WO2013118812A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

Info

Publication number
WO2013118812A1
WO2013118812A1 PCT/JP2013/052842 JP2013052842W WO2013118812A1 WO 2013118812 A1 WO2013118812 A1 WO 2013118812A1 JP 2013052842 W JP2013052842 W JP 2013052842W WO 2013118812 A1 WO2013118812 A1 WO 2013118812A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
substituted
unsubstituted
ring
Prior art date
Application number
PCT/JP2013/052842
Other languages
English (en)
Japanese (ja)
Inventor
加藤　朋希
貴康 佐土
藤山　高広
Original Assignee
出光興産株式会社
三井化学株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 出光興産株式会社, 三井化学株式会社 filed Critical 出光興産株式会社
Publication of WO2013118812A1 publication Critical patent/WO2013118812A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/156—Hole transporting layers comprising a multilayered structure
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers

Definitions

  • the present invention relates to an organic electroluminescence element, and more particularly to an organic electroluminescence element in which a hole transport layer can be thickened, an optical film thickness can be adjusted, and the element performance is improved.
  • An organic electroluminescence (EL) element is a self-luminous element that utilizes the principle that a fluorescent substance emits light by recombination energy of holes injected from an anode and electrons injected from a cathode by applying an electric field.
  • EL organic electroluminescence
  • Patent Documents 1 to 4 disclose a diamine compound having a fluorene skeleton between two nitrogen atoms, and using the diamine compound as a material for a hole transport layer “adjacent to a light emitting layer”.
  • the crystallization of the hole transport material due to heat generation during light emission in the light emitting layer is suppressed, and the stability and durability are improved compared to a diamine compound having a biphenylene group between two nitrogen atoms or a monoamine compound having a fluorene skeleton.
  • An improved organic EL device is disclosed.
  • Patent Document 5 a diamine compound in which two nitrogen atoms are bonded via a biphenylene group is used as a material for the first hole transport layer, and an aromatic amine derivative having a dibenzofuran structure and a carbazole structure is adjacent to the light emitting layer. It is disclosed that an organic EL device having a low driving voltage and a long lifetime can be produced by using as a material for the second hole transport layer.
  • Patent Document 6 employs a diamine compound in which two nitrogen atoms are bonded to a first hole transport layer via a biphenylene group, and phosphorescent property of an amine compound having a specific heteroaryl structure in the second hole transport layer.
  • Patent Document 7 provides an organic EL device having high light emission efficiency and low driving voltage by employing a compound having a carbazole ring structure in a hole transport layer “adjacent to the light emitting layer”. That is, in an organic EL device, particularly a phosphorescent device, the hole transport layer has a two-layer configuration of a first hole transport layer and a second hole transport layer, and the second hole transport layer "adjacent to the light emitting layer" The device performance has been improved by applying more sophisticated materials.
  • the performance required for the second hole transport layer includes (i) high triplet energy (preferably 2.6 eV or more) in order to prevent diffusion of excitation energy of the phosphorescent light emitting layer, and (ii) light emitting layer. And (iii) an organic layer having a low affinity (preferably 2.4 eV or less) to prevent electrons from leaking from the light emitting layer, and (iv) positive to the light emitting layer.
  • the organic layer is required to have a large ionization potential (preferably 5.5 eV or more).
  • a molecular skeleton having high electron resistance in which a heteroaryl ring such as carbazole or dibenzofuran is bonded to a triphenylamine skeleton is preferred.
  • the first hole transport layer is generally required to have excellent hole injectability into the second hole transport layer.
  • it has been studied to contain a compound having a p-type semiconductor property (also referred to as an acceptor material in the present invention) as the hole injection layer (Patent Documents 8 to 9). reference).
  • Patent Documents 8 to 9 As the research and development of the organic EL element as described above proceeds, it is indispensable for commercial devices to efficiently extract the light emitted internally for each emission color of the organic EL element. Therefore, it is necessary to adjust the optical path length of the entire device by controlling the film thickness of the hole transport layer having higher carrier transportability than other organic layers.
  • the present invention has been made to solve the above-described problems, and an object thereof is to provide an organic EL element with high efficiency and long life.
  • the present inventors have at least two hole transport layers between the anode and the cathode of the organic EL element and are not adjacent to the light emitting layer.
  • the hole transport layer contains a compound represented by the following formula (1), the interaction with the acceptor material is good, and the driving voltage does not increase even when the hole transport layer is thickened.
  • the present invention is an organic EL device having at least two or more hole transport layers and a light emitting layer sequentially between an anode and a cathode facing each other, and one of the hole transport layers is represented by the following formula ( The present invention provides an organic EL device containing the compound represented by 1) and not adjacent to a light emitting layer.
  • R 1 and R 2 each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
  • L 1 and L 2 each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.
  • Ar 1 to Ar 4 each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • the organic EL device of the present invention can increase the thickness of the hole transport layer, enable adjustment of the optical film thickness of the organic EL device, and improve the light emission efficiency and life of the device.
  • the organic EL device of the present invention is an organic EL device having at least two or more hole transport layers and a light emitting layer sequentially between an anode and a cathode facing each other, and one of the hole transport layers is the following: It contains the compound represented by formula (1) and is not adjacent to the light emitting layer.
  • R 1 and R 2 each independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
  • L 1 and L 2 each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.
  • Ar 1 to Ar 4 each independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • the compound represented by the formula (1) is preferably a compound represented by the following formulas (2) and (3).
  • R 1 , R 2 , L 2 , and Ar 1 to Ar 4 have the same meanings as those in formula (1).
  • Examples of the alkyl group having 1 to 10 carbon atoms represented by R 1 and R 2 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t- Examples thereof include butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, neopentyl group, and the like.
  • Methyl group, ethyl group, n-propyl group An isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, and a t-butyl group are preferable.
  • Examples of the aryl group having 6 to 30 ring carbon atoms represented by Ar 1 to Ar 4 include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a naphthacenyl group, a chrysenyl group, a pyrenyl group, a biphenyl group, a terphenyl group, A tolyl group, a fluoranthenyl group, a fluorenyl group and the like can be mentioned, and a phenyl group, a naphthyl group, a biphenyl group and a terphenyl group are preferable.
  • Examples of the arylene group having 6 to 30 ring carbon atoms represented by L 1 and L 2 include those having an aryl group represented by Ar 1 to Ar 4 as a divalent group, and a phenylene group is preferable.
  • the optional substituent in the case of “substituted or unsubstituted” described above and below will be a halogen atom (fluorine, chlorine, bromine, iodine), a cyano group, or an alkyl group having 1 to 20 carbon atoms (preferably 1 to 6).
  • carbon number ab in the expression “substituted or unsubstituted X group having carbon number ab” represents the number of carbons when X group is unsubstituted.
  • the carbon number of the substituent when the X group is substituted is not included.
  • part or all of the hydrogen atoms may be deuterium atoms.
  • the organic EL device of the present invention is an organic EL device having at least two or more hole transport layers and a light emitting layer sequentially between an anode and a cathode facing each other, and one of the hole transport layers is the above-described one. It contains the compound represented by formula (1) and is not adjacent to the light emitting layer.
  • the at least two or more hole transport layers include a first hole transport layer on the anode side and a second hole transport layer on the light emitting layer side, and the first hole transport layer is represented by the formula (1). It is more preferable to contain the represented compound.
  • the hole transport layer is a plurality of layers, and the hole transport layer not adjacent to the light emitting layer is a compound having a high mobility represented by the formula (1) as a hole transport material.
