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WO2018182221A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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Publication number
WO2018182221A1
WO2018182221A1 PCT/KR2018/003245 KR2018003245W WO2018182221A1 WO 2018182221 A1 WO2018182221 A1 WO 2018182221A1 KR 2018003245 W KR2018003245 W KR 2018003245W WO 2018182221 A1 WO2018182221 A1 WO 2018182221A1
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Prior art keywords
substituted
unsubstituted
independently
membered
aryl
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Inventor
Tae-Jin Lee
Dong-Hyung Lee
Bitnari Kim
Hong-Se OH
Hee-Ryong Kang
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DuPont Specialty Materials Korea Ltd
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Rohm and Haas Electronic Materials Korea Ltd
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Priority claimed from KR1020180029725A external-priority patent/KR102672462B1/ko
Application filed by Rohm and Haas Electronic Materials Korea Ltd filed Critical Rohm and Haas Electronic Materials Korea Ltd
Priority to US16/492,647 priority Critical patent/US20210328152A1/en
Priority to CN201880017462.0A priority patent/CN110392941B/zh
Priority to JP2019552268A priority patent/JP2020516058A/ja
Publication of WO2018182221A1 publication Critical patent/WO2018182221A1/fr
Anticipated expiration legal-status Critical
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/40—Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/156—Hole transporting layers comprising a multilayered structure
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    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present disclosure relates to an organic electroluminescent device comprising a light-emitting layer and a hole transport zone.
  • the first low molecular green organic electroluminescent device was developed by Tang, et al., of Eastman Kodak in 1987 by using TPD/ALq3 bi-layer consisting of a light-emitting layer and a charge transport layer. Thereafter, the development of organic electroluminescent devices was rapidly effected and the devices were currently commercialized. Current organic electroluminescent devices mostly use phosphorescent materials with excellent luminous efficiency for panel manufacture. For long-term use and high resolution of the display, a low driving voltage and high luminous efficiency are required.
  • Korean Patent Application Laid-Open No. 2015-0071685 discloses an organic electroluminescent device comprising a compound comprising a carbazole and a nitrogen-containing 10-membered hereroaryl, as a host.
  • said reference does not specifically disclose a benzoindolocarbazole derivative, nor that the performance of an organic electroluminescent device can be improved by combining a host compound having a carbazole, and a specific material comprised in a hole transport zone.
  • the objective of the present disclosure is to provide an organic electroluminescent device having excellent luminous efficiency while maintaining excellent lifespan and/or driving voltage characteristics, by combining a light-emitting layer comprising a compound of the present disclosure, and a hole transport zone comprising a compound having a specific HOMO (Highest Occupied Molecular Orbital) energy level.
  • a light-emitting layer comprising a compound of the present disclosure
  • a hole transport zone comprising a compound having a specific HOMO (Highest Occupied Molecular Orbital) energy level.
  • the conventional hole transport zone has limitations in improving the efficiency of a light-emitting layer.
  • the hole transport zone requires a compound having a high HOMO energy level for fast hole mobility. If the compound has a high HOMO energy level, the driving voltage decreases, but the efficiency of a light-emitting layer also decreases. In contrast, if the compound has a low HOMO energy level, the efficiency of a light-emitting layer increases, but the driving voltage also increases, which makes it difficult to achieve a high luminous efficiency of a device.
  • an organic electroluminescent device comprising a first electrode, a second electrode facing the first electrode, a light-emitting layer between the first electrode and the second electrode, and a hole transport zone between the first electrode and the light-emitting layer, wherein the light-emitting layer comprises a compound represented by the following formula 1:
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene,
  • X 1 to X 6 each independently, represent N or CR c , with a proviso that at least one of X 1 to X 6 represents N,
  • Ar represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl,
  • R a to R c each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR f R g , -SiR h R i R j , -SR k , -OR l , a cyano, a nitro, or a hydroxyl, with a proviso that adjacent two R a ’s or adjacent two R b
  • R f to R l each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (3- to 30-membered) alicyclic or aromatic ring, or a combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur,
  • each independently represent an integer of 1 to 4, in which if p and q, each independently, are an integer of 2 or more, each of R a and R b may be the same or different, and
  • the heteroaryl(ene) or the heterocycloalkyl contains at least one heteroatom selected from B, N, O, S, Si, and P;
  • the hole transport zone comprises an arylamine derivative containing a fluorene or a fused fluorene, and the HOMO energy level of the arylamine derivative satisfies the following equation 11:
  • the present disclosure provides an organic electroluminescent device having improved luminous efficiency, while maintaining excellent lifespan and/or driving voltage characteristics.
