WO2014061963A1 - Organic electroluminescence compounds and organic electroluminescence device comprising the same - Google Patents

Organic electroluminescence compounds and organic electroluminescence device comprising the same Download PDF

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WO2014061963A1
WO2014061963A1 PCT/KR2013/009197 KR2013009197W WO2014061963A1 WO 2014061963 A1 WO2014061963 A1 WO 2014061963A1 KR 2013009197 W KR2013009197 W KR 2013009197W WO 2014061963 A1 WO2014061963 A1 WO 2014061963A1
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unsubstituted
substituted
group
alkyl
aryl
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PCT/KR2013/009197
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French (fr)
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Jin-Hee Kim
Hyo-Jung Lee
Young-Gil Kim
Hyo-Nim Shin
Kyung-Joo Lee
Hong-Yoep NA
Young-Jun Cho
Hyuck-Joo Kwon
Bong-Ok Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Publication of WO2014061963A1 publication Critical patent/WO2014061963A1/en

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Definitions

  • the present invention relates to organic electroluminescence compounds and organic electroluminescence device comprising the same.
  • An electroluminescent (EL) device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time compared to LCDs.
  • An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules, and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • the electroluminescent material includes a host material and a dopant material for purposes of functionality.
  • a device that has much superior electroluminescent properties is known to have a structure in which a host is doped with a dopant to form an electroluminescent layer.
  • the development of an organic EL device having high efficiency and long lifespan is being urgently called for.
  • the development of materials much superior to conventional electroluminescent materials is urgent.
  • a host material which functions as the solvent in a solid phase and plays a role in transferring energy should be of high purity and must have a molecular weight appropriate to enabling vacuum deposition. Also, the glass transition temperature and heat decomposition temperature should be high to ensure thermal stability, and high electrochemical stability is required to attain a long lifespan, and the formation of an amorphous thin film should become simple, and the force of adhesion to materials of other adjacent layers must be good but interlayer migration should not occur.
  • fluorescent host materials have been widely used as a host material.
  • blue fluorescent host materials many materials are researched and commercialized after the development of 4,4'-bis(2,2'-diphenylvinyl)-1,1'-biphenyl (DPVBi) from Idemitsu Kosan.
  • DPVBi 4,4'-bis(2,2'-diphenylvinyl)-1,1'-biphenyl
  • the blue material system of Idemitsu Kosan and the dinaphthylanthracene, tetra(t-butyl)perylene system of Kodak are known, many researches are conducted until now to develop blue fluorescent host materials that can provide better characteristics in the device.
  • Korean Patent No. KR 10-0987822 B Korean Patent Appln. Laying-Open Nos. KR 10-2010-0108903 A, KR 10-2010-0109050 A, KR 10-2012-0038402 A, etc., disclose many anthracene derivatives.
  • the present inventors found that a specific structure of an anthracene derivative, which is not disclosed in the above references, is suitable for manufacturing an organic electroluminescent device having high luminous efficiency and a long lifespan.
  • the objective of the present invention is to provide a specific structure of an anthracene derivative which can be used as a fluorescent host material of a light-emitting layer to realize an organic electroluminescent device having a long lifespan and high luminous efficiency.
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 5- to 30-memebered heteroarylene group;
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group;
  • Ar 2 and Ar 3 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, or -NR 1 R 2 ;
  • R 1 and R 2 each independently represent hydrogen, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to each other to form a mono- or polycyclic, 3- to 30-membered, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
  • ring A and ring C each independently represent an aromatic ring represented by the following formula 1a;
  • ring B represents a 5-membered ring represented by the following formula 1b;
  • X and Y each independently represent -O-, -S-, -N(R 21 )- or -C(R 22 )(R 23 )-; where X is -C(R 22 )(R 23 )-, Y is -O-, -S- or -N(R 21 )-, where X is -O- or -S-, Y is -N(R 21 )- or -C(R 22 )(R 23 )-, and where X is -N(R 21 )-, Y is -O-, -S- or -C(R 22 )(R 23 )-;
  • R represents hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group;
  • R 21 to R 23 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur; and
  • a represents 1 or 2; where a is 2, each of R is same or different.
  • organic electroluminescence compound according to the present invention as a fluorescent host of a light-emitting layer, it is possible to manufacture an organic electroluminescence device having a long lifespan and high luminous efficiency.
  • the present invention relates to an organic electroluminescent compound represented by the above formula 1, an organic electroluminescent material comprising the compound, and an organic electroluminescence device comprising the material.
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent.
  • the substituents of the substituted alkyl, the substituted aryl(ene), and the substituted heteroaryl(ene) in L 1 , Ar 1 to Ar 3 , R, R 1 , R 2 , and R 21 to R 23 in the above formula 1 each independently are at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a (C1-C30)alkoxy, a (C6-C30)aryl, a 3- to 30-membered heteroaryl unsubstituted or substituted with a (C6-C30)aryl, a (C3-C30)cycloalkyl, a 5- to 7
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 5- to 30-memebered heteroarylene group, preferably represents a single bond, a substituted or unsubstituted (C6-C21)arylene group, or a substituted or unsubstituted 5- to 21-memebered heteroarylene group, and more preferably represents a single bond; a (C6-C21)arylene group unsubstituted or substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-memebered heteroarylene group.
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group, preferably represents a substituted or unsubstituted (C6-C21)aryl group, or a substituted or unsubstituted 5- to 21-membered heteroaryl group, and more preferably represents a (C6-C21)aryl group unsubstituted or substituted with deuterium, a halogen, a (C1-C6)alkyl, a (C1-C6)alkoxy, a (C6-C21)aryl, a (C3-C21)cycloalkyl, a tri(C6-C12)arylsilyl, a cyano, a di(C6-C12)arylamino, or a hydroxyl; or a 5- to 21-membered heteroaryl group unsubstituted or substituted with
  • Ar 2 and Ar 3 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, or -NR 1 R 2 , preferably each independently represent hydrogen, a substituted or unsubstituted (C6-C21)aryl group, a substituted or unsubstituted 5- to 21-membered heteroaryl group, or -NR 1 R 2 , and more preferably each independently represent hydrogen, an unsubstituted (C6-C21)aryl group, an unsubstituted 5- to 21-membered heteroaryl group, or -NR 1 R 2 .
  • R 1 and R 2 each independently represent hydrogen, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to each other to form a mono- or polycyclic, 3- to 30-membered, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur, preferably each independently represent hydrogen, or a substituted or unsubstituted (C6-C21)aryl group, and more preferably each independently represent hydrogen, or a (C6-C21)aryl group unsubstituted or substituted with a (C1-C6)alkyl.
  • X and Y each independently represent -O-, -S-, -N(R 21 )- or -C(R 22 )(R 23 )-; where X is -C(R 22 )(R 23 )-, Y is -O-, -S- or -N(R 21 )-, where X is -O- or -S-, Y is -N(R 21 )- or -C(R 22 )(R 23 )-, and where X is -N(R 21 )-, Y is -O-, -S- or -C(R 22 )(R 23 )-.
