KR101820932B1 - New host material and organic electroluminescent device using the same - Google Patents

New host material and organic electroluminescent device using the same Download PDF

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KR101820932B1
KR101820932B1 KR1020150135978A KR20150135978A KR101820932B1 KR 101820932 B1 KR101820932 B1 KR 101820932B1 KR 1020150135978 A KR1020150135978 A KR 1020150135978A KR 20150135978 A KR20150135978 A KR 20150135978A KR 101820932 B1 KR101820932 B1 KR 101820932B1
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light emitting
compound
independently
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organic
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KR20160041768A (en
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박상미
남현국
함주석
이주영
박세환
장승희
백용구
조규오
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주식회사 알파켐
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
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    • C—CHEMISTRY; METALLURGY
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    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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    • C07—ORGANIC CHEMISTRY
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    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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Abstract

The present invention relates to a novel luminescent host material and an organic luminescent device using the same. The organic luminescent device according to the present invention not only excels in luminescence characteristics but also enhances a driving voltage, thereby inducing an increase in power efficiency, .

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to novel host materials for luminescence and organic light-

The present invention relates to a novel luminescent host material and an organic luminescent device using the same, and more particularly, to a novel luminescent host material, a benzoquinoline derivative and a benzoquinazoline derivative, and an organic luminescent device including the luminescent host material .

An organic light emitting device is a device that injects electric charge into an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode) to form an electron and a hole. It is possible to form a device on a flexible transparent substrate such as a plastic substrate and to operate at a lower voltage (10 V or less) than a plasma display panel or an inorganic EL display, It is relatively small and has an advantage of excellent color.

The structure of a general organic electroluminescent device includes a substrate, a cathode, a hole injecting layer for receiving holes from the anode, a hole transporting layer for transporting holes, a light emitting layer for emitting light by combining holes and electrons, An electron transport layer, and a cathode. In some cases, a light emitting layer may be formed by doping a small amount of a fluorescent or phosphorescent dye to an electron transporting layer or a hole transporting layer without a separate light emitting layer. In the case of using a polymer, a hole transporting layer, a light emitting layer, and an electron transporting layer Can be performed simultaneously. The organic thin film layers between the two electrodes are formed by a vacuum deposition method, a spin coating method, an ink jet printing method, a roll coating method, or the like, and a separate electron injection layer may be inserted to efficiently inject electrons from the cathode.

Since the interface between the electrode and the organic material is stabilized, or the organic material has a large difference in moving speed between the hole and the electron, if a suitable hole transporting layer and electron transporting layer are used, holes and electrons can be effectively transferred to the light emitting layer. And the electron density are balanced so as to increase the luminous efficiency, the organic light emitting device is fabricated as a multilayer thin film structure.

The most important factor determining the luminous efficiency in an organic light emitting device is a light emitting material. However, the development of a phosphorescent material on a light-emitting mechanism is one of the ways that the luminous efficiency can be improved more theoretically. Accordingly, a variety of phosphorescent materials have been developed to date, In particular, CBP is the most widely known phosphorescent host material, and an organic electroluminescent device using a BAlq derivative as a host is known. However, an organic electroluminescent device using a phosphorescent material has a significantly higher current efficiency than a device using a fluorescent material. However, when a material such as BAlq or CBP is used as a host of a phosphorescent material, There is no significant advantage in terms of power efficiency due to a high voltage and satisfactory level of life of the device can not be achieved, and development of a more stable and high-performance host material is required.

Accordingly, the inventors of the present invention have conducted studies on a light emitting host material in consideration of the problems of the prior art, and as a result, they have found that a novel luminescent host material, benzoquinoline derivative and benzoquinazoline And an organic light emitting device using the same.

It is an object of the present invention to provide a novel benzoquinoline derivative and a benzoquinazoline derivative which are host materials for luminescence.

Another object of the present invention is to provide an organic light emitting device having improved light emitting characteristics and a driving voltage by using the novel light emitting host material, thereby improving power efficiency and improving power consumption .

The present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

Figure 112015093573007-pat00001

[In the above formula (1)

R 1 to R 6 are independently of each other hydrogen, deuterium or (C 1 -C 30) alkyl;

X and Y are independently selected from N and CH, and at least one is N;

L 1 and L 2 independently of one another are a single bond, (C 6 -C 30) arylene or (C 3 -C 30) heteroarylene and at least one is arylene or heteroarylene;

V 1 and V 2 independently of one another are hydrogen, (C 1 -C 30) alkyl, mono (C 6 -C 30) arylamino, di (C 6 -C 30) arylamino, tri (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, (C6-C30) aryl or (C3-C30) heteroaryl;

Wherein R 1 alkyl of 1 to R 6, L 1 arylene and a and L 2 heteroarylene, alkyl, aryl and heteroaryl groups of V 1 and V 2 are (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C6-C30) aryl, (C3-C30) aryl (C3-C30) heteroaryl, (C3-C30) heteroaryl substituted with (C6-C30) arylsilyl, di (C1-C30) alkylsilyl, di (C1-C30) alkylsilyl, mono- or di (C6-C30) arylsilyl, nitro, and hydroxy;

Wherein said heteroarylene and heteroaryl comprise at least one heteroatom selected from B, N, O, S, P (= O), Si and P.

