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WO2013032278A1 - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDF

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Publication number
WO2013032278A1
WO2013032278A1 PCT/KR2012/007001 KR2012007001W WO2013032278A1 WO 2013032278 A1 WO2013032278 A1 WO 2013032278A1 KR 2012007001 W KR2012007001 W KR 2012007001W WO 2013032278 A1 WO2013032278 A1 WO 2013032278A1
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Prior art keywords
group
substituted
unsubstituted
alkyl
aryl
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PCT/KR2012/007001
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French (fr)
Inventor
Hee-Sook Kim
Hong-Yoep NA
Jong-seok KU
Hyuck-Joo Kwon
Kyung-Joo Lee
Bong-Ok Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority to CN201280049556.9A priority Critical patent/CN103857673A/en
Priority to JP2014528286A priority patent/JP2014531419A/en
Publication of WO2013032278A1 publication Critical patent/WO2013032278A1/en

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    • H—ELECTRICITY
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    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/30—Coordination compounds
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    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • H10K2101/10—Triplet emission

Definitions

  • the present invention relates to novel organic electroluminescent compounds and organic electroluminescent device using the same.
  • An electroluminescent (EL) device is a self-light-emitting device which has advantages over other types of display devices in that it provides a wider viewing angle, a greater contrast ratio, and has a faster response time.
  • An organic EL device was first developed by Eastman Kodak, by using small molecules which are aromatic diamines, and aluminum complexes as a material for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato- N,C3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red, green and blue materials, respectively.
  • phosphorescent materials are being researched in Japan, Europe and U.S.A. recently.
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • BCP bathocuproine
  • BAlq aluminum(III)bis(2-methyl-8-quinolinate) (4-phenylphenolate)
  • Japanese Patent Appln. Laying-Open No. 1999-149987 discloses a device comprising a compound in which N-carbazolyl group is bonded to a fluoranthene structure, and lublene as materials for an light-emitting layer which also functions as a hole injection and transport layer. However, the device emits yellow light. Said document also discloses a fluorescent electroluminescent device which emits green light and comprises a compound in which N-carbazolyl group is bonded to a fluoranthene structure, as a material for a hole injection and transport layer.
  • a phosphorescent electroluminescent device which emits red light and comprises a compound in which N-carbazolyl group is bonded to a fluoranthene structure, as a host material for a light-emitting layer.
  • the objective of the present invention is to provide an organic electroluminescent compound imparting high luminous efficiency and a long operation lifetime to a device, and emitting red light; and an organic electroluminescent device having high efficiency and a long lifetime, using said compound as a light-emitting material.
  • L 1 represents a single bond, a substituted or unsubstituted 3- to 30-membered heteroarylene group, or a substituted or unsubstituted (C6-C30)arylene group;
  • X represents -O-, -S-, -CR 11 R 12 - or -NR 13 -;
  • R 11 to R 13 each independently represent a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group;
  • R 1 to R 6 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group fused with at least one (C3-C30)cycloalkyl, a 5- to 7-membered heterocycloalkyl group fused with at least one substituted or unsubstituted aromatic ring, a (C3-C30)
  • R 14 to R 20 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C5-C30)alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
  • a, d and e each independently represent an integer of 1 to 4; where a, d or e is an integer of 2 or more, each of R 1 , each of R 4 and each of R 5 is the same or different;
  • b and f each independently represent an integer of 1 to 3; where b or f is an integer of 2 or more, each of R 2 and each of R 6 is the same or different;
  • c represents an integer of 1 to 5; where c is an integer of 2 or more, each of R 3 is the same or different;
  • n 1, 2 or 3;
  • the organic electroluminescent compounds according to the present invention have high efficiency in transporting electrons, crystallization could be prevented when manufacturing a device. Further, the compounds have good layer formability and improve the current characteristic of the device. Therefore, they can produce an organic electroluminescent device having lowered driving voltages and enhanced power 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 electroluminescent device comprising the material.
  • a (C1-C30)alkyl group is preferably a (C1-C20)alkyl group, more preferably a (C1-C6)alkyl group;
  • a (C6-C30)aryl group is preferably a (C6-C21)aryl group;
  • a 3- to 30-membered heteroaryl group is preferably a 3- to 21-membered heteroaryl group;
  • a (C3-C30)cycloalkyl group is preferably a (C3-C20)cycloalkyl group, more preferably a (C3-C7)cycloalkyl group
  • 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.
  • L 1 represents a single bond, a 3- to 30-membered heteroarylene group or a (C6-C30)arylene group
  • X represents -O-, -S-, -CR 11 R 12 - or -NR 13 -
  • R 11 to R 13 each independently represent a (C1-C30)alkyl group, a (C6-C30)aryl group, or a 3- to 30-membered heteroaryl group
  • R 1 to R 6 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group, a (C6-C30)aryl group, a 3- to 30-membered heteroaryl group, or a carbazolyl group
  • m represents 1 or 2
  • the heteroarylene and arylene groups in L 1 , the alkyl, aryl, heteroaryl and carbazolyl groups in R 1 to R 6 and R 11 to R 13 can be substituted with at least one
  • L 1 represents a single bond, a phenylene, a naphthylene, a biphenylene, a terphenylene, an anthrylene, an indenylene, a fluorenylene, a phenanthrylene, a triphenylenylene, a pyrenylene, a perylenylene, a crysenylene, a naphthacenylene, a fluoranthenylene, a phenylene-naphthylene, a furylene, a thiophenylene, a pyrrolylene, an imidazolylene, a pyrazolylene, a thiazolylene, a thiadiazolylene, an isothiazolylene, an isoxazolylene, an oxazolylene, an oxadiazolylene, a triazinylene, a tetrazinylene, a triazolylene, a fur
  • L 1 is preferably a single bond, or a substituted or unsubstituted (C6-C21)arylene group, more preferably a single bond, or a (C6-C21)arylene group unsubstituted or substituted with a (C1-C6)alkyl group.
