WO2016003054A1 - Nouveau composé et élément électroluminescent comprenant celui-ci - Google Patents

Nouveau composé et élément électroluminescent comprenant celui-ci Download PDF

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WO2016003054A1
WO2016003054A1 PCT/KR2015/003021 KR2015003021W WO2016003054A1 WO 2016003054 A1 WO2016003054 A1 WO 2016003054A1 KR 2015003021 W KR2015003021 W KR 2015003021W WO 2016003054 A1 WO2016003054 A1 WO 2016003054A1
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formula
group
light emitting
organic layer
layer
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최정옥
정준호
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주식회사 엘엠에스
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    • 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
    • H10K50/155—Hole transporting layers comprising dopants
    • 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
    • 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

Definitions

  • the present invention relates to a novel compound and a light emitting device comprising the same.
  • Organic Light-Emitting Diode is basically a structure in which an organic thin film including an organic light emitting layer is sandwiched between two electrodes, at least one of the two electrodes being transparent, and a suitable voltage between the two electrodes.
  • the organic light emitting diode is a kind of organic electronic device utilizing light emitted from the visible light region from the organic light emitting layer.
  • Such a light emitting device is basically a very thin device having a thickness of several micrometers or less, and is a self-light emitting device that emits light directly from the device itself. Therefore, the response speed is high and the viewing angle is wide as a display device.
  • the manufacturing process is simple, the flexible device using the organic thin film can be realized, and in addition to the vacuum process, in some cases, the device can be realized through the printing process from the solution state. Is getting.
  • the light emitting device has been applied as a component to be applied to a low current / low output mobile products, but in recent years, its application range has been gradually extended to the high current / high output field, high brightness / high reliability is required accordingly.
  • various methods for improving the luminous efficiency of light emitting devices have been studied.
  • Patent Document 1 relates to a light emitting device comprising PEDOT / PSS as a hole transport material, wherein the composition comprising PEDOT / PSS has a medium ionization potential slightly higher than 4.8 eV (between the ionization potential of the anode and the ionization potential of the light emitter). Median of This occurs as the composition induces holes injected from the anode to reach the HOMO level of the organic light emitting material or hole transport material.
  • Patent Document 2 relates to a composition containing PEDOT / PSS, the composition has the advantage that can be a solution process such as inkjet printing can be manufactured more easily.
  • the composition uses an excessive amount of PSS (i.e., an amount exceeding the amount required to stabilize the charge on the PEDOT), which not only prolongs the life of the light emitting device but also prevents the precipitation of the PSS from the PEDOT solution. have.
  • the composition used in the light emitting device has a strong acidity by including an excess of PSS, such a strong acid is etched indium tin oxide (ITO) to remove indium, tin and oxygen components Problems such as release into the PEDOT, degradation of the light emitting polymer, and the like.
  • ITO indium tin oxide
  • Patent Document 1 European Patent No. 0,686,662;
  • Patent Document 2 US Patent No. 6,605,823.
  • An object of the present invention is to provide a compound capable of improving the lifetime of light emission by increasing the luminous efficiency of the light emitting device and lowering the driving voltage.
  • Another object of the present invention is to provide a light emitting device having improved luminous efficiency and light emitting lifetime.
  • Another object of the present invention is to provide an electronic device including the light emitting device.
  • L a is an arylene group having 6 to 20 carbon atoms
  • Ar 1 and Ar 2 are each independently hydrogen or an aryl group having 6 to 30 carbon atoms
  • Any one or more of hydrogen contained in the aryl group having 6 to 30 carbon atoms is independently unsubstituted or substituted with Si (R) 3 , a cyano group, or a haloalkyl group having 1 to 4 carbon atoms,
  • R is an alkyl group having 1 to 4 carbon atoms
  • R 1 is hydrogen or an aryl group having 6 to 20 carbon atoms
  • a is 1 or 2.
  • a light emitting layer interposed between the first electrode and the second electrode;
  • the organic layer includes n organic layers including first to nth organic layers, wherein the first organic layer is formed at a position in contact with the light emitting layer, and the (n-1) organic layers except for the first organic layer are the first organic layer. And a structure laminated between the first electrode, n is an integer of 2 to 5,
  • the first organic layer provides a light emitting device including at least one compound represented by Chemical Formula 1.
  • the present invention provides an electronic device including the light emitting device.
  • the light emitting device has an excellent luminous efficiency and light emitting life by forming an organic layer including the compound represented by Formula 1 between the first electrode and the light emitting layer, so that the electronic device such as a display device and a lighting device using the light emitting device It can be used easily in the device.
  • the terms "comprises” or “having” are intended to indicate that there is a feature, number, step, operation, component, part, or combination thereof described in the specification, and one or more other features. It is to be understood that the present invention does not exclude the possibility of the presence or the addition of numbers, steps, operations, components, components, or a combination thereof.
  • alkyl group means a substituent derived from a saturated hydrocarbon in a linear or branched form.
  • alkyl group for example, methyl group (ethyl group), ethyl group (ethyl group), n-propyl group (n-propyl group), isopropyl group (iso-propyl group), n-butyl group (n -butyl group, sec-butyl group, t-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group (1,1- dimethylpropyl group), 1,2-dimethylpropyl group (1,2-dimethylpropyl group), 2,2-dimethylpropyl group (2,2-dimethylpropyl group), 1-ethylpropyl group (1-ethylpropyl group), 2- 2-ethylpropyl group, n-hexyl group, 1-methyl-2-ethylpropyl group, 1-ethyl-2-methylpropyl group (1-ethyl-2-methylpropyl group (1-ethyl
  • alkyl group may have 1 to 20 carbon atoms, for example, 1 to 12 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms.