  • the compound represented by the formula (1) has good compatibility with an acceptor material having excellent hole injecting property, and can increase the amount of carriers generated to transport and inject more holes to the light emitting layer. This is thought to lead to higher device efficiency.
  • the organic EL device of the present invention is excellent as a phosphorescent organic EL device.
  • a heteroaryl-substituted amine derivative is used in the hole transport layer adjacent to the light emitting layer, a phosphorescent organic EL device is obtained.
  • excellent effects can be obtained as a fluorescent organic EL element.
  • the organic EL element of the present invention may be a fluorescent or phosphorescent monochromatic light emitting element, a fluorescent / phosphorescent hybrid white light emitting element, or a simple type having a single light emitting unit.
  • a tandem type having a plurality of light emitting units may be used.
  • the “light emitting unit” refers to a minimum unit that includes one or more organic layers, one of which is a light emitting layer, and can emit light by recombination of injected holes and electrons.
  • the element structure of the organic EL element of the present invention will be described.
  • (1) Structure of organic EL element As a typical element structure of the organic EL element of the present invention, (1) Anode / acceptor material-containing layer (acceptor layer) / first hole transport layer / second hole transport layer / light emitting layer / cathode (2) Anode / acceptor material-containing layer (acceptor layer) / first hole transport layer / second hole transport layer / light emitting layer / electron injection layer / cathode (3) Anode / acceptor material-containing layer (acceptor layer) / first hole transport layer / second hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode (4) Anode / first hole transport layer / second hole transport layer / light emitting layer / electron injection layer / cathode (5) Structures such as anode / first hole transport layer / second hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode can be mentioned.
  • Hole transport layers there may be further third, fourth,... Hole transport layers. There may be an electron barrier layer or an exciton barrier layer between the light emitting layer and the hole transport layer, and the hole transport layer in contact with the light emitting layer may be an electron barrier layer or an exciton barrier layer. .
  • the organic EL device of the present invention preferably has an acceptor layer containing an acceptor material between the anode and the at least two or more hole transport layers (particularly the hole transport layer closest to the anode).
  • the hole transport layer containing the compound represented by the formula (1) may contain an acceptor material.
  • the acceptor material since the bonding property with the hole transport layer containing the compound represented by the formula (1) is improved and the device performance can be expected to be further improved, the following formulas (A) and (B) Or what has skeleton with high planarity, such as a compound represented by (C), is preferable.
  • R 11 to R 16 are each independently a cyano group, —CONH 2 , carboxyl group, or —COOR 17 (R 17 is an alkyl group having 1 to 20 carbon atoms).
  • R 11 and R 12 , R 13 and R 14 , or R 15 and R 16 are bonded to each other to represent a group represented by —CO—O—CO—.
  • Examples of the alkyl group for R 17 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, and a cyclohexyl group.
  • Ar 10 is a condensed ring having 6 to 24 ring carbon atoms or a heterocyclic ring having 6 to 24 ring atoms.
  • ar 1 and ar 2 may be the same or different from each other and are represented by the following formula (i) or (ii). ⁇ Wherein X 1 and X 2 may be the same or different from each other, and are any of the divalent groups shown in the following (a) to (g).
  • R 31 to R 34 may be the same as or different from each other, and may be a hydrogen atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon atom having 1 to 20 carbon atoms).
  • An alkyl group, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 50 ring atoms, and R 32 and R 33 are bonded to each other to form a ring; May be) ⁇ R 21 to R 24 in formula (B) may be the same or different from each other, and are a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number 6 to 50, and Aryl groups, substituted or unsubstituted heterocyclic groups having 3 to 50 ring atoms, halogen atoms, substituted or unsubstituted fluoroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted 1 to 20 carbon atoms An alkoxy group, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon
  • R 21 to R 24 that are adjacent to each other may be bonded to each other to form a ring.
  • Y 1 to Y 4 may be the same or different from each other, and are —N ⁇ , —CH ⁇ , or C (R 25 ) ⁇ , and R 25 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • Examples of each group of R 21 to R 24 and R 31 to R 34 are as follows.
  • Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, and a cyclohexyl group.
  • the aryl group include a phenyl group, a biphenyl group, a naphthyl group, a fluorophenyl group, and a trifluoromethylphenyl group.
  • heterocyclic group examples include residues such as pyridine, pyrazine, furan, imidazole, benzimidazole, and thiophene.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • fluoroalkyl group examples include a trifluoromethyl group, a pentafluoroethyl group, a perfluorocyclohexyl group, and a perfluoroadamantyl group.
  • alkoxy group and the fluoroalkoxy group examples include a methoxy group, an ethoxy group, and a trifluoromethoxy group.
  • the aryloxy group examples include a phenyloxy group. These may have a substituent, and the substituted aryl group includes an aryl group substituted with a halogen atom such as a monofluorophenyl group and a trifluoromethylphenyl group; a tolyl group, a 4-t-butylphenyl group And an aryl group substituted with an alkyl group having 1 to 10 carbon atoms (preferably 1 to 5 carbon atoms).
  • a halogen atom such as a monofluorophenyl group and a trifluoromethylphenyl group
  • a tolyl group a 4-t-butylphenyl group
  • substituted alkyl group examples include alkyl groups substituted with a halogen atom, such as a trifluoromethyl group, a pentafluoroethyl group, a perfluorocyclohexyl group, and a perfluoroadamantyl group.
  • a halogen atom such as a trifluoromethyl group, a pentafluoroethyl group, a perfluorocyclohexyl group, and a perfluoroadamantyl group.
  • the substituted aryloxy group includes an aryloxy group substituted with a halogen atom or substituted with a halogen atom-containing alkyl group (having 1 to 5 carbon atoms), such as 4-trifluoromethylphenyloxy group and pentafluorophenyloxy; And an aryloxy group substituted with an alkyl group having 1 to 10 carbon atoms (preferably 1 to 5 carbon atoms) such as a 4-t-butylphenoxy group.
  • R 21 to R 24 that are adjacent to each other may be bonded to each other to form a ring. Examples of the ring include a benzene ring, a naphthalene ring, a pyrazine ring, a pyridine ring, and a furan ring.
  • Z 1 to Z 3 are each independently a divalent group represented by (h) below.
  • Ar 31 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 50 ring atoms.
  • the aryl group include a phenyl group and a naphthyl group.
  • the heteroaryl group include pyridine, pyrazine, pyrimidine, quinoline, isoquinoline and the like. Examples of these substituents include electron withdrawing groups such as a cyano group, a fluoro group, a trifluoromethyl group, a chloro group, and a bromo group.
  • the organic EL element of this invention is produced on a translucent board
  • the translucent substrate referred to here is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 to 700 nm of 50% or more.
  • a glass plate, a polymer plate, etc. are mentioned.
  • the glass plate include soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
  • the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.
  • Anode of the organic EL device of the present invention has a function of injecting holes into the hole transport layer or the light emitting layer, and it is effective to have a work function of 4.5 eV or more.
  • Specific examples of the anode material used in the present invention include indium tin oxide alloy (ITO), tin oxide (NESA), indium-zinc oxide (IZO), gold, silver, platinum, copper and the like.
  • the anode can be produced by forming a thin film from these electrode materials by a method such as vapor deposition or sputtering. Thus, when light emission from the light emitting layer is taken out from the anode, it is preferable that the transmittance of the anode for light emission is greater than 10%.
  • the sheet resistance of the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness of the anode depends on the material, it is usually selected in the range of 10 nm to 1 ⁇ m, preferably 10 to 200 nm.
  • Hole transport layer As described above, in the organic EL device of the present invention, at least two hole transport layers are used.
  • the hole transport layer not adjacent to the light emitting layer is often used in a thick film for optical adjustment of the organic EL element, and is required to have a high hole mobility from the viewpoint of lowering the voltage. Furthermore, in order to generate
  • the compound represented by the general formula (1) is preferably used as a material for a hole transport layer that is not adjacent to the light emitting layer in order to satisfy the characteristics required for the hole transport layer that is not adjacent to the light emitting layer.
