WO2021118086A2 - Composé organique et dispositif électroluminescent organique le comprenant - Google Patents

Composé organique et dispositif électroluminescent organique le comprenant Download PDF

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WO2021118086A2
WO2021118086A2 PCT/KR2020/016143 KR2020016143W WO2021118086A2 WO 2021118086 A2 WO2021118086 A2 WO 2021118086A2 KR 2020016143 W KR2020016143 W KR 2020016143W WO 2021118086 A2 WO2021118086 A2 WO 2021118086A2
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aryl
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nuclear atoms
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WO2021118086A3 (fr
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박우재
엄민식
심재의
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솔루스첨단소재 주식회사
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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]
    • H10K50/14—Carrier transporting layers
    • 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
    • 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 invention relates to a novel organic compound and an organic electroluminescent device comprising the same, and more particularly, to a compound excellent in carrier transport ability, luminescent ability and heat resistance, and luminous efficiency, driving voltage, lifespan, etc. by including the compound in one or more organic material layers It relates to an organic electroluminescent device with improved properties.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their function.
  • the light emitting material may be divided into blue, green, and red light emitting materials and yellow and orange light emitting materials for realizing a better natural color according to the light emitting color.
  • a host/dopant system may be used as a light emitting material.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • the hole injection layer, the hole transport layer. NPB, BCP, Alq 3 and the like are widely known as the material for the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as the material for the light emitting layer.
  • metal complex compounds containing Ir such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2 , which have advantages in terms of efficiency improvement among light emitting layer materials, are blue, green, and red. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.
  • the present invention has excellent heat resistance, carrier transport ability, light emitting ability, etc., so that it can be used as an organic layer material of an organic electroluminescent device, specifically, a light emitting layer material, a life improvement layer material, a light emitting auxiliary layer material, and/or an electron transport layer material. It aims to provide novel compounds.
  • the present invention provides a compound represented by the following formula (1).
  • Z 1 To Z 3 are the same as or different from each other, and each independently C(R 1 ) or N, provided that at least two of Z 1 To Z 3 are N,
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 ⁇ C 40 alkyl Oxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl Boron group, C 6 ⁇ C 60 Arylphosphanyl group, C 6 ⁇ C 60 Monoarylphosphinyl group, C 6 ⁇ C 60 Diarylphosphinyl group, C 6 ⁇
  • L is a single bond, or is selected from the group consisting of a C 6 ⁇ C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms,
  • A is a substituent represented by any one of Formula 1a or Formula 1b,
  • X is a single bond or is selected from the group consisting of O, S and CR 2 R 3 ,
  • n is an integer from 0 to 3
  • m is an integer from 0 to 6
  • R 1 To R 4 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 of Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphanyl group, C 6 ⁇ C 60 Monoaryl phosphinyl group, C 6 ⁇ C 60 Diaryl phosphinyl group
  • Ar 1 to Ar 2 , and R 1 to R 4 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group , alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, nuclear atoms 5 to 60 Heteroary
  • the present invention provides an electron transport layer or an electron transport auxiliary layer comprising the compound represented by the above formula (1).
  • the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is an organic electroluminescence containing a compound represented by Formula 1 provide the element.
  • the organic material layer including the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer.
  • the compound represented by Formula 1 may be included as a phosphorescent host material of the emission layer, and an electron transport material of the electron transport layer and the electron transport auxiliary layer.
  • the compound represented by Formula 1 has excellent heat resistance, carrier transport ability, light emitting ability, and the like, and thus can be used as an organic material layer material of an organic electroluminescent device.
  • the compound represented by Formula 1 of the present invention when used as a phosphorescent host, electron transport layer or electron transport auxiliary layer material, compared to conventional host materials or electron transport materials, high thermal stability, low driving voltage, fast mobility, and high current efficiency and long life characteristics.
  • the organic electroluminescent device containing the compound represented by Formula 1 can greatly improve aspects such as light emitting performance, driving voltage, lifespan, and efficiency, and thus can be effectively applied to a full color display panel.
  • the effect according to the present invention is not limited by the contents exemplified above, and more various effects are included in the present specification.
  • a nitrogen-containing heteroaromatic ring eg, azine
  • a benzoxanthene (A)-based moiety are positioned at both ends of the molecule, and they are directly connected or a separate linker It has a basic skeletal structure connected through (L).
