WO2016003054A1 - Novel compound and light-emitting element comprising same - Google Patents

Novel compound and light-emitting element comprising same Download PDF

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Publication number
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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PCT/KR2015/003021
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French (fr)
Korean (ko)
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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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Abstract

A light-emitting element according to the present invention comprises: a first electrode; a second electrode facing the first electrode; a light-emitting layer interposed between the first electrode and the second electrode; and an organic layer interposed between the first electrode and the light-emitting layer, wherein the organic layer comprises n organic layers, which include a first organic layer to a n th organic layer, the first organic layer is formed and positioned to abut the light-emitting layer, the (n-1) organic layers, excluding the first organic layer, are stacked between the first organic layer and the first electrode, n is an integer of 2 to 5, and the first organic layer includes at least one kind of compound represented by chemical formula 1.

Description

신규한 화합물 및 이를 포함하는 발광소자Novel compound and light emitting device comprising the same
본 발명은 신규한 화합물 및 이를 포함하는 발광소자에 관한 것이다.The present invention relates to a novel compound and a light emitting device comprising the same.
발광소자(Organic Light-Emitting Diode; OLED)는 기본적으로 두 개의 전극 사이에 유기 발광층을 포함하는 유기 박막이 샌드위치 되어 있는 구조로서, 두 전극 중 최소 하나의 전극은 투명하고, 두 전극 사이에 적당한 전압, 일반적으로 직류 5 내지 10 V 사이의 전압이 인가되면 유기 발광층에서 가시광선 영역의 빛이 나오는 것을 활용한 일종의 유기 전자 소자이다.Organic Light-Emitting Diode (OLED) 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. In general, when a voltage of 5 to 10 V DC is applied, 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.
이와 같은 발광소자는 기본적으로 전극을 포함한 실제 소자의 두께가 수 마이크로미터 이하로 매우 얇고, 소자 자체에서 직접 빛이 나오는 자발광소자이므로, 이에 따른 응답 속도가 빠르며, 표시 소자로서 시야각이 넓다. 또한, 제조 공정이 간단하고, 유기 박막을 이용한 유연한 소자의 구현이 가능하며, 진공 공정뿐만 아니라 경우에 따라서는 용액 상태로부터 인쇄 공정을 통한 소자의 구현이 가능하므로 차세대 표시소자 및 조명 측면에서 많은 주목을 받고 있다.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. In addition, since 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.
종래, 발광소자는 저전류/저출력의 모바일 제품에 적용되는 부품으로 적용되었으나, 최근 들어 점차 그 활용범위가 고전류/고출력 분야로 확대되고 있으며, 이에 따른 고휘도/고신뢰성이 요구되고 있다. 이러한 추세에 따라 발광소자의 발광효율을 향상시키기 위한 다양한 방법이 연구되고 있다.Conventionally, 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. In accordance with this trend, various methods for improving the luminous efficiency of light emitting devices have been studied.
현재까지 진행된 연구결과들을 살펴보면, 다음과 같다:The results of the research so far are as follows:
먼저, 특허문헌 1은 PEDOT/PSS를 정공수송물질로서 포함하는 발광소자에 관한 것으로, 상기 PEDOT/PSS를 포함하는 조성물은 4.8eV보다 약간 높은 중간 이온화 전위(애노드의 이온화 전위와 발광체의 이온화 전위 사이의 중간값)를 제공한다. 이는 상기 조성물이 애노드로부터 주입된 정공을 유기발광물질 또는 정공수송물질의 HOMO준위에 도달하도록 유도함에 따라 발생된다.First, 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.
다음으로, 특허문헌 2는 PEDOT/PSS를 포함하는 조성물에 관한 것으로, 상기 조성물은 잉크젯 프린팅 등의 용액공정이 가능하여 디바이스를 보다 쉽게 제조할 수 있는 이점이 있다. 더불어, 상기 조성물은 과량의 PSS(즉, PEDOT 상의 전하를 안정화하는데 요구되는 양보다 과도한 양)를 사용하므로, 발광소자의 수명을 연장시킬 수 있을 뿐만 아니라 PEDOT 용액으로부터 PSS가 석출되는 것을 방지할 수 있다.Next, 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. In addition, 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.
그러나, 상기 특허문헌의 1에 따른 발광소자의 경우, 발광층 물질로 사용되는 유기물의 LUMO 에너지 준위에 비하여 PEDOT/PSS의 LUMO 에너지 준위가 낮기 때문에 고효율 장수명의 발광소자 제조에 어려움이 있다. 또한, 특허문헌 2의 경우, 발광소자에 사용되는 조성물은 과량의 PSS를 포함함으로써 강한 산성을 띄게 되는데, 이러한 강산은 인듐 틴 옥사이드(indium tin oxide, ITO)를 식각시켜 인듐, 주석 및 산소 성분을 PEDOT 내로 방출시키거나, 발광 중합체를 열화시키는 등의 문제를 야기할 수 있다.However, in the light emitting device according to Patent Document 1, since the LUMO energy level of PEDOT / PSS is lower than the LUMO energy level of the organic material used as the light emitting layer material, it is difficult to manufacture a high efficiency long life light emitting device. In addition, in the case of Patent Document 2, 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.
상술한 바와 같이, 종래 발광소자의 발광효율 및 발광수명을 개선하기 위한 연구는 지속적으로 이루어져 왔다. 그러나, 현재까지 개발된 발광소자 및 발광소자에 사용되는 화합물은 고전류/고출력 분야에서 사용하기에는 그 효과가 미미하므로, 이를 해결할 수 있는 대안이 절실히 요구되고 있다.As described above, studies to improve the luminous efficiency and the light emitting life of the conventional light emitting device have been continuously made. However, the light emitting device and the compound used in the light emitting device developed to date have a minimal effect for use in the field of high current / high power, there is an urgent need for an alternative to solve this problem.
[특허문헌][Patent Documents]
(특허문헌 1) 유럽특허 제0,686,662호;(Patent Document 1) European Patent No. 0,686,662;
(특허문헌 2) 미국특허 제6,605,823호.(Patent Document 2) US Patent No. 6,605,823.
본 발명의 목적은 발광소자의 발광효율 증대 및 구동전압 저하를 통하여 발광수명의 개선이 가능한 화합물을 제공하는데 있다.SUMMARY OF THE INVENTION 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.
본 발명의 다른 목적은 발광효율 및 발광수명이 향상된 발광소자를 제공하는데 있다.Another object of the present invention is to provide a light emitting device having improved luminous efficiency and light emitting lifetime.
본 발명의 또 다른 목적은 상기 발광소자를 포함하는 전자장치를 제공하는데 있다.Another object of the present invention is to provide an electronic device including the light emitting device.
상기 목적을 달성하기 위하여,In order to achieve the above object,
본 발명은 하나의 실시예에서,The invention in one embodiment,
하기 화학식 1로 나타내는 화합물을 제공한다:There is provided a compound represented by the formula:
[화학식 1][Formula 1]
Figure PCTKR2015003021-appb-I000001
Figure PCTKR2015003021-appb-I000001
상기 화학식 1에 있어서,In Chemical Formula 1,
La는 탄소수 6 내지 20을 갖는 아릴렌기이고;L a is an arylene group having 6 to 20 carbon atoms;
Ar1 및 Ar2는 서로 독립적으로 수소 또는 탄소수 6 내지 30을 갖는 아릴기이며,Ar 1 and Ar 2 are each independently hydrogen or an aryl group having 6 to 30 carbon atoms,
상기 탄소수 6 내지 30을 갖는 아릴기에 함유된 수소 중 어느 하나 이상은, 서로 독립적으로 Si(R)3, 시아노기, 또는 탄소수 1 내지 4를 갖는 할로알킬기로 치환되거나 비치환되고,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,
상기 R은 탄소수 1 내지 4를 갖는 알킬기이며;R is an alkyl group having 1 to 4 carbon atoms;
R1은 수소 또는 탄소수 6 내지 20을 갖는 아릴기이고; 및R 1 is hydrogen or an aryl group having 6 to 20 carbon atoms; And
a는 1 또는 2이다.a is 1 or 2.
또한, 본 발명은 하나의 실시예에서,In addition, the present invention in one embodiment,
제1 전극;A first electrode;
제1 전극에 대향된 제2 전극;A second electrode opposed to the first electrode;
제1 전극과 제2 전극 사이에 개재된 발광층; 및A light emitting layer interposed between the first electrode and the second electrode; And
제1 전극과 발광층 사이에 개재되는 유기층을 포함하고,An organic layer interposed between the first electrode and the light emitting layer,
상기 유기층은 제1 유기층 내지 제n 유기층으로 구성되는 n개의 유기층을 포함하며, 여기서, 제1 유기층은 발광층과 접하는 위치에 형성되고, 제1 유기층을 제외한 (n-1)개의 유기층은 제1 유기층과 제1 전극 사이에 적층되는 구조이며, n은 2 내지 5의 정수이고,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,
상기 제1 유기층은 상기 화학식 1로 나타내는 화합물을 1종 이상 포함하는 발광소자를 제공한다.The first organic layer provides a light emitting device including at least one compound represented by Chemical Formula 1.
나아가, 본 발명은 하나의 실시예에서, 상기 발광소자를 포함하는 전자장치를 제공한다.Furthermore, in one embodiment, the present invention provides an electronic device including the light emitting device.
본 발명에 따른 발광소자는 제1 전극과 발광층 사이에 화학식 1로 나타내는 화합물을 포함하는 유기층을 형성함으로써, 우수한 발광효율 및 발광수명을 가지므로, 발광소자를 사용하는 디스플레이 장치, 조명 장치 등의 전자 장치에 용이하게 사용할 수 있다.The light emitting device according to the present invention 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.
도 1은 본 발명에 따른 하나의 실시예에서 제조되는 발광소자(n=2인 경우)의 구조를 도시한 이미지이다;1 is an image showing the structure of a light emitting device (when n = 2) manufactured in one embodiment according to the present invention;
도 2는 본 발명에 따른 다른 실시예에서 제조되는 발광소자(n=3인 경우)의 구조를 도시한 이미지이다;2 is an image showing the structure of a light emitting device (when n = 3) manufactured in another embodiment according to the present invention;
도 3은 본 발명에 따른 또 다른 실시예에서 제조되는 발광소자(n=3인 경우)의 구조를 도시한 이미지이다.3 is an image showing the structure of a light emitting device (when n = 3) manufactured in another embodiment according to the present invention.
본 발명은 다양한 변경을 가할 수 있고 여러 가지 실시예를 가질 수 있는 바, 특정 실시예들을 도면에 예시하고 상세한 설명에 상세하게 설명하고자 한다.As the invention allows for various changes and numerous embodiments, particular embodiments will be illustrated in the drawings and described in detail in the written description.
그러나, 이는 본 발명을 특정한 실시 형태에 대해 한정하려는 것이 아니며, 본 발명의 사상 및 기술 범위에 포함되는 모든 변경, 균등물 내지 대체물을 포함하는 것으로 이해되어야 한다.However, this is not intended to limit the present invention to specific embodiments, it should be understood to include all modifications, equivalents, and substitutes included in the spirit and scope of the present invention.
본 발명에서, "포함한다" 또는 "가지다" 등의 용어는 명세서상에 기재된 특징, 숫자, 단계, 동작, 구성요소, 부품 또는 이들을 조합한 것이 존재함을 지정하려는 것이지, 하나 또는 그 이상의 다른 특징들이나 숫자, 단계, 동작, 구성요소, 부품 또는 이들을 조합한 것들의 존재 또는 부가 가능성을 미리 배제하지 않는 것으로 이해되어야 한다.In the present invention, 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.
또한, 본 발명에서 첨부된 도면은 설명의 편의를 위하여 확대 또는 축소하여 도시된 것으로 이해되어야 한다.In addition, it is to be understood that the accompanying drawings in the present invention are shown to be enlarged or reduced for convenience of description.
이하, 본 발명에 대하여 도면을 참고하여 상세하게 설명하고, 도면 부호에 관계없이 동일하거나 대응하는 구성 요소는 동일한 참조 번호를 부여하고 이에 대한 중복되는 설명은 생략하기로 한다.Hereinafter, the present invention will be described in detail with reference to the accompanying drawings, and the same or corresponding components will be given the same reference numerals regardless of the reference numerals, and redundant description thereof will be omitted.
본 발명에서, "알킬기"란 직쇄(linear) 또는 분지(branched) 형태의 포화 탄화수소로부터 유도된 치환기를 의미한다.In the present invention, "alkyl group" means a substituent derived from a saturated hydrocarbon in a linear or branched form.
이때, 상기 "알킬기"로는 예를 들면, 메틸기(methyl group), 에틸기(ethyl group), n-프로필기(n-propyl group), 이소프로필기(iso-propyl group), n-부틸기(n-butyl group), sec-부틸기(sec-butyl group), t-부틸기(tert-butyl group), n-펜틸기(n-pentyl group), 1,1-디메틸프로필기(1,1-dimethylpropyl group), 1,2-디메틸프로필기(1,2-dimethylpropyl group), 2,2-디메틸프로필기(2,2-dimethylpropyl group), 1-에틸프로필기(1-ethylpropyl group), 2-에틸프로필기(2-ethylpropyl group), n-헥실기(n-hexyl group), 1-메틸-2-에틸프로필기(1-methyl-2-ethylpropyl group), 1-에틸-2-메틸프로필기(1-ethyl-2-methylpropyl group), 1,1,2-트리메틸프로필기(1,1,2-trimethylpropyl group), 1-프로필프로필기(1-propylpropyl group), 1-메틸부틸기(1-methylbutyl group), 2-메틸부틸기(2-methylbutyl group), 1,1-디메틸부틸기(1,1-dimethylbutyl group), 1,2-디메틸부틸기(1,2-dimethylbutyl group), 2,2-디메틸부틸기(2,2-dimethylbutyl group), 1,3-디메틸부틸기(1,3-dimethylbutyl group), 2,3-디메틸부틸기(2,3-dimethylbutyl group), 2-에틸부틸기(2-ethylbutyl group), 2-메틸펜틸기(2-methylpentyl group), 3-메틸펜틸기(3-methylpentyl group) 등을 들 수 있다.At this time, as the "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), 1,1,2-trimethylpropyl group, 1-propylpropyl group, 1-methylbutyl group (1 -methylbutyl group), 2-methylbutyl group, 1,1-dimethylbutyl group (1,1-dimethylbutyl group), 1,2-dimethylbutyl group (1,2-dimethylbutyl group), 2 , 2-dimethylbutyl group (2,2-dimet hylbutyl group), 1,3-dimethylbutyl group (1,3-dimethylbutyl group), 2,3-dimethylbutyl group (2,3-dimethylbutyl group), 2-ethylbutyl group (2-ethylbutyl group), 2- Methyl pentyl group (2-methylpentyl group), 3-methylpentyl group, etc. are mentioned.
또한, 상기 "알킬기"는 1 내지 20의 탄소수, 예를 들어 1 내지 12의 탄소수, 1 내지 6의 탄소수, 또는 1 내지 4의 탄소수를 가질 수 있다.In addition, the "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.
본 발명에서, "아릴기"란 방향족 탄화수소로부터 유도된 1가의 치환기를 의미한다.In the present invention, "aryl group" means a monovalent substituent derived from an aromatic hydrocarbon.
이때, 상기 "아릴기"로는 예를 들면, 페닐기(phenyl group), 나프틸기(naphthyl group), 안트라세닐기(anthracenyl group), 페난트릴기(phenanthryl group) 나프타세닐기(naphthacenyl group), 피레닐기(pyrenyl group), 톨릴기(tolyl group), 바이페닐기(biphenyl group), 터페닐기(terphenyl group), 크리세닐기(chrycenyl group), 스피로바이플루오레닐기(spirobifluorenyl group), 플루오란테닐기(fluoranthenyl group), 플루오레닐기(fluorenyl group), 페릴레닐기(perylenyl group), 인데닐기(indenyl group), 아줄레닐기(azulenyl group), 헵타레닐기(heptalenyl group), 페날레닐기(phenalenyl group), 페난트레닐기(phenanthrenyl group) 등을 들 수 있다.At this time, 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.
또한, 상기 "아릴기"는 6 내지 30의 탄소수, 예를 들어 6 내지 18의 탄소수, 또는 6 내지 12의 탄소수를 가질 수 있다.In addition, the "aryl group" may have 6 to 30 carbon atoms, for example, 6 to 18 carbon atoms, or 6 to 12 carbon atoms.
본 발명에서, "헤테로아릴기"란 단환 또는 축합환으로부터 유도된 "방향족 복소환" 또는 "헤테로사이클릭"을 의미한다. 상기 "헤테로아릴기"는 헤테로원자로서 질소(N), 황(S), 산소(O), 인(P), 셀레늄(Se) 및 규소(Si) 중에서 적어도 하나, 예를 들어 1개, 2개, 3개 또는 4개를 포함할 수 있다.In the present invention, "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.
이때, 상기 "헤테로아릴기"로는 예를 들면, 피롤릴기(pyrrolyl group), 피리딜기(pyridyl group), 피리다지닐기(pyridazinyl group), 피리미디닐기(pyrimidinyl group), 피라지닐기(pyrazinyl group), 트리아졸릴기(triazolyl group), 테트라졸릴기(tetrazolyl group), 벤조트리아졸릴기(benzotriazolyl group), 피라졸릴기(pyrazolyl group), 이미다졸릴기(imidazolyl group), 벤즈이미다졸릴기(benzimidazolyl group), 인돌릴기(indolyl group), 이소인돌릴기(isoindolyl group), 인돌리지닐기(indolizinyl group), 푸리닐기(purinyl group), 인다졸릴기(indazolyl group), 퀴놀릴기(quinolyl group), 이소퀴놀리닐기(isoquinolinyl group), 퀴놀리지닐기(quinolizinyl group), 프탈라지닐기(phthalazinyl group), 나프틸리디닐기(naphthylidinyl group), 퀴녹살리닐기(quinoxalinyl group), 퀴나졸리닐기(quinazolinyl group), 신놀리닐기(cinnolinyl group), 프테리디닐기(pteridinyl group), 이미다조트리아지닐기(imidazotriazinyl group), 아크리디닐기(acridinyl group), 페난트리디닐기(phenanthridinyl group), 카바졸릴기(carbazolyl group), 카바졸리닐기(carbazolinyl group), 피리미디닐기(pyrimidinyl group), 페난트롤리닐기(phenanthrolinyl group), 페나지닐기(phenazinyl group), 이미다조피리디닐기(imidazopyridinyl group), 이미다조피리미디닐기(imidazopyrimidinyl group), 피라졸로피리디닐기(pyrazolopyridinyl group) 등을 포함하는 함질소 헤테로아릴기; 티에닐기(thienyl group), 벤조티에닐기(benzothienyl group), 디벤조티에닐기(dibenzothienyl group) 등을 포함하는 황 함유 헤테로아릴기; 퓨릴기(furyl group), 피라닐기(pyranyl group), 사이클로펜타피라닐기(cyclopentapyranyl group), 벤조퓨라닐기(benzofuranyl group), 이소벤조퓨라닐기(isobenzofuranyl group), 디벤조퓨라닐기(dibenzofuranyl group) 등을 포함하는 함산소 헤테로아릴기 등을 들 수 있다.In this case, 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), phthalazinyl group (phthalazinyl group), naphthylidinyl group, quinoxalinyl group (quinoxalinyl group), quinazolinyl group ( quinazolinyl group, cinnolinyl group, pteridinyl group, already Zotriazinyl group (imidazotriazinyl group), acridinyl group (acridinyl group), phenanthridinyl group (phenanthridinyl group), carbazolyl group, carbazolinyl group (carbazolinyl group), pyrimidinyl group, Phenanthrolinyl group (phenanthrolinyl group), phenazinyl group (phenazinyl group), imidazopyridinyl group (imidazopyridinyl group), imidazopyrimidinyl group, pyrazolopyridinyl group (pyrazolopyridinyl group) Nitrogen heteroaryl groups; Sulfur-containing heteroaryl groups including thienyl group, benzothienyl group, dibenzothienyl group and the like; Furyl group, pyranyl group, cyclopentapyranyl group, cyclopentapyranyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group and dibenzofuranyl group An oxygen-containing heteroaryl group etc. which are included are mentioned.
