WO2019143112A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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WO2019143112A1
WO2019143112A1 PCT/KR2019/000616 KR2019000616W WO2019143112A1 WO 2019143112 A1 WO2019143112 A1 WO 2019143112A1 KR 2019000616 W KR2019000616 W KR 2019000616W WO 2019143112 A1 WO2019143112 A1 WO 2019143112A1
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group
formula
aryl
bonded
light emitting
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PCT/KR2019/000616
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English (en)
Korean (ko)
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한송이
엄민식
홍진석
심재의
박정근
손효석
이용환
박우재
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주식회사 두산
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Publication of WO2019143112A1 publication Critical patent/WO2019143112A1/fr

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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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • 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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to an organic electroluminescent device having improved characteristics such as high luminous efficiency, low driving voltage and long life time by using a novel compound as a host material of a light emitting layer.
  • the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on its function.
  • the light emitting layer forming material of the organic electroluminescent device can be classified into blue, green and red light emitting materials according to the luminescent color.
  • yellow and orange light emitting materials are also used as light emitting materials for realizing better color.
  • a host / dopant system can be used as a light emitting material.
  • the dopant material can 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.
  • NPB, BCP, Alq 3 and the like are widely known as materials used for the hole injecting layer, the hole transporting layer, the hole blocking layer and the electron transporting layer, and the anthracene derivatives as a luminescent material have been reported as a fluorescent dopant / host material .
  • Ir as a phosphorescent material that has a great advantage in improving the efficiency aspects of the light-emitting material (ppy) 3, (acac) Ir (btp) 2
  • Ir metal complex compound is a blue, green and red host material that includes such as . So far, CBP has shown excellent properties as a phosphorescent host material.
  • Patent Document 1 Japanese Laid-Open Patent Publication No. 2001-160489
  • the present invention has been conceived to solve the above-described problems, and it is an object of the present invention to provide an organic electroluminescent device using a novel compound as a host material of a light emitting layer, exhibiting a high luminous efficiency and a low driving voltage, The purpose.
  • a negative electrode disposed opposite to the positive electrode; And a light-emitting layer interposed between the anode and the cathode, wherein the light-emitting layer comprises at least one host and a dopant, wherein the at least one host is an organo-organic compound comprising a compound represented by the following formula
  • An electroluminescent device is provided.
  • X 1 and X 2 are the same as or different from each other and each independently O or S,
  • Y 1 to Y 16 are the same as or different from each other, and each independently CR 8 or N, provided that when there are a plurality of CR 8 s , the plurality of R 8 s are the same as or different from each other,
  • Z 1 to Z 3 are the same or different and each independently CR 5 or N, at least one of them is N,
  • Ar 1 is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, C 3 to C 40 cycloalkyl, A C 6 to C 60 aryl group,
  • n are each an integer of 0 to 3, m + n? 1,
  • a and B are the same or different from each other and are each independently any one of substituents represented by the following formulas (2) to (4);
  • X 3 is a single bond, or O or S,
  • L is a single bond or an arylene group having 6 to 40 carbon atoms
  • Ar 2 and Ar 3 are the same or different and each independently represents a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C 6 ⁇ , or selected from the group consisting of C 60 aryl amine, with or adjacent groups bonded may form a condensed ring,
  • a, c, and f are each an integer of 0 to 3
  • b, d and e are each an integer of 0 to 4, wherein b + m? 4, d + n? 4,
  • R 1 to R 8 are the same or different from each other and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 An alkynyl group, a C 3 to C 40 cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyl A C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ , or selected from the group consisting of an
  • An alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an arylamine group are each independently selected from the group consisting of deuterium, halogen, cyano group, nitro group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group , A C
  • an organic electroluminescent device including a host and a dopant as a light emitting layer component and simultaneously controlling the LUMO energy level and the triplet energy of the host and the dopant to a specific range has high light emission characteristics, low driving voltage, . Further, a full color display panel having improved performance and lifetime can be manufactured.
  • FIG. 1 is a cross-sectional view illustrating a structure of an organic electroluminescent device according to an embodiment of the present invention.
  • organic electroluminescent device A organic layer
  • the present invention relates to a positive electrode; cathode; And at least one organic material layer interposed between the anode and the cathode and including a hole transporting region, a light emitting layer, and an electron transporting region, wherein the organic material layer includes a compound represented by Formula 1 and a dopant, Energy, triplet energy, etc.) is controlled to a specific range.
  • the light emitting layer In the light emitting layer, excitons are generated while electrons generated at the cathode and holes generated at the anode meet and recombine, and light is emitted while the exciton transitions to the ground state.
  • the light emitting layer includes a host and a dopant doped to the host. In the process of energy transfer from the host to the dopant, the luminous efficiency of the device is improved. If the physical properties of the host and the dopant are not properly configured, the luminous efficiency of the device is lowered and the lifetime is shortened .
  • a compound having a novel structure represented by the formula (1) is used as the host and a dopant as the constituent of the light emitting layer, and the properties (such as LUMO energy, triplet energy, etc.) between such a host and the dopant are optimized So that the driving voltage, luminous efficiency and lifetime characteristics of the device are simultaneously improved.
  • the difference in energy level between the lowest unoccupied molecular orbital (LUMO) between the host and the dopant is adjusted to 1.0 eV or less, preferably 0.5 eV or less.
  • the triplet energy level of the host material present in the luminescent layer must be higher than the triplet energy of the dopant material. This is because the excitons in the triplet of the dopant can be prevented from reversing to the host again, and the luminous efficiency, driving voltage and lifetime of the organic electroluminescent device can be further improved.
