WO2014209050A1 - Nouveau composé, élément électroluminescent comprenant celui-ci, et dispositif électronique associé - Google Patents

Nouveau composé, élément électroluminescent comprenant celui-ci, et dispositif électronique associé Download PDF

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WO2014209050A1
WO2014209050A1 PCT/KR2014/005722 KR2014005722W WO2014209050A1 WO 2014209050 A1 WO2014209050 A1 WO 2014209050A1 KR 2014005722 W KR2014005722 W KR 2014005722W WO 2014209050 A1 WO2014209050 A1 WO 2014209050A1
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carbon atoms
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light emitting
substituent
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Korean (ko)
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최정옥
정준호
권오관
김형선
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주식회사 엘엠에스
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Definitions

  • the present invention relates to a novel compound, a light emitting device and an electronic device including the same, and more particularly to a compound for an organic light emitting device, a light emitting device and an electronic device comprising the same.
  • a light emitting device includes a light emitting layer including two electrodes facing each other and a light emitting compound interposed between the electrodes. When a current flows between the electrodes, the light emitting compound generates light.
  • the display device using the light emitting device does not need a separate light source device, and thus the weight, size, and thickness of the display device can be reduced.
  • the display device using the light emitting device has an advantage of excellent viewing angle, contrast ratio, color reproducibility, and the like, and lower power consumption than the display device using the backlight and the liquid crystal.
  • the light emitting device may further include a hole transport layer disposed between the anode and the light emitting layer.
  • the hole transport layer may stabilize an interface between the anode and the light emitting layer and minimize an energy barrier therebetween.
  • the light emitting device has a short light emitting life 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 the light emission life and power efficiency.
  • Patent Document 1 Japanese Laid-Open Patent No. 2008-294161
  • Patent Document 2 Korean Patent Publication No. 2008-0104025
  • an object of the present invention is to provide a novel compound for improving the ability to inject and transport holes in a light emitting device.
  • Another object of the present invention is to provide a light emitting device comprising the compound.
  • Still another object of the present invention is to provide an electronic device including the light emitting device.
  • Ar 1 , Ar 2 , Ar 3 and Ar 4 are each independently hydrogen, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, a hetero having 2 to 60 carbon atoms A cyclic group or the following Formula 2, wherein at least one of Ar 1 , Ar 2 , Ar 3, and Ar 4 represents Formula 2,
  • L a , L b , L c , L d and L e each independently represent * -L 1 -L 2 -L 3- *
  • L 1 , L 2 and L 3 are each independently a single bond, -O-, -S-, an arylene group having 6 to 60 carbon atoms, a heteroarylene group having 2 to 60 carbon atoms, a cycloalkyl having 3 to 60 carbon atoms A ethylene group, a heterocycloalkylene group having 2 to 60 carbon atoms, or the following Chemical Formula 3,
  • R 1 , R 2 , R 3, and R 4 each independently represent hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, or an aryl group having 6 to 60 carbon atoms.
  • At least one of the hydrogen of Formula 1 is each independently an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, 2 carbon atoms Heteroaryl group having 20 to 20, aryloxy group having 6 to 20 carbon atoms, arylthio group having 6 to 20 carbon atoms, alkoxycarbonyl group having 1 to 6 carbon atoms, halogen group, cyano group, nitro group, hydroxyl group And it is substituted or unsubstituted in any one selected from the group consisting of carboxyl groups.
  • a light emitting device includes a hole transport layer including a first electrode, a second electrode, a light emitting layer and the compound represented by the formula (1).
  • the first electrode and the second electrode may face each other, the emission layer may be interposed between the first and second electrodes, and the hole transport layer may be disposed between the first electrode and the emission layer. .
  • the hole transport layer may include a first layer comprising the compound and a P-type dopant, and a second layer comprising the compound.
  • the first layer may be disposed between the first electrode and the light emitting layer
  • the second layer may be disposed between the first layer and the light emitting layer.
  • the second layer may further include a dopant of the same type or different from the P-type dopant of the first layer.
  • the novel compound of the present invention can improve the ability to inject and / or transport holes in the light emitting device.
  • the light emitting efficiency of the light emitting device may be improved, and the life may be increased.
  • the thermal stability (heat resistance) of the light emitting device can be improved.
  • FIG. 1 is a cross-sectional view illustrating a light emitting device according to an embodiment of the present invention.
  • FIG. 2 is a cross-sectional view illustrating a light emitting device according to another embodiment of the present invention.
  • FIG. 3 is a cross-sectional view for describing a light emitting device according to still another embodiment of the present invention.
  • the compound according to the present invention is represented by the following formula (1).