  • the compound of Formula 1 is a nitrogen-containing aromatic ring (eg, pyrazine, pyrimidine, triazine) which is a type of a benzoxanthine-based moiety as an electron donor group (EDG) and an azine group as an electron withdrawing group (EWG) with high electron absorption. ) at the same time.
  • EDG electron donor group
  • EWG electron withdrawing group
  • the electron transfer speed is improved, and thus it is possible to have physicochemical properties more suitable for electron injection and electron transport.
  • the compound of Formula 1 When the compound of Formula 1 is applied as a material for an electron transport layer or an electron transport auxiliary layer, it can accept electrons from the cathode well and thus smoothly transfer electrons to the light emitting layer, thereby lowering the driving voltage of the device and improving high efficiency and long lifespan can induce As a result, such an organic electroluminescent device can maximize the performance of a full color organic light emitting panel.
  • the benzoxanthine-based moiety adopted in the present invention exhibits high luminous efficiency compared to conventional dibenzo-based moieties or anthracene derivatives, and has a structure in which color coordinates can be easily tuned.
  • the compound of Formula 1 including such a benzoxanthine-based moiety has a triplet energy as high as 2.3 eV or more.
  • an electron withdrawing group (EWG) of azines is introduced into the basic skeleton in which a xanthine derivative having a wide singlet energy level and a high triplet energy level is condensed, so that the energy level is high.
  • the compound represented by Formula 1 may be used as a light emitting auxiliary layer material or a life improvement layer material in addition to the host of the light emitting layer.
  • the compound of Formula 1 described above is a bipolar compound, so that hole injection/transport capability, luminous efficiency, driving voltage, lifespan characteristics, durability, and the like can be improved.
  • the electron transport ability and the like can be improved depending on the type of the introduced substituent.
  • the compound of Formula 1 may be used as an organic material layer material of an organic electroluminescent device, preferably an electron transport layer, an electron transport auxiliary layer material, and a light emitting layer material.
  • the compound represented by Formula 1 is not only very advantageous for electron transport, but also shows low driving voltage, high efficiency, and long lifespan characteristics.
  • the excellent electron transport ability of these compounds can have high efficiency and fast mobility in the organic electroluminescent device, and it is easy to control the HOMO and LUMO energy levels according to the direction or position of the substituent. Therefore, it is possible to exhibit high electron transport properties in an organic electroluminescent device using such a compound.
  • the red and green light emitting layers of the organic EL device use phosphorescent materials, respectively, and their technological maturity is high.
  • the blue light emitting layer includes a fluorescent material and a phosphorescent material.
  • the fluorescent material is in a state in which performance improvement is required, and the blue phosphorescent material is still under development, so the entry barrier is high. That is, since the blue light emitting layer has a high development possibility and a relatively high technical difficulty, there is a limit in improving the performance (eg, driving voltage, efficiency, lifespan, etc.) of the blue organic light emitting device having the blue light emitting layer.
  • the compound of Formula 1 may be applied as a material for an electron transport layer (ETL) or an electron transport auxiliary layer in addition to the light emitting layer (EML).
  • ETL electron transport layer
  • EML electron transport auxiliary layer
  • the performance of the light emitting layer, specifically the blue light emitting layer, and the performance of the organic electroluminescent device having the same are improved. There is an advantage that you can.
  • the compound represented by Formula 1 according to the present invention has a basic skeleton structure in which a benzoxanthene-based moiety and a nitrogen-containing heteroaromatic ring (eg, azine) are connected directly or through a linker (L). .
  • the nitrogen-containing heteroaromatic ring is a nitrogen-containing heteroaryl group (eg, azine, Z 1 to Z 3 containing heterocyclic ring) containing at least two nitrogen atoms, which is an electron withdrawing group excellent in electron transport (Electron Withdrawing Group, EWG) is a kind of
  • Z 1 to Z 3 are the same as or different from each other, and are each independently C(R 1 ) or N, but At least two of Z 1 to Z 3 are N.
  • Z 1 to Z 3 include 2 to 3 N.
  • These triazines, pyrimidines, pyrazines, etc. are a type of 6-membered heterocyclic ring with high electron withdrawing group (EWG) characteristics including 2 to 3 nitrogens, respectively, and thus exhibit excellent electron absorption characteristics, which is advantageous for electron injection and transport.
