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WO2017078403A1 - A plurality of host materials and organic electroluminescent device comprising the same - Google Patents

A plurality of host materials and organic electroluminescent device comprising the same Download PDF

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Publication number
WO2017078403A1
WO2017078403A1 PCT/KR2016/012532 KR2016012532W WO2017078403A1 WO 2017078403 A1 WO2017078403 A1 WO 2017078403A1 KR 2016012532 W KR2016012532 W KR 2016012532W WO 2017078403 A1 WO2017078403 A1 WO 2017078403A1
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substituted
unsubstituted
alkyl
aryl
membered
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Yoo-Jin DOH
Kyoung-Jin Park
Chi-Sik Kim
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DuPont Specialty Materials Korea Ltd
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Rohm and Haas Electronic Materials Korea Ltd
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Definitions

  • the present disclosure relates to a plurality of host materials and organic electroluminescent device comprising the same.
  • An electroluminescent device is a self-light-emitting display device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
  • the first organic EL device was developed by Eastman Kodak in 1987, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • An organic electroluminescent device (hereinafter abbreviated as an OLED) is a device changing electrical energy to light by applying electricity to an organic electroluminescent material, and generally has a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode.
  • the organic layer of an OLED may comprise a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer (comprising host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.
  • the materials used for the organic layer may be categorized by their functions in hole injection materials, hole transport materials, hole auxiliary materials, light-emitting auxiliary materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc.
  • holes are injected from the anode to the light-emitting layer
  • electrons are injected from the cathode to the light-emitting layer
  • excitons of high energies are formed by a recombination of the holes and the electrons.
  • organic luminescent compounds reach an excited state, and light emission occurs by emitting light from energy due to returning from the excited state of the organic luminescent compounds to a ground state.
  • a light-emitting material must have high quantum efficiency, and high electron and hole mobility, and the formed light-emitting material layer must be uniform and stable.
  • Light-emitting materials are categorized into blue, green, and red light-emitting materials dependent on the color of the light emission, and additionally yellow or orange light-emitting materials.
  • light-emitting materials can also be categorized into host and dopant materials according to their functions. Recently, the development of an OLED having high efficiency and long lifespan is an urgent issue. In particular, considering EL characteristic requirements for a middle or large-sized panel of OLED, light-emitting materials showing excellent characteristics compared to conventional ones must be urgently developed.
  • the host material which acts as a solvent in a solid state and an energy transferer, is desirable to have high purity and an appropriate molecular weight capable of a vacuum deposition. Furthermore, the host material is desirable to have high glass transition temperature and high thermal degradation temperature to achieve thermal stability, high electro-chemical stability to achieve a long lifespan, ease of forming an amorphous thin film, good adhesion to materials of adjacent layers, and non-migration to other layers.
  • the light-emitting material can be used by combining a host with a dopant to improve color purity, luminous efficiency, and stability.
  • a device showing good EL performances comprises a light-emitting layer prepared by doping a dopant to a host.
  • the host material greatly influences the efficiency and lifespan of the EL device when using a host/dopant system, and thus its selection is important.
  • Korean Patent Application Laid-Open No. 2011-0134885 discloses an organic electroluminescent device using the compound comprising an indolocarbazole derivative and a triazine derivative as a host material.
  • the aforementioned publication does not specifically disclose an organic electroluminescent device using an indolocarbazole derivative substituted with a benzothiazole, a benzoxazole or a substituted benzimidazole, and a carbazole derivative comprising a nitrogen-containing heteroaryl as a plurality of host materials.
  • the object of the present disclosure is to provide an organic electroluminescent device having a long lifespan.
  • the present inventors found that the above objective can be achieved by a plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula 1:
  • X 1 to X 14 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or substitute
  • R 1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene
  • Z represents S, O, or NR 4 ;
  • R 2 to R 4 each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, 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;
  • Ma represents a substituted or unsubstituted nitrogen-containing (5- to 30-membered)heteroaryl
  • La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene
  • V and W represents a single bond, and the other of V and W represents any one of NR 5 , CR 6 R 7 , S and O;
  • Xa to Xi each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or substitute
  • R 5 to R 7 each independently, represent 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; and
  • the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P.
  • an organic electroluminescent device having a long lifespan is provided.
  • the organic electroluminescent device of the present disclosure can be used for the manufacture of a display device or a lighting device.
  • X 1 to X 14 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a
  • X 1 to X 14 each independently, represent hydrogen, or a substituted or unsubstituted (C6-C30)aryl; or may be linked to adjacent X 1 to X 14 , respectively, to form a substituted or unsubstituted mono- or polycyclic (C3-C25), alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
  • X 1 to X 14 each independently, represent hydrogen, or an unsubstituted (C6-C18)aryl; or may be linked to adjacent X 1 to X 14 , respectively, to form an unsubstituted mono- or polycyclic (C3-C18) aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from oxygen and sulfur.
  • X 1 to X 14 each independently, may represent hydrogen, or may be linked to adjacent X 1 to X 14 , respectively, to form a benzene ring, a benzothiophene ring, or a benzofuran ring.
  • R 1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene; preferably, a substituted or unsubstituted (C6-C25)arylene; more preferably, an unsubstituted (C6-C18)arylene; and for example, an unsubstituted phenylene.
  • Z represents S, O, or NR 4 .
  • R 4 represents hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, 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, a substituted or unsubstituted (C6-C25)aryl; more preferably, an unsubstituted (C6-C18)aryl; and for example, an unsub
  • R 2 and R 3 each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, 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, a substituted or unsubstituted (C6-C25)aryl; more preferably, an unsubstituted (C6-C18)aryl; and for example, an unsubstituted pheny
  • Ma represents a substituted or unsubstituted nitrogen-containing (5- to 30-membered)heteroaryl; preferably, a substituted or unsubstituted nitrogen-containing (5- to 25-membered)heteroaryl; more preferably, a substituted or unsubstituted nitrogen-containing (5- to 18-membered)heteroaryl; and for example, a substituted triazinyl, a substituted pyrimidinyl, a substituted benzimidazolyl, a substituted quinoxalinyl, a substituted quinolyl, a substituted quinazolinyl, or an unsubstituted naphthyridinyl.