  • Ar 1 , Ar 2 , Ar 3 and Ar 4 are each independently hydrogen, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 60 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, a hetero having 2 to 60 carbon atoms A cyclic group or the following Formula 2, wherein at least one of Ar 1 , Ar 2 , Ar 3, and Ar 4 represents Formula 2,
  • L a , L b , L c , L d and L e each independently represent * -L 1 -L 2 -L 3- *
  • L 1 , L 2 and L 3 are each independently a single bond, -O-, -S-, an arylene group having 6 to 60 carbon atoms, a heteroarylene group having 2 to 60 carbon atoms, a cycloalkyl having 3 to 60 carbon atoms A ethylene group, a heterocycloalkylene group having 2 to 60 carbon atoms, or the following Chemical Formula 3,
  • R 1 , R 2 , R 3, and R 4 each independently represent hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, or an aryl group having 6 to 60 carbon atoms.
  • At least one of the hydrogen of Formula 1 is each independently an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, 2 carbon atoms Heteroaryl group having 20 to 20, aryloxy group having 6 to 20 carbon atoms, arylthio group having 6 to 20 carbon atoms, alkoxycarbonyl group having 1 to 6 carbon atoms, halogen group, cyano group, nitro group, hydroxyl group And it is substituted or unsubstituted in any one selected from the group consisting of carboxyl groups.
  • aryl group is defined as a monovalent substituent derived from an aromatic hydrocarbon.
  • the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a naphthacenyl group, a pyrenyl group, a tolyl group, Biphenylyl group, terphenyl group, chrycenyl group, spirobifluorenyl group, fluorantenyl group, fluorenyl group, fluorenyl group, perylene And a perylenyl group, an indenyl group, an azulenyl group, a heptarenyl group, a penalenyl group, a phenanthrenyl group, and the like.
  • Heterocyclic refers to "aromatic heterocycle” or “heterocyclic” derived from a monocyclic or condensed ring.
  • the heterocyclic group may include at least one of nitrogen (N), sulfur (S), oxygen (O), phosphorus (P), selenium (Se), and silicon (Si) as a hetero atom.
  • heterocyclic group examples include a pyrrolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, and a triazolyl group (triazolyl group, tetrazolyl group, benzotriazolyl group, benzotriazolyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, indole Indolyl group, isoindolyl group, indolizinyl group, indolinzinyl group, purinyl group, inindazolyl group, quinolyl group, quinolyl group, isoquinolyl Isoquinolinyl group, quinolizinyl group, phthalazinyl group, phthalazinyl group, naphthylidinyl group, quinoxalinyl group, quinazolinyl group, quinazolinyl group
  • heterocyclic group may include a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a benzothiadiazolyl group, and a phenothiazinyl group.
  • phenothiazinyl group isoxazolyl group, furazanyl group, furazanyl group, phenoxazinyl group, oxazolyl group, benzoxazolyl group, benzoxazolyl group
  • Compounds containing at least two or more heteroatoms such as an oxadiazolyl group, a pyrazoloxazolyl group, an imidazothiazolyl group, a thienofuranyl group, and the like have.
  • Q 1 and Q 2 each independently represent an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms,
  • R a , R b , R c , R d , R e and R f are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms or carbon atoms The heteroaryl group which has 2-20 is shown.
  • R g , R h , R i and R j are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, or Heteroaryl group which has C2-C20 is shown.
  • the heteroaryl group in each of Formulas 1-1 and 1-2 is substantially the same as the heterocyclic group described above.
  • the heteroaryl group may not include the fused-zurridinyl group represented by Formula 1-1 and the zurridinyl group represented by Formula 1-2.
  • the "heteroaryl group" is substantially the same as described in the formulas 1-1 and 1-2.
  • Alkyl group is defined as a functional group derived from linear or branched saturated hydrocarbons.
  • alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, sec-butyl group, t-butyl group, n-pentyl 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-ethylpropyl group (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 (1,1,2-trimethylpropyl group), 1-propylpropyl group (1-propylpropyl group), 1-methylmethyl group
  • arylene group may mean a divalent substituent derived from the aryl group described above.
  • heteroarylene group may mean a divalent substituent derived from the heteroaryl group described above.
  • the compound represented by Formula 1 may include a compound represented by the following formula (4).