  • a host and a dopant of a novel structure are included as a light emitting layer component, and by controlling the physical properties between them to a predetermined range, not only the energy transfer from the host to the dopant is facilitated, but also the reversal of the exciton It can be seen that the luminous efficiency of the device is significantly improved by preventing this phenomenon, the durability and the stability of the device are improved, and the lifetime of the device can be efficiently increased. Thus, a full color display panel having improved efficiency and long life characteristics can be manufactured.
  • An organic electroluminescent device includes a light emitting layer including a compound represented by Formula 1 and a dopant and having physical properties (e.g., LUMO energy level, triplet energy) do.
  • the compound is used as a host material (phosphorescent host) of the light emitting layer.
  • FIG. 1 is a view illustrating a structure of an organic electroluminescent device according to an embodiment of the present invention.
  • the organic electroluminescent device 100 includes an anode 10; A cathode 20; And a light emitting layer 40 positioned between the anode 10 and the cathode 20.
  • the organic electroluminescent device 100 includes a hole transport region 30 disposed between the anode 10 and the light emitting layer 40; And an electron transporting region 50 disposed between the light emitting layer 40 and the cathode 20 and preferably includes at least one of a hole transporting region 30 and an electron transporting region 50 .
  • the anode 10 serves to inject holes into the organic material layer A.
  • the material forming the anode 10 is not particularly limited, and those known in the art can be used.
  • Non-limiting examples thereof include metals such as vanadium, chromium, copper, zinc and gold; Alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al, SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; And carbon black.
  • metals such as vanadium, chromium, copper, zinc and gold
  • Alloys thereof Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al, SnO 2: a combination of a metal and an oxide such as S
  • the method for producing the anode 10 is not particularly limited, and can be produced according to a conventional method known in the art. For example, a method of coating a positive electrode material on a substrate made of a silicon wafer, quartz, a glass plate, a metal plate, or a plastic film can be mentioned.
  • the cathode 20 injects electrons into the organic material layer A.
  • the material forming the cathode 20 is not particularly limited, and those known in the art can be used. Non-limiting examples thereof include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; Alloys thereof; And multilayer structured materials such as LiF / Al and LiO 2 / Al.
  • the method for producing the cathode 20 is not particularly limited, and can be produced by a method known in the art.
  • the organic layer (A) included in the organic electroluminescent device according to the present invention can be used without limitation in a conventional structure used as an organic layer of a conventional organic EL device.
  • the hole transport region 30, the light emitting layer 40, And a transport region 50 can be included in the organic electroluminescent device according to the present invention.
  • the hole transporting region 30 included in the organic material layer A of the present invention serves to move the holes injected from the anode 10 to the light emitting layer 40.
  • the hole transporting region 30 may include at least one selected from the group consisting of a hole injecting layer 31 and a hole transporting layer 32. At this time, in consideration of the characteristics of the organic electroluminescent device, it is preferable that both the hole injection layer 31 and the hole transport layer 32 are included.
  • the material forming the hole injection layer 31 and the hole transport layer 32 is not particularly limited as long as the material has a low hole injection barrier and a high hole mobility and the hole injection layer / Can be used. At this time, the materials constituting the hole injection layer (31) and the hole transport layer (32) may be the same or different.
  • the hole injecting material may be any of the hole injecting materials known in the art.
  • usable hole injection materials include phthalocyanine compounds such as copper phthalocyanine; (N, N'-diphenyl-N, N'-bis- [4- (phenyl-m-tolyl-amino) -phenyl] -biphenyl-4,4'-diamine, m- , 4 "-tris (3-methylphenylphenylamino) triphenylamine), TDATA (4,4'4" -Tris (N, N-diphenylamino) triphenylamine), 2TNATA (naphthyl) -N-phenylamino ⁇ -triphenylamine, PEDOT / PSS, poly (4-styrenesulfonate), PANI / DBSA sulfonicacid, PANI / PSS (polyaniline) / poly (4-styrenesulfonate), etc.
  • the hole transporting material may be any one of known hole transporting materials.
  • usable hole transport materials include carbazole-based derivatives such as phenylcarbazole and polyvinylcarbazole, fluorene-based derivatives, N, N'-bis (3-methylphenyl) Triphenylamine derivatives such as N'-diphenyl- [1,1-biphenyl] -4,4'-diamine and TCTA (4,4 ', 4 "-tris (N-carbazolyl) triphenylamine) , N'-di (1-naphthyl) -N, N'-diphenylbenzidine) and TAPC (4,4'-Cyclohexylidene bis [N, Or two or more of them may be mixed.
  • the hole transporting region 30 may be manufactured by a conventional method known in the art. For example, a vacuum deposition method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging method (LITI)
  • a vacuum deposition method for example, a vacuum deposition method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging method (LITI)
  • the light emitting layer 40 included in the organic material layer A of the present invention is a layer in which excitons are formed by the combination of holes and electrons and the color of the light emitted by the organic electroluminescent device depends on the material constituting the light emitting layer 40 It can be different.
  • the light emitting layer (40) is made of a compound represented by the general formula (1) and a dopant.
  • the compound of Formula 1 is used as a phosphorescent host material (e.g., a first host) of the light emitting layer.
  • the compound represented by Formula 1 is a bipolar host material having both electronic characteristics and hole characteristics. More specifically a core having a nitrogen heteroaromatic ring (e.g., azine) and two dibenzo-based moieties (e.g., dibenzofuran or dibenzothiophene) bonded on both sides thereof, Has a basic skeleton in which at least one phenyl group of two dibenzo-based moieties is connected to an electron donating group (EDG) having a conventional electron donor in the art.
