WO2014046495A1 - Diode électroluminescente dotée d'une nouvelle structure et appareil électronique la contenant - Google Patents

Diode électroluminescente dotée d'une nouvelle structure et appareil électronique la contenant Download PDF

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WO2014046495A1
WO2014046495A1 PCT/KR2013/008466 KR2013008466W WO2014046495A1 WO 2014046495 A1 WO2014046495 A1 WO 2014046495A1 KR 2013008466 W KR2013008466 W KR 2013008466W WO 2014046495 A1 WO2014046495 A1 WO 2014046495A1
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carbon atoms
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light emitting
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최정옥
정준호
권오관
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주식회사 엘엠에스
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Priority to US14/429,948 priority Critical patent/US9614163B2/en
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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    • 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

Definitions

  • the present invention relates to a light emitting device having a novel structure and an electronic device including the same.
  • a light emitting device includes a light emitting layer including two electrodes facing each other and a light emitting compound interposed between the electrodes. When a current flows between the electrodes, the light emitting compound generates light.
  • the display device using the light emitting device does not need a separate light source device, and thus the weight, size, and thickness of the display device can be reduced.
  • the display device using the light emitting device has an advantage of excellent viewing angle, contrast ratio, color reproducibility, and the like, and lower power consumption than the display device using the backlight and the liquid crystal.
  • materials used as the organic material layer of the organic light emitting device may be classified into light emitting materials, hole injection materials, hole transport materials, electron transport materials, and electron injection materials according to functions.
  • the light emitting material may be classified into a polymer type and a low molecular type according to the molecular weight, and may be classified into a blue, green, red light emitting material, or the like according to the light emission color.
  • a problem may occur in that the maximum light emission wavelength is shifted to a long wavelength due to intermolecular interaction, and color efficiency is reduced or device efficiency is reduced due to light emission attenuation effect.
  • a light emitting layer made of a host / dopant system may be applied to the light emitting device.
  • the exciton formed in the light emitting layer is transferred to the dopant, so that the light emitting device can emit light efficiently.
  • the light emitting device has a short light emitting life and low power efficiency.
  • various compounds have been developed as materials of the light emitting device, but there are limitations in manufacturing a light emitting device that satisfies both the light emission life and power efficiency.
  • Patent Document 1 Japanese Patent No. 4807013
  • Patent Document 2 Japanese Patent Application Laid-Open No. 2012-067077
  • Patent Document 3 Korean Patent Publication No. 2006-0134979
  • an object of the present invention is to provide a novel structure capable of improving the luminous efficiency and increasing the lifetime in a light emitting device.
  • Still another object of the present invention is to provide an electronic device including the light emitting device.
  • a light emitting device for realizing the object of the present invention, the first electrode; Second electrode; A light emitting layer disposed between the first electrode and the second electrode; A hole transport layer disposed between the first electrode and the light emitting layer; And a blocking layer disposed between the hole transporting layer and the light emitting layer and comprising a compound represented by the following Chemical Formula 1.
  • X and Y each independently represent NL c -Ar 1 , S, O or Si (R 1 ) (R 2 ),
  • One of X and Y is NL c -Ar 1 , the other is S, O or Si (R 1 ) (R 2 ),
  • Z 1 and Z 2 are each independently represented by hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, the following Chemical Formula 2 or the following Chemical Formula 3,
  • Ar 1 , Ar 2 and Ar 3 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, carbon atoms A heterocycloalkyl group having 2 to 20, a bicycloalkyl group having 7 to 20 carbon atoms, or the following general formula (4)
  • W 1 and W 2 each independently represent NL f -Ar 4 , O, S or Si (R 7 ) (R 8 ),
  • R 1 , R 2 , R 7 and R 8 each independently represent an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms,
  • R 3 , R 4 , R 5 and R 6 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms,
  • n represents an integer of 0 to 4
  • L a , L b , L c , L d , L e and L f each independently represent * -L 1 -L 2 -L 3 -L 4- *,
  • L 1 , L 2 , L 3 and L 4 are each independently a single bond, -O-, -S-, a straight or branched alkylene group having 1 to 20 carbon atoms (-(CH 2 ) j- , wherein j is an integer of 1 to 20), an arylene group having 6 to 20 carbon atoms, a heteroarylene group having 2 to 20 carbon atoms, a cycloalkylene group having 3 to 20 carbon atoms, a heterocycloalkylene group having 2 to 20 carbon atoms, or 7 carbon atoms Bicycloalkylene group having from 20 to 20,
  • Ar 4 is hydrogen, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 2 to 30 carbon atoms, or A bicycloalkyl group having 7 to 30 carbon atoms,
  • At least one of the hydrogen of Formula 1 is each independently an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an amine group substituted with at least one alkyl group having 1 to 6 carbon atoms, aryl having 6 to 30 carbon atoms Group, heteroaryl group having 2 to 20 carbon atoms, aryloxy group having 6 to 20 carbon atoms, arylthio group having 6 to 20 carbon atoms, alkoxycarbonyl group having 1 to 6 carbon atoms, halogen group, cyano group, nitro group, hydroxide Unsubstituted or substituted with one or more substituents selected from the group consisting of a period and a carboxy group.
  • the present invention discloses an electronic device including the light emitting device.
  • the light emitting device provides improved luminous efficiency, increased lifetime and good thermal stability (heat resistance).
  • FIG. 1 is a cross-sectional view illustrating a light emitting device according to an embodiment of the present invention.
  • FIG. 2 is a cross-sectional view illustrating a light emitting device according to another embodiment of the present invention.
  • FIG. 3 is a cross-sectional view for describing a light emitting device according to still another embodiment of the present invention.
  • the light emitting device is disposed between the first electrode, the second electrode, the light emitting layer disposed between the first electrode and the second electrode, the hole transporting layer disposed between the first electrode and the light emitting layer and between the hole transporting layer and the light emitting layer It includes a barrier layer containing a compound represented by the following formula (1).