  • Ar 2 , Ar 3 and Ar 4 are each independently hydrogen, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, a heterocyclic group having 2 to 30 carbon atoms, or Formula 5 is represented,
  • L a , L b , L c , L d and L e each independently represent * -L 1 -L 2 -L 3- *
  • L 1 , L 2 and L 3 are each independently a single bond, -O-, -S-, an arylene group having 6 to 30 carbon atoms, a heteroarylene group having 2 to 30 carbon atoms, a cycloalkylene group having 3 to 30 carbon atoms, Heterocycloalkylene group having 2 to 30 carbon atoms or the following formula (6)
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently represent hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms,
  • At least one of the hydrogen of Formula 4 is each independently an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 20 carbon atoms, 2 carbon atoms Heteroaryl group having 20 to 20, aryloxy group having 6 to 20 carbon atoms, arylthio group having 6 to 20 carbon atoms, alkoxycarbonyl group having 1 to 6 carbon atoms, halogen group, cyano group, nitro group, hydroxyl group And it is substituted or unsubstituted in any one selected from the group consisting of carboxyl groups.
  • heterocyclic group of Chemical Formula 1 may be represented by Chemical Formula 7-1 or Chemical Formula 7-2.
  • R 7 , R 8 , R 9 and R 10 each independently represent an alkyl group having 1 to 6 carbon atoms.
  • the compound represented by Formula 4 may include a compound represented by the following formula (8).
  • Ar 2 may represent any one selected from Table 1 below.
  • Ar 3 and Ar 4 may each independently represent hydrogen or any one selected from Table 2 below.
  • L a may represent a single bond or any one selected from Table 3 below.
  • R 1 and R 2 in Formula 8 may each independently represent an alkyl group or a phenyl group having 1 to 6 carbon atoms.
  • substituent No. 5 in Table 1 specifically, the substituent may be represented by the following Chemical Formula 1-1a or the following Chemical Formula 1-1b.
  • Substituent No. 6 in Table 1 may be represented by the following Formula 1-2a or the following Formula 1-2b.
  • substituent 5 of Table 2 may be represented by the following formula 2-1a or 2-2b.
  • Substituent No. 6 in Table 2 may be represented by the following Formula 2-2a or the following Formula 2-2b.
  • Each substituent in Tables 1 to 3 may have various binding positions in the indicated ranges, and overlapping descriptions are omitted.
  • the compound represented by Formula 1 may be any one selected from compounds represented by Structures 1 to 36 below.
  • FIG. 1 is a cross-sectional view illustrating a light emitting device according to an embodiment of the present invention.
  • the light emitting device 100 includes a first electrode 20, a hole transporting layer 30, a light emitting layer 40, and a second electrode 50 formed on the base substrate 10.
  • the light emitting device 100 may be an organic light emitting diode (OLED).
  • the first electrode 20 may be formed on the base substrate 10 with a conductive material.
  • the first electrode 20 may be a transparent electrode.
  • the first electrode 20 may be formed of indium tin oxide (ITO).
  • the first electrode 20 may be an opaque (reflective) electrode.
  • the first electrode 20 may have an ITO / silver (Ag) / ITO structure.
  • the first electrode 20 may be an anode of the light emitting device 100.
  • the hole transport layer 30 is formed on the first electrode 20 and is interposed between the first electrode 20 and the light emitting layer 40.
  • the hole transport layer 30 includes a compound represented by the following Chemical Formula 1 as a hole transport compound.
  • the compound represented by the said Formula (1) is substantially the same as what was demonstrated above as a novel compound which concerns on this invention. Therefore, detailed description of Ar 1 , Ar 2 , Ar 3 , Ar 4 , L a , L b , L c , L d and L e will be omitted.
  • the wavelength of the light emitted by the light emitting layer 40 may vary depending on the type of the compound forming the light emitting layer 40.
  • the second electrode 50 may be formed on the light emitting layer 40 with a conductive material.
  • the second electrode 50 may be an opaque (reflective) electrode.
  • the second electrode 50 may be an aluminum electrode.
  • the first electrode 20 is an opaque electrode
  • the second electrode 50 may be a transparent or translucent electrode.
  • the second electrode 50 may have a thickness of 100 kPa to 150 kPa, and may be an alloy including magnesium and silver.
  • the second electrode 50 may be a cathode of the light emitting device 100.
  • An electron transport layer and / or an electron injection layer may be formed between the emission layer 40 and the second electrode 50 as an electron transport layer.
  • the light emitting device 100 When a current flows between the first and second electrodes 20 and 50 of the light emitting device 100, holes and holes injected from the first electrode 20 into the light emitting layer 40 are formed. Electrons injected into the emission layer 40 from the second electrode 50 combine to form excitons. In the process of transferring the excitons to the ground state, light having a wavelength in a specific region is generated. In this case, the excitons may be singlet excitons, and may also be triplet excitons. Accordingly, the light emitting device 100 may provide light to the outside.
