WO2014163211A1 - Organic compound and organic light-emitting device - Google Patents

Organic compound and organic light-emitting device Download PDF

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Publication number
WO2014163211A1
WO2014163211A1 PCT/JP2014/060350 JP2014060350W WO2014163211A1 WO 2014163211 A1 WO2014163211 A1 WO 2014163211A1 JP 2014060350 W JP2014060350 W JP 2014060350W WO 2014163211 A1 WO2014163211 A1 WO 2014163211A1
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Prior art keywords
group
compound
emitting device
organic
organic light
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PCT/JP2014/060350
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English (en)
French (fr)
Inventor
Naoki Yamada
Jun Kamatani
Akihito Saitoh
Yosuke Nishide
Masanori Muratsubaki
Ryuji Ishii
Koichi Ishige
Takayuki Ito
Norifumi Kajimoto
Nobutaka Mizuno
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Canon Inc
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Canon Inc
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Application filed by Canon Inc filed Critical Canon Inc
Priority to EP22171994.1A priority Critical patent/EP4075533B1/en
Priority to US14/766,298 priority patent/US9911921B2/en
Priority to EP14778819.4A priority patent/EP2981993B1/en
Publication of WO2014163211A1 publication Critical patent/WO2014163211A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
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    • C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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    • G03G15/04036—Details of illuminating systems, e.g. lamps, reflectors
    • G03G15/04045—Details of illuminating systems, e.g. lamps, reflectors for exposing image information provided otherwise than by directly projecting the original image onto the photoconductive recording material, e.g. digital copiers
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    • G—PHYSICS
    • G06—COMPUTING OR CALCULATING; COUNTING
    • G06F—ELECTRIC DIGITAL DATA PROCESSING
    • G06F3/00—Input arrangements for transferring data to be processed into a form capable of being handled by the computer; Output arrangements for transferring data from processing unit to output unit, e.g. interface arrangements
    • G06F3/01—Input arrangements or combined input and output arrangements for interaction between user and computer
    • G06F3/03—Arrangements for converting the position or the displacement of a member into a coded form
    • G06F3/041—Digitisers, e.g. for touch screens or touch pads, characterised by the transducing means
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    • H05B45/00—Circuit arrangements for operating light-emitting diodes [LED]
    • H05B45/60—Circuit arrangements for operating LEDs comprising organic material, e.g. for operating organic light-emitting diodes [OLED] or polymer light-emitting diodes [PLED]
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    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
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    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
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    • H10K50/14—Carrier transporting layers
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    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Definitions

  • the present invention relates to an organic compound
  • An organic light-emitting device is an electronic
  • the device including a pair of electrodes and an organic compound layer placed between the electrodes.
  • An electron and a hole are injected from the pair of electrodes, the electron and the hole recombine in the organic compound layer to produce an exciton of a luminous organic compound, and the organic light- emitting device emits light when the exciton returns to its ground state.
  • Patent Literature 1 proposes that an improvement in
  • hole transport property be achieved by forming a hole transport layer from a mixture of different hole
  • Patent Application is directed to transportable materials.
  • Patent Application is directed to transportable materials.
  • Literature 2 discloses an organic light-emitting device including a layer obtained by doping a tertiary amine compound with rubrene or an anthracene compound.
  • Patent Literature 3 and Patent Literature 4 propose compounds shown below. [0005]
  • an object of the present invention is to provide an organic light-emitting device capable of outputting light with high efficiency and high
  • embodiment of the present invention includes: an anode; a cathode; an emission layer placed between the anode and the cathode; and an organic compound layer placed between the anode and the emission layer, wherein the organic compound layer contains the following compound A and compound B:
  • Compound A an organic compound free of a nitrogen atom and a metal atom, the compound having SP 2 carbon atoms and SP 3 carbon atoms, and having a ratio of the number of the SP 3 carbon atoms to the number of the SP 2 carbon atoms of 40% or more;
  • compound of the present invention does not cause association between its molecules and has a wide band gap in a film.
  • FIG. 1 is a schematic sectional view of a display
  • apparatus including an organic light-emitting device and a switching device connected to the organic light- emitting device.
  • the organic light-emitting device of the present invention includes: an anode; a cathode; an emission layer placed between the anode and the cathode; and an organic compound layer placed between the anode and the emission layer.
  • the organic compound layer contains the following compound A and compound B: [Compound A] an aromatic hydrocarbon compound having SP 2 carbon atoms and SP 3 carbon atoms, and having a ratio of the number of the SP 3 carbon atoms to the number of the SP 2 carbon atoms of 40% or more; and
  • specific constructions of the organic light-emitting device include at least the following constructions (A) to (C) .
  • the present invention is not limited to the aspects (A) to (C) .
  • the following aspects (D) and (E) can also be included in the . specific constructions of the organic light-emitting device depending on the compound A in the organic compound layer.
  • the cathode constituting the organic light-emitting device is formed on the substrate as an electrode close to the substrate before the respective layers are formed.
  • the organic compound layer incorporated into the organic light-emitting device as a layer different from the emission layer is a layer formed between the anode and the emission layer as described above.
  • the layer construction of the organic compound layer is not limited to a single layer and may be a laminate formed of multiple layers.
  • the organic compound layer in the organic light-emitting device is
  • a layer having a function of transporting a hole preferably a layer having a function of transporting a hole, and is specifically a hole injection layer, a hole transport layer, or a laminate obtained by
  • the SP 2 carbon atoms in the compound A are carbon atoms for forming an unsaturated carbon-carbon bond
  • (C C) and are carbon atoms constituting mainly the main skeleton of the aromatic hydrocarbon compound.
  • the SP 3 carbon atoms in the compound A are carbon atoms for forming a saturated carbon-carbon bond
  • the compound A is preferably a compound represented by the following general formula
  • ⁇ represents an aryl group (aromatic hydrocarbon group) , an aliphatic condensed polycyclic group, a carbon atom, or an oxygen atom.
  • Examples of .the aryl group represented by Z 1 include: a monovalent aryl group such as a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, an anthryl group, a pyrenyl group, an indacenyl group, an acenaphthenyl group, a
  • phenanthryl group a phenalenyl group, a fluoranthenyl group, an acephenanthryl group, an aceanthryl group, a triphenylenyl group, a chrysenyl group, a naphthacenyl group, a perylenyl group, a pentacenyl group, a
  • biphenyl group, a terphenyl group, or a fluorenyl group and a 2- to 6-valent aryl group derived from the monovalent aryl group (that is, a 2- to 6-valent aryl group obtained by removing 1 to 5 hydrogen atoms from the monovalent aryl group) .
  • Examples of the aliphatic condensed polycyclic group represented by Z i include ring structures listed below.