  • EDG electron donating group
  • the compound of the formula (1) has a dibenzo-type moiety (e.g., dibenzofuran (DBF), dibenzothiophene (DBT)) having both physicochemical properties for holes and electrons and an electron attracting moiety Pyrazine, triazine), which is a kind of azo group in the EWG group (e.g., pyridine, pyrazine, and triazine), and the dibenzo series moietiesecabazole, indolocarbazole, phenoxazine, phenoxathiazine, aryl An electron donor group such as amine is connected.
  • a dibenzo-type moiety e.g., dibenzofuran (DBF), dibenzothiophene (DBT) having both physicochemical properties for holes and electrons and an electron attracting moiety Pyrazine, triazine
  • EWG group e.g., pyridine, pyrazine, and triazine
  • the compound of Formula 1 is a bipolar compound, the recombination of holes and electrons is high, so that the hole injecting / transporting ability, luminous efficiency, driving voltage, lifetime characteristics, durability and the like can be improved. Accordingly, when the compound of Chemical Formula 1 is applied as a green phosphorescent material, not only can it have excellent luminous efficiency characteristics, but also can be driven at a low voltage and exhibit lifetime increasing effect, and can exhibit thermal stability, high glass transition temperature characteristics, (morphology). Since the organic EL device is also effective in inhibiting crystallization of the organic material layer, the performance and lifetime characteristics of the organic EL device including the compound can be greatly improved.
  • the planarity and stereoscopic property of the compound can be realized according to the bonding positions of two dibenzofurans or dibenzothiophene moieties bonded to azine groups.
  • the electron transporting ability is improved, and the driving and efficiency of the device to which these compounds are applied can be expected to be increased.
  • the dibenzofuran moiety or the dibenzothiophene moiety is more excellent in electron and hole stability than an aryl group, lifetime characteristics of a device to which such a compound is applied can be further improved.
  • EDG electron donor groups
  • carbazole groups indolocarbazoles, phenoxazines, phenoxathiazines, arylamine groups and the like
  • the HOMO level of the compound can be freely controlled.
  • the carbazole group is electrochemically stable and has a deep HOMO level by conjugation with other amines EDG.
  • the polycyclic electron donor (EDG) having a condensed ring and / or fused ring form has excellent thermal stability and electrochemical stability, has a high glass transition temperature (Tg) and excellent carrier transporting ability.
  • Tg glass transition temperature
  • the electron and hole transport mobility is very excellent, and the balance of the carriers in the light emitting layer is very excellent.
  • the host material should have a triplet energy gap higher than the dopant of the host. That is, in order to effectively provide phosphorescent emission from the dopant, the lowest excitation state of the host must be higher energy than the lowest emission state of the dopant.
  • the compound represented by Formula 1 has a high triplet energy and can be used as a host material because the energy level can be controlled higher than that of the dopant.
  • the compound represented by the formula (1) can prevent the excitons generated in the light emitting layer from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. Accordingly, the luminous efficiency of the device can be improved by increasing the number of the excitons contributing to the light emission in the light emitting layer, the durability and stability of the device can be improved, and the lifetime of the device can be efficiently increased.
  • the compound represented by the general formula (1) of the present invention has a core comprising an azine group and two dibenzo-based moieties (dibenzofuran or dibenzothiophene moiety) connected to both sides thereof, An aryl group and / or a heteroaryl group in which at least one electron donor group (EDG) is bonded to any one of six-membered rings in the core and substituted with at least one, specifically four or more deuterium (D)
  • EDG electron donor group
  • X 1 and X 2 are the same as or different from each other and each independently O or S. At this time, when d is 0, dibenzofuran moiety is formed, and in case of S, dibenzothiophene moiety can be formed.
  • Y 1 to Y 16 are the same as or different from each other, and each independently CR 8 or N; In this case, when there are a plurality of CR 8 s , the plurality of R 8 s may be the same or different.
  • the remaining is CR 8 ;
  • At least one of Y 13 to Y 16 is N, the remaining is CR 8 ;
  • At least one of Y 1 to Y 4 is N, and at least one of Y 9 to Y 12 is N, the remainder is CR 8 ;
  • At least one of Y 5 to Y 8 is N, and at least one of Y 13 to Y 16 is N, the remainder is CR 8 ;
  • At least one of Y 1 to Y 4 is N, and when one of Y 13 to Y 16 is N, the remaining is CR 8 ;
  • Y 1 to Y 16 may all be CR 8 (see the following formulas 13 to 17).
  • R 8 is hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, an amino group, an alkynyl group of C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of, C 3 ⁇ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ⁇ alkyloxy group of C 40, C 6 ⁇ C 60 aryloxy group, C group 1 ⁇ C 40 alkyl silyl, C 6 ⁇ C 60 aryl silyl group, a alkyl boronic of C 1 ⁇ C 40, an aryl boronic a C 6 ⁇ C 60, C 1 ⁇ C 40 phosphine groups, C 1 to C 40 phosphine oxide groups, and C 6 to C 60
  • R 8 is a hydrogen, a deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 of the A cycloalkyl group, and a C 6 to C 60 aryl group.
  • Z 1 to Z 3 are the same or different and are each independently CR 5 or N, and at least one of them is N. In one preferred embodiment, from 1 to 3 of Z 1 to Z 3 may be N, for example, pyridine, pyrimidine, triazine. More preferably, all of Z 1 to Z 3 are N and triazine is electron-withdrawing.
  • Ar 1 is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, C 3 to C 40 cycloalkyl, A C 6 to C 60 aryl group, and the like.
  • Ar 1 is preferably an aryl group of C 6 to C 60 , and may be, for example, a phenyl group, a biphenyl group, a naphthyl group, a triphenyl group, an anthryl group, a phenanthryl group and the like.