  • the light emitting device 100 includes an electron transporting layer (ETL) and an electron injecting layer (EIL) disposed between the light emitting layer 40 and the second electrode 50. It may further include.
  • the electron transport layer and the electron injection layer may be sequentially stacked on the light emitting layer 40.
  • the light emitting device 100 may include a first blocking layer (not shown) disposed between the first electrode 20 and the light emitting layer 40 and / or the light emitting layer 40 and the second electrode 50. It may further include a second blocking layer (not shown) disposed between.
  • the first blocking layer is disposed between the hole transport layer 30 and the light emitting layer 40, and electrons injected from the second electrode 50 pass through the light emitting layer 40. It may be an electron blocking layer (EBL) that prevents the inflow into the transport layer 30.
  • the first blocking layer may be an exciton blocking layer that prevents excitons formed in the light emitting layer 40 to diffuse in the direction of the first electrode 20 to prevent the excitons from extinction.
  • the first blocking layer may be an exciton dissociation blocking layer (EDBL).
  • the exciton isolation blocking layer prevents excitons formed in the light emitting layer 40 from undergoing 'exciton dissociation' at the interface between the light emitting layer 40 and the hole transporting layer 30 to prevent non-light emission. can do.
  • the compound forming the first blocking layer may be selected to have a similar level of HOMO value as the compound forming the light emitting layer 40.
  • the first blocking layer may include the compound according to the present invention described above.
  • the second blocking layer is disposed between the light emitting layer 40 and the second electrode 50, specifically, the light emitting layer 40 and the electron transporting layer so that holes are formed from the first electrode 20 to the light emitting layer 40. It may be a hole blocking layer (HBL) to prevent the flow into the electron transport layer via). In addition, the second blocking layer may be an exciton blocking layer which prevents excitons formed in the emission layer 40 from diffusing in the direction of the second electrode 50 to prevent the excitons from extinction.
  • HBL hole blocking layer
  • Adjusting the thickness of each of the first and second blocking layers according to the resonance length of the light emitting device 100 may increase the light emission efficiency and adjust the excitons to be formed at the center of the light emitting layer 40. Can be.
  • FIG. 2 is a cross-sectional view illustrating a light emitting device according to another embodiment of the present invention.
  • the light emitting device 102 includes a first electrode 20, a hole transport layer 32, a light emitting layer 40, and a second electrode 50 formed on the base substrate 10. Except for the hole transport layer 32, the description thereof is substantially the same as that described with reference to FIG.
  • the hole transport layer 32 includes a compound represented by Chemical Formula 1 and a P-type dopant. Since the compound included in the hole transport layer 32 is substantially the same as described above, overlapping detailed description thereof will be omitted.
  • the P-type dopant may include a P-type organic dopant and / or a P-type inorganic dopant.
  • P-type organic dopant examples include compounds represented by the following Chemical Formulas 9 to 13, hexadecafluorophthalocyanine (F16CuPc), 11,11,12,12-tetracyanonaphtho-2,6-quinodimethane (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) or Tetracyanoquinodimethane (TCNQ) and the like. These may be used alone or in combination of two or more, respectively.
  • Chemical Formulas 9 to 13 hexadecafluorophthalocyanine (F16CuPc)
  • 11,11,12,12-tetracyanonaphtho-2,6-quinodimethane
  • R represents a cyano group, a sulfone group, a sulfoxide group, a sulfonamide group, a sulfonate group, a nitro group or a trifluoromethyl group.
  • m and n each independently represent an integer of 1 to 5
  • Y 1 and Y 2 may each independently represent an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms.
  • the hydrogen of the aryl group or heteroaryl group represented by Y 1 and Y 2 may be substituted or unsubstituted with an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or a hydroxyl group, and substituted.
  • unsubstituted hydrogen of Y 1 and Y 2 may be each independently substituted or unsubstituted with a halogen group.
  • the compound represented by Chemical Formula 13 may include a compound represented by Chemical Formula 13a or Chemical Formula 13b.
  • Examples of the P-type inorganic dopant include metal oxides and metal halides. Specific examples of the P-type inorganic dopant include 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. . These may be used alone or in combination of two or more, respectively.
  • the P-type dopant may be about 0.5 parts by weight to about 20 parts by weight based on 100 parts by weight of the novel compound according to the present invention, which is a hole transporting compound.
  • 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 hole transporting compound.
  • the P-type dopant may be about 1 part by weight to 10 parts by weight, 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, based on 100 parts by weight of the hole transporting compound. Can be.
