US20190367491A1 - Compound and organic electronic device comprising the same - Google Patents

Compound and organic electronic device comprising the same Download PDF

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US20190367491A1
US20190367491A1 US16/429,160 US201916429160A US2019367491A1 US 20190367491 A1 US20190367491 A1 US 20190367491A1 US 201916429160 A US201916429160 A US 201916429160A US 2019367491 A1 US2019367491 A1 US 2019367491A1
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Chi-Chung Chen
Shwu-Ju Shieh
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Shanghai Nichem Fine Chemical Co Ltd
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Shanghai Nichem Fine Chemical Co Ltd
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Definitions

  • the present invention relates to a novel compound and an organic electronic device using the same, more particularly to a novel compound as an electron transport material and an organic electronic device using the same.
  • organic electronic devices that make use of organic materials have been energetically developed.
  • organic electronic devices include organic light emitting devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors.
  • OLEDs organic light emitting devices
  • organic phototransistors organic phototransistors
  • organic photovoltaic cells organic photovoltaic cells
  • organic photodetectors organic photodetectors
  • OLED was initially invented and proposed by Eastman Kodak Company through a vacuum evaporation method.
  • Dr. Ching Tang and Steven VanSlyke of Kodak Company deposited an electron transport material such as tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq 3 ) on a transparent indium tin oxide glass (abbreviated as ITO glass) formed with a hole transport layer of organic aromatic diamine thereon, and subsequently deposited a metal electrode onto an electron transport layer to complete the fabrication of the OLED.
  • OLEDs have attracted lots of attention due to their numerous advantages, such as fast response speed, light weight, compactness, wide viewing angle, high brightness, higher contrast ratio, no need of backlight, and low power consumption. However, the OLEDs still have the problems such as low efficiency.
  • a modified OLED 1 may have a structure of a substrate 11 , an anode 12 , a hole injection layer 13 (abbreviated as HIL), a hole transport layer 14 (abbreviated as HTL), an emission layer 15 (abbreviated as EL), an electron transport layer 16 (abbreviated as ETL), an electron injection layer 17 (abbreviated as EIL), and a cathode 18 stacked in sequence.
  • HIL hole injection layer 13
  • HTL hole transport layer 14
  • EL emission layer 15
  • ETL electron transport layer 16
  • EIL electron injection layer 17
  • ETL for OLEDs examples include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3,3′-[5′-[3-(3-pyridinyl)phenyl][1,1′:3′,1′′-terphenyl]-3,3′′-diyl]bispyridine (TmPyPb), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane (3TPYMB), 1,3-bis(3,5-dipyrid-3-yl-phenyl)benzene (BmPyPb), and 9,10-bis(3-(pyridin-3-yl)phenyl)anthracene (DPyPA).
  • BCP 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline
  • the present invention provides a novel compound to mitigate or obviate the problems in the prior art.
  • An objective of the present invention is to provide a novel compound useful for an organic electronic device.
  • Another objective of the present invention is to provide an organic electronic device using the novel compound, so as to improve the luminous efficacy and external quantum efficiency of the organic electronic device.
  • G 1 and G 2 are each independently selected from the group consisting of:
  • G 1 and G 2 may be the same or different, j is an integer from 1 to 2, and k is an integer from 0 to 2.
  • said G 11 and G 12 are each independently selected from the group consisting of:
  • G 11 and G 12 may be the same or different;
  • R 1 to R 3 are each independently selected from the group consisting of: a deuterium atom, a halo group, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, and an alkynyl group having 2 to 6 carbon atoms;
  • n1 is an integer from 0 to 5
  • n2 is an integer from 0 to 4
  • n3 is an integer from 0 to 7.
  • the novel compound is useful to improve the luminous efficacy and EQE of the organic electronic device, such that the performance of the organic electronic device can be improved.
  • the compound may be represented by any one of the following Formulae (I-I) to (I-VI):
  • G 11 and G 12 are each independently selected from the group consisting of:
  • G 11 and G 12 are each independently selected from the group consisting of:
  • both or either of G 11 and G 12 is a fully deuterated substitution group such as fully deuterated phenyl group (phenyl-D 5 ). That is, R 1 to R 3 are each a deuterium atom, n1 is an integer 5, n2 is an integer 4, and n3 is an integer 7.
  • G 1 and G 2 may be each independently selected from the group consisting of:
  • j is the integer 1 and k is the integer 0. In another embodiment, j is the integer 1 and k is the integer 1.
  • said halo group may be a fluoro group, a chloro group, a bromo group, or an iodo group.
  • said alkyl group having 1 to 6 carbon atoms may be, but is not limited to, a methyl group, an ethyl group, a propyl group, or a butyl group.
