WO2019245164A1 - Pluralité de matériaux hôtes et dispositif électroluminescent organique les comprenant - Google Patents

Pluralité de matériaux hôtes et dispositif électroluminescent organique les comprenant Download PDF

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Publication number
WO2019245164A1
WO2019245164A1 PCT/KR2019/005686 KR2019005686W WO2019245164A1 WO 2019245164 A1 WO2019245164 A1 WO 2019245164A1 KR 2019005686 W KR2019005686 W KR 2019005686W WO 2019245164 A1 WO2019245164 A1 WO 2019245164A1
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Prior art keywords
substituted
unsubstituted
alkyl
membered
arylsilyl
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PCT/KR2019/005686
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English (en)
Inventor
Bitnari Kim
Su-Hyun Lee
Hyo-Soon Park
Tae-Jun Han
Jeong-Eun YANG
Sang-Hee Cho
Doo-Hyeon Moon
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020190045304A external-priority patent/KR20200000329A/ko
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to US16/972,948 priority Critical patent/US20210336153A1/en
Priority to JP2020571491A priority patent/JP7340548B2/ja
Priority to DE112019002522.8T priority patent/DE112019002522T5/de
Priority to CN201980041619.8A priority patent/CN112313811A/zh
Publication of WO2019245164A1 publication Critical patent/WO2019245164A1/fr
Priority to JP2023019480A priority patent/JP2023053167A/ja
Priority to US18/430,070 priority patent/US20240188432A1/en

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/90—Multiple hosts in the emissive layer
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present disclosure relates to a plurality of host materials and an organic electroluminescent device comprising the same.
  • OLED organic electroluminescent device
  • TPD/Alq3 bilayer consisting of a light-emitting layer and a charge transport layer. Since then, the research on an OLED has been rapidly carried out, and it has been commercialized. At present, OLEDs primarily use phosphorescent materials having excellent luminous efficiency in panel implementation. In addition, an OLED having high luminous efficiency and/or long lifespan is required for prolonged use and high resolution of a display.
  • Korean Patent Appl. Laid-Open No. 2017-0022865 discloses a benzoxazole derivative compound for improving the performance of an OLED. However, the development of materials for improving the performance of an OLED is still required.
  • the objective of the present disclosure is to provide a plurality of host materials comprising a specific combination of compounds, suitable for producing an organic electroluminescent device having higher luminous efficiency and/or longer lifespan properties.
  • the present inventors found that the above objective can be achieved by a plurality of host materials comprising a first host material and a second host material, wherein the first host material comprises a compound represented by the following formula 1, and the second host material comprises a compound represented by the following formula 2:
  • Ar represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least one of nitrogen, oxygen, and sulfur;
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
  • X 1 to X 8 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, a substituted or unsubstituted (3- to 30-membered)heteroaryl, -NR 5 R 6 , or -SiR 7 R 8 R 9 ; or adjacent ones of X 1 to X 8 may be linked to each other to form a ring(s); with the proviso that at least one pair of X 1
  • R 5 to R 9 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; or adjacent ones of R 5 to R 9 may be linked to each other to form a ring(s); and
  • HAr represents a substituted or unsubstituted (3- to 30-membered)heteroaryl containing a nitrogen atom(s);
  • L 2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
  • R 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
  • R 2 to R 4 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6
  • R 10 and R 11 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6
  • a' represents an integer of 1; b' and c', each independently, represent an integer of 1 or 2; d' represents an integer of 1 to 4; where if b', c', and d', each independently, are an integer of 2 or more, each of R 2 to R 4 may be the same or different.
  • organic electroluminescent material in the present disclosure means a material that may be used in an organic electroluminescent device, and may comprise at least one compound.
  • the organic electroluminescent material may be comprised in any layer constituting an organic electroluminescent device, as necessary.
  • the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material (containing host and dopant materials), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.
  • a plurality of organic electroluminescent materials in the present disclosure means an organic electroluminescent material as a combination of at least two compounds, which may be comprised in any layer constituting an organic electroluminescent device. It may mean both a material before being comprised in an organic electroluminescent device (for example, before vapor deposition) and a material after being comprised in an organic electroluminescent device (for example, after vapor deposition).
  • a plurality of organic electroluminescent materials may be a combination of at least two compounds which may be comprised in at least one of 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, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
  • At least two compounds may be comprised in the same layer or different layers by means of the methods used in the art, for example, may be mixture-evaporated or co-evaporated, or may be individually evaporated.