  • R 1 to R 6 each independently are preferably hydrogen; a halogen; a substituted or unsubstituted (C6-C21)aryl group; a substituted or unsubstituted 3- to 21-membered heteroaryl group, more preferably hydrogen; a halogen; a (C6-C21)aryl group unsubstituted or substituted with a halogen, deuterium, a (C1-C6)alkyl group, a (C6-C21)aryl group, a 3- to 21-membered heteroaryl group or a tri(C6-C12)arylsilyl group; or an unsubstituted 3- to 21-membered heteroaryl group.
  • R 11 to R 13 each independently are preferably a substituted or unsubstituted (C1-C6)alkyl group; a substituted or unsubstituted (C6-C21)aryl group; or a substituted or unsubstituted 3- to 21-membered heteroaryl group, more preferably an unsubstituted (C1-C6)alkyl group; a (C6-C21)aryl group unsubstituted or substituted with a halogen, deuterium or a (C1-C6)alkyl group; or a 3- to 21-membered heteroaryl group substituted with a (C6-C21)aryl group.
  • the representative compounds of the present invention include the following compounds:
  • organic electroluminescent compounds according to the present invention can be prepared according to the following reaction scheme.
  • L 1 , Z, R 1 to R 4 , m, a, b, c and d 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.
  • the above material can be comprised of the organic electroluminescent compound according to the present invention alone, or can further include conventional materials generally used 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 comprises at least one compound of formula 1 according to the present invention.
  • said organic layer comprises a light-emitting layer in which the organic electroluminescent compound of formula 1 is comprised as a host material.
  • the organic electroluminescent compound of formula 1 When the organic electroluminescent compound of formula 1 is used as a host material in the light-emitting layer, one or more phosphorescent dopant can be used together.
  • the phosphorescent dopant applied to the electroluminescent device according to the present invention is not limited, but preferably may be selected from compounds represented by the following formula 2:
  • M 1 is selected from the group consisting of Ir, Pt, Pd and Os;
  • L 101 , L 102 and L 103 are each independently selected from the following structures:
  • R 201 to R 203 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a (C6-C30)aryl group unsubstituted or substituted with (C1-C30)alkyl group(s), or a halogen;
  • R 204 to R 219 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, SF 5 , a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)aryl
  • R 220 to R 223 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), or a (C6-C30)aryl group unsubstituted or substituted with (C1-C30)alkyl group(s);
  • R 224 and R 225 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a halogen, or R 224 and R 225 are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C5-C30)alicyclic or aromatic ring;
  • R 226 represents a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group or a halogen;
  • R 227 to R 229 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group or a halogen;
  • R 231 to R 242 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a (C1-C30)alkoxy group, a halogen, a substituted or unsubstituted (C6-C30)aryl group, a cyano group, or a substituted or unsubstituted (C5-C30)cycloalkyl group, or each of R 231 to R 242 may be linked to an adjacent substituent via alkylene group or alkenylene group to form a spiro ring or a fused ring or may be linked to R 207 or R 208 via alkylene group or alkenylene group to form a saturated or unsaturated fused ring.
  • the dopants of formula 2 include the following, but are not limited thereto:
  • the organic electroluminescent device according to the present invention may further comprise, in addition to the organic electroluminescent compounds 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 comprise a light-emitting layer and a charge generating layer.
  • the organic electroluminescent device may emit white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound, besides the organic electroluminescent compound according to the present invention.
  • a surface layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s).
  • a chalcogenide(includes oxides) layer of silicon or aluminum is placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or metal oxide layer is 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 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.
  • An OLED device was produced using the compound 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. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • N 1 ,N 1’ -([1,1’-biphenyl]-4,4’-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4 -diphenylbenzene-1,4-diamine) 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’-di(4-biphenyl)-N,N’-di(4-biphenyl)-4,4’-diaminobiphenyl was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • compound C-42 was introduced into one cell of the vacuum vapor depositing apparatus, as a host material
  • compound D-7 was introduced into another cell as a dopant.
  • the two materials were evaporated at different rates and were deposited in a doping amount of 4 wt% of the dopant 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. Then, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole was introduced into one cell and lithium quinolate was introduced into another cell. The two materials were evaporated at the same rate and were deposited in a doping amount of 50 wt%, respectively to form an electron transport layer having a thickness of 30nm 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 red emission having a luminance of 1,060 cd/m 2 and a current density of 7.7 mA/cm 2 at a driving voltage of 3.9 V. Further, the time taken to be reduced to 90 % of the luminance at a luminance of 5,000 nit was at least 130 hours.
