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WO2013012298A1 - 9h-carbazole compounds and electroluminescent devices involving them - Google Patents

9h-carbazole compounds and electroluminescent devices involving them Download PDF

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Publication number
WO2013012298A1
WO2013012298A1 PCT/KR2012/005841 KR2012005841W WO2013012298A1 WO 2013012298 A1 WO2013012298 A1 WO 2013012298A1 KR 2012005841 W KR2012005841 W KR 2012005841W WO 2013012298 A1 WO2013012298 A1 WO 2013012298A1
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unsubstituted
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PCT/KR2012/005841
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French (fr)
Inventor
Chi-Sik Kim
Hee-Sook Kim
Hyo-Jung Lee
Hye-Mi Kim
Doo-Hyeon Moon
Soo-Jin Hwang
Seon-Woo Lee
Soo-Jin Yang
Su-Hyun Lee
Kyung-Joo Lee
Hyo-Nim Shin
Kyoung-Jin Park
Young-Jun Cho
Hyuck-jun KWON
Bong-Ok Kim
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DuPont Specialty Materials Korea Ltd
DuPont Electronic Materials International LLC
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Rohm and Haas Electronic Materials Korea Ltd
Rohm and Haas Electronic Materials LLC
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Priority claimed from KR1020120078704A external-priority patent/KR20130011955A/en
Application filed by Rohm and Haas Electronic Materials Korea Ltd, Rohm and Haas Electronic Materials LLC filed Critical Rohm and Haas Electronic Materials Korea Ltd
Priority to CN201280045815.0A priority Critical patent/CN104039778A/en
Priority to JP2014521569A priority patent/JP2014521604A/en
Publication of WO2013012298A1 publication Critical patent/WO2013012298A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/002—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—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
    • 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
    • C07D491/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • 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

Definitions

  • the present invention relates to novel organic electroluminescence compounds and organic electroluminescence device using the same.
  • An electroluminescence (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.
  • Korean Patent No. KR 0948700 discloses as compounds for an organic EL device an arylcarbazole compound substituted with a heteroaryl group comprising a nitrogen atom. However, it does not disclose a carbazole compound which is substituted with a heterocycloalkyl group or a cycloalkyl group fused with an aromatic ring at the 3 position of the carbazole, and which is directly or indirectly linked to a substituted or unsubstituted heteroaryl.
  • the objective of the present invention is to provide an organic electroluminescence compound imparting high luminous efficiency and a long operation lifetime to a device, and having proper color coordination; and an organic electroluminescence device having high efficiency and a long lifetime, using said compound as a light-emitting material.
  • L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted 3- to 30-membered heteroarylene group, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (C6-C30)cycloalkylene group;
  • X 1 and X 2 each independently represent CR’ or N;
  • Y represents -O-, -S-, -CR 5 R 6 - or -NR 7 -;
  • Ar 1 , Ar 2 and R’ 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 3- to 30-membered heteroaryl group;
  • R 1 to R 4 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, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , a cyano group, a nitro group, or a hydroxyl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C5-C30)alicycl
  • R 5 to R 7 and R 11 to R 17 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 5- to 7-membered heterocycloalkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl 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 and c each independently represent an integer of 1 to 4; where a or c is an integer of 2 or more, each of R 1 or each of R 3 is the same or different;
  • the organic electroluminescence compounds according to the present invention can manufacture an organic electroluminescence device which has high luminous efficiency and a long operation lifetime.
  • the 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 electroluminescence device having lowered driving voltages and enhanced power efficiency.
  • the present invention relates to an organic electroluminescence compound represented by the above formula 1 and an organic electroluminescence device comprising the compound.
  • (C1-C30)alkyl(ene) is meant to be a linear or branched alkyl(ene) having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.;
  • (C2-C30) alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • “(C2-C30)alkynyl” is a linear or branched alkynyl having 2 to 30 carbon atoms, in which
  • 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 and L 2 each independently represent a single bond, a 3- to 30-membered heteroarylene group, or a (C6-C30)arylene group
  • X 1 and X 2 each independently represent CR’ or N
  • Y represents -O-, -S-, -CR 5 R 6 - or -NR 7 -
  • Ar 1 , Ar 2 and R’ each independently represent hydrogen, a (C1-C30)alkyl group, a (C6-C30)aryl group, or a 3- to 30-membered heteroaryl group
  • R 1 to R 4 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group, a (C6-C30)aryl group, a 3- to 30-membered heteroaryl group, -NR 11 R 12 , or -SiR 13 R 14 R 15 ; or R 3 is linked to an adjacent substituent(s) to form a mono- or polycyclic, (C5-C
  • L 1 and L 2 each independently represent a single bond, phenylene, biphenylene, terphenylene, indenylene, fluorenylene, triphenylenylene, pyrenylene, perylenylene, crycenylene, naphthacenylene, fluorantenylene, thiophenylene, pyrrolylene, pyrazolylene, thiazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, furazanylene, pyridylene, benzofuranylene, benzothiophenylene, indolylene, benzoimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzoxazolylene, benzothiadiazolylene, dibenzofuranylene, or dibenzothiophenylene; Ar 1 , Ar 2 and R’ each independently represent hydrogen,
  • organic electroluminescence compounds according to the present invention include the following compounds:
  • organic electroluminescence compounds according to the present invention can be prepared according to the following reaction scheme.
  • Ar 1 , Ar 2 , L 1 , L 2 , Y, X 1 , X 2 , R 1 to R 4 , a, b, c and d are as defined in formua 1 above, and Hal represents a halogen.
  • the present invention provides an organic electroluminescence device comprising the compound of formula 1.
  • the organic electroluminescence device according to the present invention 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 at least one compound of formula 1 according to the present invention.
  • One of the first electrode and the second electrode can be an anode, and the other can be a cathode.
  • Said organic layer comprises a light-emitting layer, and can further comprise at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer and a hole blocking layer.
  • the compound of formula 1 can be comprised in at least one of the light-emitting layer and the hole transport layer.
  • the compound of formula 1 can be comprised as a hole transport material.
  • the compound of formula 1 can be comprised as a host material.
  • the light-emitting layer can further comprise at least one dopant; if necessary, the light-emitting layer can further comprise a second host material in addition to the compound of formula 1.
  • a phosphorescence dopant which can be included in the organic electroluminescence device of the present invention is not limited to, but is preferably a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably, an ortho metalated complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), even more preferably, an ortho metalated iridium complex compound.
  • the phosphorescence dopant is preferably selected from compounds represented by the following formulae 2 to 4.
