WO2014061961A1 - 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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WO2014061961A1
WO2014061961A1 PCT/KR2013/009195 KR2013009195W WO2014061961A1 WO 2014061961 A1 WO2014061961 A1 WO 2014061961A1 KR 2013009195 W KR2013009195 W KR 2013009195W WO 2014061961 A1 WO2014061961 A1 WO 2014061961A1
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unsubstituted
substituted
group
aryl
alkyl
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PCT/KR2013/009195
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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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Priority to CN201380053644.0A priority Critical patent/CN104854089A/en
Publication of WO2014061961A1 publication Critical patent/WO2014061961A1/en

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    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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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.
  • the present inventors found that a specific structure of an anthracene derivative is suitable for a fluorescent host material of a light-emitting layer.
  • 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, a substituted or unsubstituted (C1-C30)alkyl(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;
  • Y represents -O-, -S-, -N(R 21 )- or -C(R 22 )(R 23 )-; where Y is -S-, L 1 is not a single bond;
  • 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; where L 1 is an arylene, R 22 and R 23 are not simultaneously aryl, nor R 22 and R 23 are not linked to each other to form a ring; and
  • a 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 alkylaryl, 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)cycloal
  • 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 a (C6-C21)aryl; or a 5- to 21-memebered heteroarylene group unsubstituted or substituted with a (C6-C21)aryl.
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (C1-C30)alkyl(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, a substituted or unsubstituted (C1-C6)alkyl(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 5- to 21-membered heteroaryl, a (C3-C21
  • 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; a (C6-C21)aryl group unsubstituted or substituted with a (C1-C6)alkyl; 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.
  • Y represents -O-, -S-, -N(R 21 )- or -C(R 22 )(R 23 )-; where Y is -S-, L 1 is not a single bond.
  • 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, preferably represents hydrogen, or a substituted or unsubstituted (C6-C21)aryl group, and more preferably represents hydrogen or an unsubstituted (C6-C21)aryl 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; where L 1 is an arylene, R 22 and R 23 are not simultaneously aryl, nor R 22 and R 23 are not linked to each other to form a ring, preferably each independently represent a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group; where L 1 is an arylene, R 22 and R
  • 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, a substituted or unsubstituted (C1-C6)alkyl(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;
  • Y represents -O-, -S
  • L 1 represents a single bond; a (C6-C21)arylene group unsubstituted or substituted with a (C1-C6)alkyl or a (C6-C21)aryl; or a 5- to 21-memebered heteroarylene group unsubstituted or substituted with a (C6-C21)aryl;
  • 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 5- to 21-memebered heteroarylene, a (C3-C21)cycloalkyl, a tri(C6-C12)arylsilyl, a cyano, or a di(C6-C12)arylamino; a (C1-C6)alkyl(C6
  • 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 , R, a, 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-128 according to the present invention was introduced into one cell of the vacuum vapor depositing apparatus, as a host material, and compound D-9 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 650 cd/m 2 and a current density of 22.4 mA/cm 2 .
  • An OLED device was produced in the same manner as in Device Example 1, except for using compound H-175 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 1250 cd/m 2 and a current density of 19.8 mA/cm 2 .
  • An OLED device was produced in the same manner as in Device Example 1, except for using compound H-179 as a host, and using compound D-55 as a dopant of the light emitting material.
  • the produced OLED device showed a blue emission having a luminance of 660 cd/m 2 and a current density of 20.0 mA/cm 2 .
  • An OLED device was produced in the same manner as in Device Example 1, except for using compound H-174 as a host, and using compound D-56 as a dopant of the light emitting material.
  • the produced OLED device showed a blue emission having a luminance of 605 cd/m 2 and a current density of 17.3 mA/cm 2 .
  • organic electroluminescent compound according to the present invention is used as a fluorescent host of a light-emitting layer, and is efficient for blue emission.