  • R represents hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group, and preferably represents hydrogen.
  • R 21 to R 23 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur, preferably each independently represent a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group, and more preferably each independently represent an unsubstituted (C1-C6)alkyl group, or an unsubstituted (C6-C21)aryl group.
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C21)arylene group, or a substituted or unsubstituted 5- to 21-memebered heteroarylene group;
  • Ar 1 represents a substituted or unsubstituted (C6-C21)aryl group, or a substituted or unsubstituted 5- to 21-membered heteroaryl group;
  • Ar 2 and Ar 3 each independently represent hydrogen, a substituted or unsubstituted (C6-C21)aryl group, a substituted or unsubstituted 5- to 21-membered heteroaryl group, or -NR 1 R 2 ;
  • R 1 and R 2 each independently represent hydrogen, or a substituted or unsubstituted (C6-C21)aryl group;
  • X and Y each independently represent -O-, -S-, -N(R 21 )- or -C(R 22 )(R 23 )-
  • L 1 represents a single bond; a (C6-C21)arylene group unsubstituted or substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-memebered heteroarylene group;
  • Ar 1 represents a (C6-C21)aryl group unsubstituted or substituted with deuterium, a halogen, a (C1-C6)alkyl, a (C1-C6)alkoxy, a (C6-C21)aryl, a (C3-C21)cycloalkyl, a tri(C6-C12)arylsilyl, a cyano, a di(C6-C12)arylamino, or a hydroxyl; or a 5- to 21-memebered heteroaryl group unsubstituted or substituted with a (C6-C21)aryl;
  • Ar 2 and Ar 3 each independently represent hydrogen; an unsubstituted or substituted
  • the representative compounds of formula 1 include the following compounds, but are not limited thereto:
  • organic electroluminescent compounds of the present invention can be prepared by a synthetic method known to a person skilled in the art. For example, they can be prepared according to the following reaction scheme 1 or 2.
  • Ar 1 , Ar 2 , Ar 3 , L 1 , X, ring A, ring B, and ring C are as defined in formula 1 above, and Hal represents a halogen.
  • the present invention provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
  • Said material can be comprised of the organic electroluminescent compound according to the present invention alone, or can additionally comprise conventional materials comprised in organic electroluminescent materials.
  • Said organic electroluminescent device comprises a first electrode; a second electrode; and at least one organic layer between said first and second electrodes.
  • Said organic layer may comprise at least one compound of formula 1 according to the present invention.
  • the organic layer comprises a light-emitting layer, and at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and a electron blocking layer.
  • said organic layer comprises a light-emitting layer
  • the organic electroluminescent compound of formula 1 can be used as a host material in the light-emitting layer.
  • said light-emitting layer can comprise a fluorescent dopant material with the host material of the present invention.
  • a fluorescent dopant is a compound which can emit light from a single exciton.
  • the fluorescent dopant is preferably a compound which is selected according to a required emission color from an amine-based compound, an aromatic compound, a chelate complex such as a tris(8-quinolinolate)aluminum complex, a coumarin derivative, a tetraphenylbutadiene derivative, a bisstyrylarylene derivative, an oxadiazole derivative, or the like.
  • a styrylamine compound, a styryldiamine compound, an arylamine compound, and an aryldiamine compound are more preferable, with a fused polycyclic amine derivative being even more preferable.
  • These fluorescent dopants may be used either singly or in combination of two or more.
  • a compound represented by the following formula 2 can be used as the fused polycyclic amine derivative comprised as a fluorescent dopant of the organic electroluminescent device according to the present invention.
  • Ar 21 represents a substituted or unsubstituted (C6-C50)aryl or a styryl;
  • L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 3- to 30-memebered heteroarylene;
  • Ar 22 and Ar 23 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 3- to 30-membered heteroaryl; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30- membered, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur; n represents 1 or 2, where n is 2, each of are same or different.
  • the preferable aryl groups of Ar 21 are a substituted or unsubstituted phenyl, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, and a substituted or unsubstituted benzofluorenyl group, etc.
  • the representative compounds of formula 2 include the following compounds, but are not limited thereto:
  • the organic electroluminescent device according to the present invention may further comprise, in addition to the organic electroluminescent compound represented by formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
  • the organic layer may further comprise a light-emitting layer and a charge generating layer.
  • the organic layer may form an organic electroluminescent device which emits white light by further comprising at least one organic light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound, besides said organic electroluminescent compound.
  • a surface layer may be preferably placed on an inner surface(s) of one or both electrode(s); selected from a chalcogenide layer, a metal halide layer and a metal oxide layer.
  • a chalcogenide(includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
  • a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
  • Such a surface layer provides operation stability for the organic electroluminescent device.
  • said chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and said metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be preferably placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, flow coating methods can be used.
  • a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
  • An OLED device was produced using the light emitting material according to the present invention.
  • a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol.
  • the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • N,N'-bis( ⁇ -naphthyl)-N,N'-diphenyl-4,4'-diamine was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • compound H-44 according to the present invention was introduced into one cell of the vacuum vapor depositing apparatus, as a host material, and compound D-55 was introduced into another cell as a dopant.
  • the two materials were evaporated at different rates and were deposited in a doping amount of 3 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
  • tris(8-hydroxyquinoline)-aluminum (III) was introduced into one cell to form an electron transport layer having a thickness of 30 nm on the light-emitting layer.
  • an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer.
  • All the materials used for producing the OLED device were purified by vacuum sublimation at 10 -6 torr prior to use.
  • the produced OLED device showed a blue emission having a luminance of 590 cd/m 2 and a current density of 23.6 mA/cm 2 .
  • An OLED device was produced in the same manner as in Device Example 1, except for using compound H-86 as a host, and using compound D-99 as a dopant of the light emitting material.
  • the produced OLED device showed a blue emission having a luminance of 1080 cd/m 2 and a current density of 15.7 mA/cm 2 .
  • An OLED device was produced in the same manner as in Device Example 1, except for using compound H-101 as a host, and using compound D-9 as a dopant of the light emitting material.
  • the produced OLED device showed a blue emission having a luminance of 630 cd/m 2 and a current density of 22.5 mA/cm 2 .
  • organic electroluminescent compound according to the present invention is efficient for blue emission as a fluorescent host of a light-emitting layer.