  • An OLED device was produced in the same manner as in Device Example 1, except for using compound C-35 as a host material, and compound D-7 as a dopant.
  • the produced OLED device showed red emission having a luminance of 1,020 cd/m 2 and a current density of 7.5 mA/cm 2 at a driving voltage of 3.8 V. Further, the time taken to be reduced to 90 % of the luminance at a luminance of 5,000 nit was at least 130 hours.
  • Comparative Example 1 Production of an OLED device using conventional electroluminescent compounds
  • An OLED device was produced in the same manner as in Device Example 1, except that 4,4'-N,N'-dicarbazole-biphenyl was used as a host material and compound D-11 was used as a dopant to deposit a light-emitting layer, and that a hole blocking layer having a thickness of 10 nm was deposited between the light-emitting layer and the electron transport layer by using aluminum(III)bis(2-methyl-8-quinolinato)4- phenylphenolate.
  • the produced OLED device showed red emission having a luminance of 1,000 cd/m 2 and a current density of 20.4 mA/cm 2 at a driving voltage of 8.2 V. Further, the time taken to be reduced to 90 % of the luminance at a luminance of 5,000 nit was at least 10 hours.
  • the organic electroluminescent compounds of the present invention have superior luminous characteristics than the conventional materials.
  • a device using the compounds according to the present invention as a light-emitting host material increases power efficiency by reducing the driving voltage, and has excellent light emitting efficiency and lifetime characteristic.

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Abstract

The present invention relates to a novel compound and an organic electroluminescent device containing the same. Since the compounds according to the present invention have high efficiency in transporting electrons, crystallization could be prevented when manufacturing the device, and since they are adaptable in the formation of the layers, the current characteristic of the device is improved, and finally they can manufacture an organic electroluminescent device having lowered driving voltage, advanced power efficiency, and improved light emitting efficiency and lifetime characteristic compared with devices comprising the conventional materials.

Description

NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
The present invention relates to novel organic electroluminescent compounds and organic electroluminescent device using the same.
An electroluminescent (EL) device is a self-light-emitting device which has advantages over other types of display devices in that it provides a wider viewing angle, a greater contrast ratio, and has a faster response time. An organic EL device was first developed by Eastman Kodak, by using small molecules which are aromatic diamines, and aluminum complexes as a material for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
The most important factor to determine luminous efficiency in an organic EL device is a light-emitting material. Until now, fluorescent materials have been widely used as a light-emitting material. However, in view of electroluminescent mechanisms, developing phosphorescent materials is one of the best methods to theoretically enhance the luminous efficiency by four (4) times. Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato- N,C3’)iridium(acetylacetonate) ((acac)Ir(btp)2), tris(2-phenylpyridine)iridium (Ir(ppy)3) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red, green and blue materials, respectively. Especially, many phosphorescent materials are being researched in Japan, Europe and U.S.A. recently.
Until now, 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known host material for phosphorescent substances. Further, an organic EL device using bathocuproine (BCP) and aluminum(III)bis(2-methyl-8-quinolinate) (4-phenylphenolate) (BAlq) for a hole blocking layer is known, and Pioneer (Japan) et al. developed a high performance organic EL device employing a derivative of BAlq as a host material.
Though these materials provide good light-emitting characteristics, they have the following disadvantages. Due to their low glass transition temperature and poor thermal stability, their degradation may occur during a high-temperature deposition process in a vacuum. The power efficiency of an organic EL device is given by [(π/voltage) × current efficiency], and the power efficiency is inversely proportional to voltage, and thus in order to lower the power consumption, the power efficiency should be raised. Although an organic EL device comprising phosphorescent materials provides much higher current efficiency (cd/A) than one comprising fluorescent materials, an organic EL device using conventional phosphorescent materials such as BAlq or CBP has a higher driving voltage than that using fluorescent materials. Thus, the EL device using the conventional phosphorescent materials has no advantage in terms of power efficiency (lm/W). Further, the operation lifetime of the organic EL device is short. Thus, red host materials having better properties need to be researched.
Japanese Patent Appln. Laying-Open No. 1999-149987 discloses a device comprising a compound in which N-carbazolyl group is bonded to a fluoranthene structure, and lublene as materials for an light-emitting layer which also functions as a hole injection and transport layer. However, the device emits yellow light. Said document also discloses a fluorescent electroluminescent device which emits green light and comprises a compound in which N-carbazolyl group is bonded to a fluoranthene structure, as a material for a hole injection and transport layer.
However, it does not disclose a phosphorescent electroluminescent device which emits red light and comprises a compound in which N-carbazolyl group is bonded to a fluoranthene structure, as a host material for a light-emitting layer.
The objective of the present invention is to provide an organic electroluminescent compound imparting high luminous efficiency and a long operation lifetime to a device, and emitting red light; and an organic electroluminescent device having high efficiency and a long lifetime, using said compound as a light-emitting material.