  • the substituent (aryl group, aliphatic condensed polycyclic group, carbon atom, or oxygen atom) represented by Z i may further have: an alkyl group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group, an octyl group, a 1-adamantyl group, a 2-adamantyl group, a cyclohexyl group, a cyclopentyl group, or a cyclohexylmethyl group; an alkoxy group such as a methoxy group, an ethoxy group, an isopropoxy group, an n-propoxy group, a sec-butoxy group, a tert-butoxy group, or an octoxy group; an aryl group such as a phenyl group or a
  • the alkyl group is preferably an alkyl group having 10 or less carbon atoms such as an isopropyl group, an n-propyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an isoamyl group, an adamantyl group, a cyclohexyl group, a cyclopentyl group, or a cyclohexylmethyl group. Any such substituent promotes the lengthening of the lifetime of the organic light-emitting device because the substituent has good heat stability, plays a
  • a branched alkyl group such as an isopropyl group, a tert-butyl group, an isoamyl group, an adamantyl group, a cyclohexyl group, a cyclopentyl group, or a cyclohexylmethyl group is more preferred.
  • the presence of any such substituent improves the heat stability of the compound itself.
  • the aryl group is preferably substituted with an alkoxy group having 10 or less carbon atoms such as an isopropoxy group, an n- propoxy group, a sec-butoxy group, or a tert-butoxy group as the alkoxy group, and an alkoxy group having a branched alkyl group such as an isopropoxy group, a sec-butoxy group, or a tert-butoxy group is more
  • the halogen atom is preferably fluorine .
  • Ari represents an aryl group, an aliphatic condensed polycyclic group, a carbon atom, or an oxygen atom.
  • Specific examples of the aryl group and aliphatic condensed polycyclic group each represented by Ari are the same as the specific examples of the aryl group and aliphatic condensed polycyclic group each represented by Zi.
  • the aryl group may further have a substituent and specific examples of the substituent are the same as the specific examples of the substituent which the aryl group represented by Zi may further have.
  • Ar x preferably represents a phenyl group having an alkyl group, a fluorenyl group having an alkyl group, a biphenyl group having an alkyl group, or a naphthyl group having an alkyl group.
  • n represents an integer of 1 to 6, provided that when ⁇ represents a carbon atom, n represents an integer of 1 to 4, and when Zi
  • n represents an oxygen atom
  • n represents 1 or 2.
  • structures Ar x ' s in parentheses may be identical to or different from each other.
  • Ar 2 and Ar 3 each represent an aryl group or an aliphatic condensed polycyclic group. Specific examples of the aryl group and
  • aliphatic condensed polycyclic group represented by Ar 2 and Ar 3 are the same as the specific examples of the aryl group and aliphatic condensed polycyclic group each represented by Z in the formula [1].
  • the aryl group may further have a substituent and specific examples of the substituent are the same as the specific examples of the substituent which the aryl group represented by Z ⁇ in the formula [1] may further have.
  • the substituent represented by Ar 2 or Ar 3 in the general formula [2] is preferably a phenyl group having an alkyl group, a fluorenyl group having an alkyl group, a biphenyl group having an alkyl group, or a naphthyl group having an alkyl group.
  • the tertiary amine structure of the compound B refers to a structure formed of a nitrogen atom and three kinds of
  • the compound B is a compound containing one or more tertiary amine structures of this type.
  • the compound may be a low-molecular weight compound or may be a high-molecular weight compound.
  • the compound having a tertiary amine structure serving as the compound B is, for example, a low- molecular weight compound
  • the compound is any one of the compounds listed in the following general formulae
  • Ar 2 i to Ar 27 , Ar 30 to Ar 35 , Ar 38 to Ar 42 , Ar 46 to Ar 5i , Ar 55 to Ar 60 , and Ar 6i to Ar 64 each represent a substituted or unsubstituted, monovalent aryl group, a substituted or unsubstituted, monovalent heterocyclic group, or a substituted or unsubstituted, monovalent alkyl group.
  • m represents an integer of 1 to 5 .
  • the compound is, for example, a
  • polymer compound having any one of the general formulae [11] to [17] as a repeating unit.
  • Examples of the monovalent aryl group include
  • a phenyl group such as a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, an anthryl group, a pyrenyl group, an indacenyl group, an acenaphthenyl group, a
  • phenanthryl group a phenalenyl group, a fluoranthenyl group, an acephenanthryl group, an aceanthryl group, a triphenylenyl group, a chrysenyl group, a naphthacenyl group, a perylenyl group, a pantacenyl group, a
  • biphenyl group a terphenyl group, and a fluorenyl group .
  • Examples of the monovalent heterocyclic group include monovalent substituents such as a thienyl group, a pyrrolyl group, a pyridyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a terthienyl group, a dibenzothiophenyl group, a dibenzofuryl group, and a phenanthryl group.
  • monovalent substituents such as a thienyl group, a pyrrolyl group, a pyridyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a terthienyl group, a dibenzothiophenyl group, a dibenzofuryl group, and a phenanthryl group.
  • Examples of the monovalent alkyl group include
  • alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group, an octyl group, a 1-adamantyl group, and a 2-adamantyl group.
  • an alkyl group having 4 or less carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, or a sec-butyl group is preferred.
  • the monovalent aryl group, the monovalent heterocyclic group, or the monovalent alkyl group may have, there are given, for example: an alkyl group such as a methyl group, an ethyl group, an n- propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group, an octyl group, a 1-adamantyl group, or a 2-adamantyl group; an aryl group such as a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, an anthryl group, a pyrenyl group, an indacenyl group, an acenaphthenyl group, a phenanthryl group, a
  • triphenylenyl group a chrysenyl group, a naphthacenyl group, a perylenyl group, a pentacenyl group, a
  • biphenyl group, a terphenyl group, or a fluorenyl group a heterocyclic group such as a thienyl group, a pyrrolyl group, a pyridyl group, an oxazolyl group, an oxadiazolyl group, an thiazolyl group, a thiadiazolyl group, a terthienyl group, a dibenzothiophenyl group, a dibenzofuryl group, or a phenanthryl group; a heterocyclic group such as a thienyl group, a pyrrolyl group, a pyridyl group, an oxazolyl group, an oxadiazolyl group, an thiazolyl group, a thiadiazolyl group, a terthienyl group, a dibenzothiophenyl group, a dibenzofuryl group, or a phenanthryl group; a
  • substituted amino group such as a dimethylamino group, a diethylamino group, a dibenzylamino group, a
  • dianisoylamino group an alkoxy group such as a methoxy group, an ethoxy group, or a propoxy group (preferably an alkoxy group having 4 or less carbon atoms, e.g., a methoxy group, an ethoxy group, a propoxy group, or an n-butoxy group) ; an aryloxy group such as a phenoxy group; . a halogen atom such as fluorine, chlorine, bromine, or iodine (preferably a fluorine atom) ; and a cyano group.
