WO2012165832A1 - Novel compounds for organic electronic material and organic electroluminescent device using the same - Google Patents

Novel compounds for organic electronic material and organic electroluminescent device using the same Download PDF

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WO2012165832A1
WO2012165832A1 PCT/KR2012/004214 KR2012004214W WO2012165832A1 WO 2012165832 A1 WO2012165832 A1 WO 2012165832A1 KR 2012004214 W KR2012004214 W KR 2012004214W WO 2012165832 A1 WO2012165832 A1 WO 2012165832A1
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group
substituted
unsubstituted
aryl
alkyl
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PCT/KR2012/004214
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French (fr)
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Hee-Sook Kim
Nam-Kyun Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority to JP2014513430A priority Critical patent/JP2014522400A/ja
Priority to CN201280037304.4A priority patent/CN103717603A/zh
Publication of WO2012165832A1 publication Critical patent/WO2012165832A1/en

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Definitions

  • the present invention relates to novel compounds for organic electronic material and an 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 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)pic
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • BCP bathocuproine
  • BAlq aluminum(III)bis(2-methyl-8-quinolinate)(4-phenylphenolate)
  • Pioneer (Japan) et al. developed a high performance organic EL device employing a derivative of BAlq as a host material.
  • WO 2006/049013 discloses compounds for organic electroluminescent materials having a condensed bicyclic group as a backbone structure. However, it does not disclose a compound having a nitrogen-containing condensed bicyclic group substituted with a carbazole group which is fused with an aromatic ring-fused heterocycloalkyl or cycloalkyl group.
  • the objective of the present invention is to provide a compound for organic electronic material which has an excellent structure imparting high luminous efficiency and a long operation lifetime to a device, and having proper color coordination; and an organic electroluminescent device having high efficiency and a long lifetime, using said compounds.
  • L 1 and L 2 each independently represent a single bond, a substituted or
  • X 1 represents CH or N
  • Y 1 to Y 3 each independently represent -O-, -S-, -CR 6 R 7 - or -NR 8 -,
  • R 1 to R 5 each independently represent hydrogen, deuterium, a halogen, a
  • R 6 to R 8 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) via a substituted or unsubstituted (C3-C30)alkylene or (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
  • a, b, c and e each independently represent an integer of 1 to 4;
  • a, b, c or e is an integer of 2 or more, each of R 1 , each of R 2 , each of R 3 or each of R 5 is the same or different;
  • d represents an integer of 1 to 3; where d is an integer of 2 or more,
  • each of R 4 is the same or different.
  • the compounds for organic electronic materials according to the present invention can manufacture an organic electroluminescent device which has high luminous efficiency and a long operation lifetime.
  • the compounds for organic electronic materials 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 a compound for organic electronic materials represented by the above formula 1 and an organic electroluminescent 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., but are not limited thereto;
  • “(C2-C30) alkenyl(ene)” is meant to be a linear or branched alkenyl(ene) 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., but are not limited thereto; “(C2-C30)alkynyl” is meant to be
  • 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 are preferably a single bond, a (C6-C12)arylene group substituted or unsubstituted with a (C1-C6)alkyl or an unsubstituted (C1-C6)cycloalkylene, more preferably a single bond, phenylene, biphenylene, dimethylphenylene or cyclohexylene.
  • Y 1 to Y 3 each independently represent -O-, -S-,
  • R 6 and R 8 each independently are preferably 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; or are linked to an adjacent substituent(s) to form a spiro ring or a fused spiro ring, more preferably deuterium, a halogen, a (C1-C6)alkyl group, a (C6-C20)aryl group substituted or unsubstituted with a (C6-C12)aryl, or a 5- to 21-membered heteroaryl group substituted or unsubstituted with a (C6-C12)aryl; or are linked to an adjacent substituent(s) to form a spir
  • R 1 to R 5 each independently are preferably 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, N-carbazolyl, -NR 11 R 12 or -SiR 13 R 14 R 15 ; or are linked to an adjacent substituent(s) via a substituted or unsubstituted (C3-C30)alkylene or (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur, wherein R 11 to R 15 each independently are preferably a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubsti
  • R 1 to R 5 each independently are more preferably an unsubstituted (C6-C20)aryl group, an unsubstituted 5- to 21-membered heteroaryl group, -NR 11 R 12 or -SiR 13 R 14 R 15 ; or are linked to an adjacent substituent(s) via a substituted or unsubstituted (C3-C30)alkylene or (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring, even more preferably phenyl, carbazolyl, diphenylamino or methyldiphenylsilyl; or are linked to an adjacent substituent(s) via a substituted or unsubstituted (C3-C30)alkylene or (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring.
  • the representative compounds of the present invention include the following compounds, but are not limited thereto:
  • the compounds for organic electronic materials according to the present invention can be prepared according to the following reaction scheme.
  • R 1 to R 5 , Y 1 to Y 3 , X 1 , L 1 , L 2 , a, b, c, d and e are as defined in formula 1 above, and X represents a halogen.
  • the present invention provides an organic electroluminescent device comprising the compound of formula 1.
  • 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 compound of formula 1 is comprised as a host material.
  • a phosphorescent dopant which is used for an organic electroluminescent device together with the host material according to the present invention, 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 may be linked to each other via a (C3-C12)alkylene group or (C3-C12)alkenylene group with or without a fused ring, to form a mono- or polycyclic, 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 5- or 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 (C2-C30)alkylene group or (C2-C30)alkenylene group to form a spiro ring or a fused ring or may be linked to R 207 or R 208 via a (C2-C30)alkylene group or (C2-C30)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 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 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.
  • Example 1 Production of an OLED device using the compound according to the present invention
  • 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(N1-(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 60nm 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-16 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% to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
  • the produced OLED device showed red emission having a luminance of 1,030 cd/m 2 and a current density of 10.0 mA/cm 2 at a driving voltage of 4.1 V. Further, the minimum time taken to be reduced to 90 % of the luminance at a luminance of 5,000 nit was 30 hours.
  • 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-48 as a host material, and compound D-11 as a dopant.
  • the produced OLED device showed red emission having a luminance of 1,030 cd/m 2 and a current density of 12.7 mA/cm 2 at a driving voltage of 4.2 V. Further, the minimum time taken to be reduced to 90 % of the luminance at a luminance of 5,000 nit was 100 hours.
  • 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-51 as a host material, and compound D-11 as a dopant.
  • the produced OLED device showed red emission having a luminance of 1,010 cd/m 2 and a current density of 13.7 mA/cm 2 at a driving voltage of 4.5 V. Further, the minimum time taken to be reduced to 90 % of the luminance at a luminance of 5,000 nit was 100 hours.
  • 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-94 as a host material, and compound D-11 as a dopant.
  • the produced OLED device showed red emission having a luminance of 1,060 cd/m 2 and a current density of 12.2 mA/cm 2 at a driving voltage of 4.2 V. Further, the minimum time taken to be reduced to 90 % of the luminance at a luminance of 5,000 nit was 40 hours.
  • 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-96 as a host material, and compound D-7 as a dopant.
  • the produced OLED device showed red emission having a luminance of 1,010 cd/m 2 and a current density of 9.8 mA/cm 2 at a driving voltage of 3.9 V. Further, the minimum time taken to be reduced to 90 % of the luminance at a luminance of 5,000 nit was 20 hours.
  • 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 (CBP) as a host material and compound D-11 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.
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • the produced OLED device showed red emission having a luminance of 1,000 cd/m 2 and a current density of 20.0 mA/cm 2 at a driving voltage of 8.2V. Further, the minimum time taken to be reduced to 90 % of the luminance at a luminance of 5,000nit was 10 hours.
  • the compounds for organic electronic material 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. In addition, while the OLED device using conventional compounds for organic electronic material needed hole blocking layer, the hole blocking layer is not necessary in the OLED device using the compounds according to the present invention.