  • characteristics required for the hole transport layer adjacent to the light emitting layer include high triplet energy (preferably 2.6 eV or more) to prevent excitation energy diffusion of the light emitting layer, and electron resistance because it is adjacent to the light emitting layer.
  • the organic layer In order to prevent electrons from leaking from the light emitting layer, the organic layer has a small affinity (preferably 2.4 eV or less), and in order to promote hole injection into the light emitting layer, the ionization potential is large (5.5 eV or more). It is required to be a (preferred) organic layer.
  • a heteroaryl-substituted amine derivative is preferable from the viewpoint of obtaining not only an excellent phosphorescent organic EL device but also an excellent fluorescent organic EL device, and more preferably the following formula (4): And compounds represented by (8) to (8).
  • At least one of Ar 11 to Ar 13 is a group represented by the following formula (4-2) or (4-3). Further, the group that is not a group represented by the formula (4-2) is a group represented by the following formula (4-3) or (4-4) or a substituted or unsubstituted aryl group having 6 to 40 carbon atoms. And the group that is not a group represented by the formula (4-3) is a group represented by the following formula (4-2) or (4-4) or a substituted or unsubstituted aryl having 6 to 40 carbon atoms It is a group. Particularly, at least one of Ar 11 to Ar 13 is preferably a compound represented by the following formula (4-2).
  • L 3 to L 5 each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and the substituents that L 3 to L 5 may have are A linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ring carbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms, a triarylsilyl group having 18 to 30 ring carbon atoms, An alkylarylsilyl group having 8 to 15 carbon atoms (the alkyl group has 1 to 5 carbon atoms, and the aryl group has 6 to 14 ring carbon atoms), an aryl group having 6 to 50 ring carbon atoms, A halogen atom or a cyano group; Ar 14 represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, A halogen atom or a cyano group; Ar 14
  • R 51 to R 56 are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, substituted Or an unsubstituted trialkylsilyl group having 3 to 10 carbon atoms, a substituted or unsubstituted triarylsilyl group having 18 to 30 ring carbon atoms, a substituted or unsubstituted alkylarylsilyl group having 8 to 15 carbon atoms (alkyl The group has 1 to 5 carbon atoms and the aryl group has 6 to 14 ring carbon atoms.) Represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a halogen atom, or a cyano group.
  • a plurality of adjacent R 51 to R 56 may be bonded to each other to form a ring.
  • b and f each independently represents an integer of 0 to 3
  • a, c, d and e each independently represents an integer of 0 to 4.
  • Examples of the arylene group represented by L 3 to L 5 include a phenylene group, a naphthylene group, a biphenylene group, an anthrylene group, an acenaphthylenyl group, an anthranylene group, a phenanthrylene group, a phenalenyl group, a quinolylene group, an isoquinolylene group, an s-indacenylene group, As-indacenylene group, chrysenylene group and the like can be mentioned.
  • an arylene group having 6 to 30 ring carbon atoms is preferable, an arylene group having 6 to 20 ring carbon atoms is more preferable, an arylene group having 6 to 12 ring carbon atoms is further preferable, and a phenylene group is particularly preferable.
  • the remaining groups will be described, but the same groups will be described in the same manner.
  • the alkyl group an alkyl group having 1 to 5 carbon atoms is preferable, and an alkyl group having 1 to 3 carbon atoms is more preferable.
  • alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, and an n-hexyl group.
  • the alkyl group of the trialkylsilyl group is as described above, and preferred ones are also the same.
  • Examples of the aryl group of the triarylsilyl group examples include a phenyl group, a naphthyl group, and a biphenylyl group.
  • alkylaryl group of the alkylarylsilyl group examples include a dialkylmonoarylsilyl group.
  • the alkyl group has 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms.
  • the aryl group has 6 to 14 ring-forming carbon atoms, preferably 6 to 10 carbon atoms.
  • Examples of the aryl group having 6 to 50 ring carbon atoms include phenyl group, naphthyl group, biphenylyl group, anthryl group, phenanthryl group, and terphenylyl group. Among these, an aryl group having 6 to 30 ring carbon atoms is preferable, an aryl group having 6 to 20 ring carbon atoms is more preferable, and an aryl group having 6 to 12 ring carbon atoms is more preferable.
  • Examples of the halogen atom include a fluorine atom, a chlorine atom, and an iodine atom.
  • Each of a to f is preferably 0 or 1, more preferably 0.
  • Preferred examples of the formula (4-2) include the following formulas (4-2 ′) and (4-2 ′′) (the definitions of each group are as described above).
  • Preferred examples of the formula (4-4) include the following formula (4-4 ′) (the definitions of each group are as described above).
  • Ar 11 to Ar 13 is preferably a group represented by formula (4-2).
  • X 11 in formula (4-2) is preferably an oxygen atom.
  • Ar 11 to Ar 13 two are preferably groups represented by the formula (4-2), one is a group represented by the formula (4-2), and one is the formula (4).
  • the group represented by -3) is preferred, and the group represented by the formula (4-2) is also preferred.
  • L 3 in the formula (4-2) and L 5 in the formula (4-4) are an arylene group
  • an increase in the electron density of the compound represented by the formula (4) is suppressed, and Ip is large. Therefore, since the hole injection into the light emitting layer is promoted, the driving voltage of the element tends to be low, which is preferable.
  • the amine is hardly oxidized, the compound is often stabilized, and the lifetime of the device is likely to be increased.
  • L 5 in the formula (4-4) is an arylene group, the compound is stable, and thus synthesis is easy.
  • arylene group a phenylene group is particularly preferable.
  • Ar 11 to Ar 13 in the formula (4) is not a group represented by any of the formulas (4-2) to (4-4), it is a substituted or unsubstituted aryl having 6 to 40 carbon atoms. Represents a group.
  • the aryl group is preferably represented by the following formulas (4-5) to (4-7).
  • R 61 to R 64 each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ring carbon atoms, or a tricyclic group having 3 to 10 carbon atoms.
  • a plurality of adjacent R 61 to R 64 may combine to form a saturated or unsaturated ring.
  • k, l, m, and n are each independently an integer of 0 to 4.
  • formulas (4-5) to (4-7) the following formulas (4-5 ′) to (4-7 ′) are preferable (the definition of each group is as described above).
  • the above formula (4-5 ′) includes the following groups.
  • Ar 15 to Ar 21 each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring group having 5 to 50 ring carbon atoms.
  • Ar 16 and Ar 17 , Ar 18 and Ar 19 , Ar 20 and Ar 21 may be bonded to each other to form a ring.
  • L 6 represents a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and the substituent that L 6 may have is a linear or branched group having 1 to 10 carbon atoms
  • the aryl moiety has 6 to 14 ring-forming carbon atoms, an aryl group having 6 to 50 ring-forming carbon atoms, a halogen atom, or a cyano group.
  • R 67 to R 77 are each independently a halogen atom, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted carbon number.
  • R 78 and R 79 are each independently a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted carbon atom having 6 to 40 carbon atoms. And a substituted or unsubstituted condensed aryl group having 6 to 12 carbon atoms and a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms.
  • g, i, p, q, r, s, w, and x are each independently an integer of 0 to 4.
  • h, y, and z are each independently an integer of 0 to 3. ]
  • a 1 and A 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.
  • Y 11 to Y 26 each independently represent C (R) or a nitrogen atom, and each R independently represents a bond bonded to a hydrogen atom, a substituent or a carbazole skeleton.
  • L 11 and L 12 each independently represent a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and the arylene group may have a substituent having 1 to 10 carbon atoms
  • the organic EL device of the present invention may have a light emitting layer containing a fluorescent light emitting material, that is, a fluorescent light emitting layer.
  • a fluorescent light emitting layer known fluorescent light emitting materials can be used.
  • the fluorescent material is preferably at least one selected from anthracene derivatives, fluoranthene derivatives, styrylamine derivatives and arylamine derivatives, and more preferably anthracene derivatives and arylamine derivatives.
  • an anthracene derivative is preferable as the host material
  • an arylamine derivative is preferable as the dopant.
  • suitable materials described in International Publication No. 2010/134350 and International Publication No. 2010/134352 are selected.
  • the organic EL device of the present invention may have a light emitting layer containing a phosphorescent material, that is, a phosphorescent layer.