  • an alkoxy group such as a methoxy group, an ethoxy group, or a propoxy group (preferably an alkoxy group having 4 or less carbon atoms, e.g., a methoxy group, an ethoxy group, a propoxy group, or an n-butoxy group)
  • an aryloxy group such as a phenoxy group
  • Ar 28 , Ar 29 , Ar 36 , Ar 37 , Ar 43 to Ar 45 , Ar 52 to Ar 54 , and Ar 65 to Ar 6 8 each represent a substituted or unsubstituted, divalent aryl group, a substituted or unsubstituted, divalent
  • heterocyclic group or a substituted or unsubstituted, divalent alkyl group.
  • divalent aryl group examples include divalent substituents derived from a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an
  • azulenyl group an anthryl group, a pyrenyl group, an indacenyl group, an acenaphthenyl group, a phenanthryl group, a phenalenyl group, a fluoranthenyl group, an acephenanthryl group, an aceanthryl group, a triphenylenyl group, a chrysenyl group, a naphthacenyl group, a perylenyl group, a pantacenyl group, a
  • biphenyl group a terphenyl group, and a fluorenyl group .
  • Examples of the divalent heterocyclic group include divalent substituents derived from a thienyl group, a pyrrolyl group, a pyridyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a thiadiazolyl group, a terthienyl group, a dibenzothiophenyl group, a dibenzofuryl group, and a phenanthryl group.
  • divalent alkyl group examples include divalent alkyl groups derived from a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n- butyl group, a tert-butyl group, a sec-butyl group, an octyl group, a 1-adamantyl group, and a 2-adamantyl group.
  • a divalent substituent derived from an alkyl group having 4 or less carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, or a sec-butyl group is preferred.
  • the aryl group, the heterocyclic group, or the alkyl group may have, there are given, for example: an alkyl group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group, an octyl group, a 1-adamantyl group, or a 2-adamantyl group; an aryl group such as a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an alkyl group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group, an octyl group, a 1-adamantyl group, or a
  • azulenyl group an anthryl group, a pyrenyl group, an indacenyl group, an acenaphthenyl group, a phenanthryl group, a phenalenyl group, a fluoranthenyl group, an acephenanthryl group, an aceanthryl group, a
  • triphenylenyl group a chrysenyl group, a naphthacenyl group, a perylenyl group, a pentacenyl group, a
  • biphenyl group, a terphenyl group, or a fluorenyl group a heterocyclic group such as a thienyl group, a pyrrolyl group, a pyridyl group, an oxazolyl group, an oxadiazolyl group, an thiazolyl group, a thiadiazolyl group, a terthienyl group, a dibenzothiophenyl group, a dibenzofuryl group, or a . phenanthryl group; a heterocyclic group such as a thienyl group, a pyrrolyl group, a pyridyl group, an oxazolyl group, an oxadiazolyl group, an thiazolyl group, a thiadiazolyl group, a terthienyl group, a dibenzothiophenyl group, a dibenzofuryl group, or a . phenanthryl
  • substituted amino group such as a dimethylamino group, a diethylamino group, a dibenzylamino group, a
  • dianisoylamino group an alkoxy group such as a methoxy group, an ethoxy group, or a propoxy group (preferably an alkoxy group having 4 or less carbon atoms, e.g., a methoxy group, an ethoxy group, a propoxy group, or an n-butoxy group) ; an aryloxy group such as a phenoxy group; a halogen atom such as fluorine, chlorine, bromine, or iodine (preferably a fluorine atom) ; and a cyano group.
  • an alkoxy group such as a methoxy group, an ethoxy group, or a propoxy group (preferably an alkoxy group having 4 or less carbon atoms, e.g., a methoxy group, an ethoxy group, a propoxy group, or an n-butoxy group)
  • an aryloxy group such as a phenoxy group
  • a halogen atom such
  • Ar 2i to Ar 23 may be
  • any one of the combinations of Ar 2 i and Ar 22 , ⁇ 2i and Ar 23 , and Ar 22 and Ar 23 may wind in a ring (that is, for example, Ar 2i and Ar 22 may be bonded to turn into -Ar 2:L -Ar 22 -, thereby forming a ring with N) to form a nitrogen-containing heterocyclic skeleton such as a carbazole skeleton.
  • Ar 24 to Ar 27 may be
  • any one of the combinations of Ar 24 and Ar 25 , and Ar 26 and Ar 27 may wind in a ring to form a nitrogen- containing heterocyclic skeleton such as a carbazole skeleton.
  • Ar 30 to Ar 35 may be any organic radical having the general formula [0047] in the general formula [13], Ar 30 to Ar 35 may be any organic radical having the general formula [0047] in the general formula [13], Ar 30 to Ar 35 may be any organic radical having the general formula [0047] in the general formula [13], Ar 30 to Ar 35 may be any organic radical having the general formula [0047] in the general formula [13], Ar 30 to Ar 35 may be any organic radical having the general formula [0047]
  • any one of the combinations of Ar 30 and Ar 3i , Ar 32 and Ar 33 , and Ar 34 and Ar 35 may wind in a ring to form a nitrogen-containing heterocyclic skeleton such as a carbazole skeleton.
  • Ar 36 and Ar 37 may be identical to or different from each other.
  • Ar 38 to Ar 2 may be identical to or different from each other.
  • any one of the combinations of Ar 38 and Ar 39 , and Ar 4 o and Ar 41 may wind in a ring to form a nitrogen- containing heterocyclic skeleton such as a. carbazole skeleton .
  • Ar 43 to Ar 45 may be
  • Ar 46 to Ar 5 i may be identical to or different from one another.
  • any one of the combinations of Ar 6 and Ar 47 , and Ar g and Ar 50 may wind in a ring to form a nitrogen- containing heterocyclic skeleton such as a carbazole skeleton.
  • Ar 52 to Ar 54 may be
  • Ar 55 to Ar 60 may be identical to or different from one another.
  • any one of the combinations of Ar 55 and Ar 56 , Ar 57 and Ar 58 , and Ar 59 and Ar 6 o may wind in a ring to form a nitrogen-containing heterocyclic skeleton such as a carbazole skeleton.
  • Ar 6 i to Ar 63 may be
  • Ar 6 5 to Ar 68 may be identical to or different from one another.
  • a compound according to the general formula [17] comprehends a polymer compound having a large number (m value) of repeating units.
  • the organic compound layer (such as a hole transport layer or an electron-blocking layer) between the anode and the emission layer.
  • the organic compound layer contains the compound A and the compound B.
  • the inventors of the present invention have produced an organic light-emitting device having a device
  • the relative ratio (%) of the SP 3 carbon atoms in the compound A can be determined from the following equation. It should be noted that the resultant value is rounded off to the nearest integer.
  • SP 3 carbon atoms generally have the following features (la-1) and (la-2) :
  • (la-1) a feature that an SP 3 carbon atom suppresses intermolecular stacking in a film to suppress the contraction of a band gap
  • la-2 a feature that there is no absorption (derived from a substituent (such as an alkyl group or an aliphatic condensed polycyclic group) constituted of an SP 3 carbon atom)) in a visible region.