  • X and Y each independently represent NL c -Ar 1 , S, O or Si (R 1 ) (R 2 ),
  • One of X and Y is NL c -Ar 1 , the other is S, O or Si (R 1 ) (R 2 ),
  • Z 1 and Z 2 are each independently represented by hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, the following Chemical Formula 2 or the following Chemical Formula 3,
  • Ar 1 , Ar 2 and Ar 3 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, carbon atoms A heterocycloalkyl group having 2 to 20, a bicycloalkyl group having 7 to 20 carbon atoms, or the following general formula (4)
  • W 1 and W 2 each independently represent NL f -Ar 4 , O, S or Si (R 7 ) (R 8 ),
  • R 1 , R 2 , R 7 and R 8 each independently represent an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms,
  • R 3 , R 4 , R 5 and R 6 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms,
  • n represents an integer of 0 to 4
  • L a , L b , L c , L d , L e and L f each independently represent * -L 1 -L 2 -L 3 -L 4- *,
  • L 1 , L 2 , L 3 and L 4 are each independently a single bond, -O-, -S-, a straight or branched alkylene group having 1 to 20 carbon atoms (-(CH 2 ) j- , wherein j is an integer of 1 to 20), an arylene group having 6 to 20 carbon atoms, a heteroarylene group having 2 to 20 carbon atoms, a cycloalkylene group having 3 to 20 carbon atoms, a heterocycloalkylene group having 2 to 20 carbon atoms, or 7 carbon atoms Bicycloalkylene group having from 20 to 20,
  • Ar 4 is hydrogen, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocycloalkyl group having 2 to 30 carbon atoms, or A bicycloalkyl group having 7 to 30 carbon atoms,
  • At least one of the hydrogen of Formula 1 is each independently an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an amine group substituted with at least one alkyl group having 1 to 6 carbon atoms, aryl having 6 to 30 carbon atoms Group, heteroaryl group having 2 to 20 carbon atoms, aryloxy group having 6 to 20 carbon atoms, arylthio group having 6 to 20 carbon atoms, alkoxycarbonyl group having 1 to 6 carbon atoms, halogen group, cyano group, nitro group, hydroxide Unsubstituted or substituted with one or more substituents selected from the group consisting of a period and a carboxyl group.
  • an "alkyl group” is defined as a functional group derived from linear or branched saturated hydrocarbons.
  • alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, sec-butyl group, t-butyl group, n-pentyl group, 1,1-dimethylpropyl group, 1 , 2-dimethylpropyl group (1,2-dimethylpropyl group), 2,2-dimethylpropyl group (2,2-dimethylpropyl group), 1-ethylpropyl group (1-ethylpropyl group), 2-ethylpropyl group (2 -ethylpropyl group), n-hexyl group, 1-methyl-2-ethylpropyl group, 1-ethyl-2-methylpropyl group (1-ethyl- 2-methylpropyl group), 1,1,2-trimethylpropyl group (1,1,2-trimethylpropyl group), 1-propylpropyl group (1-propylpropyl group), 1-methylmethyl group
  • the alkyl group has 1 to 20 carbon atoms, for example 1 to 12 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms.
  • aryl group is defined as a monovalent substituent derived from an aromatic hydrocarbon.
  • aryl group examples include a phenyl group, a naphthyl group, an anthracenyl group, a naphthacenyl group, a pyrenyl group, a tolyl group, Biphenyl group, terphenyl group, chrycenyl group, spirobifluorenyl group, fluoranthenyl group, fluorenyl group, fluorenyl group Perylenyl group, indenyl group, azulenyl group, azulenyl group, heptalenyl group, phenalenyl group, phenanthrenyl group, and the like. .
  • the aryl group has 6 to 30 carbon atoms, for example, 6 to 18 carbon atoms, or 6 to 12 carbon atoms.
  • Heteroaryl group refers to "aromatic heterocycle” derived from a monocyclic or condensed ring.
  • the heteroaryl group at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se) and silicon (Si) as a hetero atom, for example, one, two, It can include three or four.
  • heteroaryl group examples include a pyrrolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazolyl group (triazolyl group, tetrazolyl group, benzotriazolyl group, benzotriazolyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, indole Indolyl group, isoindolyl group, indolizinyl group, indolinzinyl group, purinyl group, inindazolyl group, quinolyl group, quinolyl group, isoquinolyl Isoquinolinyl group, quinolizinyl group, phthalazinyl group, phthalazinyl group, naphthylidinyl group, quinoxalinyl group, quinazolinyl group, quinazolinyl group,
  • heteroaryl group may include a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a benzothiadiazolyl group, and a phenothiazinyl group.
  • phenothiazinyl group isoxazolyl group, furazanyl group, furazanyl group, phenoxazinyl group, oxazolyl group, benzoxazolyl group, benzoxazolyl group
  • Compounds containing at least two or more heteroatoms such as an oxadiazolyl group, a pyrazoloxazolyl group, an imidazothiazolyl group, a thienofuranyl group, and the like have.
  • the heteroaryl group may have 2 to 20 carbon atoms, for example, 3 to 19 carbon atoms, 4 to 15 carbon atoms, or 5 to 11 carbon atoms.
  • the heteroaryl group may have a ring member of 5 to 21.
  • a "cycloalkyl group” is defined as a functional group derived from a monocyclic saturated hydrocarbon.
  • cycloalkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, or a cyclooctyl group (cyclooctyl group) etc. are mentioned.
  • the cycloalkyl group has 3 to 20 carbon atoms, for example 3 to 12 carbon atoms, or 3 to 6 carbon atoms.
  • heterocycloalkyl group is defined as a non-aromatic monocyclic or polycyclic group containing at least one heteroatom as a cyclic element in addition to a carbon atom. Heteroatoms may include, but are not limited to, oxygen (O), nitrogen (N), sulfur (S), selenium (Se), or phosphorus (P) atoms. Further, even if the heterocycloalkyl group does not include an aromatic ring, the bond connecting the carbon atom-carbon atom or carbon atom-heteroatom constituting the ring of the heterocycloalkyl group may include a double bond.
  • heterocycloalkyl group examples include 2-pyrrolidinyl group, 3-pyrrolidinyl group, 3-pyrrolidinyl group, piperidinyl group, 2-tetrahydrofuranyl group (2 -tetrahydrofuranyl group, 3-tetrahydrofuranyl group, 2-tetrahydrothienyl group and 3-tetrahydrothienyl group, but are not limited thereto. It is not.
  • Heterocycloalkyl groups have 2 to 20 carbon atoms, for example 3 to 19 carbon atoms, or 5 to 11 carbon atoms. That is to say that if a heteroatom is included, the heterocycloalkyl group has a ring member of 3 to 21, for example 4 to 20, or 6 to 12.
  • Bicycloalkyl group means a functional group having a structure in which at least one carbon atom selected from each of the two alkyl rings is connected to each other.
  • bicycloalkyl group examples include a bicyclopentyl group, a bicyclohexyl group, a bicycloheptyl group, a bicyclootyl group, and a bicyclononyl group Or a bicyclodecyl group.
  • the bicycloalkyl group has 5 to 20 carbon atoms, for example 7 to 18 carbon atoms, or 7 to 12 carbon atoms.
  • arylene group may mean a divalent substituent derived from the aryl group described above.
  • heteroarylene group may refer to a divalent substituent derived from the heteroaryl group described above.
  • the position of the carbon atom which may be substituted or substituted is represented as follows based on the hetero atom, and will be described below based on this.
  • the light emitting device includes a blocking layer disposed between the hole transporting layer and the light emitting layer.
  • the blocking layer may be an electron blocking layer (EBL) for preventing electrons injected from the second electrode from flowing into the hole transporting layer through the light emitting layer.