According to an embodiment of the present invention, L < 1 > and L < 2 > may be a single bond or a compound selected from the following structures.

Figure 112015093573007-pat00002

[In the above structure,

R 21 to R 25 independently of one another are hydrogen, deuterium, (C 1 -C 30) alkyl, mono (C 6 -C 30) arylamino, di (C 6 -C 30) arylamino, tri (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, (C6-C30) aryl or (C3-C30) heteroaryl.

According to one embodiment of the present invention, V 1 and V 2 are independently of each other hydrogen or a compound selected from the following structures.

Figure 112015093573007-pat00003

[In the above structure,

R 11 to R 14 independently of one another are hydrogen, deuterium, (C 1 -C 30) alkyl or (C 6 -C 30) aryl.

According to one embodiment of the present invention, the compound represented by Formula 1 may be a compound represented by Formula 2 or 3.

(2)

Figure 112015093573007-pat00004

(3)

Figure 112015093573007-pat00005

[In the formulas (2) and (3)

R 1 to R 6 independently from each other are hydrogen, deuterium, (C 1 -C 30) alkyl;

L 1 and L 2 independently of one another are a single bond, (C 6 -C 30) arylene or (C 3 -C 30) heteroarylene and at least one is arylene or heteroarylene;

V 1 and V 2 independently of one another are hydrogen, (C 1 -C 30) alkyl, mono (C 6 -C 30) arylamino, di (C 6 -C 30) arylamino, tri (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, (C6-C30) aryl or (C3-C30) heteroaryl;

Wherein said heteroarylene and heteroaryl comprise at least one heteroatom selected from B, N, O, S, P (= O), Si and P.

According to one embodiment of the present invention, the compound may be preferably selected from the following compounds.

Figure 112015093573007-pat00006

Figure 112015093573007-pat00007

Figure 112015093573007-pat00008

Figure 112015093573007-pat00009

Figure 112015093573007-pat00010

Figure 112015093573007-pat00011

Figure 112015093573007-pat00012

Figure 112015093573007-pat00013

Figure 112015093573007-pat00014

Figure 112015093573007-pat00015

Figure 112015093573007-pat00016

Figure 112015093573007-pat00017

Figure 112015093573007-pat00018

Figure 112015093573007-pat00019

Figure 112015093573007-pat00020

Figure 112015093573007-pat00021

Figure 112015093573007-pat00022

Figure 112015093573007-pat00023

Figure 112015093573007-pat00024

Figure 112015093573007-pat00025

Figure 112015093573007-pat00026

Figure 112015093573007-pat00027

Figure 112015093573007-pat00028

Figure 112015093573007-pat00029

Figure 112015093573007-pat00030

Figure 112015093573007-pat00031

Figure 112015093573007-pat00032

Figure 112015093573007-pat00033

Figure 112015093573007-pat00034

Figure 112015093573007-pat00035

Figure 112015093573007-pat00036

Figure 112015093573007-pat00037

Figure 112015093573007-pat00038

Figure 112015093573007-pat00039

Figure 112015093573007-pat00040

Figure 112015093573007-pat00041

Figure 112015093573007-pat00042

Figure 112015093573007-pat00043

Figure 112015093573007-pat00044

The compounds according to one embodiment of the present invention may be more preferably selected from the following compounds.

Figure 112015093573007-pat00045

Figure 112015093573007-pat00046

The host material for luminescence according to the present invention has advantages of high brightness and excellent luminous efficiency as well as enhancing the driving voltage to induce an increase in power efficiency and to manufacture an organic light emitting device having improved power consumption.

1 is a graph showing the luminous efficiency of an organic luminescent device using Examples 4 to 6 and Comparative Example 1,
FIG. 2 is a graph showing power efficiency of the organic light emitting device using the fourth through sixth embodiments and the first comparative example,
3 is a graph showing lifetime of a device of an organic light emitting device using Examples 4 to 6 and Comparative Example 1,
4 is a graph showing the luminous efficiency of the organic luminescent device using Examples 1 to 3 and Comparative Example 1,
FIG. 5 is a graph showing power efficiency of the organic light emitting device using the embodiment 1 to 3 and the comparative example 1,
6 is a graph showing lifetime of a device of an organic light emitting device using Examples 1 to 3 and Comparative Example 1. FIG.

The novel host material for luminescence and the organic light emitting device using the same according to the present invention will be described below. However, unless otherwise defined in technical terms and scientific terms used herein, And the description of known functions and configurations which may unnecessarily obscure the gist of the present invention will be omitted in the following description.

The present invention relates to a luminescent host material represented by the following general formula (1) and an organic luminescent device including the luminescent host material. The luminescent host material according to the present invention is excellent in light emission characteristics, And thus an organic light emitting device having improved power consumption can be manufactured.

Further, the organic light emitting device comprising the compound represented by the following formula (1) according to the present invention in the light emitting layer necessarily includes benzoquinoline or benzoquinazoline, which can be easily applied in a deposition or solution process, has excellent thermal stability, The density is high and the luminous efficiency is high.