  • EWG electron withdrawing group
  • a plurality of R 1 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 of Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 the arylboronic group, C 6 ⁇ C 60 aryl phosphazene group, C 6 ⁇ C 60 mono-aryl phosphonium blood group, C 6 ⁇ C 60 of the diaryl P
  • a plurality of R 1 are the same as or different from each other, and each independently hydrogen, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a group consisting of a heteroaryl group having 5 to 60 nuclear atoms It is preferably selected from
  • Ar 1 and Ar 2 may be substituted as various substituents, respectively.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 of Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 An aryl boron group of, C 6 ⁇ C 60 Aryl phosphanyl group, C 6 ⁇ C 60 Monoaryl phosphinyl group, C 6 ⁇ C 60 Diaryl phosphiny
  • Ar 1 and Ar 2 are each independently a C 1 ⁇ C 40 alkyl group, a C 6 ⁇ C 60 aryl group, a heteroaryl group of 5 to 60 nuclear atoms, a C 6 ⁇ C 60 aryloxy group, It may be selected from a C 6 ⁇ C 60 arylphosphine oxide group and a C 6 ⁇ C 60 arylamine group, preferably in a C 6 ⁇ C 60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms. can be selected.
  • Ar 1 and Ar 2 are each independently a C 6 ⁇ C 18 aryl group, but these may be different from each other.
  • the nitrogen- containing heteroaromatic ring (eg, Z 1 to Z 3 containing ring) may be more specific to any one selected from the group of substituents represented by the following A-1 to A-3.
  • the present invention is not limited thereto.
  • R 1 , Ar 1 , and Ar 2 are each as defined in Formula 1;
  • a monocyclic heteroaromatic ring is specifically exemplified as a nitrogen-containing heteroaromatic ring (eg, a ring containing Z 1 to Z 3 ).
  • a nitrogen-containing heteroaromatic ring eg, a ring containing Z 1 to Z 3
  • the present invention is not limited thereto, and the use of conventional polycyclic, condensed, and/or fused nitrogen-containing heteroaromatic rings known in the art is also within the scope of the present invention.
  • the aforementioned nitrogen-containing heteroaromatic ring (eg, Z 1 to Z 3 containing ring, azine group) may be directly bonded to a benzoxanthene-based moiety or may be bonded through a separate linker (L).
  • a separate linker (L) exists between the azine group and the benzoxanthine-based moiety, the HOMO region is extended to give a benefit to the HOMO-LUMO distribution, and the charge transfer efficiency can be increased through the appropriate overlap of the HOMO-LUMO. have.
  • the linker (L) may be a linker of a conventional divalent group known in the art.
  • L may be a single bond (eg, a direct bond) or a C 6 ⁇ C 18 arylene group and may be selected from the group consisting of a heteroarylene group having 5 to 18 nuclear atoms.
  • L may be a single bond, or an arylene group moiety of the following formula (2).
  • n is an integer of 1 to 2.
  • the moiety of Formula 2 may be an arylene group linker known in the art, and specific examples thereof include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyrantrenylene group, a carbazolyl group. Rene group, thiophenylene group, indolylene group, purinylene group, quinolinylene group, pyrrolylene group, imidazolylene group, oxazolylene group, thiazolylene group, pyridinylene group, pyrimidinylene group, and the like. More specifically, the linker (L) represented by Formula 2 may be a phenylene group or a biphenylene group.
  • the linker of Formula 2 may be a linker selected from the following structural formulas.
  • linker (L) is not specifically shown in the formula, at least one or more substituents known in the art (eg, R 1 ) may be substituted.
  • the compound represented by Formula 1 of the present invention is a direct bond or linker (L) on one side of a nitrogen-containing heteroaromatic ring (eg, Z 1 to Z 3 containing ring), which is a kind of electron withdrawing group (EWG) having excellent electron transport ability. It is bound to a benzoxanthine-based moiety (eg, A) through The benzoxanthine-based moiety (A) may be any one of Formula 1a or Formula 1b below.
  • X may be a single bond or may be selected from the group consisting of O, S and CR 2 R 3 .
  • R 2 To R 3 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phosphanyl group, C 6 ⁇ C 60 Monoaryl phosphinyl group, C 6 ⁇ C 60 Diaryl phosphinyl group, C
  • R 2 To R 3 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, and the number of nuclear atoms 5 It may be selected from the group consisting of to 60 heteroaryl groups.