  • a material for the phosphorescent light emitting layer a known phosphorescent light emitting material can be used. Specifically, International Publication No. 2005/079118 may be referred to.
  • the dopant include iridium (Ir), osmium (Os), or platinum (Pt) metal orthometalated complexes, with iridium (Ir) orthometalated complexes being more preferred.
  • the host material is preferably a compound containing a carbazolyl group, more preferably a compound containing a carbazolyl group and a triazine skeleton, and even more preferably a compound containing two carbazolyl groups and one triazine skeleton.
  • the ring-forming carbon number of the anthracene derivative as the fluorescent light-emitting material is preferably 26 to 100, more preferably 26 to 80, and still more preferably 26 to 60. More specifically, the anthracene derivative is preferably an anthracene derivative represented by the following general formula (10).
  • Ar 31 and Ar 32 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a heterocyclic group having 5 to 50 ring atoms.
  • R 81 to R 88 each independently represents a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, substituted or unsubstituted A substituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted ring carbon number of 6 to 50 aryloxy groups, substituted or unsubstituted arylthio groups having 6 to 50 ring carbon atoms, substituted or unsub
  • the aryl group having 6 to 50 ring carbon atoms is preferably an aryl group having 6 to 40 ring carbon atoms, and more preferably an aryl group having 6 to 30 ring carbon atoms.
  • the heterocyclic group having 5 to 50 ring atoms is preferably a heterocyclic group having 5 to 40 ring atoms, and more preferably a heterocyclic group having 5 to 30 ring atoms.
  • the alkyl group having 1 to 50 carbon atoms is preferably an alkyl group having 1 to 30 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and further preferably an alkyl group having 1 to 5 carbon atoms.
  • the alkoxy group having 1 to 50 carbon atoms is preferably an alkoxy group having 1 to 30 carbon atoms, more preferably an alkoxy group having 1 to 10 carbon atoms, and further preferably an alkoxy group having 1 to 5 carbon atoms.
  • the aralkyl group having 7 to 50 carbon atoms is preferably an aralkyl group having 7 to 30 carbon atoms, and more preferably an aralkyl group having 7 to 20 carbon atoms.
  • the aryloxy group having 6 to 50 ring carbon atoms is preferably an aryloxy group having 6 to 40 ring carbon atoms, and more preferably an aryloxy group having 6 to 30 ring carbon atoms.
  • the arylthio group having 6 to 50 ring carbon atoms is preferably an arylthio group having 6 to 40 ring carbon atoms, and more preferably an arylthio group having 6 to 30 ring carbon atoms.
  • the alkoxycarbonyl group having 2 to 50 carbon atoms is preferably an alkoxycarbonyl group having 2 to 30 carbon atoms, more preferably an alkoxycarbonyl group having 2 to 10 carbon atoms, and further preferably an alkoxycarbonyl group having 2 to 5 carbon atoms.
  • the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.
  • Ar 31 and Ar 32 are preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
  • an anthracene derivative represented by the general formula (10) is preferable.
  • Ar 33 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a heterocyclic group having 5 to 50 ring atoms.
  • R 81 to R 88 are R 89 is the same as the definition of R 81 to R 88.
  • a is an integer of 1 to 7.
  • R 81 to R 88 are preferably the same as described above.
  • the preferred R 89 is also the same as R 81 to R 88 .
  • a is preferably an integer of 1 to 3, and more preferably 1 or 2.
  • the aryl group having 6 to 50 ring carbon atoms represented by Ar 33 is preferably an aryl group having 6 to 40 ring carbon atoms, more preferably an aryl group having 6 to 30 ring carbon atoms, and 6 to 6 ring forming carbon atoms.
  • a 20 aryl group is more preferred, and an aryl group having 6 to 12 ring carbon atoms is particularly preferred.
  • the arylamine derivative as the fluorescent light-emitting material is preferably an aryldiamine derivative, more preferably an aryldiamine derivative containing a pyrene skeleton, and further preferably an aryldiamine derivative containing a pyrene skeleton and a dibenzofuran skeleton. More specifically, as the aryldiamine derivative, an aryldiamine derivative represented by the following general formula (11) is preferable.
  • Ar 34 to Ar 37 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
  • L 21 represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms.
  • the aryl group having 6 to 50 ring carbon atoms is preferably an aryl group having 6 to 30 ring carbon atoms, more preferably an aryl group having 6 to 20 ring carbon atoms, and an aryl group having 6 to 12 ring carbon atoms.
  • a group is more preferable, and a phenyl group and a naphthyl group are particularly preferable.
  • the heteroaryl group having 5 to 50 ring atoms is preferably a heteroaryl group having 5 to 40 ring atoms, more preferably a heteroaryl group having 5 to 30 ring atoms, and 5 to 5 ring forming atoms. More preferred are 20 heteroaryl groups.
  • heteroaryl group examples include a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and the like, and a dibenzofuranyl group is preferable.
  • substituents for the heteroaryl group include aryl groups having 6 to 30 ring carbon atoms (preferably 6 to 20, more preferably 6 to 12), and more preferably a phenyl group and a naphthyl group.
  • the arylene group having 6 to 50 ring carbon atoms is preferably an arylene group having 6 to 40 ring carbon atoms, more preferably an arylene group having 6 to 30 ring carbon atoms, and an arylene group having 6 to 20 ring carbon atoms.
  • the group is more preferable, and the pyrenyl group is particularly preferable.
  • phosphorescent materials specific examples of the compound containing a carbazolyl group preferable as a host material include the following compounds.
  • the light emitting layer may be a double host (also referred to as a host / cohost). Specifically, the carrier balance in the light emitting layer may be adjusted by combining an electron transporting host and a hole transporting host in the light emitting layer. Moreover, it is good also as a double dopant.
  • each dopant emits light by adding two or more dopant materials having a high quantum yield. For example, a yellow light emitting layer may be realized by co-evaporating a host, a red dopant, and a green dopant.
  • the light emitting layer may contain a hole transport material, an electron transport material, and a polymer binder as necessary. Further, the thickness of the light emitting layer is preferably 5 to 50 nm, more preferably 7 to 50 nm, and most preferably 10 to 50 nm. If the thickness is less than 5 nm, it is difficult to form a light emitting layer, and it may be difficult to adjust the chromaticity. If the thickness exceeds 50 nm, the driving voltage may increase.
  • the electron injection / transport layer is a layer that assists the injection of electrons into the light emitting layer and transports it to the light emitting region, and has a high electron mobility.
  • these electron injecting / transporting layers it is a layer made of a material having particularly good adhesion to the cathode.
  • an electrode in this case, a cathode
  • the electron injecting / transporting layer is appropriately selected with a film thickness of several nm to several ⁇ m.
  • the electron mobility is preferably at least 10 ⁇ 5 cm 2 / Vs or more when an electric field of V / cm is applied.
  • 8-hydroxyquinoline or a metal complex of its derivative or an oxadiazole derivative is preferable.
  • a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline), for example, tris (8-quinolinol) aluminum is injected. It can be used as a material.
  • the electron injection material include compounds represented by any of the following formulas (31) to (36).
  • Z 1 , Z 2 and Z 3 are each independently a nitrogen atom or a carbon atom.
  • R 1 and R 2 are each independently a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, an alkyl group having 1 to 20 carbon atoms, halogen, An alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms substituted with an atom.
  • n is an integer of 0 to 5, and when n is an integer of 2 or more, the plurality of R 1 may be the same or different from each other.
  • R 1 may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
  • Ar 1 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms.
  • Ar 2 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms substituted by a halogen atom, an alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted 6 to 50 carbon atoms.
  • Ar 1 or Ar 2 is a substituted or unsubstituted condensed ring group having 10 to 50 carbon atoms or a substituted or unsubstituted hetero condensed ring group having 9 to 50 ring atoms.
  • Ar 3 is a substituted or unsubstituted arylene group having 6 to 50 carbon atoms or a substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms.
  • L 1 , L 2 and L 3 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, a substituted or unsubstituted hetero condensed ring group having 9 to 50 ring atoms, or a substituted group. Or it is an unsubstituted fluorenylene group.
  • Specific examples of the aryl group and alkyl group represented by R 1 , R 2 , Ar 1 , Ar 2 include the same examples as R 1 and R 2 in formula (1), and the alkoxy group includes its alkyl group.
  • An example in which an oxygen atom is bonded to is shown, and examples of the heteroaryl group include the same examples as Ar 31 in formula (h).