  • a plurality of host materials in the present disclosure means an organic electroluminescent material as a combination of at least two host materials. It may mean both a material before being comprised in an organic electroluminescent device (for example, before vapor deposition) and a material after being comprised in an organic electroluminescent device (for example, after vapor deposition).
  • a plurality of host materials of the present disclosure may be comprised in any light-emitting layer constituting an organic electroluminescent device. At least two compounds comprised in a plurality of host materials may be comprised together in one light-emitting layer or may respectively be comprised in different light-emitting layers. If at least two host materials are comprised in one layer, for example, they may be mixture-evaporated to form a layer, or may be separately co-evaporated at the same time to form a layer.
  • (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 10, and more preferably 1 to 6.
  • the above alkyl may include methyl, ethyl, n -propyl, iso -propyl, n -butyl, iso -butyl, tert -butyl, etc.
  • (C3-C30)cycloalkyl is meant to be 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, and more preferably 3 to 7.
  • the above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • the term "(3- to 7-membered)heterocycloalkyl” is meant to be a cycloalkyl having 3 to 7 ring backbone atoms, and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably the group consisting of O, S, and N.
  • the above heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
  • (C6-C30)aryl or "(C6-C30)arylene” is meant to be a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of the ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15.
  • the above aryl or arylene may be partially saturated, and may comprise a spiro structure.
  • the above aryl may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, spiro[fluorene-benzofluorene]yl, etc.
  • (3- to 50-membered)heteroaryl or "(3- to 30-membered)heteroarylene” is an aryl having 3 to 50, or 3 to 30 ring backbone atoms, in which the number of the ring backbone carbon atoms is preferably 3 to 30, more preferably 5 to 20, and 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(ene) 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 may comprise a spiro structure.
  • the above heteroaryl may include 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, benzonaphthofuranyl, dibenzothiophenyl, benzonaphthothiophenyl, benzimidazolyl, benzothiazolyl, benzoiso
  • 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 are at least one selected from the group consisting of a (C1-C20)alkyl; a (C6-C25)aryl unsubstitued or substituted with at least one of a (C1-C20)alkyl(s), a (3- to 30-membered)heteroaryl(s), and a di(C6-C25)arylamino(s); a (3- to 30-membered)heteroaryl unsubstituted or substituted with at least one of a (C1-C20)alkyl(s) and a (C6-C25)aryl(s); and a di(C6-C20)arylamino.
  • the substituents are at least one selected from the group consisting of a (C1-C10)alkyl; a (C6-C20)aryl unsubstitued or substituted with at least one of a (C1-C10)alkyl(s) and a di(C6-C18)arylamino(s); a (5- to 25-membered)heteroaryl unsubstituted or substituted with a (C6-C18)aryl(s); and a di(C6-C18)arylamino.
  • the substituents are at least one methyl; tert -butyl; phenyl unsubstituted or substituted with at least one of pyridinyl, diphenyltriazinyl, phenylquinoxalinyl, phenylquinazolinyl, biphenylquinazolinyl, dibenzofuranyl, dibenzothiophenyl and diphenylamino; naphthyl unsubstituted or substituted with at least one diphenyltriazinyl; biphenyl; naphthylphenyl; terphenyl; dimethylfluorenyl; phenylfluorenyl; diphenylfluorenyl; dimethylbenzofluorenyl; phenanthrenyl; triphenylenyl; pyridinyl; triazinyl substituted with at least one of phenyl and naphthyl; indoly
  • adjacent ones may be linked to each other to form a ring(s)
  • a ring(s) means that at least two adjacent substituents are linked to or fused with each other to form a substituted or unsubstituted mono- or polycyclic (3- to 30-membered), preferably (3- to 26-membered), alicyclic or aromatic ring, or the combination thereof.
  • the formed ring may contain at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S.
  • the heteroaryl, the heteroarylene, and the heterocycloalkyl may contain at least one heteroatom selected from B, N, O, S, Si, and P.
  • the heteroatom may be bonded to at least one selected from the group consisting of hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)ary
  • Ar represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least one of nitrogen, oxygen, and sulfur.
  • Ar represents a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl containing at least one of nitrogen, oxygen, and sulfur.
  • Ar represents a (C6-C18)aryl unsubstituted or substituted with a (C1-C30)alkyl(s), or a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C6-C18)aryl(s) and containing nitrogen, oxygen or sulfur.