The present inventors found that the above objective can be achieved by an organic electroluminescent compound represented by the following formula 1:
Figure PCTKR2012007001-appb-I000001
wherein
Figure PCTKR2012007001-appb-I000002
L1 represents a single bond, a substituted or unsubstituted 3- to 30-membered heteroarylene group, or a substituted or unsubstituted (C6-C30)arylene group;
X represents -O-, -S-, -CR11R12- or -NR13-;
R11 to R13 each independently represent a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group;
R1 to R6 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group fused with at least one (C3-C30)cycloalkyl, a 5- to 7-membered heterocycloalkyl group fused with at least one substituted or unsubstituted aromatic ring, a (C3-C30)cycloalkyl group fused with at least one substituted or unsubstituted aromatic ring, -NR14R15, -SiR16R17R18, -SR19, -OR20, a (C2-C30)alkenyl group, a (C2-C30)alkynyl group, a cyano group, or a nitro group;
R14 to R20 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C5-C30)alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
a, d and e each independently represent an integer of 1 to 4; where a, d or e is an integer of 2 or more, each of R1, each of R4 and each of R5 is the same or different;
b and f each independently represent an integer of 1 to 3; where b or f is an integer of 2 or more, each of R2 and each of R6 is the same or different;
c represents an integer of 1 to 5; where c is an integer of 2 or more, each of R3 is the same or different;
m represents 1, 2 or 3; and
the heterocycloalkyl group and the heteroaryl(ene) group contain at least one hetero atom selected from B, N, O, S, P(=O), Si and P.
Since the organic electroluminescent compounds according to the present invention have high efficiency in transporting electrons, crystallization could be prevented when manufacturing a device. Further, the compounds have good layer formability and improve the current characteristic of the device. Therefore, they can produce an organic electroluminescent device having lowered driving voltages and enhanced power 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 electroluminescent device comprising the material.
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, fluorenyl, phenanthrenyl, 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 2 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 including 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 including 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, a (C1-C30)alkyl group is preferably a (C1-C20)alkyl group, more preferably a (C1-C6)alkyl group; a (C6-C30)aryl group is preferably a (C6-C21)aryl group; a 3- to 30-membered heteroaryl group is preferably a 3- to 21-membered heteroaryl group; a (C3-C30)cycloalkyl group is preferably a (C3-C20)cycloalkyl group, more preferably a (C3-C7)cycloalkyl group
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.
Substituents of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, the substituted aryl(ene) group, the substituted heteroaryl(ene) group, the substituted cycloalkyl(ene) group, the substituted heterocycloalkyl group and the substituted aralkyl group in L1, R1 to R6 and R11 to R20 groups of formula 1, each independently are at least one selected from the group consisting of deuterium; a halogen; a (C1-C30)alkyl group substituted or unsubstituted with a halogen; a (C6-C30)aryl group; a 3- to 30-membered heteroaryl group substituted or unsubstituted with a (C6-C30)aryl; a 5- to 7-membered heterocycloalkyl group; a (C3-C30)cycloalkyl group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyldi(C6-C30)arylsilyl group; a (C2-C30)alkenyl group; a (C2-C30)alkynyl group; a cyano group; a carbazolyl group; a benzocarbazolyl group; a dibenzocarbazolyl group; a di(C1-C30)alkylamino group; a di(C6-C30)arylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a di(C6-C30)arylboronyl group; a di(C1-C30)alkylboronyl group; a (C1-C30)alkyl(C6-C30)arylboronyl group; a (C6-C30)aryl(C1-C30)alkyl group; a (C1-C30)alkyl(C6-C30)aryl group; a carboxyl group; a nitro group; and a hydroxyl group, preferably are at least one selected from the group consisting of deuterium, a halogen, a substituted or unsubstituted (C1-C6)alkyl group, a substituted or unsubstituted (C6-C21)aryl group and a substituted or unsubstituted 3- to 21-membered heteroaryl group, a tri(C6-C12)arylsilyl group, more preferably are at least one selected from the group consisting of deuterium, a halogen, an unsubstituted (C1-C6)alkyl group, an unsubstituted (C6-C21)aryl group, an unsubstituted 3- to 21-membered heteroaryl group and a tri(C6-C12)arylsilyl group.
According to one embodiment of the present invention, in the above formula 1, L1 represents a single bond, a 3- to 30-membered heteroarylene group or a (C6-C30)arylene group; X represents -O-, -S-, -CR11R12- or -NR13-; R11 to R13 each independently represent a (C1-C30)alkyl group, a (C6-C30)aryl group, or a 3- to 30-membered heteroaryl group; R1 to R6 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group, a (C6-C30)aryl group, a 3- to 30-membered heteroaryl group, or a carbazolyl group; m represents 1 or 2; and the heteroarylene and arylene groups in L1, the alkyl, aryl, heteroaryl and carbazolyl groups in R1 to R6 and R11 to R13 can be substituted with at least one selected from the group consisting of deuterium; a halogen; a (C1-C30)alkyl group substituted or unsubstituted with a halogen; a (C6-C30)aryl group; a 3- to 30-membered heteroaryl group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyldi(C6-C30)arylsilyl group; a carbazolyl group; a benzocarbazolyl group; and a dibenzocarbazolyl group.