  • La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene; preferably, a single bond, or a substituted or unsubstituted (C6-C25)arylene; more preferably, a single bond, or a substituted or unsubstituted (C6-C18)arylene; and for example, a single bond, a phenylene unsubstituted or substituted with a triphenylsilyl, an unsubstituted biphenylene, or an unsubstituted naphthylene.
  • one of V and W represents a single bond, and the other of V and W represents any one of NR 5 , CR 6 R 7 , S and O.
  • one of V and W represents a single bond, and the other of V and W represents any one of NR 5 , S and O.
  • Xa to Xi each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a
  • Xa to Xi each independently, represent hydrogen, a cyano, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 25-membered)heteroaryl, or a substituted or unsubstituted tri(C6-C25)arylsilyl. More preferably, Xa to Xi, each independently, represent hydrogen, a cyano, a substituted or unsubstituted (C6-C18)aryl, a substituted or unsubstituted (6- to 18-membered)heteroaryl, or an unsubstituted tri(C6-C18)arylsilyl.
  • Xa to Xi each independently, may represent hydrogen, a cyano, a phenyl unsubstituted or substituted with a tert-butyl, an unsubstituted naphthyl, unsubstituted biphenyl, a carbazolyl unsubstituted or substituted with a phenyl, an unsubstituted dibenzothiophenyl, or an unsubstituted triphenylsilyl.
  • R 5 to R 7 each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, 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, a substituted or unsubstituted (C6-C25)aryl; more preferably, a substituted or unsubstituted (C6-C18)aryl; and for example, a phenyl
  • the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P, and preferably, at least one heteroatom selected from N, O, S, and Si.
  • R 1 and La each independently, may be represented by any one of the following formulas 3 to 15:
  • Xj to Xq each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a
  • Xj to Xq each independently, represent hydrogen, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted tri(C6-C25)arylsilyl. More preferably, Xj to Xq, each independently, represent hydrogen, or an unsubstituted tri(C6-C18)arylsilyl. For example, Xj to Xq, each independently, may represent hydrogen, or an unsubstituted triphenylsilyl.
  • (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
  • (C2-C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl is meant to be a linear or branched alkynyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
  • (C3-C30)cycloalkyl is a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • (3- to 7- membered) heterocycloalkyl is a cycloalkyl having 3 to 7, preferably 5 to 7, ring backbone atoms, including at least one heteroatom selected from B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
  • (C6-C60)aryl(ene) is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 60 ring backbone carbon atoms, which may be partially saturated, in which the number of the ring backbone carbon atoms is preferably 6 to 30, more preferably 6 to 20.
  • the above aryl(ene) may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
  • (3- to 30-membered)heteroaryl is an aryl having 3 to 30 ring backbone atoms, including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P.
  • the above heteroaryl 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, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, is
  • nitrogen-containing (5- to 30-membered)heteroaryl is an aryl having 5 to 30 ring backbone atoms, preferably 5 to 20 ring backbone atoms, more preferably 5 to 15 ring backbone atoms, containing at least one, preferably 1 to 4, nitrogen as the heteroatom.
  • the above nitrogen-containing heteroaryl 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 pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl,
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group, i.e. a substituent.
  • the compound represented by formula 1 may be exemplified as the following compounds, but is not limited thereto:
  • the compound represented by formula 1 of the present disclosure may be produced by a synthetic method known to a person skilled in the art, for example, the following Reaction Scheme 1, but is not limited thereto:
  • the compound represented by formula 2 may be exemplified as the following compounds, but is not limited thereto:
  • the compound represented by formula 2 of the present disclosure may be produced by a synthetic method known to a person skilled in the art, in particular, a synthetic method disclosed in numerous patent publications.
  • compounds B-1, B-27, B-32 and B-35 which are the well-known materials, may be synthesized by the method disclosed in the following Patent Application Laid-Open, but is not limited thereto.
  • the synthesis methods of compound B-1 and the derivatives thereof are disclosed in Korean Patent Application Laid-Open No. 2016-0010333, published on January 27, 2016. Also, the synthesis methods of compound B-27 and the derivatives thereof are disclosed in Korean Patent Application Laid-Open No. 2013-0011446, published on January 30, 2013. Further, the synthesis methods of compound B-32 and the derivatives thereof are disclosed in Korean Patent Application Laid-Open No. 2013-0011405, published on January 30, 2013. Furthermore, the synthesis methods of compound B-35 and the derivatives thereof are disclosed in Korean Patent Application Laid-Open No. 2013-0094903, published on August 27, 2013.
  • the organic electroluminescent device of the present disclosure may comprise an anode; a cathode; and at least one organic layer disposed between the anode and the cathode, wherein the organic layer may comprise a light-emitting layer, wherein the light-emitting layer may comprise a host and a dopant, wherein the host may comprise a plurality of host compounds, and wherein at least one first host compound of the plurality of host compounds may be represented by formula 1, and at least one second host compound of the plurality of host compounds may be represented by formula 2.
  • the light-emitting layer of the present disclosure may be a layer from which light is emitted, and may be a single layer or a multiple layer deposited by two or more layers. It is preferable that a doping amount of the dopant compound is less than 20 wt% based on the total amount of the host compound and the dopant compound.
  • 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, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
  • the hole auxiliary layer or the light-emitting auxiliary layer may be placed between the hole transport layer and the light-emitting layer, which may control a transport rate of a hole.
  • the hole auxiliary layer or the light-emitting auxiliary layer may be effective to produce an organic electroluminescent device having excellent efficiencies and/or improved lifespan.
  • the weight ratio of the first host compound to the second host compound is in the range of 1:99 to 99:1.
  • the dopant comprised in the organic electroluminescent device of the present disclosure is preferably at least one phosphorescent dopant.
  • the phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particulary limited, but may be preferably selected from the metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
  • the dopant comprised in the organic electroluminescent device of the present disclosure may comprise the compound selected from the group consisting of the compounds represented by the following formulas 101 to 103.