  • Examples of the arylene group represented by Ar 3 , L 1 , L 2, and L 3 include a divalent example of the aryl group, and examples of the hetero condensed ring group include a condensed ring group having a suitable number of carbon atoms in the hetero aryl group.
  • X is a condensed ring containing a nitrogen atom or a sulfur atom
  • Y is a single bond, alkyl chain, alkylene chain, cycloalkyl chain, aryl chain, heterocyclic chain, silyl chain, ether chain, or thioether chain.
  • q is a natural number of 2 or more.
  • the molecular weight of the compound represented by Formula (34) is 480 or more.
  • A is a substituent having a phenanthroline skeleton or a benzoquinoline skeleton.
  • B is a p-valent organic group having a structure represented by the following formula (35A). P is a natural number of 2 or more.
  • R 4 and R 5 are each independently an alkyl group or an aryl group (including an aryl group condensed to a phenyl group).
  • L and m are each independently a natural number from 0 to 5.
  • Z is at least one selected from the following formula (35B).
  • R 6 and R 7 may be the same or different and are each a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, Aryl ether group, aryl thioether group, aryl group, heteroaryl group, cyano group, carbonyl group, ester group, carbamoyl group, amino group, silyl group, and a condensed ring formed between adjacent substituents Ar 4 represents an aryl group or a heteroaryl group.
  • the organic EL device of the present invention has at least one of an electron donating dopant and an organometallic complex in the interface region between the cathode and the organic thin film layer. According to such a configuration, it is possible to improve the light emission luminance and extend the life of the organic EL element.
  • the electron donating dopant include at least one selected from alkali metals, alkali metal compounds, alkaline earth metals, alkaline earth metal compounds, rare earth metals, rare earth metal compounds, and the like.
  • the organometallic complex include at least one selected from an organometallic complex containing an alkali metal, an organometallic complex containing an alkaline earth metal, an organometallic complex containing a rare earth metal, and the like.
  • alkali metal examples include lithium (Li) (work function: 2.93 eV), sodium (Na) (work function: 2.36 eV), potassium (K) (work function: 2.28 eV), rubidium (Rb) (work Function: 2.16 eV), cesium (Cs) (work function: 1.95 eV), and the like, and those having a work function of 2.9 eV or less are preferable.
  • K, Rb, and Cs are preferred, Rb and Cs are more preferred, and Cs is most preferred.
  • alkaline earth metal examples include calcium (Ca) (work function: 2.9 eV), strontium (Sr) (work function: 2.0 eV to 2.5 eV), barium (Ba) (work function: 2.52 eV).
  • a work function of 2.9 eV or less is particularly preferable.
  • the rare earth metal examples include scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
  • preferred metals are particularly high in reducing ability, and by adding a relatively small amount to the electron injection region, it is possible to improve the light emission luminance and extend the life of the organic EL element.
  • alkali metal compound examples include lithium oxide (Li 2 O), cesium oxide (Cs 2 O), alkali oxides such as potassium oxide (K 2 O), lithium fluoride (LiF), sodium fluoride (NaF), fluorine.
  • alkali halides such as cesium fluoride (CsF) and potassium fluoride (KF), and lithium fluoride (LiF), lithium oxide (Li 2 O), and sodium fluoride (NaF) are preferable.
  • alkaline earth metal compound examples include barium oxide (BaO), strontium oxide (SrO), calcium oxide (CaO), and barium strontium oxide (Ba x Sr 1-x O) (0 ⁇ x ⁇ 1), Examples thereof include barium calcium oxide (Ba x Ca 1-x O) (0 ⁇ x ⁇ 1), and BaO, SrO, and CaO are preferable.
  • the rare earth metal compound ytterbium fluoride (YbF 3), scandium fluoride (ScF 3), scandium oxide (ScO 3), yttrium oxide (Y 2 O 3), cerium oxide (Ce 2 O 3), gadolinium fluoride (GdF 3), include such terbium fluoride (TbF 3) is, YbF 3, ScF 3, TbF 3 are preferable.
  • the organometallic complex is not particularly limited as long as it contains at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion as a metal ion as described above.
  • the ligands include quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiarylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines, and derivatives thereof are preferred, but are not limited thereto.
  • the electron donating dopant and the organometallic complex it is preferable to form a layer or an island in the interface region.
  • a forming method while depositing at least one of an electron donating dopant and an organometallic complex by a resistance heating vapor deposition method, an organic material as a light emitting material or an electron injection material for forming an interface region is simultaneously deposited, and an electron is deposited in the organic material.
  • a method of dispersing at least one of the donor dopant and the organometallic complex is preferable.
  • the dispersion concentration is usually organic substance: electron donating dopant and / or organometallic complex in a molar ratio of 100: 1 to 1: 100, preferably 5: 1 to 1: 5.
  • At least one of the electron donating dopant and the organometallic complex is formed in a layered form
  • at least one of the electron donating dopant and the organometallic complex is formed.
  • These are vapor-deposited by a resistance heating vapor deposition method alone, preferably with a layer thickness of 0.1 nm to 15 nm.
  • an electron donating dopant and an organometallic complex In the case where at least one of an electron donating dopant and an organometallic complex is formed in an island shape, a light emitting material or an electron injecting material which is an organic layer at the interface is formed in an island shape, and then the electron donating dopant and the organometallic complex are formed. At least one of them is vapor-deposited by a resistance heating vapor deposition method, preferably with an island thickness of 0.05 nm to 1 nm.
  • Electrode in order to inject electrons into the electron injecting / transporting layer or the light emitting layer, a material having a small work function (4 eV or less), an alloy, an electrically conductive compound and a mixture thereof are used as electrode materials. Used. Specific examples of such electrode materials include sodium, sodium / potassium alloy, magnesium, lithium, magnesium / silver alloy, aluminum / aluminum oxide, aluminum / lithium alloy, indium, and rare earth metals.
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the transmittance with respect to the light emitted from the cathode is larger than 10%.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually 10 nm to 1 ⁇ m, preferably 50 to 200 nm.
  • Insulating layer Since an organic EL element applies an electric field to an ultrathin film, pixel defects due to leakage or short-circuiting are likely to occur. In order to prevent this, it is preferable to insert an insulating thin film layer between the pair of electrodes.
  • the material used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, Examples thereof include germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and a mixture or a laminate thereof may be used.
  • An organic EL device is formed by forming an anode, a light emitting layer, a hole transport layer, and an electron injection / transport layer as required, and further forming a cathode by the materials and formation methods exemplified above.
  • An element can be manufactured.
  • an organic EL element can also be produced from the cathode to the anode in the reverse order.
  • an example of manufacturing an organic EL device having a structure in which an anode / hole transport layer / light emitting layer / electron injection / transport layer / cathode are sequentially provided on a translucent substrate will be described.
  • a thin film made of an anode material is formed on a suitable light-transmitting substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 10 to 200 nm, to produce an anode.
  • a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 10 to 200 nm, to produce an anode.
  • at least two or more hole transport layers are sequentially provided on the anode.
  • the hole transport layer can be formed by a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. However, it is easy to obtain a uniform film and pinholes are not easily generated. It is preferable to form by a vacuum evaporation method.
  • the deposition conditions vary depending on the compound used (the material of the hole transport layer), the crystal structure and recombination structure of the target hole transport layer, etc.
  • the source temperature is preferably selected from the range of 50 to 450 ° C., the degree of vacuum of 10 ⁇ 7 to 10 ⁇ 3 Torr, the deposition rate of 0.01 to 50 nm / second, the substrate temperature of ⁇ 50 to 300 ° C., and the film thickness of 5 nm to 5 ⁇ m. .
  • a light emitting layer in which a light emitting layer is provided on the hole transport layer is also performed by thinning the organic light emitting material using a desired organic light emitting material by a method such as vacuum deposition, sputtering, spin coating, or casting.
  • a vacuum deposition method from the viewpoint that a homogeneous film is easily obtained and pinholes are hardly generated.
  • the vapor deposition conditions vary depending on the compound used, but can generally be selected from the same condition range as that of the hole transport layer.