  • said alkenyl group having 2 to 6 carbon atoms may be, but is not limited to, a vinyl group, a propenyl group, or a butenyl group.
  • said alkenyl group having 2 to 6 carbon atoms may be, but is not limited to, an ethynyl group, a propynyl group, or a butynyl group.
  • the compound may be any one of:
  • the present invention also provides an organic electronic device, comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode.
  • the organic layer comprises the novel compound as described above.
  • the novel compound may be, but is not limited to, any one of Compounds 1 to 404.
  • the organic electronic device is an organic light emitting device (OLED).
  • OLED organic light emitting device
  • the organic light emitting device may comprise:
  • the organic layer may be the electron transport layer, i.e., the electron transport layer comprises an electron transport material which is the novel compound as stated above.
  • the electron transport layer may be a single-layered configuration or a multi-layered configuration disposed between the emission layer and the electron injection layer.
  • the electron transport layer is the multi-layered configuration, e.g., the electron transport layer comprises a first electron transport layer and a second electron transport layer
  • the first electron transport material of the first electron transport layer may be made of a single novel compound
  • the second electron transport material of the second electron transport layer may be made of another single novel compound or any single conventional compound.
  • the first electron transport material of the first electron transport layer may be made of a novel compound in combination with another single novel compound or any single conventional compound, and so as the second electron transport material.
  • Said first and/or second electron transport layer comprises the novel compound such as Compounds 1 to 404.
  • the OLEDs using the novel compound as the electron transport material can have an improved luminous efficacy and external quantum efficiency compared to the commercial OLEDs using known electron transport materials of ETL, such as BCP, TmPyPb, TPBi, 3TPYMB, BmPyPb, and DPyPA.
  • the OLED comprises a hole blocking layer (HBL), formed between the electron transport layer and the emission layer, to block holes overflow from the emission layer to the electron transport layer.
  • HBL hole blocking layer
  • the organic layer may be the hole blocking layer, i.e., the hole blocking layer comprises a hole blocking material which is the novel compound as stated above. More specifically, said hole blocking layer comprises the novel compound such as Compounds 1 to 404.
  • the OLEDs using the novel compound as the hole blocking material can have an improved efficiency compared to commercial OLEDs using known hole blocking materials of HBL, such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 2,3,5,6-tetramethyl-phenyl-1,4-(bis-phthalimide) (TMPP).
  • BCP 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline
  • TMPP 2,3,5,6-tetramethyl-phenyl-1,4-(bis-phthalimide)
  • the hole injection layer may be a two-layered structure, i.e., the OLED comprises a first hole injection layer and a second hole injection layer disposed between the first electrode and the hole transport layer.
  • Said first and second hole injection layers may be made of, for example, but not limited to: polyaniline, polyethylenedioxythiophene, 4,4′,4′′-Tris[(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), or N 1 ,N 1′ -(biphenyl-4,4′-diyl)bis(N′-(naphthalen-1-yl)-N 4 ,N 4′ -diphenylbenzene-1,4-diamine).
  • m-MTDATA 4,4′,4′′-Tris[(3-methylphenyl)phenylamino]triphenylamine
  • m-MTDATA 4,4′,4′′-Tris[(3-methylphenyl)phenylamino]triphenylamine
  • the hole transport layer may be a two-layered structure, i.e., the OLED comprises a first hole transport layer and a second hole transport layer disposed between the two-layered hole injection layer and the emission layer.
  • Said first and second hole transport layers may be made of, for example, but not limited to: 1,1-bis[(di-4-tolylamino)phenylcyclohexane](TAPC), a carbazole derivative such as N-phenyl carbazole, and N 4 ,N 4′ -di(naphthalen-1-yl)-N 4 ,N4′-diphenylbiphenyl-4,4′-diamine (NPB).
  • the emission layer can be made of an emission material including a host and a dopant.
  • the host of the emission material is, for example, but not limited to, 9-(4-(naphthalen-1-yl)phenyl)-10-(naphthalen-2-yl) anthracene.
  • the dopant of the emission material is, for example, but not limited to: organometallic compounds of iridium (II) having quinoline derivative ligands or isoquinoline derivative ligands; an osmium complex; or a platinum complex.
  • the dopant of the emission material is, for example, but not limited to: diaminofluorenes; diaminoanthracenes; or organometallic compounds of iridium (II) having phenylpyridine ligands.
  • the dopant of the emission material is, for example, but not limited to: an aminoperylene derivative; a diaminochrysene; diaminopyrenes; or organicmetallic compounds of iridium (II) having pyridinato picolinate ligands.
  • the OLED can emit lights in red, green or blue.
  • the OLED comprises an electron blocking layer, formed between the hole transport layer and the emission layer, to block electrons overflow from the emission layer to the hole transport layer.