  • aryl group means a monovalent substituent derived from an aromatic hydrocarbon.
  • the "aryl group” for example, a phenyl group (phenyl group), naphthyl group (naphthyl group), anthracenyl group (anthracenyl group), phenanthryl group naphthacenyl group (naphthacenyl group), pyrenyl group (pyrenyl group), tolyl group, biphenyl group, terphenyl group, terphenyl group, chrycenyl group, spirobifluorenyl group, spirobifluorenyl group, fluoranthenyl group group, fluorenyl group, perylenyl group, indenyl group, indenyl group, azulenyl group, heptarenyl group, heptanenyl group, phenalenyl group, Phenanthrenyl group etc. are mentioned.
  • aryl group may have 6 to 30 carbon atoms, for example, 6 to 18 carbon atoms, or 6 to 12 carbon atoms.
  • heteroaryl group means “aromatic heterocycle” or “heterocyclic” derived from a monocyclic or condensed ring.
  • the “heteroaryl group” is a hetero atom, at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se) and silicon (Si), for example, one, two Dogs, three or four.
  • the "heteroaryl group” for example, pyrrolyl group (pyrrolyl group), pyridyl group (pyridyl group), pyridazinyl group (pyridazinyl group), pyrimidinyl group (pyrimidinyl group), pyrazinyl group (pyrazinyl group) ), Triazolyl group, tetrazolyl group, benzotriazolyl group, benzotriazolyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group ( benzimidazolyl group, indolyl group, isoindolyl group, indodolyl group, indolinzinyl group, purinyl group, purinyl group, indazolyl group, quinolyl group ), Isoquinolinyl group (isoquinolinyl group), quinolizinyl group (quinolizinyl group), phthalazin
  • thiazolyl group (thiazolyl group), isothiazolyl group (isothiazolyl group), benzothiazolyl group (benzothiazolyl group), benzothiadiazolyl group (benzothiadiazolyl group), phenothia Phenothiazinyl group, isoxazolyl group, furazanyl group, furazanyl group, phenoxazinyl group, oxazolyl group, oxazolyl group, benzoxazolyl group, Oxadiazolyl group, pyrazoloxazolyl group, imidazothiazolyl group, thienofuranyl group, furopyrrolyl group, pyridoxazinyl group and compounds containing at least two or more heteroatoms such as (pyridoxazinyl group).
  • heteroaryl group may have 2 to 20 carbon atoms, for example, 3 to 19 carbon atoms, 4 to 15 carbon atoms, or 5 to 11 carbon atoms.
  • the heteroaryl group may have a ring member of 5 to 21.
  • cycloalkyl group means a substituent derived from a monocyclic saturated hydrocarbon.
  • cycloalkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloheptyl group, Cyclooctyl group etc. are mentioned.
  • cycloalkyl group may have 3 to 20 carbon atoms, for example, 3 to 12 carbon atoms, or 3 to 6 carbon atoms.
  • arylene group may mean a divalent substituent derived from the aryl group described above.
  • the present invention provides a light emitting device having improved luminous efficiency and light emitting lifetime and an electronic device including the same.
  • the light emitting devices developed to date have short light emitting lifetimes and low power efficiency.
  • various compounds have been developed as materials of the light emitting device, but there are limitations in manufacturing a light emitting device that satisfies both light emitting life and power efficiency.
  • the present invention forms an organic layer comprising a compound represented by Formula 1 according to the present invention between the first electrode and the light emitting layer to provide a light emitting device having improved luminous efficiency and light emitting life and an electronic device comprising the same. do.
  • the light emitting device according to the present invention forms an organic layer including the compound represented by Formula 1 between the first electrode and the light emitting layer, thereby having excellent light emitting efficiency and light emitting lifetime of the light emitting device. Therefore, the light emitting device according to the present invention can be usefully used for electronic devices such as display devices and lighting devices using the light emitting device.
  • L a is an arylene group having 6 to 20 carbon atoms
  • Ar 1 and Ar 2 are each independently hydrogen or an aryl group having 6 to 30 carbon atoms
  • Any one or more of hydrogen contained in the aryl group having 6 to 30 carbon atoms is independently unsubstituted or substituted with Si (R) 3 , a cyano group, or a haloalkyl group having 1 to 4 carbon atoms,
  • R is an alkyl group having 1 to 4 carbon atoms
  • R 1 is hydrogen or an aryl group having 6 to 20 carbon atoms
  • a is 1 or 2.
  • L a is a phenylene group or a naphthylene group
  • Ar 2 is hydrogen, a phenyl group, a biphenyl group, a naphthyl group or a phenanthryl group;
  • R 1 is hydrogen or a phenyl group
  • a may be 1 or 2.
  • Ar 1 may be a 1-naphthyl group.
  • the compound represented by Formula 1 may be selected from compounds having the structures of Formulas a-1 to a-36:
  • Ar 1 may be a 2-naphthyl group.
  • the compound represented by Formula 1 may be selected from compounds having the structures of Formulas b-1 to b-18:
  • Ar 1 may be a phenanthryl group.
  • the compound represented by Formula 1 may be selected from compounds having the structures of Formulas c-1 to c-36:
  • Ar 1 is trimethylsilyl group; Cyano group; Or a phenyl group substituted with a trifluoromethyl group.