또한, 상기 "헤테로아릴기"의 구체적인 예로서는, 티아졸릴기(thiazolyl group), 이소티아졸릴기(isothiazolyl group), 벤조티아졸릴기(benzothiazolyl group), 벤조티아디아졸릴기(benzothiadiazolyl group), 페노티아지닐기(phenothiazinyl group), 이소옥사졸릴기(isoxazolyl group), 퓨라자닐기(furazanyl group), 페녹사지닐기(phenoxazinyl group), 옥사졸릴기(oxazolyl group), 벤조옥사졸릴기(benzoxazolyl group), 옥사다이아졸릴기(oxadiazolyl group), 피라졸로옥사졸릴기(pyrazoloxazolyl group), 이미다조티아졸릴기(imidazothiazolyl group), 티에노퓨라닐기(thienofuranyl group), 퓨로피롤릴기(furopyrrolyl group), 피리독사지닐기(pyridoxazinyl group) 등의 적어도 2개 이상의 헤테로원자를 포함하는 화합물들을 들 수 있다.In addition, as a specific example of the "heteroaryl group", 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).
또한, 상기 "헤테로아릴기"는 2 내지 20의 탄소수, 예를 들어 3 내지 19의 탄소수, 4 내지 15의 탄소수 또는 5 내지 11의 탄소수를 가질 수 있다. 예를 들어, 헤테로원자를 포함하면, 헤테로아릴기는 5 내지 21의 환원(ring member)을 가질 수 있다.In addition, the "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. For example, when including a heteroatom, the heteroaryl group may have a ring member of 5 to 21.
본 발명에서, "사이클로알킬기"란 단일고리(monocyclic)의 포화 탄화수소로부터 유도된 치환기를 의미한다.In the present invention, "cycloalkyl group" means a substituent derived from a monocyclic saturated hydrocarbon.
상기 "사이클로알킬기"로는 예를 들면, 사이클로프로필기(cyclopropyl group), 사이클로부틸기(cyclobutyl group), 사이클로펜틸기(cyclopentyl group), 사이클로헥실기(cyclohexyl group), 사이클로헵틸기(cycloheptyl group), 사이클로옥틸기(cyclooctyl group) 등을 들 수 있다.Examples of the "cycloalkyl group" include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cycloheptyl group, Cyclooctyl group etc. are mentioned.
또한, 상기 "사이클로알킬기"는 3 내지 20의 탄소수, 예를 들어 3 내지 12의 탄소수, 또는 3 내지 6의 탄소수를 가질 수 있다.In addition, the "cycloalkyl group" may have 3 to 20 carbon atoms, for example, 3 to 12 carbon atoms, or 3 to 6 carbon atoms.
본 발명에서, "아릴렌기"란 상기에서 설명한 아릴기로부터 유도된 2가의 치환기를 의미할 수 있다.In the present invention, "arylene group" may mean a divalent substituent derived from the aryl group described above.
본 발명은 발광효율과 발광수명이 향상된 발광소자 및 이를 포함하는 전자장치를 제공한다.The present invention provides a light emitting device having improved luminous efficiency and light emitting lifetime and an electronic device including the same.
현재까지 개발된 발광소자는 발광수명이 짧고 전력 효율이 낮은 문제점이 있다. 이와 같은 문제점들을 해결하기 위해서, 발광소자의 재료로서 다양한 화합물들이 개발되고 있지만 발광수명 및 전력 효율을 모두 만족시키는 발광소자를 제조하는데 한계가 있다.The light emitting devices developed to date have short light emitting lifetimes and low power efficiency. In order to solve these problems, 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.
이러한 문제를 해결하기 위하여, 본 발명은 제1 전극과 발광층 사이에 본 발명에 따른 화학식 1로 나타내는 화합물을 포함하는 유기층을 형성하여 발광효율과 발광수명이 향상된 발광소자 및 이를 포함하는 전자장치를 제공한다. 본 발명에 따른 발광소자는 제1 전극과 발광층 사이에 화학식 1로 나타내는 화합물을 포함하는 유기층을 형성함으로써, 발광소자의 우수한 발광효율 및 발광수명을 가진다. 따라서, 본 발명에 따른 발광소자는 발광소자가 사용되는 디스플레이 장치, 조명 장치 등의 전자장치에 유용하게 사용할 수 있다.In order to solve this problem, 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.
이하, 본 발명을 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명은 하나의 실시예에서,The invention in one embodiment,
하기 화학식 1로 나타내는 화합물을 제공한다:There is provided a compound represented by the formula:
[화학식 1][Formula 1]
Figure PCTKR2015003021-appb-I000002
Figure PCTKR2015003021-appb-I000002
상기 화학식 1에 있어서,In Chemical Formula 1,
La는 탄소수 6 내지 20을 갖는 아릴렌기이고;L a is an arylene group having 6 to 20 carbon atoms;
Ar1 및 Ar2는 서로 독립적으로 수소 또는 탄소수 6 내지 30을 갖는 아릴기이며,Ar 1 and Ar 2 are each independently hydrogen or an aryl group having 6 to 30 carbon atoms,
상기 탄소수 6 내지 30을 갖는 아릴기에 함유된 수소 중 어느 하나 이상은, 서로 독립적으로 Si(R)3, 시아노기, 또는 탄소수 1 내지 4를 갖는 할로알킬기로 치환되거나 비치환되고,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,
상기 R은 탄소수 1 내지 4를 갖는 알킬기이며;R is an alkyl group having 1 to 4 carbon atoms;
R1은 수소 또는 탄소수 6 내지 20을 갖는 아릴기이고; 및R 1 is hydrogen or an aryl group having 6 to 20 carbon atoms; And
a는 1 또는 2이다.a is 1 or 2.
구체적으로, 본 발명에 따른 화학식 1로 나타내는 화합물에 있어서,Specifically, in the compound represented by Formula 1 according to the present invention,
상기 La는 페닐렌기 또는 나프틸렌기이고;L a is a phenylene group or a naphthylene group;
Ar2는 수소, 페닐기, 바이페닐기, 나프틸기 또는 페난트릴기이며;Ar 2 is hydrogen, a phenyl group, a biphenyl group, a naphthyl group or a phenanthryl group;
R1은 수소 또는 페닐기이고; 및R 1 is hydrogen or a phenyl group; And
a는 1 또는 2일 수 있다.a may be 1 or 2.
이때, 본 발명에 따른 상기 화학식 1로 나타내는 화합물에 있어서,At this time, in the compound represented by Formula 1 according to the present invention,
상기 Ar1은 1-나프틸기일 수 있다.Ar 1 may be a 1-naphthyl group.
보다 구체적으로, 상기 화학식 1로 나타내는 화합물은 하기 화학식 a-1 내지 a-36의 구조를 갖는 화합물로부터 선택될 수 있다:More specifically, the compound represented by Formula 1 may be selected from compounds having the structures of Formulas a-1 to a-36:
<화학식 a-1> <Formula a-1>
Figure PCTKR2015003021-appb-I000003
Figure PCTKR2015003021-appb-I000003
<화학식 a-2> <Formula a-2>
Figure PCTKR2015003021-appb-I000004
Figure PCTKR2015003021-appb-I000004
<화학식 a-3> <Formula a-3>
Figure PCTKR2015003021-appb-I000005
Figure PCTKR2015003021-appb-I000005
<화학식 a-4> <Formula a-4>
Figure PCTKR2015003021-appb-I000006
Figure PCTKR2015003021-appb-I000006
<화학식 a-5> <Formula a-5>
Figure PCTKR2015003021-appb-I000007
Figure PCTKR2015003021-appb-I000007
<화학식 a-6> <Formula a-6>
Figure PCTKR2015003021-appb-I000008
Figure PCTKR2015003021-appb-I000008
<화학식 a-7> <Formula a-7>
Figure PCTKR2015003021-appb-I000009
Figure PCTKR2015003021-appb-I000009
<화학식 a-8> <Formula a-8>
Figure PCTKR2015003021-appb-I000010
Figure PCTKR2015003021-appb-I000010
<화학식 a-9> <Formula a-9>
Figure PCTKR2015003021-appb-I000011
Figure PCTKR2015003021-appb-I000011
<화학식 a-10> <Formula a-10>
Figure PCTKR2015003021-appb-I000012
Figure PCTKR2015003021-appb-I000012
<화학식 a-11> <Formula a-11>
Figure PCTKR2015003021-appb-I000013
Figure PCTKR2015003021-appb-I000013
<화학식 a-12> <Formula a-12>
Figure PCTKR2015003021-appb-I000014
Figure PCTKR2015003021-appb-I000014
<화학식 a-13> <Formula a-13>
Figure PCTKR2015003021-appb-I000015
Figure PCTKR2015003021-appb-I000015
<화학식 a-14> <Formula a-14>
Figure PCTKR2015003021-appb-I000016
Figure PCTKR2015003021-appb-I000016
<화학식 a-15> <Formula a-15>
Figure PCTKR2015003021-appb-I000017
Figure PCTKR2015003021-appb-I000017
<화학식 a-16> <Formula a-16>
Figure PCTKR2015003021-appb-I000018
Figure PCTKR2015003021-appb-I000018
<화학식 a-17> <Formula a-17>
Figure PCTKR2015003021-appb-I000019
Figure PCTKR2015003021-appb-I000019
<화학식 a-18> <Formula a-18>
Figure PCTKR2015003021-appb-I000020
Figure PCTKR2015003021-appb-I000020
<화학식 a-19> <Formula a-19>
Figure PCTKR2015003021-appb-I000021
Figure PCTKR2015003021-appb-I000021
<화학식 a-20> <Formula a-20>
Figure PCTKR2015003021-appb-I000022
Figure PCTKR2015003021-appb-I000022
<화학식 a-21> <Formula a-21>
Figure PCTKR2015003021-appb-I000023
Figure PCTKR2015003021-appb-I000023
<화학식 a-22> <Formula a-22>
Figure PCTKR2015003021-appb-I000024
Figure PCTKR2015003021-appb-I000024
<화학식 a-23> <Formula a-23>
Figure PCTKR2015003021-appb-I000025
Figure PCTKR2015003021-appb-I000025
<화학식 a-24> <Formula a-24>
Figure PCTKR2015003021-appb-I000026
Figure PCTKR2015003021-appb-I000026
<화학식 a-25> <Formula a-25>
Figure PCTKR2015003021-appb-I000027
Figure PCTKR2015003021-appb-I000027
<화학식 a-26> <Formula a-26>
Figure PCTKR2015003021-appb-I000028
Figure PCTKR2015003021-appb-I000028
<화학식 a-27> <Formula a-27>
Figure PCTKR2015003021-appb-I000029
Figure PCTKR2015003021-appb-I000029
<화학식 a-28> <Formula a-28>
Figure PCTKR2015003021-appb-I000030
Figure PCTKR2015003021-appb-I000030
<화학식 a-29> <Formula a-29>
Figure PCTKR2015003021-appb-I000031
Figure PCTKR2015003021-appb-I000031
<화학식 a-30> <Formula a-30>
Figure PCTKR2015003021-appb-I000032
Figure PCTKR2015003021-appb-I000032
<화학식 a-31> <Formula a-31>
Figure PCTKR2015003021-appb-I000033
Figure PCTKR2015003021-appb-I000033
<화학식 a-32> <Formula a-32>
Figure PCTKR2015003021-appb-I000034
Figure PCTKR2015003021-appb-I000034
<화학식 a-33> <Formula a-33>
Figure PCTKR2015003021-appb-I000035
Figure PCTKR2015003021-appb-I000035
<화학식 a-34> <Formula a-34>
Figure PCTKR2015003021-appb-I000036
Figure PCTKR2015003021-appb-I000036
<화학식 a-35> <Formula a-35>
Figure PCTKR2015003021-appb-I000037
Figure PCTKR2015003021-appb-I000037
<화학식 a-36><Formula a-36>
Figure PCTKR2015003021-appb-I000038
.
Figure PCTKR2015003021-appb-I000038
.
또한, 본 발명에 따른 화학식 1로 나타내는 화합물에 있어서,In addition, in the compound represented by Formula 1 according to the present invention,
상기 Ar1은 2-나프틸기일 수 있다.Ar 1 may be a 2-naphthyl group.
보다 구체적으로, 상기 화학식 1로 나타내는 화합물은 하기 화학식 b-1 내지 b-18의 구조를 갖는 화합물로부터 선택될 수 있다:More specifically, the compound represented by Formula 1 may be selected from compounds having the structures of Formulas b-1 to b-18:
<화학식 b-1> <Formula b-1>
Figure PCTKR2015003021-appb-I000039
Figure PCTKR2015003021-appb-I000039
<화학식 b-2> <Formula b-2>
Figure PCTKR2015003021-appb-I000040
Figure PCTKR2015003021-appb-I000040
<화학식 b-3> <Formula b-3>
Figure PCTKR2015003021-appb-I000041
Figure PCTKR2015003021-appb-I000041
<화학식 b-4> <Formula b-4>
Figure PCTKR2015003021-appb-I000042
Figure PCTKR2015003021-appb-I000042
<화학식 b-5> <Formula b-5>
Figure PCTKR2015003021-appb-I000043
Figure PCTKR2015003021-appb-I000043
<화학식 b-6> <Formula b-6>
Figure PCTKR2015003021-appb-I000044
Figure PCTKR2015003021-appb-I000044
<화학식 b-7> <Formula b-7>
Figure PCTKR2015003021-appb-I000045
Figure PCTKR2015003021-appb-I000045
<화학식 b-8> <Formula b-8>
Figure PCTKR2015003021-appb-I000046
Figure PCTKR2015003021-appb-I000046
<화학식 b-9> <Formula b-9>
Figure PCTKR2015003021-appb-I000047
Figure PCTKR2015003021-appb-I000047
<화학식 b-10> <Formula b-10>
Figure PCTKR2015003021-appb-I000048
Figure PCTKR2015003021-appb-I000048
<화학식 b-11> <Formula b-11>
Figure PCTKR2015003021-appb-I000049
Figure PCTKR2015003021-appb-I000049
<화학식 b-12> <Formula b-12>
Figure PCTKR2015003021-appb-I000050
Figure PCTKR2015003021-appb-I000050
<화학식 b-13> <Formula b-13>
Figure PCTKR2015003021-appb-I000051
Figure PCTKR2015003021-appb-I000051
<화학식 b-14> <Formula b-14>
Figure PCTKR2015003021-appb-I000052
Figure PCTKR2015003021-appb-I000052
<화학식 b-15> <Formula b-15>
Figure PCTKR2015003021-appb-I000053
Figure PCTKR2015003021-appb-I000053
<화학식 b-16> <Formula b-16>
Figure PCTKR2015003021-appb-I000054
Figure PCTKR2015003021-appb-I000054
<화학식 b-17> <Formula b-17>
Figure PCTKR2015003021-appb-I000055
Figure PCTKR2015003021-appb-I000055
<화학식 b-18><Formula b-18>
Figure PCTKR2015003021-appb-I000056
.
Figure PCTKR2015003021-appb-I000056
.
나아가, 본 발명에 따른 화학식 1로 나타내는 화합물에 있어서,Furthermore, in the compound represented by the formula (1) according to the present invention,
상기 Ar1은 페난트릴기일 수 있다.Ar 1 may be a phenanthryl group.
