group &Lt; / RTI &gt;
An alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group and an aryloxy group of the R 1 to R 2 and R 4 to R 5 are a C 1 to C 10 alkyl group, C 2 ~ C 10 alkenyl group, C 2 ~ C 10 of the alkynyl group, C 3 ~ C 10 cycloalkyl group, a nuclear atoms 3 to 10 heterocycloalkyl group, C 6 ~ C 20 aryl group, nuclear atoms 5 to 20 heteroaryl groups, C 1 to C 10 alkyloxy groups and C 6 to C 20 aryloxy groups. The method according to claim 1,
Wherein the compound represented by Formula 1 is represented by Formula 3:
(3)
Figure pat00054

Wherein each of R 1 , R 2 , R 4 , R 5 , L 1 , m and n is as defined in claim 1. The method according to claim 1,
Wherein L &lt; 1 &gt; is a single bond, phenylene or naphthalene. The method according to claim 1,
And R 4 and R 5 are each independently a C 6 to C 20 aryl group or a heteroaryl group having 5 to 20 nucleus atoms. 5. The method of claim 4,
Wherein R 4 and R 5 are each independently selected from the group consisting of phenyl, biphenyl, naphthyl, fluorene, spirofluorene, imidazolyl, imidazolyl, pyridinyl, pyrimidinyl, quinolinyl and carbazolyl Wherein the organic compound is an organic compound. The method according to claim 1,
Wherein the compound is selected from the group consisting of the following compounds:
Figure pat00055

Figure pat00056

Figure pat00057

Figure pat00058

Figure pat00059

Figure pat00060

Figure pat00061

Figure pat00062

Figure pat00063

Figure pat00064

Figure pat00065

Figure pat00066

Figure pat00067

Figure pat00068

Figure pat00069
 1. An organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic material layer between the first electrode and the second electrode,
Wherein at least one of the single or plural organic material layers comprises the compound for organic electroluminescence device according to claim 1. 8. The method of claim 7,
Wherein the organic compound layer including the organic electroluminescence compound is selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, a hole transporting layer, a hole injecting layer, an electron transporting layer, and an electron injecting layer. 9. The method of claim 8,
Wherein the organic compound layer including the organic electroluminescence compound is an electron transport layer. 10. The method of claim 9,
Wherein the organic electroluminescent device compound is used as a phosphorescent host of the light emitting layer.
KR1020150078446A 2015-06-03 2015-06-03 Compound for organic electroluminescent device and organic electroluminescent device comprising the same KR20160142918A (en)

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KR20180099343A (en) * 2017-02-28 2018-09-05 주식회사 엘지화학 Fluorene derivatices, coating composition including fluorene derivatices and organic light emitting device using the same
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