  • the P-type dopant When the content of the P-type dopant is about 0.5 part by weight to about 20 parts by weight with respect to 100 parts by weight of the hole transporting compound, the P-type dopant may generate excessive leakage current without reducing the physical properties of the hole-transporting compound. You can prevent it. In addition, the energy barrier at the interface with each of the upper and lower layers in contact with the hole transport layer 32 may be reduced by the P-type dopant.
  • the light emitting device 102 may further include an electron transport layer, an electron injection layer, a first blocking layer, and / or a second blocking layer.
  • Each of the layers is substantially the same as that described in the light emitting device 100 of FIG. 1, and thus, a detailed description thereof will be omitted.
  • the first blocking layer may include the compound according to the present invention described above.
  • the light emitting device 100 illustrated in FIG. 1 may further include an interlayer (not shown).
  • the intermediate layer may be disposed between the first electrode 20 and the hole transport layer 30 of FIG. 1, and may be formed of a compound used as the P-type dopant described with reference to FIG. 2.
  • FIG. 3 is a cross-sectional view for describing a light emitting device according to still another embodiment of the present invention.
  • the light emitting device 104 includes a first electrode 20, a hole transport layer 34, a light emitting layer 40, and a second electrode 50 formed on the base substrate 10. Except for the hole transport layer 34, the description thereof is substantially the same as that described with reference to FIG.
  • the hole transport layer 34 includes a first layer 33a in contact with the first electrode 20 and a second layer 33b disposed between the first layer 33a and the light emitting layer 40. do. That is, the hole transport layer 34 may have a two-layer structure. In addition, the hole transport layer 34 may have a multilayer structure of two or more layers including the first and second layers 33a and 33b.
  • the first and second layers 33a and 33b may include the same kind of hole transport compound.
  • the components of the hole transporting compound included in the first layer 33a and the second layer 33b are reduced, thereby easily injecting holes into the light emitting layer. It can be done.
  • the same host material is used for the first layer 33a and the second layer 33b
  • the first layer 33a and the second layer 33b can be continuously formed in one chamber. There is an advantage that the manufacturing process is simplified and the production time can be shortened. Furthermore, since physical properties such as glass transition temperature between adjacent layers become similar, there is an advantage of increasing durability of the device.
  • the first layer 33a includes a novel compound according to the present invention represented by Chemical Formula 1 and a P-type dopant as a hole transporting compound.
  • the first layer 33a is substantially the same as the hole transport layer 32 described with reference to FIG. 2 except for the thickness. Therefore, redundant description is omitted.
  • the second layer 33b includes the novel compound according to the present invention represented by Chemical Formula 1 as a hole transporting compound, and the hole transporting compound constituting the second layer 33b is formed of the first layer 33a. It may be the same as the hole transporting compound constituting. Since the second layer 33b is also substantially the same as the hole transport layer 30 described with reference to FIG. 1 except for the thickness, detailed descriptions thereof will be omitted.
  • the first and second layers 33a and 33b may include different kinds of hole transport compounds.
  • the hole transporting compound constituting the first and second layers 33a and 33b may be a novel compound according to the present invention represented by Chemical Formula 1, wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 , L a , L b , L c , L d and L e may be each independently different.
  • the compound constituting each of the first and second layers 33a and 33b may be selected to have a HOMO value for efficiently transferring holes to the light emitting layer 40.
  • the second layer 33b may further include a P-type dopant together with the hole transport compound.
  • the types of P-type dopants doped in the first layer 33a and the second layer 33b may be different from each other, and the doping amount may be different even if the same type is used.
  • the content P1 of the P-type dopant doped in the first layer 33a and the content P2 of the P-type dopant doped in the second layer 33b are represented by Equation 1 below. Can be satisfied.
  • Equation 1 “P1” is a content of a doped P-type dopant relative to 100 parts by weight of the hole transporting compound in the first layer 33a, and “P2” is a hole transporting compound 100 in the second layer 33b. The amount of doped P-type dopant to parts by weight.
  • the content of the P-type dopant doped in the first layer 33a is 0.3 to 20 parts by weight, 1 to 15 parts by weight, 2 to 10 parts by weight, or 4 based on 100 parts by weight of the hole transporting compound. To 6 parts by weight.
  • the content of the P-type dopant doped in the second layer 33b is 0.3 to 20 parts by weight, 0.5 to 10 parts by weight, 1 to 8 parts by weight, or 2 to 4 parts by weight based on 100 parts by weight of the hole transporting compound. It may be a minor range.
  • the light emitting device 104 may further include an electron transport layer, an electron injection layer, a first blocking layer and / or a second blocking layer.
  • an electron transport layer an electron injection layer
  • a first blocking layer a first blocking layer
  • a second blocking layer a second blocking layer
  • each of the light emitting devices 100, 102, 104 described above includes a novel compound according to the present invention represented by Chemical Formula 1, the light emitting devices 100, 102, 104 have improved luminous efficiency and lifespan. This can be long.