보다 구체적으로, 상기 화학식 1로 나타내는 화합물은 하기 화학식 c-1 내지 c-36의 구조를 갖는 화합물로부터 선택될 수 있다:More specifically, the compound represented by Formula 1 may be selected from compounds having the structures of Formulas c-1 to c-36:
<화학식 c-1> <Formula c-1>
Figure PCTKR2015003021-appb-I000057
Figure PCTKR2015003021-appb-I000057
<화학식 c-2> <Formula c-2>
Figure PCTKR2015003021-appb-I000058
Figure PCTKR2015003021-appb-I000058
<화학식 c-3> <Formula c-3>
Figure PCTKR2015003021-appb-I000059
Figure PCTKR2015003021-appb-I000059
<화학식 c-4> <Formula c-4>
Figure PCTKR2015003021-appb-I000060
Figure PCTKR2015003021-appb-I000060
<화학식 c-5> <Formula c-5>
Figure PCTKR2015003021-appb-I000061
Figure PCTKR2015003021-appb-I000061
<화학식 c-6> <Formula c-6>
Figure PCTKR2015003021-appb-I000062
Figure PCTKR2015003021-appb-I000062
<화학식 c-7> <Formula c-7>
Figure PCTKR2015003021-appb-I000063
Figure PCTKR2015003021-appb-I000063
<화학식 c-8> <Formula c-8>
Figure PCTKR2015003021-appb-I000064
Figure PCTKR2015003021-appb-I000064
<화학식 c-9> <Formula c-9>
Figure PCTKR2015003021-appb-I000065
Figure PCTKR2015003021-appb-I000065
<화학식 c-10> <Formula c-10>
Figure PCTKR2015003021-appb-I000066
Figure PCTKR2015003021-appb-I000066
<화학식 c-11> <Formula c-11>
Figure PCTKR2015003021-appb-I000067
Figure PCTKR2015003021-appb-I000067
<화학식 c-12> <Formula c-12>
Figure PCTKR2015003021-appb-I000068
Figure PCTKR2015003021-appb-I000068
<화학식 c-13> <Formula c-13>
Figure PCTKR2015003021-appb-I000069
Figure PCTKR2015003021-appb-I000069
<화학식 c-14> <Formula c-14>
Figure PCTKR2015003021-appb-I000070
Figure PCTKR2015003021-appb-I000070
<화학식 c-15> <Formula c-15>
Figure PCTKR2015003021-appb-I000071
Figure PCTKR2015003021-appb-I000071
<화학식 c-16> <Formula c-16>
Figure PCTKR2015003021-appb-I000072
Figure PCTKR2015003021-appb-I000072
<화학식 c-17> <Formula c-17>
Figure PCTKR2015003021-appb-I000073
Figure PCTKR2015003021-appb-I000073
<화학식 c-18> <Formula c-18>
Figure PCTKR2015003021-appb-I000074
Figure PCTKR2015003021-appb-I000074
<화학식 c-19> <Formula c-19>
Figure PCTKR2015003021-appb-I000075
Figure PCTKR2015003021-appb-I000075
<화학식 c-20> <Formula c-20>
Figure PCTKR2015003021-appb-I000076
Figure PCTKR2015003021-appb-I000076
<화학식 c-21> <Formula c-21>
Figure PCTKR2015003021-appb-I000077
Figure PCTKR2015003021-appb-I000077
<화학식 c-22> <Formula c-22>
Figure PCTKR2015003021-appb-I000078
Figure PCTKR2015003021-appb-I000078
<화학식 c-23> <Formula c-23>
Figure PCTKR2015003021-appb-I000079
Figure PCTKR2015003021-appb-I000079
<화학식 c-24> <Formula c-24>
Figure PCTKR2015003021-appb-I000080
Figure PCTKR2015003021-appb-I000080
<화학식 c-25> <Formula c-25>
Figure PCTKR2015003021-appb-I000081
Figure PCTKR2015003021-appb-I000081
<화학식 c-26> <Formula c-26>
Figure PCTKR2015003021-appb-I000082
Figure PCTKR2015003021-appb-I000082
<화학식 c-27> <Formula c-27>
Figure PCTKR2015003021-appb-I000083
Figure PCTKR2015003021-appb-I000083
<화학식 c-28> <Formula c-28>
Figure PCTKR2015003021-appb-I000084
Figure PCTKR2015003021-appb-I000084
<화학식 c-29> <Formula c-29>
Figure PCTKR2015003021-appb-I000085
Figure PCTKR2015003021-appb-I000085
<화학식 c-30> <Formula c-30>
Figure PCTKR2015003021-appb-I000086
Figure PCTKR2015003021-appb-I000086
<화학식 c-31> <Formula c-31>
Figure PCTKR2015003021-appb-I000087
Figure PCTKR2015003021-appb-I000087
<화학식 c-32> <Formula c-32>
Figure PCTKR2015003021-appb-I000088
Figure PCTKR2015003021-appb-I000088
<화학식 c-33> <Formula c-33>
Figure PCTKR2015003021-appb-I000089
Figure PCTKR2015003021-appb-I000089
<화학식 c-34> <Formula c-34>
Figure PCTKR2015003021-appb-I000090
Figure PCTKR2015003021-appb-I000090
<화학식 c-35> <Formula c-35>
Figure PCTKR2015003021-appb-I000091
Figure PCTKR2015003021-appb-I000091
<화학식 c-36><Formula c-36>
Figure PCTKR2015003021-appb-I000092
.
Figure PCTKR2015003021-appb-I000092
.
또한, 본 발명에 따른 화학식 1로 나타내는 화합물에 있어서,In addition, in the compound represented by Formula 1 according to the present invention,
상기 Ar1은 트리메틸실릴기; 시아노기; 또는 트리플루오로메틸기로 치환된 페닐기일 수 있다.Ar 1 is trimethylsilyl group; Cyano group; Or a phenyl group substituted with a trifluoromethyl group.
보다 구체적으로, 상기 화학식 1로 나타내는 화합물은 하기 화학식 d-1 내지 d-4의 구조를 갖는 화합물로부터 선택될 수 있다:More specifically, the compound represented by Formula 1 may be selected from compounds having the structures of Formulas d-1 to d-4:
<화학식 d-1> <Formula d-1>
Figure PCTKR2015003021-appb-I000093
Figure PCTKR2015003021-appb-I000093
<화학식 d-2> <Formula d-2>
Figure PCTKR2015003021-appb-I000094
Figure PCTKR2015003021-appb-I000094
<화학식 d-3> <Formula d-3>
Figure PCTKR2015003021-appb-I000095
Figure PCTKR2015003021-appb-I000095
<화학식 d-4><Formula d-4>
Figure PCTKR2015003021-appb-I000096
.
Figure PCTKR2015003021-appb-I000096
.
또한, 본 발명은 하나의 실시예에서,In addition, the present invention in one embodiment,
제1 전극;A first electrode;
제1 전극에 대향된 제2 전극;A second electrode opposed to the first electrode;
제1 전극과 제2 전극 사이에 개재된 발광층; 및A light emitting layer interposed between the first electrode and the second electrode; And
제1 전극과 발광층 사이에 개재되는 유기층을 포함하고,An organic layer interposed between the first electrode and the light emitting layer,
상기 유기층은 제1 유기층 내지 제n 유기층으로 구성되는 n개의 유기층을 포함하며, 여기서, 제1 유기층은 발광층과 접하는 위치에 형성되고, 제1 유기층을 제외한 (n-1)개의 유기층은 제1 유기층과 제1 전극 사이에 적층되는 구조이며, n은 2 내지 5의 정수이고,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,
상기 제1 유기층은 하기 화학식 1로 나타내는 화합물을 1종 이상 포함하는 발광소자를 제공한다:The first organic layer provides a light emitting device comprising at least one compound represented by Formula 1 below:
[화학식 1][Formula 1]
Figure PCTKR2015003021-appb-I000097
Figure PCTKR2015003021-appb-I000097
상기 화학식 1에 있어서, La, Ar1, Ar2, R1, R2 및 a는 상기에서 정의한 바와 같다.In Formula 1, L a , Ar 1 , Ar 2 , R 1 , R 2 and a are as defined above.
최근 발광소자의 적용 범위가 고전류/고출력 분야로 확대되면서, 발광소자에 대한 발광효율의 증대 및 발광수명의 개선이 요구되고 있다. 이때, 상기 발광효율 및 발광수명은 발광층 내에서의 정공과 전자의 결합이 원활히 이루어져야 개선될 수 있다. 그러나, 제2 전극으로부터 주입되는 전자가 발광층을 지나 정공수송성층으로 오버플로우(overflow) 될 수 있으며, 이로 인하여 발광층에서의 정공 및 전자의 결합 효율이 감소될 수 있다. 따라서, 발광층 내의 정공과 전자의 결합이 효율적으로 이루어지기 위해서는, 제2 전극에서 주입된 전자가 발광층을 벗어나지 못하도록 차단하는 한편, 발광층에서 형성된 여기자(exciton)가 확산되거나 분리되는 것을 방지할 수 있어야 한다.Recently, 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. However, 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. .
이러한 문제를 극복하기 위하여, 본 발명에 따른 발광소자는 제1 전극과 발광층 사이에 화학식 1로 나타내는 화합물을 포함하는 유기층을 포함하는 구조를 가질 수 있다. 본 발명에 따른 상기 유기층은 제2 전극에서 주입된 전자가 발광층을 경유하여 정공수송성층으로 유입되거나, 발광층에서 형성된 여기자가 제1 전극의 방향으로 확산되어 비발광 소멸하는 것을 방지할 수 있다. 또한, 발광층에서 형성된 여기자가 발광층과 정공수송성층 사이의 계면에서 '여기자 분리(exciton dissociation)' 과정을 거쳐 비발광 소멸하는 것을 방지할 수 있다. 즉, 상기 유기층은 전자 및 여기자가 발광층을 벗어나지 못하도록 차단함으로써, 발광층 내의 전하 균형을 맞춤으로써 발광층에서의 여기자의 생성효율 및 발광소멸을 극대화할 수 있으며, 그 결과 발광소자의 발광효율이 증대되고, 구동전압이 저하되어 발광수명이 향상될 수 있다.In order to overcome this problem, the light emitting device according to the present invention may have a structure including an organic layer including a compound represented by Formula 1 between the first electrode and the light emitting layer. In 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. In addition, 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. That is, by blocking the electrons and excitons from leaving the light emitting 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.
본 발명에 따른 화학식 1로 나타내는 화합물은 카바졸의 N에 링커(La)로서 아릴렌기를 도입함과 동시에, 상기 아릴렌기에 2 이상의 고리가 융합된 다중고리 아릴기(Ar1)가 결합되거나 또는 상기 아릴렌기에 트리메틸실릴기, 시아노기, 트리플루오로메틸기 중 적어도 하나로 치환된 단일고리 아릴기(Ar1)가 결합된 구조를 가질 수 있다. 이러한 구조적 특성으로 인하여, 화학식 1로 나타내는 화합물을 포함하는 발광소자는 링커(La)가 도입되지 않거나, 단일고리 아릴기(Ar1)가 결합된 카바졸 화합물을 포함하는 발광소자와 대비하여 우수한 발광효율 및 발광수명을 가질 수 있다(실험예 1 참조).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. Due to these structural characteristics, 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).
도 1 및 도 2는 본 발명에 따른 발광소자의 개략적인 구조 단면도를 도시한 이미지이다.1 and 2 are images showing a schematic structural cross-sectional view of a light emitting device according to the present invention.
본 발명에 따른 발광소자는 제1 전극(106)과 발광층(102) 사이에 2층 이상의 다층 구조를 가지는 유기층(108)을 포함할 수 있다.The light emitting device according to the present invention 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.
구체적으로, 도 1은 2층 구조의 유기층(108, n=2인 경우)을 포함하는 발광소자의 구조를 도시한 것으로서, 상기 발광소자(100)는 베이스 기판(107) 상에 형성된 제1 전극(106), 제2 유기층(104), 제1 유기층(103), 발광층(102) 및 제2 전극(101)을 포함할 수 있다. 또한, 도 2는 3층 구조의 유기층(108, n=3인 경우)을 포함하는 발광소자의 구조를 도시한 것으로서, 상기 발광소자(100A)는 베이스 기판(107) 상에 형성된 제1 전극(106), 제3 유기층(105), 제2 유기층(104), 제1 유기층(103)을 포함할 수 있다.Specifically, FIG. 1 illustrates a structure of a light emitting device including a two-layered organic layer 108 (when n = 2), wherein the light emitting device 100 includes a first electrode formed on a base substrate 107. 106, a second organic layer 104, a first organic layer 103, a light emitting layer 102, and a second electrode 101. 2 illustrates a structure of a light emitting device including a three-layered organic layer 108 (when n = 3), wherein the light emitting device 100A includes a first electrode formed on a base substrate 107. 106, a third organic layer 105, a second organic layer 104, and a first organic layer 103.
이하, 본 발명에 따른 발광소자의 각 구성요소를 도 1 내지 도 3을 참고하여 상세히 설명한다.Hereinafter, each component of the light emitting device according to the present invention will be described in detail with reference to FIGS. 1 to 3.
먼저, 본 발명에 따른 발광소자(100 내지 100B)에 있어서, 상기 제1 전극(106)은 도전성 물질로서, 상기 베이스 기판(107) 상에 형성되어 발광소자(100 내지 100B)의 양극(anode) 역할을 수행한다.First, in the light emitting devices 100 to 100B according to the present invention, 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.
이때, 상기 제1 전극(106)은 투명 전극 또는 불투명(반사) 전극일 수 있다. 상기 제1 전극(106)이 투명 전극인 경우, 제1 전극(106)은 인듐 틴 옥사이드 (indium tin oxide, ITO), 산화주석(SnO2) 등을 포함할 수 있다. 또한, 불투명(반사) 전극인 경우, 제1 전극(106)은 ITO/은(Ag)/ITO 구조를 포함할 수 있다.In this case, the first electrode 106 may be a transparent electrode or an opaque (reflective) electrode. When the first electrode 106 is a transparent electrode, the first electrode 106 may include indium tin oxide (ITO), tin oxide (SnO 2 ), or the like. In addition, in the case of an opaque (reflective) electrode, the first electrode 106 may include an ITO / silver (Ag) / ITO structure.
다음으로, 본 발명에 따른 발광소자(100 내지 100B)에 있어서, 유기층(108)은 상기 제1 전극(106) 상에 형성되어, 제1 전극(106)과 발광층(102) 사이에 위치하게 된다.Next, in the light emitting devices 100 to 100B according to the present invention, 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. .
상기 유기층(108)은 제1 유기층 내지 제n 유기층으로 구성되는 n개의 유기층을 포함하는데, 여기서 상기 제1 유기층(103)은 발광층(102)에 접하는 위치에 형성될 수 있다. 또한, 제1 유기층(103)을 제외한 (n-1)개의 유기층은 제1 유기층(103)과 제1 전극(106) 사이에 위치하며, 제1 유기층을 기준으로 하여 제2 유기층, 제3 유기층, 제4 유기층의 순으로 적층될 수 있다.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. In addition, (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.
구체적으로 예를 들면, 도 1에 나타낸 바와 같이 n=2인 경우 제1 유기층(103)은 발광층(102)에 접하도록 위치하고, 제2 유기층(104)은 제1 유기층(103)과 제1 전극(106) 사이에 적층될 수 있다. 또한, 도 2에 나타낸 바와 같이 n=3인 경우 제1 유기층(103)은 발광층(102)에 접하도록 위치하고, 제2 유기층 및 제3 유기층(104 및 105)은 제1 유기층(103)과 제1 전극(106) 사이에 제1 유기층(103)을 기준으로 순차적으로 적층될 수 있다.Specifically, for example, as shown in FIG. 1, when n = 2, the first organic layer 103 is positioned to be in contact with the light emitting layer 102, and the second organic layer 104 is formed of the first organic layer 103 and the first electrode. Can be stacked between 106. In addition, as shown in FIG. 2, when n = 3, the first organic layer 103 is positioned to be in contact with the light emitting layer 102, and the second organic layer and the third organic layer 104 and 105 are formed of the first organic layer 103 and the first organic layer 103. The first electrodes 106 may be sequentially stacked on the basis of the first organic layer 103.
본 발명에 따른 상기 유기층(108)에 있어서, 제1 유기층(103)을 제외한 (n-1)개의 유기층은 정공수송층 및/또는 정공주입층의 역할을 수행할 수 있다. 구체적으로 예를 들면, 도 2에 나타낸 바와 같이 n=3인 경우 제2 유기층(104)은 정공수송층의 역할을 수행할 수 있다. 이때, 상기 제2 유기층(104)은 예를 들면, 4,4-비스[N-(1-나프틸)-N-페닐-아민]바이페닐(α-NPD), N,N-디페닐-N,N-비스(3-메틸페닐)-1,1-바이페닐-4,4-디아민(TPD), 폴리-(N-비닐카바졸)(PVCz) 등을 단독 또는 2종 이상 혼합하여 포함할 수 있으나, 이에 제한되는 것은 아니다. 또한, 제3 유기층(105)은 정공주입층의 역할을 수행할 수 있다. 이때, 제1 전극(106)과 제2 유기층(104)의 사이에 적층되며, 예를 들면, 구리 프탈로시아닌(copper phthalocyanine, CuPc) 등을 포함할 수 있으나, 이에 제한되는 것은 아니다.In the organic layer 108 according to the present invention, 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. Specifically, for example, as shown in FIG. 2, when n = 3, the second organic layer 104 may serve as a hole transport layer. In this case, the second organic layer 104 is, for example, 4,4-bis [N- (1-naphthyl) -N-phenyl-amine] biphenyl (α-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. In addition, the third organic layer 105 may serve as a hole injection layer. At this time, 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.
또한, 상기 (n-1)개의 유기층은 하기 화학식 3으로 나타내는 화합물을 정공수송성 화합물로서 포함할 수 있다:In addition, the (n-1) organic layers may include a compound represented by the following Chemical Formula 3 as a hole transport compound:
[화학식 3][Formula 3]
Figure PCTKR2015003021-appb-I000098
Figure PCTKR2015003021-appb-I000098
상기 화학식 3에서,In Chemical Formula 3,
R2 및 R3은 서로 독립적으로 수소, 탄소수 1 내지 6을 갖는 알킬기, 탄소수 6 내지 30을 갖는 아릴기 또는 탄소수 2 내지 20을 갖는 헤테로아릴기이고;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;
Lb는 -L1-L2-L3-L4-이며,L b is -L 1 -L 2 -L 3 -L 4- ,
L1, L2, L3 및 L4는 서로 독립적으로 단일결합, -O-, -S-, 탄소수 6 내지 30을 갖는 아릴렌기, 탄소수 2 내지 20을 갖는 헤테로아릴렌기 또는 탄소수 3 내지 20을 갖는 사이클로알킬렌기이되, L1, L2, L3 및 L4가 모두 단일결합인 경우는 제외되고;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;
Ar3 및 Ar4는 서로 독립적으로 탄소수 6 내지 30을 갖는 아릴기, 탄소수 2 내지 20을 갖는 헤테로아릴기 또는 하기 화학식 4로 나타내는 치환기이며,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),
[화학식 4][Formula 4]
Figure PCTKR2015003021-appb-I000099
Figure PCTKR2015003021-appb-I000099
상기 화학식 4에서,In Chemical Formula 4,
X는 O, S 또는 C(R6)(R7)이고,X is O, S or C (R 6 ) (R 7 ),
R4, R5, R6 및 R7은 서로 독립적으로 탄소수 1 내지 6을 갖는 알킬기, 탄소수 6 내지 30을 갖는 아릴기 또는 탄소수 2 내지 20을 갖는 헤테로아릴기이며,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,
p는 0 내지 3의 정수이고,p is an integer from 0 to 3,
q는 0 내지 4의 정수이다.q is an integer of 0-4.