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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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CN201280037304.4A CN103717603A (zh) 2011-05-30 2012-05-29 用于有机电子材料的新化合物以及使用该化合物的有机电致发光器件

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WO2013088973A1 (ja) * 2011-12-15 2013-06-20 新日鉄住金化学株式会社 有機電界発光素子
WO2014057659A1 (ja) * 2012-10-12 2014-04-17 出光興産株式会社 化合物及びそれを用いた有機エレクトロルミネッセンス素子
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JP2013040105A (ja) * 2011-07-15 2013-02-28 Idemitsu Kosan Co Ltd 含窒素芳香族複素環誘導体およびそれを用いた有機エレクトロルミネッセンス素子
WO2013088973A1 (ja) * 2011-12-15 2013-06-20 新日鉄住金化学株式会社 有機電界発光素子
WO2014057659A1 (ja) * 2012-10-12 2014-04-17 出光興産株式会社 化合物及びそれを用いた有機エレクトロルミネッセンス素子
CN103965869A (zh) * 2013-01-30 2014-08-06 海洋王照明科技股份有限公司 红光有机电致发光材料及其制备方法和应用
CN103965874A (zh) * 2013-01-30 2014-08-06 海洋王照明科技股份有限公司 红光有机电致发光材料及其制备方法和应用
CN103965871A (zh) * 2013-01-30 2014-08-06 海洋王照明科技股份有限公司 红光有机电致发光材料及其制备方法和应用
CN103965872A (zh) * 2013-01-30 2014-08-06 海洋王照明科技股份有限公司 红光有机电致发光材料及其制备方法和应用
WO2015099486A1 (en) * 2013-12-27 2015-07-02 Rohm And Haas Electronic Materials Korea Ltd. Novel organic electroluminescent compounds and organic electroluminescent device comprising the same
CN105849107A (zh) * 2013-12-27 2016-08-10 罗门哈斯电子材料韩国有限公司 新颖有机电致发光化合物和包括所述化合物的有机电致发光装置
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CN105849107B (zh) * 2013-12-27 2019-03-01 罗门哈斯电子材料韩国有限公司 有机电致发光化合物和包括所述化合物的有机电致发光装置
WO2016048109A1 (en) * 2014-09-26 2016-03-31 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound, and organic electroluminescent material and organic electroluminescent device comprising the same
US10886474B2 (en) 2014-09-26 2021-01-05 Rohm And Haas Electronic Materials Korea Ltd Organic electroluminescent compound, and organic electroluminescent material and organic electroluminescent device comprising the same
WO2017016667A1 (de) * 2015-07-29 2017-02-02 Merck Patent Gmbh Verbindungen mit fluoren-strukturen
US11201296B2 (en) 2015-07-29 2021-12-14 Merck Patent Gmbh Compounds having fluorene structures

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