  • the light emitting devices 100, 102, 104 are directly formed on the base substrate 10, but the first and second light emitting devices 100, 102, and 104 are respectively formed on the base substrate 10.
  • a thin film transistor may be disposed between the first electrode 20 and the base substrate 10 as a driving element for driving a pixel.
  • the first electrode 20 may be a pixel electrode connected to the thin film transistor.
  • the first electrode 20 is a pixel electrode, the first electrode 20 is disposed separately from each other in the plurality of pixels, and the base substrate 10 is disposed along an edge of the first electrode 20.
  • the barrier rib pattern may be formed so that layers stacked on the first electrode 20 disposed in adjacent pixels may be separated from each other. That is, although not shown in the drawings, the light emitting devices 100, 102, and 104 may be used in a display device that displays an image without a backlight.
  • the light emitting devices 100, 102, and 104 may be used as lighting devices.
  • the light emitting devices 100, 102, 104 illustrated in the present invention may be used in various electronic devices such as the display device or the lighting device.
  • reaction mixture was cooled, dissolved in 60 mL of tetrahydrofuran (THF), added to a 1 L vessel containing 350 mL of methanol, and stirred for 30 minutes. This was filtered to yield about 13 g of compound 3 as a light gray solid (yield 81%).
  • THF tetrahydrofuran
  • reaction mixture was cooled, dissolved in 50 mL of tetrahydrofuran (THF), added to a 1 L vessel containing 300 mL of methanol, and stirred for 20 minutes. This was filtered to yield about 11 g of compound 4 as a gray solid (yield 82%).
  • THF tetrahydrofuran
  • reaction mixture was cooled, dissolved in 100 mL of tetrahydrofuran (THF), added to a 1 L container containing 500 mL of methanol, and stirred for 60 minutes. This was filtered to yield about 20 g of compound 6 as an ivory solid (yield 86%).
  • THF tetrahydrofuran
  • reaction mixture was cooled, dissolved in 50 mL of tetrahydrofuran (THF), added to a 1 L vessel containing 300 mL of methanol, and stirred for 50 minutes. This was filtered to yield about 12 g of compound 7 as a light gray solid (yield 88%).
  • THF tetrahydrofuran
  • a compound according to Example 1 was deposited as a host material of the hole transporting layer at a rate of 1 ⁇ / sec and simultaneously represented by the following P-type dopant: (HAT-CN) was co-evaporated at a rate of about 3 parts by weight with respect to 100 parts by weight of the host material to form a first layer having a thickness of 100 mm.
  • the compound according to Example 1 was deposited on the first layer to a thickness of 300 mm 3 to form a second layer.
  • MCBP represented by Formula 15 and Ir (ppy) 3 represented by Formula 16 were co-deposited on the second layer at a weight ratio of 100: 9 to form a light emitting layer having a thickness of about 400 GPa, and mCBP was formed on the light emitting layer by about 50 GPa thick. Deposition formed a blocking layer.
  • the light emitting device A-1 including the compound according to Example 1 of the present invention was prepared.
  • the light emitting device A-1 is manufactured by using each of the compounds according to Examples 2 to 8 instead of the compound according to Example 1 as a host material of the first layer and the second layer.
  • Light emitting devices A-2 to A-8 were manufactured through the same steps as those in the above steps.
  • the light emitting devices A-1 to A-8 and the comparative devices 1 to 3 were respectively dispensed with a UV curing sealant at the edge of the cover glass with a moisture absorbent (Getter) in a glove box in a nitrogen atmosphere. Each of the and the comparative elements and the cover glass were bonded and cured by irradiation with UV light.
  • the power efficiency was measured based on the value when the luminance was 1,000 cd / m 2 .
  • the results are shown in Table 4.
  • the lifespan of each of the light emitting elements A-1 to A-8 and the comparative elements 1 to 3 was measured. The results are shown in Table 4.
  • T 80 means the time taken for the luminance of the light emitting device to be 80% of the initial luminance when the initial luminance of the light emitting device is 10,000 cd / m 2 . Values for lifetime can be converted based on conversions known to those skilled in the art.
  • the power efficiency of the light emitting elements A-1 to A-8 is 27.8 lm / W, 29.9 lm / W, 24.8 lm / W, 25.9 lm / W, 19.8 lm / W, 22.5 lm / W, respectively. It can be seen that 17.4 lm / W and 20.7 lm / W. That is, it can be seen that the power efficiency of the light emitting device manufactured using the compounds according to Examples 1 to 8 of the present invention is at least about 17.4 lm / W.