  • the present disclosure also provides a display system or a lighting system using the same.
  • the organic electroluminescent device of the present disclosure may comprise a first electrode, a second electrode facing the first electrode, a light-emitting layer between the first electrode and the second electrode, a hole transport zone between the first electrode and the light-emitting layer, and an electron transport zone between the light-emitting layer and the second electrode.
  • One of the first and second electrodes may be an anode, and the other may be a cathode.
  • the hole transport zone means an area in which holes move between the first electrode and the light-emitting layer, and may comprise, for example, at least one of a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer.
  • the hole injection layer, the hole transport layer, the hole auxiliary layer, the light-emitting auxiliary layer, and the electron blocking layer may be, respectively, a single layer or a multi-layer in which two or more layers are stacked.
  • the hole transport zone may comprise a first hole transport layer and a second hole transport layer.
  • the second hole transport layer may be at least one layer of a plurality of hole transport layers, and may comprise at least one of a hole auxiliary layer, a light-emitting auxiliary layer, and an electron blocking layer.
  • the hole transport zone comprises a first hole transport layer and a second hole transport layer, in which the first hole transport layer may be placed between the first electrode and the light-emitting layer, the second hole transport layer may be placed between the first hole transport layer and the light-emitting layer, and the second hole transport layer may play a role as a hole transport layer, a light-emitting auxiliary layer, a hole auxiliary layer and/or an electron blocking layer.
  • the hole transport layer may be placed between the anode (or the hole injection layer) and the light-emitting layer, enables holes transferred from the anode to smoothly move to the light-emitting layer, and may block the electrons transferred from the cathode to confine electrons within the light-emitting layer.
  • the light-emitting auxiliary layer may be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it can be used for promoting the hole injection and/or hole transport, or for preventing the overflow of electrons.
  • the light-emitting auxiliary layer When the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it can be used for promoting the electron injection and/or electron transport, or for preventing the overflow of holes.
  • the hole auxiliary layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may be effective to promote or block the hole transport rate (or hole injection rate), thereby enabling the charge balance to be controlled.
  • the electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can confine the excitons within the light-emitting layer by blocking the overflow of electrons from the light-emitting layer to prevent a light-emitting leakage.
  • the hole transport layer When an organic electroluminescent device includes two or more hole transport layers, the hole transport layer, which is further included, may be used as a hole auxiliary layer or an electron blocking layer.
  • the light-emitting auxiliary layer, the hole auxiliary layer and/or the electron blocking layer may have an effect of improving the efficiency and/or the lifespan of the organic electroluminescent device.
  • the electron transport zone may comprise at least one of an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer, preferably at least one of an electron transport layer and an electron injection layer.
  • the electron buffer layer is a layer capable of improving the problem that the current characteristics in the device changes upon exposure to a high temperature in a panel fabrication process to cause deformation of light emission luminance, which can control the flow of charge.
  • the light-emitting layer emits light, and may be a single layer, or a plurality of layers in which two or more layers are stacked.
  • the doping concentration of the dopant compound with respect to the host compound in the light-emitting layer is preferably less than 20 wt%.
  • the organic electroluminescent device according to the present disclosure comprises the compound represented by formula 1 in the light-emitting layer.
  • L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (5- to 30-membered)heteroarylene; preferably, a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5- to 25-membered)heteroarylene; more preferably, a single bond, a substituted or unsubstituted (C6-C18)arylene, or a substituted or unsubstituted (5- to 18-membered)heteroarylene; and, for example, a single bond, an unsubstituted phenylene, an unsubstituted naphthylene, or an unsubstituted pyridinylene.
  • X 1 to X 6 each independently, represent N or CR c , with a proviso that at least one of X 1 to X 6 represents N. According to one embodiment of the present disclosure, at least one of X 1 and X 6 may represent N, and X 2 to X 5 may represent CR c .
  • the structure of may represent a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted pyridopyrimidinyl, or a substituted or unsubstituted pyridopyrazinyl; preferably, a substituted or unsubstituted quinoxalinyl, or a substituted or unsubstituted quinazolinyl, and wherein, * represents a bonding site with L 1 .