[Chemical Formula 1]

Figure 112015093573007-pat00047

[In the above formula (1)

R 1 to R 6 are independently of each other hydrogen, deuterium or (C 1 -C 30) alkyl;

X and Y are independently selected from N and CH, and at least one is N;

L 1 and L 2 independently of one another are a single bond, (C 6 -C 30) arylene or (C 3 -C 30) heteroarylene and at least one is arylene or heteroarylene;

V 1 and V 2 independently of one another are hydrogen, (C 1 -C 30) alkyl, mono (C 6 -C 30) arylamino, di (C 6 -C 30) arylamino, tri (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, (C6-C30) aryl or (C3-C30) heteroaryl;

Wherein R 1 alkyl of 1 to R 6, L 1 arylene and a and L 2 heteroarylene, alkyl, aryl and heteroaryl groups of V 1 and V 2 are (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C6-C30) aryl, (C3-C30) aryl (C3-C30) heteroaryl, (C3-C30) heteroaryl substituted with (C6-C30) arylsilyl, di (C1-C30) alkylsilyl, di (C1-C30) alkylsilyl, mono- or di (C6-C30) arylsilyl, nitro, and hydroxy;

Wherein said heteroarylene and heteroaryl comprise at least one heteroatom selected from B, N, O, S, P (= O), Si and P.

The substituents comprising the "alkyl", "alkoxy" and other "alkyl" moieties described in the present invention include both linear and branched forms, and "cycloalkyl" includes both single ring systems as well as substituted or unsubstituted adamantyl Or a plurality of cyclic hydrocarbons such as substituted or unsubstituted (C7-C30) bicycloalkyl. &Quot; Aryl " in the present invention means an organic radical derived from an aromatic hydrocarbon by one hydrogen elimination and is a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms, And includes a form in which a plurality of aryls are connected by a single bond. Specific examples include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, . Heteroaryl " as used in the present invention includes 1 to 4 hetero atoms selected from B, N, O, S, P (= O), Si and P as aromatic ring skeletal atoms and the remaining aromatic ring skeletal atoms are carbon An aryl group, a 5- to 6-membered monocyclic heteroaryl, and a polycyclic heteroaryl condensed with one or more benzene rings, and may be partially saturated. The heteroaryl in the present invention also includes a form in which one or more heteroaryl is connected to a single bond. The heteroaryl groups include divalent aryl groups in which the heteroatoms in the ring are oxidized or trisubstituted to form, for example, an N-oxide or a quaternary salt. Specific examples include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, Monocyclic heteroaryl such as tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoiso Benzothiazolyl, benzothiazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, (Such as pyridyl N-oxide, quinolyl N-oxide), polycyclic heteroaryls such as benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, benzyloxycarbonyl, Quaternary salts and the like.

In order to obtain excellent luminous efficiency in the formula 1 according to an embodiment of the present invention, L 1 and L 2 may be independently selected from a single bond or the following structure, but are not limited thereto.

Figure 112015093573007-pat00048

[In the above structure,

R 21 to R 25 independently of one another are hydrogen, deuterium, (C 1 -C 30) alkyl, mono (C 6 -C 30) arylamino, di (C 6 -C 30) arylamino, tri (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, (C6-C30) aryl or (C3-C30) heteroaryl.

Preferably, V 1 and V 2 are independently hydrogen or a group of the following formulas (1) and (2), respectively, in order to facilitate electron transfer and excellent luminous efficiency, But is not limited thereto.

Figure 112015093573007-pat00049

[In the above structure,

R 11 to R 14 independently of one another are hydrogen, deuterium, (C 1 -C 30) alkyl or (C 6 -C 30) aryl.

In the formula (1) according to the present invention, the compound represented by the following formula (2) or (3) may be more preferable from the viewpoint of having excellent solution phase thin film type performance.

(2)

Figure 112015093573007-pat00050

(3)

Figure 112015093573007-pat00051

[In the formulas (2) and (3)

R 1 to R 6 independently from each other are hydrogen, deuterium, (C 1 -C 30) alkyl;

L 1 and L 2 independently of one another are a single bond, (C 6 -C 30) arylene or (C 3 -C 30) heteroarylene and at least one is arylene or heteroarylene;

V 1 and V 2 independently of one another are hydrogen, (C 1 -C 30) alkyl, mono (C 6 -C 30) arylamino, di (C 6 -C 30) arylamino, tri (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, (C6-C30) aryl or (C3-C30) heteroaryl;

Wherein said heteroarylene and heteroaryl comprise at least one heteroatom selected from B, N, O, S, P (= O), Si and P.

The host material for luminescence according to the present invention can be exemplified by the following compounds in view of the improvement of the electron mobility and the improvement of the efficiency of the device, but the present invention is not limited thereto.