Abstract

The present invention relates to an organic electroluminescence compound and an organic electroluminescence device containing the same. Using the organic electroluminescence compound according to the present invention, it is possible to manufacture an organic electroluminescence device having long lifespan and high luminous efficiency.

Description

ORGANIC ELECTROLUMINESCENCE COMPOUNDS AND ORGANIC ELECTROLUMINESCENCE DEVICE COMPRISING THE SAME
The present invention relates to organic electroluminescence compounds and organic electroluminescence device comprising the same.
An electroluminescent (EL) device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time compared to LCDs. An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules, and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
The most important factor determining luminous efficiency in an organic EL device is the light-emitting material. The electroluminescent material includes a host material and a dopant material for purposes of functionality. Typically, a device that has much superior electroluminescent properties is known to have a structure in which a host is doped with a dopant to form an electroluminescent layer. Recently, the development of an organic EL device having high efficiency and long lifespan is being urgently called for. Particularly, taking into consideration the electroluminescent properties required of medium to large OLED panels, the development of materials much superior to conventional electroluminescent materials is urgent.
A host material which functions as the solvent in a solid phase and plays a role in transferring energy should be of high purity and must have a molecular weight appropriate to enabling vacuum deposition. Also, the glass transition temperature and heat decomposition temperature should be high to ensure thermal stability, and high electrochemical stability is required to attain a long lifespan, and the formation of an amorphous thin film should become simple, and the force of adhesion to materials of other adjacent layers must be good but interlayer migration should not occur.
Until now, fluorescent host materials have been widely used as a host material. For blue fluorescent host materials, many materials are researched and commercialized after the development of 4,4'-bis(2,2'-diphenylvinyl)-1,1'-biphenyl (DPVBi) from Idemitsu Kosan. Although the blue material system of Idemitsu Kosan and the dinaphthylanthracene, tetra(t-butyl)perylene system of Kodak are known, many researches are conducted until now to develop blue fluorescent host materials that can provide better characteristics in the device.
Korean Patent No. KR 10-0987822 B, and Korean Patent Appln. Laying-Open Nos. KR 10-2010-0108903 A, KR 10-2010-0109050 A, KR 10-2012-0038402 A, etc., disclose many anthracene derivatives.
The present inventors found that a specific structure of an anthracene derivative, which is not disclosed in the above references, is suitable for manufacturing an organic electroluminescent device having high luminous efficiency and a long lifespan.
The objective of the present invention is to provide a specific structure of an anthracene derivative which can be used as a fluorescent host material of a light-emitting layer to realize an organic electroluminescent device having a long lifespan and high luminous efficiency.
In order to achieve said purposes, the present invention provides an organic electroluminescence compound represented by the following formula 1:
Figure PCTKR2013009197-appb-I000001
wherein
L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 5- to 30-memebered heteroarylene group;
Ar1 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group;
Ar2 and Ar3 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, or -NR1R2;
R1 and R2 each independently represent hydrogen, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to each other to form a mono- or polycyclic, 3- to 30-membered, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
ring A and ring C each independently represent an aromatic ring represented by the following formula 1a;
ring B represents a 5-membered ring represented by the following formula 1b;
Figure PCTKR2013009197-appb-I000002
Figure PCTKR2013009197-appb-I000003
X and Y each independently represent -O-, -S-, -N(R21)- or -C(R22)(R23)-; where X is -C(R22)(R23)-, Y is -O-, -S- or -N(R21)-, where X is -O- or -S-, Y is -N(R21)- or -C(R22)(R23)-, and where X is -N(R21)-, Y is -O-, -S- or -C(R22)(R23)-;
R represents hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group;
R21 to R23 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur; and
a represents 1 or 2; where a is 2, each of R is same or different.
Using the organic electroluminescence compound according to the present invention as a fluorescent host of a light-emitting layer, it is possible to manufacture an organic electroluminescence device having a long lifespan and high luminous efficiency.
Hereinafter, the present invention will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
The present invention relates to an organic electroluminescent compound represented by the above formula 1, an organic electroluminescent material comprising the compound, and an organic electroluminescence device comprising the material.
The compound represented by the above formula 1 will be described in detail.
Herein, “alkyl” includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.; “alkenyl” includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.; “alkynyl” includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.; “cycloalkyl” includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.; “5- to 7-membered heterocycloalkyl” is a cycloalkyl having at least one heteroatom selected from B, N, O, S, P(=O), Si and P, preferably O, S and N, and 5 to 7 ring backbone atoms, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.; “aryl(ene)” is a monocyclic or fused ring derived from an aromatic hydrocarbon, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.; “3- to 30-membered heteroaryl(ene)” is an aryl group having at least one, preferably 1 to 4 heteroatom selected from the group consisting of B, N, O, S, P(=O), Si and P, and 3 to 30 ring backbone atoms; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. Further, “halogen” includes F, Cl, Br and I.
Herein, “substituted” in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent. The substituents of the substituted alkyl, the substituted aryl(ene), and the substituted heteroaryl(ene) in L1, Ar1 to Ar3, R, R1, R2, and R21 to R23 in the above formula 1 each independently are at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a (C1-C30)alkoxy, a (C6-C30)aryl, a 3- to 30-membered heteroaryl unsubstituted or substituted with a (C6-C30)aryl, a (C3-C30)cycloalkyl, a 5- to 7-membered heterocycloalkyl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl, a cyano, a carbazolyl, a di(C1-C30)alkylamino, a di(C6-C30)arylamino unsubstituted or substituted with a (C1-C30)alkyl, a (C1-C30)alkyl(C6-C30)arylamino, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, a (C1-C30)alkyl(C6-C30)aryl, a carboxyl, a nitro and a hydroxyl, and preferably each independently are at least one selected from the group consisting of deuterium, a halogen, a (C1-C6)alkyl, a (C1-C6)alkoxy, a (C6-C21)aryl, a (C3-C21)cycloalkyl, a tri(C6-C12)arylsilyl, a cyano, a di(C6-C12)arylamino, and a hydroxyl.
In formula 1, the moiety,
Figure PCTKR2013009197-appb-I000004
is preferably selected from the group consisting of the following structures:
Figure PCTKR2013009197-appb-I000005
wherein X, Y, R, and a are as defined in formula 1.