  • L is selected from the following structures:
  • R 100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group
  • R 101 to R 109 and R 111 to R 127 each independently hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl group, cyano or a substituted or unsubstituted (C1-C30)alkoxy group
  • R 201 to R 211 each independently hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with a halogen, or a substituted or unsubstituted (C3-C30)cycloalkyl group
  • f and g each independently an integer of 1 to
  • the phosphorescence dopant material includes the following:
  • the organic electroluminescence device comprises a first electrode, a second electrode, and at least one organic layer between the first and second electrodes.
  • the organic layer comprises a light-emitting layer which comprises a composition for an organic electroluminescence device according to the present invention and a phosphorescence dopant material.
  • the composition for an organic electroluminescence device is used as a host material.
  • the organic electroluminescence device may further comprise, in addition to the 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 electroluminescence 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 compound according to the present invention. Further, as occasion demands, the organic electroluminescence device can comprise a yellow or orange light-emitting layer.
  • 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
  • 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 electroluminescence 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 electroluminescence 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-48 was introduced into another cell as a dopant.
  • the two materials were evaporated at different rates and were deposited in a doping amount of 15 wt% 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 same rates and were deposited in a doping amount of 50 wt% 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 green emission having a luminance of 1000 cd/m 2 and a current density of 2.17 mA/cm 2 at a driving voltage of 4.4 V.
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-44 as a host material, and compound D-1 as a dopant.
  • the produced OLED device showed green emission having a luminance of 2030 cd/m 2 and a current density of 4.39 mA/cm 2 at a driving voltage of 3.1 V.
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-52 as a host material, and compound D-9 as a dopant.
  • the produced OLED device showed green emission having a luminance of 1000 cd/m 2 and a current density of 2.35 mA/cm 2 at a driving voltage of 3.5 V.
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-54 as a host material, and compound D-1 as a dopant.
  • the produced OLED device showed green emission having a luminance of 1050 cd/m 2 and a current density of 2.21 mA/cm 2 at a driving voltage of 3.8 V.
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-56 as a host material, and compound D-1 as a dopant.
  • the produced OLED device showed orange emission having a luminance of 1510 cd/m 2 and a current density of 3.41 mA/cm 2 at a driving voltage of 2.7 V.
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-57 as a host material, and compound D-48 as a dopant.
  • the produced OLED device showed green emission having a luminance of 2160 cd/m 2 and a current density of 5.65 mA/cm 2 at a driving voltage of 4.1 V.
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-59 as a host material, and compound D-48 as a dopant.
  • the produced OLED device showed green emission having a luminance of 1470 cd/m 2 and a current density of 3.56 mA/cm 2 at a driving voltage of 3.8 V.
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-61 as a host material, and compound D-9 as a dopant.
  • the produced OLED device showed green emission having a luminance of 1130 cd/m 2 and a current density of 2.69 mA/cm 2 at a driving voltage of 2.7 V.
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-62 as a host material, and compound D-1 as a dopant.
  • the produced OLED device showed orange emission having a luminance of 890 cd/m 2 and a current density of 2.51 mA/cm 2 at a driving voltage of 2.6 V.
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-68 as a host material, and compound D-48 as a dopant.
  • the produced OLED device showed green emission having a luminance of 1100 cd/m 2 and a current density of 3.98 mA/cm 2 at a driving voltage of 2.6 V
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-81 as a host material, and compound D-1 as a dopant.
  • the produced OLED device showed green emission having a luminance of 1070 cd/m 2 and a current density of 2.60 mA/cm 2 at a driving voltage of 3.0 V.
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-100 as a host material, and compound D-48 as a dopant.
  • the produced OLED device showed green emission having a luminance of 4210 cd/m 2 and a current density of 9.29 mA/cm 2 at a driving voltage of 4.9 V.
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-101 as a host material, and compound D-1 as a dopant.
  • the produced OLED device showed orange emission having a luminance of 3630 cd/m 2 and a current density of 9.75 mA/cm 2 at a driving voltage of 4.0 V.
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-102 as a host material, and compound D-1 as a dopant.
  • the produced OLED device showed green emission having a luminance of 1870 cd/m 2 and a current density of 4.00 mA/cm 2 at a driving voltage of 3.7 V.
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-104 as a host material, and compound D-9 as a dopant.
  • the produced OLED device showed orange emission having a luminance of 1010 cd/m 2 and a current density of 2.42 mA/cm 2 at a driving voltage of 2.6 V.
  • Comparative Example 1 Production of an OLED device using conventional electroluminescent compounds
  • An OLED device was produced in the same manner as that of Example 1, except that a light-emitting layer having a thickness of 30 nm was deposited on the hole transport layer by using 4,4’-N,N’-dicarbazol-biphenyl as a host material and Ir(ppy) 3 as a dopant and that a hole blocking layer having a thickness of 10 nm was deposited by using aluminum(III) bis(2-methyl-8-quinolinato)-4-phenylphenolate.
  • the produced OLED device showed green emission having a luminance of 1000 cd/m 2 and a current density of 2.89 mA/cm 2 at a driving voltage of 4.8 V.
  • the organic electroluminescence 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 green or orange light emitting host material not only has excellent luminous characteristics, but also induces an increase in power efficiency by reducing the driving voltage.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The present invention relates to a novel organic luminescent compound and an organic electroluminescent device containing the same. The compounds according to the present invention have high luminous efficiency and long operation lifetime. Therefore, they can produce an organic electroluminescent device having an improved power consumption.

Description

NOVEL ORGANIC ELECTROLUMINESCENCE COMPOUNDS AND ORGANIC ELECTROLUMINESCENCE DEVICE USING THE SAME
The present invention relates to novel organic electroluminescence compounds and organic electroluminescence device using the same.
An electroluminescence (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.
In order to improve color purity, luminous efficiency and stability, light-emitting materials prepared by mixing a dopant with a host material can be used. In the host material/dopant system, the host material has a great influence on the efficiency and performance of an EL device, and thus the selection is important. 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known host material for phosphorescent substances. Further, Pioneer (Japan) et al. developed a high performance organic EL device employing, as a host material, bathocuproine (BCP) and aluminum(III)bis(2-methyl-8-quinolinate)(4-phenylphenolate) (BAlq) which had been a material used for a hole blocking layer.
Though these phosphorous host materials provide good light-emitting characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, their degradation may occur during a high-temperature deposition process in a vacuum. (2) The power efficiency of an organic EL device is given by [(π/voltage) × current efficiency], and the power efficiency is inversely proportional to the voltage, and thus the power efficiency should be high in order to reduce power consumption. Although an organic EL device comprising phosphorescent materials provides higher current efficiency (cd/A) than one comprising fluorescent materials, the organic EL device has a considerably high driving voltage. Thus, the EL device using the conventional phosphorescent materials has no advantage in terms of power efficiency (lm/W). (3) Further, the operation lifetime of an organic EL device is short and luminous efficiency is still required to be improved.