Figure 112015093573007-pat00052

Figure 112015093573007-pat00053

Figure 112015093573007-pat00054

Figure 112015093573007-pat00055

Figure 112015093573007-pat00056

Figure 112015093573007-pat00057

Figure 112015093573007-pat00058

Figure 112015093573007-pat00059

Figure 112015093573007-pat00060

Figure 112015093573007-pat00061

Figure 112015093573007-pat00062

Figure 112015093573007-pat00063

Figure 112015093573007-pat00064

Figure 112015093573007-pat00065

Figure 112015093573007-pat00066

Figure 112015093573007-pat00067

Figure 112015093573007-pat00068

Figure 112015093573007-pat00069

Figure 112015093573007-pat00070

Figure 112015093573007-pat00071

Figure 112015093573007-pat00072

Figure 112015093573007-pat00073

Figure 112015093573007-pat00074

Figure 112015093573007-pat00075

Figure 112015093573007-pat00076

Figure 112015093573007-pat00077

Figure 112015093573007-pat00078

Figure 112015093573007-pat00079

Figure 112015093573007-pat00080

Figure 112015093573007-pat00081

Figure 112015093573007-pat00082

Figure 112015093573007-pat00083

Figure 112015093573007-pat00084

Figure 112015093573007-pat00085

Figure 112015093573007-pat00086

Figure 112015093573007-pat00087

Figure 112015093573007-pat00088

Figure 112015093573007-pat00089

Figure 112015093573007-pat00090

The compounds according to the present invention may be exemplified by the following compounds in view of their excellent thermal stability and applicability to various functional layers by vapor deposition or solution processes, but the present invention is not limited thereto.

Figure 112015093573007-pat00091

Figure 112015093573007-pat00092

The compound of the present invention can be prepared by the method illustrated by the following Reaction Scheme 1, but it is not limited thereto and can be prepared through a known organic reaction.

[Reaction Scheme 1]

Figure 112015093573007-pat00093

[Reaction Scheme 1]

R 1 to R 6 are independently of each other hydrogen, deuterium or (C 1 -C 30) alkyl;

X and Y are independently selected from N and CH, and at least one is N;

L 1 and L 2 independently of one another are a single bond, (C 6 -C 30) arylene or (C 3 -C 30) heteroarylene and at least one is arylene or heteroarylene;

V 1 and V 2 independently of one another are hydrogen, (C 1 -C 30) alkyl, mono (C 6 -C 30) arylamino, di (C 6 -C 30) arylamino, tri (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, (C6-C30) aryl or (C3-C30) heteroaryl;

Wherein R 1 alkyl of 1 to R 6, L 1 arylene and a and L 2 heteroarylene, alkyl, aryl and heteroaryl groups of V 1 and V 2 are (C1-C30) alkyl, halo (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryloxy, (C6-C30) aryl, (C3-C30) aryl (C3-C30) heteroaryl, (C3-C30) heteroaryl substituted with (C6-C30) arylsilyl, di (C1-C30) alkylsilyl, di (C1-C30) alkylsilyl, mono- or di (C6-C30) arylsilyl, nitro, and hydroxy;

Wherein said heteroarylene and heteroaryl comprise at least one heteroatom selected from B, N, O, S, P (= O), Si and P;

A 1 and A 2 are each independently halogen,

Figure 112015093573007-pat00094
,
Figure 112015093573007-pat00095
Or -OTf;

B 1 and B 2 are each independently hydrogen, halogen,

Figure 112015093573007-pat00096
,
Figure 112015093573007-pat00097
Or -OTf.]

In addition, the present invention provides an organic light emitting device, wherein the organic light emitting device according to the present invention includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode. The organic material layer may have a single-layer structure including one layer, or a multilayer structure including two or more layers including a light-emitting layer. When the organic material layer of the organic light emitting device has a multilayer structure, it may have a structure in which a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer are stacked. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.

At this time, the luminescent host material of Formula 1 may be included in the organic material layer, and the compound of the present invention may be a phosphorescent host material having a large band gap and capable of realizing a clear yellow color. In addition, it may be mixed with the dopant material and included in the light emitting layer. By using the above-described light emitting host material according to the present invention in the light emitting layer, high color purity can be exhibited. The dopant material may be a fluorescent dopant, a phosphorescent dopant, or a mixed material thereof. The fluorescent dopant or phosphorescent dopant applied to the organic light emitting device of the present invention is not particularly limited. Further, the organic light emitting diode according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

The host material for luminescence according to the present invention may be applied to organic solar cells, organic photoconductors or organic transistors, which are organic electronic devices, on a principle similar to that applied to organic light emitting devices.

The present invention provides a light emitting device including the above-described organic electronic device according to the present invention. The light emitting device may be an organic thin film transistor (OTFT), an organic sensor, or the like, and the light emitting device may be manufactured by including the light emitting host material according to the present invention, A light emitting device having excellent performance and long lifetime can be realized.

The present invention also provides an electronic apparatus including the light emitting device. Examples of the electronic device include a television, a mobile phone, a camera, a sensor, and the like. By using the host material for luminescence according to the present invention, color reproducibility, high color purity, low power consumption, It is possible to realize a long life span.

Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are intended to illustrate the invention and are not intended to limit the scope of the invention.

[ Example 1] Preparation of Compound 6

Manufacture of Core 1-1

Figure 112015093573007-pat00098

3,5-Dibromobenzaldehyde (20.0 g, 75.8 mmol) was completely dissolved in 400 mL of ethanol, followed by addition of 1-Tetralone (15.5 g, 106.1 mmol) and the temperature was cooled to 0 ° C. 20 mL of 8.5 M NaOH aqueous solution was slowly dropped while maintaining the temperature at 0 to 5 占 폚. After completion of the addition, the resulting solid compound was filtered after further stirring for 1 hour. The filtered solid compound was washed twice with ethanol and then dried. After drying, pale yellow solid compound Core 1-1 (22.0 g, 74.0%) was obtained.