  • the blocking layer may be an exciton blocking layer that prevents excitons formed in the light emitting layer from being diffused in the direction of the first electrode to prevent non-light emission.
  • the blocking layer may be an exciton dissociation blocking layer (EDBL).
  • EDBL exciton dissociation blocking layer
  • the exciton separation blocking layer may prevent the exciton formed in the light emitting layer from being non-luminescence disappeared through an 'exciton dissociation' process at the interface between the light emitting layer and the hole transport layer.
  • the compound forming the blocking layer may be selected to have a similar level of HOMO value as the compound forming the light emitting layer.
  • the thickness of the blocking layer By adjusting the thickness of the blocking layer to the resonance length of the light emitting device, the light emitting efficiency can be increased, and the excitons can be adjusted to be formed at the center of the light emitting layer, not at the interface between the light emitting layer and another layer.
  • the compound of Formula 1 may be represented by the following formula (5).
  • X represents S, O or Si (R 1 ) (R 2 ),
  • L c1 and L c2 each independently represent a single bond -O-, -S-, an arylene group having 6 to 20 carbon atoms, a heteroarylene group having 2 to 20 carbon atoms, or a cycloalkylene group having 3 to 20 carbon atoms,
  • Z 1 and Z 2 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, or the following Chemical Formula 6 or the following Chemical Formula 7,
  • Ar a , Ar b , Ar 2, and Ar 3 each independently represent hydrogen, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 30 carbon atoms, or the following Chemical Formula 8,
  • W 1 and W 2 each independently represent N-Ar 4 , O, S or Si (R 7 ) (R 8 ),
  • R 1 , R 2 , R 7 and R 8 each independently represent an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 30 carbon atoms,
  • Ar 4 represents an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 30 carbon atoms,
  • At least one of hydrogens of Ar a , Ar b , Ar 2 , Ar 3, and Ar 4 is independently an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and at least one alkyl group having 1 to 6 carbon atoms Substituted or unsubstituted with one or more substituents selected from the group consisting of an amine group substituted with an aryl group having 6 to 30 carbon atoms.
  • the compound represented by Chemical Formula 5 may be represented by the following Chemical Formula 9.
  • L C1 and L C2 each independently represent a single bond, -O-, -S-, an arylene group having 6 to 20 carbon atoms, a heteroarylene group having 2 to 20 carbon atoms, or a cycloalkylene group having 3 to 20 carbon atoms,
  • Ar a and Ar b each independently represent hydrogen, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 30 carbon atoms, or the following Chemical Formula 8,
  • Het 1 and Het 2 represent the following Formula 10 or the following Formula 11,
  • W 2 represents N-Ar 4 , O, S or Si (R 7 ) (R 8 ),
  • Ar 4 represents hydrogen, an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 30 carbon atoms,
  • X 1 represents S or O
  • X 2 represents S
  • R 7 , R 8 , R 9 , R 10 , R 11 and R 12 each independently represent an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms,
  • l, o, p and q each independently represent an integer of 0 to 3
  • the substituent represented by Formula 11 is substituted with the compound of Formula 1 at carbon position 3 or 6.
  • Het 1 and Het 2 may affect the physical properties of the compound depending on whether the substituent represented by Formula 10 or the substituent represented by Formula 11.
  • the inventors of the present invention through repeated and various experiments, when Het 1 and Het 2 in the formula (9) is a substituent represented by the formula (10), when applied to the light emitting device, without improving the power efficiency, improving the life of the device It was confirmed that it can be made.
  • X represents S, O or Si (R 1 ) (R 2 ),
  • R 1 and R 2 each represent a methyl group or a phenyl group
  • Z 1 and Z 2 each independently represent hydrogen, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, or diphenylamine group, wherein a carbazolyl group, dibenzofuranyl group, dibenzothio
  • the phenyl group or the dibenzosilolyl group is each independently substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 30 carbon atoms,
  • Ar a and Ar b can each independently represent a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.
  • the compound of Formula 1 may be represented by the following formula (12).
  • Y represents S, O or Si (R 1 ) (R 2 ),
  • Z 1 and Z 2 are each independently hydrogen, represented by the following formula (13) or formula (14),
  • Ar a , Ar b , Ar 2, and Ar 3 each independently represent hydrogen, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 30 carbon atoms, or the following Chemical Formula 15,
  • W 1 and W 2 each independently represent N-Ar 4 , O, S or Si (R 7 ) (R 8 ),
  • R 1 , R 2 , R 7 and R 8 each independently represent an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 30 carbon atoms,
  • Ar 4 represents an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 30 carbon atoms,
  • At least one of hydrogens of Ar a , Ar b , Ar 2 , Ar 3, and Ar 4 is each independently an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and at least one alkyl group having 1 to 6 carbon atoms It is unsubstituted or substituted with one or more substituents selected from the group consisting of amine groups substituted with.
  • the compound represented by Chemical Formula 12 may be represented by the following Chemical Formula 16.
  • Y represents S, O or Si (R 1 ) (R 2 ),
  • Ar a and Ar b each independently represent an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms, or the following Chemical Formula 17,
  • W 2 represents N-Ar 4 , O, S or Si (R 7 ) (R 8 ),
  • R 1 , R 2 , R 7 and R 8 each independently represent an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 30 carbon atoms,
  • Ar 4 represents an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • Y represents S, O or Si (R 1 ) (R 2 ),
  • R 1 and R 2 each represent a methyl group or a phenyl group
  • Z 1 and Z 2 each independently represent hydrogen, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilolyl group, or diphenylamine group, wherein a carbazolyl group, dibenzofuranyl group, dibenzothio
  • the phenyl group or the dibenzosilolyl group is each independently substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 30 carbon atoms,
  • Ar a and Ar b can each independently represent a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.
  • the hole transport layer may include a compound represented by the following formula (18).
  • R 13 and R 14 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms,
  • L g each independently represents * -L 5 -L 6 -L 7 -L 8- *
  • L 5 , L 6 , L 7 and L 8 are each independently a single bond, -O-, -S-, an arylene group having 6 to 20 carbon atoms, a heteroarylene group having 2 to 20 carbon atoms, or a cycloalkyl having 3 to 20 carbon atoms. Alkylene group, except when L 5 , L 6 , L 7 and L 8 are all single bonds,
  • Ar c and Ar d each independently represent an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, or the following Chemical Formula 19,
  • W 3 represents O, S, or C (R 17 ) (R 18 ),
  • R 15 , R 16 , R 17 and R 18 each independently represent an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms,
  • r represents the integer of 0-3
  • s represents the integer of 0-4.
  • the compound represented by Formula 18 may be represented by the following Formula 20.
