WO2017099326A1 - Composé pour dispositif optoélectronique organique, dispositif optoélectronique organique et appareil d'affichage - Google Patents

Composé pour dispositif optoélectronique organique, dispositif optoélectronique organique et appareil d'affichage Download PDF

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WO2017099326A1
WO2017099326A1 PCT/KR2016/008569 KR2016008569W WO2017099326A1 WO 2017099326 A1 WO2017099326 A1 WO 2017099326A1 KR 2016008569 W KR2016008569 W KR 2016008569W WO 2017099326 A1 WO2017099326 A1 WO 2017099326A1
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group
substituted
unsubstituted
compound
organic optoelectronic
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Korean (ko)
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한수진
강동민
이한일
류동완
민수현
신창주
유은선
정성현
정호국
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삼성에스디아이 주식회사
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D498/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • H10K85/649—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
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • a compound for organic optoelectronic devices an organic optoelectronic device, and a display device.
  • Organic optoelectronic devices are devices that can switch electrical energy and light energy.
  • Organic optoelectronic devices can be divided into two types according to the principle of operation.
  • One is an optoelectronic device in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to the other electrodes, respectively, to generate electrical energy.
  • It is a light emitting device that generates light energy from energy.
  • Examples of the organic optoelectronic device may be an organic photoelectric device, an organic light emitting device, an organic solar cell and an organic photo conductor drum.
  • organic light emitting diodes have attracted much attention recently as demand for flat panel displays increases.
  • the organic light emitting device converts electrical energy into light by applying an electric current to the organic light emitting material, and has a structure in which an organic layer is inserted between an anode and a cathode.
  • the organic layer may include a light emitting layer and an auxiliary layer
  • the auxiliary layer may include, for example, a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, and an electron injection layer to increase efficiency and stability of the organic light emitting device. And at least one layer selected from a hole blocking layer.
  • the performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and in particular, by the organic materials included in the organic layer.
  • a compound for an organic optoelectronic device represented by the following formula (I) is provided.
  • X is 0 or S
  • R 1 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted C6 to C30 arylamine group, or a combination thereof,
  • R 2 to R 5 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to
  • L is a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
  • substituted means that at least one hydrogen is deuterium, a halogen group, a hydroxyl group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocyclo Alkyl group, C6 to C30 aryl group, C2 to C30 heterocyclic group, C1 to C20 alkoxy group, C1 to C10 trifluoroalkyl group or Mean substituted by cyano group.
  • an organic optoelectronic device includes an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, the organic layer including the compound for an organic optoelectronic device described above. do.
  • a display device including the organic optoelectronic device is provided.
  • FIG. 1 and 2 are cross-sectional views illustrating organic light emitting diodes according to example embodiments.
  • substituted means that at least one hydrogen is deuterium, a halogen group, a hydroxyl group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 It means substituted with a heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group or a cyano group.
  • the substituted C6 to C30 aryl group can be fused to another adjacent substituted C6 to C30 aryl group to form a substituted or unsubstituted fluorene ring.
  • hetero means one to three hetero atoms selected from the group consisting of ⁇ , ⁇ , S, P, and Si in one functional group, unless otherwise defined, and the remainder is carbon. do.
  • an "alkyl group” is aliphatic.
  • the alkyl group may be a "saturated alkyl group" that does not contain any double bonds or triple bonds.
  • the alkyl group may be an alkyl group of C1 to C30. More specifically, the alkyl group
  • a C1 to C4 alkyl group means that the alkyl chain contains 1 to 4 carbon atoms, and methyl, ethyl, propyl, iso-propyl, ⁇ -butyl, iso-butyl, sec-butyl and t-butyl Selected from the group consisting of:
  • alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, nucleosil group, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclonucleus It means a practical skill.
  • aryl (aryl) group refers to a group of groups having at least one hydrocarbon aromatic moiety, wherein all of the elements of the hydrocarbon aromatic moiety have a P-orbital, and these P-orbitals are conjugated (conjugation). ), Including a phenyl group, a naphthyl group, and the like, and two or more hydrocarbon aromatic moieties connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quarterphenyl group, and the like.