1 H-NMR (CDCl 3) δ [ppm]: 7.88 [s, 1H], 7.73 [d, 1H], 7.68 [t, 1H], 7.61 [s, 1H], 7.51 [s, 2H], 7.46- 7.48 [m, 2H], 3.10-2.90 [m, 4H].

Manufacture of Core 1-2

Figure 112015093573007-pat00099

120 mL of pyridine was added to the reactor, and Phenacyl bromide (12.0 g, 60.3 mmol) was added slowly while stirring. After completion of the addition, the resulting solid compound was filtered after further stirring for 1 hour. The filtered solid compound was washed twice with diethyl ether and dried. After drying, a white solid compound Core 1-2 (13.0 g, 77.5%) was obtained.

1 H-NMR (CDCl 3) δ [ppm]: 9.05 [d, 2H], 8.75 [t, 1H], 8.29 [t, 2H], 8.08 [d, 2H], 7.78 [t, 1H], 7.67 [ t, 2 H], 6.74 [s, 2 H].

Manufacture of Core 1-3

Figure 112015093573007-pat00100

Core 1-2 (12.8 g, 45.9 mmol) was completely dissolved in 150 mL of acetic acid, Core 1-1 (15.0 g, 38.3 mmol) was added, and the mixture was heated and stirred until completely dissolved. Ammonium acetate (14.7 g, 191.3 mmol) was added in small portions. After completion of the addition, the mixture was refluxed and stirred for 12 hours. After completion of the reaction, the temperature was cooled to room temperature (20 캜) and filtered. The filtered solid compound was washed with methanol and water, dissolved in toluene, and then crystals were precipitated with methanol. The precipitated solid compound was filtered and dried to obtain a pale yellow solid compound Core 1-3 (12.3 g, 65.4%).

1 H-NMR (CDCl 3) δ [ppm]: 8.30 [d, 2H], 8.14 [d, 1H], 7.96 [s, 2H], 7.54 [t, 2H], 7.45-7.35 [m, 6H], 2.99 [s, 4 H].

Manufacture of Core 1-4

Figure 112015093573007-pat00101

After adding Core 1 - 3 (12.0 g, 24.4 mmol), 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (12.2 g, 53.7 mmol) and 1,4- And the mixture was refluxed and stirred. After completion of the reaction, the temperature was cooled to room temperature (20 캜), water was added to the reactor, and the mixture was stirred for 1 hour. The reaction mixture was extracted with methylene chloride, concentrated, and then subjected to column chromatography to obtain solid compound Core 1-4 (8.10 g, 67.8%).

1 H-NMR (CDCl 3) δ [ppm]: 8.51 [d, 1H], 8.30 [m, 2H], 8.16 [d, 1H], 8.06 [d, 1H], 7.92 [s, 1H], 7.81 [ d, 1 H], 7.70-7.60 [m, 3H] 7.55-7.40 [m 5H].

Preparation of Compound 6

Figure 112015093573007-pat00102

(0.10 g, 0.8 mmol), Ethylenediamine (0.10 g, 1.6 mmol), K 3 PO 4 (10.4 g, 49.1 mmol), Carbazole (6.02 g, 36.0 mmol) Was dissolved in 200 ml of toluene, and the mixture was refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature (20 캜), and 500 ml of methanol was added thereto to precipitate a solid compound. After filtration, the solid compound precipitated with water and methanol was washed and subjected to column chromatography to obtain solid compound 6 (8.2 g, 75.8%).

1 H-NMR (CDCl 3) δ [ppm]: 8.55 [d, 2H], 8.51 [m, 1H], 8.30 [d, 2H], 8.16-8.05 [m, 6H], 7.94 [d, 2H], 7.81 [d, 1H], 7.69-7.60 [m, 5H], 7.54-7.47 [m, 5H], 7.40 [s, 1H], 7.35-7.20 [

MALDI-TOF MS: m / z 662.02, cal. 661.79.

[ Example 2] Preparation of Compound 41

Preparation of Compound 41-1

Figure 112015093573007-pat00103

(12.54 g, 55 mmol), dibenzo [b, d] thiophen-4-ylboronic acid (12.54 g, 55 mmol), Pd (pph 3 ) 4 (12.6 g, 55.2 mmol) and 2 MK 2 CO 3 Dissolved in 1,500 ml of toluene, and refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature (20 캜), and 1000 ml of methanol was added to precipitate a solid. Filtered, washed with water and methanol, and subjected to column chromatography to obtain solid compound 41-1 (12.4 g, 36%).

1 H-NMR (CDCl 3 ): 8.51 [1H, t], 8.45 [1H, d], 8.41 , 8.06 [1H, d], 7.98 [1H, d], 7.81 [1H, t], 7.52-7.65 [4H, m], 7.55-7.45 [9H, m], 7.40-7.32 [

Preparation of Compound 41

Figure 112015093573007-pat00104

Compound 41-1 (12.4 g, 20.98 mmol), 4,4,5,5-Tetramethyl-2- (triphenylene-2-yl) -1,3,2-dioxaborolane (8.2 g, 23.1 mmol), Pd 3 ) 4 (0.73 g, 0.63 mmol), 2M K 2 CO 3 50 ml were dissolved in 250 ml of toluene, and the mixture was refluxed and stirred for 12 hours. After completion of the reaction, the mixture was cooled to room temperature (20 캜), and 500 ml of methanol was added thereto to precipitate a solid compound. The precipitated solid compound was filtered out, washed with water and methanol, and subjected to column chromatography to obtain a solid compound 41 (11.4 g, 73%).