  • R 13 represents an aryl group having 6 to 30 carbon atoms
  • R 14 represents hydrogen
  • L g represents an arylene group having 6 to 20 carbon atoms
  • Ar c represents an aryl group having 6 to 30 carbon atoms or the following general formula (21),
  • W 3 represents O, S, or C (R 17 ) (R 18 ),
  • R 15 , R 16 , R 17 and R 18 each independently represent an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 30 carbon atoms,
  • r represents the integer of 0-2
  • s represents the integer of 0-2.
  • R 13 represents a phenyl group, biphenyl group, terphenyl group or naphthyl group,
  • R 14 represents hydrogen
  • L g represents a phenylene group, a biphenylene group, a terphenylene group or a naphthylene group
  • Ar c may represent a phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzothiophenyl group, dibenzofuranyl group, fluorenyl group, dimethylfluorenyl group or diphenylfluorenyl group.
  • the hole transport layer may include a first layer which may include a P-type dopant; And a second layer including the compound of Formula 18.
  • the emission layer may include a compound represented by the following Chemical Formula 22.
  • R 19 and R 20 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms,
  • L h and L i each independently represent * -L 9 -L 10- *
  • L 9 and L 10 each independently represent a single bond, an arylene group having 6 to 20 carbon atoms, or a heteroarylene group having 2 to 20 carbon atoms,
  • Ar e and Ar f each independently represent an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms.
  • R 19 and R 20 each independently represent hydrogen or an alkyl group having 1 to 6 carbon atoms
  • L h and L i each independently represent * -L 9 -L 10- *
  • L 9 and L 10 each independently represent a single bond, a phenylene group or a naphthylene group,
  • Ar e and Ar f may each independently represent an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms.
  • the emission layer may further include a compound represented by the following formula (23).
  • Ar g , Ar h , Ar i and Ar j are each independently an aryl group having 6 to 30 carbon atoms or a hetero having 2 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms, trimethylsilyl group or cyano group An aryl group is shown.
  • the present invention provides an electronic device including the light emitting device described above.
  • the electronic device are not particularly limited, and may be a display device or a lighting device.
  • FIG. 1 is a cross-sectional view illustrating a light emitting device according to an embodiment of the present invention.
  • the light emitting device 100 includes a first electrode 20, a hole transporting layer 30, a blocking layer 40, a light emitting layer 50, and a second electrode 60 formed on the base substrate 10. ).
  • the light emitting device 100 may be an organic light emitting diode (OLED).
  • the first electrode 20 may be formed on the base substrate 10 with a conductive material.
  • the first electrode 20 may be a transparent electrode.
  • the first electrode 20 may be formed of indium tin oxide (ITO).
  • the first electrode 20 may be an opaque (reflective) electrode.
  • the first electrode 20 may have an ITO / silver (Ag) / ITO structure.
  • the first electrode 20 may be an anode of the light emitting device 100.
  • the hole transport layer 30 is formed on the first electrode 20 and is interposed between the first electrode 20 and the blocking layer 40.
  • the hole transport layer 30 may include a hole transport layer and / or a hole injection layer.
  • the hole transport layer 30 may include a compound represented by the following formula (18).
  • the compound represented by Formula 18 may be substantially the same as described above. Therefore, overlapping detailed descriptions of each of R 13 , R 14 , L g , Ar c, and Ar d are omitted.
  • the blocking layer 40 is disposed between the hole transporting layer 30 and the light emitting layer 50, and includes an electron blocking layer (EBL), an exciton blocking layer or an exciton dissociation blocking layer, EDBL).
  • EBL electron blocking layer
  • EDBL exciton blocking layer
  • the blocking layer 40 may include a compound represented by Chemical Formula 1.
  • the compound represented by Formula 1 may be substantially the same as described above. Therefore, overlapping detailed descriptions of X, Y, L a , L b , Z 1, and Z 2 are omitted.
  • the light emitting layer 50 may be disposed between the blocking layer 40 and the second electrode 60.
  • the wavelength of the light emitted by the light emitting layer 50 may vary depending on the type of the compound forming the light emitting layer 50.
  • the material for forming the light emitting layer 50 various commercially available materials may be used without particular limitation.
  • the emission layer 50 may include a compound represented by the following Chemical Formula 22.
  • the compound represented by Chemical Formula 22 may be substantially the same as described above. Therefore, overlapping detailed descriptions of R 19 , R 20 , L h , L i , Ar e, and Ar f are omitted.
  • the second electrode 60 may be formed on the light emitting layer 50 using a conductive material.
  • the second electrode 60 may be an opaque (reflective) electrode.
  • the second electrode 60 may be an aluminum electrode.
  • the first electrode 20 is an opaque electrode
  • the second electrode 60 may be a transparent or translucent electrode, and in this case, the second electrode 60 may have a thickness of about 100 kPa to about 150 kPa. have.
  • an alloy containing magnesium and silver can be used as a material for forming the opaque electrode.
  • the second electrode 60 may be a cathode of the light emitting device 100.
  • an electron transporting layer (ETL) and / or an electron injecting layer (EIL) are formed between the light emitting layer 50 and the second electrode 60 as an electron transporting layer.
  • ETL electron transporting layer
  • EIL electron injecting layer
  • Each of the electron transporting layer and the electron injection layer may be used without any particular limitation on various commercially available materials.
  • the excitons may be singlet excitons, and may also be triplet excitons. Accordingly, the light emitting device 100 may provide light to the outside.
  • the light emitting device 100 may further include a second blocking layer (not shown) disposed between the light emitting layer 50 and the second electrode 60.
  • the second blocking layer is disposed between the light emitting layer 50 and the second electrode 60, specifically, between the light emitting layer 50 and the electron transporting layer so that holes are formed from the first electrode 20 to the light emitting layer 50. It may be a hole blocking layer (HBL) to prevent the flow into the electron transport layer via). In addition, the second blocking layer may be an exciton blocking layer that prevents excitons formed in the emission layer 50 in the direction of the second electrode 60 to prevent the excitons from extinction.
  • HBL hole blocking layer
  • the thickness of the second blocking layer is adjusted according to the resonance length of the light emitting device 100, light emission efficiency can be increased, and excitons are not the interface between the light emitting layer 50 and the other layer. 50) can be adjusted to be formed in the center portion.
  • FIG. 2 is a cross-sectional view illustrating a light emitting device according to another embodiment of the present invention.
  • the light emitting device 102 includes a first electrode 20, a hole transporting layer 32, a blocking layer 40, a light emitting layer 50, and a second electrode 60 formed on the base substrate 10. ). Except for the hole transport layer 32, the description thereof is substantially the same as that described with reference to FIG.
  • the hole transport layer 32 includes a compound represented by Formula 18 and a P-type dopant. Since the compound included in the hole transport layer 32 is substantially the same as described above, overlapping detailed description thereof will be omitted.
  • the P-type dopant may include a P-type organic dopant and / or a P-type inorganic dopant.