  • Ar represents a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzothiophenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted benzonaphtho
  • Ar may represent phenyl, naphthyl, biphenyl, terphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl unsubstituted or substituted with a phenyl(s), or benzonaphthofuranyl.
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene.
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5- to 25-membered)heteroarylene.
  • L 1 represents a single bond, an unsubstituted (C6-C18)arylene, or an unsubstituted (5- to 20-membered)heteroarylene.
  • L 1 may represent a single bond, phenylene, naphthylene, biphenylene, or phenanthroxazolylene.
  • X 1 to X 8 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, a substituted or unsubstituted (3- to 30-membered)heteroaryl, -NR 5 R 6 , or -SiR 7 R 8 R 9 ; or adjacent ones of X 1 to X 8 may be linked to each other to form a ring(s); with the proviso that at least one pair of
  • X 1 to X 8 each independently, represent hydrogen; or at least one pair of X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 4 and X 5 , X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 is linked to each other to form a ring(s), in which the ring has 1 to 5 monocyclic rings, preferably, 2 to 5 monocyclic rings.
  • X 1 and X 2 are linked to each other to form an indole ring, in which the ring has 2 monocyclic rings.
  • the ring may be a substituted or unsubstituted mono- or polycyclic (3- to 30-membered) alicyclic or aromatic ring, or a combination thereof; preferably a substituted or unsubstituted mono- or polycyclic (3- to 20-membered) alicyclic or aromatic ring, or the combination thereof; and more preferably a substituted or unsubstituted monocyclic (3- to 8- membered) aromatic ring.
  • the ring may be one in which 1 to 5 monocyclic rings, preferably 2 to 5 monocyclic rings, are fused.
  • the ring may contain at least one heteroatom selected from B, N, O, S, Si and P; preferably, at least one heteroatom selected from N, O, and S; and more preferably, at least one heteroatom selected from N and S.
  • the compound represented by formula 1 may be a fused carbazole-based compound, a fused azulene-based compound, etc.
  • X 1 to X 8 each independently, represent hydrogen; or may be linked to an adjacent substituent(s) to form a benzene ring, an indole ring substituted with a phenyl(s) and/or a biphenyl(s), a benzothiophene ring, a benzoindole ring substituted with at least one of a phenyl(s) and a naphthyl(s), a 15-membered polycyclic ring, a nitrogen-containing 18-membered polycyclic ring, or a nitrogen-containing 22-membered polycyclic ring.
  • R 5 to R 9 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; or adjacent ones of R 5 to R 9 may be linked to each other to form a ring(s).
  • the formula 1 may be represented by any one of the following formulas 1-1 to 1-10.
  • Ar and L 1 are as defined in formula 1.
  • V and W each independently, represent CR 12 R 13 , NR 14 , O, or S.
  • V and W each independently, represent NR 14 , O, or S.
  • V may represent NR 14 or S
  • W may represent S.
  • R 12 to R 14 , X 11 to X 23 , and X 31 to X 33 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)aryl
  • R 12 to R 14 each independently, represent a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl.
  • R 12 to R 14 each independently, represent an unsubstituted (C6-C18)aryl.
  • R 12 to R 14 each independently, may represent phenyl or biphenyl.
  • X 11 to X 23 , and X 31 to X 33 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl.
  • X 11 to X 23 , and X 31 to X 33 each independently, represent hydrogen, deuterium, or an unsubstituted (C6-C18)aryl.
  • X 11 to X 23 , and X 31 to X 33 each independently, may represent hydrogen or phenyl.
  • X 24 to X 30 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(
  • X 24 to X 30 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl; or adjacent ones of X 24 to X 30 may be linked to each other to form a ring(s).
  • X 24 to X 30 each independently, represent hydrogen, deuterium, or an unsubstituted (C6-C18)aryl; or adjacent ones of X 24 to X 30 may be linked to each other to form a ring(s).
  • X 24 to X 30 each independently, represent hydrogen; or adjacent ones of X 24 to X 30 may be linked to each other to form a benzene ring.
  • a, e to i, k, l, o, p, s, u, y, and z each independently, represent an integer of 1 to 4; b to d, j, and m, each independently, represent an integer of 1 to 6; n and r, each independently, represent an integer of 1 to 3; q represents an integer of 1 or 2; t represents an integer of 1 to 5; where a to u, y, and z, each independently, are an integer of 2 or more, each of X 11 to X 33 may be the same or different.