  • L is selected from the following structures:
  • R 100 represents hydrogen, deuterium, 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 substituted or unsubstituted (C1-C30)alkyl, 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 may be linked to adjacent R 106 to R 109 , respectively, to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl; and R 120 to R 123 may be linked to
  • 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; and R 124 to R 127 may be linked to adjacent R 124 to R 127 , respectively, to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl;
  • R 201 to R 211 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; and R 208 to R 211 may be linked to adjacent R 208 to R 211 , respectively, to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl;
  • r and s each independently, represent an integer of 1 to 3; where if r or s is an integer of 2 or more, each R 100 may be the same or different; and
  • e represents an integer of 1 to 3.
  • the organic electroluminescent device of the present disclosure may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in an organic layer.
  • the organic layer may further comprise 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 such metal.
  • 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 (including oxides) layer of silicon and/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 hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be disposed between the anode and the light-emitting layer.
  • the hole injection layer may be composed of two or more layers in order to lower an energy barrier for injecting holes from the anode to a hole transport layer or an electron blocking layer (or a voltage for injecting holes). Each of the layers may comprise two or more compounds.
  • the hole transport layer or electron blocking layer may be composed of two or more layers.
  • An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be disposed between the light-emitting layer and the cathode.
  • the electron buffer layer may be composed of two or more layers in order to control the electron injection and improve characteristics of interface between the light-emitting layer and the electron injection layer.
  • Each of the layers may comprise two or more compounds.
  • the hole blocking layer or electron transport layer may be composed of two or more layers, and each of the layers may comprise two or more compounds.
  • 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 organic electroluminescent device having two or more light-emitting layers and emitting white light.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc.
  • wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc.
  • 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.
  • the first and the second host compounds of the present disclosure may be film-formed by a co-evaporation process or a mixture-evaporation process.
  • the organic electroluminescent device of the present disclosure can be used for the manufacture of a display device or a lighting device.
  • Device Examples 1-1 and 1-2 Producing an OLED device by a co-evaporation of a first and a second host compounds of the present disclosure as a host
  • An OLED device was produced by using the compound according to the present disclosure.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED device (Geomatec) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol.
  • the ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition apparatus.
  • Compound HI-1 was introduced into a cell of the vacuum vapor deposition 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 the above-introduced material, thereby forming a hole injection layer having a thickness of 5 nm on the ITO substrate.
  • Compound HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 95 nm on the hole injection layer.
  • compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 20 nm on the first hole transport layer.
  • a light-emitting layer was formed thereon as follows:
  • a first host compound and a second host compound of Device Examples 1-1 and 1-2 shown in Table 1 below were introduced into two cells of the vacuum vapor depositing apparatus, respectively.
  • Compound D-74 was introduced into another cell as a dopant.
  • the two host compounds were evaporated at the same rate of 1:1, while the dopant was evaporated at a different rate from the host compounds, so that the dopant was deposited in a doping amount of 12 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the second hole transport layer.
  • Compound ET-1 was deposited as an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus. Thus, an OLED device was produced.
  • Comparative Examples 1-1 and 1-2 Producing an OLED device comprising a
  • OLED device was produced in the same manner as in Device Examples 1-1 and 1-2, except for using the compounds of Comparative Examples 1-1 and 1-2 shown in Table 1 below as a host for a light-emitting layer.
  • the driving voltage at 10 mA/cm2, and the time taken to be reduced from 100% to 97% of the luminance at 10,000 nits and a constant current (Lifespan; T97) of the OLED devices produced in Device Examples 1-1 to 1-2 and Comparative Examples 1-1 and 1-2 are provided in Table 1 below.

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Abstract

The present disclosure relates to a plurality of host materials and an organic electroluminescent device comprising the same. By using a specific combination of a plurality of host compounds, it is possible to provide the organic electroluminescent device of the present disclosure having excellent lifespan properties.

Description

A PLURALITY OF HOST MATERIALS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
The present disclosure relates to a plurality of host materials and organic electroluminescent device comprising the same.
An electroluminescent device (EL device) is a self-light-emitting display device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time. The first organic EL device was developed by Eastman Kodak in 1987, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
An organic electroluminescent device (hereinafter abbreviated as an OLED) is a device changing electrical energy to light by applying electricity to an organic electroluminescent material, and generally has a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer of an OLED, if necessary, may comprise a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer (comprising host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. The materials used for the organic layer may be categorized by their functions in hole injection materials, hole transport materials, hole auxiliary materials, light-emitting auxiliary materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. In the OLED, due to an application of a voltage, holes are injected from the anode to the light-emitting layer, electrons are injected from the cathode to the light-emitting layer, and excitons of high energies are formed by a recombination of the holes and the electrons. By this energy, organic luminescent compounds reach an excited state, and light emission occurs by emitting light from energy due to returning from the excited state of the organic luminescent compounds to a ground state.
The most important factor determining luminous efficiency in an OLED is a light-emitting material. A light-emitting material must have high quantum efficiency, and high electron and hole mobility, and the formed light-emitting material layer must be uniform and stable. Light-emitting materials are categorized into blue, green, and red light-emitting materials dependent on the color of the light emission, and additionally yellow or orange light-emitting materials. In addition, light-emitting materials can also be categorized into host and dopant materials according to their functions. Recently, the development of an OLED having high efficiency and long lifespan is an urgent issue. In particular, considering EL characteristic requirements for a middle or large-sized panel of OLED, light-emitting materials showing excellent characteristics compared to conventional ones must be urgently developed. The host material, which acts as a solvent in a solid state and an energy transferer, is desirable to have high purity and an appropriate molecular weight capable of a vacuum deposition. Furthermore, the host material is desirable to have high glass transition temperature and high thermal degradation temperature to achieve thermal stability, high electro-chemical stability to achieve a long lifespan, ease of forming an amorphous thin film, good adhesion to materials of adjacent layers, and non-migration to other layers.
The light-emitting material can be used by combining a host with a dopant to improve color purity, luminous efficiency, and stability. Generally, a device showing good EL performances comprises a light-emitting layer prepared by doping a dopant to a host. The host material greatly influences the efficiency and lifespan of the EL device when using a host/dopant system, and thus its selection is important.
