WO2017043770A1 - Composés électroluminescents organiques et dispositif électroluminescent organique les comprenant - Google Patents

Composés électroluminescents organiques et dispositif électroluminescent organique les comprenant Download PDF

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WO2017043770A1
WO2017043770A1 PCT/KR2016/008476 KR2016008476W WO2017043770A1 WO 2017043770 A1 WO2017043770 A1 WO 2017043770A1 KR 2016008476 W KR2016008476 W KR 2016008476W WO 2017043770 A1 WO2017043770 A1 WO 2017043770A1
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substituted
unsubstituted
organic electroluminescent
alkyl
membered
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PCT/KR2016/008476
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Doo-Hyeon Moon
Jae-Hoon Shim
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020160089063A external-priority patent/KR20170031019A/ko
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to US15/747,893 priority Critical patent/US20180223184A1/en
Priority to CN201680049101.5A priority patent/CN107922424A/zh
Publication of WO2017043770A1 publication Critical patent/WO2017043770A1/fr

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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
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    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
  • An electroluminescent (EL) device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
  • An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as materials to form a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • the organic EL device(OLED) converts electric energy into light when electricity is applied to an organic light-emitting material(s).
  • the organic EL device has a structure comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode.
  • the organic layer of the organic EL device comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (comprising a host material and a dopant material), an electron buffering layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.
  • materials for forming the organic layer can be classified as a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron buffering material, a hole blocking material, an electron transport material, an electron injection material, etc.
  • a voltage is applied to the organic EL device, holes and electrons are injected from an anode and a cathode, respectively, to the light-emitting layer.
  • Excitons having high energy are formed by recombinations between the holes and the electrons, the energy puts the organic light-emitting compound in an excited state, and the decay of the excited state results in a relaxation of the energy level into a ground state, accompanied by light-emission.
  • the most important factor determining luminous efficiency in the organic EL device is light-emitting materials.
  • the light-emitting material needs to have high quantum efficiency, high electron mobility, and high hole mobility.
  • the light-emitting layer formed by the light-emitting material needs to be uniform and stable.
  • the light-emitting materials can be classified as a blue-, green-, or red-emitting material, and can additionally include a yellow- or orange-emitting material.
  • the light-emitting material can be classified according to its function, as a host material and a dopant material. Recently, the development of OLED providing high efficiency and a long lifespan is urgent.
  • a host material which plays a role as a solvent in a solid state and transfers energy, should have high purity, and an appropriate molecular weight for being deposited under a vacuum.
  • a host material should have high glass transition temperature and high thermal decomposition temperature to ensure thermal stability; high electrochemical stability to have a long lifespan; ease of preparation for amorphous thin film; and good adhesion to materials of adjacent layers.
  • a host material should not move to an adjacent layer.
  • Japanese Patent Application Laying-Open No. 2014-160813 discloses a nitrogen-containing heterocyclic compound formed by condensing a pyrrole ring, an aromatic ring, and a 7-membered ring, and an organic electroluminescent element comprising the same. However, it does not disclose the compounds of the present disclosure, but discloses the compounds wherein aryl is fused to the backbone or that have the fusion positions different from those of the compounds of the present disclosure.
  • the objective of the present disclosure is to provide an organic electroluminescent compound, which is effective in preparing an organic electroluminescent device having low driving voltage, good luminous and power efficiencies, and a remarkably improved lifespan.
  • each of two adjacent * of one phenyl ring of formula 1 is bonded to each of two * of formula 2, and
  • R 1 to R 5 each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxy, a nitro, a hydroxy, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3 to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3 to 30-membered)heteroaryl, -NR 6 R 7 or -SiR 8 R 9 R 10 , or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30), mono- or polycyclic, alicyclic or aromatic ring,
  • R 6 to R 10 each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxy, a nitro, a hydroxy, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3 to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3 to 30-membered)heteroaryl;
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3 to 30-membered)heteroaryl;
  • a, c, d and e each independently, represent an integer of 1 to 4; b represents an integer of 1 to 3; and
  • the heteroaryl contains at least one hetero atom selected from B, N, O, S, Si and P.
  • the organic electroluminescent compounds of the present disclosure have an advantage in that when they are used as a host of a light-emitting layer, they can provide an organic electroluminescent device having low driving voltage, and remarkably improved luminous efficiency and lifespan, compared to conventional organic light-emitting compounds.
  • the organic electroluminescent compounds of the present disclosure can provide an organic electroluminescent device having low driving voltage and high current and power efficiencies.
  • the present disclosure provides the organic electroluminescent compound of formula 1 above, an organic electroluminescent material comprising the same, and an organic electroluminescent device comprising the material.
  • R 1 to R 5 each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxy, a nitro, a hydroxy, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30) cycloalkenyl, a substituted or unsubstituted (3 to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3 to 30-membered)heteroaryl, -NR 6 R 7 or -SiR 8 R 9 R 10 , or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C30), mono- or polycyclic, alipha-1-methyl-1-methyl