Korean Patent No. KR 0948700 discloses as compounds for an organic EL device an arylcarbazole compound substituted with a heteroaryl group comprising a nitrogen atom. However, it does not disclose a carbazole compound which is substituted with a heterocycloalkyl group or a cycloalkyl group fused with an aromatic ring at the 3 position of the carbazole, and which is directly or indirectly linked to a substituted or unsubstituted heteroaryl.
The objective of the present invention is to provide an organic electroluminescence compound imparting high luminous efficiency and a long operation lifetime to a device, and having proper color coordination; and an organic electroluminescence 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 a compound represented by the following formula 1:
Figure PCTKR2012005841-appb-I000001
wherein
L1 and L2 each independently represent a single bond, a substituted or unsubstituted 3- to 30-membered heteroarylene group, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (C6-C30)cycloalkylene group;
X1 and X2 each independently represent CR’ or N;
Y represents -O-, -S-, -CR5R6- or -NR7-;
Ar1, Ar2 and R’ 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 3- to 30-membered heteroaryl group;
R1 to R4 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, -NR11R12, -SiR13R14R15, -SR16, -OR17, a cyano group, a nitro group, or a hydroxyl 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;
R5 to R7 and R11 to R17 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 5- to 7-membered heterocycloalkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl 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 and c each independently represent an integer of 1 to 4; where a or c is an integer of 2 or more, each of R1 or each of R3 is the same or different;
b and d each independently represent an integer of 1 to 3; where b or d is an integer of 2 or more, each of R2 or each of R4 is the same or different; and the heteroarylene group, the heterocycloalkyl group and the heteroaryl group contain at least one hetero atom selected from B, N, O, S, P(=O), Si and P.
The organic electroluminescence compounds according to the present invention can manufacture an organic electroluminescence device which has high luminous efficiency and a long operation lifetime.
In addition, since the 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 electroluminescence 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 electroluminescence compound represented by the above formula 1 and an organic electroluminescence device comprising the compound.
Herein, “(C1-C30)alkyl(ene)” is meant to be a linear or branched alkyl(ene) having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.; “(C2-C30) alkenyl” is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.; “(C2-C30)alkynyl” is a linear or branched alkynyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.; “(C3-C30)cycloalkyl” is a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.; “(C6-C30)cycloalkylene” is one formed by removing a hydrogen from cycloalkyl having 6 to 30, preferably 6 to 20, more preferably 6 to 12 carbon atoms; “3- 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 3 to 7 ring backbone atoms, and includes tetrahydrofurane, pyrrolidine, thiolan, tetrahydropyran, etc.; “(C6-C30)aryl(ene)” is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 20, more preferably 6 to 15, 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 3 to 30 ring backbone atoms; is a monocyclic ring, or a fused ring condensed with at least one benzene ring; has preferably 5 to 20, more preferably 5 to 15 ring backbone atoms; 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, “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 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, L2, R’, Ar1, Ar2, R1 to R4, R5 to R7 and R11 to R17 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 (C3-C30)cycloalkyl group; a 5- to 7-membered heterocycloalkyl 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; an N-carbazolyl 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.
In the above formula 1, L1 and L2 each independently represent a single bond, a 3- to 30-membered heteroarylene group, or a (C6-C30)arylene group; X1 and X2 each independently represent CR’ or N; Y represents -O-, -S-, -CR5R6- or -NR7-; Ar1, Ar2 and R’ each independently represent hydrogen, a (C1-C30)alkyl group, a (C6-C30)aryl group, or a 3- to 30-membered heteroaryl group; R1 to R4 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group, a (C6-C30)aryl group, a 3- to 30-membered heteroaryl group, -NR11R12, or -SiR13R14R15; or R3 is 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; R5 to R7 and R11 to R17 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group, a (C6-C30)aryl group, or a 3- to 30-membered heteroaryl group; and the arylene group and the heteroarylene group in L1 and L2, and the alkyl group, the aryl group, and the heteroaryl group in Ar1, Ar2, R’, R1 to R4, R5 to R7 and R11 to R17 each independently 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 substituted or unsubstituted with a (C6-C30)aryl; 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; an N-carbazolyl group; a di(C1-C30)alkylamino group; a di(C6-C30)arylamino group; a (C1-C30)alkyl(C6-C30)aryl amino group; and a (C1-C30)alkyl(C6-C30)aryl group.
More specifically, L1 and L2 each independently represent a single bond, phenylene, biphenylene, terphenylene, indenylene, fluorenylene, triphenylenylene, pyrenylene, perylenylene, crycenylene, naphthacenylene, fluorantenylene, thiophenylene, pyrrolylene, pyrazolylene, thiazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, furazanylene, pyridylene, benzofuranylene, benzothiophenylene, indolylene, benzoimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzoxazolylene, benzothiadiazolylene, dibenzofuranylene, or dibenzothiophenylene; Ar1, Ar2 and R’ each independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifuloroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, fluorenyl, fluorantenyl, terphenyl, pyrenyl, crycenyl, naphthacenyl, perylenyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, quinolyl, triazinyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, quinoxalinyl, or N-carbazolyl; R1 to R4 each independently represent hydrogen, deuterium, chloro, fluoro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifuloroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, anthryl, biphenyl, fluorenyl, fluorantenyl, triphenylenyl, pyrenyl, crycenyl, naphthacenyl, perylenyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, indenyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, N-carbazolyl, dimethylamino, diethylamino, methylphenylamino, diphenylamino, trimethylsilyl, triethylsilyl, tripropylsilyl, tri(t-butyl)silyl, t-butyldimethylsilyl, dimethylphenylsilyl, or triphenylsilyl; a to d each independently represent 1 or 2, more preferably 1; the substituents in Ar1, Ar2, R’, and R1 to R4 each independently can be substituted with at least one selected from the group consisting of deuterium, chloro, fluoro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifuloroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, fluorantenyl, triphenylenyl, pyrenyl, crycenyl, naphthacenyl, perylenyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, benzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzothiophenyl, pyrazolyl, indolyl, carbazolyl, N-carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, dimethylamino, diethylamino, methylphenylamino, diphenylamino, trimethylsilyl, triethylsilyl, tripropylsilyl, tri(t-butyl)silyl, t-butyldimethylsilyl, dimethylphenylsilyl, methyldiphenylsilyl, triphenylsilyl, and N-phenylcarbazolyl.