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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 Appln. Laying-Open Nos. KR 10-2011-0002156 A, KR 10-2011-0058243 A, KR 10-2011-0058245 A, KR 10-2011-0058246 A, KR 10-2011-0058248 A, KR 10-2012-0038402 A, etc., disclose many anthracene derivatives. However, there are no disclosures of using them as a fluorescent host material of a light-emitting layer.
The present inventors found that a specific structure of an anthracene derivative is suitable for a fluorescent host material of a light-emitting layer.
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 PCTKR2013009195-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, a substituted or unsubstituted (C1-C30)alkyl(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 PCTKR2013009195-appb-I000002
Figure PCTKR2013009195-appb-I000003
Y represents -O-, -S-, -N(R21)- or -C(R22)(R23)-; where Y is -S-, L1 is not a single bond;
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; where L1 is an arylene, R22 and R23 are not simultaneously aryl, nor R22 and R23 are not linked to each other to form a ring; 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 alkylaryl, 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 (C1-C6)alkyl(C6-C21)aryl; a 5- to 21membered heteroaryl; a (C3-C21)cycloalkyl; a tri(C6-C12)arylsilyl; a cyano; and a di(C6-C12)arylamino unsubstituted or substituted with a (C1-C6)alkyl.
In formula 1, the moiety,
Figure PCTKR2013009195-appb-I000004
is preferably selected from the group consisting of the following structures:
Figure PCTKR2013009195-appb-I000005
wherein 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 a (C6-C21)aryl; or a 5- to 21-memebered heteroarylene group unsubstituted or substituted with a (C6-C21)aryl.
Ar1 represents a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted (C1-C30)alkyl(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, a substituted or unsubstituted (C1-C6)alkyl(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 5- to 21-membered heteroaryl, a (C3-C21)cycloalkyl, a tri(C6-C12)arylsilyl, a cyano, or a di(C6-C12)arylamino; a (C1-C6)alkyl(C6-C21)aryl group unsubstituted or substituted with a (C6-C21)aryl; 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; a (C6-C21)aryl group unsubstituted or substituted with a (C1-C6)alkyl; 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.
Y represents -O-, -S-, -N(R21)- or -C(R22)(R23)-; where Y is -S-, L1 is not a single bond.
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, preferably represents hydrogen, or a substituted or unsubstituted (C6-C21)aryl group, and more preferably represents hydrogen or an unsubstituted (C6-C21)aryl 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; where L1 is an arylene, R22 and R23 are not simultaneously aryl, nor R22 and R23 are not linked to each other to form a ring, preferably each independently represent a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group; where L1 is an arylene, R22 and R23 are not simultaneously aryl, nor R22 and R23 are not linked to each other to form a ring, and more preferably each independently represent an unsubstituted (C1-C6)alkyl group, or an unsubstituted (C6-C21)aryl group; where L1 is an arylene, R22 and R23 are not simultaneously aryl, nor R22 and R23 are not linked to each other to form a ring.
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, a substituted or unsubstituted (C1-C6)alkyl(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; Y represents -O-, -S-, -N(R21)- or -C(R22)(R23)-; where Y is -S-, L1 is not a single bond; R represents hydrogen, or a substituted or unsubstituted (C6-C21)aryl group: and R21 to R23 each independently represent a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group; where L1 is an arylene, R22 and R23 are not simultaneously aryl, nor R22 and R23 are not linked to each other to form a ring.
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 a (C6-C21)aryl; or a 5- to 21-memebered heteroarylene group unsubstituted or substituted with a (C6-C21)aryl; 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 5- to 21-memebered heteroarylene, a (C3-C21)cycloalkyl, a tri(C6-C12)arylsilyl, a cyano, or a di(C6-C12)arylamino; a (C1-C6)alkyl(C6-C21)aryl group unsubstituted or substituted with a (C6-C21)aryl; or a 5- to 21-memebered heteroaryl group unsubstituted or substituted with a (C6-C21)aryl; Ar2 and Ar3 each independently represent hydrogen; a (C6-C21)aryl group unsubstituted or substituted with a (C1-C6)alkyl; 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; Y represents -O-, -S-, -N(R21)- or -C(R22)(R23)-; where Y is -S-, L1 is not a single bond; R represents hydrogen or an unsubstituted (C6-C21)aryl group: and R21 to R23 each independently represent an unsubstituted (C1-C6)alkyl group, or an unsubstituted (C6-C21)aryl group; where L1 is an arylene, R22 and R23 are not simultaneously aryl, nor R22 and R23 are not linked to each other to form a ring.