Preferably, L1 represents a single bond, a phenylene, a naphthylene, a biphenylene, a terphenylene, an anthrylene, an indenylene, a fluorenylene, a phenanthrylene, a triphenylenylene, a pyrenylene, a perylenylene, a crysenylene, a naphthacenylene, a fluoranthenylene, a phenylene-naphthylene, a furylene, a thiophenylene, a pyrrolylene, an imidazolylene, a pyrazolylene, a thiazolylene, a thiadiazolylene, an isothiazolylene, an isoxazolylene, an oxazolylene, an oxadiazolylene, a triazinylene, a tetrazinylene, a triazolylene, a furazanylene, a pyridylene, a pyrazinylene, a pyrimidinylene, a pyridazinylene, a benzofuranylene, a benzothiophenylene, an isobenzofuranylene, a benzoimidazolylene, a benzothiazolylene, a benzoisothiazolylene, a benzoisoxazolylene, a benzoxazolylene, an isoindolylene, an indolylene, an indazolylene, a benzothiadiazolylene, a quinolylene, an isoquinolylene, a cinnolinylene, a quinazolinylene, a quinoxalinylene, a carbazolylene, a phenanthridinylene, a benzodioxolylene, a dibenzofuranylene or a dibenzothiophenylene.
In the above formula 1, L1 is preferably a single bond, or a substituted or unsubstituted (C6-C21)arylene group, more preferably a single bond, or a (C6-C21)arylene group unsubstituted or substituted with a (C1-C6)alkyl group.
R1 to R6 each independently are preferably hydrogen; a halogen; a substituted or unsubstituted (C6-C21)aryl group; a substituted or unsubstituted 3- to 21-membered heteroaryl group, more preferably hydrogen; a halogen; a (C6-C21)aryl group unsubstituted or substituted with a halogen, deuterium, a (C1-C6)alkyl group, a (C6-C21)aryl group, a 3- to 21-membered heteroaryl group or a tri(C6-C12)arylsilyl group; or an unsubstituted 3- to 21-membered heteroaryl group.
R11 to R13 each independently are preferably a substituted or unsubstituted (C1-C6)alkyl group; a substituted or unsubstituted (C6-C21)aryl group; or a substituted or unsubstituted 3- to 21-membered heteroaryl group, more preferably an unsubstituted (C1-C6)alkyl group; a (C6-C21)aryl group unsubstituted or substituted with a halogen, deuterium or a (C1-C6)alkyl group; or a 3- to 21-membered heteroaryl group substituted with a (C6-C21)aryl group.
The representative compounds of the present invention include the following compounds:
Figure PCTKR2012007001-appb-I000003
Figure PCTKR2012007001-appb-I000004
Figure PCTKR2012007001-appb-I000005
Figure PCTKR2012007001-appb-I000006
Figure PCTKR2012007001-appb-I000007
Figure PCTKR2012007001-appb-I000008
Figure PCTKR2012007001-appb-I000009
Figure PCTKR2012007001-appb-I000010
Figure PCTKR2012007001-appb-I000011
Figure PCTKR2012007001-appb-I000012
Figure PCTKR2012007001-appb-I000013
Figure PCTKR2012007001-appb-I000014
Figure PCTKR2012007001-appb-I000015
Figure PCTKR2012007001-appb-I000016
Figure PCTKR2012007001-appb-I000017
Figure PCTKR2012007001-appb-I000018
Figure PCTKR2012007001-appb-I000019
Figure PCTKR2012007001-appb-I000020
Figure PCTKR2012007001-appb-I000021
Figure PCTKR2012007001-appb-I000022
Figure PCTKR2012007001-appb-I000023
The organic electroluminescent compounds according to the present invention can be prepared according to the following reaction scheme.
[Reaction Scheme 1]
Figure PCTKR2012007001-appb-I000024
wherein L1, Z, R1 to R4, m, a, b, c and d 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. The above material can be comprised of the organic electroluminescent compound according to the present invention alone, or can further include conventional materials generally used 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 comprises at least one compound of formula 1 according to the present invention. Further, said organic layer comprises a light-emitting layer in which the organic electroluminescent compound of formula 1 is comprised as a host material.
When the organic electroluminescent compound of formula 1 is used as a host material in the light-emitting layer, one or more phosphorescent dopant can be used together. The phosphorescent dopant applied to the electroluminescent device according to the present invention is not limited, but preferably may be selected from compounds represented by the following formula 2:
Figure PCTKR2012007001-appb-I000025
wherein M1 is selected from the group consisting of Ir, Pt, Pd and Os; L101, L102 and L103 are each independently selected from the following structures:
Figure PCTKR2012007001-appb-I000026
Figure PCTKR2012007001-appb-I000027
Figure PCTKR2012007001-appb-I000028
Figure PCTKR2012007001-appb-I000029
R201 to R203 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a (C6-C30)aryl group unsubstituted or substituted with (C1-C30)alkyl group(s), or a halogen;
R204 to R219 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, SF5, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a cyano group or a halogen;
R220 to R223 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), or a (C6-C30)aryl group unsubstituted or substituted with (C1-C30)alkyl group(s);
R224 and R225 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a halogen, or R224 and R225 are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C5-C30)alicyclic or aromatic ring;
R226 represents a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group or a halogen;
R227 to R229 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group or a halogen;
Q represents
Figure PCTKR2012007001-appb-I000030
,
Figure PCTKR2012007001-appb-I000031
or
Figure PCTKR2012007001-appb-I000032
; R231 to R242 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a (C1-C30)alkoxy group, a halogen, a substituted or unsubstituted (C6-C30)aryl group, a cyano group, or a substituted or unsubstituted (C5-C30)cycloalkyl group, or each of R231 to R242 may be linked to an adjacent substituent via alkylene group or alkenylene group to form a spiro ring or a fused ring or may be linked to R207 or R208 via alkylene group or alkenylene group to form a saturated or unsaturated fused ring.