The organic electroluminescence compounds according to the present invention include the following compounds:
Figure PCTKR2012005841-appb-I000002
Figure PCTKR2012005841-appb-I000003
Figure PCTKR2012005841-appb-I000004
Figure PCTKR2012005841-appb-I000005
Figure PCTKR2012005841-appb-I000006
Figure PCTKR2012005841-appb-I000007
Figure PCTKR2012005841-appb-I000008
Figure PCTKR2012005841-appb-I000009
Figure PCTKR2012005841-appb-I000010
Figure PCTKR2012005841-appb-I000011
Figure PCTKR2012005841-appb-I000012
Figure PCTKR2012005841-appb-I000013
Figure PCTKR2012005841-appb-I000014
Figure PCTKR2012005841-appb-I000015
Figure PCTKR2012005841-appb-I000016
Figure PCTKR2012005841-appb-I000017
Figure PCTKR2012005841-appb-I000018
Figure PCTKR2012005841-appb-I000019
Figure PCTKR2012005841-appb-I000020
Figure PCTKR2012005841-appb-I000021
Figure PCTKR2012005841-appb-I000022
Figure PCTKR2012005841-appb-I000023
Figure PCTKR2012005841-appb-I000024
The organic electroluminescence compounds according to the present invention can be prepared according to the following reaction scheme.
[Reaction Scheme 1]
Figure PCTKR2012005841-appb-I000025
[Reaction Scheme 2]
Figure PCTKR2012005841-appb-I000026
wherein Ar1, Ar2, L1, L2, Y, X1, X2, R1 to R4, a, b, c and d are as defined in formua 1 above, and Hal represents a halogen.
In addition, the present invention provides an organic electroluminescence device comprising the compound of formula 1. The organic electroluminescence device according to the present invention 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 at least one compound of formula 1 according to the present invention.
One of the first electrode and the second electrode can be an anode, and the other can be a cathode. Said organic layer comprises a light-emitting layer, and can further comprise at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer and a hole blocking layer.
The compound of formula 1 can be comprised in at least one of the light-emitting layer and the hole transport layer. In the hole transport layer, the compound of formula 1 can be comprised as a hole transport material. In the light-emitting layer, the compound of formula 1 can be comprised as a host material. Preferably, the light-emitting layer can further comprise at least one dopant; if necessary, the light-emitting layer can further comprise a second host material in addition to the compound of formula 1.
As a dopant, at least one phosphorescence dopant is preferable. A phosphorescence dopant which can be included in the organic electroluminescence device of the present invention is not limited to, but is preferably a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably, an ortho metalated complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), even more preferably, an ortho metalated iridium complex compound.
The phosphorescence dopant is preferably selected from compounds represented by the following formulae 2 to 4.
Figure PCTKR2012005841-appb-I000027
In the above formulae 2 to 4, L is selected from the following structures:
Figure PCTKR2012005841-appb-I000028
wherein R100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group; R101 to R109 and R111 to R127 each independently hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl group, cyano or a substituted or unsubstituted (C1-C30)alkoxy group; R201 to R211 each independently hydrogen, deuterium, a halogen, a (C1-C30)alkyl group unsubstituted or substituted with a halogen, or a substituted or unsubstituted (C3-C30)cycloalkyl group; f and g each independently an integer of 1 to 3, and h represent an integer of 1 or 2, f to h, where each of f to h is an integer of 2 or more, each R100 is different or the same; and n is an integer of 1 to 3.
The phosphorescence dopant material includes the following:
Figure PCTKR2012005841-appb-I000029
Figure PCTKR2012005841-appb-I000030
Figure PCTKR2012005841-appb-I000031
Figure PCTKR2012005841-appb-I000032
Figure PCTKR2012005841-appb-I000033
Figure PCTKR2012005841-appb-I000034
Figure PCTKR2012005841-appb-I000035
Figure PCTKR2012005841-appb-I000036
Figure PCTKR2012005841-appb-I000037
Figure PCTKR2012005841-appb-I000038
Figure PCTKR2012005841-appb-I000039
Figure PCTKR2012005841-appb-I000040
Further, the organic electroluminescence device comprises a first electrode, a second electrode, and at least one organic layer between the first and second electrodes. The organic layer comprises a light-emitting layer which comprises a composition for an organic electroluminescence device according to the present invention and a phosphorescence dopant material. The composition for an organic electroluminescence device is used as a host material.
The organic electroluminescence device according to the present invention may further comprise, in addition to the 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 electroluminescence 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 electroluminescence 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 compound according to the present invention. Further, as occasion demands, the organic electroluminescence device can comprise a yellow or orange light-emitting layer.
Preferably, in the organic electroluminescence 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 electroluminescence 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 electroluminescence 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 electroluminescence device having two or more electroluminescent layers and emitting white light.
Hereinafter, the organic electroluminescence 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-52
Figure PCTKR2012005841-appb-I000041
Preparation of compound 1-1
After dissolving dibenzo[b,d]thiophen-4yl boronic acid (14 g, 61 mmol), 3-bromo-9H-carbazole (10 g, 41 mmol) and K2CO3 (19.1 g, 138 mmol) in a mixed solvent of toluene (200mL)/ EtOH (100 mL)/ distilled water (100 mL), Pd(PPh3)4 (2.3 g, 2 mmol) was added. The reaction mixture was stirred for 5 hours at 120°C, was cooled to room temperature, and was extracted with EA (800 mL). The obtained organic layer was washed with distilled water (200 mL), and was distilled under reduced pressure to remove the organic solvent. The obtained solid was washed methanol, was filtered, was dried, and was separated with silica gel column chromatography and recrystallization to obtain compound 1-1 (10 g, 71 %).
Preparation of compound 1-2
After dissolving biphenyl-4-yl boronic acid (50 g, 250 mmol), 1,3-dibromobenzene (46 mL, 380 mmol) and Na2CO3 (66 g, 630 mmol) in a mixed solvent of toluene (700mL)/ EtOH (320 mL)/ distilled water (320 mL), Pd(PPh3)2Cl2 (5.6 g, 8 mmol) was added. The reaction mixture was stirred for 5 hours at 120°C, was cooled to room temperature, and was extracted with EA (1.5 L). The obtained organic layer was washed with distilled water (400 mL), and was distilled under reduced pressure to remove the organic solvent. The obtained solid was washed methanol, was filtered, was dried, and was separated with silica gel column chromatography and recrystallization to obtain compound 1-2 (28 g, 56 %).
Preparation of compound 1-3
After dissolving compound 1-2 (20 g, 65 mmol) in THF (350 mL), and adding n-BuLi (2.5 M in hexane, 39 mL, 97 mmol) to the reaction mixture at -78°C, the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 2 hours with adding B(OMe)3 (11 mL, 97 mmol) slowly to the reaction mixture. After terminating the reaction with ammonium chloride aqueous solution (50 mL), the reaction mixture was extracted with EA (1 L). The obtained organic layer was washed with distilled water (200 mL). The obtained organic layer was dried with anhydrous MgSO4 to remove the remaining moisture, was distillated under reduced pressure to remove the solvent. The obtained solid was separated with recrystallization to obtain compound 1-3 (14 g, 79 %).