  • the power efficiency of the comparative devices 1 to 3 is 11.3 lm / W, 14.8 lm / W and 12.9 lm / W, respectively, so that the power efficiency of the light emitting devices manufactured using the compounds according to Examples 1 to 8 of the present invention is It turns out that it is better than the power efficiency of the comparative elements 1-3.
  • Comparative element 2 having the maximum power efficiency among Comparative Elements 1 to 3 and light emitting element A-7 having the minimum power efficiency among light emitting elements A-1 to A-8
  • the power efficiency of the device has been increased by at least about 17%.
  • the lifespans of the light emitting elements A-1 to A-8 are 151 hours, 169 hours, 141 hours, 159 hours, 127 hours, 135 hours, 113 hours, and 119 hours, respectively. It can be seen that the 66 hours, 79 hours and 71 hours. When comparing the lifetime of Comparative Element 2 and the lifetime of Light Emitting Device A-7, it can be seen that the lifetime of the light emitting device using the compound according to the present invention is at least about 43% longer.
  • HAT-CN represented by Chemical Formula 14 was deposited to a thickness of about 100 GPa to form a first layer, and NPB (N, N ') on the first layer.
  • NPB N, N '
  • -diphenyl-N, N'-bis (1-naphthyl) -1,1'-biphenyl-4,4'-diamine was deposited to a thickness of about 300 mm 3 to form a second layer.
  • a first blocking layer having a thickness of about 100 ⁇ m was formed on the second blocking layer with the compound of Example 1, and mCBP represented by Chemical Formula 15 and Ir (ppy) 3 represented by Chemical Formula 16 were formed on the first blocking layer.
  • mCBP represented by Chemical Formula 15 and Ir (ppy) 3 represented by Chemical Formula 16 were formed on the first blocking layer.
  • MCBP was deposited on the emission layer again to a thickness of about 50 mW to form a second blocking layer.
  • the compound represented by Formula 17 and Liq represented by Formula 18 were co-deposited at a weight ratio of 50:50 on the second blocking layer to form an electron transport layer having a thickness of about 360 kV. Subsequently, Liq was deposited on the electron transport layer again to a thickness of about 5 kW to form an electron injection layer.
  • a second electrode using an aluminum thin film having a thickness of 1,000 ⁇ was formed to manufacture light emitting device B-1 including the compound according to Example 1 of the present invention.
  • the first blocking layer instead of the compound according to Example 1 of the present invention, using the compounds according to Examples 2 to 8 of the present invention to manufacture the light emitting device B-1
  • the light emitting devices B-2 to B-8 were manufactured through the same steps as those of the step.
  • Comparative device 4 was manufactured in the same manner as in the manufacturing of the light emitting device B-1, except that the first blocking layer was manufactured using the compound according to Comparative Example 1 represented by Chemical Formula a.
  • the luminance was 1,000 cd / in substantially the same manner as the power efficiency measurement experiments for the light emitting elements A-1 to A-8.
  • the power efficiency was measured based on the value at m 2 .
  • the lifetimes of each of the light emitting elements B-1 to B-8 and the comparative elements 4 to 6 were measured in substantially the same manner as the life evaluation experiments for the light emitting elements A-1 to A-8.
  • Table 5 shows the results of power efficiency and lifespan of the light emitting elements B-1 to B-8 and the comparative elements 4 to 6, respectively.
  • the unit of the result of measuring the power efficiency is lm / W.
  • T 80 means the time taken for the luminance of the light emitting device to be 80% of the initial luminance when the initial luminance of the light emitting device is 10,000 cd / m 2 . Values for lifetime can be converted based on conversions known to those skilled in the art.
  • the power efficiency of the light emitting elements B-1 to B-8 is 25.9 lm / W, 27.4 lm / W, 28.6 lm / W, 26.3 lm / W, 35.7 lm / W, 33.8 lm / W, respectively. It can be seen that 34.5 lm / W and 29.2 lm / W. On the other hand, it can be seen that the power efficiency of the comparative elements 4 to 6 are 12.7 lm / W, 15.9 lm / W and 14.2 lm / W, respectively.
  • the power efficiency of the light emitting device manufactured using the compounds according to Examples 1 to 8 of the present invention is better than that of the comparative devices 4 to 6.
  • Comparative element 5 having the maximum power efficiency among Comparative elements 4 to 6 and Light emitting element B-1 having the minimum power efficiency among light emitting elements B-1 to B-8 light emission using the compound according to the present invention It can be seen that the power efficiency of the device has been increased by at least about 62%.