  • the compound represented by Formula 1 may be selected from compounds having the structures of Formulas d-1 to d-4:
  • a light emitting layer interposed between the first electrode and the second electrode;
  • the organic layer includes n organic layers including first to nth organic layers, wherein the first organic layer is formed at a position in contact with the light emitting layer, and the (n-1) organic layers except for the first organic layer are the first organic layer. And a structure laminated between the first electrode, n is an integer of 2 to 5,
  • the first organic layer provides a light emitting device comprising at least one compound represented by Formula 1 below:
  • L a , Ar 1 , Ar 2 , R 1 , R 2 and a are as defined above.
  • the light emitting device As the application range of the light emitting device is expanded to the high current / high power field, it is required to increase the light emitting efficiency and the light emitting lifetime of the light emitting device. In this case, the light emission efficiency and light emission life can be improved only when the hole and the electron in the light emitting layer are smoothly combined.
  • electrons injected from the second electrode may overflow the light emitting layer to the hole transport layer, thereby reducing the coupling efficiency of holes and electrons in the light emitting layer. Therefore, in order to efficiently combine holes and electrons in the light emitting layer, the electrons injected from the second electrode must be prevented from leaving the light emitting layer, and the excitons formed in the light emitting layer must be prevented from being diffused or separated. .
  • the light emitting device may have a structure including an organic layer including a compound represented by Formula 1 between the first electrode and the light emitting layer.
  • the organic layer according to the present invention electrons injected from the second electrode may be introduced into the hole transport layer through the light emitting layer, or excitons formed in the light emitting layer may diffuse in the direction of the first electrode to prevent non-light emission.
  • the excitons formed in the light emitting layer can be prevented from disappearing non-light emission through an 'exciton dissociation' process at the interface between the light emitting layer and the hole transport layer.
  • the organic layer can maximize the generation efficiency and excitation of excitons in the light emitting layer by balancing charge in the light emitting layer, and as a result, the light emitting efficiency of the light emitting device is increased, As the driving voltage is lowered, light emission life can be improved.
  • Compound represented by the formula (1) according to the present invention introduces an arylene group as a linker (L a ) to N of the carbazole, and at the same time a multicyclic aryl group (Ar 1 ) in which two or more rings are fused to the arylene group, or Alternatively, the arylene group may have a structure in which a monocyclic aryl group (Ar 1 ) substituted with at least one of trimethylsilyl group, cyano group, and trifluoromethyl group is bonded.
  • the light emitting device including the compound represented by Formula 1 is superior to the light emitting device including a carbazole compound in which a linker (L a ) is not introduced or a single ring aryl group (Ar 1 ) is bonded. It may have a luminous efficiency and luminous lifetime (see Experimental Example 1).
  • FIG 1 and 2 are images showing a schematic structural cross-sectional view of a light emitting device according to the present invention.
  • the light emitting device may include an organic layer 108 having a multilayer structure of two or more layers between the first electrode 106 and the light emitting layer 102.
  • the first electrode 106 is a conductive material and is formed on the base substrate 107 to form an anode of the light emitting devices 100 to 100B. Play a role.
  • the first electrode 106 may be a transparent electrode or an opaque (reflective) electrode.
  • the first electrode 106 may include indium tin oxide (ITO), tin oxide (SnO 2 ), or the like.
  • the first electrode 106 may include an ITO / silver (Ag) / ITO structure.
  • the organic layer 108 is formed on the first electrode 106 to be positioned between the first electrode 106 and the light emitting layer 102. .
  • the organic layer 108 may include n organic layers including first to nth organic layers, wherein the first organic layer 103 may be formed at a position in contact with the light emitting layer 102.
  • (n-1) organic layers except for the first organic layer 103 are positioned between the first organic layer 103 and the first electrode 106, and the second organic layer and the third organic layer based on the first organic layer. , And may be laminated in the order of the fourth organic layer.
  • the first electrodes 106 may be sequentially stacked on the basis of the first organic layer 103.
  • the (n-1) organic layers except for the first organic layer 103 may serve as a hole transport layer and / or a hole injection layer.
  • the second organic layer 104 may serve as a hole transport layer.
  • the second organic layer 104 is, for example, 4,4-bis [N- (1-naphthyl) -N-phenyl-amine] biphenyl ( ⁇ -NPD), N, N-diphenyl- N, N-bis (3-methylphenyl) -1,1-biphenyl-4,4-diamine (TPD), poly- (N-vinylcarbazole) (PVCz) and the like may be included alone or in combination of two or more thereof. May be, but is not limited thereto.
  • the third organic layer 105 may serve as a hole injection layer.
  • the first electrode 106 and the second organic layer 104 is stacked between, for example, copper phthalocyanine (Copper phthalocyanine (CuPc)) may be included, but is not limited thereto.
  • CuPc copper phthalocyanine
  • the (n-1) organic layers may include a compound represented by the following Chemical Formula 3 as a hole transport compound:
  • R 2 and R 3 are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms;
  • L b is -L 1 -L 2 -L 3 -L 4- ,
  • L 1 , L 2 , L 3, and L 4 are each independently a single bond, —O—, —S—, an arylene group having 6 to 30 carbon atoms, a heteroarylene group having 2 to 20 carbon atoms, or 3 to 20 carbon atoms. Having cycloalkylene groups, except where L 1 , L 2 , L 3 and L 4 are all single bonds;
  • Ar 3 and Ar 4 are each independently an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, or a substituent represented by the following general formula (4),
  • X is O, S or C (R 6 ) (R 7 ),
  • R 4 , R 5 , R 6 and R 7 are each independently an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms,
  • p is an integer from 0 to 3
  • q is an integer of 0-4.