  • P-type organic dopant examples include compounds represented by the following Chemical Formulas 24 to 28, hexadecafluorophthalocyanine (F16CuPc), 11,11,12,12-tetracyanonaphtho-2,6-quinodimethane (11,11,12,12-tetracyanonaphtho-2,6-quinodimethane, TNAP), 3,6-difluoro-2,5,7,7,8,8-hexacyano-quinodimethane (3, 6-difluoro-2,5,7,7,8,8-hexacyano-quinodimethane, F2-HCNQ) or Tetracyanoquinodimethane (TCNQ) and the like. These may be used alone or in combination of two or more, respectively.
  • R may represent a cyano group, a sulfone group, a sulfoxide group, a sulfonamide group, a sulfonate group, a nitro group or a trifluoromethyl group.
  • m and n each independently represent an integer of 1 to 5
  • Y 1 and Y 2 may each independently represent an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms.
  • the hydrogen of the aryl group or heteroaryl group represented by Y 1 and Y 2 may be substituted or unsubstituted with an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or a hydroxyl group, and substituted or unsubstituted.
  • the hydrogens of the ring Y 1 and Y 2 may be each independently substituted or unsubstituted with a halogen group.
  • the compound represented by Chemical Formula 28 may include a compound represented by Chemical Formula 28a or Chemical Formula 28b.
  • Examples of the P-type inorganic dopant include metal oxides and metal halides. Specific examples of the P-type inorganic dopant include MoO 3 , V 2 O 5 , WO 3 , SnO 2 , ZnO, MnO 2 , CoO 2 , ReO 3 , TiO 2, FeCl 3 , SbCl 5 , MgF 2 , and the like. . These may be used alone or in combination of two or more, respectively.
  • the content of the P-type dopant may be about 0.5 parts by weight to about 20 parts by weight based on 100 parts by weight of the compound according to the present invention, which is a hole transporting compound.
  • the content of the P-type dopant may be about 0.5 parts by weight to about 15 parts by weight, or about 0.5 parts by weight to about 5 parts by weight based on 100 parts by weight of the hole transporting compound.
  • the content of the P-type dopant is about 1 part by weight to 10 parts by weight, 1 part by weight to 5 parts by weight, 1.5 parts by weight to 6 parts by weight, or 2 parts by weight to 5 parts by weight of the hole transporting compound. It may be part by weight.
  • the P-type dopant When the content of the P-type dopant is about 0.5 part by weight to about 20 parts by weight with respect to 100 parts by weight of the hole transporting compound, the P-type dopant may generate excessive leakage current without reducing the physical properties of the hole-transporting compound. You can prevent it. In addition, the energy barrier at the interface with each of the upper and lower layers in contact with the hole transport layer 32 may be reduced by the P-type dopant.
  • the light emitting device 102 may further include an electron transport layer, an electron injection layer, and / or a second blocking layer.
  • Each of the layers is substantially the same as that described in the light emitting device 100 of FIG. 1, and thus, a detailed description thereof will be omitted.
  • the light emitting device 100 shown in FIG. 1 may further include an interlayer (not shown).
  • the intermediate layer may be disposed between the first electrode 20 and the hole transport layer 30 of FIG. 1, and may be formed of a compound used as the P-type dopant described with reference to FIG. 2.
  • the light emitting device 104 includes a first electrode 20, a hole transporting layer 34, a blocking layer 40, a light emitting layer 50, and a second electrode 60 formed on the base substrate 10. ). Except for the hole transport layer 34, the description thereof is substantially the same as that described with reference to FIG.
  • the hole transport layer 34 may include a first layer 33a in contact with the first electrode 20 and a second layer 33b disposed between the first layer 33a and the blocking layer 40. Include. That is, the hole transport layer 34 may have a two-layer structure. In addition, the hole transport layer 34 may have a multilayer structure of two or more layers including the first and second layers 33a and 33b.
  • the first and second layers 33a and 33b may include the same kind of hole transport compound.
  • the components of the hole transporting compound included in the first layer 33a and the second layer 33b are reduced, thereby easily injecting holes into the light emitting layer. It can be done.
  • the same host material is used for the first layer 33a and the second layer 33b
  • the first layer 33a and the second layer 33b can be continuously formed in one chamber. There is an advantage that the manufacturing process is simplified and the production time can be shortened. Furthermore, since physical properties such as glass transition temperature between adjacent layers become similar, there is an advantage of increasing durability of the device.
  • the first layer 33a includes a compound according to the present invention represented by Chemical Formula 18 and a P-type dopant as a hole transporting compound.
  • the first layer 33a is substantially the same as the hole transport layer 32 described with reference to FIG. 2 except for the thickness. Therefore, redundant description is omitted.
  • the second layer 33b includes a compound represented by Chemical Formula 18 as a hole transporting compound, and the hole transporting compound constituting the second layer 33b includes a hole transporting compound constituting the first layer 33a; May be the same. Since the second layer 33b is also substantially the same as the hole transport layer 30 described with reference to FIG. 1 except for the thickness, detailed descriptions thereof will be omitted.
  • the first and second layers 33a and 33b may include different kinds of hole transport compounds.
  • the hole transporting compound constituting the first and second layers 33a and 33b may be a compound represented by Formula 18, and any one or more of R 13 , R 14 , L g , Ar c, and Ar d may be each independently. Can be different.
  • the compound constituting each of the first and second layers 33a and 33b may be selected to have a HOMO value for efficiently transferring holes to the emission layer 50.
  • the second layer 33b may further include a P-type dopant together with the hole transport compound.
  • the types of P-type dopants doped in the first layer 33a and the second layer 33b may be different from each other, and the doping amount may be different even if the same type is used.
  • the content P1 of the P-type dopant doped in the first layer 33a and the content P2 of the P-type dopant doped in the second layer 33b are represented by Equation 1 below. Can be satisfied.
  • P1 is the content of the doped P-type dopant relative to 100 parts by weight of the hole transporting compound in the first layer 33a
  • P2 is the amount of P doped with respect to 100 parts by weight of the hole transporting compound in the second layer 33b. The content of the type dopant.
  • the content of the P-type dopant doped in the first layer 33a is 0.3 to 20 parts by weight, 1 to 15 parts by weight, 2 to 10 parts by weight, or 4 based on 100 parts by weight of the hole transporting compound. To 6 parts by weight.
  • the content of the P-type dopant doped in the second layer 33b is 0.3 to 20 parts by weight, 0.5 to 10 parts by weight, 1 to 8 parts by weight, or 2 to 4 parts by weight based on 100 parts by weight of the hole transporting compound. It may be a minor range.
  • the light emitting device 104 may further include an electron transport layer, an electron injection layer, and / or a second blocking layer.
  • Each of the layers is substantially the same as that described in the light emitting device 100 of FIG. 1, and thus, a detailed description thereof will be omitted.
  • each of the light emitting devices 100, 102, 104 described above includes a blocking layer 40 including the compound represented by Chemical Formula 1, the light emitting devices 100, 102, 104 have excellent thermal stability. At the same time, the luminous efficiency can be improved and the life can be long.