In formula 1, L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 5- to 30-memebered heteroarylene group, preferably represents a single bond, a substituted or unsubstituted (C6-C21)arylene group, or a substituted or unsubstituted 5- to 21-memebered heteroarylene group, and more preferably represents a single bond; a (C6-C21)arylene group unsubstituted or substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-memebered heteroarylene group.
Ar1 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group, preferably represents a substituted or unsubstituted (C6-C21)aryl group, or a substituted or unsubstituted 5- to 21-membered heteroaryl group, and more preferably represents a (C6-C21)aryl group unsubstituted or substituted with deuterium, a halogen, a (C1-C6)alkyl, a (C1-C6)alkoxy, a (C6-C21)aryl, a (C3-C21)cycloalkyl, a tri(C6-C12)arylsilyl, a cyano, a di(C6-C12)arylamino, or a hydroxyl; or a 5- to 21-membered heteroaryl group unsubstituted or substituted with a (C6-C21)aryl.
Ar2 and Ar3 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, or -NR1R2, preferably each independently represent hydrogen, a substituted or unsubstituted (C6-C21)aryl group, a substituted or unsubstituted 5- to 21-membered heteroaryl group, or -NR1R2, and more preferably each independently represent hydrogen, an unsubstituted (C6-C21)aryl group, an unsubstituted 5- to 21-membered heteroaryl group, or -NR1R2.
R1 and R2 each independently represent hydrogen, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to each other to form a mono- or polycyclic, 3- to 30-membered, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur, preferably each independently represent hydrogen, or a substituted or unsubstituted (C6-C21)aryl group, and more preferably each independently represent hydrogen, or a (C6-C21)aryl group unsubstituted or substituted with a (C1-C6)alkyl.
X and Y each independently represent -O-, -S-, -N(R21)- or -C(R22)(R23)-; where X is -C(R22)(R23)-, Y is -O-, -S- or -N(R21)-, where X is -O- or -S-, Y is -N(R21)- or -C(R22)(R23)-, and where X is -N(R21)-, Y is -O-, -S- or -C(R22)(R23)-.
R represents hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group, and preferably represents hydrogen.
R21 to R23 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur, preferably each independently represent a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group, and more preferably each independently represent an unsubstituted (C1-C6)alkyl group, or an unsubstituted (C6-C21)aryl group.
According to one embodiment of the present invention, in formula 1, L1 represents a single bond, a substituted or unsubstituted (C6-C21)arylene group, or a substituted or unsubstituted 5- to 21-memebered heteroarylene group; Ar1 represents a substituted or unsubstituted (C6-C21)aryl group, or a substituted or unsubstituted 5- to 21-membered heteroaryl group; Ar2 and Ar3 each independently represent hydrogen, a substituted or unsubstituted (C6-C21)aryl group, a substituted or unsubstituted 5- to 21-membered heteroaryl group, or -NR1R2; R1 and R2 each independently represent hydrogen, or a substituted or unsubstituted (C6-C21)aryl group; X and Y each independently represent -O-, -S-, -N(R21)- or -C(R22)(R23)-; where X is -C(R22)(R23)-, Y is -O-, -S- or -N(R21)-, where X is -O- or -S-, Y is -N(R21)- or -C(R22)(R23)-, and where X is -N(R21)-, Y is -O-, -S- or -C(R22)(R23)-; R represents hydrogen: and R21 to R23 each independently represent a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group.
According to another embodiment of the present invention, in formula 1, L1 represents a single bond; a (C6-C21)arylene group unsubstituted or substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-memebered heteroarylene group; Ar1 represents a (C6-C21)aryl group unsubstituted or substituted with deuterium, a halogen, a (C1-C6)alkyl, a (C1-C6)alkoxy, a (C6-C21)aryl, a (C3-C21)cycloalkyl, a tri(C6-C12)arylsilyl, a cyano, a di(C6-C12)arylamino, or a hydroxyl; or a 5- to 21-memebered heteroaryl group unsubstituted or substituted with a (C6-C21)aryl; Ar2 and Ar3 each independently represent hydrogen; an unsubstituted (C6-C21)aryl group; an unsubstituted 5- to 21-membered heteroaryl group; or -NR1R2; R1 and R2 each independently represent hydrogen, or a (C6-C21)aryl group unsubstituted or substituted with a (C1-C6)alkyl; X and Y each independently represent -O-, -S-, -N(R21)- or -C(R22)(R23)-; where X is -C(R22)(R23)-, Y is -O-, -S- or -N(R21)-, where X is -O- or -S-, Y is -N(R21)- or -C(R22)(R23)-, and where X is -N(R21)-, Y is -O-, -S- or -C(R22)(R23)-; R represents hydrogen: and R21 to R23 each independently represent an unsubstituted (C1-C6)alkyl group, or an unsubstituted (C6-C21)aryl group.
The representative compounds of formula 1 include the following compounds, but are not limited thereto:
Figure PCTKR2013009197-appb-I000006
Figure PCTKR2013009197-appb-I000007
Figure PCTKR2013009197-appb-I000008
Figure PCTKR2013009197-appb-I000009
Figure PCTKR2013009197-appb-I000010
Figure PCTKR2013009197-appb-I000011
Figure PCTKR2013009197-appb-I000012
Figure PCTKR2013009197-appb-I000013
Figure PCTKR2013009197-appb-I000014
Figure PCTKR2013009197-appb-I000015
Figure PCTKR2013009197-appb-I000016
Figure PCTKR2013009197-appb-I000017
Figure PCTKR2013009197-appb-I000018
Figure PCTKR2013009197-appb-I000019
Figure PCTKR2013009197-appb-I000020
Figure PCTKR2013009197-appb-I000021
Figure PCTKR2013009197-appb-I000022
Figure PCTKR2013009197-appb-I000023
Figure PCTKR2013009197-appb-I000024
Figure PCTKR2013009197-appb-I000025
Figure PCTKR2013009197-appb-I000026
Figure PCTKR2013009197-appb-I000027
Figure PCTKR2013009197-appb-I000028
Figure PCTKR2013009197-appb-I000029
The organic electroluminescent compounds of the present invention can be prepared by a synthetic method known to a person skilled in the art. For example, they can be prepared according to the following reaction scheme 1 or 2.
[Reaction Scheme 1]
Figure PCTKR2013009197-appb-I000030
[Reaction Scheme 2]
Figure PCTKR2013009197-appb-I000031
wherein Ar1, Ar2, Ar3, L1, X, ring A, ring B, and ring C are as defined in formula 1 above, and Hal represents a halogen.
In addition, the present invention provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
Said material can be comprised of the organic electroluminescent compound according to the present invention alone, or can additionally comprise conventional materials comprised in organic electroluminescent materials.
Said organic electroluminescent device comprises a first electrode; a second electrode; and at least one organic layer between said first and second electrodes. Said organic layer may comprise at least one compound of formula 1 according to the present invention.
One of the first and second electrodes is an anode, and the other is a cathode. The organic layer comprises a light-emitting layer, and at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and a electron blocking layer.
Also, said organic layer comprises a light-emitting layer, and the organic electroluminescent compound of formula 1 can be used as a host material in the light-emitting layer.
In addition, said light-emitting layer can comprise a fluorescent dopant material with the host material of the present invention.
A fluorescent dopant is a compound which can emit light from a single exciton. The fluorescent dopant is preferably a compound which is selected according to a required emission color from an amine-based compound, an aromatic compound, a chelate complex such as a tris(8-quinolinolate)aluminum complex, a coumarin derivative, a tetraphenylbutadiene derivative, a bisstyrylarylene derivative, an oxadiazole derivative, or the like. A styrylamine compound, a styryldiamine compound, an arylamine compound, and an aryldiamine compound are more preferable, with a fused polycyclic amine derivative being even more preferable. These fluorescent dopants may be used either singly or in combination of two or more.