Korean Patent Application Laid-Open No. 2011-0134885 discloses an organic electroluminescent device using the compound comprising an indolocarbazole derivative and a triazine derivative as a host material. However, the aforementioned publication does not specifically disclose an organic electroluminescent device using an indolocarbazole derivative substituted with a benzothiazole, a benzoxazole or a substituted benzimidazole, and a carbazole derivative comprising a nitrogen-containing heteroaryl as a plurality of host materials.
The object of the present disclosure is to provide an organic electroluminescent device having a long lifespan.
As a result of intensive studies to solve the technical problem above, the present inventors found that the above objective can be achieved by a plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula 1:
Figure PCTKR2016012532-appb-I000001
X1 to X14, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or may be linked to adjacent X1 to X14, respectively, to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;
R1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;
Z represents S, O, or NR4; and
R2 to R4, each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, 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;
and the second host compound is represented by the following formula 2:
Figure PCTKR2016012532-appb-I000002
wherein
Ma represents a substituted or unsubstituted nitrogen-containing (5- to 30-membered)heteroaryl;
La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;
one of V and W represents a single bond, and the other of V and W represents any one of NR5, CR6R7, S and O;
Xa to Xi, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or may be linked to adjacent Xa to Xi, respectively, to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;
R5 to R7, each independently, represent 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; and
the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P.
According to the present disclosure, an organic electroluminescent device having a long lifespan is provided. In addition, the organic electroluminescent device of the present disclosure can be used for the manufacture of a display device or a lighting device.
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the disclosure, and is not meant in any way to restrict the scope of the disclosure.
The compounds represented by formulas 1 and 2 will be described in detail as follows.
In formula 1, X1 to X14, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or may be linked to adjacent X1 to X14, respectively, to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur. Preferably, X1 to X14, each independently, represent hydrogen, or a substituted or unsubstituted (C6-C30)aryl; or may be linked to adjacent X1 to X14, respectively, to form a substituted or unsubstituted mono- or polycyclic (C3-C25), alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur. More preferably, X1 to X14, each independently, represent hydrogen, or an unsubstituted (C6-C18)aryl; or may be linked to adjacent X1 to X14, respectively, to form an unsubstituted mono- or polycyclic (C3-C18) aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from oxygen and sulfur. For example, X1 to X14, each independently, may represent hydrogen, or may be linked to adjacent X1 to X14, respectively, to form a benzene ring, a benzothiophene ring, or a benzofuran ring.
In formula 1, R1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene; preferably, a substituted or unsubstituted (C6-C25)arylene; more preferably, an unsubstituted (C6-C18)arylene; and for example, an unsubstituted phenylene.
In formula 1, Z represents S, O, or NR4. Herein, R4 represents hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, 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, a substituted or unsubstituted (C6-C25)aryl; more preferably, an unsubstituted (C6-C18)aryl; and for example, an unsubstituted phenyl.
In formula 1, R2 and R3, each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, 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, a substituted or unsubstituted (C6-C25)aryl; more preferably, an unsubstituted (C6-C18)aryl; and for example, an unsubstituted phenyl, an unsubstituted biphenyl, or an unsubstituted naphthyl.
In formula 2, Ma represents a substituted or unsubstituted nitrogen-containing (5- to 30-membered)heteroaryl; preferably, a substituted or unsubstituted nitrogen-containing (5- to 25-membered)heteroaryl; more preferably, a substituted or unsubstituted nitrogen-containing (5- to 18-membered)heteroaryl; and for example, a substituted triazinyl, a substituted pyrimidinyl, a substituted benzimidazolyl, a substituted quinoxalinyl, a substituted quinolyl, a substituted quinazolinyl, or an unsubstituted naphthyridinyl.
In formula 2, La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene; preferably, a single bond, or a substituted or unsubstituted (C6-C25)arylene; more preferably, a single bond, or a substituted or unsubstituted (C6-C18)arylene; and for example, a single bond, a phenylene unsubstituted or substituted with a triphenylsilyl, an unsubstituted biphenylene, or an unsubstituted naphthylene.
In formula 2, one of V and W represents a single bond, and the other of V and W represents any one of NR5, CR6R7, S and O. Preferably, one of V and W represents a single bond, and the other of V and W represents any one of NR5, S and O.
In formula 2, Xa to Xi, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur. Preferably, Xa to Xi, each independently, represent hydrogen, a cyano, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 25-membered)heteroaryl, or a substituted or unsubstituted tri(C6-C25)arylsilyl. More preferably, Xa to Xi, each independently, represent hydrogen, a cyano, a substituted or unsubstituted (C6-C18)aryl, a substituted or unsubstituted (6- to 18-membered)heteroaryl, or an unsubstituted tri(C6-C18)arylsilyl. For example, Xa to Xi, each independently, may represent hydrogen, a cyano, a phenyl unsubstituted or substituted with a tert-butyl, an unsubstituted naphthyl, unsubstituted biphenyl, a carbazolyl unsubstituted or substituted with a phenyl, an unsubstituted dibenzothiophenyl, or an unsubstituted triphenylsilyl.
In formula 2, R5 to R7, each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, 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, a substituted or unsubstituted (C6-C25)aryl; more preferably, a substituted or unsubstituted (C6-C18)aryl; and for example, a phenyl unsubstituted or substituted with a triphenylsilyl, or an unsubstituted biphenyl.
In formulas 1 and 2, the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P, and preferably, at least one heteroatom selected from N, O, S, and Si.
In formulas 1 and 2, R1 and La, each independently, may be represented by any one of the following formulas 3 to 15:
Figure PCTKR2016012532-appb-I000003
Figure PCTKR2016012532-appb-I000004
Figure PCTKR2016012532-appb-I000005
wherein, Xj to Xq, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or may be linked to adjacent Xj to Xq, respectively, to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur. Preferably, Xj to Xq, each independently, represent hydrogen, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted tri(C6-C25)arylsilyl. More preferably, Xj to Xq, each independently, represent hydrogen, or an unsubstituted tri(C6-C18)arylsilyl. For example, Xj to Xq, each independently, may represent hydrogen, or an unsubstituted triphenylsilyl.