  • Ar represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; preferably, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl; more preferably, a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted (5- to 18-membered)heteroaryl; and for example, an unsubstituted phenyl, an unsubstituted naphthyl, an unsubstituted biphenyl, a fluorenyl substituted with a dimethyl, an unsubstituted phenanthrenyl, or an unsubstituted pyridinyl.
  • R a to R c each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR f R g , -SiR h R i R j , -SR k , -OR l , a cyano, a nitro, or a hydroxyl; preferably, hydrogen, or a substituted or unsubstituted (
  • R a and R b each independently, may represent hydrogen, or an unsubstituted phenyl
  • R c may represent hydrogen, a phenyl unsubstituted or substituted with at least one methyl, an unsubstituted naphthyl, an unsubstituted biphenyl, an unsubstituted naphthylphenyl, a fluorenyl substituted with a dimethyl, or an unsubstituted phenanthrenyl.
  • adjacent two R a ’s or adjacent two R b ’s are linked to each other for at least one pair of the adjacent two R a ’s and the adjacent two R b ’s to form at least one substituted or unsubstituted benzene ring.
  • the number of the at least one substituted or unsubstituted benzene ring may be 1 to 6.
  • the adjacent two R a ’s or the adjacent two R b ’s, each independently, are linked to each other to form a substituted or unsubstituted benzene ring, and preferably, an unsubstituted benzene ring.
  • R c may represent a substituted or unsubstituted (C6-C18)aryl. Also, when X 2 to X 5 represent CR c , R c may represent hydrogen.
  • R f to R l each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (3- to 30-membered) alicyclic or aromatic ring, or a combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
  • p and q each independently, represent an integer of 1 to 4, and preferably an integer of 1 to 3. If p and q, each independently, are an integer of 2 or more, each of R a and R b may be the same or different.
  • Formula 1 may be represented by any one of the following formulas 2 to 7:
  • L 1 , Ar, R a , R b , X 1 to X 6 , p, and q are as defined in formula 1; and R d and R e are, each independently, identical to the definition of R a .
  • r and s each independently, represent an integer of 1 to 6. If r and s are, each independently, an integer of 2 or more, each of R d and R e may be the same or different.
  • the arylamine derivative comprised in the hole transport zone, preferably the second hole transport layer, for example, at least one of the light-emitting auxiliary layer and the hole auxiliary layer may comprise the compound represented by the following formula 11:
  • Ar 1 to Ar 3 each independently, represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; preferably, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl; and more preferably, an unsubstituted (C6-C18)aryl, or an unsubstituted (5- to 18-membered)heteroaryl.
  • Ar 1 to Ar 3 each independently, may represent a phenyl, a naphthyl, a biphenyl, a phenanthrenyl, a terphenyl, or a benzonaphthofuranyl.
  • at least one of Ar 1 to Ar 3 is selected from the following formulas:
  • L a to L c each independently, represent a single bond, or a substituted or unsubstituted (C6-C30)arylene; preferably, a single bond, or a substituted or unsubstituted (C6-C25)arylene; and more preferably, a single bond, or a (C6-C18)arylene unsubstituted or substituted with a di(C6-C18)arylamino.
  • L a to L c each independently, represent a single bond, a phenylene unsubstituted or substituted with a diphenylamino, or an unsubstituted biphenylene.
  • X represents O, S, or CR 19 R 20 .
  • the A ring represents a substituted or unsubstituted C10 aryl, preferably an unsubstitutued C10 aryl. According to one embodiment of the present disclosure, the A ring may represent a naphthalene ring.
  • R 1 to R 20 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR 21 R 22 , -SiR 23 R 24 R 25 , -SR 26 , -OR 27 , a cyano, a nitro, or a hydroxyl; or may be linked to an adjacent substituent to form a substituted or unsubstituted, mono
  • R 1 to R 20 each independently, represent hydrogen, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or -NR 21 R 22 ; or may be linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (3- to 25-membered) alicyclic or aromatic ring, or a combination thereof, in which the ring may include a spiro structure, and carbon atom(s) of the formed ring may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
  • R 1 to R 20 each independently, represent hydrogen, an unsubstituted (C1-C10)alkyl, a (C6-C18)aryl unsubstituted or substituted with a di(C6-C18)arylamino, or -NR 21 R 22 ; or may be linked to an adjacent substituent to form an unsubstituted, mono- or polycyclic, (3- to 18-membered) alicyclic or aromatic ring, or a combination thereof, in which the ring may include a spiro structure.