  • the light emitting devices 100, 102, 104 are directly formed on the base substrate 10, but the first and second light emitting devices 100, 102, and 104 are respectively formed on the base substrate 10.
  • a thin film transistor may be disposed between the first electrode 20 and the base substrate 10 as a driving element for driving a pixel.
  • the first electrode 20 may be a pixel electrode connected to the thin film transistor.
  • the first electrode 20 is a pixel electrode, the first electrode 20 is disposed separately from each other in the plurality of pixels, and the base substrate 10 is disposed along an edge of the first electrode 20.
  • the barrier rib pattern may be formed so that layers stacked on the first electrode 20 disposed in adjacent pixels may be separated from each other. That is, although not shown in the drawings, the light emitting devices 100, 102, and 104 may be used in a display device that displays an image without a backlight.
  • the light emitting devices 100, 102, and 104 may be used as lighting devices.
  • the light emitting devices 100, 102, and 104 illustrated in the present invention may be used in various types of electronic devices.
  • the electronic devices may include a display device or a lighting device.
  • Tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ) (0.8 mmol, 0.9 g) was then added to the 1 L three necked round bottom flask, after which the light was blocked and refluxed for 6 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 50 mL of tetrahydrofuran (THF), poured into 500 mL of methanol, stirred for 20 minutes, and filtered to yield 13.5 g of Compound 2 as a light gray solid. Obtained (yield 80%).
  • EA ethyl acetate
  • THF tetrahydrofuran
  • Tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ) (1.6 mmol, 1.9 g) was then added to the 1 L three-necked round bottom flask, after which the light was blocked and refluxed for 6 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1000 mL of methanol, stirred for 20 minutes and filtered to give 23.4 g of a light gray solid. Obtained (yield 70%).
  • EA ethyl acetate
  • THF tetrahydrofuran
  • Tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ) (0.6 mmol, 0.7 g) was then added to the 1 L three-necked round bottom flask, after which the light was blocked and refluxed for 6 hours. I was The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 40 mL of tetrahydrofuran (THF), 400 mL of methanol, stirred for 20 minutes, and filtered to give 11.4 g of a light gray solid. Obtained (yield 85%).
  • EA ethyl acetate
  • THF tetrahydrofuran
  • Tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ) (0.8 mmol, 0.9 g) was then added to the 1 L three-necked round bottom flask, after which the light was blocked and refluxed for 7 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 30 minutes, and filtered to give 28.2 g of a light gray solid. Obtained (yield 83%).
  • EA ethyl acetate
  • THF tetrahydrofuran
  • Tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ) (0.7 mmol, 0.8 g) was then added to the 1 L three necked round bottom flask, after which the light was blocked and refluxed for 8 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 40 minutes, and filtered to give 27.8 g of a light gray solid. Obtained (yield 78%).
  • EA ethyl acetate
  • THF tetrahydrofuran
  • Tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ) (0.7 mmol, 0.8 g) was then added to the 1 L three necked round bottom flask, after which the light was blocked and refluxed for 6 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 30 minutes, and filtered to give 27.6 g of a light gray solid. Obtained (yield 80%).
  • EA ethyl acetate
  • THF tetrahydrofuran
  • Tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ) (0.8 mmol, 0.9 g) was then added to the 1 L three necked round bottom flask, after which the light was blocked and reflux for 5 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 50 mL of tetrahydrofuran (THF), poured into 500 mL of methanol, stirred for 30 minutes, and filtered to yield 13.5 g of compound 11 as a light gray solid. Obtained (yield 89%).
  • EA ethyl acetate
  • THF tetrahydrofuran
  • Tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ) (1.6 mmol, 1.9 g) was then added to the 1 L three-necked round bottom flask, after which the light was blocked and refluxed for 7 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1000 mL of methanol, stirred for 30 minutes, and filtered to give 28.7 g of a light gray solid. Obtained (yield 86%).
  • EA ethyl acetate
  • THF tetrahydrofuran
  • Tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ) (0.7 mmol, 0.8 g) was then added to the 1 L three necked round bottom flask, after which the light was blocked and reflux for 5 hours. I was. The reaction mixture was cooled, extracted with ethyl acetate (EA) and distilled water, concentrated, dissolved in 100 mL of tetrahydrofuran (THF), poured into 1 L of methanol, stirred for 30 minutes, and filtered to obtain 29.3 g of a light gray solid. Obtained (yield 85%).
  • EA ethyl acetate
  • THF tetrahydrofuran
  • Example 1 Manufacture of Light Emitting Diodes A-1 to A-13
  • a compound represented by the following Chemical Formula 29 as a host material was deposited at a rate of 1 s / sec and simultaneously a P-type dopant represented by the following Chemical Formula 30 (HAT-CN) Was co-evaporated at a ratio of about 3 parts by weight to 100 parts by weight of the host material to form a first layer having a thickness of 100 mm 3.
  • the compound represented by Chemical Formula 29 was deposited on the first layer to a thickness of 300 ⁇ to form a second layer.
  • a compound according to Preparation Example 1 was deposited on the second layer to a thickness of 100 ⁇ s to form a barrier layer.
  • the compound represented by Chemical Formula 31 and the compound represented by Chemical Formula 32 were co-deposited on the blocking layer at a weight ratio of 100: 5 to form a light emitting layer having a thickness of about 200 ⁇ s.
  • the compound represented by the following Chemical Formula 33 and the compound represented by the following Chemical Formula 34 were co-deposited at a 50:50 weight ratio to form an electron transport layer having a thickness of about 360 kPa on the light emitting layer. Subsequently, an electron injection layer having a thickness of about 5 ⁇ s was formed on the electron transport layer by using the compound represented by the following Chemical Formula 34.
  • the light emitting device A-1 including the compound according to Preparation Example 1 of the present invention was prepared.
  • the light emitting devices A-2 to A light emitting device A are substantially the same as those of manufacturing the light emitting device A-1. -13 was prepared.
  • the compound represented by the formula (35) as a host material was deposited at a rate of 1 s / sec and simultaneously the P-type dopant (HAT-CN) represented by the formula (30) was Co-evaporation was performed at a rate of about 3 parts by weight relative to 100 parts by weight of the host material to form a 100 mm thick first layer.
  • a compound represented by Chemical Formula 35 was deposited on the first layer at a thickness of 300 kPa to form a second layer.
  • a compound according to Preparation Example 1 was deposited on the second layer to a thickness of 100 ⁇ s to form a barrier layer.
  • the compound represented by Formula 36 and the compound represented by Formula 32 were co-deposited at a weight ratio of 100: 5 on the blocking layer to form a light emitting layer having a thickness of about 200 ⁇ s.