Herein, the term “(C1-C30)alkyl” is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. The term “(C2-C30)alkenyl” is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. The term “(C2-C30)alkynyl” is meant to be a linear or branched alkynyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. The term “(C3-C30)cycloalkyl” is a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term “(3- to 7- membered) heterocycloalkyl” is a cycloalkyl having 3 to 7, preferably 5 to 7, ring backbone atoms, including at least one heteroatom selected from B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. The term “(C6-C60)aryl(ene)” is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 60 ring backbone carbon atoms, which may be partially saturated, in which the number of the ring backbone carbon atoms is preferably 6 to 30, more preferably 6 to 20. The above aryl(ene) may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. The term “(3- to 30-membered)heteroaryl” is an aryl having 3 to 30 ring backbone atoms, including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The above heteroaryl 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, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. The term “nitrogen-containing (5- to 30-membered)heteroaryl” is an aryl having 5 to 30 ring backbone atoms, preferably 5 to 20 ring backbone atoms, more preferably 5 to 15 ring backbone atoms, containing at least one, preferably 1 to 4, nitrogen as the heteroatom. The above nitrogen-containing heteroaryl 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 pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenanthridinyl, etc. Furthermore, “halogen” includes F, Cl, Br, and I.
Herein, “substituted” in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group, i.e. a substituent. The substituents of the substituted alkyl, the substituted alkenyl, the substituted alkynyl, the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted aryl(ene), the substituted heteroaryl, the substituted trialkylsilyl, the substituted triarylsilyl, the substituted dialkylarylsilyl, the substituted mono- or di- arylamino, and the substituted mono- or polycyclic, alicyclic or aromatic ring, or the combination thereof, in X1 to X14, R1 to R7, Ma, La, and Xa to Xi of formulas 1 and 2, each independently, are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl and/or a di(C6-C30)arylamino; a (C6-C30)aryl unsubstituted or substituted with a cyano, a (3- to 30-membered)heteroaryl, and/or a tri(C6-C30)arylsilyl; a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di- (C1-C30)alkylamino; a mono- or di- (C6-C30)arylamino; a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl; preferably, are at least one selected from the group consisting of a (C1-C20)alkyl; a (3- to 25-membered)heteroaryl unsubstituted or substituted with a (C6-C18)aryl; a (C6-C25)aryl unsubstituted or substituted with a cyano, a (3- to 20-membered)heteroaryl, and/or a tri(C6-C18)arylsilyl; a tri(C6-C18)arylsilyl; and a (C1-C20)alkyl(C6-C20)aryl; and for example, may be at least one selected from the group consisting of a tert-butyl, a substituted or unsubstituted phenyl, an unsubstituted naphthyl, an unsubstituted biphenyl, an unsubstituted terphenyl, an unsubstituted triphenylenyl, a diphenylfluorenyl, a carbazolyl substituted with a phenyl, an unsubstituted dibenzothiophenyl, and an unsubstituted triphenylsilyl, wherein, the substituents of the substituted phenyl may be at least one selected from the group consisting of a tert-butyl, a cyano, a triphenylsilyl, a dimethylfluorenyl, a dibenzothiophenyl, a carbazolyl unsubstituted or substituted with a phenyl, a benzimidazolyl substituted with a phenyl, and a benzothiazolyl.
Specifically, the compound represented by formula 1 may be exemplified as the following compounds, but is not limited thereto:
Figure PCTKR2016012532-appb-I000006
Figure PCTKR2016012532-appb-I000007
Figure PCTKR2016012532-appb-I000008
Figure PCTKR2016012532-appb-I000009
Figure PCTKR2016012532-appb-I000010
Figure PCTKR2016012532-appb-I000011
Figure PCTKR2016012532-appb-I000012
Figure PCTKR2016012532-appb-I000013
Figure PCTKR2016012532-appb-I000014
The compound represented by formula 1 of the present disclosure may be produced by a synthetic method known to a person skilled in the art, for example, the following Reaction Scheme 1, but is not limited thereto:
[Reaction Scheme 1]
Figure PCTKR2016012532-appb-I000015
Figure PCTKR2016012532-appb-I000016
Specifically, the compound represented by formula 2 may be exemplified as the following compounds, but is not limited thereto:
Figure PCTKR2016012532-appb-I000017
Figure PCTKR2016012532-appb-I000018
Figure PCTKR2016012532-appb-I000019
Figure PCTKR2016012532-appb-I000020
Figure PCTKR2016012532-appb-I000021
Figure PCTKR2016012532-appb-I000022
Figure PCTKR2016012532-appb-I000023
Figure PCTKR2016012532-appb-I000024
Figure PCTKR2016012532-appb-I000025
Figure PCTKR2016012532-appb-I000026
Figure PCTKR2016012532-appb-I000027
Figure PCTKR2016012532-appb-I000028
Figure PCTKR2016012532-appb-I000029
Figure PCTKR2016012532-appb-I000030
Figure PCTKR2016012532-appb-I000031
Figure PCTKR2016012532-appb-I000032
Figure PCTKR2016012532-appb-I000033
Figure PCTKR2016012532-appb-I000034
Figure PCTKR2016012532-appb-I000035
Figure PCTKR2016012532-appb-I000036
Figure PCTKR2016012532-appb-I000037
Figure PCTKR2016012532-appb-I000038
Figure PCTKR2016012532-appb-I000039
Figure PCTKR2016012532-appb-I000040
Figure PCTKR2016012532-appb-I000041
Figure PCTKR2016012532-appb-I000042
The compound represented by formula 2 of the present disclosure may be produced by a synthetic method known to a person skilled in the art, in particular, a synthetic method disclosed in numerous patent publications. For example, compounds B-1, B-27, B-32 and B-35, which are the well-known materials, may be synthesized by the method disclosed in the following Patent Application Laid-Open, but is not limited thereto.