  • Non-aromatic fused rings in which the tees are fused directly or indirectly may be included, for example, a fluorenyl group and the like.
  • Aryl groups are monocyclic, polycyclic or fused ring polycyclic (i.e.
  • Ring groups that divide adjacent pairs of carbon atoms.
  • the aryl group means a phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, chrysenyl group and the like.
  • heterocyclic group is a higher concept including a heteroaryl group, such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. It means containing at least one hetero atom selected from the group consisting of N, 0, S, P and Si in place of carbon (C). In the case where the heterocyclic group is a fused ring, the heterocyclic group may include one or more heteroatoms for all or each ring.
  • a "heteroaryl group” refers to N, O, S, P and instead of carbon (C) in the aryl group.
  • heteroaryl group It means to contain at least one hetero atom selected from the group consisting of Si.
  • Two or more heteroaryl groups may be directly connected through a sigma bond, or when the C2 to C60 heteroaryl group includes two or more rings, two or more rings may be fused to each other.
  • the heteroaryl group is a fused ring, each ring may contain 1 to 3 heteroatoms.
  • a substituted or unsubstituted C6 to C30 aryl group and / or a substituted or unsubstituted C2 to C30 heterocyclic group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra Senyl, substituted or unsubstituted
  • Phenanthryl group substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted P-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted Or an unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perrylenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group , Substituted or unsubstituted pyryl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted imidazolyl group, substituted or un
  • Acridinyl group substituted or unsubstituted phenazineyl group, substituted or unsubstituted phenothiazineyl group, substituted or unsubstituted phenoxazineyl group, substituted or unsubstituted fluorenyl group, substituted or Unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted carbazole group, substituted or unsubstituted benzothiophenpyrimidinyl group, substituted or unsubstituted benzothiophenpyridyl group, substituted Or an unsubstituted benzofuran pyrimidinyl group, a substituted or unsubstituted benzofuran pyridyl group, a substituted or unsubstituted benzofuran pyrrolyl group, a substituted or unsubstituted benzothiophenpyri
  • a single bond means carbon or a bond directly connected to each other via a hetero atom other than carbon, and specifically, L means a single bond that a substituent connected to L is directly connected to a central core. it means. That is, in the present specification, a single bond does not mean methylene or the like via carbon.
  • the hole characteristic refers to a characteristic capable of forming holes by donating electrons when an electric field is applied, and injecting holes formed at the anode into the light emitting layer having conductive properties along the HOMO level, and emitting layer. It refers to a property that facilitates the movement of the hole formed in the anode and movement in the light emitting layer.
  • the electron characteristic refers to a characteristic in which electrons can be received when an electric field is applied, and has conductivity characteristics along the LUMO level, injecting electrons formed at the cathode into the light emitting layer, moving electrons formed in the light emitting layer to the cathode, and It means a property that facilitates movement.
  • the compound for an organic optoelectronic device is represented by the following formula (I). [Formula I]
  • X is 0 or S
  • R 1 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to
  • R 2 to R 5 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted A C2 to C30 heterocyclic group, a substituted or unsubstituted C6 to C30 arylamine group, or a combination thereof,
  • L is a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
  • substituted means that at least one hydrogen is deuterium, halogen, C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C3 to C30 cycloalkyl group, C2 to C30 heterocycloalkyl group, C6 to C30 It means an aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group or a cyano group.
  • indolophenoxazine indolo phenoxazine
  • indolophenothiazine indolophenothiazine
  • the substituent R 1 is a C6 to C30 aryl group unsubstituted or substituted
  • C30 aryl group C6 to C30 arylamine group unsubstituted or substituted with C6 to C30 aryl group; A C2 to C30 heterocyclic group unsubstituted or substituted with a C6 to C30 aryl group or a C2 to C30 heterocyclic group; Or N-containing C2 to C30 except for a carbazolyl group
  • It may be a C6 to C30 aryl group substituted with a heterocyclic group.