  • the lifespans of the light emitting elements B-1 to B-8 are 114 hours, 137 hours, 129 hours, 116 hours, 148 hours, 159 hours, 163 hours, and 141 hours, respectively, while the lifetimes of the comparative elements 4 to 6 are 73 hours. It can be seen that the hour, 83 hours and 76 hours. When comparing the lifetime of the comparative element 5 and the lifetime of the light emitting element B-1, it can be seen that the lifetime of the light emitting element using the compound according to the present invention is at least 37% longer.
  • NPB is deposited as a host material of the hole transporting layer at a rate of 1 ⁇ / sec, and at the same time, the P-type dopant (HAT-CN) represented by Formula 14 is formed on the host material.
  • HAT-CN P-type dopant
  • NPB was deposited to a thickness of 300 kHz on the first layer to form a second layer.
  • a first blocking layer having a thickness of about 100 ⁇ s is formed on the second blocking layer with the compound according to Example 1, and mCBP represented by Chemical Formula 15 and Ir (ppy) 3 represented by Chemical Formula 16 are formed on the first blocking layer.
  • MCBP was deposited on the emission layer again to a thickness of about 50 mW to form a second blocking layer.
  • the compound represented by Formula 17 and Liq represented by Formula 18 were co-deposited at a weight ratio of 50:50 on the second blocking layer to form an electron transport layer having a thickness of about 360 kV. Subsequently, an electron injection layer having a thickness of about 5 kW was formed on the electron transport layer again using Liq.
  • a second electrode using an aluminum thin film having a thickness of 1,000 ⁇ was formed to manufacture a light emitting device C-1 including the compound according to Example 1 of the present invention.
  • Comparative device 7 was manufactured in the same manner as in the manufacturing of the light emitting device C-1, except that the first blocking layer was manufactured using the compound according to Comparative Example 1 represented by Chemical Formula a.
  • the first blocking layer is compared with substantially the same process except for using the compounds according to Comparative Examples 2 and 3 represented by Formula b and Formula c. Devices 8 and 9 were prepared, respectively.
  • the luminance was 1,000 cd / in substantially the same manner as the power efficiency measurement experiments for the light emitting devices A-1 to A-10.
  • the power efficiency was measured based on the value at m 2 .
  • Table 6 shows the results of power efficiency and lifespan of the light emitting elements C-1 to C-8 and the comparative elements 7 to 9, respectively.
  • the unit of the result of measuring the power efficiency is lm / W.
  • T 80 means the time taken for the luminance of the light emitting device to be 80% of the initial luminance when the initial luminance of the light emitting device is 10,000 cd / m 2 . Values for lifetime can be converted based on conversions known to those skilled in the art.
  • the power efficiency of each of the light emitting devices C-1 to C-8 is 26.8 lm / W, 28.9 lm / W, 29.1 lm / W, 27.8 lm / W, 36.8 lm / W, 34.7 lm / W, It can be seen that it is 35.9 lm / W and 30.7 lm / W.
  • the power efficiency of each of the comparative elements 7 to 9 is 13.8 lm / W, 16.3 lm / W, and 15.1 lm / W.
  • the power efficiency of the light emitting device manufactured using the compounds according to Examples 1 to 8 of the present invention is better than that of the comparative devices 7 to 9.
  • the comparative element 8 having the maximum power efficiency among the comparative elements 7 to 9 and the light emitting element C-1 having the minimum power efficiency among the light emitting elements C-1 to C-8 the light emission using the compound according to the present invention It can be seen that the power efficiency of the device has been increased by at least about 64%.
  • the lifetimes of the light emitting elements C-1 to C-8 are 119 hours, 141 hours, 137 hours, 122 hours, 157 hours, 165 hours, 179 hours and 150 hours, respectively, while the lifetimes of the comparative elements 7 to 9 are 83. It can be seen that the time, 91 hours and 85 hours. When comparing the lifespan of the comparative device 8 and the light emitting device C-1, it can be seen that the life of the light emitting device using the compound according to the present invention is at least 30% longer.

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Abstract

La présente invention concerne un nouveau composé, un élément électroluminescent le comprenant, et un dispositif électronique. En particulier, la présente invention concerne un composé pour diode électroluminescente organique, un élément électroluminescent la comprenant, et un dispositif électronique.
PCT/KR2014/005722 2013-06-27 2014-06-27 Nouveau composé, élément électroluminescent comprenant celui-ci, et dispositif électronique associé WO2014209050A1 (fr)

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CN111196822B (zh) * 2018-11-20 2024-02-27 北京夏禾科技有限公司 含有硅芴基和芴基结构的化合物及含有该化合物的电致发光器件

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