  • R 1 to R 20 may represent hydrogen; adjacent two R 2 ’s may be linked to each other to form a substituted or unsubstituted benzene ring;
  • R 4 and R 10 each independently, may represent a biphenyl;
  • R 8 may represent a phenyl substituted with a diphenylamino;
  • R 6 and R 7 each independently, may represent a methyl, a phenyl, or a triphenylenyl, and may be the same or different;
  • R 12 and R 13 each independently, may represent a methyl, and may be the same or different;
  • R 19 and R 20 each independently, represent a methyl or a phenyl, and may be the same or different;
  • R 6 and R 7 , or R 12 and R 13 may be linked to each other to form a spiro structure, for example, a spiro[fluorene-fluorene] or spiro[fluorene-benzofluor
  • R 21 to R 27 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a substituted or unsubstituted, mono- or polycyclic, (3- to 30-membered) alicyclic or aromatic ring, or a combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
  • R 21 to R 27 each independently, may represent hydrogen, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl, more preferably, a (C6-C18)aryl unsubstituted or substituted with a (C1-C10)alkyl.
  • R 21 and R 22 each independently, may represent a phenyl, a naphthylphenyl, a biphenyl, or a dimethylfluorenyl.
  • a, b, d, f, g, i, j, l, and m each independently, represent an integer of 1 to 4; c and e, each independently, represent an integer of 1 to 3; h represents an integer of 1 to 6; and k represents 1 or 2. If a to m, each independently, are an integer of 2 or more, each of R 1 to R 17 may be the same or different. Preferably, a to m, each independently, are 1 or 2.
  • the heteroaryl(ene) or the heterocycloalkyl contains at least one heteroatom selected from B, N, O, S, Si, and P; and preferably, at least one heteroatom selected from N, O, and S.
  • Formula 11 may be represented by any one of the following formulas 12 to 18:
  • R 1 to R 17 , a to m, L a to L c , Ar 1 , and Ar 2 are as defined in formula 11.
  • (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 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, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • (3- to 7-membered)heterocycloalkyl is meant to be a cycloalkyl having at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably selected from the group consisting of O, S, and N, and 3 to 7 ring backbone atoms, preferably 5 to 7 ring backbone atoms, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
  • (C6-C30)aryl(ene) is meant to be a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms and may be partially saturated, in which the number of ring backbone carbon atoms is preferably 6 to 25, more preferably 6 to 18, may include a spiro structure, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacen
  • (5- to 30-membered)heteroaryl(ene) is meant to be an aryl group having at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P, and 5 to 30 ring backbone atoms; is 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); may include a spiro structure; and includes a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl,
  • 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 may be at least one selected from the group consisting of a (C1-C20)alkyl; an unsubstituted (5- to 25-membered)heteroaryl; an unsubstituted (C6-C25)aryl; an amino; a mono- or di- (C1-C20)alkylamino; an unsubstituted mono- or di- (C6-C25)arylamino; a (C1-C20)alkyl(C6-C25)arylamino; a (C6-C25)aryl(C1-C20)alkyl; and a (C1-C20)alkyl(C6-C25)aryl.
  • a (C1-C20)alkyl an unsubstituted (5- to 25-membered)heteroaryl
  • an unsubstituted (C6-C25)aryl an amino; a mono- or di- (C1-C20)
  • the substitutents may be may be at least one selected from the group consisting of a (C1-C10)alkyl, a (C6-C18)aryl, and a di(C6-C18)arylamino.
  • the substituents may be at least one selected from the group consisting of a methyl, a naphthyl, and a diphenylamino.
  • the compound represented by formula 1 may be at least one selected from the following compounds, but is not limited thereto.
  • the compound represented by formula 11 may be at least one selected from the following compounds, but is not limited thereto.
  • the compound represented by formula 1 according to the present disclosure may be produced by a synthetic method known to one skilled in the art, and for example, may be synthesized with reference to the following reaction schemes 1 to 9, but is not limited thereto.