  • the hole transport compound represented by Chemical Formula 3 may be a compound represented by the following Chemical Formula 5:
  • R 2 is an aryl group having 6 to 30 carbon atoms
  • R 3 is hydrogen
  • L b is an arylene group having 6 to 20 carbon atoms
  • Ar 3 is an aryl group having 6 to 30 carbon atoms or a substituent represented by the following general formula (4),
  • X is O, S or C (R 6 ) (R 7 ),
  • R 4 , R 5 , R 6 and R 7 are each independently an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 30 carbon atoms,
  • p is an integer from 0 to 2
  • q is an integer of 0-2.
  • R 2 is a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group;
  • R 3 is hydrogen
  • L b is a phenylene group, a biphenylene group, a terphenylene group or a naphthylene group
  • Ar 3 may be a phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzothienyl group, dibenzofuranyl group, fluorenyl group, dimethylfluorenyl group or diphenylfluorenyl group.
  • the light emitting device includes a first organic layer 103 containing at least one compound represented by Chemical Formula 1;
  • a second organic layer 104 comprising a compound represented by Formula 3;
  • It may have a structure including a third organic layer 105 including a P-type dopant.
  • the second organic layer 104 may include a hole transport compound represented by Formula 3 as a hole transport compound together with the third organic layer 105, and the third organic layer 105 is a hole represented by the formula (3) P-type dopants may be included with the transport compound.
  • the third organic layer 105 includes a hole transport compound represented by Chemical Formula 3 as the hole transport compound, but the structure is the same as or different from the hole transport compound represented by Chemical Formula 3 included in the second organic layer 104 can do. More specifically, the hole transporting compounds constituting the second and third organic layers 104 and 105 may be hole transporting compounds represented by Formula 3, wherein R 2 , R 3 , L b , Ar 3, and Ar 4 Any one or more may be independent of each other. In this case, the compound constituting each of the second and third organic layers 104 and 105 may have a HOMO value for efficiently transferring holes to the emission layer 102.
  • the P-type dopant constituting the third organic layer 105 may include at least one P-type organic dopant or P-type inorganic dopant, and at least one P-type organic dopant and at least one P-type inorganic dopant It may include at the same time.
  • the P-type organic dopant for example, hexadecafluorophthalocyanine (F16CuPc), 11,11,12,12-tetracyanonaphtho-2,6-quinomimethane (11,11,12 , 12-tetracyanonaphtho-2,6-quinodimethane, TNAP), 3,6-difluoro-2,5,7,7,8,8-hexacyano-quinodimethane (3,6-difluoro-2, 5,7,7,8,8-hexacyano-quinodimethane, F2-HCNQ), tetracyanoquinodimethane (TCNQ), or the like, or a compound represented by the following Chemical Formulas 6 to 10:
  • R 8 is a cyano group, a sulfone group, a sulfoxide group, a sulfonamide group, a sulfonate group, a nitro group or a trifluoromethyl group,
  • n and n are independently of each other an integer from 1 to 5;
  • Y 1 and Y 2 are each independently an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms;
  • Hydrogen of the aryl and heteroaryl group is unsubstituted independently from each other; Or an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms, a hydroxy group or a halogen group.
  • the compound represented by Formula 10 may include a compound represented by Formula 10a or Formula 10b:
  • a metal oxide, a metal halide, etc. are mentioned, for example.
  • the content of the P-type dopant may be about 0.5 parts by weight to about 15 parts by weight, or about 0.5 parts by weight to about 5 parts by weight based on 100 parts by weight of the compound represented by Formula 3. Or about 1 part by weight to 10 parts by weight with respect to 100 parts by weight of the compound represented by Formula 3; 1 part by weight to 5 parts by weight; 1.5 parts by weight to 6 parts by weight; Or 2 parts by weight to 5 parts by weight.
  • the content of the P-type dopant is about 0.5 parts by weight to about 20 parts by weight with respect to 100 parts by weight of the compound represented by Formula 3, excessive leakage current may be achieved without reducing the physical properties of the compound represented by Formula 3 It can prevent occurrence.
  • the energy barrier at the interface with each of the upper and lower layers in contact with the third organic layer 105 may be reduced by the P-type dopant.
  • the first organic layer 103 may include a compound represented by Formula 1 below, and is located between the second organic layer 104 and the light emitting layer 102.
  • L a , Ar 1 , Ar 2 , R 1 and a are as defined above.
  • the light emitting efficiency and the light emitting life of the light emitting devices (100 to 100B) including the compound represented by the formula (1) in the first organic layer 103 according to the present invention was evaluated.
  • the light emitting device 100 including the compound represented by Chemical Formula 1 according to the present invention in the first organic layer 103 having a single layer structure has a light emission efficiency of 6.7 to 8.6 lm / W, and a light emission lifetime of 214 to 297. It appeared to be time.
  • the light emitting efficiency is 6.4 to 8.3 lm / W, and the light emitting lifetime is 211 to 279. It appeared to be time.
  • the compound represented by the formula (19) having a structure in which Ar 1 is directly connected without a linker (L a ) to the light emitting device and carbazole N containing a compound represented by the formula (18) wherein Ar 1 is a phenyl group in the first organic layer (103)
  • Ar 1 is a phenyl group in the first organic layer (103)
  • the light emitting devices 100 to 100B introduce an arylene group as a linker (L a ) to N of carbazole, and at the same time, a multicyclic aryl group (Ar 1) in which two or more rings are fused to the arylene group.
  • a linker (L a ) to N of carbazole
  • a multicyclic aryl group (Ar 1) in which two or more rings are fused to the arylene group.