Preparation of compound 1-4
After dissolving compound 1-3 (14 g, 51 mmol), 2,4-dichloropyrimidine (11 g, 77 mmol) and Na2CO3 (13.5 g, 128 mmol) in a mixed solvent of toluene (130mL)/ EtOH (65 mL)/ distilled water (65 mL), Pd(PPh3)4 (3 g, 2.6 mmol) was added. The reaction mixture was stirred for 5 hours at 120°C, was cooled to room temperature, and was extracted with EA (300 mL). The obtained organic layer was washed with distilled water (100 mL), and was distilled under reduced pressure to remove the organic solvent. The obtained solid was washed methanol, was filtered, was dried, and was separated with silica gel column chromatography and recrystallization to obtain compound 1-4 (8 g, 46 %).
Preparation of compound C-52
After dissolving compound 1-1 (5 g, 14 mmol) in DMF (100 mL), the reaction mixture was stirred with slowly adding NaH (0.9 g, 22 mmol), and was stirred for 30 minutes. After dissolving compound 1-4 (5.4 g, 16 mmol) in DMF (50 mL), it was added the reaction mixture and was stirred for 4 hours. The reaction mixture was added to distilled water (300 mL) with stirring for 30 minutes. The obtained solid was separated with recrystallization to obtain compound C-52 (2.4 g, 26 %).
Example 2: Preparation of compound C-54
Figure PCTKR2012005841-appb-I000042
Preparation of compound 2-1
After dissolving carbazole (25 g, 149.5 mmol), 1,3-dibromobenzene (57 mL, 448.5 mmol), CuI (14.2 g, 74.7 mmol), ethylenediamine (5 mL, 74.7 mmol) and K3PO4 (95 g, 448.5 mmol) in toluene (450 mL), the reaction mixture was stirred for 24 hours at 120°C under reflux. After terminating the reaction, the reaction mixture was extracted with EA. The obtained organic layer was dried with anhydrous MgSO4 to remove the remaining moisture, was distillated under reduced pressure to remove the solvent, and was filtered through column to obtain compound 2-1 (42 g, 85 %).
Preparation of compound 2-2
After dissolving compound 2-1 (42 g, 130.3 mmol) in THF (500 mL), the reaction mixture was cooled to -78°C. After 10 minutes, n-BuLi (67 mL, 169.4 mmol, 2.5 M in hexane) was slowly added, and the reaction mixture was stirred for 1 hour. And then, B(OMe)3 (23 mL, 208.5 mmol) was slowly added, and the reaction mixture was stirred for 24 hours. After terminating the reaction, 1M HCl was added, and the reaction mixture was extracted with EA. The obtained organic layer was dried with anhydrous MgSO4 to remove the remaining moisture, was distillated under reduced pressure to remove the solvent, and was recrystallized with MC/hexane to obtain compound 2-2 (25 g, 67 %).
Preparation of compound 2-3
After dissolving compound 2-2 (8.9 g, 30.9 mmol), 2,4-dichloropyrimidine (6.9 g, 46.6 mmol), Pd(PPh3)4 (1.8 g, 1.5 mmol) and Na2CO3 (8.2 g, 77 mmol) in a mixed solvent of toluene (120mL)/ EtOH (40 mL), the reaction mixture was stirred for 24 hours at 120°C. And then, after terminating the reaction with adding slowly distilled water, the reaction mixture was extracted with EA. The obtained organic layer was dried with anhydrous MgSO4 to remove the remaining moisture, was distillated under reduced pressure to remove the solvent, and was filtered through column to obtain compound 2-3 (7 g, 63.6 %).
Preparation of compound C-54
After dissolving NaH (674 mg, 16.8 mol) in DMF, the solution was stirred. After dissolving compound 1-1 (4.7 g, 13.5 mmol) in DMF, the solution was added to the NaH solution, and was stirred for 1 hour. After dissolving compound 2-3 (4 g, 11.2 mmol) in DMF, the solution was stirred. And then, the mixed solution of compound 1-1 was added to the mixed solution of compound 2-3, and was stirred for 24 hours at room temperature. After terminating the reaction, the obtained solid was filtered, was washed with EA and was filtered through column to obtain compound C-54 (4 g, 44 %).
Example 3: Preparation of compound C-56
Figure PCTKR2012005841-appb-I000043
Preparation of compound 3-1
After mixing 2,4,6-trichloropyrimidine (10 g, 54.51 mmol), phenyl boronic acid (16.6 g, 136.29 mmol), Pd(PPh3)4 (3.15 g, 2.72 mmol), 2 M K2CO3 (50 mL), toluene (100mL) and EtOH (30 mL), the reaction mixture was stirred under reflux. After 4 hours, the reaction mixture was cooled to room temperate, and the distilled water was added. The reaction mixture was extracted with EA. The obtained organic layer was dried with anhydrous MgSO4 to remove the remaining moisture, was distillated under reduced pressure to remove the solvent, and was filtered through column to obtain compound 3-1 (7 g, 48 %).
Preparation of compound C-56
After dissolving NaH (875 mg, 21.8 mmol) in DMF, the solution was stirred. After dissolving compound 1-1 (5.1 g, 14.5 mmol) in DMF, the solution was added to the NaH solution, and was stirred for 1 hour. After dissolving compound 3-1 (4.7 g, 17.5 mmol) in DMF, the solution was stirred. And then, the mixed solution of compound 1-1 was added to the mixed solution of compound 3-1, and was stirred for 24 hours at room temperature. After terminating the reaction, the obtained solid was filtered, was washed with EA and was filtered through column to obtain compound C-56 (4.5 g, 53 %).
Example 4: Preparation of compound C-63
Figure PCTKR2012005841-appb-I000044
Preparation of compound 4-1
After mixing compound 1-1 (20 g, 57 mmol), 1,3-dibromobenzene (54 g, 226 mmol), CuI (5 g, 28 mmol), K3PO4 (36 g, 169 mmol) and toluene (280 mL), the reaction mixture was stirred for 10 minutes at 80°C. After adding ethylenediamine (3.5 mL, 51 mmol), the reaction mixture was stirred for 12 hours at 140°C. After terminating the reaction, the reaction mixture was extracted with EA. The obtained organic layer was dried with anhydrous MgSO4 to remove the remaining moisture, was distillated under reduced pressure to remove the solvent, and was filtered through column to obtain a white solid, compound 4-1 (13 g, 45 %).
Preparation of compound 4-2
After dissolving compound 4-1 (13 g, 25 mmol) in THF (125 mL), n-BuLi (13 mL, 2.25 M solution in hexane) was slowly added with stirring the reaction mixture under nitrogen atmosphere. The reaction mixture was stirred for 1 hours at the same temperature, and then B(OMe)3 (4.8 mL, 42 mmol) was slowly added at the same temperature. The reaction mixture was heated to room temperature, and was stirred for 12 hours. After terminating the reaction, the reaction mixture was extracted with EA. The obtained organic layer was dried with anhydrous MgSO4 to remove the remaining moisture, was distillated under reduced pressure to remove the solvent, and was recrystallized to obtain a white solid, compound 4-2 (9 g, 77 %).