  • a substituent such as an alkyl group or an aliphatic condensed polycyclic group constituted of an SP 3 carbon atom
  • SP 2 carbon atoms generally have the
  • the feature (lb-2) is a feature caused by the fact that a stacking interaction is strengthened by the presence of a large amount of electrons delocalized by n-electron systems on a rigid planar structure and SP 2 hybrid orbital.
  • the feature (lb-2) becomes more significant as the number of n-electrons increases.
  • the emission efficiency improves as an SP 3 carbon atom in an alkyl group or the like of an organic compound corresponding to the compound A is incorporated in a certain amount or more, in other words, the ratio of a substituent (such as an alkyl group) formed of an SP 3 carbon atom in a molecule increases.
  • the improving effect- on the emission efficiency appears when the relative ratio (%) of the SP 3 carbon atoms is 40% or more.
  • the relative ratio (%) of the number of the SP 3 carbon atoms in the compound A to the number of the SP 2 carbon atoms in the compound A is preferably 80% or more .
  • the structure and substituent of the compound A are not particularly limited as long as the compound has a relative ratio (%) of the SP 3 carbon atoms of 40% or more.
  • the compound is preferably of a
  • Ar x and Z x in the general formula [1], and Ar 2 and Ar 3 in the general formula [2] are each more preferably of a structure having a wide band gap.
  • the structure contains an aryl group such as a phenyl group, a fluorenyl group, a biphenyl group, or a naphthyl group. This is because the structure has suppressing effects on the movement of an exciton and the injection of an electron.
  • a higher ratio of the compound A may improve the emission efficiency and a higher ratio of the compound B may reduce the driving voltage of the device. Accordingly, when compatibility between high efficiency and low-voltage driving is to be achieved, the ratio (mixing ratio, weight base) of the compound B in the organic compound layer is
  • an assist material that may promote carrier injection may be incorporated into the organic compound layer in addition to the compound A and the compound B.
  • Exemplified Compounds AA-1 to AA-35 are each a compound having the following feature: the compound has a wide band gap and a high glass transition temperature.
  • Exemplified Compounds AB-1 to AB-11 are a group of compounds in each of which Ari represents, or Ar 2 and Ar 3 each represent, a biphenyl group. Each compound belonging to the compound group has a wide band gap and a low sublimation temperature because the compound has a rotation axis in a biphenyl skeleton .
  • Exemplified Compounds AC-1 to AC-17 are a group of compounds in each of which ri represents, or r 2 and Ar 3 each represent, a phenyl group.
  • ri represents, or r 2 and Ar 3 each represent, a phenyl group.
  • a compound having a wide band gap is easily designed because the band gap of a phenyl group is wide.
  • sublimation temperature of the compound can be reduced because its molecular weight can be reduced.
  • Exemplified Compounds AD-1 to AD-5 are a group of compounds in each of which Ari represents, or Ar 2 and Ar 3 each represent, a naphthyl group.
  • Ari represents, or Ar 2 and Ar 3 each represent, a naphthyl group.
  • Each compound belonging to the compound group has the following feature: the compound has a wide band gap and a high glass transition temperature.
  • Exemplified Compounds AE-1 to AE-3 are a group of compounds in each of which Ari represents, or Ar 2 and Ar 3 each represent, a phenanthryl group.
  • Each compound belonging to the compound group has the following feature: the compound has a wide band gap and a high glass transition temperature, though having a large molecular weight.
  • the compound A organic compound free of a nitrogen atom and a metal atom
  • the compound B compound having a tertiary amine structure
  • the constituent materials for the organic light-emitting device of the present invention are not limited to the compound A and the compound B. It should be noted that any other
  • the organic compound of the present invention is a compound represented by the following general formula [3] or [4] .
  • Z 2 represents a naphthyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, an aliphatic condensed polycyclic group, a carbon atom, or an oxygen atom. That is, Z 2 represents a monovalent group, i.e., a naphthyl group, a fluorenyl group, a phenanthryl group, or a
  • triphenylenyl group a 2- to 6-valent group derived from the monovalent group, an aliphatic condensed polycyclic group, a carbon atom, or an oxygen atom.
  • the substituent represented by Z 2 may further have an alkyl group, an alkoxy group, an aryl group, or a halogen atom. It is preferred that Z 2 represent an aliphatic condensed polycyclic group, carbon atom, or oxygen atom that may further have an alkyl group, an alkoxy group, an aryl group, or a halogen atom.
  • Examples of the aliphatic condensed polycyclic group represented by Z 2 include substituents derived from aliphatic condensed polycyclic compounds shown below. [0095]
  • the substituent represented by Z 2 may further have: an alkyl group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec- butyl group, an octyl group, a 1-adamantyl group, a 2- adamantyl group, a cyclohexyl group, a cyclopentyl group, or a cyclohexylmethyl group; an alkoxy group such as a methoxy group, an ethoxy group, an isopropoxy group, an n-propoxy group, a sec-butoxy group, a tert- butoxy group, or an octoxy group; an aryl group such as a phenyl group or a phenyl group having an alkyl group; or a halogen atom such as chlorine,
  • Ri to Rg each represent a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom, provided that at least two of the
  • substituents represented by Ri to R 9 are alkyl groups.
  • m represents an integer of 1 to 6, provided that when Z 2 represents a carbon atom, m represents 1 to 4, and when Z 2 represents an oxygen atom, m represents 1 or 2.
  • m represents 2 or more, structures in parentheses may be identical to or
  • m preferably represents 2 or more because crystallinity is reduced and film property is improved.
  • R to R 28 each represent a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom, provided that at least two of the
  • substituents represented by Rn to R 2 8 are alkyl groups.
  • the alkyl group represented by any one of Ri to R 9 and Rn to R 2 8 is preferably an alkyl group having 10 or less carbon atoms. Examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec- butyl group, an octyl group, an isoamyl group, a 1- adamantyl group, a 2-adamantyl group, a cyclohexyl group, a cyclopentyl group, and a cyclohexylmethyl group.
  • the introduction of any such substituent improves the heat stability of the compound itself. In addition, the introduction of any such substituent can prevent intermolecular association when the compound is formed into a film, and hence can suppress the
  • a branched alkyl group such as an isopropyl group, a tert-butyl group, an isoamyl group, an adamantyl group, a
  • substituents additionally improves the heat stability of the compound itself.
  • the alkoxy group represented by any one of Ri to Rg and Rii to R28 is preferably an alkoxy group having 10 or less carbon atoms. Examples thereof include a methoxy group, an ethoxy group, an isopropoxy group, an n- propoxy group, a sec-butoxy group, a tert-butoxy group, and an octoxy group. Of those, an alkoxy group in which a branched alkyl is introduced such as an
  • isopropoxy group, a sec-butoxy group, or a tert-butoxy group is more preferred.
  • halogen atom represented by any one of Ri to R 9 and R to R 2 e include chlorine, bromine, and fluorine. Of those, fluorine is preferred because it has a large preventing effect on the association of fluorene skeletons in the molecules.