  • R 6 to R 10 each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxy, a nitro, a hydroxy, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3 to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3 to 30-membered)heteroaryl; preferably, each independently, may represent a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C3-C20)cycloalkyl, a substituted or un
  • Ar 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3 to 30-membered)heteroaryl; preferably, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (3 to 25-membered)heteroaryl; more preferably, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted, nitrogen-, oxygen- or sulfur-containing (5 to 20-membered)heteroaryl; specifically, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted terphenyl, a substituted or unsubsti
  • a, c, d and e each independently, represent an integer of 1 to 4, and b represents an integer of 1 to 3.
  • a to e each independently, may represent 1 or 2.
  • the compound of formula 1 of the present disclosure may be represented by the following formulae 3 to 6:
  • f and g each independently, represent an integer of 1 or 2.
  • R 1 to R 5 , Ar 1 , a, b, c, d and e are as defined in formula 1 above.
  • (C1-C30)alkyl indicates a linear or branched alkyl having 1 to 30, preferably 1 to 20, and more preferably 1 to 10 carbon atoms, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
  • “(C2-C30) alkenyl” indicates a linear or branched alkenyl having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl indicates a linear or branched alkynyl having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
  • (C1-C30)alkoxy indicates a linear or branched alkoxy having 1 to 30, preferably 1 to 20, and more preferably 1 to 10 carbon atoms, and includes methoxy, ethoxy, propoxy, isopropoxy, 1-ethylpropoxy, etc.
  • (C3-C30)cycloalkyl indicates a mono- or polycyclic hydrocarbon having 3 to 30, preferabley 3 to 20, more preferably 3 to 7 ring backbone carbon atoms.
  • the cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • (3 to 7-membered)heterocycloalkyl indicates a cycloalkyl having 3 to 7 ring backbone atoms including at least one hetero atom selected from B, N, O, S, Si, and P, preferably O, S, and N, and includes pyrrolidine, thiolan, tetrahydropyran, etc.
  • (C6-C30)aryl(ene) indicates a monocyclic ring-type or fused ring-type radical derived from aromatic hydrocarbon having 6 to 30, preferabley 6 to 20, more preferably 6 to 15 ring backbone carbon atoms.
  • the aryl may include aryl having a spiro structure.
  • the aryl includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
  • (3 to 30-membered)heteroaryl(ene) indicates an aryl group having 3 to 30, preferabley 3 to 20, more preferably 3 to 15 ring backbone atoms including at least one, preferably 1 to 4, hetero atom selected from the group consisting of B, N, O, S, Si, and P; may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazoly
  • substituted in the expression, “substituted or unsubstituted,” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e. a substituent.
  • R 1 to R 5 each independently, may represent hydrogen, deuterium, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C3-C20)cycloalkyl, a substituted or unsubstituted (C3-C20)cycloalkenyl, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted (3 to 20-membered)heteroaryl, or -NR 6 R 7 , or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (C3-C20), mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur; wherein R 6 and R 7 , each independently, may represent a substituted or unsubstituted (C1-C20)alkyl,
  • R 1 to R 4 each independently, may respresent hydrogen;
  • R 5 may represent hydrogen, or an unsubstituted (C6-C18)ary, or may be linked to an adjacent substituent(s) to form an unsubstituted (C3-C18) mono- or polycyclic, aromatic ring;
  • Ar 1 may represent a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5 to 20-membered)heteroaryl;
  • a, c, d and e may be 1; and
  • b may be 2.
  • organic electroluminescent compound of formula 1 of the present disclosure includes the following, but is not limited thereto:
  • the present disclosure provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
  • the material may consist of the organic electroluminescent compound alone of the present disclosure. Otherwise, the material may further comprise a conventional compound(s) which has been comprised in an organic electroluminescent material, in addition to the compound of the present disclosure.
  • the organic electroluminescent device of the present disclosure may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes.
  • the organic layer may comprise at least one organic electroluminescent compound of formula 1.
  • the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, an auxiliary light-emitting layer, an electron transport layer, an electron buffering layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer, wherein the hole auxiliary layer or the auxiliary light-emitting layer is interposed between the hole transport layer and the light-emitting layer, and modulates hole mobility.
  • the hole auxiliary layer or the auxiliary light-emitting layer has the effects to provide improved efficiency and lifespan of the organic electroluminescent device.
  • the organic electroluminescent compound of formula 1 of the present disclosure may be comprised in the light-emitting layer as a host material.
  • the light-emitting layer may further comprise at least one dopant, and if needed, a compound other than the organic electroluminescent compound of formula 1 of the present disclosure may be comprised additionally as a second host material.
  • a material for preparing an organic electroluminescent device may comprise a first host material and a second host material, wherein the first host material comprises the organic electroluminescent compound of the present disclosure.
  • the weight ratio between the first host material and the second host material is in the range of 1:99 to 99:1.
  • the second host material may be from any of the known phosphorescent host materials.
  • the second host material may be selected from the group consisting of the phosphorescent hosts of formulae 7 to 11 below.
  • A represents -O- or -S-;
  • R 21 to R 24 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5 to 30-membered)heteroaryl or -SiR 25 R 26 R 27 ;
  • R 25 to R 27 each independently, represent a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl;
  • L 4 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5 to 30-membered)heteroarylene;
  • M represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5 to 30-membered
  • the second host material preferably includes the following:
  • the dopant to be comprised in the organic electroluminescent device of the present disclosure is preferably at least one phosphorescent dopant.
  • the phosphorescent dopant material for the organic electroluminescent device of the present disclosure is not limited, but may be preferably selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
  • the compounds represented by the following formulae 101 to 103 may be used as the dopant to be comprised in the organic electroluminescent device of the present disclosure.
  • L d is selected from the following structures:
  • R 100 represents hydrogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
  • R 101 to R 109 and R 111 to R 123 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alky substituted or unsubstituted with a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
  • R 106 to R 109 each independently, may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a fluorene substituted or unsubstituted with an alkyl, a dibenzothiophene substituted or unsubstituted with an alkyl, or a dibenzofuran substituted or unsubstituted with an alkyl;
  • R 120 to R 123 each independently,
  • R 124 to R 127 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl;
  • R 124 to R 127 each independently, may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a fluorene substituted or unsubstituted with an alkyl, a dibenzothiophene substituted or unsubstituted with an alkyl, or a dibenzofuran substituted or unsubstituted with an alkyl;
  • R 201 to R 211 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl substituted or unsubstituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl;
  • R 201 to R 211 each independently, may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, for example, a fluorene substituted or unsubstituted with an alkyl, a dibenzothiophene substituted or unsubstituted with an alkyl, or a dibenzofuran substituted or unsubstituted with an alkyl;
  • r and s each independently, represent an integer of 1 to 3; when r or s is an integer of 2 or more, each of R 100 may be the same or different; and
  • t represents an integer of 1 to 3.
  • the phosphorescent dopant includes the following:
  • the organic electroluminescent device of the present disclosure comprises an organic electroluminescent compound of formula 1, and may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
  • the organic layer may further comprise, in addition to the compound of formula 1, at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising the metal.
  • the organic layer may further comprise a light-emitting layer and a charge generating layer.
  • the organic electroluminescent device of the present disclosure may emit white light by further comprising at least one light-emitting layer, which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the field, besides the compound of the present disclosure. If necessary, it may further comprise an orange light-emitting layer or a yellow light-emitting layer.
  • at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound known in the field, besides the compound of the present disclosure. If necessary, it may further comprise an orange light-emitting layer or a yellow light-emitting layer.
  • a surface layer may be placed on an inner surface(s) of one or both electrode(s), selected from a chalcogenide layer, a metal halide layer and a metal oxide layer.
  • a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
  • a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
  • the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
  • the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds
  • the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more light-emitting layers and emitting white light.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, and flow coating methods can be used.
  • a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
  • organic electroluminescent compound of the present disclosure the preparation method of the compound, and the luminescent properties of the organic electroluminescent device comprising the compound will be explained in detail with reference to the following examples.
  • OLED was produced using the organic electroluminescent material of the present disclosure as follows.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an organic electroluminescent device (OLED) (Geomatec) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water sequentially, and was then stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • Compound HI-1 was introduced into a cell of the vacuum vapor depositing apparatus, and then the pressure in the chamber of the apparatus was controlled to 10 -6 torr.
  • an electric current was applied to the cell to evaporate compound HI-1 , thereby forming a first hole injection layer having a thickness of 80nm on the ITO substrate.
  • Compound HI-2 was then introduced into another cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a second hole injection layer having a thickness of 5nm on the first hole injection layer.
  • Compound HT-1 was introduced into one cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a first hole transport layer having a thickness of 10nm on the second hole injection layer.
  • Compound HT-3 was then introduced into another cell of the vacuum vapor depositing apparatus, and evaporated by applying electric current to the cell, thereby forming a second hole transport layer having a thickness of 60nm on the first hole transport layer.
  • a light-emitting layer was deposited thereon as follows.
  • Compound C-13 was introduced, as a host material, into a cell of the vacuum vapor depositing apparatus, and compound D-71 was introduced into another cell. The two compounds were then evaporated at different rates, so that the dopant was deposited in a doping amount of 3 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 40nm on the hole transport layer.
  • Compounds ET-1 and EI-1 were then introduced into another two cells of the vacuum vapor depositing apparatus, respectively, and evaporated at the same rate of 1:1, thereby forming an electron transport layer having a thickness of 30nm on the light-emitting layer.
  • an Al cathode having a thickness of 80nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer to produce OLED.
  • the produced OLED showed red emission having efficiency of 24.1cd/A at 4.2V of voltage and a luminance of 1,000cd/m 2 .
  • OLED was produced in the same manner as in Device Example 1, except that the compound shown in Table 1 below was used as a host for a light-emitting layer.
  • OLED was produced in the same manner as in the Device Examples, except for using compound B as a host for a light-emitting layer.
  • the produced OLED showed red emission having efficiency of 3.3cd/A at 8.2V of voltage and a luminance of 1,000cd/m 2 .
  • the organic electroluminescent compound of the present disclosure has better luminous efficiency than conventional compounds and especially shows excellence in current and power efficiencies.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention porte sur un composé électroluminescent organique et sur un dispositif électroluminescent organique comprenant ce composé électroluminescent organique. Le composé électroluminescent organique selon la présente invention est efficace dans la préparation d'un dispositif électroluminescent organique ayant une faible tension de commande et une bonne efficacité de courant et de puissance.
PCT/KR2016/008476 2015-09-10 2016-08-02 Composés électroluminescents organiques et dispositif électroluminescent organique les comprenant WO2017043770A1 (fr)