1 H-NMR (CDCl 3) : 9.15 [s, 1H]. 8.93 [d, 2H], 8.55-8.40 [m, 4H], 8.30 [s, 2H], 8.25-7.85 [m 8H], 7.75-7.65 [m, 10H], 7.60-7.45 [m, 6H].

MALDI-TOF MS: m / z 740.55, cal. 739.92

[ Example 3] Preparation of Compound 51

Manufacture of Core 2-2

Figure 112015093573007-pat00105

Core 1-1 (35.0 g, 89.3 mmol), Benzamidine hydrochloride (16.8 g, 107.1 mmol) and ethanol (180 mL) were added and dissolved. A solution of KOH (12.5 g, 223.2 mmol) in 450 ml of ethanol was slowly added thereto. After completion of the addition, the mixture was refluxed for 24 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the mixture was extracted with MC. The organic layer was concentrated and then subjected to column chromatography to obtain a solid compound Core 2-2 (14.5 g, 28%).

1 H-NMR (CDCl 3 )? [Ppm]: 8.30 [d, 2H], 7.96 [s, 2H], 7.54 [t, 2H], 7.45-7.35 [m, 6H], 2.99 [s, 4H].

Manufacture of Core 2-3

Figure 112015093573007-pat00106

Core 2.2 (12.8 g, 26 mmol), DDQ (12.2 g, 53.7 mmol) and 180 mL of 1,4-dioxane were added, followed by reflux stirring for 12 hours. After completion of the reaction, the temperature was cooled to room temperature, water was added to the reactor, and the mixture was stirred for 1 hour. The mixture was extracted with methylene chloride, concentrated, and then subjected to column chromatography to obtain a solid compound (10.7 g, 84%).

1 H-NMR (CDCl 3) δ [ppm]: 8.51 [d, 1H], 8.30 [m, 2H], 8.16 [d, 1H], 8.06 [d, 1H], 7.81 [d, 1H], 7.70- 7.60 [m, 3 H] 7.55 - 7.40 [m 5 H].

Preparation of Compound 51

Figure 112015093573007-pat00107

Ethylenediamine (0.10 g, 1.6 mmol) and K 3 PO 4 (10.4 g, 49.1 mmol) were added to a solution of Core 2-3 (8.00 g, 16.4 mmol), Carbazole (6.02 g, 36.0 mmol) Was dissolved in 200 ml of toluene, and the mixture was stirred under reflux for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and 500 ml of methanol was added to precipitate a solid. Filtered, washed with water and methanol, and subjected to column chromatography to obtain a solid compound 51 (7.5 g, 69.0%).

1 H-NMR (CDCl 3) δ [ppm]: 8.55 [d, 2H], 8.51 [m, 1H], 8.28 [d, 2H], 8.16-8.05 [m, 5H] 7.94 [d, 2H], 7.84 [d, 1H], 7.70-7.20 [m, 17H]

MALDI-TOF MS: m / z 663.02, calc. 662.78

[ Example 4] Preparation of Compound 94

Preparation of Compound 94-1

Figure 112015093573007-pat00108

(100 g, 691 mmol), 2-Tetralone (101.1 g, 691 mmol), acetic acid (8.3 g, 138.3 mmol) and ethanol (1300 mL) were added to a 3000 mL-2-necked round bottom flask, Respectively. After reaction for 12 hours, the reaction product was cooled to room temperature. The precipitated solid was filtered under reduced pressure, and washed with methanol to obtain a pale yellow solid compound 94-1 (121.3 g, 80%).

1 H-NMR (CDCl 3) δ [ppm]: 7.52 [d, 1H], 7.42 [t, 1H], 7.35-7.29 [m, 2H], 7.24-7.21 [m, 2H], 7.16 [t, 1H ], 7.02 [d, IH], 6.92 [d, IH], 3.09 [t, 2H], 2.95 [t, 2H].

Preparation of Compound 94-2

Figure 112015093573007-pat00109

After addition of compound 94-1 (10 g, 45.6 mmol), 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (22.7 g, 10352 mmol) and 1,4- And the mixture was refluxed and stirred. After completion of the reaction, the temperature was cooled to room temperature (20 캜), water was added to the reactor, and the mixture was stirred for 1 hour. The mixture was extracted with methylene chloride, concentrated, and then subjected to column chromatography to obtain a solid compound 94-2 (5.1 g, 51.8%).

1 H-NMR (CDCl 3 )? [Ppm]: 7.95 [d, 1H], 7.81 [d, 1H], 7.74 7.2-7.12 [m, 3H].

Preparation of Compound 94

Figure 112015093573007-pat00110

Core 1-4 (15 g, 30.7 mmol ) and compound 94-2 (14.6 g, 67.5 mmol) , CuI (0.6 g, 3.1 mmol), Ethylenediamine (0.4 g, 6.1 mmol), K 3 PO 4 (13 g, 61.3 mmol) were dissolved in 450 ml of toluene, and the mixture was refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature (20 캜), and 500 ml of methanol was added thereto to precipitate a solid compound. After filtration, the solid compound precipitated with water and methanol was washed out and column was carried out to obtain solid compound 94 (17 g, 73%).