Preparation of compound 4-3
After mixing 2,4,6-trichloro-1,3,5-triazine (10.1 g, 54.51 mmol), phenyl boronic acid (16.6 g, 136.29 mmol), Pd(PPh3)4 (3.15 g, 2.72 mmol), 2 M K2CO3 (50 mL), toluene (100mL) and EtOH (30 mL), the reaction mixture was stirred under reflux. After 4 hours, the reaction mixture was cooled to room temperate, and the distilled water was added. The reaction mixture was extracted with EA. The obtained organic layer was dried with anhydrous MgSO4 to remove the remaining moisture, was distillated under reduced pressure to remove the solvent, and was filtered through column to obtain compound 4-3 (7 g, 48 %).
Preparation of compound C-63
After mixing compound 4-3 (4 g, 15.1 mmol), compound 4-2 (8.5 g, 18.11 mmol), Pd(PPh3)4 (872 mg, 0.755 mmol), Na2CO3 (4.8 g, 45 mmol), toluene (76 mL), EtOH (20 mL) and distilled water (20 mL), the reaction mixture was stirred for 12 hours at 120°C. After terminating the reaction, the reaction mixture was extracted with EA. The obtained organic layer was dried with anhydrous MgSO4 to remove the remaining moisture, was distillated under reduced pressure to remove the solvent, and was filtered though column to obtain compound C-63 (9 g, 90 %).
Example 5: Preparation of compound C-81
Figure PCTKR2012005841-appb-I000045
Preparation of compound 5-1
After dissolving 1,3-dibromobenzene (58 g, 246 mmol), phenyl boronic acid (20 g, 164 mmol), Pd(PPh3)4 (5.6 g, 4.8 mmol) and Na2CO3 (52 g, 492 mmol) in a mixed solvent of toluene (1 L)/ EtOH (250 mL), the reaction mixture was stirred for 3 hours at 90°C. And then, after terminating the reaction with adding slowly distilled water, the reaction mixture was extracted with EA. The obtained organic layer was dried with anhydrous MgSO4 to remove the remaining moisture, was distillated under reduced pressure to remove the solvent, and was filtered through column to obtain compound 5-1 (26 g, 70 %).
Preparation of compound 5-2
After dissolving compound 5-1 (26 g, 111 mmol) in THF (500 mL), the reaction mixture was cooled to -78°C. After 10 minutes, n-BuLi (66.6 mL, 166.5 mmol, 2.5 M in hexane) was slowly added, and the reaction mixture was stirred for 1 hour. And then, B(OMe)3 (24.7 mL, 222 mmol) was slowly added, and the reaction mixture was stirred for 24 hours. After terminating the reaction, 1M HCl was added, and the reaction mixture was extracted with EA. The obtained organic layer was dried with anhydrous MgSO4 to remove the remaining moisture, was distillated under reduced pressure to remove the solvent, and was recrystallized with MC/hexane to obtain compound 5-2 (14.3 g, 65 %).
Preparation of compound 5-3
After dissolving compound 5-2 (14.3 g, 72 mmol), 1-iodo-4-bromobenzene (30.6 g, 108.3 mmol), Pd(PPh3)4 (3.3 g, 2.9 mmol) and Na2CO3 (22.9 g, 216 mmol) in a mixed solvent of toluene (500 mL)/ EtOH (120 mL), the reaction mixture was stirred for 24 hours at 120°C. And then, after terminating the reaction with adding slowly distilled water, the reaction mixture was extracted with EA. The obtained organic layer was dried with anhydrous MgSO4 to remove the remaining moisture, was distillated under reduced pressure to remove the solvent, and was filtered through column to obtain compound 5-3 (20 g, 90 %).
Preparation of compound 5-4
After dissolving compound 5-3 (25 g, 80.8 mmol) in THF (610 mL), the reaction mixture was cooled to -78°C. After 10 minutes, n-BuLi (48.5 mL, 121.2 mmol, 2.5 M in hexane) was slowly added, and the reaction mixture was stirred for 1 hour. And then, B(OMe)3 (18 mL, 161.7 mmol) was slowly added, and the reaction mixture was stirred for 24 hours. After terminating the reaction, 1M HCl was added, and the reaction mixture was extracted with EA. The obtained organic layer was dried with anhydrous MgSO4 to remove the remaining moisture, was distillated under reduced pressure to remove the solvent, and was recrystallized with MC/hexane to obtain compound 5-4 (16 g, 73 %).
Preparation of compound 5-5
After dissolving compound 5-4 (16 g, 58.3 mmol), 2,4-dichloropyrimidine (11.3 g, 75.8 mmol), Pd(PPh3)4 (3.4 g, 2.91 mmol) and Na2CO3 (15.4 g, 146 mmol) in a mixed solvent of toluene (300 mL)/ EtOH (70 mL), the reaction mixture was stirred for 24 hours at 120°C. And then, after terminating the reaction with adding slowly distilled water, the reaction mixture was extracted with EA. The obtained organic layer was dried with anhydrous MgSO4 to remove the remaining moisture, was distillated under reduced pressure to remove the solvent, and was filtered through column to obtain compound 5-5 (10 g, 50 %).
Preparation of compound C-81
After dissolving NaH (875 mg, 21.8 mmol) in DMF, the solution was stirred. After dissolving compound 1-1 (5 g, 14.5 mmol) in DMF, the solution was added to the NaH solution, and was stirred for 1 hour. After dissolving compound 5-5 (6.11 g, 17.5 mmol) in DMF, the solution was stirred. And then, the mixed solution of compound 1-1 was added to the mixed solution of compound 5-5, and was stirred for 24 hours. After terminating the reaction, the obtained solid was filtered, was washed with EA, and was filtered through column to obtain compound C-81 (5 g, 53 %).
Example 6: Preparation of compound C-104
Figure PCTKR2012005841-appb-I000046
Preparation of compound 6-1
After dissolving dibenzo[b,d]thiophen-4yl boronic acid (30 g, 130 mmol), 3-bromoiodobenzene (34 mL, 260 mmol), Na2CO3 (41 g, 390 mmol) and Pd(PPh3)4 (7.5 g, 6.5 mmol) in a mixed solvent of toluene (300mL)/ EtOH (100 mL)/ purified water (100 mL), the reaction mixture was stirred for 3 hours at 100°C. After terminating the reaction, the reaction mixture was cooled to room temperature, and was left to remove the aqueous layer. The oil layer was concentrated, was triturated with MC, and was filtered to obtain compound 6-1 (33 g, 74 %).