  • R 4 substituted in the benzoxanthine-based moiety (A) represented by Formula 1a or 1b may be a conventional substituent known in the art, and is not particularly limited. For example, it may be the same as the definition of R 2 to R 3 described above.
  • the number (m) of R 4 is not particularly limited, and may be an integer of 0 to 6, for example.
  • R 4 when m is 0, R 4 is hydrogen, and when m is 1 to 6, R 4 may have the aforementioned substituents other than hydrogen.
  • the benzoxanthine-based moiety (A) may be further specified by the following structural formula.
  • benzoxanthine-based moiety (A) embodied in the above-mentioned structural formula is not specifically shown in the formula, at least one or more substituents known in the art (eg, R 4 ) may be substituted.
  • L is an arylene group or a heteroarylene group
  • Ar 1 to Ar 2 , and R 1 to R 4 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group , alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and arylamine group are each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 6 ⁇ C 60 aryl group, nuclear atom
  • the compound represented by Chemical Formula 1 may be more specific to the following Chemical Formula 3 or 4 depending on the type of the benzoxanthine-based moiety (A).
  • Z 1 to Z 3 , X, Ar 1 to Ar 2 , L and n are each as defined in Chemical Formula 1.
  • the compound represented by Formula 3 may be more specific to any one of the following Formulas 5 to 8 depending on the bonding position of the linker (L) connected to the benzoxanthine-based core.
  • the present invention is not limited thereto.
  • Z 1 to Z 3 , X, Ar 1 to Ar 2 , L and n are each as defined in Chemical Formula 1.
  • the compound represented by Chemical Formula 4 may be more specific to any one of the following Chemical Formulas 9 to 12 depending on the bonding position of the linker (L) connected to the benzoxanthine-based core.
  • the present invention is not limited thereto.
  • Z 1 to Z 3 , X, Ar 1 to Ar 2 , L and n are each as defined in Formula 1.
  • Z 1 to Z 3 are N, and Ar 1 and Ar 2 are the same as or different from each other, and each independently C 6 ⁇ C 60 It is selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.
  • L is a single bond or a C 6 ⁇ C 18 arylene group, and n is an integer of 1 to 2.
  • R 1 To R 4 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, and 5 to 60 nuclear atoms It is selected from the group consisting of a heteroaryl group, and m is an integer from 0 to 6.
  • the arylene group of L; Ar 1 and Ar 2 An aryl group, a heteroaryl group; And R 1 To R 4 Alkyl group, aryl group, heteroaryl group is each independently hydrogen, deuterium (D), halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, It may be substituted with one or more substituents selected from the group consisting of a heteroaryl group having 5 to 60 nuclear atoms, and an arylamine group of C 6 to C 60. In this case, when the substituents are plural, they may be the same or different from each other.
  • the compound represented by Formula 1 of the present invention described above may be further embodied as a compound exemplified below, for example, a compound represented by 1 to 200.
  • the compound represented by Formula 1 of the present invention is not limited by those exemplified below.
  • alkyl refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
  • alkenyl refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl) and the like.
  • alkynyl refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
  • aryl refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms in which a single ring or two or more rings are combined.
  • two or more rings may be simply attached to each other (pendant) or condensed form may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • heteroaryl refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms.
  • one or more carbons, preferably 1 to 3 carbons in the ring are substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazole, and carbazolyl, and 2-furanyl, N-imidazolyl, and 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl), purinyl, quinolyl, benzothiazo
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 40 carbon atoms.
  • R means aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure. may include.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
  • arylamine means an amine substituted with an aryl having 6 to 40 carbon atoms.
  • cycloalkyl means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • heterocycloalkyl means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or a hetero atom such as Se.
  • heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
  • alkylsilyl refers to silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl refers to silyl substituted with aryl having 5 to 40 carbon atoms.
  • condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the present invention provides an electron transport layer comprising the compound represented by Formula 1 above.
  • the electron transport layer serves to move electrons injected from the cathode to an adjacent layer, specifically, the light emitting layer.
  • the compound represented by Formula 1 may be used alone as an electron transport layer (ETL) material, or may be mixed with an electron transport layer material known in the art. It is preferably used alone.
  • ETL electron transport layer
  • the electron transport layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art.