  • the organic compound represented by the general formula [3] is preferably an organic compound represented by the following general formula [5] .
  • the organic compound represented by the general formula [4] is preferably an organic compound represented by the following general formula [ 6] .
  • Z n represents a naphthyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, an aliphatic condensed polycyclic group, a carbon atom, or an oxygen atom.
  • the substituent represented by Z may further have an alkyl group, an alkoxy group, an aryl group, or a halogen atom.
  • Zn represent an aliphatic condensed polycyclic group, carbon atom, or oxygen atom that may further have an alkyl group, an alkoxy group, an aryl group, or a halogen atom.
  • aliphatic condensed polycyclic group represented by Zn are the same as the specific examples of the aliphatic condensed polycyclic group represented by Z 2 in the general formula [3] .
  • substituent represented by Z may further have are the same as the specific examples of the alkyl group, alkoxy group, aryl group, or halogen atom which the substituent represented by Z 2 in the general formula
  • [3] may further have.
  • m represents an integer of 1 to 6, provided that when Zn represents a carbon atom, m represents 1 to 4, and when Z 1X represents an oxygen atom, m represents 1 or 2.
  • Zn represents a carbon atom
  • m represents 1 to 4
  • Z 1X represents an oxygen atom
  • m represents 1 or 2.
  • structures in parentheses may be identical to or
  • R 2 , R6, R 8 , and R 9 in the general formula [5], and R i2 , Ri 6 , Ri 8 , R 19 , R 2i , R 24 , R27, and R 28 in the general formula [6] each preferably represent an alkyl group or an alkoxy group.
  • the reason for the foregoing is that the substitution of any one of the 2-, 7-, and 9-positions of a fluorene skeleton with an alkyl group or an alkoxy group can surely prevent the association of fluorene skeletons between molecules.
  • the compound has a wide band gap and the first peak value (peak value at the longest wavelength) of its absorption spectrum in a dilute solution is less than 400 nm;
  • the compound has a high lowest excited triplet state (Ti) and the first peak value (peak value at the shortest wavelength) of its phosphorescence emission spectrum in a low-temperature dilute solution is less than 520 nm.
  • the organic compound represented by the general formula [3] is such a compound that a carbon atom at the 4-position of the fluorene skeleton is substituted with the
  • Z 2 represents a divalent or more aromatic hydrocarbon group, aliphatic condensed polycyclic group, carbon atom, or oxygen atom that may have a substituent (an alkyl group, an alkoxy group, an aryl group, or a halogen atom) .
  • the compound is selected from aromatic hydrocarbon compounds each having a first peak value of its absorption spectrum in a dilute solution in a dilute solution state of less than 400 nm and each having a wide band gap.
  • the organic compound of the present invention has a wide band gap and the first peak value of its
  • the organic compound represented by the general formula [3] is of a
  • the first peak value of its absorption spectrum in a dilute solution is maintained at less than 400 nm.
  • fluoranthene and benzofluoranthene have narrow band gaps, and hence the first peak value of the
  • absorption spectrum of each of the compounds in a dilute solution is 400 nm or more.
  • the first peak value of Compound C-1 is 405 nm.
  • each (divalent or more) aromatic hydrocarbon group represented by Z 2 is selected from skeletons each having a first peak value of its phosphorescence emission spectrum in a low-temperature dilute solution of less than 520 nm and each having a high ⁇ .
  • the organic compound of the present invention has a high Ti and the first peak value of its
  • each of Compounds C-l, C-2, and C-3 has a skeleton (a fluoranthene skeleton or a
  • the first peak value of the phosphorescence emission spectrum of each of the compounds in a low-temperature dilute solution is 520 nm or more.
  • the first peak values of fluoranthene and benzofluoranthene are 540 nm and 566 nm, respectively.
  • the i of Compound C-l having a fluoranthene skeleton is 557 nm.
  • the absorption first peak wavelength is defined from the peak wavelength of the toluene solution (lxlCT 6 mol/1) at the longest wavelength. It should be noted that a spectrophotometer U-3010 manufactured by Hitachi, Ltd. is used in the
  • the structure of the entire molecule of each of the organic compounds represented by the general formulae [3] and [4] is non-planar because the compound is bonded to an adjacent substituent at the 4- position of its fluorene skeleton.
  • the organic compound of the present invention is brought into a thin-film state, the film becomes an amorphous film that hardly crystallizes and is stable by virtue of the presence of the foregoing feature.
  • the presence of the feature can suppress the occurrence of an excimer because the presence suppresses the
  • the compound of the present invention is useful as a constituent material for an organic light-emitting device, specifically, a host to be incorporated into its emission layer.
  • the organic compound of the present invention can provide an organic light- emitting device having high device durability because an amorphous film that hardly crystallizes and is stable can be formed from the compound.
  • the compound has a wide band gap and a T x of less than 520 nm. Accordingly, when the compound is used as a host for a blue fluorescent light-emitting material or for a blue or green phosphorescent light- emitting material out of the hosts, light emission derived from a light-emitting dopant can be output.
  • the compound is also useful as a transport layer such as a hole transport layer or an electron transport layer, or a layer for blocking a charge such as an electron-blocking layer or a hole-blocking layer.
  • a transport layer such as a hole transport layer or an electron transport layer
  • a layer for blocking a charge such as an electron-blocking layer or a hole-blocking layer.
  • Exemplified Compounds AA-1 to AA-4 are a group of compounds each corresponding to the organic compound represented by the general formula [4] Each of those compounds has a high deposition speed at the time of its vacuum deposition because of the following reason: the compound has a small molecular weight, and hence has high sublimability and sublimates at a low temperature.
  • Exemplified Compounds AA-9 to AA-11 are a group of compounds each corresponding to the organic compound represented by the general formula [3] and are a group of compounds in each of which Z 2 represents a naphthyl group or a fluorenyl group.
  • Z 2 represents a naphthyl group or a fluorenyl group.
  • the Ti ' s of the compounds themselves are high because each of a naphthyl group and a fluorenyl group is a
  • an emission layer constituting an organic light-emitting device or as a constituent material for a charge transport layer or charge- blocking layer may improve its emission efficiency.
  • the compounds are particularly preferred in green phosphorescent light-emitting devices.
  • Exemplified Compounds AA-17 to AA-19 are a group of compounds each corresponding to the organic compound represented by the general formula [3] and are a group of compounds in each of which Z 2 represents a carbon atom or an aliphatic condensed polycyclic group.
  • Z 2 represents a carbon atom or an aliphatic condensed polycyclic group.
  • Each compound belonging to the compound group is of such a structure that conjugation with a fluorene skeleton does not occur. Accordingly, both of its band gap and Ti enlarge. Therefore, the compound is preferred in a blue phosphorescent device.
  • Exemplified Compounds AA-20 to AA-23 are a group of compounds each corresponding to the organic compound represented by the general formula [3] and are a group of compounds in each of which Z 2 represents an oxygen atom.