The dopants of formula 2 include the following, but are not limited thereto:
Figure PCTKR2012007001-appb-I000033
Figure PCTKR2012007001-appb-I000034
Figure PCTKR2012007001-appb-I000035
Figure PCTKR2012007001-appb-I000036
Figure PCTKR2012007001-appb-I000037
Figure PCTKR2012007001-appb-I000038
Figure PCTKR2012007001-appb-I000039
The organic electroluminescent device according to the present invention may further comprise, in addition to the organic electroluminescent compounds 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 comprise a light-emitting layer and a charge generating layer.
In addition, the organic electroluminescent device may emit white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound, besides the organic electroluminescent compound according to the present invention.
Preferably, in the organic electroluminescent device according to the present invention, at least one layer (hereinafter, "a surface layer”) selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s). Specifically, it is preferred that a chalcogenide(includes oxides) layer of silicon or aluminum is placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or metal oxide layer is 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.
Preferably, 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 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.
Hereinafter, the organic electroluminescent compound, the preparation method of the compound, and the luminescent properties of the device comprising the compound of the present invention will be explained in detail with reference to the following examples:
Example 1: Preparation of compound C-35
Figure PCTKR2012007001-appb-I000040
Preparation of compound 1-2
After dissolving compound 1-1 (50 g, 247.2 mmol) in MeCN (50mL) and adding N-bromosuccinimide (NBS) (44 g, 247.2 mmol), the reaction mixture was stirred for 1 day at room temperature. After terminating the reaction, the reaction mixture was extracted with ethyl acetate (EA), and the organic layer was concentrated and purified through silica column to obtain compound 1-2 (55.6 g, 80 %).
Preparation of compound 1-3
After dissolving compound 1-2 (7.7 g, 27.5 mmol) in tetrahydrofuran (THF) (250 mL), the reaction mixture was cooled to -78°C. 2.5 M n-BuLi in hexane (17.6 mL, 44 mmol) was added to the reaction mixture, and the reaction mixture was stirred for 1 hour. B(Oi-Pr)3 (12.6 mL, 55 mmol) was added slowly at the same temperature, and the reaction mixture was stirred for 2 hours. After stirring, the reaction mixture was quenched with adding 2M HCl, was extracted with distilled water and EA, and the organic layer was concentrated. The organic layer was recrystallized with methylene chloride(MC) and hexane to obtain compound 1-3 (4.0 g, 60 %).
Preparation of compound 1-4
After putting compound 1-3 (4.5 g, 18.3 mol), 4-bromoiodobenzene (6.73 g, 23.8 mol), Pd(PPh3)4 (634 mg, 0.55 mmol) and Na2CO3 (5.8 g, 54.9 mol) into toluene (110 mL) and purified water (27 mL), the reaction mixture was stirred for 3 hours at 75°C. After terminating the reaction, the aqueous layer was removed, and the organic layer was concentrated and purified through silica column to obtain compound 1-4 (3.9 g, 60 %).
Preparation of compound 1-7
After putting compound 1-5 (14 g, 48.76 mmol), compound 1-6 (10 g, 40.63 mmol), K2CO3 (13.5 g, 97.52 mmol) and Pd(PPh3)4 (2.35 g, 2.03 mmol) into toluene (200 mL), ethanol (50mL) and purified water (50 mL), the reaction mixture was stirred for 3 hours at 95°C. After terminating the reaction, the reaction mixture was cooled to room temperature. The aqueous layer was removed, and the organic layer was concentrated, was triturated with MC, and was filtered to obtain compound 1-7 (12 g, 72 %).
Preparation of compound C-35
After putting compound 1-4 (3.3 g, 9.2 mmol), compound 1-7 (3.4 g, 8.4 mmol), Cs2CO3 (8.2 g, 25.2 mmol), CuI (880 mg, 4.62 mmol) and ethylenediamine (EDA) (0.6 mL, 8.4 mmol) into toluene (50 mL), the reaction mixture was stirred for 1 day under reflux. The reaction mixture was extracted with EA, was distillated under reduced pressure, and was filtered through column (MC and hexane) to obtain compound C-35 (1.7 g, 29.8 %).
MS/FAB found 684.82; calculated 684.26
Example 2: Preparation of compound C-56
Figure PCTKR2012007001-appb-I000041
Preparation of compound 2-1
After putting compound 1-3 (10 g, 40.6 mol), 4,4'-dibromobiphenyl (38 g, 121.9 mol), Pd(PPh3)4 (2.3 g, 2.03 mmol) and Na2CO3 (12.9 g, 121.9 mol) into toluene (244 mL) and purified water (60 mL), the reaction mixture was stirred for 3 hours at 75°C. After terminating the reaction, the aqueous layer was removed, and the organic layer was concentrated and purified through silica column to obtain compound 2-1 (9.5 g, 54 %).