  • the electron transport material that can be used include an oxazole-based compound, an isoxazole-based compound, a triazole-based compound, an isothiazole-based compound, an oxadiazole-based compound, a thiadiazole-based compound, and perylene ( perylene)-based compound, aluminum complex (eg, Alq 3 (tris(8-quinolinolato)-aluminium) BAlq, SAlq, Almq3, gallium complex (eg, Gaq'2OPiv, Gaq) '2OAc, 2(Gaq'2)), etc. These may be used alone or in combination of two or more.
  • the compound of Formula 1 and the electron transport layer material are mixed, their mixing ratio is not particularly limited, and may be appropriately adjusted within a range known in the art.
  • the present invention provides an electron transport auxiliary layer including the compound represented by the formula (1).
  • the electron transport layer is disposed between the emission layer and the electron transport layer, and serves to prevent the excitons or holes generated in the emission layer from diffusing into the electron transport layer.
  • the compound represented by Formula 1 may be used alone as an electron transport auxiliary layer material, or may be mixed with an electron transport layer material known in the art. It is preferably used alone.
  • the electron transport auxiliary layer material that can be mixed with the compound of Formula 1 includes an electron transport material commonly known in the art.
  • the electron transport auxiliary layer may include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative (eg, BCP), a nitrogen-containing heterocyclic derivative, and the like.
  • the compound of Formula 1 and the electron transport auxiliary layer material are mixed, their mixing ratio is not particularly limited and may be appropriately adjusted within a range known in the art.
  • organic electroluminescent device including the compound represented by Formula 1 according to the present invention.
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is and a compound represented by Formula 1 above.
  • the compound may be used alone or in combination of two or more.
  • the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emission auxiliary layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and at least one organic material layer is represented by Formula 1 compounds.
  • the organic material layer including the compound of Formula 1 is a light emitting layer (more specifically, a phosphorescent light emitting host material), an electron transport layer, and an electron transport auxiliary layer.
  • the light emitting layer of the organic electroluminescent device according to the present invention includes a host material and a dopant material, and in this case, the compound of Formula 1 may be included as the host material.
  • the light emitting layer of the present invention may include a known compound in the art other than the compound of Formula 1 as a host.
  • the compound represented by Formula 1 is included as a light emitting layer material of an organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, since the bonding force between holes and electrons in the light emitting layer is increased, the efficiency of the organic electroluminescent device (luminous efficiency and power efficiency), lifespan, luminance, and driving voltage can be improved.
  • the compound represented by Formula 1 is preferably included in the organic electroluminescent device as a green and/or red phosphorescent host, a fluorescent host, or a dopant material.
  • the compound represented by Formula 1 of the present invention is preferably a green phosphorescent exciplex N-type host material of a light emitting layer having high efficiency.
  • the structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and a cathode are sequentially stacked.
  • at least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include the compound represented by Formula 1, preferably the light emitting layer, more preferably a phosphorescent host may include a compound represented by Formula 1 above.
  • an electron injection layer may be additionally stacked on the electron transport layer.
  • the structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.
  • the organic electroluminescent device of the present invention may be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Formula 1 above. have.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.
  • the substrate used in manufacturing the organic electroluminescent device of the present invention is not particularly limited, and for example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet may be used.
  • a cathode material a cathode material known in the art may be used without limitation.
  • metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT), polypyrrole or polyaniline; and carbon black, but is not limited thereto.
  • a negative electrode material a negative electrode material known in the art may be used without limitation.
  • a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; and a multilayer structure material such as LiF/Al or LiO2/Al, but is not limited thereto.
  • the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer are not particularly limited, and conventional materials known in the art may be used without limitation.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After cleaning with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., and drying, transfer to a UV OZONE cleaner (Power sonic 405, Hwashin Tech) The substrate was transferred to a vacuum evaporator.
  • ITO indium tin oxide
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq 3 was used instead of Compound 6 as the electron transport layer material.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the electron transport layer material was not included.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound A-1 was used instead of Compound 6 as the electron transport layer material.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound A-2 was used instead of Compound 6 as the electron transport layer material.