  • R 10 and R 11 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6
  • R 10 and R 11 each independently, represent a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl.
  • R 10 and R 11 each independently, represent an unsubstituted (C6-C18)aryl.
  • R 10 and R 11 may be a phenyl.
  • HAr represents a substituted or unsubstituted (3- to 30-membered)heteroaryl containing a nitrogen atom(s). According to one embodiment of the present disclosure, HAr represents a substituted or unsubstituted (5- to 25-membered)heteroaryl containing a nitrogen atom(s). According to another embodiment of the present disclosure, HAr represents a (5- to 20-membered)heteroaryl containing a nitrogen atom(s), unsubstituted or substituted with a (5- to 25-membered)heteroaryl(s) and/or a (C6-C25)aryl(s).
  • HAr represents a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted benzoquinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted benzoisoquinolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted naphthy
  • HAr may represent a substituted triazinyl, a substituted pyrimidinyl, a substituted quinoxalinyl, a substituted quinazolinyl, or a substituted naphthyridinyl.
  • the substituent of the substituted triazinyl, the substituted pyrimidinyl, the substituted quinoxalinyl, the substituted quinazolinyl, and the substituted naphthyridinyl may be at least one of phenyl unsubstituted or substituted with a diphenylamino(s), naphthyl, biphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, dibenzothiophenyl, dibenzofuranyl, benzonaphthothiophenyl, phenylcarbazolyl, and phenylbenzocarbazolyl.
  • L 2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene.
  • L 2 represents a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5- to 25-membered)heteroarylene.
  • L 2 represents a single bond, an unsubstituted (C6-C18)arylene, or an unsubstituted (5- to 20-membered)heteroarylene.
  • L 2 may represent a single bond, phenylene, or pyridylene.
  • R 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl. According to one embodiment of the present disclosure, R 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl.
  • R 1 represents a (C6-C29)aryl unsubstituted or substituted with a (C1-C10)alkyl(s) and/or a (C6-C18)aryl(s); or a (5- to 25-membered)heteroaryl unsubstituted or substituted with a (C6-C18)aryl(s).
  • R 1 may be phenyl, naphthyl, phenylnaphthyl, biphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, spirobifluorenyl, spiro[fluorene-benzofluorene]yl, phenylcarbazolyl, phenylbenzocarbazolyl, dibenzofuranyl, or dibenzothiophenyl.
  • R 2 to R 4 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri
  • a' represents an integer of 1
  • b' and c' each independently, represent an integer of 1 or 2
  • d' represents an integer of 1 to 4
  • b', c', and d' each independently, are an integer of 2 or more, each of R 2 to R 4 may be the same or different.
  • the formula 2 may be represented by any one of the following formulas 2-1 and 2-2.
  • Y 1 to Y 5 , and Y 11 to Y 17 each independently, represent N or CR 15 . According to one embodiment of the present disclosure, at least one of Y 1 to Y 5 represents CR 15 , and at least one of Y 11 to Y 17 represents CR 15 .
  • R 15 each independently, represents hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30
  • R 15 each independently, represents hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl.
  • R 15 each independently, represents hydrogen; deuterium; a (C6-C18)aryl unsubstituted or substituted with a (C1-C10)alkyl(s) and/or a di(C6-C18)arylamino(s); or a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C6-C18)aryl(s).
  • R 15 may represent hydrogen, phenyl unsubstituted or substituted with a diphenylamino(s), naphthyl, biphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, dibenzothiophenyl, dibenzofuranyl, benzonaphthothiophenyl, phenylcarbazolyl, or phenylbenzocarbazolyl.
  • the compound represented by formula 1 includes the following compounds, but is not limited thereto.
  • the compound represented by formula 2 includes the following compounds, but is not limited thereto.
  • the combination of at least one of compounds C1-1 to C1-94 and at least one of compounds C2-1 to C2-125 may be used in an organic electroluminescent device.
  • the compound represented by formula 1 according to the present disclosure may be prepared by a synthetic method known to one skilled in the art.
  • the compound represented by formula 1 can be prepared by referring to the following reaction scheme 1, and Korean Patent Appl.
  • Laid-Open Nos. 2015-0135109 A published on December 2, 2015
  • 2015-0032447 A published on March 26, 2015
  • 2016-0099471 A published on August 22, 2016
  • 2018-0012709 A published on February 6, 2018
  • 2012-0132815 A published on December 10, 2012
  • 2015-0077513 A published on July 8, 2015
  • 2017-0129599 A published on November 27, 2017
  • Korean Patent No. 1478990 B Korean Patent No. 1478990 B (published on December 29, 2014), but is not limited thereto.