As the fused polycyclic amine derivative comprised as a fluorescent dopant of the organic electroluminescent device according to the present invention, a compound represented by the following formula 2 can be used.
Figure PCTKR2013009197-appb-I000032
wherein
Ar21 represents a substituted or unsubstituted (C6-C50)aryl or a styryl; L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 3- to 30-memebered heteroarylene; Ar22 and Ar23 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 3- to 30-membered heteroaryl; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30- membered, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur; n represents 1 or 2, where n is 2, each of
Figure PCTKR2013009197-appb-I000033
are same or different.
The preferable aryl groups of Ar21 are a substituted or unsubstituted phenyl, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, and a substituted or unsubstituted benzofluorenyl group, etc.
The representative compounds of formula 2 include the following compounds, but are not limited thereto:
Figure PCTKR2013009197-appb-I000034
Figure PCTKR2013009197-appb-I000035
Figure PCTKR2013009197-appb-I000036
Figure PCTKR2013009197-appb-I000037
Figure PCTKR2013009197-appb-I000038
Figure PCTKR2013009197-appb-I000039
Figure PCTKR2013009197-appb-I000040
Figure PCTKR2013009197-appb-I000041
Figure PCTKR2013009197-appb-I000042
Figure PCTKR2013009197-appb-I000043
Figure PCTKR2013009197-appb-I000044
Figure PCTKR2013009197-appb-I000045
Figure PCTKR2013009197-appb-I000046
Figure PCTKR2013009197-appb-I000047
Figure PCTKR2013009197-appb-I000048
Figure PCTKR2013009197-appb-I000049
Figure PCTKR2013009197-appb-I000050
Figure PCTKR2013009197-appb-I000051
Figure PCTKR2013009197-appb-I000052
Figure PCTKR2013009197-appb-I000053
The organic electroluminescent device according to the present invention may further comprise, in addition to the organic electroluminescent compound represented by formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
In the organic electroluminescent device according to the present invention, the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal. The organic layer may further comprise a light-emitting layer and a charge generating layer.
In addition, the organic layer may form an organic electroluminescent device which emits white light by further comprising at least one organic light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound, besides said organic electroluminescent compound.
According to the present invention, at least one layer (hereinafter, "a surface layer”) may be preferably placed on an inner surface(s) of one or both electrode(s); selected from a chalcogenide layer, a metal halide layer and a metal oxide layer. Specifically, a chalcogenide(includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer. Such a surface layer provides operation stability for the organic electroluminescent device. Preferably, said chalcogenide includes SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and said metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
In the organic electroluminescent device according to the present invention, a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be preferably placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium. Further, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. A reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
In order to form each layer of the organic electroluminescent device according to the present invention, dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, flow coating methods can be used.
When using a wet film-forming method, a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
Hereinafter, the organic electroluminescent compound, the preparation method of the compound, and the luminescent properties of the device will be explained in detail with reference to the following examples.
Example 1: Preparation of compound H-44
Figure PCTKR2013009197-appb-I000054
After mixing compound A 5 g (15 mmol), 10-phenylanthracen-9-yl boronic acid 6.6 g (16.5 mmol), Pd(PPh3)4 1.0 g (0.9 mmol), K2CO3 (2 M) 22 mL, ethanol 22 mL, and toluene 44 mL in a flask, the mixture was stirred under reflux at 120°C for 4 hours. After the reaction was completed, the mixture was washed with distilled water, extracted with ethylacetate (EA), the organic layer was dried with MgSO4, the solvent was removed using a rotary evaporator, and the remaining product was separated using a column to obtain compound H-44, 4.4 g (48%).
Melting point 332°C, UV 312 nm (in toluene), PL 426 nm (in toluene), Molecular weight 611.26
Example 2: Preparation of compound H-86
Figure PCTKR2013009197-appb-I000055
After mixing compound B 3.5 g (8.2 mmol), 10-phenylanthracen-9-yl boronic acid 2.3 g (8.6 mmol), Pd(PPh3)4 568 mg (0.5 mmol), K2CO3 (2 M) 12 mL, ethanol 12 mL, and toluene 24 mL in a flask, the mixture was washed with distilled water, extracted with EA, the organic layer was dried with MgSO4, the solvent was removed using a rotary evaporator, and the remaining product was separated using a column to obtain compound H-86, 3.6 g (72%).
Melting point 374°C, UV 292 nm (in toluene), PL 426 nm (in toluene), Molecular weight 601.19
Example 3: Preparation of compound H-101
Figure PCTKR2013009197-appb-I000056
Compound H-101, 3.9 g (48.7%) was prepared in the same manner as the synthetic method of compound H-44 using compound C 6.7 g (13.9 mmol), and 9-bromo-10-phenylanthracene 3.9 g (11.6 mmol).
Melting point 358°C, UV 257 nm (in methylene chloride (MC)), PL 412 nm (in MC), Molecular weight 687.29
Device Example 1: Production of an OLED device using the
organic electroluminescent compound according to the present invention
An OLED device was produced using the light emitting material according to the present invention. A transparent electrode indium tin oxide (ITO) thin film (15 Ω/sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus. 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. Then, N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, compound H-44 according to the present invention was introduced into one cell of the vacuum vapor depositing apparatus, as a host material, and compound D-55 was introduced into another cell as a dopant. The two materials were evaporated at different rates and were deposited in a doping amount of 3 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Next, tris(8-hydroxyquinoline)-aluminum (III) was introduced into one cell to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. Thereafter, after depositing lithium quinolate as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 150 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. All the materials used for producing the OLED device were purified by vacuum sublimation at 10-6 torr prior to use.
The produced OLED device showed a blue emission having a luminance of 590 cd/m2 and a current density of 23.6 mA/cm2.
Device Example 2: Production of an OLED device using the
organic electroluminescent compound according to the present invention
An OLED device was produced in the same manner as in Device Example 1, except for using compound H-86 as a host, and using compound D-99 as a dopant of the light emitting material.
The produced OLED device showed a blue emission having a luminance of 1080 cd/m2 and a current density of 15.7 mA/cm2.
Device Example 3: Production of an OLED device using the
organic electroluminescent compound according to the present invention
An OLED device was produced in the same manner as in Device Example 1, except for using compound H-101 as a host, and using compound D-9 as a dopant of the light emitting material.
The produced OLED device showed a blue emission having a luminance of 630 cd/m2 and a current density of 22.5 mA/cm2.
It is verified that the organic electroluminescent compound according to the present invention is efficient for blue emission as a fluorescent host of a light-emitting layer.