  • an electron injection / transport layer is provided on the light emitting layer.
  • an organic EL element can be obtained by laminating a cathode.
  • the cathode is made of metal, and vapor deposition or sputtering can be used.
  • vacuum deposition is preferred to protect the underlying organic layer from damage during film formation.
  • the organic EL element is preferably manufactured from the anode to the cathode consistently by a single vacuum.
  • Example 1 (Production of organic EL element) A 25 mm ⁇ 75 mm ⁇ 1.1 mm glass substrate with an ITO transparent electrode line (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and further UV (Ultraviolet) ozone cleaned for 30 minutes. A glass substrate with a transparent electrode line after cleaning is attached to a substrate holder of a vacuum deposition apparatus, and the following acceptor material (A) is vapor-deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed, An acceptor layer having a thickness of 5 nm was formed.
  • ITO transparent electrode line manufactured by Geomatic
  • the following compound (H1) was vapor-deposited as a first hole transport material to form a first hole transport layer having a film thickness of 65 nm.
  • the following compound (X1) was deposited as a second hole transport material to form a second hole transport layer having a thickness of 10 nm.
  • a compound (B) as a phosphorescent host material and Ir (ppy) 3 as a phosphorescent dopant were co-evaporated at a thickness of 25 nm to obtain a phosphorescent light emitting layer.
  • the concentration of Ir (ppy) 3 was 10% by mass.
  • a compound (C) having a thickness of 35 nm, LiF having a thickness of 1 nm, and metal Al having a thickness of 80 nm were sequentially laminated on the phosphorescent light emitting layer to form a cathode.
  • LiF which is an electron injecting electrode, was formed at a deposition rate of 1 ⁇ / min.
  • the obtained organic EL element is caused to emit light by direct current drive, and the luminance (cd / m 2 ) and current density are measured to obtain the light emission efficiency (cd / A) and drive voltage (V) at a current density of 10 mA / cm 2 . It was. Furthermore, the lifetime of the element that was 80% of the initial luminance at a current density of 50 mA / cm 2 was determined. The results are shown in Table 1.
  • Example 2 an organic EL device was produced in the same manner as in Example 1 except that the following compounds (H2) to (H8) were used instead of the compound (H1) as the first hole transport material.
  • the obtained organic EL element was made to emit light by direct current drive and evaluated in the same manner as in Example 1. The results are shown in Table 1.
  • Example 1 an organic EL device was produced in the same manner as in Example 1 except that the following comparative compounds 1 to 4 were used in place of the compound (H1) as the first hole transport material.
  • the obtained organic EL element was made to emit light by direct current drive and evaluated in the same manner as in Example 1. The results are shown in Table 1.
  • Comparative Example 5 (Production of organic EL element) A 25 mm ⁇ 75 mm ⁇ 1.1 mm glass substrate with an ITO transparent electrode line (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and further UV (Ultraviolet) ozone cleaned for 30 minutes. A glass substrate with a transparent electrode line after cleaning is attached to a substrate holder of a vacuum deposition apparatus, and the following acceptor material (A) is vapor-deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed, An acceptor layer having a thickness of 5 nm was formed.
  • ITO transparent electrode line manufactured by Geomatic
  • the compound (H1) was vapor-deposited as a hole transport material, and a hole transport layer having a thickness of 75 nm was formed.
  • a compound (B) as a phosphorescent host material and Ir (ppy) 3 as a phosphorescent dopant were co-evaporated at a thickness of 25 nm to obtain a phosphorescent light emitting layer.
  • the concentration of Ir (ppy) 3 was 10% by mass.
  • a compound (C) having a thickness of 35 nm, LiF having a thickness of 1 nm, and metal Al having a thickness of 80 nm were sequentially laminated on the phosphorescent light emitting layer to form a cathode.
  • LiF which is an electron injecting electrode
  • the obtained organic EL element is caused to emit light by direct current drive, and the luminance (cd / m 2 ) and current density are measured to obtain the light emission efficiency (cd / A) and drive voltage (V) at a current density of 10 mA / cm 2 . It was. Furthermore, the lifetime of the element that was 80% of the initial luminance at a current density of 50 mA / cm 2 was determined. The results are shown in Table 1.
  • Example 9 the compound (H8) was used instead of the compound (H1) as the first hole transport material, and the following compound (Y1) was used instead of the compound (X1) as the second hole transport material.
  • An organic EL device was prepared in the same manner as in Example 1 except that any one of (Y9) was used and Ir (bzq) 3 was used instead of Ir (ppy) 3 as a phosphorescent dopant. And evaluated. The results are shown in Table 2.
  • Example 9 an organic EL device was produced in the same manner as in Example 9 except that the comparative compounds 1 to 4 were used in place of the aromatic amine derivative (H8) as the first hole transport material. Evaluation was performed in the same manner as in Example 1. The results are shown in Table 2.
  • Example 18 (Production of organic EL element) A 25 mm ⁇ 75 mm ⁇ 1.1 mm glass substrate with an ITO transparent electrode line (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and further UV (Ultraviolet) ozone cleaned for 30 minutes. A glass substrate with a transparent electrode line after cleaning is attached to a substrate holder of a vacuum deposition apparatus, and the following acceptor material (A) is vapor-deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed, An acceptor layer having a thickness of 5 nm was formed.
  • ITO transparent electrode line manufactured by Geomatic
  • the compound (H8) was deposited as a first hole transport material to form a first hole transport layer having a thickness of 138 nm.
  • the following compound (Y1) was deposited as the second hole transport material to form a second hole transport layer having a thickness of 10 nm.
  • a compound (B2) as a fluorescent host material and (BD) as a fluorescent dopant were co-evaporated to obtain a fluorescent light emitting layer having a thickness of 25 nm.
  • concentration of the dopant (BD) in a fluorescence light emitting layer was 5 mass%.
  • the following compound (C2) having a thickness of 20 nm, the following compound (C) having a thickness of 5 nm, LiF having a thickness of 1 nm, and metal Al having a thickness of 80 nm are sequentially laminated on the fluorescent light emitting layer to form a cathode.
  • LiF which is an electron injecting electrode
  • the obtained organic EL element is caused to emit light by direct current drive, and the luminance (cd / m 2 ) and current density are measured to obtain the light emission efficiency (cd / A) and drive voltage (V) at a current density of 10 mA / cm 2 . It was.
  • the lifetime of the element that was 80% of the initial luminance at a current density of 50 mA / cm 2 was determined. The results are shown in Table 3.
  • Example 18 an organic EL device was produced in the same manner as in Example 18 except that the compounds (Y2) and (Y3) were used as the second hole transport material instead of the compound (Y1).
  • the obtained organic EL element was made to emit light by direct current drive and evaluated in the same manner as in Example 1. The results are shown in Table 3.
  • Example 18 an organic EL device was produced in the same manner as in Example 18 except that Comparative Compounds 1 to 4 were used instead of the aromatic amine derivative (H8) as the first hole transport material. Evaluation was performed in the same manner as in Example 1. The results are shown in Table 3.
  • the organic EL device using the compound of the formula (1) for the first hole transporting layer has a compound other than the compound of the formula (1). It can be seen that the efficiency can be increased and the lifetime of the element is longer than that of the organic EL element used for the first hole transport layer.
  • the organic EL device of the present invention can thicken the hole transport layer, enable adjustment of the optical film thickness of the organic EL device, and improve the light emission efficiency and life of the device. For this reason, it is useful as a flat light emitter or a backlight of a display.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un élément électroluminescent organique présentant, entre une électrode positive et une électrode négative opposées, au moins deux couches de transport de trou, et une couche électroluminescente, dans cet ordre, et est caractérisée en ce qu'une des couches de transport de trou contient un composé de structure spécifique présentant une structure fluorène au centre et n'est pas adjacente à la couche électroluminescente. Dans cet élément électroluminescent organique, la couche de transport de trou peut être plus épaisse, l'épaisseur du film optique peut être ajustée, et la performance de l'élément peut être améliorée.
PCT/JP2013/052842 2012-02-10 2013-02-07 Élément électroluminescent organique WO2013118812A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2012-027828 2012-02-10
JP2012027828 2012-02-10
JP2012-091366 2012-04-12
JP2012091366 2012-04-12