  • the compound represented by formula 2 according to the present disclosure may be prepared by a synthetic method known to one skilled in the art.
  • the compound represented by formula 2 can be prepared by referring to Korean Patent Appl. Laid-Open No. 2017-0022865 A (published on March 2, 2017), but is not limited thereto.
  • the organic electroluminescent device comprises an anode, a cathode, and at least one organic layer between the anode and the cathode.
  • the organic layer may comprise a plurality of organic electroluminescent materials in which the compound represented by formula 1 is included as a first organic electroluminescent material, and the compound represented by formula 2 is included as a second organic electroluminescent material.
  • the organic electroluminescent device comprises an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, and at least one layer of the at least one light-emitting layer may comprise the compound represented by formula 1 and the compound represented by formula 2.
  • the light-emitting layer comprises a host and a dopant.
  • the host comprises a plurality of host materials.
  • the compound represented by formula 1 may be comprised as a first host compound in a plurality of host materials
  • the compound represented by formula 2 may be comprised as a second host compound in a plurality of host materials.
  • the weight ratio of the first host compound to the second host compound is in the range of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, even more preferably about 40:60 to 60:40, and still more preferably about 50:50.
  • the light-emitting layer is a layer from which light is emitted, and can be a single layer or a multi-layer in which two or more layers are stacked.
  • the first and second host materials may both be comprised in one layer, or may be respectively comprised in different light-emitting layers.
  • the doping concentration of the dopant compound with respect to the host compound in the light-emitting layer is less than 20 wt%.
  • the organic electroluminescent device of the present disclosure 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 injection layer, an interlayer, an electron buffer layer, a hole blocking layer, and an electron blocking layer.
  • the organic electroluminescent device may further comprise amine-based compounds in addition to a plurality of host materials of the present disclosure as at least one of a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting material, a light-emitting auxiliary material and an electron blocking material.
  • the organic electroluminescent device may further comprise azine-based compounds in addition to a plurality of host materials of the present disclosure as at least one of an electron transport material, an electron injection material, an electron buffer material and a hole blocking material.
  • the dopant comprised in the organic electroluminescent device of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant.
  • the phosphorescent dopant material 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 compound comprised in the organic electroluminescent device of the present discloasure may comprise the compound represented by the following formula 101, but is not limited thereto.
  • L is selected from the following structures 1 and 2:
  • R 100 to R 103 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with deuterium and/or a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a cyano, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C1-C30)alkoxy; or may be linked to adjacent R 100 to R 103 , to form a ring(s) together with pyridine, e.g., a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstit
  • R 104 to R 107 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with deuterium and/or a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a cyano, or a substituted or unsubstituted (C1-C30)alkoxy; or may be linked to adjacent R 104 to R 107 to form a ring(s) together with benzene, e.g., a substituted or unsubstituted naphthalene, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubsti
  • R 201 to R 211 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with deuterium and/or a halogen(s), a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; or may be linked to adjacent R 201 to R 211 to form a ring; and
  • n' represents an integer of 1 to 3.
  • dopant compound is as follows, but are not limited thereto.
  • dry film-forming methods such as vacuum evaporation, sputtering, plasma, and ion plating methods, or wet film-forming methods such as ink jet printing, nozzle printing, slot coating, 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.
  • the compound represented by formula 1, and the compound represented by formula 2 may be film-formed in the above-listed methods, commonly by a co-evaporation process or a mixture-evaporation process.
  • the co-evaporation is a mixed deposition method in which two or more materials are placed in a respective individual crucible source and an electric current is applied to both cells at the same time to evaporate the materials.
  • the mixture-evaporation is a mixed deposition method in which two or more materials are mixed in one crucible source before evaporating them, and an electric current is applied to the cell to evaporate the materials.
  • the present disclosure may provide a display system by comprising a plurality of host materials.
  • a display system or a lighting system by using the organic electroluminent device of the present disclosure.
  • a display system e.g., a display system for smartphones, tablets, notebooks, PCs, TVs, or cars, or a lighting system, e.g., an outdoor or indoor lighting system, by using the plurality of host materials of the present disclosure.
  • An OLED according to the present disclosure was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol.
  • the ITO substrate was 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 then controlled to 10 -6 torr.