  • Ar 1 can be selected from the group of substituents represented by the following structural formulas. At this time, any hydrogen included in the following substituents may be substituted with at least one or more deuterium (D), or may be unsubstituted.
  • D deuterium
  • Ar 1 may be substituted with at least one substituent group known in the art (for example, the same definition as R 6 ).
  • a and c are each an integer of 0 to 3
  • b and d are an integer of 0 to 4, respectively.
  • hydrogen means not substituted with R 1 to R 4
  • a to d are each an integer of 1 or more, one or more hydrogen atoms are substituted with R 1 to R 4 . it means.
  • R 1 to R 5 are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the An alkynyl group, a C 3 to C 40 cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyl A C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6
  • R 1 to R 5 each are plural, they are the same as or different from each other. Specifically, R 1 to R 5 are the same or different and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 An alkynyl group of C 40 to C 40 , a cycloalkyl group of C 3 to C 40 , and an aryl group of C 6 to C 60 .
  • m and n are each an integer of 0 to 3, and m + n? 1.
  • m or n 0, it means that hydrogen is not substituted with A or B.
  • m and n are each an integer of 1 or more, it means that at least one hydrogen is substituted with A and B, respectively.
  • m and n may each be an integer of 0 to 2.
  • b + m and d + n may be an integer of 0 to 4, respectively.
  • a and B are electron donating substituents each of which serves to provide electrons.
  • an electron donating group (EDG) known in the art can be used without limitation.
  • a and B are each a carbazole group, a condensed ring or a fused ring-type polycyclic carbazole-based moiety (e.g., a condensed carbazole, an indolocarbazole, a biscarbazole), phenoxazine, phenoxathiazine, Amine group, and the like.
  • a and B are the same as or different from each other, and each independently may be any of the substituents represented by the above formulas (2) to (4).
  • X 3 is a single bond or may be selected from the group consisting of O, or S.
  • X 3 may be a carbazole group, a condensed ring and / or a polycyclic carbazole-based moiety in the form of a fused ring (for example, a condensed carbazole, an indolocarbazole, or the like) Of a bis-carbazole.
  • X < 3 > is O or S, phenoxazine or phenoxythiazine can be formed.
  • e is an integer of 0 to 4
  • f is an integer of 0 to 3.
  • hydrogen means not substituted by R 6 and R 7
  • e and f are each an integer of 1 or more, at least one hydrogen is substituted with R 6 and R 7 respectively .
  • R 6 and R 7 are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C 2 ⁇ C A C 3 to C 40 cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkenyl group, C 6 -C 60 aryloxy groups, C 1 -C 40 alkylsilyl groups, C 6 -C 60 arylsilyl groups, C 1 -C 40 alkylboron groups, C 6 -C 60 a group of the arylboronic, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ selected from the
  • R 6 and R 7 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, C 2 ⁇ C 40 A C 3 to C 40 cycloalkyl group, and a C 6 to C 60 aryl group, or may be bonded to adjacent groups to form a condensed ring.
  • adjacent groups may be one R 6 and one R 6 , one R 6 and one Ar 2 , one R 7 and another R 7 , one R 7, and one Ar 2 .
  • L may be a divalent group linker known in the art. Specifically, L is a single bond or an arylene group having 6 to 40 carbon atoms. When L is a C 6 to C 40 arylene group, it may be a phenylene group, a biphenylene group, a naphthylene group, a triphenylene group or the like, preferably a phenylene group or a biphenylene group.
  • Ar 2 and Ar 3 are the same or different and each independently represents a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkenyl group, group, C 3 ⁇ C 40 cycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C 6 ⁇ , or selected from the group consisting of an aryl amine of the C 60, or adjacent groups combined To form a condensed ring.
  • said Ar 2 and Ar 3 are the same or different from each other, and each independently C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C 6 ⁇ the group consisting of an aryl amine of the C 60 . ≪ / RTI >
  • a and B are the same as or different from each other, and each independently can be any one selected from the group of substituents represented by the following structural formulas.
  • any hydrogen contained in the following substituents may be substituted with at least one deuterium (D) or may be unsubstituted.
  • E is selected from the group consisting of O, S, NR 11 , CR 12 R 13 , and SiR 14 R 15 ,
  • a halogen atom, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a substituted or unsubstituted alkyl group having 5 to 5 nucleus atoms, wherein R 11 to R 15 are the same or different and each independently represents hydrogen, deuterium, Lt; / RTI > to 60, and < RTI ID 0.0 >
  • Ar 11 is hydrogen or a C 6 to C 60 aryl group
  • the compound represented by Formula 1 may include an aryl group and / or a heteroaryl group substituted by at least one deuterium (D) in the molecular structure.
  • at least one of Ar 1 , A, and B in Formula 1 is a C 6 to C 60 aryl group substituted with at least one deuterium (D), or a heteroaryl group having 5 to 50 nucleus atoms Group.
  • the number of deuterium (D) substituted in the compound is not particularly limited, and may be, for example, at least 1, preferably 4 or more. Specifically, it may be 1 to 18.
  • the compound containing a plurality of deuterium (D) can maximize the color purity of green more than the compounds having the same structure without deuterium, and further increase the intramolecular bonding force between the weakened carbon- Can be significantly improved.
  • the nitrogen-containing heterocycle having an EWG properties such as, Z 1 ⁇ Z 3 containing ring
  • EWG properties such as, Z 1 ⁇ Z 3 containing ring
  • X 1 hamyuhwan and X Symmetry or asymmetry structure depending on the carbon bond positions of the carbon-carbon double bonds.
  • the bonding position of one of Y 1 to Y 4 of the X 1 containing ring connected to the Z 1 to Z 3 containing ring and the bonding position of one of Y 9 to Y 12 of the X 2 containing ring are symmetrical or asymmetric Structure.