  • Said electron blocking layer may be made of 9,9′-[1,1′-biphenyl]-4,4′-diylbis-9H-carbazole (CBP) or 4,4′,4′′-tri(N-carbazolyl)-triphenylamine (TCTA), but it is not limited thereto.
  • the OLED In the presence of such a hole blocking layer and/or an electron blocking layer in an OLED, the OLED has a higher luminous efficiency compared to a typical OLED.
  • Said electron injection layer may be made of an electron injection material, for example, but not limited to (8-oxidonaphthalen-1-yl)lithium(II).
  • Said first electrode is, for example, but not limited to, an indium-doped tin oxide electrode.
  • Said second electrode has a work function lower than that of the first electrode.
  • the second electrode is, for example, but not limited to, an aluminum electrode, an indium electrode, or a magnesium electrode.
  • FIG. 1 illustrates a schematic cross-sectional view of an OLED.
  • the purified product was identified as Intermediate A-1 by a field desorption mass spectroscopy (FD-MS) analysis.
  • FD-MS analysis C 15 H 10 Br 2 O: theoretical value of 366.05 and observed value of 366.05.
  • Step A-2 Synthesis of Intermediate A-2
  • Step B-1 Synthesis of Spiro Alcohol
  • Intermediates B1 to B4 In addition to the Intermediates B1 to B4, one person skilled in the art can adopt other Reactants An similar to Reactants A1 to A4 to react with Intermediate A to synthesize other desired Intermediates Bn through Scheme II. Applicable modifications of Intermediate Bn may be, for example, but are not limited to, Intermediates B5 to B7 as follows.
  • Intermediates C1 to C3 In addition to the Intermediates C1 to C3, one person skilled in the art can undergo a similar reaction of Scheme III to synthesize other desired Intermediates Cn, for example, but are not limited to, Intermediates C4 to C7. Said Intermediates C4 to C7 may be obtained from Intermediates B4 to B7 through a reaction of Scheme III, respectively.
  • Reactants Bn such as Reactants B1 to B20, applicable to prepare a novel compound were listed in Table 4. Most of Reactants B1 to B7, B9 to B18 and B20 were purchased from Sigma-Aldrich.
  • Reactant B8 could be synthesized by Scheme IV.
  • Intermediate Cn may be any one of the foresaid Intermediates C1 to C3 as listed in Table 3 and Intermediates C4 to C7
  • Reactant Bn may be any one of Reactants B1 to B20 as listed in Table 4, but it is not limited thereto.
  • ITO substrate A glass substrate coated with ITO layer (abbreviated as ITO substrate) in a thickness of 1500 ⁇ was placed in distilled water containing a detergent dissolved therein, and was ultrasonically washed.
  • the detergent was a product manufactured by Fischer Co., and the distilled water was distilled water filtered twice through a filter (Millipore Co.). After the ITO layer had been washed for 30 minutes, it was ultrasonically washed twice with distilled water for 10 minutes. After the completion of washing, the glass substrate was ultrasonically washed with isopropyl alcohol, acetone and methanol solvents and then dried, after which it was transported to a plasma cleaner. Then the substrate was cleaned with oxygen plasma for 5 min, and then transferred to a vacuum evaporator.
  • the ITO substrate was deposited with a first hole injection layer (HIL-1), a second hole injection layer (HIL-2), a hole transporting layer (HTL), a blue/green/red emission layer (BEL/GEL/REL), an electron transporting layer (ETL), an electron injection layer (EIL), and a cathode (Cthd).
  • HIL-1 hole injection layer
  • HIL-2 hole injection layer
  • HTL hole transporting layer
  • BEL/GEL/REL blue/green/red emission layer
  • ETL electron transporting layer
  • EIL electron injection layer
  • Cthd cathode
  • HI and HI-D were materials for forming HIL-1; HI was a material for forming HIL-2; HT was a material for forming HTL; novel compounds of the present invention were materials for forming ETL; Liq was a material for forming ETL and EIL.
  • RH/GH/BH were each a host material for forming REL/GEL/BEL, and RD/GD/BD were each a dopant for forming REL/GEL/BEL.
  • Table 7 The detailed chemical structures of foresaid commercial materials used in the OLED devices were listed in Table 7.
  • red OLED device To prepare the red OLED device, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 8, and the materials and the thicknesses of the organic layers in red OLED devices were also listed in Table 8.
  • red, green, and blue OLED devices were measured by PR650 as photometer and Keithley 2400 as power supply. Color coordinates (x,y) were determined according to the CIE chromaticity scale (Commission Internationale de L'Eclairage, 1931). The results were shown in Table 11. For the blue OLED devices, the data were collected at 1000 nits. For the green OLED devices, the data were collected at 3000 nits. And for the red OLED devices, the data were collected at 3000 nits.

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