The synthesis methods of compound B-1 and the derivatives thereof are disclosed in Korean Patent Application Laid-Open No. 2016-0010333, published on January 27, 2016. Also, the synthesis methods of compound B-27 and the derivatives thereof are disclosed in Korean Patent Application Laid-Open No. 2013-0011446, published on January 30, 2013. Further, the synthesis methods of compound B-32 and the derivatives thereof are disclosed in Korean Patent Application Laid-Open No. 2013-0011405, published on January 30, 2013. Furthermore, the synthesis methods of compound B-35 and the derivatives thereof are disclosed in Korean Patent Application Laid-Open No. 2013-0094903, published on August 27, 2013.
The organic electroluminescent device of the present disclosure may comprise an anode; a cathode; and at least one organic layer disposed between the anode and the cathode, wherein the organic layer may comprise a light-emitting layer, wherein the light-emitting layer may comprise a host and a dopant, wherein the host may comprise a plurality of host compounds, and wherein at least one first host compound of the plurality of host compounds may be represented by formula 1, and at least one second host compound of the plurality of host compounds may be represented by formula 2.
The light-emitting layer of the present disclosure may be a layer from which light is emitted, and may be a single layer or a multiple layer deposited by two or more layers. It is preferable that a doping amount of the dopant compound is less than 20 wt% based on the total amount of the host compound and the dopant compound.
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, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer. Herein, the hole auxiliary layer or the light-emitting auxiliary layer may be placed between the hole transport layer and the light-emitting layer, which may control a transport rate of a hole. The hole auxiliary layer or the light-emitting auxiliary layer may be effective to produce an organic electroluminescent device having excellent efficiencies and/or improved lifespan.
In the organic electroluminescent device of the present disclosure, the weight ratio of the first host compound to the second host compound is in the range of 1:99 to 99:1.
The dopant comprised in the organic electroluminescent device of the present disclosure is preferably at least one phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particulary limited, but may be preferably selected from the metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compounds.
The dopant comprised in the organic electroluminescent device of the present disclosure may comprise the compound selected from the group consisting of the compounds represented by the following formulas 101 to 103.
Figure PCTKR2016012532-appb-I000043
wherein, L is selected from the following structures:
Figure PCTKR2016012532-appb-I000044
R100 represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
R101 to R109 and R111 to R123, each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a cyano, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; R106 to R109 may be linked to adjacent R106 to R109, respectively, to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl; and R120 to R123 may be linked to adjacent R120 to R123, respectively, to form a substituted or unsubstituted fused ring, e.g., a quinoline unsubstituted or substituted with an alkyl or an aryl;
R124 to R127, each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; and R124 to R127 may be linked to adjacent R124 to R127, respectively, to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl;
R201 to R211, each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; and R208 to R211 may be linked to adjacent R208 to R211, respectively, to form a substituted or unsubstituted fused ring, e.g., a fluorene unsubstituted or substituted with an alkyl, a dibenzothiophene unsubstituted or substituted with an alkyl, or a dibenzofuran unsubstituted or substituted with an alkyl;
r and s, each independently, represent an integer of 1 to 3; where if r or s is an integer of 2 or more, each R100 may be the same or different; and
e represents an integer of 1 to 3.
The specific examples of the dopant are as follows:
Figure PCTKR2016012532-appb-I000045
Figure PCTKR2016012532-appb-I000046
Figure PCTKR2016012532-appb-I000047
Figure PCTKR2016012532-appb-I000048
Figure PCTKR2016012532-appb-I000049
Figure PCTKR2016012532-appb-I000050
Figure PCTKR2016012532-appb-I000051
Figure PCTKR2016012532-appb-I000052
Figure PCTKR2016012532-appb-I000053
Figure PCTKR2016012532-appb-I000054
Figure PCTKR2016012532-appb-I000055
Figure PCTKR2016012532-appb-I000056
Figure PCTKR2016012532-appb-I000057
Figure PCTKR2016012532-appb-I000058
Figure PCTKR2016012532-appb-I000059
Figure PCTKR2016012532-appb-I000060
Figure PCTKR2016012532-appb-I000061
Figure PCTKR2016012532-appb-I000062
Figure PCTKR2016012532-appb-I000063
Figure PCTKR2016012532-appb-I000064
Figure PCTKR2016012532-appb-I000065
Figure PCTKR2016012532-appb-I000066
Figure PCTKR2016012532-appb-I000067
Figure PCTKR2016012532-appb-I000068
Figure PCTKR2016012532-appb-I000069
The organic electroluminescent device of the present disclosure may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in an organic layer.
In the organic electroluminescent device of the present disclosure, the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides, and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising such metal.
In the organic electroluminescent device of the present disclosure, preferably, at least one layer (hereinafter, "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. Specifically, a chalcogenide (including oxides) layer of silicon and/or aluminum is preferably placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer. Such a surface layer provides operation stability for the organic electroluminescent device. Preferably, the chalcogenide includes SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and the metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be disposed between the anode and the light-emitting layer. The hole injection layer may be composed of two or more layers in order to lower an energy barrier for injecting holes from the anode to a hole transport layer or an electron blocking layer (or a voltage for injecting holes). Each of the layers may comprise two or more compounds. The hole transport layer or electron blocking layer may be composed of two or more layers.
An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be disposed between the light-emitting layer and the cathode. The electron buffer layer may be composed of two or more layers in order to control the electron injection and improve characteristics of interface between the light-emitting layer and the electron injection layer. Each of the layers may comprise two or more compounds. The hole blocking layer or electron transport layer may be composed of two or more layers, and each of the layers may comprise two or more compounds.
In the organic electroluminescent device of the present disclosure, 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. In this case, 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. Furthermore, 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. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds, and 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 organic electroluminescent device having two or more light-emitting layers and emitting white light.
In order to form each layer of the organic electroluminescent device of the present disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc., or wet film-forming methods such as ink jet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating methods, etc., can be used.
When using a wet film-forming method, 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.
The first and the second host compounds of the present disclosure may be film-formed by a co-evaporation process or a mixture-evaporation process.
Also, the organic electroluminescent device of the present disclosure can be used for the manufacture of a display device or a lighting device.
Hereinafter, the luminescent properties of the organic light-emitting diode (OLED) device comprising the host compound of the present disclosure will be explained in detail with reference to the following examples.