  • compound HI-2 was 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 injection layer having a thickness of 5 nm on the first hole injection layer.
  • 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 10 nm on the second 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 60 nm on the first hole transport layer.
  • a light-emitting layer was formed thereon as follows: The first host and the second host compounds shown in Table 1 were introduced into two cells of the vacuum vapor depositing apparatus, respectively, as hosts and compound D-39 was introduced into another cell as a dopant.
  • the two host materials were evaporated at a rate of 1:1, and at the same time the dopent material was evaporated at different rates to be deposited in a doping amount of 3 wt% based on the total amount of the hosts and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
  • compound ET-1 and compound EI-1 were evaporated at a rate of 1:1 in two other cells to deposit an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus.
  • an OLED was produced.
  • An OLED was produced in the same manner as in Device Example 2, except that the first host compound and the second host compound described in Table 1 were deposited in one cell rather than in two cells in a vacuum deposition apparatus.
  • An OLED was produced in the same manner as in Device Example 2, except that compound D-78 was used as a dopant instead of compound D-39 .
  • An OLED was produced in the same manner as in Device Example 1, except that only the second host compound described in Table 1 below was used instead of the two hosts.
  • an organic electroluminescent device comprising a specific combination of compounds according to the present disclosure as host materials has higher luminous efficiency and/or longer lifespan properties as compared with the conventional organic electroluminescent device.

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

Abstract

La présente invention concerne une pluralité de matériaux hôtes comprenant un premier matériau hôte ayant un composé représenté par la formule 1 et un second matériau hôte ayant un composé représenté par la formule 2, et un dispositif électroluminescent organique les comprenant. En comprenant une combinaison spécifique de composés de la présente invention en tant que matériaux hôtes, il est possible de fournir un dispositif électroluminescent organique ayant une efficacité lumineuse supérieure et/ou des propriétés de durée de vie plus longues par comparaison avec un dispositif électroluminescent organique classique.
PCT/KR2019/005686 2018-06-22 2019-05-13 Pluralité de matériaux hôtes et dispositif électroluminescent organique les comprenant WO2019245164A1 (fr)

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US16/972,948 US20210336153A1 (en) 2018-06-22 2019-05-13 Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same
JP2020571491A JP7340548B2 (ja) 2018-06-22 2019-05-13 複数のホスト材料及びこれを含む有機エレクトロルミネセンスデバイス
DE112019002522.8T DE112019002522T5 (de) 2018-06-22 2019-05-13 Mehrere Wirtsmaterialien und diese umfassende organische elektrolumineszierende Vorrichtung
CN201980041619.8A CN112313811A (zh) 2018-06-22 2019-05-13 多种主体材料及包含其的有机电致发光装置
JP2023019480A JP2023053167A (ja) 2018-06-22 2023-02-10 複数のホスト材料及びこれを含む有機エレクトロルミネセンスデバイス
US18/430,070 US20240188432A1 (en) 2018-06-22 2024-02-01 Plurality of host materials and organic electroluminescent device comprising the same

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KR20180072267 2018-06-22
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CN113444096A (zh) * 2020-03-26 2021-09-28 罗门哈斯电子材料韩国有限公司 多种主体材料以及包含其的有机电致发光装置
CN115703782A (zh) * 2021-08-05 2023-02-17 德山新勒克斯有限公司 用于有机电子元件的化合物、使用所述化合物的有机电子元件及其电子装置
JP2023510445A (ja) * 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 窒素含有化合物、それを含む電子素子、及び電子装置
WO2024121133A1 (fr) 2022-12-08 2024-06-13 Merck Patent Gmbh Dispositif électronique organique et matériaux spéciaux pour dispositifs électroniques organiques
WO2024132993A1 (fr) 2022-12-19 2024-06-27 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2024194264A1 (fr) 2023-03-20 2024-09-26 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques

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CN115703782A (zh) * 2021-08-05 2023-02-17 德山新勒克斯有限公司 用于有机电子元件的化合物、使用所述化合物的有机电子元件及其电子装置
CN115703782B (zh) * 2021-08-05 2024-04-19 德山新勒克斯有限公司 用于有机电子元件的化合物、使用所述化合物的有机电子元件及其电子装置
WO2024121133A1 (fr) 2022-12-08 2024-06-13 Merck Patent Gmbh Dispositif électronique organique et matériaux spéciaux pour dispositifs électroniques organiques
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