구체적으로, 본 발명에 따른 상기 화학식 3으로 나타내는 정공수송성 화합물은 하기 화학식 5로 나타내는 화합물일 수 있다:Specifically, the hole transport compound represented by Chemical Formula 3 according to the present invention may be a compound represented by the following Chemical Formula 5:
[화학식 5][Formula 5]
Figure PCTKR2015003021-appb-I000100
Figure PCTKR2015003021-appb-I000100
상기 화학식 5에서,In Chemical Formula 5,
R2는 탄소수 6 내지 30을 갖는 아릴기이고;R 2 is an aryl group having 6 to 30 carbon atoms;
R3은 수소이며;R 3 is hydrogen;
Lb는 탄소수 6 내지 20을 갖는 아릴렌기이고;L b is an arylene group having 6 to 20 carbon atoms;
Ar3은 탄소수 6 내지 30을 갖는 아릴기 또는 하기 화학식 4로 나타내는 치환기이며,Ar 3 is an aryl group having 6 to 30 carbon atoms or a substituent represented by the following general formula (4),
[화학식 4][Formula 4]
Figure PCTKR2015003021-appb-I000101
Figure PCTKR2015003021-appb-I000101
상기 화학식 4에서,In Chemical Formula 4,
X는 O, S 또는 C(R6)(R7)이고,X is O, S or C (R 6 ) (R 7 ),
R4, R5, R6 및 R7은 서로 독립적으로 탄소수 1 내지 6을 갖는 알킬기 또는 탄소수 6 내지 30을 갖는 아릴기이며,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,
p는 0 내지 2의 정수이고,p is an integer from 0 to 2,
q는 0 내지 2의 정수이다.q is an integer of 0-2.
보다 구체적으로, 본 발명에 따른 화학식 5로 나타내는 화합물에 있어서,More specifically, in the compound represented by Formula 5 according to the present invention,
상기 R2는 페닐기, 바이페닐기, 터페닐기 또는 나프틸기이고;R 2 is a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group;
R3은 수소이며;R 3 is hydrogen;
Lb는 페닐렌기, 바이페닐렌기, 터페닐렌기 또는 나프틸렌기이고; 및L b is a phenylene group, a biphenylene group, a terphenylene group or a naphthylene group; And
Ar3은 페닐기, 바이페닐기, 터페닐기, 나프틸기, 디벤조티에닐기, 디벤조퓨라닐기, 플루오레닐기, 디메틸플루오레닐기 또는 디페닐플루오레닐기일 수 있다.Ar 3 may be a phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzothienyl group, dibenzofuranyl group, fluorenyl group, dimethylfluorenyl group or diphenylfluorenyl group.
나아가, 본 발명에 따른 발광소자는 화학식 1로 나타내는 화합물을 1종 이상 포함하는 제1 유기층(103);Furthermore, the light emitting device according to the present invention includes a first organic layer 103 containing at least one compound represented by Chemical Formula 1;
상기 화학식 3으로 나타내는 화합물을 포함하는 제2 유기층(104); 및A second organic layer 104 comprising a compound represented by Formula 3; And
P형 도펀트를 포함하는 제3 유기층(105)을 포함하는 구조를 가질 수 있다.It may have a structure including a third organic layer 105 including a P-type dopant.
본 발명에 따른 상기 제2 유기층(104)은 제3 유기층(105)과 함께 정공수송성 화합물로서 상기 화학식 3으로 나타내는 정공수송성 화합물을 포함할 수 있고, 제3 유기층(105)는 화학식 3으로 나타내는 정공수송성 화합물과 함께 P형 도펀트를 포함할 수 있다. 아울러, 상기 제3 유기층(105)은 정공수송성 화합물로서 상기 화학식 3으로 나타내는 정공수송성 화합물을 포함하되, 제2 유기층(104)에 포함된 화학식 3으로 나타내는 정공수송성 화합물과 그 구조가 동일하거나 또는 상이할 수 있다. 보다 구체적으로, 상기 제2 및 제3 유기층(104, 105)을 구성하는 상기 정공수송성 화합물은 상기 화학식 3으로 나타내는 정공수송성 화합물이되, R2, R3, Lb, Ar3 및 Ar4 중 어느 하나 이상은 서로 독립적으로 상이할 수 있다. 이때, 상기 제2 및 제3 유기층(104, 105) 각각을 구성하는 화합물은 정공을 상기 발광층(102)으로 효율적으로 전달하기 위한 HOMO값을 가질 수 있다.The second organic layer 104 according to the present invention 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. In addition, 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.
아울러, 상기 제3 유기층(105)을 구성하는 상기 P형 도펀트는 1종 이상의 P형 유기물 도펀트 또는 P형 무기물 도펀트를 포함할 수 있고, 1종 이상의 P형 유기물 도펀트와 1종 이상의 P형 무기물 도펀트를 동시에 포함할 수 있다.In addition, 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.
이때, 상기 P형 유기물 도펀트로는 예를 들면, 헥사데카플루오로프탈로시아닌(Hexadecafluorophthalocyanine, F16CuPc), 11,11,12,12-테트라시아노나프토-2,6-퀴노디메탄(11,11,12,12-tetracyanonaphtho-2,6-quinodimethane, TNAP), 3,6-디플루오로-2,5,7,7,8,8-헥사시아노-퀴노디메탄(3,6-difluoro-2,5,7,7,8,8-hexacyano-quinodimethane, F2-HCNQ), 테트라시아노퀴노디메탄(Tetracyanoquinodimethane, TCNQ) 등을 포함하거나, 또는 하기 화학식 6 내지 10으로 나타내는 화합물을 포함할 수 있다:In this case, as 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:
[화학식 6][Formula 6]
Figure PCTKR2015003021-appb-I000102
Figure PCTKR2015003021-appb-I000102
상기 화학식 6에서,In Chemical Formula 6,
R8은 시아노기, 설폰기, 설폭사이드기, 설폰아마이드기, 설포네이트기, 니트로기 또는 트리플루오로메틸기이고,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,
[화학식 7][Formula 7]
Figure PCTKR2015003021-appb-I000103
Figure PCTKR2015003021-appb-I000103
[화학식 8][Formula 8]
Figure PCTKR2015003021-appb-I000104
Figure PCTKR2015003021-appb-I000104
[화학식 9][Formula 9]
Figure PCTKR2015003021-appb-I000105
Figure PCTKR2015003021-appb-I000105
[화학식 10][Formula 10]
Figure PCTKR2015003021-appb-I000106
Figure PCTKR2015003021-appb-I000106
상기 화학식 10에서,In Chemical Formula 10,
m 및 n은 서로 독립적으로 1 내지 5의 정수이고;m and n are independently of each other an integer from 1 to 5;
Y1 및 Y2는 서로 독립적으로 탄소수 6 내지 30을 갖는 아릴기 또는 탄소수 2 내지 20을 갖는 헤테로아릴기이며; 및Y 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; And
상기 아릴 및 헤테로아릴기의 수소는 서로 독립적으로 비치환; 또는 탄소수 1 내지 5를 갖는 알킬기, 탄소수 1 내지 5를 갖는 알콕시기, 탄소수 1 내지 5를 갖는 할로알콕시기, 히드록시기 또는 할로겐기로 치환될 수 있다.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.
보다 구체적으로, 상기 화학식 10으로 나타내는 화합물은 하기 화학식 10a 또는 하기 화학식 10b로 나타내는 화합물을 포함할 수 있다:More specifically, the compound represented by Formula 10 may include a compound represented by Formula 10a or Formula 10b:
[화학식 10a][Formula 10a]
Figure PCTKR2015003021-appb-I000107
Figure PCTKR2015003021-appb-I000107
[화학식 10b][Formula 10b]
Figure PCTKR2015003021-appb-I000108
.
Figure PCTKR2015003021-appb-I000108
.
나아가, 상기 P형 무기물 도펀트로는 예를 들면, 금속 산화물, 금속 할라이드 등을 들 수 있다. 구체적으로는, MoO3, V2O5, WO3, SnO2, ZnO, MnO2, CoO2, ReO3, TiO2, FeCl3, SbCl5, MgF2 등을 들 수 있으며, 이들은 각각 단독으로 또는 2종 이상 혼합되어 사용될 수 있다.Furthermore, as said P-type inorganic dopant, a metal oxide, a metal halide, etc. are mentioned, for example. Specifically, MoO 3 , V 2 O 5 , WO 3 , SnO 2 , ZnO, MnO 2 , CoO 2 , ReO 3 , TiO 2, FeCl 3 , SbCl 5 , MgF 2 , and the like, each of which may be used alone. Or two or more kinds can be mixed and used.
또한, 상기 P형 도펀트의 함량은 화학식 3으로 나타내는 화합물 100 중량부에 대하여, 약 0.5 중량부 내지 약 15 중량부이거나, 약 0.5 중량부 내지 약 5 중량부일 수 있다. 또는, 화학식 3으로 나타내는 화합물 100 중량부에 대해서, 약 1 중량부 내지 10 중량부; 1 중량부 내지 5 중량부; 1.5 중량부 내지 6 중량부; 또는 2 중량부 내지 5 중량부일 수 있다.In addition, 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.
상기 P형 도펀트의 함량이 화학식 3으로 나타내는 화합물 100 중량부에 대해서, 약 0.5 중량부 내지 약 20 중량부인 경우, 상기 P형 도펀트가 화학식 3으로 나타내는 화합물의 물성을 저하시키지 않으면서도 과도한 누설 전류의 발생을 방지할 수 있다. 또한, 상기 P형 도펀트에 의해서 상기 제3 유기층(105)과 접촉하는 상, 하부층들 각각과의 계면에서의 에너지 장벽을 감소시킬 수 있다.When 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. In addition, 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.
아울러, 본 발명에 따른 발광소자(100 내지 100B)에 있어서, 상기 제1 유기층(103)은 하기 화학식 1로 나타내는 화합물을 포함할 수 있으며, 제2 유기층(104)과 발광층(102) 사이에 위치하여, 전자 차단층(electron blocking layer, EBL); 여기자 차단층; 또는 여기자 분리 차단층(exciton dissociation blocking layer, EDBL)의 역할을 수행한다:In addition, in the light emitting devices 100 to 100B according to the present invention, 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. An electron blocking layer (EBL); Exciton blocking layer; Or serves as an exciton dissociation blocking layer (EDBL):
[화학식 1][Formula 1]
Figure PCTKR2015003021-appb-I000109
Figure PCTKR2015003021-appb-I000109
상기 화학식 1에 있어서, La, Ar1, Ar2, R1 및 a는 상기에서 정의한 바와 같다.In Formula 1, L a , Ar 1 , Ar 2 , R 1 and a are as defined above.
구체적으로 하나의 실시예에서, 본 발명에 따른 상기 화학식 1로 나타내는 화합물을 제1 유기층(103)에 포함하는 발광소자(100 내지 100B)에 대한 발광효율 및 발광수명을 평가하였다.Specifically, in one embodiment, 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.
그 결과, 본 발명에 따른 화학식 1로 나타내는 화합물을 단층 구조의 제1 유기층(103)에 포함하는 발광소자(100)의 경우, 발광효율이 6.7 내지 8.6 lm/W이고, 발광수명은 214 내지 297시간인 것으로 나타났다. 또한, 2개 층 모두 화학식 1의 화합물을 포함하는 2층 구조의 제1 유기층(103)이 형성된 발광소자(100B)의 경우에는 발광효율이 6.4 내지 8.3 lm/W이고, 발광수명은 211 내지 279시간인 것으로 나타났다.As a result, 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. In addition, in the case of the light emitting device 100B in which the two layers of the first organic layer 103 including the compound of Formula 1 are formed, 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.
반면, Ar1이 페닐기인 화학식 18으로 나타내는 화합물을 제1 유기층(103)에 포함하는 발광소자 및 카바졸의 N에 링커(La)없이 Ar1이 직접 연결된 구조를 갖는 화학식 19로 나타내는 화합물을 제1 유기층(103)에 포함하는 발광소자의 경우, 본 발명에 따른 발광소자와 대비하여 발광효율 및 발광수명을 향상시키는 효과가 크지 않은 것으로 확인되었다.On the other hand, 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) In the case of the light emitting device included in the first organic layer 103, it was confirmed that the effect of improving the light emitting efficiency and the light emitting lifetime is not large as compared with the light emitting device according to the present invention.
이로부터, 본 발명에 따른 발광소자(100 내지 100B)는 카바졸의 N에 링커(La)로서 아릴렌기를 도입함과 동시에, 아릴렌기에 2 이상의 고리가 융합된 다중고리 아릴기(Ar1)가 결합되거나 또는 상기 아릴렌기에 트리메틸실릴기, 시아노기, 트리플루오로메틸기 중 적어도 하나로 치환된 단일고리 아릴기(Ar1)가 결합된 화학식 1로 나타내는 화합물을 이용하여 제1 유기층(103)을 형성함으로써 발광효율 및 발광수명이 향상됨을 알 수 있다(실험예 1 참조).From this, the light emitting devices 100 to 100B according to the present invention 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. ) Is bonded to the first organic layer (103) using a compound represented by formula ( 1 ) in which a single ring aryl group (Ar 1 ) bonded to or substituted with at least one of a trimethylsilyl group, a cyano group, and a trifluoromethyl group It can be seen that the light emission efficiency and the light emission life are improved by forming a (see Experimental Example 1).
본 발명에 따른 상기 제1 유기층(103)은 도 1 및 도 2에 나타낸 바와 같이, 화학식 1로 나타내는 화합물을 1종 이상 포함하는 단층 구조이거나, 도 3에 나타낸 바와 같이, 상층(103a) 및 하층(103b)을 포함하는 2층 구조일 수 있다.As shown in FIG. 1 and FIG. 2, the first organic layer 103 according to the present invention 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).
보다 구체적으로 예를 들면, 도 3에 나타낸 바와 같이, 상기 발광소자(100B)는 베이스 기판(107) 상에 형성된 제1 전극(106), 제3 유기층(105), 제2 유기층(104)과 함께 2층 구조의 제1 유기층(103a 및 103b)을 포함할 수 있다.More specifically, for example, as shown in FIG. 3, 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. Together, the first organic layer 103a and 103b may have a two-layer structure.
상기 제1 유기층(103)이 2층 구조일 경우, 2층 구조를 구성하는 제1 유기층의 상층(103a) 및 하층(103b) 모두 화학식 1로 나타내는 화합물을 1종 이상 포함할 수 있으며, 이때, 각 개별층에 포함되는 화학식 1로 나타내는 화합물은 서로 다른 구조를 가질 수 있다. 또한, 상기 제1 유기층(103)은 2층 구조를 구성하는 상층(103a) 및 하층(103b) 중 어느 한 층은 화학식 1로 나타내는 화합물을 1종 이상 포함하고, 다른 한 층은 하기 화학식 2로 나타내는 화합물을 포함하는 구조를 가질 수 있다:When the first organic layer 103 has 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. In addition, 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:
[화학식 2][Formula 2]
Figure PCTKR2015003021-appb-I000110
Figure PCTKR2015003021-appb-I000110
상기 화학식 2에서,In Chemical Formula 2,
Ra, Rb, Rc 및 Rd는 서로 독립적으로, 수소, 탄소수 1 내지 4를 갖는 알킬기 또는 탄소수 6 내지 14를 갖는 아릴기이다.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.
또한, 본 발명에 따른 상기 제1 유기층(103)은 발광소자(100 내지 100B)의 공진 길이에 따라 두께를 조절함으로써 발광효율을 증가시킬 수 있고, 여기자가 발광층(102)과 다른 층 사이의 계면이 아닌, 상기 발광층(102)의 중앙부에서 형성될 수 있도록 조절 가능하므로, 특별히 제한되지는 않는다.In addition, 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 In addition, since it is adjustable to be formed in the center portion of the light emitting layer 102, it is not particularly limited.
구체적으로, 상기 제1 유기층(103)dml 구조가 단층인 경우, 20 Å 내지 400 Å 범위의 두께를 가질 수 있으며, 2층 구조인 경우에는 각 개별층이 10 Å 내지 200 Å 범위의 두께를 가질 수 있다.Specifically, when the first organic layer 103 dml structure 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.
다음으로, 본 발명에 따른 발광소자(100 내지 100B)에 있어서, 상기 발광층(102)은 제1 유기층(103)과 제2 전극(101) 사이에 위치하며, 상기 발광층(102)이 방출하는 광의 파장은 발광층(102)을 형성하는 화합물의 종류에 따라 상이할 수 있다. 이때, 상기 발광층(102)을 형성하는 화합물로는 당업계에서 일반적으로 사용되는 것이라면 특별히 제한되지 않으며, 이를 상업적으로 입수하거나 또는 제조하여 사용할 수 있다.Next, in the light emitting devices 100 to 100B according to the present invention, 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. In this case, 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.
본 발명에 따른 상기 발광층(102)에서는 상기 제1 전극(106) 및 제2 전극(101) 사이에 전류를 흘려주는 경우, 제1 전극(106)으로부터 주입된 정공(hole)과 제2 전극(101)으로부터 주입된 전자(electron)가 결합하여 여기자(exciton)를 형성한다. 이때, 상기 여기자는 일중항(singlet) 여기자일 수 있으며, 또한 삼중항(triplet) 여기자일 수 있다. 이후, 상기 여기자가 기저 상태로 전이되는 과정에서, 특정 영역대의 파장을 갖는 광이 생성된다. 이에 따라, 상기 발광소자(100 내지 100B)가 외부로 광을 제공할 수 있다.In the light emitting layer 102 according to the present invention, 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.
다음으로, 본 발명에 따른 발광소자(100 내지 100B)에 있어서, 상기 제2 전극(101)은 전도성 물질로서, 상기 발광층(102) 상에 위치하여 발광소자(100 내지 100B)의 음극(cathode) 역할을 수행한다.Next, in the light emitting devices 100 to 100B according to the present invention, 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.
이때, 상기 제2 전극(101)은 니켈, 마그네슘, 칼슘, 은, 알루미늄, 인듐 등의 금속 또는 이들 중 2 이상의 금속을 포함하는 합금을 포함할 수 있으며, 보다 구체적으로는 알루미늄을 포함할 수 있다. 또한, 상기 제2 전극(101)은 상기 금속이 단층 구조 또는 2층 이상의 다층 구조를 포함할 수 있다. 아울러, 상기 제1 전극(106)이 불투명 전극인 경우, 제2 전극(101)은 투명 또는 반투명 전극일 수 있으며, 이때, 제2 전극(101)은 마그네슘 및 은을 포함하는 합금을 사용할 수 있으며, 100Å 내지 150Å의 두께를 가질 수 있다.In this case, 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. . In addition, the second electrode 101 may include a single layer structure or a multilayer structure of two or more layers. In addition, when 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 μs to 150 μm in thickness.
한편, 본 발명에 따른 발광소자(100 내지 100B)는 발광층(102)과 제2 전극(101) 사이에 전자수송성층으로서, 전자수송층(electron transporting layer, ETL) 및/또는 전자주입층(electron injecting layer, EIL)(미도시)을 더 포함할 수 있다. 이때, 상기 전자수송층 또는 상기 전자주입층을 형성하는 물질로는 당업계에서 일반적으로 사용되는 것이라면 특별히 제한되지 않으며, 이를 상업적으로 입수하거나 또는 제조하여 사용할 수 있다.On the other hand, the light emitting device 100 to 100B according to the present invention 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. In this case, 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.