Preparation of compound 6-2
After dissolving compound 6-1 (33 g, 96 mmol) in THF (650 mL), and adding n-BuLi (2.5 M in hexane, 50 mL, 125 mmol) to the reaction mixture at -78°C, the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 2 hours with adding B(Oi-Pr)3 (35 mL, 154 mmol) slowly to the reaction mixture. After quenching the reaction with adding 2 M HCl, the reaction mixture was extracted with distilled water and EA, and was recrystallized with MC and hexane to obtain compound 6-2 (22 g, 76 %).
Preparation of compound 6-3
After dissolving compound 6-2 (17 g, 55 mmol), 3-bromocarbazole (13 mL, 55 mmol), K2CO3 (23 g, 163 mmol) and Pd(PPh3)4 (3 g, 2.7 mmol) in a mixed solvent of toluene (300mL)/ EtOH (100 mL)/ purified water (100 mL), the reaction mixture was stirred for 3 hours at 100°C. After terminating the reaction, the reaction mixture was cooled to room temperature, and was left to remove the aqueous layer. The oil layer was concentrated, was triturated with MC, and was filtered to obtain compound 6-3 (14 g, 62 %).
Preparation of compound C-104
After suspending compound 6-3 (5 g, 12 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (3.2 g, 12 mmol) in DMF (57 mL), 60 % NaH (684 mg, 17.1 mmol) was added at room temperature, and the reaction mixture was stirred for 12 hours. After adding purified water (1 L), the reaction mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/EA, was dissolved with MC, was filtered through silica, and was triturated with MC/n-hexane to obtain compound 104 (1.7 g, 22 %)
The data on the other compounds, which can be easily prepared from the above examples 1-6, are expressed in table 1.
[Table 1]
Figure PCTKR2012005841-appb-I000047
Experimental 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-48 was introduced into another cell as a dopant. The two materials were evaporated at different rates and were deposited in a doping amount of 15 wt% 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 same rates and were deposited in a doping amount of 50 wt% 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 green emission having a luminance of 1000 cd/m2 and a current density of 2.17 mA/cm2 at a driving voltage of 4.4 V.
Experimental 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 Example 1, except for using compound C-44 as a host material, and compound D-1 as a dopant. The produced OLED device showed green emission having a luminance of 2030 cd/m2 and a current density of 4.39 mA/cm2 at a driving voltage of 3.1 V.
Experimental Example 3: Production of an OLED device using the compound according to the present invention
An OLED device was produced in the same manner as in Example 1, except for using compound C-52 as a host material, and compound D-9 as a dopant. The produced OLED device showed green emission having a luminance of 1000 cd/m2 and a current density of 2.35 mA/cm2 at a driving voltage of 3.5 V.
Experimental Example 4: Production of an OLED device using the compound according to the present invention
An OLED device was produced in the same manner as in Example 1, except for using compound C-54 as a host material, and compound D-1 as a dopant. The produced OLED device showed green emission having a luminance of 1050 cd/m2 and a current density of 2.21 mA/cm2 at a driving voltage of 3.8 V.
Experimental Example 5: Production of an OLED device using the compound according to the present invention
An OLED device was produced in the same manner as in Example 1, except for using compound C-56 as a host material, and compound D-1 as a dopant. The produced OLED device showed orange emission having a luminance of 1510 cd/m2 and a current density of 3.41 mA/cm2 at a driving voltage of 2.7 V.
Experimental Example 6: Production of an OLED device using the compound according to the present invention
An OLED device was produced in the same manner as in Example 1, except for using compound C-57 as a host material, and compound D-48 as a dopant. The produced OLED device showed green emission having a luminance of 2160 cd/m2 and a current density of 5.65 mA/cm2 at a driving voltage of 4.1 V.
Experimental Example 7: Production of an OLED device using the compound according to the present invention
An OLED device was produced in the same manner as in Example 1, except for using compound C-59 as a host material, and compound D-48 as a dopant. The produced OLED device showed green emission having a luminance of 1470 cd/m2 and a current density of 3.56 mA/cm2 at a driving voltage of 3.8 V.
Experimental Example 8: Production of an OLED device using the compound according to the present invention
An OLED device was produced in the same manner as in Example 1, except for using compound C-61 as a host material, and compound D-9 as a dopant. The produced OLED device showed green emission having a luminance of 1130 cd/m2 and a current density of 2.69 mA/cm2 at a driving voltage of 2.7 V.
Experimental Example 9: Production of an OLED device using the compound according to the present invention
An OLED device was produced in the same manner as in Example 1, except for using compound C-62 as a host material, and compound D-1 as a dopant. The produced OLED device showed orange emission having a luminance of 890 cd/m2 and a current density of 2.51 mA/cm2 at a driving voltage of 2.6 V.
Experimental Example 10: Production of an OLED device using the compound according to the present invention
An OLED device was produced in the same manner as in Example 1, except for using compound C-68 as a host material, and compound D-48 as a dopant. The produced OLED device showed green emission having a luminance of 1100 cd/m2 and a current density of 3.98 mA/cm2 at a driving voltage of 2.6 V
Experimental Example 11: Production of an OLED device using the compound according to the present invention
An OLED device was produced in the same manner as in Example 1, except for using compound C-81 as a host material, and compound D-1 as a dopant. The produced OLED device showed green emission having a luminance of 1070 cd/m2 and a current density of 2.60 mA/cm2 at a driving voltage of 3.0 V.
Experimental Example 12: Production of an OLED device using the compound according to the present invention
An OLED device was produced in the same manner as in Example 1, except for using compound C-100 as a host material, and compound D-48 as a dopant. The produced OLED device showed green emission having a luminance of 4210 cd/m2 and a current density of 9.29 mA/cm2 at a driving voltage of 4.9 V.
Experimental Example 13: Production of an OLED device using the compound according to the present invention
An OLED device was produced in the same manner as in Example 1, except for using compound C-101 as a host material, and compound D-1 as a dopant. The produced OLED device showed orange emission having a luminance of 3630 cd/m2 and a current density of 9.75 mA/cm2 at a driving voltage of 4.0 V.
Experimental Example 14: Production of an OLED device using the compound according to the present invention
An OLED device was produced in the same manner as in Example 1, except for using compound C-102 as a host material, and compound D-1 as a dopant. The produced OLED device showed green emission having a luminance of 1870 cd/m2 and a current density of 4.00 mA/cm2 at a driving voltage of 3.7 V.
Experimental Example 15: Production of an OLED device using the compound according to the present invention
An OLED device was produced in the same manner as in Example 1, except for using compound C-104 as a host material, and compound D-9 as a dopant. The produced OLED device showed orange emission having a luminance of 1010 cd/m2 and a current density of 2.42 mA/cm2 at a driving voltage of 2.6 V.