Preparation of compound C-42
After putting compound 2-1 (5.0 g, 11.5 mmol), compound 1-7 (4.7 g, 11.5 mmol), Pd(OAc)2 (129 mg, 0.575 mmol), 50% P(t-Bu)3 (0.54 mL, 2.3 mmol) and Cs2CO3 (11.2 g, 34.5 mmol) into toluene (50 mL), the reaction mixture was stirred for 1 day under reflux. The reaction mixture was extracted with EA, was distillated under reduced pressure, and was filtered through column (MC and hexane) to obtain compound C-42 (3.5 g, 40 %).
MS/FAB found 760.92; calculated 760.29
Device Example 1: Production of an OLED device using the compound according to the present invention
An OLED device was produced using the compound 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. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus. N1,N1’-([1,1’-biphenyl]-4,4’-diyl)bis(N1-(naphthalen-1-yl)-N4,N4-diphenylbenzene-1,4-diamine) 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’-di(4-biphenyl)-N,N’-di(4-biphenyl)-4,4’-diaminobiphenyl was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, compound C-42 was introduced into one cell of the vacuum vapor depositing apparatus, as a host material, and compound D-7 was introduced into another cell as a dopant. The two materials were evaporated at different rates and were deposited in a doping amount of 4 wt% of the dopant 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. Then, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole was introduced into one cell and lithium quinolate was introduced into another cell. The two materials were evaporated at the same rate and were deposited in a doping amount of 50 wt%, respectively to form an electron transport layer having a thickness of 30nm on the light-emitting layer. Then, 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 red emission having a luminance of 1,060 cd/m2 and a current density of 7.7 mA/cm2 at a driving voltage of 3.9 V. Further, the time taken to be reduced to 90 % of the luminance at a luminance of 5,000 nit was at least 130 hours.
Device Example 2: Production of an OLED device using the compound according to the present invention
An OLED device was produced in the same manner as in Device Example 1, except for using compound C-35 as a host material, and compound D-7 as a dopant.
The produced OLED device showed red emission having a luminance of 1,020 cd/m2 and a current density of 7.5 mA/cm2 at a driving voltage of 3.8 V. Further, the time taken to be reduced to 90 % of the luminance at a luminance of 5,000 nit was at least 130 hours.
Comparative Example 1: Production of an OLED device using conventional electroluminescent compounds
An OLED device was produced in the same manner as in Device Example 1, except that 4,4'-N,N'-dicarbazole-biphenyl was used as a host material and compound D-11 was used as a dopant to deposit a light-emitting layer, and that a hole blocking layer having a thickness of 10 nm was deposited between the light-emitting layer and the electron transport layer by using aluminum(III)bis(2-methyl-8-quinolinato)4- phenylphenolate.
The produced OLED device showed red emission having a luminance of 1,000 cd/m2 and a current density of 20.4 mA/cm2 at a driving voltage of 8.2 V. Further, the time taken to be reduced to 90 % of the luminance at a luminance of 5,000 nit was at least 10 hours.
The organic electroluminescent compounds of the present invention have superior luminous characteristics than the conventional materials. In addition, a device using the compounds according to the present invention as a light-emitting host material increases power efficiency by reducing the driving voltage, and has excellent light emitting efficiency and lifetime characteristic.

Claims (6)

  1. An organic electroluminescent compound represented by the following formula 1:
    Figure PCTKR2012007001-appb-I000042
    wherein
    Z represents
    Figure PCTKR2012007001-appb-I000043
    or
    Figure PCTKR2012007001-appb-I000044
    ;
    L1 represents a single bond, a substituted or unsubstituted 3- to 30-membered heteroarylene group, or a substituted or unsubstituted (C6-C30)arylene group;
    X represents -O-, -S-, -CR11R12- or -NR13-;
    R11 to R13 each independently represent a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group;
    R1 to R6 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group fused with at least one (C3-C30)cycloalkyl, a 5- to 7-membered heterocycloalkyl group fused with at least one substituted or unsubstituted aromatic ring, a (C3-C30)cycloalkyl group fused with at least one substituted or unsubstituted aromatic ring, -NR14R15, -SiR16R17R18, -SR19, -OR20, a (C2-C30)alkenyl group, a (C2-C30)alkynyl group, a cyano group, or a nitro group;
    R14 to R20 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C5-C30)alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
    a, d and e each independently represent an integer of 1 to 4; where a, d or e is an integer of 2 or more, each of R1, each of R4 and each of R5 is the same or different;
    b and f each independently represent an integer of 1 to 3; where b or f is an integer of 2 or more, each of R2 and each of R6 is the same or different;
    c represents an integer of 1 to 5; where c is an integer of 2 or more, each of R3 is the same or different;
    m represents 1, 2 or 3; and
    the heterocycloalkyl group and the heteroaryl(ene) group contain at least one hetero atom selected from B, N, O, S, P(=O), Si and P.