또한, 본 발명에 따른 발광소자(100 내지 100B)에 있어서, 상기 발광소자(100 내지 100B)는 발광층(102)과 제2 전극(101) 사이에 위치하는 유기성층(미도시)을 더 포함할 수 있다.In addition, in the light emitting devices 100 to 100B according to the present invention, 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.
상기 유기성층은 발광층(102)과 제2 전극(101), 구체적으로는 발광층(102)과 전자수송층 사이에 위치하여, 정공이 제1 전극(106)에서부터 발광층(102)을 경유하여 전자수송층으로 유입되는 것을 방지하는 정공 차단층(hole blocking layer, HBL)의 역할을 수행할 수 있다. 또한, 상기 유기성층은 상기 발광층(102)에서 형성된 여기자가 제2 전극(101)의 방향으로 확산되어 상기 여기자가 비발광 소멸하는 것을 방지하는 여기자 차단층(exciton blocking layer)의 역할을 수행할 수 있다.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.
이때, 상기 유기성층은 발광소자(100 내지 100B)의 공진 길이에 따라 두께를 조절함으로써 발광효율을 증가시킬 수 있고, 여기자가 발광층(102)과 다른 층 사이의 계면이 아닌, 상기 발광층(102)의 중앙부에서 형성되도록 할 수 있다.At this time, 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.
아울러, 본 발명에 따른 발광소자(100 내지 100B)는 상기에서 설명한 제1 전극(106), 유기층(108), 발광층(102), 제2 전극(101) 등을 통상적인 증착 방법을 이용하여 제조할 수 있으나, 증착 방법 외에 당업계에서 통상적으로 사용하는 방법이라면 제한되지 않고 적용할 수 있다.In addition, 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. However, in addition to the deposition method, any method commonly used in the art may be applied without limitation.
나아가, 본 발명은 하나의 실시예에서, 상기에서 설명된 발광소자를 포함하는 전자장치를 제공한다. 이때, 본 발명에 따른 상기 전자장치는 디스플레이 장치 또는 조명 장치일 수 있으나, 이에 제한되는 것은 아니다.Furthermore, in one embodiment, the present invention provides an electronic device including the light emitting device described above. In this case, the electronic device according to the present invention may be a display device or a lighting device, but is not limited thereto.
본 발명에 따른 전자장치는 제1 전극과 발광층 사이에 화학식 1로 나타내는 화합물을 포함하는 유기층을 도입함으로써, 발광효율이 증대되고, 발광수명이 향상된 발광소자를 포함하므로, 고휘도/고신뢰성이 요구되는 고전류/고출력 분야에서도 사용할 수 있다.The electronic device according to the present invention 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.
이하, 본 발명을 실시예 및 실험예에 의해 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail with reference to Examples and Experimental Examples.
단, 하기 실시예 및 실험예는 본 발명을 예시하는 것일 뿐, 본 발명의 내용이 하기 실시예 및 실험예에 한정되는 것은 아니다.However, the following Examples and Experimental Examples are only illustrative of the present invention, and the content of the present invention is not limited to the following Examples and Experimental Examples.
실시예 1.Example 1.
Figure PCTKR2015003021-appb-I000111
Figure PCTKR2015003021-appb-I000111
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 150 mL)을 주입하였다. 상기 플라스크에 화학식 A(15.0 g, 26.0 mmol) 및 화학식 B(11.3 g, 57.2 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(22.0 g, 208 mmol)을 증류수(100 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(2.4 g, 2.08 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 20시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 50 mL)에 용해시키고, 메탄올(300 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 20분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1a, 16.9 g, 90%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen, followed by injection of tetrahydrofuran (THF, 150 mL). To the flask was dissolved Formula A (15.0 g, 26.0 mmol) and Formula B (11.3 g, 57.2 mmol) and stirred for 30 minutes. Sodium carbonate (22.0 g, 208 mmol) was then dissolved in distilled water (100 mL) and added to the mixture and tetrakis (triphenylphosphine) palladium (2.4 g, 2.08 mmol) was added. Thereafter, the light was blocked, refluxed for 20 hours, and then the reaction mixture was cooled to room temperature. 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.
MALDI-TOF : m/z = 723.2805 (C56H37N = 723.3).MALDI-TOF: m / z = 723.2805 (C 56 H 37 N = 723.3).
실시예 2.Example 2.
Figure PCTKR2015003021-appb-I000112
Figure PCTKR2015003021-appb-I000112
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 160 mL)을 주입하였다. 상기 플라스크에 화학식 C(16.0 g, 27.7 mmol) 및 화학식 D(18.2 g, 61.0 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(23.5 g, 221.6 mmol)을 증류수(110 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(2.6 g, 2.22 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 24시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 60 mL)에 용해시키고, 메탄올(320 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 20분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1b, 23.8g, 93%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen and then tetrahydrofuran (THF, 160 mL) was injected. To the flask was dissolved Formula C (16.0 g, 27.7 mmol) and Formula D (18.2 g, 61.0 mmol) and stirred for 30 minutes. Sodium carbonate (23.5 g, 221.6 mmol) was then dissolved in distilled water (110 mL) and added to the mixture, followed by tetrakis (triphenylphosphine) palladium (2.6 g, 2.22 mmol). Thereafter, the light was blocked, refluxed for 24 hours, and then the reaction mixture was cooled to room temperature. 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.
MALDI-TOF : m/z = 923.3862 (C72H45N = 923.4).MALDI-TOF: m / z = 923.3862 (C 72 H 45 N = 923.4).
실시예 3.Example 3.
Figure PCTKR2015003021-appb-I000113
Figure PCTKR2015003021-appb-I000113
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 155 mL)을 주입하였다. 상기 플라스크에 화학식 C(15.5 g, 26.8 mmol) 및 화학식 E(16.2 g, 59.0 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(22.7 g, 214 mmol)을 증류수(106 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(2.6 g, 2.22 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 24시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 55 mL)에 용해시키고, 메탄올(310 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 20분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1c, 21.4 g, 91%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen and then tetrahydrofuran (THF, 155 mL) was injected. To the flask was dissolved Formula C (15.5 g, 26.8 mmol) and Formula E (16.2 g, 59.0 mmol) and stirred for 30 minutes. Sodium carbonate (22.7 g, 214 mmol) was then dissolved in distilled water (106 mL) and added to the mixture, followed by tetrakis (triphenylphosphine) palladium (2.6 g, 2.22 mmol). Thereafter, the light was blocked, refluxed for 24 hours, and then the reaction mixture was cooled to room temperature. 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.
MALDI-TOF : m/z = 875.3822 (C68H45N = 875.4).MALDI-TOF: m / z = 875.3822 (C 68 H 45 N = 875.4).
실시예 4.Example 4.
Figure PCTKR2015003021-appb-I000114
Figure PCTKR2015003021-appb-I000114
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 150 mL)을 주입하였다. 상기 플라스크에 화학식 C(15.0 g, 26.0 mmol) 및 화학식 B(11.3 g, 57.2 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(22.0 g, 208 mmol)을 증류수(100 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(2.4 g, 2.08 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 24시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 50 mL)에 용해시키고, 메탄올(300 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 20분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1d, 17.7 g, 94%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen, followed by injection of tetrahydrofuran (THF, 150 mL). To the flask was dissolved Formula C (15.0 g, 26.0 mmol) and Formula B (11.3 g, 57.2 mmol) and stirred for 30 minutes. Sodium carbonate (22.0 g, 208 mmol) was then dissolved in distilled water (100 mL) and added to the mixture and tetrakis (triphenylphosphine) palladium (2.4 g, 2.08 mmol) was added. Thereafter, the light was blocked, refluxed for 24 hours, and then the reaction mixture was cooled to room temperature. 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.
MALDI-TOF : m/z = 723.2809 (C56H37N = 723.3).MALDI-TOF: m / z = 723.2809 (C 56 H 37 N = 723.3).
실시예 5.Example 5.
Figure PCTKR2015003021-appb-I000115
Figure PCTKR2015003021-appb-I000115
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 150 mL)을 주입하였다. 상기 플라스크에 화학식 F(16.0 g, 30.3 mmol) 및 화학식 B(13.2 g, 66.7 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(25.7 g, 242.4 mmol)을 증류수(100 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(2.8 g, 2.42 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 24시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 50 mL)에 용해시키고, 메탄올(300 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 20분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1e, 18.8 g, 92%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen, followed by injection of tetrahydrofuran (THF, 150 mL). In the flask, Formula F (16.0 g, 30.3 mmol) and Formula B (13.2 g, 66.7 mmol) were dissolved and stirred for 30 minutes. Sodium carbonate (25.7 g, 242.4 mmol) was then dissolved in distilled water (100 mL) and added to the mixture and tetrakis (triphenylphosphine) palladium (2.8 g, 2.42 mmol) was added. Thereafter, the light was blocked, refluxed for 24 hours, and then the reaction mixture was cooled to room temperature. 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.
MALDI-TOF : m/z = 673.2865 (C52H35N = 673.3).MALDI-TOF: m / z = 673.2865 (C 52 H 35 N = 673.3).
실시예 6.Example 6.
Figure PCTKR2015003021-appb-I000116
Figure PCTKR2015003021-appb-I000116
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 150 mL)을 주입하였다. 상기 플라스크에 화학식 C(15.0 g, 26.0 mmol) 및 화학식 G(15.7 g, 57.2 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(22.0 g, 208 mmol)을 증류수(100 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(2.4 g, 2.08 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 24시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 50 mL)에 용해시키고, 메탄올(300 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 20분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1f, 20.5 g, 90%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen, followed by injection of tetrahydrofuran (THF, 150 mL). To the flask was dissolved Formula C (15.0 g, 26.0 mmol) and Formula G (15.7 g, 57.2 mmol) and stirred for 30 minutes. Sodium carbonate (22.0 g, 208 mmol) was then dissolved in distilled water (100 mL) and added to the mixture and tetrakis (triphenylphosphine) palladium (2.4 g, 2.08 mmol) was added. Thereafter, the light was blocked, refluxed for 24 hours, and then the reaction mixture was cooled to room temperature. 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.
MALDI-TOF : m/z = 875.3737 (C68H45N = 875.4).MALDI-TOF: m / z = 875.3737 (C 68 H 45 N = 875.4).
실시예 7.Example 7.
Figure PCTKR2015003021-appb-I000117
Figure PCTKR2015003021-appb-I000117
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 150 mL)을 주입하였다. 상기 플라스크에 화학식 H(15.0 g, 27.3 mmol) 및 화학식 B(11.9 g, 60.1 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(23.2 g, 218 mmol)을 증류수(100 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(2.5 g, 2.18 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 20시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 50 mL)에 용해시키고, 메탄올(300 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 20분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1g, 16.7 g, 92%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen, followed by injection of tetrahydrofuran (THF, 150 mL). In the flask, Formula H (15.0 g, 27.3 mmol) and Formula B (11.9 g, 60.1 mmol) were dissolved and stirred for 30 minutes. Sodium carbonate (23.2 g, 218 mmol) was then dissolved in distilled water (100 mL) and added to the mixture and tetrakis (triphenylphosphine) palladium (2.5 g, 2.18 mmol) was added. Thereafter, the light was blocked, refluxed for 20 hours, and then the reaction mixture was cooled to room temperature. 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.
MALDI-TOF : m/z = 695.3112(C51H41NSi = 695.3).MALDI-TOF: m / z = 695.3112 (C 51 H 41 NSi = 695.3).
실시예 8.Example 8.
Figure PCTKR2015003021-appb-I000118
Figure PCTKR2015003021-appb-I000118
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 150 mL)을 주입하였다. 상기 플라스크에 화학식 I(16.0 g, 31.9 mmol) 및 화학식 B(13.9 g, 70.1 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(22.0 g, 208 mmol)을 증류수(100 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(3.0 g, 2.55 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 30시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 50 mL)에 용해시키고, 메탄올(300 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 20분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1h, 18.3 g, 89%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen, followed by injection of tetrahydrofuran (THF, 150 mL). To the flask was dissolved Formula I (16.0 g, 31.9 mmol) and Formula B (13.9 g, 70.1 mmol) and stirred for 30 minutes. Sodium carbonate (22.0 g, 208 mmol) was then dissolved in distilled water (100 mL) and added to the mixture and tetrakis (triphenylphosphine) palladium (3.0 g, 2.55 mmol) was added. Thereafter, the light was blocked, refluxed for 30 hours, and then the reaction mixture was cooled to room temperature. 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.
MALDI-TOF : m/z = 648.22654 (C49H32N2 = 648.3).MALDI-TOF: m / z = 648.22654 (C 49 H 32 N 2 = 648.3).
실시예 9.Example 9.
Figure PCTKR2015003021-appb-I000119
Figure PCTKR2015003021-appb-I000119
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 150 mL)을 주입하였다. 상기 플라스크에 화학식 J(15.0 g, 27.5 mmol) 및 화학식 B(12.0 g, 60.5 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(23.3 g, 220 mmol)을 증류수(100 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(2.5 g, 2.20 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 24시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 50 mL)에 용해시키고, 메탄올(300 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 20분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1i, 16.3 g, 86%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen, followed by injection of tetrahydrofuran (THF, 150 mL). In the flask, Formula J (15.0 g, 27.5 mmol) and Formula B (12.0 g, 60.5 mmol) were dissolved and stirred for 30 minutes. Sodium carbonate (23.3 g, 220 mmol) was then dissolved in distilled water (100 mL) and added to the mixture and tetrakis (triphenylphosphine) palladium (2.5 g, 2.20 mmol) was added. Thereafter, the light was blocked, refluxed for 24 hours, and then the reaction mixture was cooled to room temperature. 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.
MALDI-TOF : m/z = 691.2498 (C49H32F3N = 691.3).MALDI-TOF: m / z = 691.2498 (C 49 H 32 F 3 N = 691.3).
실시예 10.Example 10.
Figure PCTKR2015003021-appb-I000120
Figure PCTKR2015003021-appb-I000120
500 mL의 3구 둥근 바닥 플라스크에 질소를 충전한 후, 테트라히드로퓨란(THF, 150 mL)을 주입하였다. 상기 플라스크에 화학식 K(17.0 g, 31.2 mmol) 및 화학식 B(13.6 g, 68.6 mmol)를 용해시키고, 30분 동안 교반하였다. 그 후, 탄산나트륨(26.4 g, 250 mmol)을 증류수(100 mL)에 용해시켜 상기 혼합물에 첨가하고, 테트라키스(트리페닐포스핀)팔라듐(2.9 g, 2.50 mmol)을 첨가하였다. 그 후, 빛을 차단하고, 224시간 동안 환류한 다음, 반응 혼합물을 상온으로 냉각시켰다. 냉각된 반응 혼합물을 테트라히드로퓨란(THF, 50 mL)에 용해시키고, 메탄올(300 mL)이 담긴 1L 반응 용기에 첨가하였다. 그 후, 20분 동안 교반하고, 생성된 침전물을 여과 및 수집하여 연회색 고체의 목적화합물(화학식 1j, 18.7 g, 87%)을 얻었다.500 mL three-necked round bottom flask was charged with nitrogen, followed by injection of tetrahydrofuran (THF, 150 mL). In the flask, Formula K (17.0 g, 31.2 mmol) and Formula B (13.6 g, 68.6 mmol) were dissolved and stirred for 30 minutes. Sodium carbonate (26.4 g, 250 mmol) was then dissolved in distilled water (100 mL) and added to the mixture and tetrakis (triphenylphosphine) palladium (2.9 g, 2.50 mmol) was added. Thereafter, the light was blocked, refluxed for 224 hours, and then the reaction mixture was cooled to room temperature. 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.
MALDI-TOF : m/z = 691.2498 (C49H32F3N = 691.3).MALDI-TOF: m / z = 691.2498 (C 49 H 32 F 3 N = 691.3).
실시예 11 - 20. 단층 구조의 제1 유기층을 포함하는 발광소자의 제조Example 11-20. Fabrication of Light-Emitting Element comprising First Organic Layer of Single Layer Structure
인듐 틴 옥사이드(indium tin oxide, ITO)로 형성된 제1 전극 상에, 호스트 물질로서 하기 화학식 11로 나타내는 화합물을 1 Å/sec의 속도로 증착하고 동시에 하기 화학식 12로 나타내는 P형 도펀트(HAT-CN)를 상기 호스트 물질 100 중량부에 대해 3 중량부의 비율로 공증착(Co-evaporation)하여 100 Å 두께의 제3 유기층을 형성하였다. 상기 제3 유기층 상에 화학식 11로 나타내는 화합물을 300 Å의 두께로 증착하여 제2 유기층을 형성하였다.On the first electrode formed of indium tin oxide (ITO), a compound represented by the following formula (11) as a host material was deposited at a rate of 1 Å / 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.
상기 제2 유기층 상에 하기 표 1에 나타낸 바와 같이, 실시예 1 - 10에서 제조된 화합물을 100 Å의 두께로 각각 증착하여 제1 유기층을 형성하였다.As shown in Table 1 below, on the 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.
상기 제1 유기층 상에 하기 화학식 13으로 나타내는 화합물과 화학식 14로 나타내는 화합물을 100:5 중량비로 공증착하여 200 Å 두께의 발광층을 형성하였다.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.
그런 다음, 상기 발광층 상에 하기 화학식 15로 나타내는 화합물과 하기 화학식 16으로 나타내는 화합물을 50:50 중량비로 공증착하여 360 Å 두께의 전자수송층을 형성하였다. 이어서, 상기 전자수송층 상에 하기 화학식 16으로 나타내는 화합물을 이용하여 5 Å 두께의 전자주입층을 형성하였다.Thereafter, the compound represented by the following Formula 15 and the compound represented by the following Formula 16 were co-deposited at a 50:50 weight ratio to form an electron transport layer having a thickness of 360 360 on the light emitting layer. Subsequently, an electron injection layer having a thickness of 5 Å was formed on the electron transport layer by using the compound represented by the following formula (16).
마지막으로, 상기 전자주입층 상에 1,000 Å 두께의 알루미늄 박막으로 제2 전극을 형성하여 단층 구조의 제1 유기층을 포함하는 발광소자를 제조하였다.Finally, a second electrode was formed of an aluminum thin film having a thickness of 1,000 Å on the electron injection layer to manufacture a light emitting device including the first organic layer having a single layer structure.