  • the compound represented by formula 11 according to the present disclosure may be produced by a synthetic method known to one skilled in the art, and for example, may be synthesized by using or modifying the synthetic methods disclosed in Korean Patent Application Laid-Open Nos. 2014-0104895 A, 2015-0012488 A, and 2015-0066202 A, and Korean Patent No. 1476231 B.
  • the dopant comprised in the organic electroluminescent device according to the present disclosure may include at least one phosphorescent or fluorescent dopant, and preferably, at least one phosphorescent dopant.
  • the phosphorescent dopant materials comprised in the organic electroluminescent device according to the present disclosure are not particularly limited, but may be selected from metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), may be preferably selected from ortho-metallated complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and may be more preferably an ortho-metallated iridium complex compound.
  • the dopant comprised in the organic electroluminescent device of the present disclosure may comprise the compound represented by the following formula 101, but is not limited thereto.
  • L is selected from the following structures:
  • R 100 to R 103 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, 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 R 100 to R 103 may be linked to adjacent R 100 to R 103 to form a substituted or unsubstituted fused ring with a pyridine, e.g., a substituted or unsubstituted quinoline, a substituted or unsubstituted isoquinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsubsti
  • R 104 to R 107 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, 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 R 104 to R 107 may be linked to adjacent R 104 to R 107 to form a substituted or unsubstituted fused ring with a benzene, e.g., a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene,
  • 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; or R 201 to R 211 may be linked to adjacent R 201 to R 211 to form a substituted or unsubstituted fused ring; and
  • n an integer of 1 to 3.
  • the dopant compound includes the following compounds, but is not limited thereto.
  • the organic electroluminescent device comprises a hole transport zone between a first electrode and a light-emitting layer, wherein the hole transport zone comprises an arylamine derivative containing a fluorene or a fused fluorene, and a HOMO energy level of the arylamine derivative satisfies the following equation 11.
  • the organic electroluminescent device may comprise a first hole transport layer between a first electrode and a light-emitting layer, and a second transport layer between the first hole transport layer and the light-emitting layer, wherein the second transport layer comprises an arylamine derivative containing a fluorene or a fused fluorene, and a HOMO energy level of the arylamine derivative satisfies the following equation 11.
  • the second hole transport layer may be a single layer or a plurality of layers, and may play a role as a hole transport layer, a light-emitting auxiliary layer, a hole auxiliary layer and/or an electron blocking layer.
  • the HOMO energy level of the arylamine derivative may satisfy the following formula 12:
  • the hole transport zone comprises the compound having a HOMO energy level of less than -5.0, for example, at most -5.1, it is less than the HOMO energy level of the compound represented by formula 1 comprised in the light-emitting layer.
  • the hole injection is blocked and the driving voltage increases. That is, although the luminous efficiency of a device increases, there is no advantage in terms of power efficiency (lm/W), rather, the power efficiency may decrease, since the driving power increases as much as the luminance efficiency increases.
  • the hole transport zone comprises the compound having a HOMO energy level more than -4.65
  • the energy barrier between the layer comprising said compound, for example, a second hole transport layer, and a light-emitting layer highly increases, and thus, rather, the hole injection is blocked. As a result, the luminous efficiency may decrease.
  • the difference between the upper limit value and the lower limit value in the HOMO energy level of the compound comprised in the hole transport zone may be approximately 0.3 eV or less.
  • a display device for example, for smartphones, tablets, notebooks, PCs, TVs, or vehicles, or a lighting device, for example, an indoor or outdoor lighting device, can be produced.
  • the organic electroluminescent device of the present disclosure is intended to explain one embodiment of the present disclosure, and is not meant in any way to restrict the scope of the disclosure.
  • the organic electroluminescent device may be embodied in another way.
  • the HOMO energy levels were measured by using density functional theory (DFT) in Gaussian 03 program of Gaussian Inc. Specifically, the HOMO and LUMO energy levels in the Device Examples and Comparative Examples were extracted from the structure having the lowest energy by optimizing the structures of isomers in all possible forms at the level of B3LYP/6-31g*, and then comparing the calculated energies of the isomers.
  • DFT density functional theory
  • OLED organic light-emitting diode
  • An OLED device was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED device (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone and isopropanol, 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.
  • ITO indium tin oxide
  • 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 a 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.
  • the compound shown in Table 1 below 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: Compound H-139 was introduced into one cell of the vacuum vapor deposition apparatus as a host, and compound D-39 was introduced into another cell as a dopant.