  • Each compound belonging to the compound group has a low ionization potential because the compound has an electron-donating effect based on an oxygen atom. Accordingly, the use of the compound as a host to be incorporated into an emission layer constituting an organic light-emitting device or as a constituent material for a hole transport layer or electron-blocking layer promotes the injection of a hole and reduces its driving voltage.
  • Exemplified Compounds AA-28 to AA-35 are a group of compounds each corresponding to the organic compound represented by the general formula [3] and are a group of compounds in each of which Z 2 represents an aromatic condensed polycyclic group obtained by condensing three or more rings.
  • Z 2 represents an aromatic condensed polycyclic group obtained by condensing three or more rings.
  • condensing three or more rings is a substituent having a Ti of 580 nm or less and high planarity, specifically, a phenanthryl group or a triphenylenyl group.
  • Each compound belonging to the compound group has a high T lf and hence its use as a host to be incorporated into an emission layer constituting an organic light-emitting device or as a constituent material for a hole
  • the compound is particularly preferably used as a constituent material for a green or red phosphorescent light-emitting device.
  • each compound belonging to the compound group has a substituent having high planarity, and hence carrier hopping between its molecules may be promoted and its carrier mobility may be high.
  • the organic compound of the present invention which is mainly used as a constituent material for an organic light-emitting device, can be used as a material not only for the organic light-emitting device but also for a living organism internal indicator or filter film.
  • (2A) an organic light-emitting device including at least an anode, a cathode, an emission layer formed between the anode and the cathode, and an organic compound layer formed between the anode and the
  • the organic compound layer containing a compound having a tertiary amine structure
  • (2B) an organic light-emitting device including an anode, a cathode, and an organic compound layer formed between the anode and the cathode.
  • the organic compound of the present invention is used as a constituent material for the organic light- emitting device according to the aspect (2A) , the organic compound of the present invention is
  • the organic compound layer constituting the organic light-emitting device according to the aspect (2A) is a layer formed between the anode and the emission layer. Accordingly, the organic compound of the present invention is
  • a layer formed between the anode and the emission layer such as a hole transport layer, a hole injection layer, or an electron-blocking layer.
  • (2B-1) an organic light-emitting device including an anode, a cathode, an emission layer formed between the anode and the cathode, and an organic compound layer (hole injection/transport layer) formed between the anode and the emission layer;
  • (2B-2) an organic light-emitting device including an anode, a cathode, an emission layer formed between the anode and the cathode, and an organic compound layer
  • an organic light-emitting device including an anode, a cathode, and an emission layer formed between the anode and the cathode (an organic light-emitting device including an emission layer as the "organic compound layer" in the aspect (2B) ) .
  • examples of the organic compound layer containing the organic compound of the present invention include an emission layer, a hole injection/transport layer (a hole
  • the layer containing the organic compound of the present invention may be a single layer or may be multiple layers. Further, when the organic compound of the present invention is used as a constituent material for the organic light-emitting device
  • the layer containing the organic compound of the present invention may be a layer formed only of the organic compound of the present invention, or may be a layer obtained by mixing the organic compound of the present invention and any other compound.
  • each of the constructions (a) to (e) is a
  • the present invention is not limited thereto and a construction in the case where the electrode close to the substrate is the cathode is of course included in the present invention.
  • a hole inj ectable/transportable material an emission assist material, an electron inj ectable/transportable material, or the like can be used.
  • Examples of the hole inj ectable/transportable material include a triarylamine derivative, a phenylenediamine derivative, a stilbene derivative, a phthalocyanine derivative, a porphyrin derivative, poly (vinyl
  • a fluorescent light-emitting material that emits blue, green, or red light
  • a triarylamine derivative e.g., a triarylamine derivative, a phenylene derivative, a condensed ring aromatic compound (e.g., a fluoranthene derivative, a
  • benzofluoranthene derivative a pyrene derivative, a chrysene derivative, or a derivative obtained by substitution thereof with a diarylamine) , or a stilbene derivative; and a phosphorescent light-emitting
  • an organic metal complex e.g., an organic iridium complex, an organic platinum complex, or a rare earth metal complex
  • the content of the guest is preferably 0.1 mass% or more and 30 mass% or less, more preferably 0.5 mass% or more and 10 mass% or less with reference to the total amount of the emission layer.
  • the host in the emission layer is a material having the highest weight ratio in the emission layer.
  • the host include, but of course not limited to, a triarylamine derivative, a phenylene derivative, a condensed ring aromatic compound (e.g., a naphthalene derivative, a phenanthrene derivative, a fluorene derivative, or a chrysene derivative) , an organic metal complex (e.g., an organic aluminum complex such as tris ( 8-quinolinolato) aluminum, an organic beryllium complex, an organic iridium complex, or an organic platinum complex)., and a polymer derivative such as a poly (phenylene vinylene) derivative, a poly ( fluorene ) derivative, a poly (phenylene ) derivative, a
  • Examples of the host include, but of course not limited to: condensed ring compounds (such as a fluorene derivative, a naphthalene derivative, an anthracene derivative, a pyrene derivative, a carbazole derivative, a quinoxaline derivative, and a quinoline derivative) ; an organic aluminum complex such as tris(8- quinolinolato) aluminum; an organic zinc complex; a triphenylamine derivative; and polymer derivatives such as a poly ( fluorene ) derivative and a poly (phenylene) derivative in addition to the group of compounds
  • the electron inj ectable/transportable material can be arbitrarily selected from materials that allow
  • oxazole derivative a pyrazine derivative, a triazole derivative, a triazine derivative, a quinoline
  • a constituent material for the anode desirably has as large a work function as possible.
  • Examples thereof may include: metal simple substances such as gold, platinum, silver, copper, nickel, palladium, cobalt, selenium, vanadium, and tungsten or alloys obtained by combining these metal simple substances; metal oxides, such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide; and conductive polymers such as polyaniline, polypyrrole, and
  • anode may be of a
  • a constituent material for the cathode desirably has as small a work function as possible.
  • metal simple substances such as alkali metals such as lithium;
  • alkaline earth metals such as calcium
  • aluminum, titanium, manganese, silver, lead, and chromium alkaline earth metals such as calcium
  • alloys obtained by combining those metal simple substances can be used.
  • a metal simple substance for example, a metal simple substance, a metal simple substance, or a metal simple substance, or a metal simple substance.
  • magnesium-silver alloy an aluminum-lithium alloy, or an aluminum-magnesium alloy can be used.
  • a metal oxide such as indium tin oxide (ITO) can also be utilized.
  • the cathode may be of a single-layer construction or may be of a multilayer construction .
  • the organic compound layer (such as the hole injection layer, the hole transport layer, the electron-blocking layer, the emission layer, the hole-blocking layer, the electron transport layer, or the electron injection layer) for forming the organic light-emitting device of the present invention is formed by the following method.