  • the blue organic electroluminescent devices of Examples 1 to 8 using the compound of the present invention as an electron transport layer material the blue organic electroluminescent device of Comparative Example 1 using Alq 3 as an electron transport layer material in the prior art ; And it was found that the blue organic EL device of Comparative Example 2 not including an electron transport layer exhibits significantly superior performance in terms of driving voltage, emission peak and current efficiency compared to the blue organic EL device of Comparative Example 2.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is performed and dried, transferred to a UV OZONE washer (Power sonic 405, Hwashin Tech), and then the substrate is washed using UV for 5 minutes and transferred the substrate to a vacuum evaporator.
  • ITO indium tin oxide
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 9, except that Compound 56 was not used as an electron transport auxiliary layer material, and Alq 3, an electron transport layer material, was deposited at 30 nm instead of 25 nm. .
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 9, except that Compound A-1 was used instead of Compound 56 as an electron transport auxiliary layer material.
  • a blue organic electroluminescent device was manufactured in the same manner as in Example 9, except that Compound A-2 was used instead of Compound 56 as an electron transport auxiliary layer material.
  • Example 9 compound 56 3.1 454 8.0
  • Example 10 compound 63 3.0 454 8.1
  • Example 11 compound 66 3.2 454 8.2
  • Example 12 compound 68 3.1 454 8.1
  • Example 13 compound 181 3.1 454 8.0
  • Example 14 compound 188 3.2 454 8.1
  • Example 15 compound 191 3.1 455 8.2
  • Example 16 compound 193 3.2 454 8.3 Comparative Example 5 - 4.7 459 6.1 Comparative Example 6 A-1 4.3 459 5.9 Comparative Example 7 A-2 4.8 455 5.3
  • the blue organic electroluminescent devices of Examples 9 to 16 using the compound of the present invention as an electron transport auxiliary layer material were the blue organic electroluminescent devices of Comparative Example 5 without an electron transport auxiliary layer. Compared to that, it showed excellent performance in terms of current efficiency and luminescence peak, and particularly in terms of driving voltage.
  • the blue organic electroluminescent devices of 9 to 16 are of Comparative Example 6 including an electron transport auxiliary layer material having a conventional dibenzo-based moiety and a fluorene group, and Comparative Example 7 including an electron transport layer material not including an azine group It was found that the blue organic EL device exhibited superior performance in terms of driving voltage, emission peak and current efficiency compared to the blue organic EL device.

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  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
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Abstract

La présente invention concerne un nouveau composé ayant une capacité de transport de porteurs, une capacité d'émission de lumière et une stabilité thermique excellentes, et un dispositif électroluminescent organique le comprenant dans une ou plusieurs couches de matériau organique, présentant ainsi des caractéristiques améliorées telles que l'efficacité lumineuse, la tension de commande et la durée de vie.
PCT/KR2020/016143 2019-12-13 2020-11-17 Composé organique et dispositif électroluminescent organique le comprenant WO2021118086A2 (fr)

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CN114230546A (zh) * 2021-11-19 2022-03-25 陕西莱特光电材料股份有限公司 有机化合物、有机电致发光器件和电子装置
WO2023223855A1 (fr) * 2022-05-20 2023-11-23 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique

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CN112358471B (zh) * 2020-10-26 2022-07-19 吉林奥来德光电材料股份有限公司 含杂原子的螺环类有机电致发光化合物及其制备方法和应用
KR20230081764A (ko) * 2021-11-29 2023-06-08 엘티소재주식회사 헤테로고리 화합물, 이를 포함하는 유기 발광 소자 및 유기물층 형성용 조성물
WO2023228828A1 (fr) * 2022-05-27 2023-11-30 出光興産株式会社 Élément électroluminescent organique et dispositif électronique

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KR20110112098A (ko) * 2010-04-06 2011-10-12 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
US10680182B2 (en) * 2012-11-21 2020-06-09 Lg Chem, Ltd. Fluoranthene compound, and organic electronic device comprising same
EP3533793A1 (fr) * 2018-02-28 2019-09-04 Novaled GmbH Dispositif électronique organique, afficheurs et dispositifs d'éclairage le comprenant
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CN114230546A (zh) * 2021-11-19 2022-03-25 陕西莱特光电材料股份有限公司 有机化合物、有机电致发光器件和电子装置
CN114230546B (zh) * 2021-11-19 2023-09-12 陕西莱特光电材料股份有限公司 有机化合物、有机电致发光器件和电子装置
WO2023223855A1 (fr) * 2022-05-20 2023-11-23 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique

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