  • the first organic layer 103 has a single layer structure including at least one compound represented by Chemical Formula 1, or as shown in FIG. 3, the upper layer 103a and the lower layer. It may be a two-layer structure including (103b).
  • the light emitting device 100B may include a first electrode 106, a third organic layer 105, and a second organic layer 104 formed on the base substrate 107.
  • the first organic layer 103a and 103b may have a two-layer structure.
  • both the upper layer 103a and the lower layer 103b of the first organic layer constituting the two-layer structure may include at least one compound represented by Formula 1, wherein The compound represented by Formula 1 included in each individual layer may have a different structure.
  • any one of the upper layer 103a and the lower layer 103b constituting the two-layer structure of the first organic layer 103 includes at least one compound represented by Formula 1, and the other layer is represented by Formula 2 below. It may have a structure comprising a compound represented by:
  • R a , R b , R c and R d are independently of each other hydrogen, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 14 carbon atoms.
  • the first organic layer 103 according to the present invention can increase the luminous efficiency by adjusting the thickness according to the resonance length of the light emitting device (100 to 100B), the exciton is an interface between the light emitting layer 102 and another layer
  • the exciton is an interface between the light emitting layer 102 and another layer
  • it is adjustable to be formed in the center portion of the light emitting layer 102, it is not particularly limited.
  • the first organic layer 103 dml structure when it is a single layer, it may have a thickness in the range of 20 kPa to 400 kPa, and in the case of the two-layer structure, each individual layer may have a thickness in the range of 10 kPa to 200 kPa. Can be.
  • the light emitting layer 102 is positioned between the first organic layer 103 and the second electrode 101, and the light emitting layer 102 emits light.
  • the wavelength may vary depending on the kind of the compound forming the light emitting layer 102.
  • the compound forming the light emitting layer 102 is not particularly limited as long as it is generally used in the art, and may be obtained commercially or manufactured and used.
  • the light emitting layer 102 when a current flows between the first electrode 106 and the second electrode 101, holes and second electrodes injected from the first electrode 106 are applied. Electrons injected from 101 combine to form excitons. In this case, the excitons may be singlet excitons, and may also be triplet excitons. Then, in the process of transition of the excitons to the ground state, light having a wavelength of a specific region is generated. Accordingly, the light emitting devices 100 to 100B may provide light to the outside.
  • the second electrode 101 is a conductive material and is disposed on the light emitting layer 102 to cathode the light emitting devices 100 to 100B. Play a role.
  • the second electrode 101 may include a metal such as nickel, magnesium, calcium, silver, aluminum, indium, or an alloy including two or more metals thereof, and more specifically, may include aluminum. .
  • the second electrode 101 may include a single layer structure or a multilayer structure of two or more layers.
  • the first electrode 106 is an opaque electrode
  • the second electrode 101 may be a transparent or translucent electrode, and in this case, the second electrode 101 may use an alloy containing magnesium and silver. , 100 ⁇ s to 150 ⁇ m in thickness.
  • the light emitting device 100 to 100B is an electron transporting layer between the light emitting layer 102 and the second electrode 101, an electron transporting layer (ETL) and / or electron injection layer (electron injecting) layer, EIL) (not shown) may be further included.
  • ETL electron transporting layer
  • EIL electron injection layer
  • the material for forming the electron transport layer or the electron injection layer is not particularly limited as long as it is generally used in the art, it can be obtained commercially or manufactured and used.
  • the light emitting devices 100 to 100B may further include an organic layer (not shown) positioned between the light emitting layer 102 and the second electrode 101. Can be.
  • the organic layer is positioned between the light emitting layer 102 and the second electrode 101, specifically, the light emitting layer 102 and the electron transport layer, and holes are transferred from the first electrode 106 to the electron transport layer via the light emitting layer 102. It may serve as a hole blocking layer (HBL) to prevent the inflow. In addition, the organic layer may serve as an exciton blocking layer that prevents excitons formed in the emission layer 102 in the direction of the second electrode 101 to prevent the excitons from non-emitting extinction. have.
  • HBL hole blocking layer
  • the organic layer may increase the luminous efficiency by adjusting the thickness according to the resonance length of the light emitting device (100 to 100B), the excitons are not the interface between the light emitting layer 102 and the other layer, the light emitting layer 102 It can be formed in the center of the.
  • the light emitting devices 100 to 100B according to the present invention may be manufactured by using a conventional deposition method using the first electrode 106, the organic layer 108, the light emitting layer 102, and the second electrode 101 described above.
  • a conventional deposition method using the first electrode 106, the organic layer 108, the light emitting layer 102, and the second electrode 101 described above.
  • any method commonly used in the art may be applied without limitation.
  • the present invention provides an electronic device including the light emitting device described above.
  • the electronic device according to the present invention may be a display device or a lighting device, but is not limited thereto.
  • the electronic device includes a light emitting device having an improved light emission efficiency and an improved light emission lifetime by introducing an organic layer including a compound represented by Formula 1 between the first electrode and the light emitting layer, thereby requiring high brightness and high reliability. It can also be used in high current / high power applications.
  • the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 50 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 20 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1a, 16.9 g, 90%) as a light gray solid.
  • THF tetrahydrofuran
  • the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 60 mL) and added to a 1 L reaction vessel containing methanol (320 mL). Thereafter, the mixture was stirred for 20 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1b, 23.8 g, 93%) as a light gray solid.
  • the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 55 mL) and added to a 1 L reaction vessel containing methanol (310 mL). Thereafter, the mixture was stirred for 20 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1c, 21.4 g, 91%) as a light gray solid.