  • a core having an additional ring extended from (indolophenothiazine) has excellent light emitting ability and electron transporting ability or hole transporting ability of the core itself, but due to the plate-like structure, fairness may be reduced during the deposition process.
  • fairness can be improved by including a C6 to C30 aryl group substituted or unsubstituted with a C6 to C30 aryl group in R 1 as a substituent to modify the plate structure.
  • the core has excellent hole accepting ability, while the hole transporting ability is
  • a C6 to C30 arylamine group which is unsubstituted or substituted with an aryl group, may be included as a substituent to have a hole transporting capacity of about a layered layer for use in the hole transport layer.
  • the C2 to C30 heterocyclic groups having electronic properties in R 1 By substituting the C2 to C30 heterocyclic groups having electronic properties in R 1 , a device suitable for use in a HOST defect or an electron transport layer having bipolar properties can be produced. More specifically, the C6 to C30 aryl group or C2 to C30 The C2 to C30 heterocyclic group unsubstituted or substituted with a heterocyclic group includes a C2 to C30 heterocyclic group having hole characteristics, and a C2 to C30 heterocyclic group having electronic characteristics,
  • the C2 to C30 heterocyclic group having the above hole characteristics is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted group
  • the C2 to C30 heterocyclic group having the above electronic properties may be an N-containing C2 to C30 heterocyclic group except for a carbazolyl group or an N-containing C2 to C30 heterocyclic group except for a carbazolyl group unsubstituted or substituted with a C6 to C30 aryl group. .
  • N-containing C2 to C30 heterocyclic group except for the carbazolyl group is, for example, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinazoli Nyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or Unsubstituted isoindolyl group, substituted or unsubstituted benzothiophenpyrimidinyl group, substituted or unsubstituted benzothiophenpyridyl group, substituted or unsubstitute
  • the C2 to C30 heterocyclic group is a pyridyl group, pyrimidyl group, triazinyl group, benzoimidazole group, benzopyrimidyl group, benzopyridyl group, carbazolyl group, dibenzofuranyl group, dibenzoti Offenyl, fluorenyl, benzothiopyrimidinyl,
  • It may be selected from benzofuran pyrimidinyl group, benzothiopyridyl group or benzofuran pyridyl group.
  • the C6 to C30 aryl group unsubstituted or substituted with the C6 to C30 aryl group may be, for example, a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a fluorenyl group, and the like, but is not limited thereto.
  • the C6 to C30 arylamine group unsubstituted or substituted with the C6 to C30 aryl group may be, for example, a diphenylamine group, a dibiphenylamine group, a phenylbiphenylamine group, a phenylnaphthylamine group, a dinaphthylamine group, or the like. It is not limited to this.
  • Dipyridinylphenyl group dipyrimidinylphenyl group, ditriazinylphenyl group, dipyridinylbiphenyl group, dipyrimidanylbiphenyl group, ditriazinylbiphenyl group, quinolinylphenyl group,
  • It may be an isoquinolinylphenyl group, a quinolinylbiphenyl group, an isoquinolinylbiphenyl group, etc., but is not limited thereto.
  • R 1 may be selected from the groups listed in the following Groups 1 to 4, but is not limited thereto.
  • L is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted quarterphenylene group, It may be a substituted or unsubstituted naphthylene group, or a combination thereof.
  • the compound for an organic optoelectronic device may be selected from, for example, the compounds listed in Groups A to D, but is not limited thereto.
  • the organic optoelectronic device is not particularly limited as long as the device can switch electrical energy and light energy. Examples thereof include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photosensitive drum.
  • the organic optoelectronic device may include an anode and a cathode facing each other, at least one organic layer positioned between the anode and the cathode, and the organic layer may include the compound for an organic optoelectronic device described above.
  • an organic light emitting diode 100 includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 positioned between the anode 120 and the cathode 1 10. It includes.
  • the anode 120 may be made of a high work function conductor, for example, to facilitate hole injection, and may be made of metal, metal oxide and / or conductive polymer, for example.