  2. The compound according to claim 1, wherein the substituents of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, the substituted aryl(ene) group, the substituted heteroaryl(ene) group, the substituted cycloalkyl(ene) group, the substituted heterocycloalkyl group and the substituted aralkyl group in L1, R1 to R6 and R11 to R20 groups each independently are at least one selected from the group consisting of deuterium; a halogen; a (C1-C30)alkyl group substituted or unsubstituted with a halogen; a (C6-C30)aryl group; a 3- to 30-membered heteroaryl group substituted or unsubstituted with a (C6-C30)aryl; a 5- to 7-membered heterocycloalkyl group; a (C3-C30)cycloalkyl group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyldi(C6-C30)arylsilyl group; a (C2-C30)alkenyl group; a (C2-C30)alkynyl group; a cyano group; a carbazolyl group; a benzocarbazolyl group; a dibenzocarbazolyl group; a di(C1-C30)alkylamino group; a di(C6-C30)arylamino group; a (C1-C30)alkyl(C6-C30)arylamino group; a di(C6-C30)arylboronyl group; a di(C1-C30)alkylboronyl group; a (C1-C30)alkyl(C6-C30)arylboronyl group; a (C6-C30)aryl(C1-C30)alkyl group; a (C1-C30)alkyl(C6-C30)aryl group; a carboxyl group; a nitro group; and a hydroxyl group.
  3. The compound according to claim 1, wherein
    L1 represents a single bond, a 3- to 30-membered heteroarylene group or a (C6-C30)arylene group;
    X represents -O-, -S-, -CR11R12- or -NR13-;
    R11 to R13 each independently represent a (C1-C30)alkyl group, a (C6-C30)aryl group, or a 3- to 30-membered heteroaryl group;
    R1 to R6 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group, a (C6-C30)aryl group, a 3- to 30-membered heteroaryl group, or a carbazolyl group;
    m represents 1 or 2; and
    the heteroarylene and arylene groups in L1, the alkyl, aryl, heteroaryl and carbazolyl groups in R1 to R6 and R11 to R13 can be substituted with at least one selected from the group consisting of deuterium; a halogen; a (C1-C30)alkyl group substituted or unsubstituted with a halogen; a (C6-C30)aryl group; a 3- to 30-membered heteroaryl group; a tri(C1-C30)alkylsilyl group; a tri(C6-C30)arylsilyl group; a di(C1-C30)alkyl(C6-C30)arylsilyl group; a (C1-C30)alkyldi(C6-C30)arylsilyl group; a carbazolyl group; a benzocarbazolyl group; and a dibenzocarbazolyl group.
  4. The compound according to claim 3, wherein
    L1 represents a single bond, a phenylene, a naphthylene, a biphenylene, a terphenylene, an anthrylene, an indenylene, a fluorenylene, a phenanthrylene, a triphenylenylene, a pyrenylene, a perylenylene, a crysenylene, a naphthacenylene, a fluoranthenylene, a phenylene-naphthylene, a furylene, a thiophenylene, a pyrrolylene, an imidazolylene, a pyrazolylene, a thiazolylene, a thiadiazolylene, an isothiazolylene, an isoxazolylene, an oxazolylene, an oxadiazolylene, a triazinylene, a tetrazinylene, a triazolylene, a furazanylene, a pyridylene, a pyrazinylene, a pyrimidinylene, a pyridazinylene, a benzofuranylene, a benzothiophenylene, an isobenzofuranylene, a benzoimidazolylene, a benzothiazolylene, a benzoisothiazolylene, a benzoisoxazolylene, a benzoxazolylene, an isoindolylene, an indolylene, an indazolylene, a benzothiadiazolylene, a quinolylene, an isoquinolylene, a cinnolinylene, a quinazolinylene, a quinoxalinylene, a carbazolylene, a phenanthridinylene, a benzodioxolylene, a dibenzofuranylene or a dibenzothiophenylene.
  5. The compound according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
    Figure PCTKR2012007001-appb-I000045
    Figure PCTKR2012007001-appb-I000046
    Figure PCTKR2012007001-appb-I000047
    Figure PCTKR2012007001-appb-I000048
    Figure PCTKR2012007001-appb-I000049
    Figure PCTKR2012007001-appb-I000050
    Figure PCTKR2012007001-appb-I000051
    Figure PCTKR2012007001-appb-I000052
    Figure PCTKR2012007001-appb-I000053
    Figure PCTKR2012007001-appb-I000054
    Figure PCTKR2012007001-appb-I000055
    Figure PCTKR2012007001-appb-I000056
    Figure PCTKR2012007001-appb-I000057
    Figure PCTKR2012007001-appb-I000058
    Figure PCTKR2012007001-appb-I000059
    Figure PCTKR2012007001-appb-I000060
    Figure PCTKR2012007001-appb-I000061
    Figure PCTKR2012007001-appb-I000062
    Figure PCTKR2012007001-appb-I000063
    Figure PCTKR2012007001-appb-I000064
    Figure PCTKR2012007001-appb-I000065
  6. An organic electroluminescent device comprising the compound according to claim 1.
PCT/KR2012/007001 2011-09-01 2012-08-31 Novel organic electroluminescent compounds and organic electroluminescent device using the same WO2013032278A1 (en)

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WO2015050173A1 (en) * 2013-10-03 2015-04-09 出光興産株式会社 Compound, organic electroluminescent element, and electronic device
CN104650118A (en) * 2014-07-01 2015-05-27 吉林奥来德光电材料股份有限公司 Preparation method and application of derivative by taking dibenzofuran as skeleton core
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CN106715394A (en) * 2015-06-16 2017-05-24 出光兴产株式会社 Compound, material for organic electroluminescent element, and electronic device
US10790449B2 (en) * 2015-06-16 2020-09-29 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic device
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