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US15/747,893 US20180223184A1 (en) 2015-09-10 2016-08-02 Organic electroluminescent compounds and organic electroluminescent device comprising the same
CN201680049101.5A CN107922424A (zh) 2015-09-10 2016-08-02 有机电致发光化合物和包含所述化合物的有机电致发光装置

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Publication number Priority date Publication date Assignee Title
WO2018021841A1 (fr) 2016-07-27 2018-02-01 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
WO2019143184A1 (fr) * 2018-01-19 2019-07-25 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce dernier
JP2019529340A (ja) * 2016-07-27 2019-10-17 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機電界発光化合物およびそれを含む有機電界発光デバイス
US11706977B2 (en) 2018-01-11 2023-07-18 Samsung Electronics Co., Ltd. Heterocyclic compound, composition including the same, and organic light-emitting device including the heterocyclic compound

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JP2014160813A (ja) * 2013-01-24 2014-09-04 Idemitsu Kosan Co Ltd 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子、並びに含窒素複素環化合物
KR20150077220A (ko) * 2013-12-27 2015-07-07 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2016052962A1 (fr) * 2014-09-29 2016-04-07 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé

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JP2014160813A (ja) * 2013-01-24 2014-09-04 Idemitsu Kosan Co Ltd 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子、並びに含窒素複素環化合物
KR20150077220A (ko) * 2013-12-27 2015-07-07 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2016052962A1 (fr) * 2014-09-29 2016-04-07 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018021841A1 (fr) 2016-07-27 2018-02-01 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
JP2019529340A (ja) * 2016-07-27 2019-10-17 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機電界発光化合物およびそれを含む有機電界発光デバイス
US11706977B2 (en) 2018-01-11 2023-07-18 Samsung Electronics Co., Ltd. Heterocyclic compound, composition including the same, and organic light-emitting device including the heterocyclic compound
WO2019143184A1 (fr) * 2018-01-19 2019-07-25 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce dernier
US11788000B2 (en) 2018-01-19 2023-10-17 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same

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