  • the anode 120 is, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold or an alloy thereof; Zinc oxide, indium oxide, indium tin oxide (ITO),
  • Metal oxides such as indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO and A1 or Sn0 2 and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene) (polyehtylenedioxythiophene: PEDT), polypyrrole and polyaniline, and the like. It is not limited.
  • a cathode (110) is, for example, and an electron injection can be a work function of ⁇ made low conductive body so as to facilitate, for example, it may be made of a metal, metal oxide and / or conductive polymers.
  • the negative electrode 1 10 is, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; Multilayer structure materials such as LiF / Al, Li0 2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, but are not limited thereto.
  • the organic dance 105 includes a light emitting layer 130 including the compound for an organic optoelectronic device described above.
  • the light emitting layer 130 may include, for example, the compound for an organic optoelectronic device alone, may include at least two kinds of the compound for the organic optoelectronic device described above, or may include the composition for the organic optoelectronic device described above. .
  • the compound for an organic optoelectronic device according to an embodiment of the present invention may be included, for example, as a host of the light emitting layer, and most specifically, may be included as a red host.
  • the organic light emitting diode 200 further includes a hole auxiliary layer 140 in addition to the light emitting layer 130.
  • the hole auxiliary layer 140 may further increase hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.
  • the hole auxiliary layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer.
  • the compound for an organic optoelectronic device described above may be included in the emission layer 130.
  • the organic light emitting device may further include an electron transport layer, an electron injection layer, a hole injection layer, and the like as the organic layer 105 in FIG. 1 or 2.
  • the organic light emitting diodes 100 and 200 form an anode or a cathode on a substrate, and then form an organic layer by a dry film method such as evaporation, sputtering, plasma plating, and ion plating, and then thereon. It can be prepared by forming a cathode or an anode.
  • the organic light emitting diode described above may be applied to an organic light emitting diode display.
  • Tris (diphenylideneacetone) dipalladium (o) (lg, 1.09 mmol), tris-tert butylphosphine (0.2 g, 1.09 mmol) and sodium tert-butoxide (0. 2 g, 2 mmol) were added sequentially and 18 hours at 100 ° C. Heated to reflux. After the reaction was completed, add water to the reaction solution
  • intermediate 1-9 (20 g, 52 mmol) was dissolved in 1 L of dimethylformamide (DMF), followed by bis (pinacolato) diboron (16 g, 62.5 mmol) and ( ⁇ , ⁇ - bis (diphenylphosphine) ferrocene).
  • DMF dimethylformamide
  • II dichloropalladium
  • potassium ⁇ 13 130 1 ⁇ 101 was added and heated to reflux for 5 hours at 150 ° C.
  • water was added to the reaction solution, and the mixture was filtered and dried in a vacuum oven.
  • the obtained residue was separated and purified through flash column chromatography, obtaining an intermediate 1-10 (19 g, 85%).
  • aniline (30 g, 536 mmol) was dissolved in 1 L of tetrahydrofiiran (THF), followed by 4-bromo-1, 1'-biphenyl (125 g, 536 mmol).
  • intermediate 1-20 35 g, 145 mmol was dissolved in 1 L of THF, followed by 3-Chlorophenylboronic acid (24 g, 159 mmol) and tetrakis (triphenylphosphine) palladium (1.6 g, 1.4 mmol) was added and stirred.
  • Potassium carbonate saturated in water 50 g, 362 mmol i: was added thereto and heated to reflux for 12 hours at 80 ° C. After completion of reaction, water was added to the reaction solution, extracted with dichloromethane (DCM), and water was removed with anhydrous MgS0 4 . The resulting residue was separated and purified through flash column chromatography, obtaining a compound 1-21 (106 g, 88%).
  • Intermediate 1-1 1 (10 g, 21.6 mmol) and tris (diphenylideneacetone) dipalladium (o) (0.13) g, 0.14 mmol) tris-tert butylphosphine (0.12 g, 0.58 mmol) and sodium tert-butoxide (1.6 g, 17.28 mmol) were sequentially added and heated to reflux for 18 hours at 100 ° C.