The representative compounds of formula 1 include the following compounds, but are not limited thereto:
Figure PCTKR2013009195-appb-I000006
Figure PCTKR2013009195-appb-I000007
Figure PCTKR2013009195-appb-I000008
Figure PCTKR2013009195-appb-I000009
Figure PCTKR2013009195-appb-I000010
Figure PCTKR2013009195-appb-I000011
Figure PCTKR2013009195-appb-I000012
Figure PCTKR2013009195-appb-I000013
Figure PCTKR2013009195-appb-I000014
Figure PCTKR2013009195-appb-I000015
Figure PCTKR2013009195-appb-I000016
Figure PCTKR2013009195-appb-I000017
Figure PCTKR2013009195-appb-I000018
Figure PCTKR2013009195-appb-I000019
Figure PCTKR2013009195-appb-I000020
Figure PCTKR2013009195-appb-I000021
Figure PCTKR2013009195-appb-I000022
Figure PCTKR2013009195-appb-I000023
Figure PCTKR2013009195-appb-I000024
Figure PCTKR2013009195-appb-I000025
Figure PCTKR2013009195-appb-I000026
Figure PCTKR2013009195-appb-I000027
Figure PCTKR2013009195-appb-I000028
Figure PCTKR2013009195-appb-I000029
Figure PCTKR2013009195-appb-I000030
Figure PCTKR2013009195-appb-I000031
Figure PCTKR2013009195-appb-I000032
Figure PCTKR2013009195-appb-I000033
Figure PCTKR2013009195-appb-I000034
Figure PCTKR2013009195-appb-I000035
Figure PCTKR2013009195-appb-I000036
Figure PCTKR2013009195-appb-I000037
Figure PCTKR2013009195-appb-I000038
Figure PCTKR2013009195-appb-I000039
Figure PCTKR2013009195-appb-I000040
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 PCTKR2013009195-appb-I000041
[Reaction Scheme 2]
Figure PCTKR2013009195-appb-I000042
wherein Ar1, Ar2, Ar3, L1, R, a, 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 PCTKR2013009195-appb-I000043
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 PCTKR2013009195-appb-I000044
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 PCTKR2013009195-appb-I000045
Figure PCTKR2013009195-appb-I000046
Figure PCTKR2013009195-appb-I000047
Figure PCTKR2013009195-appb-I000048
Figure PCTKR2013009195-appb-I000049
Figure PCTKR2013009195-appb-I000050
Figure PCTKR2013009195-appb-I000051
Figure PCTKR2013009195-appb-I000052
Figure PCTKR2013009195-appb-I000053
Figure PCTKR2013009195-appb-I000054
Figure PCTKR2013009195-appb-I000055
Figure PCTKR2013009195-appb-I000056
Figure PCTKR2013009195-appb-I000057
Figure PCTKR2013009195-appb-I000058
Figure PCTKR2013009195-appb-I000059
Figure PCTKR2013009195-appb-I000060
Figure PCTKR2013009195-appb-I000061
Figure PCTKR2013009195-appb-I000062
Figure PCTKR2013009195-appb-I000063
Figure PCTKR2013009195-appb-I000064
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-1
Figure PCTKR2013009195-appb-I000065
After mixing compound A 4.5 g (0.016 mol), 9-bromo-10-phenylanthracene 6.3 g (0.019 mol), CuI 1.5 g (0.008 mol), K3PO4 10.4 g (0.049 mol), ethylenediamine (EDA) 1.1 mL (0.016 mol), and toluene 150 mL, the mixture was heated to 120°C, and stirred for 12 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-1, 4.0 g (46.5%).