Device Examples 1-1 and 1-2: Producing an OLED device by a co-evaporation of a first and a second host compounds of the present disclosure as a host
An OLED device was produced by using the compound according to the present disclosure. A transparent electrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glass substrate for an OLED device (Geomatec) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol. The ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the above-introduced material, thereby forming a hole injection layer having a thickness of 5 nm on the ITO substrate. Compound HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 95 nm on the hole injection layer. Next, compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 20 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layers, a light-emitting layer was formed thereon as follows: As host materials, a first host compound and a second host compound of Device Examples 1-1 and 1-2 shown in Table 1 below were introduced into two cells of the vacuum vapor depositing apparatus, respectively. Compound D-74 was introduced into another cell as a dopant. The two host compounds were evaporated at the same rate of 1:1, while the dopant was evaporated at a different rate from the host compounds, so that the dopant was deposited in a doping amount of 12 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the second hole transport layer. Compound ET-1 was deposited as an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus. Thus, an OLED device was produced.
Figure PCTKR2016012532-appb-I000070
Comparative Examples 1-1 and 1-2: Producing an OLED device comprising a
second host compound of the present disclosure and a conventional
compound as a host
An OLED device was produced in the same manner as in Device Examples 1-1 and 1-2, except for using the compounds of Comparative Examples 1-1 and 1-2 shown in Table 1 below as a host for a light-emitting layer.
The driving voltage at 10 mA/cm2, and the time taken to be reduced from 100% to 97% of the luminance at 10,000 nits and a constant current (Lifespan; T97) of the OLED devices produced in Device Examples 1-1 to 1-2 and Comparative Examples 1-1 and 1-2 are provided in Table 1 below.
Figure PCTKR2016012532-appb-I000071
Figure PCTKR2016012532-appb-I000072
Comparing Device Example 1-1 with Comparative Example 1-1, and Device Example 1-2 with Comparative Example 1-2 shown in Table 1, respectively, it can be seen that the OLED device comprising both a first host compound and a second host compound of the present disclosure has a long lifespan compared to the OLED device comprising a conventional host compound.
By using a specific combination of a plurality of host materials, it is possible to provide the organic electroluminescent device of the present disclosure having long lifespan properties.

Claims (6)

  1. A host material comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula 1:
    Figure PCTKR2016012532-appb-I000073
    wherein
    X1 to X14, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or may be linked to adjacent X1 to X14, respectively, to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;
    R1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;
    Z represents S, O, or NR4; and
    R2 to R4, each independently, represent hydrogen, deuterium, a halogen, a cyano, a carboxyl, a nitro, a hydroxyl, 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;
    and the second host compound is represented by the following formula 2:
    Figure PCTKR2016012532-appb-I000074
    wherein
    Ma represents a substituted or unsubstituted nitrogen-containing (5- to 30-membered)heteroaryl;
    La represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;
    one of V and W represents a single bond, and the other of V and W represents any one of NR5, CR6R7, S and O;
    Xa to Xi, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or may be linked to adjacent Xa to Xi, respectively, to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;
    R5 to R7, each independently, represent 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; and
    the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P.
  2. The host material according to claim 1, wherein R1 and La, each independently, represent any one of the following formulas 3 to 15:
    Figure PCTKR2016012532-appb-I000075
    Figure PCTKR2016012532-appb-I000076
    Figure PCTKR2016012532-appb-I000077
    wherein
    Xj to Xq, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C2-C30)alkynyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C60)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or may be linked to adjacent Xj to Xq, respectively, to form a substituted or unsubstituted mono- or polycyclic (C3-C30), alicyclic or aromatic ring, or the combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
  3. The host material according to claim 1, wherein the substituents of the substituted alkyl, the substituted alkenyl, the substituted alkynyl, the substituted cycloalkyl, the substituted cycloalkenyl, the substituted heterocycloalkyl, the substituted aryl(ene), the substituted heteroaryl, the substituted trialkylsilyl, the substituted triarylsilyl, the substituted dialkylarylsilyl, the substituted mono- or di- arylamino, and the substituted mono- or polycyclic, alicyclic or aromatic ring, or the combination thereof, in X1 to X14, R1 to R7, Ma, La, and Xa to Xi, each independently, are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl or a di(C6-C30)arylamino; a (C6-C30)aryl unsubstituted or substituted with a cyano, a (3- to 30-membered)heteroaryl, or a tri(C6-C30)arylsilyl; a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di- (C1-C30)alkylamino; a mono- or di- (C6-C30)arylamino; a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl.
  4. The host material according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
    Figure PCTKR2016012532-appb-I000078
    Figure PCTKR2016012532-appb-I000079
    Figure PCTKR2016012532-appb-I000080
    Figure PCTKR2016012532-appb-I000081
    Figure PCTKR2016012532-appb-I000082
    Figure PCTKR2016012532-appb-I000083
    Figure PCTKR2016012532-appb-I000084
    Figure PCTKR2016012532-appb-I000085
    Figure PCTKR2016012532-appb-I000086
  5. The host material according to claim 1, wherein the compound represented by formula 2 is selected from the group consisting of:
    Figure PCTKR2016012532-appb-I000087
    Figure PCTKR2016012532-appb-I000088
    Figure PCTKR2016012532-appb-I000089
    Figure PCTKR2016012532-appb-I000090
    Figure PCTKR2016012532-appb-I000091
    Figure PCTKR2016012532-appb-I000092
    Figure PCTKR2016012532-appb-I000093
    Figure PCTKR2016012532-appb-I000094
    Figure PCTKR2016012532-appb-I000095
    Figure PCTKR2016012532-appb-I000096
    Figure PCTKR2016012532-appb-I000097
    Figure PCTKR2016012532-appb-I000098
    Figure PCTKR2016012532-appb-I000099
    Figure PCTKR2016012532-appb-I000100
    Figure PCTKR2016012532-appb-I000101
    Figure PCTKR2016012532-appb-I000102
    Figure PCTKR2016012532-appb-I000103
    Figure PCTKR2016012532-appb-I000104
    Figure PCTKR2016012532-appb-I000105
    Figure PCTKR2016012532-appb-I000106
    Figure PCTKR2016012532-appb-I000107
    Figure PCTKR2016012532-appb-I000108
    Figure PCTKR2016012532-appb-I000109
    Figure PCTKR2016012532-appb-I000110
    Figure PCTKR2016012532-appb-I000111
    Figure PCTKR2016012532-appb-I000112
  6. An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer disposed between the anode and the cathode, wherein the light-emitting layer comprises a host and a dopant, and wherein the host comprises the host material according to claim 1.