표 1
단층 구조의 제1 유기층
실시예 11 실시예 1에서 제조된 화학식 1a의 화합물
실시예 12 실시예 2에서 제조된 화학식 1b의 화합물
실시예 13 실시예 3에서 제조된 화학식 1c의 화합물
실시예 14 실시예 4에서 제조된 화학식 1d의 화합물
실시예 15 실시예 5에서 제조된 화학식 1e의 화합물
실시예 16 실시예 6에서 제조된 화학식 1f의 화합물
실시예 17 실시예 7에서 제조된 화학식 1g의 화합물
실시예 18 실시예 8에서 제조된 화학식 1h의 화합물
실시예 19 실시예 9에서 제조된 화학식 1i의 화합물
실시예 20 실시예 10에서 제조된 화학식 1j의 화합물
Table 1
First organic layer of monolayer 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
[화학식 11][Formula 11]
Figure PCTKR2015003021-appb-I000121
Figure PCTKR2015003021-appb-I000121
[화학식 12][Formula 12]
Figure PCTKR2015003021-appb-I000122
Figure PCTKR2015003021-appb-I000122
[화학식 13][Formula 13]
Figure PCTKR2015003021-appb-I000123
Figure PCTKR2015003021-appb-I000123
[화학식 14][Formula 14]
Figure PCTKR2015003021-appb-I000124
Figure PCTKR2015003021-appb-I000124
[화학식 15][Formula 15]
Figure PCTKR2015003021-appb-I000125
Figure PCTKR2015003021-appb-I000125
[화학식 16][Formula 16]
Figure PCTKR2015003021-appb-I000126
Figure PCTKR2015003021-appb-I000126
실시예 21 - 30 (2층 구조 case 1). 2층 구조의 제1 유기층을 포함하는 발광소자의 제조 Examples 21-30 (two-layer structure case 1). Fabrication of a light emitting device comprising a first organic layer of a two-layer structure
인듐 틴 옥사이드(indium tin oxide, ITO)로 형성된 제1 전극 상에, 호스트 물질로서 상기 화학식 11로 나타내는 화합물을 1 Å/sec의 속도로 증착하고 동시에 상기 화학식 12로 나타내는 P형 도펀트(HAT-CN)를 상기 호스트 물질 100 중량부에 대해 3 중량부의 비율로 공증착(Co-evaporation)하여 100 Å 두께의 제3 유기층을 형성하였다. 상기 제3 유기층 상에 화학식 11로 나타내는 화합물을 300 Å의 두께로 증착하여 제2 유기층을 형성하였다.On the first electrode formed of indium tin oxide (ITO), a compound represented by the above formula (11) is deposited as a host material at a rate of 1 동시에 / 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.
상기 제2 유기층 상에 하기 표 2에 나타낸 바와 같이, 하기 화학식 17로 나타내는 화합물을 증착하여 제1 유기층의 하층을 형성한 다음, 상기 하층 상에 실시예 1 - 10에서 제조된 화합물(화학식 1a - 1j)을 각각 증착하여 제1 유기층의 상층을 형성하였다. 이때, 상기 상층 및 하층의 두께는 각각 50 Å이다.As shown in Table 2 below on the second organic layer, by depositing a compound represented by the following formula (17) to form a lower layer of the first organic layer, the compound prepared in Examples 1-10 on the lower layer (Formula 1a- 1j) was 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.
상기 제1 유기층의 상층 상에 상기 화학식 13으로 나타내는 화합물과 화학식 14로 나타내는 화합물을 100:5 중량비로 공증착하여 200 Å 두께의 발광층을 형성하였다.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.
그런 다음, 상기 발광층 상에 상기 화학식 15로 나타내는 화합물과 상기 화학식 16으로 나타내는 화합물을 50:50 중량비로 공증착하여 360 Å 두께의 전자수송층을 형성하였다. 이어서, 상기 전자수송층 상에 상기 화학식 16으로 나타내는 화합물을 이용하여 5 Å 두께의 전자주입층을 형성하였다.Thereafter, 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 Å. Subsequently, an electron injection layer having a thickness of 5 Å was formed on the electron transport layer by using the compound represented by Formula 16.
마지막으로, 상기 전자주입층 상에 1,000 Å 두께의 알루미늄 박막으로 제2 전극을 형성하여 2층 구조의 제1 유기층을 포함하는 발광소자를 제조하였다.Finally, a second electrode was formed of an aluminum thin film having a thickness of 1,000 Å on the electron injection layer to manufacture a light emitting device including the first organic layer having a two-layer structure.
표 2
제1 유기층
하층 상층
실시예 21 화학식 17의 화합물 실시예 1의 화합물
실시예 22 화학식 17의 화합물 실시예 2의 화합물
실시예 23 화학식 17의 화합물 실시예 3의 화합물
실시예 24 화학식 17의 화합물 실시예 4의 화합물
실시예 25 화학식 17의 화합물 실시예 5의 화합물
실시예 26 화학식 17의 화합물 실시예 6의 화합물
실시예 27 화학식 17의 화합물 실시예 7의 화합물
실시예 28 화학식 17의 화합물 실시예 8의 화합물
실시예 29 화학식 17의 화합물 실시예 9의 화합물
실시예 30 화학식 17의 화합물 실시예 10의 화합물
TABLE 2
First organic layer
substratum Upper layer
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
[화학식 17][Formula 17]
Figure PCTKR2015003021-appb-I000127
Figure PCTKR2015003021-appb-I000127
실시예 31 - 39 (2층 구조 case 2). 이층 구조의 제1 유기층을 포함하는 발광소자의 제조 Examples 31-39 (two layer structure case 2). Fabrication of light-emitting device comprising first organic layer of two-layer structure
인듐 틴 옥사이드(indium tin oxide, ITO)로 형성된 제1 전극 상에, 호스트 물질로서 상기 화학식 11로 나타내는 화합물을 1Å/sec의 속도로 증착하고 동시에 상기 화학식 12로 나타내는 P형 도펀트(HAT-CN)를 상기 호스트 물질 100 중량부에 대해 3 중량부의 비율로 공증착(Co-evaporation)하여 100 Å 두께의 제3 유기층을 형성하였다. 상기 제3 유기층 상에 화학식 11로 나타내는 화합물을 300 Å의 두께로 증착하여 제2 유기층을 형성하였다.On the first electrode formed of indium tin oxide (ITO), 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.
상기 제2 유기층 상에 하기 표 3에 나타낸 바와 같이, 실시예 7에서 제조된 화합물(화학식 1g)을 증착하여 제1 유기층의 하층을 형성한 다음, 상기 하층 상에 실시예 1 - 6 및 실시예 8 - 10에서 제조된 화합물(화학식 1a - 1f 및 화학식 1h - 1j)을 각각 증착하여 제1 유기층의 상층을 형성하였다. 이때, 상기 상층 및 하층의 두께는 각각 50 Å이다.As shown in Table 3 below, on the 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 (Formula 1a-1f and Formula 1h-1j) 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.
상기 제1 유기층의 상층 상에 상기 화학식 13으로 나타내는 화합물과 화학식 14로 나타내는 화합물을 100:5 중량비로 공증착하여 200 Å 두께의 발광층을 형성하였다.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.
그런 다음, 상기 발광층 상에 상기 화학식 15로 나타내는 화합물과 상기 화학식 16으로 나타내는 화합물을 50:50 중량비로 공증착하여 360 Å 두께의 전자수송층을 형성하였다. 이어서, 상기 전자수송층 상에 상기 화학식 16으로 나타내는 화합물을 이용하여 5 Å 두께의 전자주입층을 형성하였다.Thereafter, 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 Å. Subsequently, an electron injection layer having a thickness of 5 Å was formed on the electron transport layer by using the compound represented by Formula 16.
마지막으로, 상기 전자주입층 상에 1,000 Å 두께의 알루미늄 박막으로 제2 전극을 형성하여 2층 구조의 제1 유기층을 포함하는 발광소자를 제조하였다.Finally, a second electrode was formed of an aluminum thin film having a thickness of 1,000 Å on the electron injection layer to manufacture a light emitting device including the first organic layer having a two-layer structure.
표 3
제1 유기층
하층 상층
실시예 31 실시예 7의 화합물 실시예 1의 화합물
실시예 32 실시예 7의 화합물 실시예 2의 화합물
실시예 33 실시예 7의 화합물 실시예 3의 화합물
실시예 34 실시예 7의 화합물 실시예 4의 화합물
실시예 35 실시예 7의 화합물 실시예 5의 화합물
실시예 36 실시예 7의 화합물 실시예 6의 화합물
실시예 37 실시예 7의 화합물 실시예 8의 화합물
실시예 38 실시예 7의 화합물 실시예 9의 화합물
실시예 39 실시예 7의 화합물 실시예 10의 화합물
TABLE 3
First organic layer
substratum Upper layer
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
비교예 1. 단층 구조의 제1 유기층을 포함하는 발광소자의 제조Comparative Example 1. Fabrication of light emitting device comprising first organic layer of single layer structure
[화학식 18][Formula 18]
Figure PCTKR2015003021-appb-I000128
Figure PCTKR2015003021-appb-I000128
상기 실시예 11에서, 실시예 1에서 제조된 화합물(화학식 1a)을 사용하여 제1 유기층을 형성하는 대신에 상기 화학식 18로 나타내는 화합물을 사용하여 제1 유기층을 형성하는 것을 제외하고는 상기 실시예 11과 동일한 방법으로 수행하여 단층 구조의 제1 유기층을 포함하는 발광소자를 제조하였다.In 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.
비교예 2. 단층 구조의 제1 유기층을 포함하는 발광소자의 제조Comparative Example 2. Fabrication of Light-Emitting Device Comprising a First Organic Layer with a Single Layer Structure
[화학식 19][Formula 19]
Figure PCTKR2015003021-appb-I000129
Figure PCTKR2015003021-appb-I000129
상기 실시예 11에서, 실시예 1에서 제조된 화합물(화학식 1a)을 사용하여 제1 유기층을 형성하는 대신에 상기 화학식 19로 나타내는 화합물을 사용하여 제1 유기층을 형성하는 것을 제외하고는 상기 실시예 11과 동일한 방법으로 수행하여 단층 구조의 제1 유기층을 포함하는 발광소자를 제조하였다.In 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.
비교예 3. 2층 구조의Comparative Example 3. Two-Layer Structure 제1 유기층을 포함하는 발광소자의 제조Fabrication of a light emitting device comprising the first organic layer
[화학식 18][Formula 18]
Figure PCTKR2015003021-appb-I000130
Figure PCTKR2015003021-appb-I000130
상기 실시예 21에서, 실시예 1에서 제조된 화합물(화학식 1a)을 사용하여 제1 유기층의 상층을 형성하는 대신에 상기 화학식 18로 나타내는 화합물을 사용하여 제1 유기층의 상층을 형성하는 것을 제외하고는 상기 실시예 21과 동일한 방법으로 수행하여 2층 구조의 제1 유기층을 포함하는 발광소자를 제조하였다.In 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.
비교예 4. 2층 구조의 제1 유기층을 포함하는 발광소자의 제조Comparative Example 4. Fabrication of Light-Emitting Element comprising First Layer of Two-Layer Structure
[화학식 19][Formula 19]
Figure PCTKR2015003021-appb-I000131
Figure PCTKR2015003021-appb-I000131
상기 실시예 21에서, 실시예 1에서 제조된 화합물(화학식 1a)을 사용하여 제1 유기층의 상층을 형성하는 대신에 상기 화학식 19로 나타내는 화합물을 사용하여 제1 유기층의 상층을 형성하는 것을 제외하고는 상기 실시예 21과 동일한 방법으로 수행하여 2층 구조의 제1 유기층을 포함하는 발광소자를 제조하였다.In 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.
실험예 1. 발광소자의 발광효율 및 발광수명 평가Experimental Example 1. Evaluation of Luminous Efficiency and Luminous Life of Light Emitting Diode
본 발명에 따른 발광소자의 발광효율 및 발광수명을 평가하기 위하여 하기와 같은 실험을 수행하였다.In order to evaluate the luminous efficiency and light emitting lifetime of the light emitting device according to the present invention, the following experiment was performed.
먼저, 질소 분위기의 글로브 박스 안에서 흡습제(Getter)가 부착된 커버 글래스의 가장자리에 UV 경화용 실런트를 디스펜싱한 후, 상기 실시예 11 - 39 및 비교예 1 내지 4에서 제조된 발광소자 각각과 커버 글래스를 합착하였다. 그 후, 합착된 발광소자에 UV 광을 조사하여 경화시키고, 경화된 발광소자의 발광효율을 측정하였다. 이때, 발광효율은 휘도가 1,000 cd/m2일 때의 값을 기준으로 하여 측정하였으며, 측정값의 단위는 lm/W이다.First, after dispensing the UV curing sealant on the edge of the cover glass with a moisture absorbent (Getter) in a glove box of nitrogen atmosphere, and then each of the light emitting device and the cover manufactured in Examples 11-39 and Comparative Examples 1-4 The glass was bonded. Thereafter, the bonded light emitting device was irradiated with UV light and cured, and the luminous efficiency of the cured light emitting device was measured. In this case, 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.
다음으로, 25℃의 온도로 일정하게 유지되고 있는 측정용 오븐 내에 설치된 수명 측정기를 이용하여 상기 실시예 11 - 39 및 비교예 1 내지 4에서 제조된 발광소자의 각 발광수명을 측정하였다. 이때, T50은 발광소자의 초기 휘도가 5,000 cd/m2인 경우, 발광소자의 휘도가 초기 휘도 대비 50%가 되기까지 걸린 시간을 의미한다. 수명에 대한 값은 당업자에게 공지된 전환식을 기초로 하여 다른 측정 조건에서 측정한 경우에 예상되는 수명으로 전환될 수 있다.Next, the light emitting lifetimes of the light emitting devices manufactured in Examples 11 to 39 and Comparative Examples 1 to 4 were measured using a life meter installed in a measuring oven maintained at a constant temperature of 25 ° C. In this case, when the initial luminance of the light emitting device is 5,000 cd / m 2 , 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.
하기 표 4는 실시예 11 - 20에 따른 발광소자의 발광효율 및 발광수명을 비교예 1 및 비교예 2에 따른 발광소자와 대비한 것이다. 상기에서 설명한 바와 같이, 실시예 11 - 20은 제1 유기층을 단층으로 구성하되, 단층의 제1 유기층이 상기 화학식 1로 나타내는 본 발명의 화합물을 포함하도록 구성한 경우이다.Table 4 below compares the luminous efficiency and light emitting lifetime of the light emitting device according to Examples 11-20 with those of the light emitting device according to Comparative Example 1 and Comparative Example 2. As described above, in Examples 11 to 20, 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.
표 4
단층 구조의 제1 유기층
발광효율[lm/W] 발광수명(T50[hr])
실시예 11 8.1 287
실시예 12 7.0 228
실시예 13 7.4 242
실시예 14 8.5 284
실시예 15 8.4 271
실시예 16 7.7 266
실시예 17 8.6 297
실시예 18 6.9 214
실시예 19 6.7 225
실시예 20 8.4 275
비교예 1 5.6 182
비교예 2 5.9 179
Table 4
First organic layer of monolayer structure
Luminous Efficiency [lm / W] Light emitting life (T 50 [hr])
Example 11 8.1 287
Example 12 7.0 228
Example 13 7.4 242
Example 14 8.5 284
Example 15 8.4 271
Example 16 7.7 266
Example 17 8.6 297
Example 18 6.9 214
Example 19 6.7 225
Example 20 8.4 275
Comparative Example 1 5.6 182
Comparative Example 2 5.9 179
또한, 하기 표 5는 실시예 21 - 39에 따른 발광소자의 발광효율 및 발광수명을 나타낸 것이다. 상기에서 설명한 바와 같이, 실시예 21 - 39에 따른 발광소자는 2층 구조의 제1 유기층을 포함하는 구조를 갖는다. 이때, 실시예 21 - 30은 제1 유기층의 2개 층 중 1개의 층만이 본 발명에 따른 화학식 1의 화합물을 포함하도록 구성한 경우(2층 구조 case 1)이고, 실시예 31 - 39에 따른 발광소자는 제1 유기층의 2개 층 모두 본 발명에 따른 화학식 1의 화합물을 포함하도록 구성한 경우(2층 구조 case 2) 이다.In addition, Table 5 shows the light emission efficiency and the light emitting life of the light emitting device according to Examples 21-39. As described above, the light emitting device according to Examples 21 to 39 has a structure including a first organic layer having a two-layer structure. At this time, 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).
표 5
2층 구조의 제1 유기층(2층 구조 case 1) 2층 구조의 제1 유기층(2층 구조 case 2)
발광효율[lm/W] 발광수명(T50[hr]) 발광효율[lm/W] 발광수명(T50[hr])
실시예 21 7.5 267 실시예 31 7.9 279
실시예 22 6.4 210 실시예 32 6.8 224
실시예 23 6.9 221 실시예 33 7.2 238
실시예 24 8.1 272 실시예 34 8.1 275
실시예 25 8.0 258 실시예 35 8.3 270
실시예 26 7.2 236 실시예 36 7.5 251
실시예 27 8.2 283 - - -
실시예 28 6.2 207 실시예 37 6.6 211
실시예 29 6.3 205 실시예 38 6.4 216
실시예 30 7.9 269 실시예 39 8.2 273
비교예 3 5.8 198 비교예 4 6.1 189
Table 5
First organic layer of two-layer structure (two-layer structure case 1) First organic layer of two-layer structure (two-layer structure case 2)
Luminous Efficiency [lm / W] Light emitting life (T 50 [hr]) Luminous Efficiency [lm / W] Light emitting life (T 50 [hr])
Example 21 7.5 267 Example 31 7.9 279
Example 22 6.4 210 Example 32 6.8 224
Example 23 6.9 221 Example 33 7.2 238
Example 24 8.1 272 Example 34 8.1 275
Example 25 8.0 258 Example 35 8.3 270
Example 26 7.2 236 Example 36 7.5 251
Example 27 8.2 283 - - -
Example 28 6.2 207 Example 37 6.6 211
Example 29 6.3 205 Example 38 6.4 216
Example 30 7.9 269 Example 39 8.2 273
Comparative Example 3 5.8 198 Comparative Example 4 6.1 189
구체적으로, 표 4를 참조하여 단층 구조의 제1 유기층을 포함하는 발광소자를 살펴보면, 본 발명에 따른 화학식 1로 나타내는 화합물을 제1 유기층에 포함하는 발광소자는 발광효율이 6.7 내지 8.6 lm/W이고, 발광수명은 214 내지 297시간인 것으로 나타났다. 특히, 카바졸의 N에 페닐렌기를 링커(La)로 도입하고, 2 이상의 고리가 융합된 다중고리 아릴기(Ar1)를 포함하는 화학식 1d의 화합물을 포함하는 발광소자와 트리메틸실릴기로 치환된 화학식 1g의 화합물을 포함하는 발광소자의 발광효율 및 발광수명이 각각 8.5 및 8.6 lm/W와 284 및 297시간으로 현저히 우수한 값을 나타내었다.Specifically, referring to Table 4, 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. In particular, 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.