Melting point 307°C, UV 268 nm (in methylene chloride (MC)), PL 420 nm (in MC), Molecular weight 535.68
Example 2: Preparation of compound H-128
Figure PCTKR2013009195-appb-I000066
After adding compound B 7 g (15.9 mmol), 10-phenylanthracen-9-yl boronic acid 2.3 g (8.6 mmol), Pd(PPh3)4 568 mg (0.5 mmol), and Na2CO3 5.1 g (47.91 mmol) to a mixture solvent of toluene 150 mL, ethanol 50 mL, and H2O 50 mL, the mixture was stirred at 120°C for 4 hours. After the reaction was completed, the mixture was cooled slowly to room temperature, water was added, and extracted with EA. Next, the organic layer was dried with Na2SO4, and the remaining product was concentrated, and separated using a column to obtain compound H-128, 4.9 g (50%).
Melting point 324°C, UV 258 nm (in MC), PL 431 nm (in MC), Molecular weight 611.26
Example 3: Preparation of compound H-174
Figure PCTKR2013009195-appb-I000067
Compound H-174, 3.2 g (28.5%) was prepared in the same manner as the synthetic method of compound H-128 using compound C 8 g (18.6 mmol), and 10-phenylanthracen-9-yl boronic acid 5.1 g (22.4 mmol).
Melting point 272°C, UV 305 nm (in MC), PL 412 nm (in MC), Molecular weight 601.19
Example 4: Preparation of compound H-175
Figure PCTKR2013009195-appb-I000068
Compound H-175, 6 g (70%) was prepared in the same manner as the synthetic method of compound H-128 using compound D 6 g (15 mmol), and 10-phenylanthracen-9-yl boronic acid 4.45 g (16 mmol).
Melting point 313°C, UV 352 nm (in toluene), PL 420 nm (in toluene), Molecular weight 585.21
Example 5: Preparation of compound H-179
Figure PCTKR2013009195-appb-I000069
Compound H-179, 3.7 g (54%) was prepared in the same manner as the synthetic method of compound H-128 using compound E 5.1 g (10.1 mmol), and 10-phenylanthracen-9-yl boronic acid 2.9 g (10.6 mmol).
Melting point 318°C, UV 296 nm (in MC), PL 419 nm (in MC), Molecular weight 677.22
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-128 according to the present invention was introduced into one cell of the vacuum vapor depositing apparatus, as a host material, and compound D-9 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 650 cd/m2 and a current density of 22.4 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-175 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 1250 cd/m2 and a current density of 19.8 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-179 as a host, and using compound D-55 as a dopant of the light emitting material.
The produced OLED device showed a blue emission having a luminance of 660 cd/m2 and a current density of 20.0 mA/cm2.
Device Example 4: 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-174 as a host, and using compound D-56 as a dopant of the light emitting material.
The produced OLED device showed a blue emission having a luminance of 605 cd/m2 and a current density of 17.3 mA/cm2.
It is verified that the organic electroluminescent compound according to the present invention is used as a fluorescent host of a light-emitting layer, and is efficient for blue emission.

Claims (7)

  1. An organic electroluminescence compound represented by the following formula 1:
    Figure PCTKR2013009195-appb-I000070
    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, a substituted or unsubstituted (C1-C30)alkyl(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 PCTKR2013009195-appb-I000071
    Figure PCTKR2013009195-appb-I000072
    Y represents -O-, -S-, -N(R21)- or -C(R22)(R23)-; where Y is -S-, L1 is not a single bond;
    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; where L1 is an arylene, R22 and R23 are not simultaneously aryl, nor R22 and R23 are not linked to each other to form a ring; 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 alkylaryl, 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 PCTKR2013009195-appb-I000073
    is selected from the group consisting of the following structures:
    Figure PCTKR2013009195-appb-I000074
    wherein 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, a substituted or unsubstituted (C1-C6)alkyl(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;
    Y represents -O-, -S-, -N(R21)- or -C(R22)(R23)-; where Y is -S-, L1 is not a single bond;
    R represents hydrogen, or a substituted or unsubstituted (C6-C21)aryl group: and
    R21 to R23 each independently represent a substituted or unsubstituted (C1-C6)alkyl group, or a substituted or unsubstituted (C6-C21)aryl group; where L1 is an arylene, R22 and R23 are not simultaneously aryl, nor R22 and R23 are not linked to each other to form a ring.