Publications (1)

Publication Number Publication Date
WO2013118812A1 true WO2013118812A1 (fr) 2013-08-15

Family

ID=48947569

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2013/052842 WO2013118812A1 (fr) 2012-02-10 2013-02-07 Élément électroluminescent organique

Country Status (3)

Country Link
JP (1) JP2013236055A (fr)
TW (1) TW201341346A (fr)
WO (1) WO2013118812A1 (fr)

Cited By (74)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014157018A1 (fr) * 2013-03-26 2014-10-02 Semiconductor Energy Laboratory Co., Ltd. Composé organique, élément luminescent, dispositif luminescent, dispositif d'affichage, dispositif électronique, et dispositif d'éclairage
EP3056504A1 (fr) 2015-02-16 2016-08-17 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3061763A1 (fr) 2015-02-27 2016-08-31 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3098229A1 (fr) 2015-05-15 2016-11-30 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3101021A1 (fr) 2015-06-01 2016-12-07 Universal Display Corporation Materiaux electroluminescents organiques et dispositfs
EP3124488A1 (fr) 2015-07-29 2017-02-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP3159350A1 (fr) 2015-09-03 2017-04-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
CN106674026A (zh) * 2016-12-28 2017-05-17 上海天马有机发光显示技术有限公司 一种空穴传输材料、包含其的oled显示面板和电子设备
EP3205658A1 (fr) 2016-02-09 2017-08-16 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3231809A2 (fr) 2016-04-11 2017-10-18 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
US9806276B2 (en) 2015-09-18 2017-10-31 Lg Display Co., Ltd. Organic light emitting display apparatus
EP3261147A1 (fr) 2016-06-20 2017-12-27 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3261146A2 (fr) 2016-06-20 2017-12-27 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3270435A2 (fr) 2016-06-20 2018-01-17 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3297051A1 (fr) 2016-09-14 2018-03-21 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3301088A1 (fr) 2016-10-03 2018-04-04 Universal Display Corporation Pyridines condensées et tant que matériaux et dispositifs électroluminescents organiques
EP3305796A1 (fr) 2016-10-07 2018-04-11 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3321258A1 (fr) 2016-11-09 2018-05-16 Universal Display Corporation Complexes d'iridium avec 4-phénylbenzo[g]quinazoline ou 4-(3,5-dimethylphenylbenzo[g]quinazoline à être utilisés en tant que matériaux émetteurs dans le proche infrarouge or infrarouge de lumière dans des oleds
EP3323822A1 (fr) 2016-09-23 2018-05-23 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
US10014477B2 (en) 2012-08-31 2018-07-03 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element using same
EP3345914A1 (fr) 2017-01-09 2018-07-11 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3354654A2 (fr) 2016-11-11 2018-08-01 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
US10056558B2 (en) 2011-11-25 2018-08-21 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, material for organic electroluminescent element, and organic electroluminescent element
EP3381927A1 (fr) 2017-03-29 2018-10-03 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3401318A1 (fr) 2017-05-11 2018-11-14 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3418286A1 (fr) 2017-06-23 2018-12-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3444258A2 (fr) 2017-08-10 2019-02-20 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3489243A1 (fr) 2017-11-28 2019-05-29 University of Southern California Composés de carbène et dispositifs électroluminescents organiques
EP3492528A1 (fr) 2017-11-30 2019-06-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3492480A2 (fr) 2017-11-29 2019-06-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3613751A1 (fr) 2018-08-22 2020-02-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3690973A1 (fr) 2019-01-30 2020-08-05 University Of Southern California Matériaux et dispositifs électroluminescents organiques
EP3689889A1 (fr) 2019-02-01 2020-08-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3715353A1 (fr) 2019-03-26 2020-09-30 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3750897A1 (fr) 2019-06-10 2020-12-16 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3771717A1 (fr) 2019-07-30 2021-02-03 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3778614A1 (fr) 2019-08-16 2021-02-17 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3816175A1 (fr) 2019-11-04 2021-05-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
US11053229B2 (en) 2017-03-08 2021-07-06 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
EP3845545A1 (fr) 2020-01-06 2021-07-07 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3858945A1 (fr) 2020-01-28 2021-08-04 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3937268A1 (fr) 2020-07-10 2022-01-12 Universal Display Corporation Delo plasmoniques et émetteurs à dipôle vertical
EP4001286A1 (fr) 2020-11-24 2022-05-25 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4001287A1 (fr) 2020-11-24 2022-05-25 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4016659A1 (fr) 2020-11-16 2022-06-22 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4019526A1 (fr) 2018-01-26 2022-06-29 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4039692A1 (fr) 2021-02-03 2022-08-10 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4053137A1 (fr) 2021-03-05 2022-09-07 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4056578A1 (fr) 2021-03-12 2022-09-14 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4059941A1 (fr) 2021-03-15 2022-09-21 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4059915A2 (fr) 2021-02-26 2022-09-21 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4060758A2 (fr) 2021-02-26 2022-09-21 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4075531A1 (fr) 2021-04-13 2022-10-19 Universal Display Corporation Delo plasmoniques et émetteurs à dipôle vertical
EP4074723A1 (fr) 2021-04-05 2022-10-19 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4075530A1 (fr) 2021-04-14 2022-10-19 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4079743A1 (fr) 2021-04-23 2022-10-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4086266A1 (fr) 2021-04-23 2022-11-09 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4112701A2 (fr) 2021-06-08 2023-01-04 University of Southern California Alignement moléculaire de phosphores homoleptiques d'iridium
EP4151699A1 (fr) 2021-09-17 2023-03-22 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4185086A1 (fr) 2017-07-26 2023-05-24 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4212539A1 (fr) 2021-12-16 2023-07-19 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4231804A2 (fr) 2022-02-16 2023-08-23 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4242285A1 (fr) 2022-03-09 2023-09-13 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4265626A2 (fr) 2022-04-18 2023-10-25 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4282863A1 (fr) 2022-05-24 2023-11-29 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4293001A1 (fr) 2022-06-08 2023-12-20 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4299693A1 (fr) 2022-06-28 2024-01-03 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4326030A1 (fr) 2022-08-17 2024-02-21 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4362645A2 (fr) 2022-10-27 2024-05-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4362630A2 (fr) 2022-10-27 2024-05-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4362631A2 (fr) 2022-10-27 2024-05-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4369898A1 (fr) 2022-10-27 2024-05-15 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4376583A2 (fr) 2022-10-27 2024-05-29 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4386065A1 (fr) 2022-12-14 2024-06-19 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015122459A (ja) * 2013-12-25 2015-07-02 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機ｅｌ素子
KR101878398B1 (ko) * 2014-05-30 2018-07-13 제일모직 주식회사 유기 광전자 소자 및 표시 장치
JP6468800B2 (ja) 2014-10-29 2019-02-13 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． アミン誘導体、有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11162649A (ja) * 1997-11-28 1999-06-18 Mitsui Chem Inc 有機エレクトロルミネッセンス素子
JPH11224779A (ja) * 1998-02-04 1999-08-17 Mitsui Chem Inc 有機電界発光素子
WO2006114921A1 (fr) * 2005-04-18 2006-11-02 Idemitsu Kosan Co., Ltd. Compose triamine aromatique et dispositif electroluminescent organique l'utilisant
US20070082226A1 (en) * 2005-10-07 2007-04-12 Au Optronics Corp. Organic light emitting diode and display device employing the same
JP2009010338A (ja) * 2007-04-30 2009-01-15 Novaled Ag オキソカーボン化合物、擬似オキソカーボン化合物、及びラジアレン化合物、並びにこれらの利用方法
WO2010098458A1 (fr) * 2009-02-27 2010-09-02 出光興産株式会社 Élément électroluminescent organique
WO2010114017A1 (fr) * 2009-04-01 2010-10-07 出光興産株式会社 Elément électroluminescent organique
JP2010270103A (ja) * 2009-04-23 2010-12-02 Canon Inc 新規有機化合物および発光素子および画像表示装置

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11162649A (ja) * 1997-11-28 1999-06-18 Mitsui Chem Inc 有機エレクトロルミネッセンス素子
JPH11224779A (ja) * 1998-02-04 1999-08-17 Mitsui Chem Inc 有機電界発光素子
WO2006114921A1 (fr) * 2005-04-18 2006-11-02 Idemitsu Kosan Co., Ltd. Compose triamine aromatique et dispositif electroluminescent organique l'utilisant
US20070082226A1 (en) * 2005-10-07 2007-04-12 Au Optronics Corp. Organic light emitting diode and display device employing the same
JP2009010338A (ja) * 2007-04-30 2009-01-15 Novaled Ag オキソカーボン化合物、擬似オキソカーボン化合物、及びラジアレン化合物、並びにこれらの利用方法
WO2010098458A1 (fr) * 2009-02-27 2010-09-02 出光興産株式会社 Élément électroluminescent organique
WO2010114017A1 (fr) * 2009-04-01 2010-10-07 出光興産株式会社 Elément électroluminescent organique
JP2010270103A (ja) * 2009-04-23 2010-12-02 Canon Inc 新規有機化合物および発光素子および画像表示装置