  • the carbon position of the X 1 -containing ring bonded to the azine group is Y 1
  • the X 2 -containing The carbon position of the ring may be any of Y 10 to Y 12 except Y 9 (see Chemical Formula 5 below).
  • the asymmetric structure of two dibenzo-based moieties respectively linked to the nitrogen-containing heterocycle may be represented by any one of the following formulas (5) to (8).
  • the ring containing Z 1 to Z 3 in Formula 5 is bonded to any one of Y 10 to Y 12 (provided that the ring containing Z 1 to Z 3 is not bonded to Y 9 )
  • the ring containing Z 1 to Z 3 in Formula 6 is bonded to any one of Y 9 and Y 11 to Y 12 (provided that the ring containing Z 1 to Z 3 is not bonded to Y 10 )
  • the Z 1 to Z 3 -containing ring of formula (7) is bonded to any one of Y 9 , Y 10 and Y 12 (provided that the Z 1 to Z 3 containing ring is not bonded to Y 11 )
  • the ring containing Z 1 to Z 3 in the above formula (8) is bonded to any one of Y 9 to Y 11 (provided that the ring containing Z 1 to Z 3 is not bonded to Y 12 ).
  • X 1 , X 2 , Y 1 to Y 16 , Z 1 to Z 3 , Ar 1 , m, n, A, B, a to d and R 1 to R 4 are as defined in Formula 1, respectively.
  • asymmetric compound In the case of the above-mentioned asymmetric compound, it is relatively easy to control the intermolecular distance as compared with the compound having a symmetric structure. That is, due to the nature of the dibenzo-based moiety capable of bonding at the 1,2,3,4-position, a structural disorder between the hydrogen of triazine and the dibenzo-based moiety occurs at the 1,4-bond, The distance will be farther away, which will also increase the T1 value. By using the above-mentioned characteristics, it is possible to adjust the HOMO-LUMO and T1 and S1 values of the organic material layer through the asymmetry of the chemical structure.
  • the compound represented by Formula 5 may be further represented by any one of Formulas 5a to 5c.
  • the compound represented by Formula 6 may be further represented by any one of Formulas 6a to 6c.
  • the compound represented by the above formula (7) may be further represented by any one of formulas (7a) to (7c).
  • the compound represented by the formula (8) may be further represented by any one of formulas (8a) to (8c).
  • X 1 , X 2 , Y 1 to Y 16 , Z 1 to Z 3 , Ar 1 , m, n, A, B, a to d and R 1 to R 4 are as defined in claim 1, respectively.
  • X 2- containing ring when the carbon position of the X 1 -containing ring bonded to the azine group (for example, a ring containing Z 1 to Z 3 ) is Y 1 , X 2- containing ring may be Y 9 (see Chemical Formula 9 below).
  • the symmetric structure of two dibenzo-based moieties respectively linked to the nitrogen-containing heterocycle may be represented by any one of the following formulas (9) to (12).
  • X 1 , X 2 , Y 1 to Y 16 , Z 1 to Z 3 , Ar 1 , m, n, A, B, a to d and R 1 to R 4 are as defined in Formula 1, respectively.
  • the degree of symmetry affects the HOMO-LUMO overlap. This can affect the T1 and S1 values, and if this difference is large, it also affects the TTA and singlet fission, so it is important to adjust it appropriately.
  • dibenzo-based moieties such as dibenzofurane or dibenzothiophene moiety may be further represented by any one of the following formulas (13) to (17).
  • X 1 , X 2 , Z 1 to Z 3 , Ar 1 , n, A and B are as defined in the above formula (1).
  • each of X 1 and X 2 is independently O or S, and Z 1 to Z 3 are each independently CR 5 or N, Is N.
  • Ar 1 is a C 6 to C 60 aryl group, and at least one of A and B may be selected from the substituent groups of A and B exemplified above.
  • the compounds represented by the formula (1) according to the present invention may be further represented by the following formulas (1) to (336). However, the compounds represented by formula (1) of the present invention are not limited by the following examples.
  • alkyl means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms.
  • alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.
  • alkenyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond.
  • alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • alkynyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond.
  • alkynyls include, but are not limited to, ethynyl, 2-propynyl, and the like.
  • Cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Aryl in the present invention means a monovalent substituent derived from a C6-C60 aromatic hydrocarbon having a single ring or a combination of two or more rings. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included.
  • heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • alkyloxy means a monovalent substituent group represented by R'O-, and R 'means alkyl having 1 to 40 carbon atoms.
  • alkyloxy may include linear, branched or cyclic structures. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.
  • aryloxy means a monovalent substituent represented by RO-, and R means aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • Alkylsilyl in the present invention refers to silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.
  • alkyl boron is boron substituted with alkyl having 1 to 40 carbon atoms
  • aryl boron means boron substituted with aryl having 6 to 60 carbon atoms.
  • arylphosphine means a phosphine substituted with aryl having 6 to 60 carbon atoms
  • arylphosphine oxide group means that phosphine substituted with aryl having 6 to 60 carbon atoms includes O do.
  • condensed rings means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • the compounds represented by formula (1) of the present invention can be prepared without limitation by methods known in the art. For example, various syntheses can be carried out by referring to the synthesis process of the following examples.
  • the at least one host constituting the light emitting layer 40 according to the present invention may further include a compound having a carbazole moiety.
  • the carbazole skeleton has electron donating group characteristics, which are electron donating and hole transporting properties.
  • Such a compound having a carbazole moiety can be used as a host material having a hole property (e.g., a second host), and can be mixed with a compound of the formula (1) having the above-described electronic characteristics as a light emitting layer component.