반면, Ar1이 페닐기인 화학식 18의 화합물을 제1 유기층에 포함하는 발광소자(비교예 1)의 경우, 발광효율은 5.6 lm/W이고, 발광수명은 182시간인 것으로 나타났으며, 카바졸의 N에 링커(La)없이 아릴기(Ar1)가 직접 연결된 구조를 갖는 화학식 19의 화합물을 제1 유기층에 포함하는 발광소자(비교예 2)의 경우, 발광효율 및 발광수명은 각각 5.9 lm/W, 179시간인 것으로 나타났다.On the other hand, in the case of the light emitting device (Comparative Example 1) containing the compound of Formula 18, wherein Ar 1 is a phenyl group in the first organic layer, the luminous efficiency is 5.6 lm / W, the emission lifetime is 182 hours, carbazole In the case of a light emitting device (Comparative Example 2) comprising a compound of Formula 19 having a structure in which an aryl group (Ar 1 ) is directly connected to N without a linker (L a ) in the first organic layer, the light emitting efficiency and the light emitting lifetime are respectively 5.9. lm / W, 179 hours.
즉, 본 발명에 따른 화학식 1의 화합물을 포함하는 단층 구조의 제1 유기층이 형성된 발광소자는 Ar1이 페닐기인 화학식 18의 화합물을 제1 유기층에 포함하는 발광소자와 대비하여 발광효율은 약 1.20 내지 1.54배 증대되고, 발광수명은 약 1.18 내지 1.63배 향상되는 것을 확인할 수 있다. 또한, 상기 화학식 1의 화합물 대신에, 카바졸의 N에 링커(La)없이 아릴기(Ar1)가 직접 연결된 구조를 갖는 화학식 19의 화합물을 제1 유기층에 포함하는 발광소자와 대비하여도 발광효율은 약 1.14 내지 1.46배 증대되고, 발광수명은 약 1.20 내지 1.66배 향상되는 것을 알 수 있다. That is, in 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, 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. In addition, in contrast to the compound of Formula 1, 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.
또한, 표 5를 참조하여 2층 구조의 제1 유기층을 포함하는 발광소자를 살펴보면, 2층 구조의 제1 유기층 중 1개 층이 본 발명에 따른 화학식 1의 화합물을 포함하는 발광소자(2층 구조 case 1)는 발광효율이 6.2 내지 8.2 m/W이고, 발광수명은 205 내지 283시간인 것으로 나타났다. 아울러, 2층 구조의 제1 유기층 모두 본 발명에 따른 화학식 1의 화합물을 포함하는 발광소자(2층 구조 case 2)는 발광효율이 6.4 내지 8.3 m/W이고, 발광수명은 211 내지 279시간인 것으로 나타났다.In addition, referring to Table 5, the light emitting device including the first organic layer having a two-layer structure, one layer of the first organic layer of the 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. In addition, 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.
반면, 아릴기(Ar1)가 페닐기인 화학식 18의 화합물을 제1 유기층에 포함하는 발광소자(비교예 3)의 경우, 발광효율은 5.8 lm/W이고, 발광수명은 198시간인 것으로 나타났으며, 카바졸의 N에 링커(La)없이 아릴기(Ar1)가 직접 연결된 구조를 갖는 화학식 19의 화합물을 제1 유기층에 포함하는 발광소자(비교예 4)의 경우, 발광효율 및 발광수명은 각각 6.1 lm/W, 189시간인 것으로 나타났다.On the other hand, in the case of the light emitting device (Comparative Example 3) containing the compound of Formula 18 in which the aryl group (Ar 1 ) is a phenyl group in the first organic layer, the luminous efficiency is 5.8 lm / W, the emission lifetime is 198 hours In the case of a light emitting device (Comparative Example 4) 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 The lifetimes were 6.1 lm / W and 189 hours, respectively.
즉, 본 발명에 따른 상기 '2층 구조 case 1'의 경우, 화학식 1의 화합물을 사용하는 대신에 Ar1이 페닐기인 화학식 18의 화합물을 사용한 발광소자(비교예 3)와 대비하여 발광효율은 약 1.07 내지 1.41배 증대되고, 발광수명은 약 1.04 내지 1.43배 향상되는 것을 확인할 수 있다. 또한, 화학식 1의 화합물 대신에 카바졸의 N에 링커(La)없이 아릴기(Ar1)가 직접 연결된 구조를 갖는 화학식 19의 화합물을 사용한 발광소자(비교예 4)와 대비하여도 발광효율은 약 1.02 내지 1.34배 증대되고, 발광수명은 약 1.08 내지 1.50배 향상되는 것을 알 수 있다.That is, in the case of the 'two-layer structure case 1' according to the present invention, in contrast to the light emitting device using the compound of Formula 18, wherein Ar 1 is a phenyl group (Comparative Example 3) instead of using the compound of Formula 1, It can be seen that the light emission life is increased by about 1.07 to 1.41 times and about 1.04 to 1.43 times. In addition, luminous efficiency 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 ) instead of the compound of Formula 1 It can be seen that the silver is increased by about 1.02 to 1.34 times, and the light emission life is improved by about 1.08 to 1.50 times.
아울러, 본 발명에 따른 상기 '2층 구조 case 2'의 경우에도, Ar1이 페닐기인 화학식 18로 나타내는 화합물을 사용한 발광소자(비교예 3)와 대비하여 발광효율은 약 1.10 내지 1.43배 증대되고, 발광수명은 약 1.07 내지 1.41배 향상되는 것을 확인할 수 있다. 또한, 카바졸의 N에 링커(La)없이 아릴기(Ar1)가 직접 연결된 구조를 갖는 화학식 19의 화합물을 사용한 발광소자(비교예 4)와 대비하여도 발광효율은 약 1.05 내지 1.36배 증대되고, 발광수명은 약 1.12 내지 1.48배 향상되는 것을 알 수 있다.In addition, in the case of the 'two-layer structure case 2' according to the present invention, 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.
이로부터, '2층 구조 case 1' 및 '2층 구조 case 2' 모두, Ar1이 페닐기인 화학식 18로 나타내는 화합물을 사용한 발광소자(비교예 3) 및 카바졸의 N에 링커(La)없이 아릴기(Ar1)가 직접 연결된 구조를 갖는 화학식 19의 화합물을 사용한 발광소자(비교예 4)와 대비하여 발광효율 및 발광수명이 현저히 향상되는 것을 알 수 있다. 이러한 결과는 대칭구조를 가지며, 카바졸의 N에 링커(La)로서 아릴렌기를 도입함과 동시에, 아릴렌기에 2 이상의 고리가 융합된 다중고리 아릴기(Ar1)가 결합되거나 또는 상기 아릴렌기에 트리메틸실릴기, 시아노기, 트리플루오로메틸기 중 적어도 하나로 치환된 단일고리 아릴기(Ar1)가 결합된 본 발명에 따른 화학식 1로 나타내는 화합물을 제1 전극과 발광층 사이에 도입된 유기층에 도입함으로써 유도되는 효과임을 알 수 있다.From this, 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.
한편, 상기 결과로부터 '2층 구조 case 1' 및 '2층 구조 case 2'의 발광소자보다 본 발명에 따른 화학식 1의 화합물을 포함하는 단층 구조의 제1 유기층이 형성된 발광소자가 발광효율 및 발광수명의 향상 효과가 보다 우수한 것을 알 수 있다.On the other hand, from the above results, 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.
보다 구체적으로, 제1 유기층이 단층 구조인 발광소자와 '2층 구조 case 1'의 발광소자의 발광효율 및 발광수명을 대비해보면, 단층 구조의 제1 유기층이 형성된 실시예 11 - 20의 발광소자는 동일한 화합물을 제1 유기층의 상층에 사용한 실시예 21 - 30의 발광소자와 대비하여 발광효율 및 발광수명이 우수한 것을 알 수 있다. 또한, 동일한 방식으로 '2층 구조 case 2'의 발광소자를 대비해 보면, 단층 구조의 제1 유기층이 형성된 실시예 11 - 20의 발광소자는 동일한 화합물을 제1 유기층의 상층에 포함하면서, 실시예 7의 화합물로 제1 유기층의 하층을 형성한 발광소자와 대비하여 발광효율 및 발광수명이 우수한 것을 알 수 있다.More specifically, when comparing the luminous efficiency and the light emitting life of the light emitting device having a single layer structure of the first organic layer and the light emitting device of the 'two-layer structure case 1', 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. In addition, in contrast to the light emitting device of the 'two-layer structure case 2' in the same manner, 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.
또한, 상기 '2층 구조 case 1' 및 '2층 구조 case 2'의 발광소자들을 대비해 보면, 제1 유기층의 상층 및 하층, 모두를 서로 다른 구조를 갖는 화학식 1의 화합물로 형성한 '2층 구조 case 2'의 발광소자가 발광효율 및 발광수명이 제1 유기층의 상층만을 화학식 1의 화합물로 형성한 '2층 구조 case 1'의 발광소자보다 우수한 것을 알 수 있다.In addition, in contrast to the light emitting devices of the 'two-layer structure case 1' and 'two-layer structure case 2', 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.
즉, 발광소자에 형성되는 제1 유기층을 2층 구조로 형성하는 경우, 본 발명에 따른 화학식 1의 화합물을 2층 구조의 1개 층에만 사용하는 것보다 2개 층 모두에 사용하는 것이 발광효율 및 발광수명을 향상시키는 효과가 보다 우수한 것을 알 수 있다.That is, when 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.
따라서, 본 발명에 따른 발광소자는 제1 전극과 발광층 사이에 화학식 1로 나타내는 화합물을 포함하는 유기층을 형성함으로써, 우수한 발광효율 및 발광수명을 가지므로, 고휘도/고신뢰성이 요구되는 고전류/고출력 분야의 전자 장치에 유용하게 사용될 수 있다.Accordingly, 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, 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.

Claims (22)

  1. 하기 화학식 1로 나타내는 화합물:Compound represented by the following formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2015003021-appb-I000132
    Figure PCTKR2015003021-appb-I000132
    상기 화학식 1에 있어서,In Chemical Formula 1,
    La는 탄소수 6 내지 20을 갖는 아릴렌기이고;L a is an arylene group having 6 to 20 carbon atoms;
    Ar1 및 Ar2는 서로 독립적으로 수소 또는 탄소수 6 내지 30을 갖는 아릴기이며,Ar 1 and Ar 2 are each independently hydrogen or an aryl group having 6 to 30 carbon atoms,
    상기 탄소수 6 내지 30을 갖는 아릴기에 함유된 수소 중 어느 하나 이상은, 서로 독립적으로 Si(R)3, 시아노기, 또는 탄소수 1 내지 4를 갖는 할로알킬기로 치환되거나, 비치환되고,At least one of hydrogen contained in the aryl group having 6 to 30 carbon atoms is independently substituted with each other, and is unsubstituted or substituted with a Si (R) 3 , a cyano group, or a haloalkyl group having 1 to 4 carbon atoms,
    상기 R은 탄소수 1 내지 4를 갖는 알킬기이며;R is an alkyl group having 1 to 4 carbon atoms;
    R1은 수소 또는 탄소수 6 내지 20을 갖는 아릴기이며; 및R 1 is hydrogen or an aryl group having 6 to 20 carbon atoms; And
    a는 1 또는 2이다.a is 1 or 2.
  2. 제1항에 있어서,The method of claim 1,
    화학식 1에서,In Formula 1,
    상기 La는 페닐렌기 또는 나프틸렌기이고;L a is a phenylene group or a naphthylene group;
    Ar2는 수소, 페닐기, 바이페닐기, 나프틸기 또는 페난트릴기이며;Ar 2 is hydrogen, a phenyl group, a biphenyl group, a naphthyl group or a phenanthryl group;
    R1은 수소 또는 페닐기이고; 및R 1 is hydrogen or a phenyl group; And
    a는 1 또는 2인 화합물.a is 1 or 2;
  3. 제2항에 있어서,The method of claim 2,
    화학식 1에서,In Formula 1,
    상기 Ar1은 1-나프틸기인 화합물.Ar 1 is a 1-naphthyl group.
  4. 제3항에 있어서,The method of claim 3,
    제3항에 따른 화합물은, 하기 화학식 a-1 내지 a-36의 구조로부터 선택되는 것을 특징으로 하는 화합물:A compound according to claim 3, wherein the compound is selected from the structures of formulas a-1 to a-36:
    <화학식 a-1> <Formula a-1>
    Figure PCTKR2015003021-appb-I000133
    Figure PCTKR2015003021-appb-I000133
    <화학식 a-2> <Formula a-2>
    Figure PCTKR2015003021-appb-I000134
    Figure PCTKR2015003021-appb-I000134
    <화학식 a-3> <Formula a-3>
    Figure PCTKR2015003021-appb-I000135
    Figure PCTKR2015003021-appb-I000135
    <화학식 a-4> <Formula a-4>
    Figure PCTKR2015003021-appb-I000136
    Figure PCTKR2015003021-appb-I000136
    <화학식 a-5> <Formula a-5>
    Figure PCTKR2015003021-appb-I000137
    Figure PCTKR2015003021-appb-I000137
    <화학식 a-6> <Formula a-6>
    Figure PCTKR2015003021-appb-I000138
    Figure PCTKR2015003021-appb-I000138
    <화학식 a-7> <Formula a-7>
    Figure PCTKR2015003021-appb-I000139
    Figure PCTKR2015003021-appb-I000139
    <화학식 a-8> <Formula a-8>
    Figure PCTKR2015003021-appb-I000140
    Figure PCTKR2015003021-appb-I000140
    <화학식 a-9> <Formula a-9>
    Figure PCTKR2015003021-appb-I000141
    Figure PCTKR2015003021-appb-I000141
    <화학식 a-10> <Formula a-10>
    Figure PCTKR2015003021-appb-I000142
    Figure PCTKR2015003021-appb-I000142
    <화학식 a-11> <Formula a-11>
    Figure PCTKR2015003021-appb-I000143
    Figure PCTKR2015003021-appb-I000143
    <화학식 a-12> <Formula a-12>
    Figure PCTKR2015003021-appb-I000144
    Figure PCTKR2015003021-appb-I000144
    <화학식 a-13> <Formula a-13>
    Figure PCTKR2015003021-appb-I000145
    Figure PCTKR2015003021-appb-I000145
    <화학식 a-14> <Formula a-14>
    Figure PCTKR2015003021-appb-I000146
    Figure PCTKR2015003021-appb-I000146
    <화학식 a-15> <Formula a-15>
    Figure PCTKR2015003021-appb-I000147
    Figure PCTKR2015003021-appb-I000147
    <화학식 a-16> <Formula a-16>
    Figure PCTKR2015003021-appb-I000148
    Figure PCTKR2015003021-appb-I000148
    <화학식 a-17> <Formula a-17>
    Figure PCTKR2015003021-appb-I000149
    Figure PCTKR2015003021-appb-I000149
    <화학식 a-18> <Formula a-18>
    Figure PCTKR2015003021-appb-I000150
    Figure PCTKR2015003021-appb-I000150
    <화학식 a-19> <Formula a-19>
    Figure PCTKR2015003021-appb-I000151
    Figure PCTKR2015003021-appb-I000151
    <화학식 a-20> <Formula a-20>
    Figure PCTKR2015003021-appb-I000152
    Figure PCTKR2015003021-appb-I000152
    <화학식 a-21> <Formula a-21>
    Figure PCTKR2015003021-appb-I000153
    Figure PCTKR2015003021-appb-I000153
    <화학식 a-22> <Formula a-22>
    Figure PCTKR2015003021-appb-I000154
    Figure PCTKR2015003021-appb-I000154
    <화학식 a-23> <Formula a-23>
    Figure PCTKR2015003021-appb-I000155
    Figure PCTKR2015003021-appb-I000155
    <화학식 a-24> <Formula a-24>
    Figure PCTKR2015003021-appb-I000156
    Figure PCTKR2015003021-appb-I000156
    <화학식 a-25> <Formula a-25>
    Figure PCTKR2015003021-appb-I000157
    Figure PCTKR2015003021-appb-I000157
    <화학식 a-26> <Formula a-26>
    Figure PCTKR2015003021-appb-I000158
    Figure PCTKR2015003021-appb-I000158
    <화학식 a-27> <Formula a-27>
    Figure PCTKR2015003021-appb-I000159
    Figure PCTKR2015003021-appb-I000159
    <화학식 a-28> <Formula a-28>
    Figure PCTKR2015003021-appb-I000160
    Figure PCTKR2015003021-appb-I000160
    <화학식 a-29> <Formula a-29>
    Figure PCTKR2015003021-appb-I000161
    Figure PCTKR2015003021-appb-I000161
    <화학식 a-30> <Formula a-30>
    Figure PCTKR2015003021-appb-I000162
    Figure PCTKR2015003021-appb-I000162
    <화학식 a-31> <Formula a-31>
    Figure PCTKR2015003021-appb-I000163
    Figure PCTKR2015003021-appb-I000163
    <화학식 a-32> <Formula a-32>
    Figure PCTKR2015003021-appb-I000164
    Figure PCTKR2015003021-appb-I000164
    <화학식 a-33> <Formula a-33>
    Figure PCTKR2015003021-appb-I000165
    Figure PCTKR2015003021-appb-I000165
    <화학식 a-34> <Formula a-34>
    Figure PCTKR2015003021-appb-I000166
    Figure PCTKR2015003021-appb-I000166
    <화학식 a-35> <Formula a-35>
    Figure PCTKR2015003021-appb-I000167
    Figure PCTKR2015003021-appb-I000167
    <화학식 a-36><Formula a-36>
    Figure PCTKR2015003021-appb-I000168
    .
    Figure PCTKR2015003021-appb-I000168
    .
  5. 제2항에 있어서,The method of claim 2,
    화학식 1에서,In Formula 1,
    상기 Ar1은 2-나프틸기인 화합물.Ar 1 is a 2-naphthyl group.