  • the compound represented by Chemical Formula 33 and the compound represented by Chemical Formula 34 were co-deposited on a light emitting layer in a 50:50 weight ratio to form an electron transport layer having a thickness of about 360 Pa. Subsequently, an electron injection layer having a thickness of about 5 ⁇ s was formed on the electron transport layer by using the compound represented by Chemical Formula 34.
  • the light emitting device B-1 including the compound according to Preparation Example 1 of the present invention was prepared.
  • the light emitting devices B-2 to B are substantially the same as those of manufacturing the light emitting device B-1. -13 was prepared.
  • a compound represented by Formula 37 as a host material was deposited at a rate of 1 s / sec and simultaneously a P-type dopant (HAT-CN) represented by Formula 30 was Co-evaporation was performed at a rate of about 3 parts by weight relative to 100 parts by weight of the host material to form a 100 mm thick first layer.
  • the compound represented by Formula 37 was deposited on the first layer to a thickness of 300 kPa to form a second layer.
  • a compound according to Preparation Example 1 was deposited on the second layer to a thickness of 100 ⁇ s to form a barrier layer.
  • a compound represented by Formula 38 and a compound represented by Formula 32 were co-deposited on the blocking layer in a weight ratio of 100: 5 to form a light emitting layer having a thickness of about 200 ⁇ s.
  • the compound represented by Chemical Formula 33 and the compound represented by Chemical Formula 34 were co-deposited on a light emitting layer in a 50:50 weight ratio to form an electron transport layer having a thickness of about 360 Pa. Subsequently, an electron injection layer having a thickness of about 5 ⁇ s was formed on the electron transport layer by using the compound represented by Chemical Formula 34.
  • the light emitting device C-1 including the compound according to Preparation Example 1 of the present invention was prepared.
  • the light emitting devices C-2 to the light emitting devices C are substantially the same as those of manufacturing the light emitting device C-1. -13 was prepared.
  • Comparative Element 1 was manufactured in the same manner as in Example 1, except that no separate blocking layer was formed.
  • Comparative Device 2 was manufactured in the same manner as in Example 2, except that no separate blocking layer was formed.
  • Comparative element 3 was manufactured in the same manner as in Example 3, except that no separate blocking layer was formed.
  • Comparative Device 4 was manufactured in the same manner as in Example 1, except that a blocking layer was formed using the compound represented by Chemical Formula 39.
  • Comparative element 5 was manufactured in the same manner as in Example 2, except that a blocking layer was formed using the compound represented by Chemical Formula 39.
  • Comparative element 6 was manufactured in the same manner as in Example 3, except that a blocking layer was formed using the compound represented by Chemical Formula 39.
  • the light emitting devices A-1 to A-13 and the comparative devices 1 and 4, respectively, were dispensed with a UV curing sealant at the edge of the cover glass with a moisture absorbent (Getter) in a glove box in a nitrogen atmosphere. Each of them and the cover glass were bonded together and cured by irradiation with UV light.
  • power efficiency was measured based on the value when the luminance was 1,000 cd / m 2 .
  • the unit of the result of measuring the power efficiency is lm / W.
  • T 50 means a time taken for the luminance of the light emitting element to be 50% of the initial luminance when the initial luminance of the light emitting element is 5,000 cd / m 2 .
  • the value for lifetime can be converted to the expected lifetime when measured under different measurement conditions on the basis of conversion equations known to those skilled in the art.
  • the power efficiency of the light emitting devices A-1 to A-13 including the blocking layer formed of each of the compounds according to Preparation Examples 1 to 13 of the present invention is 5.6 lm / W or more, and the average power efficiency is about. It can be seen that it is 6.6 lm / W. It can be seen that the power efficiency of the light emitting elements A-1 to A-13 according to the present invention is significantly increased when the power efficiency of Comparative Element 1 is 4.3 lm / W and that of Comparative Device 4 is 5.1 lm / W. have. For example, it can be seen that the power efficiency of the light emitting device A-8 is increased by about 50% or more compared with the comparative device 4.
  • the lifetimes of the light emitting elements A-1 to A-13 were 178 hours or more, and the average element life thereof was about 233 hours, whereas the lifetimes of the comparative elements 1 and 4 were 128 hours and 155 hours, respectively. Accordingly, it can be seen that the lifetimes of the light emitting A-1 to A-13 according to the present invention are significantly longer than those of the comparative elements 1 and 4. For example, it can be seen that the lifetime of the light emitting device A-8 is about 75% or more longer than that of the comparative device 4.
  • the physical properties of the light emitting device are affected by the bonding position of the substituents constituting the compound applied to the light emitting device. For example, comparing the structures of the compounds (Compounds 2 and 11) used in Light-Emitting Element A-2 and Light-Emitting Element A-11, except that the bonding positions of the substituents substituted at both ends of each compound are different. It can be seen that is the same structure. Comparing the physical properties of the light emitting device A-2 and the light emitting device A-11, the power efficiency is shown at an equivalent level. However, in terms of lifespan, it can be seen that the light emitting device A-11 is improved by about 1.6%.
  • the light emitting elements A-1 to A-13 are substantially the same as those of the comparative elements 1 and 4. It can be seen that emits light having the same blue color.
  • the light emitting elements A-1 to A-13 according to the present invention have almost no change in color coordinates while improving the power efficiency of the blue light emitting elements and increasing their lifetime.
  • the light emitting devices B-1 to B-13 and the comparative devices 2 and 5, respectively, were dispensed with a UV curing sealant at the edge of the cover glass with a moisture absorbent (Getter) in a glove box in a nitrogen atmosphere. Each of them and the cover glass were bonded together and cured by irradiation with UV light.
  • Power efficiency was measured based on the value when the luminance was 1,000 cd / m 2 .
  • the unit of the result of measuring the power efficiency is lm / W.
  • T 50 means a time taken for the luminance of the light emitting element to be 50% of the initial luminance when the initial luminance of the light emitting element is 5,000 cd / m 2 .
  • the value for lifetime can be converted to the expected lifetime when measured under different measurement conditions on the basis of conversion equations known to those skilled in the art.
  • the power efficiency of the light emitting devices B-1 to B-13 including the blocking layer formed of each of the compounds according to Preparation Examples 1 to 13 of the present invention is 6.1 lm / W or more, and the average power efficiency is about. You can see that it is 7.3 lm / W. It can be seen that the power efficiency of the light emitting elements B-1 to B-13 according to the present invention is significantly increased when the power efficiency of the comparative element 2 is 4.9 lm / W and the power efficiency of the comparative element 5 is 5.9 lm / W. have. For example, it can be seen that the power efficiency of the light emitting device B-8 is increased by about 40% or more compared with the comparative device 5.
  • the lifetimes of the light emitting elements B-1 to B-13 were 199 hours or more, and the average element life thereof was about 261 hours, whereas the lifetimes of the comparative elements 2 and 5 were 152 hours and 189 hours, respectively. Therefore, it can be seen that the lifetimes of the light emitting B-1 to B-13 according to the present invention are significantly longer than those of the comparative elements 2 and 5. For example, it can be seen that the lifespan of the light emitting device B-8 is about 73% longer than that of the comparative device 4.