Claims (7)

  1. An organic electroluminescence compound represented by the following formula 1:
    Figure PCTKR2013009197-appb-I000057
    wherein
    L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted 5- to 30-memebered heteroarylene group;
    Ar1 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group;
    Ar2 and Ar3 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- to 30-membered heteroaryl group, or -NR1R2;
    R1 and R2 each independently represent hydrogen, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to each other to form a mono- or polycyclic, 3- to 30-membered, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
    ring A and ring C each independently represent an aromatic ring represented by the following formula 1a;
    ring B represents a 5-membered ring represented by the following formula 1b;
    Figure PCTKR2013009197-appb-I000058
    Figure PCTKR2013009197-appb-I000059
    X and Y each independently represent -O-, -S-, -N(R21)- or -C(R22)(R23)-; where X is -C(R22)(R23)-, Y is -O-, -S- or -N(R21)-, where X is -O- or -S-, Y is -N(R21)- or -C(R22)(R23)-, and where X is -N(R21)-, Y is -O-, -S- or -C(R22)(R23)-;
    R represents hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group;
    R21 to R23 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 5- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, 3- to 30-membered, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur; and
    a represents 1 or 2; where a is 2, each of R is same or different.
  2. The organic electroluminescence compound according to claim 1, wherein the substituents of the substituted alkyl, the substituted aryl(ene), and the substituted heteroaryl(ene) in L1, Ar1 to Ar3, R, R1, R2, and R21 to R23 each independently are at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a (C1-C30)alkoxy, a (C6-C30)aryl, a 3- to 30-membered heteroaryl unsubstituted or substituted with a (C6-C30)aryl, a (C3-C30)cycloalkyl, a 5- to 7-membered heterocycloalkyl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, a (C2-C30)alkenyl, a (C2-C30)alkynyl, a cyano, a carbazolyl, a di(C1-C30)alkylamino, a di(C6-C30)arylamino unsubstituted or substituted with a (C1-C30)alkyl, a (C1-C30)alkyl(C6-C30)arylamino, a di(C6-C30)arylboronyl, a di(C1-C30)alkylboronyl, a (C1-C30)alkyl(C6-C30)arylboronyl, a (C6-C30)aryl(C1-C30)alkyl, a (C1-C30)alkyl(C6-C30)aryl, a carboxyl, a nitro and a hydroxyl.
  3. The organic electroluminescence compound according to claim 1, wherein the moiety,
    Figure PCTKR2013009197-appb-I000060
    is selected from the group consisting of the following structures:
    Figure PCTKR2013009197-appb-I000061
    wherein X, Y, R and a are as defined in claim 1.
  4. The organic electroluminescence compound according to claim 1, wherein L1 represents a single bond, a substituted or unsubstituted (C6-C21)arylene group, or a substituted or unsubstituted 5- to 21-memebered heteroarylene group;
    Ar1 represents a substituted or unsubstituted (C6-C21)aryl group, or a substituted or unsubstituted 5- to 21-membered heteroaryl group;
    Ar2 and Ar3 each independently represent hydrogen, a substituted or unsubstituted (C6-C21)aryl group, a substituted or unsubstituted 5- to 21-membered heteroaryl group, or -NR1R2;
    R1 and R2 each independently represent hydrogen, or a substituted or unsubstituted (C6-C21)aryl group;
    X and Y each independently represent -O-, -S-, -N(R21)- or -C(R22)(R23)-; where X is -C(R22)(R23)-, Y is -O-, -S- or -N(R21)-, where X is -O- or -S-, Y is -N(R21)- or -C(R22)(R23)-, and where X is -N(R21)-, Y is -O-, -S- or -C(R22)(R23)-;
    R represents hydrogen: and
    R21 to R23 each independently represent a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group.
  5. The organic electroluminescence compound according to claim 1, wherein L1 represents a single bond; a (C6-C21)arylene group unsubstituted or substituted with a (C1-C6)alkyl; or an unsubstituted 5- to 21-memebered heteroarylene group;
    Ar1 represents a (C6-C21)aryl group unsubstituted or substituted with deuterium, a halogen, a (C1-C6)alkyl, a (C1-C6)alkoxy, a (C6-C21)aryl, a (C3-C21)cycloalkyl, a tri(C6-C12)arylsilyl, a cyano, a di(C6-C12)arylamino, or a hydroxyl; or a 5- to 21-memebered heteroaryl group unsubstituted or substituted with a (C6-C21)aryl;
    Ar2 and Ar3 each independently represent hydrogen; an unsubstituted (C6-C21)aryl group; an unsubstituted 5- to 21-membered heteroaryl group; or -NR1R2;
    R1 and R2 each independently represent hydrogen, or a (C6-C21)aryl group unsubstituted or substituted with a (C1-C6)alkyl;
    X and Y each independently represent -O-, -S-, -N(R21)- or -C(R22)(R23)-; where X is -C(R22)(R23)-, Y is -O-, -S- or -N(R21)-, where X is -O- or -S-, Y is -N(R21)- or -C(R22)(R23)-, and where X is -N(R21)-, Y is -O-, -S- or -C(R22)(R23)-;
    R represents hydrogen: and
    R21 to R23 each independently represent an unsubstituted (C1-C6)alkyl group, or an unsubstituted (C6-C21)aryl group.
  6. The organic electroluminescence compound according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
    Figure PCTKR2013009197-appb-I000062
    Figure PCTKR2013009197-appb-I000063
    Figure PCTKR2013009197-appb-I000064
    Figure PCTKR2013009197-appb-I000065
    Figure PCTKR2013009197-appb-I000066
    Figure PCTKR2013009197-appb-I000067
    Figure PCTKR2013009197-appb-I000068
    Figure PCTKR2013009197-appb-I000069
    Figure PCTKR2013009197-appb-I000070
    Figure PCTKR2013009197-appb-I000071
    Figure PCTKR2013009197-appb-I000072
    Figure PCTKR2013009197-appb-I000073
    Figure PCTKR2013009197-appb-I000074
    Figure PCTKR2013009197-appb-I000075
    Figure PCTKR2013009197-appb-I000076
    Figure PCTKR2013009197-appb-I000077
    Figure PCTKR2013009197-appb-I000078
    Figure PCTKR2013009197-appb-I000079
    Figure PCTKR2013009197-appb-I000080
    Figure PCTKR2013009197-appb-I000081
    Figure PCTKR2013009197-appb-I000082
    Figure PCTKR2013009197-appb-I000083
    Figure PCTKR2013009197-appb-I000084
    Figure PCTKR2013009197-appb-I000085
  7. An organic electroluminescence device comprising the organic electroluminescence compound according to claim 1.
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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014178434A1 (en) * 2013-05-02 2014-11-06 出光興産株式会社 Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
KR20140145456A (en) * 2013-06-13 2014-12-23 제일모직주식회사 Organic compound and organic optoelectric device and display device
US20160211454A1 (en) * 2015-01-20 2016-07-21 Samsung Display Co., Ltd. Organic light-emitting device
US20160308138A1 (en) * 2015-04-17 2016-10-20 Samsung Display Co., Ltd. Organic light-emitting device
US20170018723A1 (en) * 2015-07-14 2017-01-19 Sfc Co., Ltd. Organic light emitting diode for high efficiency
US20170200905A1 (en) * 2016-01-05 2017-07-13 Samsung Display Co., Ltd. Condensed cyclic compound and an organic light-emitting device including the same
US9947879B2 (en) 2013-03-15 2018-04-17 Idemitsu Kosan Co., Ltd. Anthracene derivative and organic electroluminescence element using same
CN108137525A (en) * 2016-02-23 2018-06-08 株式会社Lg化学 Heterocyclic compound and the Organic Light Emitting Diode for including it
CN108779120A (en) * 2016-03-24 2018-11-09 德山新勒克斯有限公司 Organic electronic element compound, organic electronic element and its electronic device using the compound
JP2018534238A (en) * 2016-02-23 2018-11-22 エルジー・ケム・リミテッド Heterocyclic compound and organic light emitting device including the same
US10230056B2 (en) 2015-08-27 2019-03-12 Lg Chem, Ltd. Heterocyclic compound and organic light emitting element comprising same
US10312449B2 (en) 2015-05-27 2019-06-04 Samsung Display Co., Ltd. Organic light-emitting device
CN110023305A (en) * 2016-11-21 2019-07-16 株式会社斗山 Organic luminescent compounds and the organic electroluminescent device for utilizing it
US10367147B2 (en) 2015-05-27 2019-07-30 Samsung Display Co., Ltd. Organic light-emitting device
CN110330472A (en) * 2019-07-10 2019-10-15 吉林奥来德光电材料股份有限公司 A kind of blue light material and its preparation method and application