  6. 제5항에 있어서,The method of claim 5,
    제5항에 따른 화합물은, 하기 화학식 b-1 내지 b-18의 구조로부터 선택되는 것을 특징으로 하는 화합물:The compound according to claim 5, wherein the compound is selected from the structures of formulas b-1 to b-18:
    <화학식 b-1> <Formula b-1>
    Figure PCTKR2015003021-appb-I000169
    Figure PCTKR2015003021-appb-I000169
    <화학식 b-2> <Formula b-2>
    Figure PCTKR2015003021-appb-I000170
    Figure PCTKR2015003021-appb-I000170
    <화학식 b-3> <Formula b-3>
    Figure PCTKR2015003021-appb-I000171
    Figure PCTKR2015003021-appb-I000171
    <화학식 b-4> <Formula b-4>
    Figure PCTKR2015003021-appb-I000172
    Figure PCTKR2015003021-appb-I000172
    <화학식 b-5> <Formula b-5>
    Figure PCTKR2015003021-appb-I000173
    Figure PCTKR2015003021-appb-I000173
    <화학식 b-6> <Formula b-6>
    Figure PCTKR2015003021-appb-I000174
    Figure PCTKR2015003021-appb-I000174
    <화학식 b-7> <Formula b-7>
    Figure PCTKR2015003021-appb-I000175
    Figure PCTKR2015003021-appb-I000175
    <화학식 b-8> <Formula b-8>
    Figure PCTKR2015003021-appb-I000176
    Figure PCTKR2015003021-appb-I000176
    <화학식 b-9> <Formula b-9>
    Figure PCTKR2015003021-appb-I000177
    Figure PCTKR2015003021-appb-I000177
    <화학식 b-10> <Formula b-10>
    Figure PCTKR2015003021-appb-I000178
    Figure PCTKR2015003021-appb-I000178
    <화학식 b-11> <Formula b-11>
    Figure PCTKR2015003021-appb-I000179
    Figure PCTKR2015003021-appb-I000179
    <화학식 b-12> <Formula b-12>
    Figure PCTKR2015003021-appb-I000180
    Figure PCTKR2015003021-appb-I000180
    <화학식 b-13> <Formula b-13>
    Figure PCTKR2015003021-appb-I000181
    Figure PCTKR2015003021-appb-I000181
    <화학식 b-14> <Formula b-14>
    Figure PCTKR2015003021-appb-I000182
    Figure PCTKR2015003021-appb-I000182
    <화학식 b-15> <Formula b-15>
    Figure PCTKR2015003021-appb-I000183
    Figure PCTKR2015003021-appb-I000183
    <화학식 b-16> <Formula b-16>
    Figure PCTKR2015003021-appb-I000184
    Figure PCTKR2015003021-appb-I000184
    <화학식 b-17> <Formula b-17>
    Figure PCTKR2015003021-appb-I000185
    Figure PCTKR2015003021-appb-I000185
    <화학식 b-18><Formula b-18>
    Figure PCTKR2015003021-appb-I000186
    .
    Figure PCTKR2015003021-appb-I000186
    .
  7. 제2항에 있어서,The method of claim 2,
    화학식 1로 나타내는 화합물에서,In the compound represented by the formula (1),
    상기 Ar1은 페난트릴기인 화합물.Ar 1 is a phenanthryl group.
  8. 제7항에 있어서,The method of claim 7, wherein
    제7항에 따른 화합물은, 하기 화학식 c-1 내지 c-36의 구조로부터 선택되는 것을 특징으로 하는 화합물:The compound according to claim 7, wherein the compound is selected from the structures of formulas c-1 to c-36:
    <화학식 c-1> <Formula c-1>
    Figure PCTKR2015003021-appb-I000187
    Figure PCTKR2015003021-appb-I000187
    <화학식 c-2> <Formula c-2>
    Figure PCTKR2015003021-appb-I000188
    Figure PCTKR2015003021-appb-I000188
    <화학식 c-3> <Formula c-3>
    Figure PCTKR2015003021-appb-I000189
    Figure PCTKR2015003021-appb-I000189
    <화학식 c-4> <Formula c-4>
    Figure PCTKR2015003021-appb-I000190
    Figure PCTKR2015003021-appb-I000190
    <화학식 c-5> <Formula c-5>
    Figure PCTKR2015003021-appb-I000191
    Figure PCTKR2015003021-appb-I000191
    <화학식 c-6> <Formula c-6>
    Figure PCTKR2015003021-appb-I000192
    Figure PCTKR2015003021-appb-I000192
    <화학식 c-7> <Formula c-7>
    Figure PCTKR2015003021-appb-I000193
    Figure PCTKR2015003021-appb-I000193
    <화학식 c-8> <Formula c-8>
    Figure PCTKR2015003021-appb-I000194
    Figure PCTKR2015003021-appb-I000194
    <화학식 c-9> <Formula c-9>
    Figure PCTKR2015003021-appb-I000195
    Figure PCTKR2015003021-appb-I000195
    <화학식 c-10> <Formula c-10>
    Figure PCTKR2015003021-appb-I000196
    Figure PCTKR2015003021-appb-I000196
    <화학식 c-11> <Formula c-11>
    Figure PCTKR2015003021-appb-I000197
    Figure PCTKR2015003021-appb-I000197
    <화학식 c-12> <Formula c-12>
    Figure PCTKR2015003021-appb-I000198
    Figure PCTKR2015003021-appb-I000198
    <화학식 c-13> <Formula c-13>
    Figure PCTKR2015003021-appb-I000199
    Figure PCTKR2015003021-appb-I000199
    <화학식 c-14> <Formula c-14>
    Figure PCTKR2015003021-appb-I000200
    Figure PCTKR2015003021-appb-I000200
    <화학식 c-15> <Formula c-15>
    Figure PCTKR2015003021-appb-I000201
    Figure PCTKR2015003021-appb-I000201
    <화학식 c-16> <Formula c-16>
    Figure PCTKR2015003021-appb-I000202
    Figure PCTKR2015003021-appb-I000202
    <화학식 c-17> <Formula c-17>
    Figure PCTKR2015003021-appb-I000203
    Figure PCTKR2015003021-appb-I000203
    <화학식 c-18> <Formula c-18>
    Figure PCTKR2015003021-appb-I000204
    Figure PCTKR2015003021-appb-I000204
    <화학식 c-19> <Formula c-19>
    Figure PCTKR2015003021-appb-I000205
    Figure PCTKR2015003021-appb-I000205
    <화학식 c-20> <Formula c-20>
    Figure PCTKR2015003021-appb-I000206
    Figure PCTKR2015003021-appb-I000206
    <화학식 c-21> <Formula c-21>
    Figure PCTKR2015003021-appb-I000207
    Figure PCTKR2015003021-appb-I000207
    <화학식 c-22> <Formula c-22>
    Figure PCTKR2015003021-appb-I000208
    Figure PCTKR2015003021-appb-I000208
    <화학식 c-23> <Formula c-23>
    Figure PCTKR2015003021-appb-I000209
    Figure PCTKR2015003021-appb-I000209
    <화학식 c-24> <Formula c-24>
    Figure PCTKR2015003021-appb-I000210
    Figure PCTKR2015003021-appb-I000210
    <화학식 c-25> <Formula c-25>
    Figure PCTKR2015003021-appb-I000211
    Figure PCTKR2015003021-appb-I000211
    <화학식 c-26> <Formula c-26>
    Figure PCTKR2015003021-appb-I000212
    Figure PCTKR2015003021-appb-I000212
    <화학식 c-27> <Formula c-27>
    Figure PCTKR2015003021-appb-I000213
    Figure PCTKR2015003021-appb-I000213
    <화학식 c-28> <Formula c-28>
    Figure PCTKR2015003021-appb-I000214
    Figure PCTKR2015003021-appb-I000214
    <화학식 c-29> <Formula c-29>
    Figure PCTKR2015003021-appb-I000215
    Figure PCTKR2015003021-appb-I000215
    <화학식 c-30> <Formula c-30>
    Figure PCTKR2015003021-appb-I000216
    Figure PCTKR2015003021-appb-I000216
    <화학식 c-31> <Formula c-31>
    Figure PCTKR2015003021-appb-I000217
    Figure PCTKR2015003021-appb-I000217
    <화학식 c-32> <Formula c-32>
    Figure PCTKR2015003021-appb-I000218
    Figure PCTKR2015003021-appb-I000218
    <화학식 c-33> <Formula c-33>
    Figure PCTKR2015003021-appb-I000219
    Figure PCTKR2015003021-appb-I000219
    <화학식 c-34> <Formula c-34>
    Figure PCTKR2015003021-appb-I000220
    Figure PCTKR2015003021-appb-I000220
    <화학식 c-35> <Formula c-35>
    Figure PCTKR2015003021-appb-I000221
    Figure PCTKR2015003021-appb-I000221
    <화학식 c-36><Formula c-36>
    Figure PCTKR2015003021-appb-I000222
    .
    Figure PCTKR2015003021-appb-I000222
    .
  9. 제2항에 있어서,The method of claim 2,
    화학식 1로 나타내는 화합물에서,In the compound represented by the formula (1),
    상기 Ar1은 트리메틸실릴기; 시아노기; 또는 트리플루오로메틸기로 치환된 페닐기인 화합물.Ar 1 is trimethylsilyl group; Cyano group; Or a phenyl group substituted with a trifluoromethyl group.
  10. 제9항에 있어서,The method of claim 9,
    제9항에 따른 화합물은, 하기 화학식 d-1 내지 d-4의 구조로부터 선택되는 것을 특징으로 하는 화합물:The compound according to claim 9, wherein the compound is selected from the structures of formulas d-1 to d-4:
    <화학식 d-1> <Formula d-1>
    Figure PCTKR2015003021-appb-I000223
    Figure PCTKR2015003021-appb-I000223
    <화학식 d-2> <Formula d-2>
    Figure PCTKR2015003021-appb-I000224
    Figure PCTKR2015003021-appb-I000224
    <화학식 d-3> <Formula d-3>
    Figure PCTKR2015003021-appb-I000225
    Figure PCTKR2015003021-appb-I000225
    <화학식 d-4><Formula d-4>
    Figure PCTKR2015003021-appb-I000226
    .
    Figure PCTKR2015003021-appb-I000226
    .
  11. 제1 전극;A first electrode;
    제1 전극에 대향된 제2 전극;A second electrode opposed to the first electrode;
    제1 전극과 제2 전극 사이에 개재된 발광층; 및A light emitting layer interposed between the first electrode and the second electrode; And
    제1 전극과 발광층 사이에 개재되는 유기층을 포함하고,An organic layer interposed between the first electrode and the light emitting layer,
    상기 유기층은, 제1 유기층 내지 제n 유기층으로 구성되는 n개의 유기층을 포함하며, 여기서, 제1 유기층은 발광층과 접하는 위치에 형성되고, 제1 유기층을 제외한 (n-1)개의 유기층은 제1 유기층과 제1 전극 사이에 적층되는 구조이며, n은 2 내지 5의 정수이고,The organic layer includes n organic layers composed of the first organic layer to the nth organic layer, 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. It is a structure laminated | stacked between an organic layer and a 1st electrode, n is an integer of 2-5,
    상기 제1 유기층은 하기 화학식 1로 나타내는 화합물을 1종 이상 포함하는 발광소자:The first organic layer is a light emitting device comprising at least one compound represented by the formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2015003021-appb-I000227
    Figure PCTKR2015003021-appb-I000227
    상기 화학식 1에 있어서, La, Ar1, Ar2, R1 및 a는 제1항에서 정의한 바와 같다.In Formula 1, L a , Ar 1 , Ar 2 , R 1 and a are as defined in claim 1.
  12. 제11항에 있어서,The method of claim 11,
    제1 유기층은, 제1항에 따른 화학식 1로 나타내는 화합물을 1종 이상 포함하는 단층 구조를 갖는 발광소자.The first organic layer has a single layer structure containing one or more compounds represented by the formula (1) according to claim 1.
  13. 제11항에 있어서,The method of claim 11,
    제1 유기층은, 2층 구조이고,The first organic layer is a two-layer structure,
    2층 구조를 구성하는 각 개별층은, 서로 독립적으로 제1항에 따른 화학식 1로 나타내는 화합물을 1종 이상 포함하되,Each individual layer constituting the two-layer structure, independently of each other comprises at least one compound represented by the formula (1) according to claim 1,
    각 개별층에 포함되는 화합물은 서로 다른 구조를 갖는 것을 특징으로 하는 발광소자.Compounds included in each individual layer has a different structure.
  14. 제11항에 있어서,The method of claim 11,
    제1 유기층은, 2층 구조이고,The first organic layer is a two-layer structure,
    2층 구조 중 어느 한 층은, 제1항에 따른 화학식 1로 나타내는 화합물을 1종 이상 포함하고,Any one layer of the two-layer structure contains at least one compound represented by the formula (1) according to claim 1,
    다른 한 층은, 하기 화학식 2로 나타내는 화합물을 포함하는 발광소자:Another layer is a light emitting device comprising a compound represented by the formula (2):
    [화학식 2][Formula 2]
    Figure PCTKR2015003021-appb-I000228
    Figure PCTKR2015003021-appb-I000228
    상기 화학식 2에서,In Chemical Formula 2,
    Ra, Rb, Rc 및 Rd는 서로 독립적으로, 수소, 탄소수 1 내지 4를 갖는 알킬기 또는 탄소수 6 내지 14를 갖는 아릴기이다.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.
  15. 제12항에 있어서,The method of claim 12,
    제1 유기층의 두께는, 20 Å 내지 400 Å인 발광소자.The light emitting element of the first organic layer has a thickness of 20 kPa to 400 kPa.
  16. 제13항 또는 제14항에 있어서,The method according to claim 13 or 14,
    2층 구조를 구성하는 각 개별층 두께는, 10 Å 내지 200 Å인 발광소자.The light emitting element whose thickness of each individual layer which comprises a 2-layered structure is 10 GPa-200 GPa.
  17. 제11항에 있어서,The method of claim 11,
    유기층은, 제1 유기층을 제외한 (n-1)개의 유기층에 하기 화학식 3으로 나타내는 화합물을 포함하는 발광소자:The organic layer, the light emitting device comprising a compound represented by the following formula (3) in (n-1) organic layers excluding the first organic layer:
    [화학식 3][Formula 3]
    Figure PCTKR2015003021-appb-I000229
    Figure PCTKR2015003021-appb-I000229
    상기 화학식 3에서,In Chemical Formula 3,
    R2 및 R3은 서로 독립적으로 수소, 탄소수 1 내지 6을 갖는 알킬기, 탄소수 6 내지 30을 갖는 아릴기 또는 탄소수 2 내지 20을 갖는 헤테로아릴기이고;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;
    Lb는 -L1-L2-L3-L4-이며,L b is -L 1 -L 2 -L 3 -L 4- ,
    L1, L2, L3 및 L4는 서로 독립적으로 단일결합, -O-, -S-, 탄소수 6 내지 30을 갖는 아릴렌기, 탄소수 2 내지 20을 갖는 헤테로아릴렌기 또는 탄소수 3 내지 20을 갖는 사이클로알킬렌기이되, L1, L2, L3 및 L4가 모두 단일결합인 경우는 제외되고;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;
    Ar3 및 Ar4는 서로 독립적으로 탄소수 6 내지 30을 갖는 아릴기, 탄소수 2 내지 20을 갖는 헤테로아릴기 또는 하기 화학식 4로 나타내는 치환기이며,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),
    [화학식 4][Formula 4]
    Figure PCTKR2015003021-appb-I000230
    Figure PCTKR2015003021-appb-I000230
    상기 화학식 4에서,In Chemical Formula 4,
    X는 O, S 또는 C(R6)(R7)이고,X is O, S or C (R 6 ) (R 7 ),
    R4, R5, R6 및 R7은 서로 독립적으로 탄소수 1 내지 6을 갖는 알킬기, 탄소수 6 내지 30을 갖는 아릴기 또는 탄소수 2 내지 20을 갖는 헤테로아릴기이며,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,
    p는 0 내지 3의 정수이고,p is an integer from 0 to 3,
    q는 0 내지 4의 정수이다.q is an integer of 0-4.
  18. 제17항에 있어서,The method of claim 17,
    화학식 3으로 나타내는 화합물은, 하기 화학식 5로 나타내는 화합물인 발광소자:Compound represented by the formula (3) is a compound represented by the formula (5):
    [화학식 5][Formula 5]
    Figure PCTKR2015003021-appb-I000231
    Figure PCTKR2015003021-appb-I000231
    상기 화학식 5에서,In Chemical Formula 5,
    R2는 탄소수 6 내지 30을 갖는 아릴기이고;R 2 is an aryl group having 6 to 30 carbon atoms;
    R3은 수소이며;R 3 is hydrogen;
    Lb는 탄소수 6 내지 20을 갖는 아릴렌기이고;L b is an arylene group having 6 to 20 carbon atoms;
    Ar3은 탄소수 6 내지 30을 갖는 아릴기 또는 하기 화학식 4로 나타내는 치환기이며,Ar 3 is an aryl group having 6 to 30 carbon atoms or a substituent represented by the following general formula (4),
    [화학식 4][Formula 4]
    Figure PCTKR2015003021-appb-I000232
    Figure PCTKR2015003021-appb-I000232
    상기 화학식 4에서,In Chemical Formula 4,
    X는 O, S 또는 C(R6)(R7)이고,X is O, S or C (R 6 ) (R 7 ),
    R4, R5, R6 및 R7은 서로 독립적으로 탄소수 1 내지 6을 갖는 알킬기 또는 탄소수 6 내지 30을 갖는 아릴기이며,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,
    p는 0 내지 2의 정수이고,p is an integer from 0 to 2,
    q는 0 내지 2의 정수이다.q is an integer of 0-2.
  19. 제18항에 있어서,The method of claim 18,
    화학식 5에서,In Formula 5,
    상기 R2는 페닐기, 바이페닐기, 터페닐기 또는 나프틸기이고;R 2 is a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group;
    R3은 수소이며;R 3 is hydrogen;
    Lb는 페닐렌기, 바이페닐렌기, 터페닐렌기 또는 나프틸렌기이고; 및L b is a phenylene group, a biphenylene group, a terphenylene group or a naphthylene group; And
    Ar3은 페닐기, 바이페닐기, 터페닐기, 나프틸기, 디벤조티에닐기, 디벤조퓨라닐기, 플루오레닐기, 디메틸플루오레닐기 또는 디페닐플루오레닐기인 발광소자.Ar 3 is a phenyl group, biphenyl group, terphenyl group, naphthyl group, dibenzothienyl group, dibenzofuranyl group, fluorenyl group, dimethyl fluorenyl group or diphenyl fluorenyl group.
  20. 제11항에 있어서,The method of claim 11,
    유기층은,The organic layer is
    제1항에 따른 화학식 1로 나타내는 화합물을 1종 이상 포함하는 제1 유기층;A first organic layer comprising at least one compound represented by Formula 1 according to claim 1;
    제17항에 따른 화학식 3으로 나타내는 화합물을 포함하는 제2 유기층; 및A second organic layer comprising a compound represented by Formula 3 according to claim 17; And
    P형 도펀트를 포함하는 제3 유기층을 포함하는 발광소자.A light emitting device comprising a third organic layer containing a p-type dopant.
  21. 제11항에 따른 발광소자를 포함하는 전자장치.An electronic device comprising the light emitting device according to claim 11.
  22. 제21항에 있어서,The method of claim 21,
    전자장치는, 디스플레이 장치 또는 조명 장치인 것을 특징으로 하는 전자장치.The electronic device is a display device or an illumination device.
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WO2016116521A1 (en) * 2015-01-20 2016-07-28 Cynora Gmbh Organic molecules, in particular for use in optoelectronic components

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