  • the compound having a carbazole moiety is not particularly limited as long as it has at least one carbazole moiety in the molecular structure.
  • the compound may be a carbazole in the non-condensed ring form, an indolocarbazole, a condensed carbazole, or a bis-carbazole in the form of two carbazoles linked.
  • the above-exemplified carbazole basic skeleton may be in a form in which at least one of various types of alkyl groups, aryl groups and / or heteroaryl groups is substituted.
  • carbazole skeletons when two or more carbazole skeletons are contained in the molecule, they have high hole transportability, and the molecular weight of the carbazole skeleton is significantly higher than that of one carbazole skeleton, so that it can have high thermal stability.
  • the thermal and electrical stability of the molecule itself can be enhanced through a rigid bonding structure.
  • the light emitting layer 40 of the present invention includes a host and a dopant doped in the host. . In this way, the energy efficiency can be improved in the process of energy transfer from the host to the dopant.
  • the at least one host includes a first host represented by Formula 1; And a second host having a carbazole moiety.
  • the mixing ratio between the first host and the second host is not particularly limited, and can be appropriately adjusted within the range known in the art. In one embodiment, the mixing ratio of the first host to the second host may be 20-80: 80-20, preferably 30-70: 70-30.
  • the light emitting layer 40 of the present invention may further include a host material known in the art.
  • a host material known in the art.
  • usable host materials include alkali metal complexes; Alkaline earth metal complex compounds; Or condensed aromatic ring derivatives.
  • the host material may be at least one selected from the group consisting of an aluminum complex compound, a beryllium complex compound, an anthracene derivative, a pyrene derivative, a triphenylene derivative, a carbazole derivative, a dibenzofuran derivative, Thiophene derivatives, or a combination of at least two of them.
  • the dopant contained in the light emitting layer 40 of the present invention can be any of those known in the art without limitation, and specifically, the LUMO energy level and / or the triplet energy level, as compared with the host material of the above- Is not particularly limited as long as it is a substance falling within a specific range as described above.
  • Nonlimiting examples of usable dopants include metal complex compounds including anthracene derivatives, pyrene derivatives, arylamine derivatives, iridium (Ir), and platinum (Pt).
  • An example of the dopant according to the present invention may be an iridium (Ir) complex having a LUMO energy level of 2.4 to 2.8 eV and a triplet energy (T1) of 2.3 to 2.45 eV.
  • the present invention is not particularly limited thereto.
  • the light emitting layer 40 of the present invention can prevent electrons from being reversely transferred to the host by the triplet energy (T1) level while being able to be smoothly supplied from the host to the dopant through the LUMO level,
  • the luminous efficiency and lifetime characteristics of the device can be improved at the same time. Accordingly, in the present invention, it is necessary to control the physical properties (for example, LUMO, triplet energy (T1)) of the host and the dopant mixed as the light emitting layer material respectively as follows.
  • the difference (LUMO H - LUMO D ) between the LUMO energy level (LUMO H ) of the compound represented by Formula 1 and the LUMO energy level (LUMO D ) of the dopant is 1.0 eV ≪ / RTI > Preferably greater than 0 and less than or equal to 0.65 eV, more preferably greater than 0 and less than or equal to 0.5 eV.
  • the triplet energy level of the compound represented by Formula 1 is higher than the triplet energy level of the dopant.
  • the triplet energy level (T1 H) of the compound represented by the formula (1) the difference between the triplet energy level (T1 D) of the dopant (T1 H - T1 D) may be in the range of 0.1 to 0.5 eV, Preferably 0.2 to 0.4 eV.
  • the triplet energy level of the compound represented by Formula 1 may be 2.5 eV or more, specifically 2.5 to 3.0 eV, and preferably 2.6 to 2.85 eV.
  • the dopant may be classified into a red dopant, a green dopant, and a blue dopant.
  • the red dopant, the green dopant, and the blue dopant commonly known in the art can be used without particular limitation.
  • red dopant examples include PtOEP (Pt (II) octaethylporphine: Pt (II) octaethylporphine), Ir (piq) 3 (tris (2-phenylisoquinoline) iridium: (2'-benzothienyl) -pyridinato-N, C3 ') iridium (acetylacetonate): Bis (2- N, C3 ') iridium (acetylacetonate)), or a mixture of two or more thereof.
  • PtOEP Pt (II) octaethylporphine
  • Ir (piq) 3 tris (2-phenylisoquinoline) iridium: (2'-benzothienyl) -pyridinato-N, C3 ') iridium (acet
  • green dopant examples include Ir (ppy) 3 (tris (2-phenylpyridine) iridium: tris (2-phenylpyridine) iridium), Ir (ppy) (Acetylacetonato) iridium (III): bis (2-phenylpyridine) (acetylacetato) iridium (III)), Ir (mppy) (2-benzothiazolyl) -1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H- [1] benzopyrano [ 6,7,8-ij] -quinolizin-11-one: 10- (2-benzothiazolyl) -1,1,7,7-tetramethyl-2,3,6,7, -tetrahydro- 5H, 11H- [1] benzopyrano [6,7,8-ij] -quinolizine-11-one), or a mixture of two or more thereof.
  • Nonlimiting examples of the blue dopant include bis [3,5-difluoro-2- (2-pyridyl) phenyl] (picolinato) iridium (III) (2-pyridyl) phenyl (picolinato) iridium (III)), (F2ppy) 2Ir (tmd), Ir (dfppz) 3, DPVBi (4,4'- yl) biphenyl: 4,4'-bis (2,2'-diphenylethen-1-yl) biphenyl), DPAVBi (4,4'-Bis [4- (diphenylamino) styryl] biphenyl: Bis (4-diphenylaminostyryl) biphenyl), TBPe (2,5,8,11-tetra-tert-butyl perylene: 2,5,8,11-tetra- Or a mixture of two or more of these.