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102436175B1 (en) * 2014-05-09 2022-08-26 에스에프씨주식회사 Novel aromatic compounds for organic light-emitting diode and organic light-emitting diode including the same
CN104892487B (en) * 2015-05-29 2017-11-24 上海道亦化工科技有限公司 A kind of anthracene class organic electroluminescent compounds and its organic electroluminescence device
KR101946020B1 (en) * 2015-09-10 2019-02-08 엘티소재주식회사 Hetero-cyclic compound and organic light emitting device using the same
US11367838B2 (en) 2017-06-16 2022-06-21 Lg Chem, Ltd. Anthracene derivative and organic light-emitting device comprising same
KR102130214B1 (en) * 2017-10-16 2020-07-06 주식회사 엘지화학 Anthracene derivative and organic light emitting device comprising the same
KR102484034B1 (en) * 2020-01-20 2023-01-04 주식회사 엘지화학 Polycyclic compound and organic light emitting device comprising same
KR102519269B1 (en) * 2020-01-20 2023-04-10 주식회사 엘지화학 Polycyclic compound and organic light emitting device comprising same
KR102605832B1 (en) * 2020-01-20 2023-11-27 주식회사 엘지화학 Compound and organic light emitting device comprising same

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2141214A2 (en) * 2008-06-25 2010-01-06 Gracel Display Inc. Novel organic electroluminescent compounds and organic electroluminescent device using the same
EP2189508A2 (en) * 2008-11-21 2010-05-26 Gracel Display Inc. Electroluminescent device using electroluminescent compounds
WO2010114243A2 (en) * 2009-03-31 2010-10-07 Dow Advanced Display Materials,Ltd. Novel compounds for organic electronic material and organic electronic device using the same
WO2010114263A2 (en) * 2009-03-31 2010-10-07 Dow Advanced Display Materials,Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
WO2010114256A2 (en) * 2009-03-31 2010-10-07 Dow Advanced Display Materials,Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
WO2010114266A2 (en) * 2009-03-31 2010-10-07 Dow Advanced Display Materials,Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
WO2010137285A1 (en) * 2009-05-29 2010-12-02 出光興産株式会社 Anthracene derivative and organic electroluminescent element using the same
WO2011115378A1 (en) * 2010-03-17 2011-09-22 Rohm And Haas Electronic Materials Korea Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
US20120097932A1 (en) * 2010-10-25 2012-04-26 Samsung Mobile Display Co., Ltd. Condensed-cyclic compound, organic light-emitting diode comprising the same and flat panel display device comprising the organic light-emitting diode
KR20120120886A (en) * 2011-04-25 2012-11-02 (주)씨에스엘쏠라 Organic light compound and organic light device using the same
CN103187531A (en) * 2011-12-30 2013-07-03 昆山维信诺显示技术有限公司 Organic light-emitting device and purpose of double-polarity organic compound
KR20130098228A (en) * 2012-02-27 2013-09-04 주식회사 엘지화학 Organic light emitting diode