1 H-NMR (CDCl 3 )? [Ppm]: 8.39 [s, 1H], 8.04-7.91 [m, 13H], 7.86 [s, 1H], 7.72-7.67 [m, 3H], 7.6-7.47 [ , 9H], 7.41 [t, IH], 7.33 [d, IH], 7.24 [t, 2H], 7.17 [t, 2H], 6.96 [

MALDI-TOF MS: m / z 761.91, cal. 761.12.

[ Example 5] Preparation of Compound 127

Preparation of Compound 127

Figure 112015093573007-pat00111

(9.6 g, 44.6 mmol), CuI (0.4 g, 2 mmol), Ethylenediamine (0.2 g, 4.1 mmol), K 3 PO 4 (8.6 g, 40.5 mmol) was dissolved in 200 ml of toluene, and the mixture was refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature (20 캜), and 500 ml of methanol was added thereto to precipitate a solid compound. After filtration, the solid compound precipitated with water and methanol was washed out and column was carried out to obtain solid compound 127 (13 g, 88%).

1 H-NMR (CDCl 3 )? [Ppm]: 8.22 [s, 1H], 8.19 [s, 1H], 8.13 [s, 1H], 8.08-8.01 [m, 7H], 7.99-7.95 [ ], 7.87-7.83 [m, 3H], 7.77 [t, 3H], 7.6 [t, 1H], 7.53-7.38 [m, 10H], 7.26

MALDI-TOF MS: m / z 728.9, cal. 728.15.

[ Example 6] Preparation of Compound 130

Preparation of Compound 130

Figure 112015093573007-pat00112

(15 g, 71.8 mmol), CuI (0.6 g, 3.3 mmol), Ethylenediamine (0.4 g, 6.5 mmol), K 3 PO 4 (13.9 g, 65.3 mmol) was dissolved in 480 ml of toluene, and the mixture was refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature (20 캜), and 500 ml of methanol was added thereto to precipitate a solid compound. After filtration, the solid compound precipitated with water and methanol was washed and subjected to column chromatography to obtain solid compound 130 (18 g, 72%).

1 H-NMR (CDCl 3) δ [ppm]: 8.29 [s, 1H], 8.19 [d, 1H], 8.1-7.98 [m, 8H], 7.83-7.7 [m, 6H], 7.64 [d, 1H ], 7.59-7.45 [m, 10H], 7.32 [d, IH], 7.26 [t, 2H], 7.18 [t, 2H], 7.02 [t, IH], 6.88 [t, IH].

MALDI-TOF MS: m / z 762.9, cal. 762.22.

[ Example  7] The light emitting host material Compound 6 ( Example 1) to  Fabrication of organic light emitting device using

A glass substrate of 25 mm x 25 mm x 0.7 mm, having an ITO (indium tin oxide) transparent electrode line with a thin film thickness of 150 nm, was ultrasonically cleaned for 10 minutes in distilled water containing detergent dissolved therein, Lt; / RTI > After the distilled water was cleaned, the substrate was ultrasonically cleaned by using a solvent of isopropyl alcohol, acetone, and methanol for 10 minutes sequentially and dried. Subsequently, the substrate was dry-cleaned with oxygen / argon plasma, and then a glass substrate having a transparent electrode line was mounted on a substrate holder of a vacuum evaporation apparatus. On the surface where the transparent electrode line was formed, a film thickness of 60 (biphenyl-4,4'-diyl) bis (N1- (naphthalen-1-yl) -N4, N4-diphenylbenzene-1,4-diamine). Next, H-1 (tetrakis-N-biphenyl-4-yl-benzidine, hereinafter referred to as H-1 film) with a film thickness of 30 nm was formed as a hole transporting layer on the hole injection layer material film. Next, AYPD was deposited as a dopant on the H-1 film and a light-emitting host was deposited on the inventive compound material at a weight ratio of 5% to form a light emitting layer having a thickness of 20 nm. Next, Alq 3 was formed into an electron transport layer, and Liq (lithium quinolate) was deposited thereon to form an electron injection layer. Metal aluminum was deposited on the Liq film to form a metal cathode, thereby fabricating an organic light emitting device.

A voltage of 0 to 15 V was applied to the thus fabricated organic luminescent electronic device, and a luminescence test was performed. The electroluminescence characteristics and basic physical property measurement results are shown in Table 1 and Figs. 4 to 6.

[Example 8] Production of organic light emitting device using compound 41 (Example 2) according to the present invention

An organic light emitting device was fabricated under the same conditions as in Example 7, except that Compound 41 was used instead of Compound 6 as the material of the light emitting layer in Example 7. The results are shown in Table 1 and FIGS. 4 to 6, The measurement results are shown.

[Example 9] Fabrication of organic light emitting device using compound 51 (Example 3) according to the present invention

An organic light emitting device was fabricated under the same conditions as in Example 7 except that the compound 51 was used instead of the compound 6 as the material of the light emitting layer in Example 7. The following Table 1 and Figures 4 to 6 show the electroluminescent characteristics and basic properties The measurement results are shown.