  • the two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 2 wt% based on the total amount of the host and the 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 introduced into another two cells of the vacuum vapor deposition apparatus and evaporated at a rate of 1:1 to form 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 device was produced.
  • An OLED device was produced in the same manner as in Device Example 1, except that the compound shown in Table 1 below was used in the second hole transport layer.
  • An OLED device was produced in the same manner as in Device Example 3, except that compound C-1 was used as the host of the light-emitting layer.
  • the driving voltage, luminous efficiency, and CIE color coordinates at a luminance of 1,000 nits, and the lifespan (measured as the percentage to which the luminance is decreased from 100% after 16.7 hours at a luminance of 5,000 nits and a constant current) produced in the OLED devices of Device Examples 1 to 6 and Comparative Examples 1 and 2 are provided in Table 1 below.
  • the HOMO energy levels of the compounds comprised in the second hole transport layer of Device Examples 1 to 6 and Comparative Examples 1 and 2 are provided in Table 2 below.
  • Device Example 3 comprising the benzoindolocarbazole derivative of the present disclosure as a host has significantly improved luminous efficiency, while maintaining driving voltage and lifespan characteristics in equivalent or similar levels, compared to Comparative Example 2 comprising the indolocarbazole derivative as a host. Further, it can be confirmed that Device Example 3 comprising the compound having a specific HOMO energy level of the present disclosure in a hole transport zone has significantly improved luminous efficiency, while maintaining driving voltage and lifespan characteristics at equivalent or similar levels, compared to Comparative Example 1.

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Abstract

La présente invention concerne un dispositif électroluminescent organique comprenant une couche électroluminescente et une zone de transport de trous. Par la combinaison de la couche électroluminescente comprenant le composé selon la présente invention et la zone de transport de trous comprenant le composé ayant un niveau d'énergie HOMO spécifique, on obtient le dispositif électroluminescent organique ayant un excellent rendement lumineux.
PCT/KR2018/003245 2017-03-31 2018-03-21 Dispositif électroluminescent organique Ceased WO2018182221A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11053437B2 (en) 2019-06-28 2021-07-06 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent devices, organic electroluminescent device and electronic device
JP2022514880A (ja) * 2018-12-20 2022-02-16 メルク パテント ゲーエムベーハー 電子デバイス用の材料
US11820747B2 (en) 2021-11-02 2023-11-21 Flare Therapeutics Inc. PPARG inverse agonists and uses thereof
US11844269B2 (en) * 2017-06-30 2023-12-12 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same

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Publication number Priority date Publication date Assignee Title
WO2015142036A1 (fr) * 2014-03-17 2015-09-24 Rohm And Haas Electronic Materials Korea Ltd. Matériau tampon de confinement d'électrons et dispositif électroluminescent organique comportant de matériau
WO2016013867A1 (fr) * 2014-07-22 2016-01-28 Rohm And Haas Electronic Materials Korea Ltd. Dispositif électroluminescent organique
WO2016148390A1 (fr) * 2015-03-13 2016-09-22 Rohm And Haas Electronic Materials Korea Ltd. Pluralité de matériaux hôtes et dispositif électroluminescent organique comprenant ces matériaux

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WO2015142036A1 (fr) * 2014-03-17 2015-09-24 Rohm And Haas Electronic Materials Korea Ltd. Matériau tampon de confinement d'électrons et dispositif électroluminescent organique comportant de matériau
WO2016013867A1 (fr) * 2014-07-22 2016-01-28 Rohm And Haas Electronic Materials Korea Ltd. Dispositif électroluminescent organique
WO2016148390A1 (fr) * 2015-03-13 2016-09-22 Rohm And Haas Electronic Materials Korea Ltd. Pluralité de matériaux hôtes et dispositif électroluminescent organique comprenant ces matériaux

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11844269B2 (en) * 2017-06-30 2023-12-12 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same
JP2022514880A (ja) * 2018-12-20 2022-02-16 メルク パテント ゲーエムベーハー 電子デバイス用の材料
US12069950B2 (en) 2018-12-20 2024-08-20 Merck Kgaa Materials for electronic devices
US11053437B2 (en) 2019-06-28 2021-07-06 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent devices, organic electroluminescent device and electronic device
US11820747B2 (en) 2021-11-02 2023-11-21 Flare Therapeutics Inc. PPARG inverse agonists and uses thereof

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