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2141214A2 (en) * 2008-06-25 2010-01-06 Gracel Display Inc. Novel organic electroluminescent compounds and organic electroluminescent device using the same
EP2189508A2 (en) * 2008-11-21 2010-05-26 Gracel Display Inc. Electroluminescent device using electroluminescent compounds
WO2010114243A2 (en) * 2009-03-31 2010-10-07 Dow Advanced Display Materials,Ltd. Novel compounds for organic electronic material and organic electronic device using the same
WO2010114263A2 (en) * 2009-03-31 2010-10-07 Dow Advanced Display Materials,Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
WO2010114256A2 (en) * 2009-03-31 2010-10-07 Dow Advanced Display Materials,Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
WO2010114266A2 (en) * 2009-03-31 2010-10-07 Dow Advanced Display Materials,Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
WO2010137285A1 (en) * 2009-05-29 2010-12-02 出光興産株式会社 Anthracene derivative and organic electroluminescent element using the same
WO2011115378A1 (en) * 2010-03-17 2011-09-22 Rohm And Haas Electronic Materials Korea Ltd. Novel organic electroluminescent compounds and organic electroluminescent device using the same
US20120097932A1 (en) * 2010-10-25 2012-04-26 Samsung Mobile Display Co., Ltd. Condensed-cyclic compound, organic light-emitting diode comprising the same and flat panel display device comprising the organic light-emitting diode
KR20120120886A (en) * 2011-04-25 2012-11-02 (주)씨에스엘쏠라 Organic light compound and organic light device using the same
CN103187531A (en) * 2011-12-30 2013-07-03 昆山维信诺显示技术有限公司 Organic light-emitting device and purpose of double-polarity organic compound
KR20130098228A (en) * 2012-02-27 2013-09-04 주식회사 엘지화학 Organic light emitting diode

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9947879B2 (en) 2013-03-15 2018-04-17 Idemitsu Kosan Co., Ltd. Anthracene derivative and organic electroluminescence element using same
WO2014178434A1 (en) * 2013-05-02 2014-11-06 出光興産株式会社 Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
JPWO2014178434A1 (en) * 2013-05-02 2017-02-23 出光興産株式会社 COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENT ELEMENT, ORGANIC ELECTROLUMINESCENT ELEMENT AND ELECTRONIC DEVICE
KR20140145456A (en) * 2013-06-13 2014-12-23 제일모직주식회사 Organic compound and organic optoelectric device and display device
KR101627755B1 (en) 2013-06-13 2016-06-07 제일모직 주식회사 Organic compound and organic optoelectric device and display device
US9653690B2 (en) 2013-06-13 2017-05-16 Samsung Sdi Co., Ltd. Organic compound, organic optoelectronic device and display device
US20160211454A1 (en) * 2015-01-20 2016-07-21 Samsung Display Co., Ltd. Organic light-emitting device
CN105810838A (en) * 2015-01-20 2016-07-27 三星显示有限公司 Organic light-emitting device
EP3048654B1 (en) * 2015-01-20 2022-11-09 Samsung Display Co., Ltd. Organic light-emitting device
US20160308138A1 (en) * 2015-04-17 2016-10-20 Samsung Display Co., Ltd. Organic light-emitting device
US11322705B2 (en) * 2015-04-17 2022-05-03 Samsung Display Co., Ltd. Organic light-emitting device
US10312449B2 (en) 2015-05-27 2019-06-04 Samsung Display Co., Ltd. Organic light-emitting device
US10367147B2 (en) 2015-05-27 2019-07-30 Samsung Display Co., Ltd. Organic light-emitting device
US20170018723A1 (en) * 2015-07-14 2017-01-19 Sfc Co., Ltd. Organic light emitting diode for high efficiency
US10998505B2 (en) * 2015-07-14 2021-05-04 Sfc Co., Ltd. Organic light emitting diode for high efficiency
US10230056B2 (en) 2015-08-27 2019-03-12 Lg Chem, Ltd. Heterocyclic compound and organic light emitting element comprising same
US10580999B2 (en) 2016-01-05 2020-03-03 Samsung Display Co., Ltd. Condensed cyclic compound and an organic light-emitting device including the same
US20170200905A1 (en) * 2016-01-05 2017-07-13 Samsung Display Co., Ltd. Condensed cyclic compound and an organic light-emitting device including the same
US11276827B2 (en) 2016-01-05 2022-03-15 Samsung Display Co., Ltd. Condensed cyclic compound and an organic light-emitting device including the same
US11107999B2 (en) 2016-01-05 2021-08-31 Samsung Display Co., Ltd. Condensed cyclic compound and an organic light-emitting device including the same
US10553800B2 (en) 2016-01-05 2020-02-04 Samsung Display Co., Ltd. Condensed cyclic compound and an organic light-emitting device including the same
US10873035B2 (en) 2016-02-23 2020-12-22 Lg Chem, Ltd. Heterocyclic compound and organic light emitting diode containing same
CN108137525B (en) * 2016-02-23 2021-12-28 株式会社Lg化学 Heterocyclic compound and organic light emitting diode including the same
CN108137525A (en) * 2016-02-23 2018-06-08 株式会社Lg化学 Heterocyclic compound and the Organic Light Emitting Diode for including it
US20180351111A1 (en) * 2016-02-23 2018-12-06 Lg Chem, Ltd. Heterocyclic compound and organic light emitting diode containing same
JP2018534238A (en) * 2016-02-23 2018-11-22 エルジー・ケム・リミテッド Heterocyclic compound and organic light emitting device including the same
US11968897B2 (en) 2016-02-23 2024-04-23 Lg Chem, Ltd. Heterocyclic compound and organic light emitting diode containing same
CN108779120A (en) * 2016-03-24 2018-11-09 德山新勒克斯有限公司 Organic electronic element compound, organic electronic element and its electronic device using the compound
US10995069B2 (en) 2016-03-24 2021-05-04 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element using same, and electronic device comprising same
CN110023305A (en) * 2016-11-21 2019-07-16 株式会社斗山 Organic luminescent compounds and the organic electroluminescent device for utilizing it
CN110023305B (en) * 2016-11-21 2022-08-09 索路思高新材料有限公司 Organic light-emitting compound and organic electroluminescent element using same
US11667622B2 (en) 2016-11-21 2023-06-06 Solus Advanced Materials Co., Ltd. Organic light emitting compound and organic electroluminescence device using same
CN110330472A (en) * 2019-07-10 2019-10-15 吉林奥来德光电材料股份有限公司 A kind of blue light material and its preparation method and application

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