  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 a (C6-C21)aryl; or a 5- to 21-memebered heteroarylene group unsubstituted or substituted with a (C6-C21)aryl;
    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 5- to 21-memebered heteroarylene, a (C3-C21)cycloalkyl, a tri(C6-C12)arylsilyl, a cyano, or a di(C6-C12)arylamino; a (C1-C6)alkyl(C6-C21)aryl group unsubstituted or substituted with a (C6-C21)aryl; or a 5- to 21-memebered heteroaryl group unsubstituted or substituted with a (C6-C21)aryl;
    Ar2 and Ar3 each independently represent hydrogen; a (C6-C21)aryl group unsubstituted or substituted with a (C1-C6)alkyl; 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;
    Y represents -O-, -S-, -N(R21)- or -C(R22)(R23)-; where Y is -S-, L1 is not a single bond;
    R represents hydrogen or an unsubstituted (C6-C21)aryl group: and
    R21 to R23 each independently represent an unsubstituted (C1-C6)alkyl group, or an unsubstituted (C6-C21)aryl group; where L1 is an arylene, R22 and R23 are not simultaneously aryl, nor R22 and R23 are not linked to each other to form a ring.
  6. The organic electroluminescence compound according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
    Figure PCTKR2013009195-appb-I000075
    Figure PCTKR2013009195-appb-I000076
    Figure PCTKR2013009195-appb-I000077
    Figure PCTKR2013009195-appb-I000078
    Figure PCTKR2013009195-appb-I000079
    Figure PCTKR2013009195-appb-I000080
    Figure PCTKR2013009195-appb-I000081
    Figure PCTKR2013009195-appb-I000082
    Figure PCTKR2013009195-appb-I000083
    Figure PCTKR2013009195-appb-I000084
    Figure PCTKR2013009195-appb-I000085
    Figure PCTKR2013009195-appb-I000086
    Figure PCTKR2013009195-appb-I000087
    Figure PCTKR2013009195-appb-I000088
    Figure PCTKR2013009195-appb-I000089
    Figure PCTKR2013009195-appb-I000090
    Figure PCTKR2013009195-appb-I000091
    Figure PCTKR2013009195-appb-I000092
    Figure PCTKR2013009195-appb-I000093
    Figure PCTKR2013009195-appb-I000094
    Figure PCTKR2013009195-appb-I000095
    Figure PCTKR2013009195-appb-I000096
    Figure PCTKR2013009195-appb-I000097
    Figure PCTKR2013009195-appb-I000098
    Figure PCTKR2013009195-appb-I000099
    Figure PCTKR2013009195-appb-I000100
    Figure PCTKR2013009195-appb-I000101
    Figure PCTKR2013009195-appb-I000102
    Figure PCTKR2013009195-appb-I000103
    Figure PCTKR2013009195-appb-I000104
    Figure PCTKR2013009195-appb-I000105
    Figure PCTKR2013009195-appb-I000106
    Figure PCTKR2013009195-appb-I000107
    Figure PCTKR2013009195-appb-I000108
    Figure PCTKR2013009195-appb-I000109
  7. An organic electroluminescence device comprising the organic electroluminescence compound according to claim 1.
PCT/KR2013/009195 2012-10-16 2013-10-15 Organic electroluminescence compounds and organic electroluminescence device comprising the same WO2014061961A1 (en)

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