  • intermediate 1-5 (5 g, 14.4 mmol) was dissolved in 1 L of tetrahydrofuran (THF), followed by 3-bromo-9-phenyI-9H-carbazole (7 g, 2L6 imnol).
  • intermediate 1-5 (5 g, 14.4 mmol) was dissolved in 1 L of tetra ydrofuran (THF), followed by intermediate 1-20 (7 g, 21.6 mmol).
  • the anode is cut into a size of 50mm X 50 mm X 0.7 mm ⁇ glass substrate with a sheet resistance value of 15 ⁇ / ⁇ in each of acetone, isopropyl alcohol and pure water for 15 minutes
  • UV ozone washing was used for 30 minutes.
  • N-pheny lamino] biphenyl [DNTPD] was vacuum deposited to form a hole injection layer having a thickness of 600 A. Then the same vacuum
  • a hole transport layer having a thickness of 300A was formed by vacuum deposition of HT-1.
  • a light emitting layer having a thickness of 300 A was formed using compound A-3 obtained in Synthesis Example 22 under the same vacuum deposition conditions.
  • phosphate dopant acetylacetonatobis (2-phenylquinolinato) iridium (Ir (pq) 2acac) was formed. Deposition at the same time. At this time, by adjusting the deposition rate of the phosphorescent dopant, it was deposited in the amount of the phosphorescent dopyeon agent so that 7 percent by weight when the total amount of the light-emitting layer to 100 parts by weight 0/0.
  • Bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminum (BAlq) was deposited to have a film thickness of 50 A.
  • a hole blocking layer was formed.
  • Tris (8-hydroxyquinolinato) aluminum (Alq3)- was deposited under the same vacuum deposition conditions to form an electron transport layer having a thickness of 250 A.
  • An organic photoelectric device was manufactured by sequentially depositing LiF and A1 as a cathode on the electron transport layer.
  • the structure of the organic photoelectric device is ITO / DNTPD (60 nm) / HT-l (30 nm) / EML ( compound A-3 (93 parts by weight 0 /.) + Ir (pq ) 2 acac (7 parts by weight 0/0) , 30 nm) / Balq (5 nm) / Alq 3 (25 nm) / LiF (1 nm) I Al (100 nm).
  • Comparative Example 1 An organic light emitting diode was manufactured according to the same method as Example 1 except for using 4,4′-di (9H-carbazol-9-yl) biphenyl (CBP) instead of Compound A-3 of Synthesis Example 22.
  • CBP 4,4′-di (9H-carbazol-9-yl) biphenyl
  • the structures of DNTPD, BAlq, HT-1, CBP, and Ir (pq) 2 acac used in the organic light emitting device are as follows.
  • the current value flowing through the unit device was measured by using a current-voltmeter (Keithley 2400) while increasing the voltage from 0V to 10V, and the measured current value was divided by the area to obtain a result.
  • the resulting organic light emitting device was measured using a luminance meter (Minolta Cs-1000 A) while increasing the voltage from 0V to 10V to obtain a result.
  • the current efficiency (cd / A) of the same current density (10 mA / cm 2 ) was calculated using the luminance, current density and voltage measured from (1) and (2). (4) life measurement
  • the initial luminance (cd / m 2 ) was emitted at 3000 cd / m 2 , and the decrease in luminance over time was measured to obtain a result by measuring the time of decreasing to 90% of the initial luminance.
  • the organic light emitting device according to Examples 1 to 6 is significantly improved light emission efficiency and life characteristics compared to the organic light emitting device according to Comparative Example 1.
  • the present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains has another specific form without changing the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.

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Abstract

L'invention concerne un composé pour dispositif optoélectronique organique, représenté par la formule chimique I; un dispositif optoélectronique organique sur lequel le composé est appliqué; et un appareil d'affichage comprenant le dispositif optoélectronique organique. [Formule chimique I] (Dans la formule chimique I, X représente O ou S).
PCT/KR2016/008569 2015-12-08 2016-08-03 Composé pour dispositif optoélectronique organique, dispositif optoélectronique organique et appareil d'affichage WO2017099326A1 (fr)

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