  • the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 50 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 20 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1d, 17.7 g, 94%) as a light gray solid.
  • THF tetrahydrofuran
  • the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 50 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 20 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1e, 18.8 g, 92%) as a light gray solid.
  • THF tetrahydrofuran
  • the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 50 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 20 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1f, 20.5 g, 90%) as a light gray solid.
  • THF tetrahydrofuran
  • the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 50 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 20 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1g, 16.7 g, 92%) as a light gray solid.
  • THF tetrahydrofuran
  • the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 50 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 20 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1h, 18.3 g, 89%) as a light gray solid.
  • THF tetrahydrofuran
  • the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 50 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 20 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1i, 16.3 g, 86%) as a light gray solid.
  • THF tetrahydrofuran
  • the cooled reaction mixture was dissolved in tetrahydrofuran (THF, 50 mL) and added to a 1 L reaction vessel containing methanol (300 mL). Thereafter, the mixture was stirred for 20 minutes, and the resulting precipitate was filtered and collected to obtain a target compound (Formula 1j, 18.7 g, 87%) as a light gray solid.
  • THF tetrahydrofuran
  • Example 11-20 Fabrication of Light-Emitting Element comprising First Organic Layer of Single Layer Structure
  • ITO indium tin oxide
  • a compound represented by the following formula (11) as a host material was deposited at a rate of 1 ⁇ / sec and simultaneously a P-type dopant represented by the following formula (HAT-CN) ) was co-evaporated at a ratio of 3 parts by weight to 100 parts by weight of the host material to form a third organic layer having a thickness of 100 mm 3.
  • the compound represented by Formula 11 was deposited on the third organic layer to a thickness of 300 GPa to form a second organic layer.
  • the compounds prepared in Examples 1-10 were each deposited to a thickness of 100 GPa to form a first organic layer.
  • a compound represented by the following Chemical Formula 13 and a compound represented by Chemical Formula 14 were co-deposited on the first organic layer at a weight ratio of 100: 5 to form a light emitting layer having a thickness of 200 kHz.
  • a second electrode was formed of an aluminum thin film having a thickness of 1,000 ⁇ on the electron injection layer to manufacture a light emitting device including the first organic layer having a single layer structure.
  • Example 11 Compound of Formula 1a prepared in Example 1
  • Example 12 Compound of Formula 1b prepared in Example 2
  • Example 13 Compound of Formula 1c prepared in Example 3
  • Example 14 Compound of Formula 1d, prepared in Example 4
  • Example 15 Compound of Formula 1e prepared in Example 5
  • Example 16 Compound of Formula 1f prepared in Example 6
  • Example 17 Compound of Formula 1g prepared in Example 7
  • Example 18 Compound of Formula 1h prepared in Example 8
  • Example 19 Compound of Formula 1i prepared in Example 9
  • Example 20 Compounds of Formula 1j, prepared in Example 10
  • a compound represented by the above formula (11) is deposited as a host material at a rate of 1 ⁇ / sec and simultaneously a P-type dopant represented by the above formula (HAT-CN) ) Was co-evaporated at a ratio of 3 parts by weight to 100 parts by weight of the host material to form a third organic layer having a thickness of 100 mm 3.
  • the compound represented by Formula 11 was deposited on the third organic layer to a thickness of 300 GPa to form a second organic layer.
  • a compound represented by Chemical Formula 13 and a compound represented by Chemical Formula 14 were co-deposited at a weight ratio of 100: 5 on the upper layer of the first organic layer to form a light emitting layer having a thickness of 200 kHz.
  • the compound represented by Chemical Formula 15 and the compound represented by Chemical Formula 16 were co-deposited in a 50:50 weight ratio on the emission layer to form an electron transport layer having a thickness of 360 ⁇ . Subsequently, an electron injection layer having a thickness of 5 ⁇ was formed on the electron transport layer by using the compound represented by Formula 16.
  • a second electrode was formed of an aluminum thin film having a thickness of 1,000 ⁇ on the electron injection layer to manufacture a light emitting device including the first organic layer having a two-layer structure.
  • Example 21 Compound of formula 17 Compound of Example 1
  • Example 22 Compound of formula 17 Compound of Example 2
  • Example 23 Compound of formula 17 Compound of Example 3
  • Example 24 Compound of formula 17 Compound of Example 4
  • Example 25 Compound of formula 17 Compound of Example 5
  • Example 26 Compound of formula 17 Compound of Example 6
  • Example 27 Compound of formula 17 Compound of Example 7
  • Example 28 Compound of formula 17 Compound of Example 8
  • Example 29 Compound of formula 17 Compound of Example 9
  • Example 30 Compound of formula 17 Compound of Example 10
  • a compound represented by the above formula (11) is deposited as a host material at a rate of 1 s / sec and simultaneously a P-type dopant represented by the above formula (HAT-CN) Was co-evaporated at a rate of 3 parts by weight based on 100 parts by weight of the host material to form a third organic layer having a thickness of 100 mm 3.
  • the compound represented by Formula 11 was deposited on the third organic layer to a thickness of 300 GPa to form a second organic layer.
  • the compound (Formula 1g) prepared in Example 7 was deposited to form a lower layer of the first organic layer, and then Examples 1-6 and Example were formed on the lower layer.
  • Compounds prepared in 8-10 were respectively deposited to form an upper layer of the first organic layer. At this time, the thickness of the upper layer and the lower layer is 50 kPa each.