Cited By (103)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10056558B2 (en) 2011-11-25 2018-08-21 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, material for organic electroluminescent element, and organic electroluminescent element
US10014477B2 (en) 2012-08-31 2018-07-03 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element using same
US11444246B2 (en) 2012-08-31 2022-09-13 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element using same
US11362279B2 (en) 2012-08-31 2022-06-14 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element using same
US10446766B2 (en) 2013-03-26 2019-10-15 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, light-emitting device, display device, electronic device, and lighting device
US9634263B2 (en) 2013-03-26 2017-04-25 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, light-emitting device, display device, electronic device, and lighting device
WO2014157018A1 (fr) * 2013-03-26 2014-10-02 Semiconductor Energy Laboratory Co., Ltd. Composé organique, élément luminescent, dispositif luminescent, dispositif d'affichage, dispositif électronique, et dispositif d'éclairage
US10347847B2 (en) 2013-03-26 2019-07-09 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, light-emitting device, display device, electronic device, and lighting device
EP3056504A1 (fr) 2015-02-16 2016-08-17 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3061763A1 (fr) 2015-02-27 2016-08-31 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3098229A1 (fr) 2015-05-15 2016-11-30 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3101021A1 (fr) 2015-06-01 2016-12-07 Universal Display Corporation Materiaux electroluminescents organiques et dispositfs
EP3124488A1 (fr) 2015-07-29 2017-02-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP3760635A1 (fr) 2015-09-03 2021-01-06 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3159350A1 (fr) 2015-09-03 2017-04-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
US9806276B2 (en) 2015-09-18 2017-10-31 Lg Display Co., Ltd. Organic light emitting display apparatus
EP3858842A1 (fr) 2016-02-09 2021-08-04 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3205658A1 (fr) 2016-02-09 2017-08-16 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3231809A2 (fr) 2016-04-11 2017-10-18 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4122941A1 (fr) 2016-04-11 2023-01-25 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4349935A2 (fr) 2016-06-20 2024-04-10 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP3261146A2 (fr) 2016-06-20 2017-12-27 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3758084A1 (fr) 2016-06-20 2020-12-30 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3261147A1 (fr) 2016-06-20 2017-12-27 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3920254A1 (fr) 2016-06-20 2021-12-08 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3270435A2 (fr) 2016-06-20 2018-01-17 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3843171A1 (fr) 2016-06-20 2021-06-30 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3297051A1 (fr) 2016-09-14 2018-03-21 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3323822A1 (fr) 2016-09-23 2018-05-23 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3301088A1 (fr) 2016-10-03 2018-04-04 Universal Display Corporation Pyridines condensées et tant que matériaux et dispositifs électroluminescents organiques
EP3858844A1 (fr) 2016-10-07 2021-08-04 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3305796A1 (fr) 2016-10-07 2018-04-11 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3789379A1 (fr) 2016-11-09 2021-03-10 Universal Display Corporation Complexes d'iridium avec 4-phénylbenzo[g]quinazoline ou 4-(3,5-dimethylphenylbenzo[g]quinazoline à être utilisés en tant que matériaux émetteurs dans le proche infrarouge or infrarouge de lumière dans des oleds
EP3321258A1 (fr) 2016-11-09 2018-05-16 Universal Display Corporation Complexes d'iridium avec 4-phénylbenzo[g]quinazoline ou 4-(3,5-dimethylphenylbenzo[g]quinazoline à être utilisés en tant que matériaux émetteurs dans le proche infrarouge or infrarouge de lumière dans des oleds
EP4092036A1 (fr) 2016-11-11 2022-11-23 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3354654A2 (fr) 2016-11-11 2018-08-01 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
CN106674026A (zh) * 2016-12-28 2017-05-17 上海天马有机发光显示技术有限公司 一种空穴传输材料、包含其的oled显示面板和电子设备
EP3689890A1 (fr) 2017-01-09 2020-08-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3345914A1 (fr) 2017-01-09 2018-07-11 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4212540A1 (fr) 2017-01-09 2023-07-19 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
US11053229B2 (en) 2017-03-08 2021-07-06 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
EP3985012A1 (fr) 2017-03-29 2022-04-20 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3730506A1 (fr) 2017-03-29 2020-10-28 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3381927A1 (fr) 2017-03-29 2018-10-03 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4141010A1 (fr) 2017-05-11 2023-03-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP3401318A1 (fr) 2017-05-11 2018-11-14 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3418286A1 (fr) 2017-06-23 2018-12-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4185086A1 (fr) 2017-07-26 2023-05-24 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP3783006A1 (fr) 2017-08-10 2021-02-24 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3444258A2 (fr) 2017-08-10 2019-02-20 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3878855A1 (fr) 2017-11-28 2021-09-15 University of Southern California Composés de carbène et dispositifs électroluminescents organiques
EP3489243A1 (fr) 2017-11-28 2019-05-29 University of Southern California Composés de carbène et dispositifs électroluminescents organiques
EP3492480A2 (fr) 2017-11-29 2019-06-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3492528A1 (fr) 2017-11-30 2019-06-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4019526A1 (fr) 2018-01-26 2022-06-29 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3613751A1 (fr) 2018-08-22 2020-02-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4206210A1 (fr) 2018-08-22 2023-07-05 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP3690973A1 (fr) 2019-01-30 2020-08-05 University Of Southern California Matériaux et dispositifs électroluminescents organiques
EP4301117A2 (fr) 2019-02-01 2024-01-03 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3689889A1 (fr) 2019-02-01 2020-08-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3715353A1 (fr) 2019-03-26 2020-09-30 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4134371A2 (fr) 2019-03-26 2023-02-15 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3750897A1 (fr) 2019-06-10 2020-12-16 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4219515A1 (fr) 2019-07-30 2023-08-02 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP3771717A1 (fr) 2019-07-30 2021-02-03 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3778614A1 (fr) 2019-08-16 2021-02-17 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3816175A1 (fr) 2019-11-04 2021-05-05 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4151644A1 (fr) 2020-01-06 2023-03-22 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP3845545A1 (fr) 2020-01-06 2021-07-07 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3858945A1 (fr) 2020-01-28 2021-08-04 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4294157A2 (fr) 2020-01-28 2023-12-20 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP3937268A1 (fr) 2020-07-10 2022-01-12 Universal Display Corporation Delo plasmoniques et émetteurs à dipôle vertical
EP4016659A1 (fr) 2020-11-16 2022-06-22 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4001286A1 (fr) 2020-11-24 2022-05-25 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4329463A2 (fr) 2020-11-24 2024-02-28 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4001287A1 (fr) 2020-11-24 2022-05-25 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4039692A1 (fr) 2021-02-03 2022-08-10 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4060758A2 (fr) 2021-02-26 2022-09-21 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4059915A2 (fr) 2021-02-26 2022-09-21 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4053137A1 (fr) 2021-03-05 2022-09-07 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4056578A1 (fr) 2021-03-12 2022-09-14 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4059941A1 (fr) 2021-03-15 2022-09-21 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4074723A1 (fr) 2021-04-05 2022-10-19 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4075531A1 (fr) 2021-04-13 2022-10-19 Universal Display Corporation Delo plasmoniques et émetteurs à dipôle vertical
EP4075530A1 (fr) 2021-04-14 2022-10-19 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4086266A1 (fr) 2021-04-23 2022-11-09 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4079743A1 (fr) 2021-04-23 2022-10-26 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4112701A2 (fr) 2021-06-08 2023-01-04 University of Southern California Alignement moléculaire de phosphores homoleptiques d'iridium
EP4151699A1 (fr) 2021-09-17 2023-03-22 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4212539A1 (fr) 2021-12-16 2023-07-19 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4231804A2 (fr) 2022-02-16 2023-08-23 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
EP4242285A1 (fr) 2022-03-09 2023-09-13 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4265626A2 (fr) 2022-04-18 2023-10-25 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4282863A1 (fr) 2022-05-24 2023-11-29 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4293001A1 (fr) 2022-06-08 2023-12-20 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4299693A1 (fr) 2022-06-28 2024-01-03 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4326030A1 (fr) 2022-08-17 2024-02-21 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4362645A2 (fr) 2022-10-27 2024-05-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4362630A2 (fr) 2022-10-27 2024-05-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4362631A2 (fr) 2022-10-27 2024-05-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4369898A1 (fr) 2022-10-27 2024-05-15 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4376583A2 (fr) 2022-10-27 2024-05-29 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
EP4386065A1 (fr) 2022-12-14 2024-06-19 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs

Also Published As

Publication number Publication date
JP2013236055A (ja) 2013-11-21
TW201341346A (zh) 2013-10-16

Similar Documents

Publication Publication Date Title
JP5988887B2 (ja) 芳香族アミン誘導体、有機エレクトロルミネッセンス素子及び電子機器
WO2013118812A1 (fr) Élément électroluminescent organique
JP5215481B2 (ja) 有機電界発光素子
US9601708B2 (en) Organic light emitting device and materials for use in same
JP5662994B2 (ja) 有機電界発光素子
JP5898194B2 (ja) 有機エレクトロルミネッセンス素子
US9966539B2 (en) Organic electroluminescence device
WO2014069602A1 (fr) Élément électroluminescent organique
WO2014087657A1 (fr) Dérivé d'amine aromatique et élément électroluminescent organique
TW201317326A (zh) 有機電激發光元件用材料及使用其之有機電激發光元件
EP2560220A1 (fr) Élément électroluminescent organique
JP2012156499A (ja) 有機エレクトロルミネッセンス素子
JP2013201153A (ja) 有機エレクトロルミネッセンス素子
WO2015050173A1 (fr) Composé, élément électroluminescent organique, et dispositif électronique
WO2015053403A1 (fr) Composé amine aromatique, élément électroluminescent organique et dispositif électronique
JP2014049539A (ja) 有機エレクトロルミネッセンス素子
JP6446362B2 (ja) アミン化合物及び有機エレクトロルミネッセンス素子
KR101177172B1 (ko) 신규한 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자
JP2013177386A (ja) 芳香族アミン誘導体、有機エレクトロルミネッセンス素子及び電子機器
TW201538514A (zh) 有機電場發光元件用材料以及使用其的有機電場發光元件
US8941099B2 (en) Organic light emitting device and materials for use in same
WO2014057659A1 (fr) Composé, et élément électroluminescent organique produit à l'aide de ce composé
WO2014010611A1 (fr) Élément d'électroluminescence organique et appareil électronique

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 13747330

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 13747330

Country of ref document: EP

Kind code of ref document: A1