  • the physical properties of the light emitting device are affected by the bonding position of the substituents constituting the compound applied to the light emitting device. Comparing the physical properties of the light emitting device B-2 and the light emitting device B-11, the power efficiency appears at a similar level. However, in terms of lifespan, it can be seen that the light emitting device B-11 is improved by about 1.5%. Similarly, when the light emitting element B-3 and the light emitting element B-12 are compared, the lifespan of the light emitting element B-12 is improved by about 4.3. In addition, when comparing the light emitting device B-10 and the light emitting device B-13, it can be seen that the life of the light emitting device B-13 is improved by about 2.2%.
  • the light emitting elements B-1 to B-13 are substantially the same as those of the comparison elements 2 and 5, respectively. It can be seen that emits light having the same blue color.
  • the light emitting elements B-1 to B-13 according to the present invention have almost no change in color coordinates while improving the power efficiency of the blue light emitting elements and increasing their lifetime.
  • the light emitting devices C-1 to C-13 and the comparative devices 3 and 6, respectively, were dispensed with a UV curing sealant at the edge of the cover glass with a moisture absorbent (Getter) in a glove box in a nitrogen atmosphere. Each of them and the cover glass were bonded together and cured by irradiation with UV light.
  • power efficiency was measured based on the value when the luminance was 1,000 cd / m 2 .
  • the unit of the result of measuring the power efficiency is lm / W.
  • T 50 means a time taken for the luminance of the light emitting element to be 50% of the initial luminance when the initial luminance of the light emitting element is 5,000 cd / m 2 .
  • the value for lifetime can be converted to the expected lifetime when measured under different measurement conditions on the basis of conversion equations known to those skilled in the art.
  • the power efficiency of the light emitting devices C-1 to C-13 including the blocking layer formed of each of the compounds according to Preparation Examples 1 to 13 of the present invention is 5.3 lm / W or more, the average power efficiency is about You can see that it is 6.4 lm / W. It can be seen that the power efficiency of the light emitting devices C-1 to C-13 according to the present invention is significantly increased when the power efficiency of the comparative device 3 is 3.5 lm / W and the power efficiency of the comparative device 6 is 4.3 lm / W. have. For example, it can be seen that the power efficiency of the light emitting device C-8 is increased by about 74% or more compared with the comparative device 6.
  • the lifetimes of the light emitting elements C-1 to C-13 were 161 hours or more, and the average element life thereof was about 188 hours, whereas the lifetimes of the comparative elements 3 and 6 were 113 hours and 131 hours, respectively. Therefore, it can be seen that the lifetimes of the light emitting C-1 to C-13 according to the present invention are significantly longer than those of the comparative elements 3 and 6. For example, it can be seen that the lifetime of the light emitting device C-8 is about 63% or more longer than that of the comparative device 6.
  • the physical properties of the light emitting device are affected by the bonding position of the substituents constituting the compound applied to the light emitting device.
  • the power efficiency is shown to be equal.
  • lifespan it can be seen that the light emitting device C-11 is improved by about 1.1%.
  • the life of the light emitting device C-13 is improved by about 1%.
  • the light emitting elements C-1 to C-13 are substantially the same as those of the comparative elements 3 and 6. It can be seen that emits light having the same blue color.
  • the light emitting elements C-1 to C-13 according to the present invention have almost no change in color coordinates while improving the power efficiency of the blue light emitting elements and increasing their lifetime.

Abstract

L'invention concerne une diode électroluminescente, qui comprend : une première électrode ; une seconde électrode ; une couche électroluminescente agencée entre les première et seconde électrodes ; une couche de transport à trous, agencée entre la première électrode et la couche électroluminescente ; et une couche de blindage, agencée entre la couche de transport à trous et la couche électroluminescente et qui comprend un composé nouveau.
PCT/KR2013/008466 2012-09-21 2013-09-18 Diode électroluminescente dotée d'une nouvelle structure et appareil électronique la contenant WO2014046495A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US14/429,948 US9614163B2 (en) 2012-09-21 2013-09-18 Light-emitting diode having novel structure and electronic apparatus comprising same

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KR10-2012-0105153 2012-09-21
KR20120105153 2012-09-21
KR10-2013-0103512 2013-08-29
KR1020130103512A KR101400301B1 (ko) 2012-09-21 2013-08-29 신규 구조의 발광 소자 및 이를 포함하는 전자 장치

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9559311B2 (en) 2013-02-22 2017-01-31 Idemitsu Kosan Co., Ltd. Anthracene derivative, organic-electroluminescence-device material, organic electroluminescence device, and electronic equipment
CN108666430A (zh) * 2017-06-23 2018-10-16 深圳市晶鸿电子有限公司 一种高性能有机电致发光器件

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110104452A (ko) * 2010-03-16 2011-09-22 꼼미사리아 아 레네르지 아또미끄 에 오 에네르지 알떼르나띠브스 고효율 하이브리드 발광 다이오드
KR20110137712A (ko) * 2010-06-17 2011-12-23 이-레이 옵토일렉트로닉스 테크놀로지 컴퍼니 리미티드 유기전계발광장치용 화합물 및 이를 포함하는 유기전계발광장치
KR20120052936A (ko) * 2009-06-18 2012-05-24 바스프 에스이 전계 발광 소자를 위한 정공 수송 물질로서의 페난트로아졸 화합물
KR20120095997A (ko) * 2009-11-18 2012-08-29 메르크 파텐트 게엠베하 Ｏｌｅｄ 용 질소-함유 축합 헤테로시클릭 화합물

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120052936A (ko) * 2009-06-18 2012-05-24 바스프 에스이 전계 발광 소자를 위한 정공 수송 물질로서의 페난트로아졸 화합물
KR20120095997A (ko) * 2009-11-18 2012-08-29 메르크 파텐트 게엠베하 Ｏｌｅｄ 용 질소-함유 축합 헤테로시클릭 화합물
KR20110104452A (ko) * 2010-03-16 2011-09-22 꼼미사리아 아 레네르지 아또미끄 에 오 에네르지 알떼르나띠브스 고효율 하이브리드 발광 다이오드
KR20110137712A (ko) * 2010-06-17 2011-12-23 이-레이 옵토일렉트로닉스 테크놀로지 컴퍼니 리미티드 유기전계발광장치용 화합물 및 이를 포함하는 유기전계발광장치

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9559311B2 (en) 2013-02-22 2017-01-31 Idemitsu Kosan Co., Ltd. Anthracene derivative, organic-electroluminescence-device material, organic electroluminescence device, and electronic equipment
CN108666430A (zh) * 2017-06-23 2018-10-16 深圳市晶鸿电子有限公司 一种高性能有机电致发光器件

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