  • a compound represented by Chemical Formula 13 and a compound represented by Chemical Formula 14 were co-deposited at a weight ratio of 100: 5 on the upper layer of the first organic layer to form a light emitting layer having a thickness of 200 kHz.
  • the compound represented by Chemical Formula 15 and the compound represented by Chemical Formula 16 were co-deposited in a 50:50 weight ratio on the emission layer to form an electron transport layer having a thickness of 360 ⁇ . Subsequently, an electron injection layer having a thickness of 5 ⁇ was formed on the electron transport layer by using the compound represented by Formula 16.
  • a second electrode was formed of an aluminum thin film having a thickness of 1,000 ⁇ on the electron injection layer to manufacture a light emitting device including the first organic layer having a two-layer structure.
  • Example 31 Compound of Example 7 Compound of Example 1
  • Example 32 Compound of Example 7 Compound of Example 2
  • Example 33 Compound of Example 7 Compound of Example 3
  • Example 34 Compound of Example 7 Compound of Example 4
  • Example 35 Compound of Example 7 Compound of Example 5
  • Example 36 Compound of Example 7 Compound of Example 6
  • Example 37 Compound of Example 7 Compound of Example 8
  • Example 38 Compound of Example 7 Compound of Example 9
  • Example 39 Compound of Example 7 Compound of Example 10
  • Example 11 except that the first organic layer is formed by using the compound represented by Chemical Formula 18 instead of forming the first organic layer using the compound prepared in Example 1 (Formula 1a).
  • a light emitting device including a first organic layer having a single layer structure was prepared in the same manner as in 11.
  • Example 11 except that the first organic layer is formed by using the compound represented by Chemical Formula 19 instead of forming the first organic layer using the compound prepared in Example 1 (Formula 1a), A light emitting device including a first organic layer having a single layer structure was prepared in the same manner as in 11.
  • Example 21 except that the upper layer of the first organic layer using the compound represented by Formula 18 instead of forming the upper layer of the first organic layer using the compound prepared in Example 1 (Formula 1a) In the same manner as in Example 21, a light emitting device including a first organic layer having a two-layer structure was manufactured.
  • Example 21 instead of forming the upper layer of the first organic layer using a compound prepared in Example 1 (Formula 1a) except that the upper layer of the first organic layer using a compound represented by the formula (19) In the same manner as in Example 21, a light emitting device including a first organic layer having a two-layer structure was manufactured.
  • the bonded light emitting device was irradiated with UV light and cured, and the luminous efficiency of the cured light emitting device was measured.
  • the luminous efficiency was measured based on the value when the luminance is 1,000 cd / m 2 , and the unit of the measured value is lm / W.
  • T 50 means a time taken until the luminance of the light emitting device becomes 50% of the initial luminance.
  • the value for lifetime can be converted to the expected lifetime when measured under different measurement conditions on the basis of conversion equations known to those skilled in the art.
  • the first organic layer is composed of a single layer, but the first organic layer of the single layer is configured to include the compound of the present invention represented by Chemical Formula 1.
  • Table 5 shows the light emission efficiency and the light emitting life of the light emitting device according to Examples 21-39.
  • the light emitting device according to Examples 21 to 39 has a structure including a first organic layer having a two-layer structure.
  • Examples 21 to 30 are the case in which only one layer of the two layers of the first organic layer is configured to include the compound of Formula 1 according to the present invention (two-layer structure case 1), and the light emission according to Examples 31 to 39
  • the device is a case where both layers of the first organic layer are configured to include the compound of formula 1 according to the present invention (two-layer structure case 2).
  • the light emitting device including the first organic layer having a single layer structure the light emitting device comprising a compound represented by Formula 1 according to the present invention in the first organic layer has a luminous efficiency of 6.7 to 8.6 lm / W
  • the light emission lifetime was found to be 214 to 297 hours.
  • a phenylene group is introduced into the carbazole N as a linker (L a ), and a light emitting device and a trimethylsilyl group containing a compound of Formula 1d containing a polycyclic aryl group (Ar 1 ) in which two or more rings are fused are substituted.
  • the light emitting device and the light emitting lifetime of the light emitting device including the compound of Formula 1g were remarkably excellent at 8.5 and 8.6 lm / W and 284 and 297 hours, respectively.
  • the luminous efficiency is about 1.20 compared to the light emitting device including the compound of Formula 18 in which the Ar 1 is a phenyl group in the first organic layer. It is confirmed that the light emission life is increased by about 1.18 to 1.63 times.
  • a compound of Formula 19 having a structure in which an aryl group (Ar 1 ) is directly connected to N of carbazole without a linker (L a ) may be compared with a light emitting device including in a first organic layer. It can be seen that the luminous efficiency is increased by about 1.14 to 1.46 times, and the emission life is improved by about 1.20 to 1.66 times.
  • the light emitting device including the first organic layer having a two-layer structure includes a light emitting device (2 layer) comprising the compound of Formula 1 according to the present invention Structural case 1) was found to have a luminous efficiency of 6.2 to 8.2 m / W and a light emitting lifetime of 205 to 283 hours.
  • the light emitting device (two-layer structure case 2) including both the first organic layer of the two-layer structure according to the present invention (2 layer structure case 2) has a light emission efficiency of 6.4 to 8.3 m / W, the light emission lifetime is 211 to 279 hours Appeared.
  • the luminous efficiency is 5.8 lm / W
  • the emission lifetime is 198 hours
  • a light emitting device comprising a compound of Formula 19 having a structure in which the aryl group (Ar 1 ) is directly connected to N of the carbazole without a linker (L a )
  • the luminous efficiency and light emission were 6.1 lm / W and 189 hours, respectively.