  • the mixing ratio between the host and the dopant is not particularly limited and can be appropriately adjusted within the range known in the art.
  • the host may be included in the range of 70 to 99.9 wt%, and the dopant may be included in the range of 0.1 to 30 wt%. More specifically, when the light emitting layer 40 is blue fluorescence, green fluorescence, or red fluorescence, the host may be contained in the range of 80 to 99.9 wt%, and the dopant may be included in the range of 0.1 to 20 wt%.
  • the host may be included in the range of 70 to 99 wt% and the dopant may be included in the range of 1 to 30 wt%.
  • the light emitting layer 40 includes a red light emitting layer including a red phosphorescent material; A green light emitting layer including a green phosphorescent material; Or a blue light-emitting layer containing a blue phosphor or a blue phosphor.
  • a light emitting layer containing a green phosphorescent material Preferably a light emitting layer containing a green phosphorescent material.
  • the above-described light emitting layer 40 may be a single layer or a plurality of layers of two or more layers.
  • the organic electroluminescent device can emit light of various colors.
  • the present invention can provide an organic electroluminescent device having a plurality of luminescent layers made of different materials in series to form a mixed color.
  • the driving voltage of the device is increased, while the current value in the organic light emitting device is constant, thereby providing an organic electroluminescent device having improved luminous efficiency by the number of light emitting layers.
  • the electron transporting region 50 included in the organic material layer A serves to move electrons injected from the cathode 20 to the light emitting layer 40.
  • the electron transport region 50 may include at least one selected from the group consisting of the electron transport layer 51 and the electron injection layer 52. In consideration of the characteristics of the organic electroluminescent device, it is preferable to include both the electron transport layer 51 and the electron injection layer 52 described above.
  • the electron injection layer 52 can use an electron injection material which is easy to inject electrons and has a high electron mobility, without limitation.
  • usable electron injecting materials include the above-mentioned bipolar compounds, anthracene derivatives, heteroaromatic compounds, alkali metal complexes and the like. Specifically, LiF, Li2O, BaO, NaCl, CsF; Lanthanum metals such as Yb and the like; Or metal halides such as RbCl, RbI and the like, which may be used alone or in combination of two or more.
  • the electron transporting region 50 of the present invention may be co-deposited with an n-type dopant to facilitate the injection of electrons from the cathode.
  • the n-type dopant can be used without limitation in the alkali metal complexes known in the art, and examples thereof include alkali metals, alkaline earth metals and rare earth metals.
  • the electron transport region 50 can be manufactured by a conventional method known in the art. For example, a vacuum deposition method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging method (LITI)
  • a vacuum deposition method for example, a vacuum deposition method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging method (LITI)
  • the organic light emitting device 100 of the present invention may further include a light emitting auxiliary layer (not shown) disposed between the hole transporting region 30 and the light emitting layer 40.
  • the light emission assisting layer serves to regulate the thickness of the organic layer (A) while serving to transport holes, which are moved from the hole transporting region (30), to the light emitting layer (40).
  • This luminescent auxiliary layer has a high LUMO value and prevents electrons from migrating to the hole transport layer 32 and has a high triplet energy to prevent the exciton of the luminescent layer 40 from diffusing into the hole transport layer 32.
  • This luminescent auxiliary layer may include a hole transporting material and may be made of the same material as the hole transporting region. Further, the light-emission-assisting layers of the red, green, and blue organic light-emitting devices may be made of the same material.
  • the light-emitting auxiliary layer material is not particularly limited, and examples thereof include carbazole derivatives and arylamine derivatives.
  • Non-limiting examples of usable luminescent auxiliary layers include NPD (N, N-dinaphthyl-N, N'-diphenyl benzidine), TPD (N, N'-bis- (3-methylphenyl) phenyl-benzidine, s-TAD, and 4,4 ', 4 "-tris (N-3-methylphenyl-Nphenyl-amino) -triphenylamine. These may be used alone or in combination of two or more.
  • the light-emitting auxiliary layer may include a p-type dopant in addition to the above-described materials. As the p-type dopant, well-known p-type dopants used in the related art can be used.
  • the organic electroluminescent device 100 of the present invention may further include an electron transporting layer (not shown) disposed between the electron transporting region 50 and the light emitting layer 40.
  • the electron transporting layer can prevent the excitons or holes generated in the light emitting layer from diffusing into the electron transporting region.
  • the electron transporting layer may include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative (e.g., BCP), a heterocyclic derivative including nitrogen, and the like.
  • the electron transporting auxiliary layer may be formed by vacuum deposition, spin coating, casting, Langmuir-Blodgett, inkjet printing, laser printing, laser induced thermal imaging (LITI) ), But the present invention is not limited thereto.
  • the organic electroluminescent device 100 of the present invention may further include a capping layer (not shown) disposed on the cathode 20 described above.
  • the capping layer functions to protect the organic light emitting device and efficiently emit light generated in the organic layer to the outside.
  • the capping layer may be formed of tris-8-hydroxyquinoline aluminum (Alq3), ZnSe, 2,5-bis (6 '- (2' N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-bis [N- (1-naphthyl) biphenyl-4,4'-diamine (TPD), 1,1'-bis (di-4-tolylaminophenyl) cyclohexane (TAPC).
  • TPD 1,1'-bis (di-4-tolylaminophenyl) cyclohexane
  • TAPC 1,1'-bis (di-4-tolylaminophenyl) cyclohexane
  • Such a capping layer may be a single layer, but may include two or more layers having different refractive indexes so that the refractive index gradually changes while passing through the two or more layers.