PCT/KR2016/012532 2015-11-03 2016-11-02 A plurality of host materials and organic electroluminescent device comprising the same Ceased WO2017078403A1 (en)

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018008718A1 (en) * 2016-07-07 2018-01-11 保土谷化学工業株式会社 Compound having benzazole ring structure and organic electroluminescent element
CN108976212A (en) * 2017-06-02 2018-12-11 北京鼎材科技有限公司 Fluorene derivative and its application in luminous organic material
WO2019059695A1 (en) 2017-09-22 2019-03-28 Rohm And Haas Electronic Materials Korea Ltd. A plurality of host materials and organic electroluminescent device comprising the same
CN111149229A (en) * 2017-09-22 2020-05-12 罗门哈斯电子材料韩国有限公司 Multiple host materials and organic electroluminescent device comprising the same
CN112300171A (en) * 2019-07-30 2021-02-02 江苏三月光电科技有限公司 A kind of organic compound based on carbazolo ring structure and its application in OLED
CN112939985A (en) * 2021-01-22 2021-06-11 陕西莱特光电材料股份有限公司 Organic compound, and electronic element and electronic device using same
CN113582997A (en) * 2021-06-18 2021-11-02 陕西莱特迈思光电材料有限公司 Nitrogen-containing compound, electronic component, and electronic device
CN114105997A (en) * 2021-01-28 2022-03-01 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, electronic element comprising same and electronic device
CN114539270A (en) * 2021-12-09 2022-05-27 上海钥熠电子科技有限公司 Compound containing carbazole derivative and application thereof in organic electroluminescent device
WO2022217791A1 (en) * 2021-04-13 2022-10-20 陕西莱特光电材料股份有限公司 Composition, and electronic element and electronic apparatus comprising same

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110011579A (en) * 2009-07-27 2011-02-08 에스에프씨 주식회사 Indolocarbazole derivatives and organic electroluminescent devices using the same
US20150318510A1 (en) * 2014-05-02 2015-11-05 Samsung Display Co., Ltd. Organic light-emitting device
KR20150136033A (en) * 2014-05-26 2015-12-04 주식회사 엘지화학 Nitrogen-containing heterocyclic compounds and organic electronic device using the same
US20160118590A1 (en) * 2014-09-24 2016-04-28 Samsung Display Co., Ltd. Organic light-emitting devices

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110011579A (en) * 2009-07-27 2011-02-08 에스에프씨 주식회사 Indolocarbazole derivatives and organic electroluminescent devices using the same
US20150318510A1 (en) * 2014-05-02 2015-11-05 Samsung Display Co., Ltd. Organic light-emitting device
KR20150136033A (en) * 2014-05-26 2015-12-04 주식회사 엘지화학 Nitrogen-containing heterocyclic compounds and organic electronic device using the same
US20160118590A1 (en) * 2014-09-24 2016-04-28 Samsung Display Co., Ltd. Organic light-emitting devices

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12317744B2 (en) 2016-07-07 2025-05-27 Hodogaya Chemical Co., Ltd. Compound having a fused-azole ring structure and organic electroluminescent element
WO2018008718A1 (en) * 2016-07-07 2018-01-11 保土谷化学工業株式会社 Compound having benzazole ring structure and organic electroluminescent element
JPWO2018008718A1 (en) * 2016-07-07 2019-04-18 保土谷化学工業株式会社 Compound having benzoazole ring structure and organic electroluminescent device
CN108976212A (en) * 2017-06-02 2018-12-11 北京鼎材科技有限公司 Fluorene derivative and its application in luminous organic material
CN111149229B (en) * 2017-09-22 2024-04-26 罗门哈斯电子材料韩国有限公司 Various host materials and organic electroluminescent devices containing the same
CN111149229A (en) * 2017-09-22 2020-05-12 罗门哈斯电子材料韩国有限公司 Multiple host materials and organic electroluminescent device comprising the same
EP3685453A4 (en) * 2017-09-22 2022-01-12 Rohm And Haas Electronic Materials Korea Ltd. PLURALITY OF HOST MATERIALS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THEM
WO2019059695A1 (en) 2017-09-22 2019-03-28 Rohm And Haas Electronic Materials Korea Ltd. A plurality of host materials and organic electroluminescent device comprising the same
US11856850B2 (en) 2017-09-22 2023-12-26 Rohm And Haas Electronic Materials Korea Ltd. Plurality of host materials and organic electroluminescent device comprising the same
CN112300171A (en) * 2019-07-30 2021-02-02 江苏三月光电科技有限公司 A kind of organic compound based on carbazolo ring structure and its application in OLED
CN112300171B (en) * 2019-07-30 2023-08-15 江苏三月科技股份有限公司 Organic compound based on carbazolo ring structure and application of organic compound to OLED
CN112939985A (en) * 2021-01-22 2021-06-11 陕西莱特光电材料股份有限公司 Organic compound, and electronic element and electronic device using same
US11723271B2 (en) 2021-01-22 2023-08-08 Shaanxi Lighte Optoelectronics Material Co., Ltd. Organic compound, and electronic component and electronic device therefor
JP7307515B2 (en) 2021-01-28 2023-07-12 シャンシー ライト オプトエレクトロニクス マテリアル カンパニー リミテッド Nitrogen-containing compound, electronic element containing same, and electronic device
US11618754B2 (en) 2021-01-28 2023-04-04 Shaanxi Lighte Optoelectronics Material Co., Ltd. Nitrogen-containing compound, electronic component and electronic device including same
JP2023510445A (en) * 2021-01-28 2023-03-14 シャンシー ライト オプトエレクトロニクス マテリアル カンパニー リミテッド Nitrogen-containing compound, electronic element containing same, and electronic device
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