  • a dry process such as a vacuum deposition method, an
  • ionized vapor deposition method sputtering, or a plasma process
  • a wet process involving dissolving the constituent materials in an appropriate solvent and forming a layer by a known application method (such as spin coating, dipping, a casting method, an LB method, or an ink jet method) can be used instead of the dry process.
  • the layer when the layer is formed by the vacuum deposition method, the solution application method, or the like, the layer hardly undergoes crystallization or the like and is excellent in stability over time.
  • the film when the layer is formed by the application method, the film can be formed in combination with an appropriate binder resin.
  • binder resin examples include, but not limited to, a polyvinyl carbazole resin, a polycarbonate resin, a polyester resin, an ABS resin, an acrylic resin, a polyimide resin, a phenol resin, an epoxy resin, a silicone resin, and a urea resin.
  • binder resins may be any kind of those binder resins.
  • a known additive such as a plasticizer, an antioxidant, or a UV absorber may be used in combination as required.
  • the organic light-emitting device of the present invention is the organic light-emitting device of the present.
  • the organic light-emitting device finds use in
  • a light-emitting apparatus including a white light source and a color filter.
  • the color filter include filters that transmit light beams having three colors, i.e., red, green, and blue colors.
  • a display apparatus of the present invention includes the organic light-emitting device of the present
  • the invention in its display portion. It should be noted that the display portion includes multiple pixels.
  • the pixels each include the organic light- emitting device of the present invention and a
  • the transistor as an example of an active device (switching device) or amplifying device for controlling emission luminance, and the anode or cathode of the organic light-emitting device and the drain electrode or source electrode of the transistor are electrically connected to each other.
  • the display apparatus can be used as an image display apparatus for a PC or the like.
  • the transistor is, for example, a TFT device and the TFT device is provided on, for example, the insulating surface of a substrate.
  • the TFT device preferably includes an electrode formed of a
  • the display apparatus may be an image information
  • processing apparatus that includes an image input portion for inputting image information from, for example, an area CCD, a linear CCD, or a memory card, and displays an input image on its display portion.
  • the apparatus or inkjet printer may have a touch panel function.
  • the drive system of the touch panel function is not particularly limited.
  • the display apparatus may be used in the display portion of a multifunction printer.
  • a lighting apparatus is an apparatus for lighting, for example, the inside of a room.
  • the lighting apparatus may emit light having any one of the following colors: a white color (having a color temperature of 4,200 K) , a daylight color (having a color temperature of 5,000 K) , and colors ranging from blue to red colors.
  • a lighting apparatus of the present invention includes the organic light-emitting device of the present invention and an AC/DC converter circuit (circuit for converting an AC voltage into a DC voltage) connected to the organic light-emitting device and supplying a driving voltage to the organic light-emitting device. It should be noted that the lighting apparatus may further include a color filter.
  • An image-forming apparatus of the present invention is an image-forming apparatus including: a photosensitive member; a charging portion for charging the surface of the photosensitive member; an exposure portion for exposing the photosensitive member to form an electrostatic latent image; and a developing unit for developing the electrostatic latent image formed on the surface of the photosensitive member.
  • the exposing unit to be provided in the image-forming apparatus includes the organic light-emitting device of the present invention.
  • the organic light-emitting device of the present invention can be used as a constituent member (light-emitting member) for an exposing machine for exposing a photosensitive member.
  • An exposing machine including the organic light-emitting device of the present invention is, for example, an exposing machine in which a plurality of the organic light-emitting devices of the present invention are placed to form a line along a predetermined linear direction.
  • FIG. 1 is a schematic sectional view illustrating an example of a display apparatus including an organic light-emitting device and a switching device connected to the organic light-emitting device. It should be noted that the organic light-emitting device of the present invention is used as the organic light-emitting device
  • the display apparatus 1 of FIG. 1 includes a substrate
  • a metal gate electrode 13 is represented by reference numeral 13, a gate
  • insulating film 14 is represented by reference numeral 14
  • a semiconductor layer is represented by
  • the TFT device 18 includes the semiconductor layer 15, a drain electrode 16, and a source electrode 17.
  • An insulating film 19 is formed on the TFT device 18.
  • An anode 21 constituting the organic light-emitting device and the source electrode 17 are connected to each other through a contact hole 20.
  • a system for the electrical connection between the electrode (anode or cathode) in the organic light-emitting device and the electrode (source electrode or drain electrode) in the TFT is not limited to the aspect illustrated in FIG. 1. In other words, one of the anode and the cathode, and one of the source electrode and drain electrode of the TFT device have only to be electrically connected to each other.
  • an organic compound layer 22 may be multiple layers.
  • protective layer 25 for suppressing the deterioration of the organic light-emitting device are formed on a cathode 23.
  • an emission layer in the organic compound layer 22 in FIG. 1 may be a layer obtained by mixing a red light-emitting material, a green light-emitting material, and a blue light- emitting material.
  • the layer may be a laminated emission layer obtained by laminating a layer formed of the red light-emitting material, a layer formed of the green light-emitting material, and a layer formed of the blue light-emitting material.
  • the layer formed of the red light-emitting material, the layer formed of the green light-emitting material, and the layer formed of the blue light- emitting material are, for example, arranged side by side to form domains in one emission layer.
  • the transistor is used as the switching device in the display apparatus 1 of FIG. 1, an MIM device may be used instead of the transistor as the switching device.
  • the transistor to be used in the display apparatus 1 of FIG. 1 is not limited to a transistor using a monocrystalline silicon wafer and may be a thin-film transistor including an active layer on the insulating surface of a substrate.
  • a thin-film transistor including an active layer on the insulating surface of a substrate may be used in the display apparatus 1 of FIG. 1 .
  • the thin-film transistor using monocrystalline silicon as the active layer, a thin-film transistor using non-monocrystalline silicon such as amorphous silicon or macrocrystalline silicon as the active layer, or a thin-film transistor using a non-monocrystalline oxide semiconductor such as an indium zinc oxide or an indium gallium zinc oxide as the active layer is also permitted. It should be noted that the thin-film transistor is also called a TFT device .
  • the transistor in the display apparatus 1 of FIG. 1 may be formed in a substrate such as an Si substrate.
  • a substrate such as an Si substrate.
  • the phrase "formed in a substrate” means that the transistor is produced by processing the substrate itself such as an Si substrate.
  • the presence of the transistor in the substrate can be regarded as follows: the substrate and the transistor are integrally formed.
  • the transistor is provided in the substrate is selected depending on definition .
  • the organic light-emitting device is preferably provided in the Si substrate.
  • apparatus using the organic light-emitting device of the present invention enables display that has good image quality and is stable over a long time period.
  • Exemplified Compound AA-1 was synthesized according to the following synthesis scheme.
  • Exemplified Compound AA-6 was synthesized according to the following synthesis scheme.
  • Mass spectrometry confirmed 759 as the M + of Exemplified Compound AA-6.