Comparative Example 1: Production of an OLED device using conventional electroluminescent compounds
An OLED device was produced in the same manner as that of Example 1, except that a light-emitting layer having a thickness of 30 nm was deposited on the hole transport layer by using 4,4’-N,N’-dicarbazol-biphenyl as a host material and Ir(ppy)3 as a dopant and that a hole blocking layer having a thickness of 10 nm was deposited by using aluminum(III) bis(2-methyl-8-quinolinato)-4-phenylphenolate.
The produced OLED device showed green emission having a luminance of 1000 cd/m2 and a current density of 2.89 mA/cm2 at a driving voltage of 4.8 V.
The organic electroluminescence 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 green or orange light emitting host material not only has excellent luminous characteristics, but also induces an increase in power efficiency by reducing the driving voltage.

Claims (6)

  1. A compound represented by the following formula 1:
    Figure PCTKR2012005841-appb-I000048
    wherein
    L1 and L2 each independently represent a single bond, a substituted or unsubstituted 3- to 30-membered heteroarylene group, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (C6-C30)cycloalkylene group;
    X1 and X2 each independently represent CR’ or N;
    Y represents -O-, -S-, -CR5R6- or -NR7-;
    Ar1, Ar2 and R’ 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 3- to 30-membered heteroaryl group;
    R1 to R4 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, -NR11R12, -SiR13R14R15, -SR16, -OR17, a cyano group, a nitro group, or a hydroxyl 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;
    R5 to R7 and R11 to R17 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 5- to 7-membered heterocycloalkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl 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 and c each independently represent an integer of 1 to 4; where a or c is an integer of 2 or more, each of R1 or each of R3 is the same or different;
    b and d each independently represent an integer of 1 to 3; where b or d is an integer of 2 or more, each of R2 or each of R4 is the same or different; and
    the heteroarylene group, the heterocycloalkyl group and the heteroaryl 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 aryl(ene) group, the substituted heteroaryl(ene) group, the substituted cycloalkyl(ene) group, the substituted heterocycloalkyl group, and the substituted aralkyl group in L1, L2, R’, Ar1, Ar2, R1 to R4, R5 to R7 and R11 to R17 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 (C3-C30)cycloalkyl group; a 5- to 7-membered heterocycloalkyl 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; an N-carbazolyl 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 and L2 each independently represent a single bond, a 3- to 30-membered heteroarylene group, or a (C6-C30)arylene group;
    X1 and X2 each independently represent CR’ or N;
    Y represents -O-, -S-, -CR5R6- or -NR7-;
    Ar1, Ar2 and R’ each independently represent hydrogen, a (C1-C30)alkyl group, a (C6-C30)aryl group, or a 3- to 30-membered heteroaryl group;
    R1 to R4 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group, a (C6-C30)aryl group, a 3- to 30-membered heteroaryl group, -NR11R12, or -SiR13R14R15; or R3 is 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;
    R5 to R7 and R11 to R17 each independently represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl group, a (C6-C30)aryl group, or a 3- to 30-membered heteroaryl group; and
    the arylene group and the heteroarylene group in L1 and L2, and the alkyl group, the aryl group, and the heteroaryl group in Ar1, Ar2, R’, R1 to R4, R5 to R7 and R11 to R17 each independently 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 substituted or unsubstituted with a (C6-C30)aryl; 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; an N-carbazolyl group; a di(C1-C30)alkylamino group; a di(C6-C30)arylamino group; a (C1-C30)alkyl(C6-C30)aryl amino group; and a (C1-C30)alkyl(C6-C30)aryl group.
  4. The compound according to claim 1, wherein
    L1 and L2 each independently represent a single bond, phenylene, biphenylene, terphenylene, indenylene, fluorenylene, triphenylenylene, pyrenylene, perylenylene, crycenylene, naphthacenylene, fluorantenylene, thiophenylene, pyrrolylene, pyrazolylene, thiazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, furazanylene, pyridylene, benzofuranylene, benzothiophenylene, indolylene, benzoimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzoxazolylene, benzothiadiazolylene, dibenzofuranylene, or dibenzothiophenylene;
    Ar1, Ar2 and R’ each independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifuloroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, fluorenyl, fluorantenyl, terphenyl, pyrenyl, crycenyl, naphthacenyl, perylenyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, quinolyl, triazinyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, quinoxalinyl, or N-carbazolyl;
    R1 to R4 each independently represent hydrogen, deuterium, chloro, fluoro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifuloroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, anthryl, biphenyl, fluorenyl, fluorantenyl, triphenylenyl, pyrenyl, crycenyl, naphthacenyl, perylenyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, indenyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, N-carbazolyl, dimethylamino, diethylamino, methylphenylamino, diphenylamino, trimethylsilyl, triethylsilyl, tripropylsilyl, tri(t-butyl)silyl, t-butyldimethylsilyl, dimethylphenylsilyl, or triphenylsilyl;
    a to d each independently represent 1 or 2;
    the substituents in Ar1, Ar2, R’, and R1 to R4 each independently can be substituted with at least one selected from the group consisting of deuterium, chloro, fluoro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifuloroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, fluorantenyl, triphenylenyl, pyrenyl, crycenyl, naphthacenyl, perylenyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, benzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzothiophenyl, pyrazolyl, indolyl, carbazolyl, N-carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, dimethylamino, diethylamino, methylphenylamino, diphenylamino, trimethylsilyl, triethylsilyl, tripropylsilyl, tri(t-butyl)silyl, t-butyldimethylsilyl, dimethylphenylsilyl, methyldiphenylsilyl, triphenylsilyl, and N-phenylcarbazolyl.
  5. The compound according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
    Figure PCTKR2012005841-appb-I000049
    Figure PCTKR2012005841-appb-I000050
    Figure PCTKR2012005841-appb-I000051
    Figure PCTKR2012005841-appb-I000052
    Figure PCTKR2012005841-appb-I000053
    Figure PCTKR2012005841-appb-I000054
    Figure PCTKR2012005841-appb-I000055
    Figure PCTKR2012005841-appb-I000056
    Figure PCTKR2012005841-appb-I000057
    Figure PCTKR2012005841-appb-I000058
    Figure PCTKR2012005841-appb-I000059
    Figure PCTKR2012005841-appb-I000060
    Figure PCTKR2012005841-appb-I000061
    Figure PCTKR2012005841-appb-I000062
    Figure PCTKR2012005841-appb-I000063
    Figure PCTKR2012005841-appb-I000064
    Figure PCTKR2012005841-appb-I000065
  6. An organic electroluminescent device comprising the compound according to claim 1.
PCT/KR2012/005841 2011-07-21 2012-07-20 9h-carbazole compounds and electroluminescent devices involving them Ceased WO2013012298A1 (en)

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