[Example 10] Fabrication of organic light emitting device using Compound 94 (Example 4) according to the present invention

An organic light emitting device was fabricated under the same conditions as in Example 7, except that the compound 94 was used instead of the compound 6 as the material of the light emitting layer in Example 7. The following Table 1 and Figs. 1 to 3 show electroluminescent characteristics and basic properties The measurement results are shown.

[Example 11] Fabrication of organic light emitting device using compound 127 (Example 5) according to the present invention

An organic light emitting device was fabricated under the same conditions as in Example 7 except that the compound 127 was used instead of the compound 6 as the material of the light emitting layer in Example 7. The following Table 1 and Figs. The measurement results are shown.

[Example 12] Fabrication of an organic light emitting device using Compound 130 (Example 6) according to the present invention

An organic light emitting device was fabricated under the same conditions as in Example 7 except that Compound 130 was used in place of Compound 6 as a material of the light emitting layer in Example 7. The following Table 1 and Figs. The measurement results are shown.

[Comparative Example 1] Fabrication of organic light emitting device using compound CBP

An organic light emitting device was fabricated under the same conditions as in Example 7, except that the compound CBP having the following structure was used instead of the compound 6 as the electron transport layer material in Example 7, and as shown in Table 1 and Figs. 1 to 6 Electroluminescence characteristics and fundamental properties of the device.

Figure 112015093573007-pat00113

Figure 112015093573007-pat00114

Figure 112015093573007-pat00115

 As shown in Tables 1 and 2, it was confirmed that the organic luminescent device comprising the compound according to the present invention as a luminescent host material in the light emitting layer exhibited excellent device characteristics as compared with the conventional materials, Emitting layer as a light emitting host material has excellent light emission characteristics with excellent luminance and high efficiency, and it is confirmed that power consumption can be improved by enhancing driving voltage.

It was also confirmed that the organic light emitting device containing the light emitting host material according to the present invention can have high lifetime characteristics.

Claims (10)

A compound represented by the following formula (1).
[Chemical Formula 1]
Figure 112017054922486-pat00116

[In the above formula (1)
R 1 to R 6 are independently of each other hydrogen, or deuterium;
X and Y are independently selected from N and CH, and at least one is N;
L 1 and L 2 independently of one another are a single bond and are selected from the following structures: R 21 to R 25 in the structures below are independently of each other hydrogen, deuterium, mono (C 6 -C 30) arylamino, di (C 6 -C 30) Arylamino, (C6-C30) aryl or (C3-C30) heteroaryl;
Figure 112017054922486-pat00168

V 1 and V 2 are independently of each other hydrogen, and are selected from the following structures;
Figure 112017054922486-pat00169

Figure 112017054922486-pat00170

Wherein L 1 -V 1 and L 2 -V 2 are not hydrogen;
The case where L 1 and V 1 are simultaneously a carbazole and L 2 and V 2 are simultaneously a carbazole are excluded] delete delete The method according to claim 1,
A compound represented by the following formula 2 or 3;
(2)
Figure 112017054922486-pat00119

(3)
Figure 112017054922486-pat00120

[In the formulas (2) and (3)
R 1 to R 6 are independently of each other hydrogen, or deuterium;
L 1 and L 2 are independently of each other a single bond, and are selected from the following structures;
Figure 112017054922486-pat00171

V 1 and V 2 are independently of each other hydrogen, and are selected from the following structures;
Figure 112017054922486-pat00172

Figure 112017054922486-pat00173

Wherein L 1 -V 1 and L 2 -V 2 are not hydrogen;
The case where L 1 and V 1 are simultaneously a carbazole and L 2 and V 2 are simultaneously a carbazole are excluded] The method according to claim 1,
Lt; / RTI > is selected from the following compounds.
Figure 112017054922486-pat00121

Figure 112017054922486-pat00122

Figure 112017054922486-pat00123

Figure 112017054922486-pat00174

Figure 112017054922486-pat00125

Figure 112017054922486-pat00175

Figure 112017054922486-pat00129

Figure 112017054922486-pat00130

Figure 112017054922486-pat00131

Figure 112017054922486-pat00132

Figure 112017054922486-pat00133

Figure 112017054922486-pat00176

Figure 112017054922486-pat00177

Figure 112017054922486-pat00178

Figure 112017054922486-pat00139

Figure 112017054922486-pat00140

Figure 112017054922486-pat00141

Figure 112017054922486-pat00142

Figure 112017054922486-pat00179

Figure 112017054922486-pat00180

Figure 112017054922486-pat00145

Figure 112017054922486-pat00181

Figure 112017054922486-pat00182

Figure 112017054922486-pat00151

Figure 112017054922486-pat00183

Figure 112017054922486-pat00154

Figure 112017054922486-pat00184

Figure 112017054922486-pat00185
 6. The method of claim 5,
Lt; / RTI > is selected from the following compounds.
Figure 112015093573007-pat00160

Figure 112015093573007-pat00161
 An organic electroluminescent device comprising a compound according to any one of claims 1 and 4 to 6. 8. The method of claim 7,
The organic light emitting device includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer comprises a light emitting layer containing the compound. A light emitting device comprising the organic light emitting device according to claim 8. An electronic device comprising the light emitting device according to claim 9.
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