  • Exemplified Compound AA-8 was synthesized according to the following synthesis scheme.
  • Exemplified Compound AA-9 was synthesized according to the following synthesis scheme.
  • Mass spectrometry confirmed 737 as the M + of
  • Exemplified Compound AA-7 was synthesized according to the following synthesis scheme.
  • Exemplified Compound AA-20 was synthesized according to the following synthesis scheme. It should be noted that tBu represents a tert-butyl group.
  • Mass spectrometry confirmed 627 as the M + of
  • Mass spectrometry confirmed 763 as the M + of
  • Comparative Compound AZ-1 was synthesized by the same method as that of Example 4 except that Compound b-32 was used instead of 1 , 4-dibromonaphthalene and Compound b-31 was used instead of Compound b-3 in Example 4.
  • Exemplified Compound AB-3 was synthesized according to the following synthesis scheme.
  • Mass spectrometry confirmed 607 as the M + of
  • Exemplified Compound AC-6 was synthesized according to the following synthesis scheme.
  • Mass spectrometry confirmed 617 as the M + of
  • Mass spectrometry confirmed 683 as the M + of
  • Exemplified Compound AB-6 was synthesized according to the following synthesis scheme.
  • Mass spectrometry confirmed 707 as the M + of
  • an organic light-emitting device in which an anode, a hole transport layer, an emission layer, a hole-blocking layer, an electron transport layer, and a cathode were formed in the stated order on a substrate was produced by a method described below.
  • part of the compounds used in this example are listed below.
  • ITO Indium tin oxide
  • the anode was formed.
  • the thickness of the anode was set to 120 nm.
  • the substrate with the anode formed thereon was sequentially subjected to ultrasonic washing with acetone and ultrasonic washing with isopropyl alcohol (IPA), and was then subjected to boil washing with IPA, followed by drying. Further, the dried product was subjected to UV/ozone washing, and the resultant was used as a transparent conductive supporting substrate in the following steps.
  • IPA isopropyl alcohol
  • Compound A Exemplified Compound AC-6 (hereinafter referred to as “compound A”) and chloroform were mixed to prepare a material solution A having a concentration of 0.25 wt%.
  • BC-4 hereinafter referred to as “compound B”
  • chloroform were mixed to prepare a material solution B having a concentration of 0.25 wt%.
  • a mixed liquid was prepared by mixing the material solution A and the material solution B so that their weight ratio became 2:1.
  • the mixed liquid was dropped onto the anode (ITO electrode) and then a thin film was formed by spin coating at 500 RPM for 10 seconds and then at 1,000 RPM for 1 minute. After that, the solvent in the thin film was completely removed by drying the thin film in a vacuum oven at 80 °C for 10 minutes. Thus, the hole transport layer was formed. At this time, the
  • thickness of the hole transport layer was 30 nm.
  • the device had an emission efficiency (cd/A) of 13.0 cd/A and an external quantum yield of 7.5%.
  • the device had CIE chromaticity coordinates of (0.16, 0.26) and was observed to emit blue light satisfactorily.
  • Example 12 to 17 Organic light-emitting devices were each produced by the same method as that of Example 11 except that the compound A and the compound B were changed to compounds shown in Table 7 below in Example 11. In addition, the resultant organic light-emitting devices were evaluated by the same method as that of Example 11. Table 7 shows the results.
  • Organic light-emitting devices were each produced by the same method as that of Example 11 except that
  • Exemplified Compound AA-1 was used as the compound A and the compound B was changed to a compound shown in Table 7 below in Example 11.
  • the compound B was changed to a compound shown in Table 7 below in Example 11.
  • Organic light-emitting devices were each produced by the same method as that of Example 11 except that the compound A and the compound B were changed to compounds shown in Table 8 below in Example 11. In addition, the resultant organic light-emitting devices were evaluated by the same method as that of Example 11. Table 8 shows the results.
  • Organic light-emitting devices were each produced by the same method as that of Comparative Example 4 except that the compound B was changed to a compound shown in Table 8 below in Comparative Example 4.
  • the resultant organic light-emitting devices were evaluated by the same method as that of Example 11. Table 8 shows the results.
  • an organic light-emitting device was produced.
  • An organic light-emitting device in which an anode, a hole transport layer, an emission layer, a hole-blocking layer, an electron transport layer, and a cathode were formed in the stated order on a substrate was produced by a method described below. Here, part of the compounds used in this example are listed below. [0283]
  • a chloroform solution having a concentration of 0.25 wt% was prepared by mixing Exemplified Compound AA-1 and chloroform.
  • the chloroform solution was dropped onto the anode (ITO electrode) and then a thin film was formed by spin coating at 500 RPM for 10 seconds and then at 1,000 RPM for 1 minute. After that, the solvent in the thin film was completely removed by drying the thin film in a vacuum oven at 80 °C for 10 minutes. Thus, the hole transport layer was formed. At this time, the thickness of the hole transport layer was 30 nm.
  • the device had an emission efficiency (cd/A) of 7.2 cd/A and was observed to emit . blue light satisfactorily.
  • An organic light-emitting device was produced by the same method as that of Example 21 except that
  • Example 21 Exemplified Compound AA-1 in Example 21.
  • the emission characteristics of the organic light-emitting device were measured and evaluated by the same method as that of Example 21. As a result, the device had an emission efficiency (cd/A) of 8.0 cd/A and was observed to emit blue light satisfactorily.
  • An organic light-emitting device was produced by the same method as that of Example 21 except that
  • Example 21 Exemplified Compound AA-1 in Example 21.
  • the emission characteristics of the organic light-emitting device were measured and evaluated by the same method as that of Example 21. As a result, the device had an emission efficiency (cd/A) of 7.1 cd/A and was observed to emit blue light satisfactorily.
  • ITO Indium tin oxide
  • the substrate with the anode formed thereon was sequentially subjected to ultrasonic washing with acetone and ultrasonic washing with isopropyl alcohol (IPA), and was then subjected to boil washing with IPA, followed by drying. Further, the dried product was subjected to UV/ozone washing, and the resultant was used as a transparent conductive supporting substrate in the following steps.
  • IPA isopropyl alcohol
  • Table 10 were continuously formed by a vacuum deposition method involving using resistance heating in a vacuum chamber at 1 ⁇ 10 ⁇ 5 Pa to produce an organic light-emitting device.
  • the electrode was defined as a negative electrode. As a result, the device was observed to emit blue light having CIE chromaticity coordinates of (0.21, 0.48).
  • An organic light-emitting device was produced by the same method as that of Example 24 except that

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EP4075533B1 (en) 2024-07-03
JP6444046B2 (ja) 2018-12-26
EP4075533A1 (en) 2022-10-19
EP2981993B1 (en) 2022-05-11
EP2981993A1 (en) 2016-02-10
US20150372238A1 (en) 2015-12-24
US9911921B2 (en) 2018-03-06
EP2981993A4 (en) 2017-04-12

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