  • the luminous efficiency is increased by about 1.10 to 1.43 times as compared with the light emitting device (Comparative Example 3) using the compound represented by Formula 18, wherein Ar 1 is a phenyl group. It can be seen that the light emission life is improved by about 1.07 to 1.41 times. In addition, the luminous efficiency was about 1.05 to 1.36 times as compared with the light emitting device (Comparative Example 4) using the compound of Formula 19 having a structure in which the aryl group (Ar 1 ) is directly connected to N of carbazole without a linker (L a ). It can be seen that the light emission lifetime is increased by about 1.12 to 1.48 times.
  • both the 'two-layer structure case 1' and the 'two-layer structure case 2' have a linker (L a ) to the light emitting device (Comparative Example 3) and carbazole N using the compound represented by Formula 18, wherein Ar 1 is a phenyl group. It can be seen that the light emitting efficiency and the light emitting lifetime are remarkably improved in comparison with the light emitting device (Comparative Example 4) using the compound of Formula 19 having a structure in which the aryl group (Ar 1 ) is directly connected.
  • This result has a symmetrical structure and introduces an arylene group as a linker (L a ) to N of the carbazole, and at the same time, a polycyclic aryl group (Ar 1 ) having two or more rings fused to the arylene group is bonded or the aryl.
  • a compound represented by the formula ( 1 ) according to the present invention in which a monocyclic aryl group (Ar 1 ) substituted with at least one of a trimethylsilyl group, a cyano group, and a trifluoromethyl group in a ethylene group is bonded to an organic layer introduced between the first electrode and the light emitting layer. It can be seen that the effect induced by the introduction.
  • the light emitting device in which the first organic layer having the single layer structure including the compound of Formula 1 according to the present invention is formed than the light emitting devices of the 'two-layer structure case 1' and the 'two-layer structure case 2', has luminous efficiency and light emission It can be seen that the effect of improving the life is more excellent.
  • the light emitting device of Examples 11-20 in which the first organic layer having a single layer structure is formed It can be seen that the luminous efficiency and the light emitting lifetime are excellent as compared with the light emitting device of Examples 21-30 using the same compound in the upper layer of the first organic layer.
  • the light emitting device of Examples 11 to 20 in which the first organic layer having a single layer structure is formed includes the same compound on the upper layer of the first organic layer, It can be seen that the luminous efficiency and the light emitting lifetime are excellent as compared with the light emitting device in which the lower layer of the first organic layer is formed of the compound of 7.
  • the 'two layer formed by the compound of formula 1 having both the upper and lower layers of the first organic layer having a different structure It can be seen that the light emitting device of the structure case 2 'is superior to the light emitting device of the' two layer structure case 1 'in which only the upper layer of the first organic layer has luminous efficiency and light emitting lifetime.
  • the first organic layer formed in the light emitting device is formed in a two-layer structure, it is better to use the compound of formula 1 according to the present invention in both layers than in one layer of the two-layer structure. And it can be seen that the effect of improving the light emitting life is more excellent.
  • the light emitting device forms an organic layer including the compound represented by Formula 1 between the first electrode and the light emitting layer, and thus has a high luminous efficiency and a light emitting life, so that a high current / high power field requiring high brightness / high reliability is required. It can be usefully used in the electronic device of the.

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  • Organic Chemistry (AREA)
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  • Physics & Mathematics (AREA)
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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention porte sur un élément électroluminescent, comprenant : une première électrode ; une seconde électrode en regard de la première électrode ; une couche électroluminescente intercalée entre la première électrode et la seconde électrode ; et une couche organique intercalée entre la première électrode et la couche électroluminescente, la couche organique comprenant n couches organiques, qui comprennent une première couche organique à une n ième couche organique, la première couche organique étant formée et positionnée pour venir contre la couche électroluminescente, les (n-1) couches organiques, à l'exclusion de la première couche organique, étant empilées entre la première couche organique et la première électrode, n représentant un nombre entier de 2 à 5 et la première couche organique comprenant au moins une sorte de composé représenté par la formule chimique 1.
PCT/KR2015/003021 2014-07-03 2015-03-27 Nouveau composé et élément électroluminescent comprenant celui-ci WO2016003054A1 (fr)

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WO2016116497A1 (fr) * 2015-01-20 2016-07-28 Cynora Gmbh Molécules organiques destinées en particulier à être utilisées dans des composants optoélectroniques

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WO2016116521A1 (fr) * 2015-01-20 2016-07-28 Cynora Gmbh Molécules organiques à utiliser en particulier dans des composants optoélectroniques

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JP2005154412A (ja) * 2003-09-05 2005-06-16 Ricoh Co Ltd ３，６−ジフェニルカルバゾール誘導体
KR20110034984A (ko) * 2009-09-29 2011-04-06 에스에프씨 주식회사 방향족 화합물 및 이를 이용한 유기전계발광소자

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
JP2005154412A (ja) * 2003-09-05 2005-06-16 Ricoh Co Ltd ３，６−ジフェニルカルバゾール誘導体
KR20110034984A (ko) * 2009-09-29 2011-04-06 에스에프씨 주식회사 방향족 화합물 및 이를 이용한 유기전계발광소자

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016116497A1 (fr) * 2015-01-20 2016-07-28 Cynora Gmbh Molécules organiques destinées en particulier à être utilisées dans des composants optoélectroniques
US10669473B2 (en) 2015-01-20 2020-06-02 Cynora Gmbh Organic molecules for use in optoelectronic components

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