  • the capping layer may be formed by a conventional method known in the art. For example, various methods such as a vacuum deposition method, a spin coating method, a casting method, or a Langmuir-Blodgett (LB) method may be used.
  • various methods such as a vacuum deposition method, a spin coating method, a casting method, or a Langmuir-Blodgett (LB) method may be used.
  • the organic light emitting device of the present invention including the above-described configuration can be manufactured according to a conventional method known in the art.
  • an organic light emitting device can be manufactured by vacuum-depositing a cathode material on a substrate, then vacuum-depositing a hole transporting material, a light emitting layer material, an electron transporting material, and a cathode material on the anode in this order .
  • the organic electroluminescent device 100 has a structure in which an anode 10, an organic material layer A and a cathode 20 are sequentially laminated and a structure is formed between the anode 10 and the organic material layer A or between the anode 20 ) And the organic material layer (A).
  • lifetime characteristics can be excellent because the lifetime of the initial brightness is increased while maintaining the maximum luminous efficiency.
  • bipolar compound according to the present invention compounds represented by the following GE-01 to GE-16 and Ir (ppy) 3 were prepared, and the LUMO and triplet energy of each compound described above were measured by methods known in the art Are shown in Table 1 below. CBP compounds were also used as controls.
  • the LUMO energy level of each compound was calculated from the difference between HOMO and energy gap.
  • the ionization potential was measured using a cyclic voltammetry (CV) method and the energy gap was measured with a UV spectrophotometer.
  • the triplet energies were prepared by dissolving the sample in a concentration of 10 -4 M in a 2-methylTHF solvent and measuring the phosphorescence spectrum at 77 K low temperature using liquid nitrogen.
  • the glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 ⁇ was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.
  • a solvent such as isopropyl alcohol, acetone, or methanol
  • a green organic EL device was fabricated in the same manner as in Example 1 except that CBP was used instead of the compound GE-1 as a luminescent host material in forming the light emitting layer.
  • Example 1 GE-1 0.53 0.33 5.21 515 52.1
  • Example 2 GE-2 0.54 0.36 5.43 516 51.8
  • Example 3 GE-3 0.12 0.31 5.17 515 54.3
  • Example 4 GE-4 0.14 0.29 5.24 515 53.8
  • Example 5 GE-5 0.46 0.28 4.62 516 55.5
  • Example 6 GE-6 0.54 0.25 4.72 517 58.7
  • Example 7 GE-7 0.25 0.26 4.55 516 62.1
  • Example 8 GE-8 0.32 0.24 4.56 515 61.8
  • Example 9 GE-9 0.33 0.24 5.64 516 56.6
  • Example 10 GE-10 0.39 0.32 5.51 516 51.1
  • Example 12 GE-12 0.42 0.29 5.43 518 52.7
  • Example 13 GE-13 0.22 0.26 4.57 517 60.7
  • Example 14 GE-14 0.30 0.28 5.12 515 57.1
  • Example 15 GE-15 0.22
  • the green organic EL devices of Examples 1 to 16 using the compound according to the present invention as a light emitting layer compared with the green organic EL device of Comparative Example 1 using conventional CBP, which is superior to the conventional method.
  • the CBP used in Comparative Example 1 is not smooth in the movement of electrons through the LUMO because the LUMO value difference with the dopant is larger than that of the present embodiments, and the CBP and dopant triplet energy (T1) Since the difference is insignificant compared to the compounds of the present embodiments, energy transfer from the dopant to CBP can be facilitated. As a result, it was found that the performance evaluation result of the green organic EL device of Comparative Example 1 including CBP as a light emitting layer material was not good.

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Abstract

La présente invention peut fournir un dispositif électroluminescent organique dans lequel un nouveau composé est utilisé en tant que matériau hôte pour une couche électroluminescente, et par conséquent le dispositif électroluminescent organique présente des propriétés améliorées telles qu'une efficacité d'émission de lumière élevée, une faible tension de commande et une longue durée de vie.
PCT/KR2019/000616 2018-01-16 2019-01-15 Dispositif électroluminescent organique WO2019143112A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008072596A1 (fr) * 2006-12-13 2008-06-19 Konica Minolta Holdings, Inc. Dispositif électroluminescent organique, dispositif d'affichage et d'éclairage
WO2013102992A1 (fr) * 2012-01-05 2013-07-11 出光興産株式会社 Matériau pour élément organique électroluminescent et élément utilisant ce matériau
KR20160028524A (ko) * 2014-05-05 2016-03-11 메르크 파텐트 게엠베하 유기 발광 소자용 재료
KR20170053590A (ko) * 2015-11-06 2017-05-16 희성소재 (주) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자
KR20170067671A (ko) * 2015-12-08 2017-06-16 희성소재 (주) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자
KR20170113321A (ko) * 2016-03-28 2017-10-12 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기 발광 소자

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008072596A1 (fr) * 2006-12-13 2008-06-19 Konica Minolta Holdings, Inc. Dispositif électroluminescent organique, dispositif d'affichage et d'éclairage
WO2013102992A1 (fr) * 2012-01-05 2013-07-11 出光興産株式会社 Matériau pour élément organique électroluminescent et élément utilisant ce matériau
KR20160028524A (ko) * 2014-05-05 2016-03-11 메르크 파텐트 게엠베하 유기 발광 소자용 재료
KR20170053590A (ko) * 2015-11-06 2017-05-16 희성소재 (주) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자
KR20170067671A (ko) * 2015-12-08 2017-06-16 희성소재 (주) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자
KR20170113321A (ko) * 2016-03-28 2017-10-12 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기 발광 소자

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