WO2014209050A1 - Novel compound, light-emitting element including same, and electronic device - Google Patents
Novel compound, light-emitting element including same, and electronic device Download PDFInfo
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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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- MGMSQFNDUNSQLX-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-c(cc1)cc(c2ccccc22)c1[n]2-c1ccccc1)c(cc1)cc2c1-c1ccccc1[SiH-]2(c1ccccc1)c1ccccc1 Chemical compound c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c(cc1)ccc1-c(cc1)cc(c2ccccc22)c1[n]2-c1ccccc1)c(cc1)cc2c1-c1ccccc1[SiH-]2(c1ccccc1)c1ccccc1 MGMSQFNDUNSQLX-UHFFFAOYSA-N 0.000 description 1
- UNINOZLXUDSWOA-UHFFFAOYSA-N c(cc1)ccc1[Si+]1(c2ccccc2-c2c1cccc2)c1ccccc1 Chemical compound c(cc1)ccc1[Si+]1(c2ccccc2-c2c1cccc2)c1ccccc1 UNINOZLXUDSWOA-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Images
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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
The present invention relates to a novel compound, a light-emitting element including the same, and an electronic device and, more specifically, to a compound for an organic light-emitting diode, a light-emitting element including the same, and an electronic device.
Description
본 발명은 신규한 화합물, 이를 포함하는 발광 소자 및 전자 장치에 관한 것으로, 더욱 상세하게는 유기 발광 소자용 화합물, 이를 포함하는 발광 소자 및 전자 장치에 관한 것이다.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.
일반적으로, 발광 소자는 서로 마주하는 2개의 전극들 및 상기 전극들 사이에 개재된 발광 화합물을 포함하는 발광층을 포함한다. 상기 전극들 사이에 전류를 흘려주면, 상기 발광 화합물이 광을 생성한다. 상기 발광 소자를 이용하는 표시 장치는 별도의 광원 장치가 필요 없어, 상기 표시 장치의 무게, 사이즈나 두께를 감소시킬 수 있다. 또한, 상기 발광 소자를 이용하는 표시 장치는, 백라이트 및 액정을 이용하는 표시 장치에 비해 시야각, 대비비(contrast ratio), 색재현성 등이 우수하고, 소비전력이 낮은 장점이 있다.In general, 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. In addition, 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.
상기 발광 소자는 양극과 상기 발광층 사이에 배치된 정공 수송층을 더 포함할 수 있다. 상기 정공 수송층은 상기 양극과 상기 발광층 사이의 계면을 안정화시키고 이들 사이의 에너지 장벽을 최소화시킬 수 있다.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.
그러나, 아직까지 발광 소자는 발광 수명이 짧고 전력 효율이 낮은 문제점이 있다. 이와 같은 문제점들을 해결하기 위해서, 발광 소자의 재료로서 다양한 화합물들이 개발되고 있지만 발광 수명 및 전력 효율을 모두 만족시키는 발광 소자를 제조하는데 한계가 있다.However, the light emitting device has a short light emitting life 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 the light emission life and power efficiency.
[선행기술문헌][Preceding technical literature]
(특허문헌 1) 일본공개특허 제2008-294161호(Patent Document 1) Japanese Laid-Open Patent No. 2008-294161
(특허문헌 2) 한국공개특허 제2008-0104025호(Patent Document 2) Korean Patent Publication No. 2008-0104025
이에, 본 발명의 기술적 과제는 이러한 점에서 착안된 것으로 본 발명의 목적은 발광 소자에서 정공의 주입 및 수송 능력을 향상시키기 위한 신규한 화합물을 제공하는 것이다.Accordingly, the technical problem of the present invention was conceived in this respect, and 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.
본 발명의 다른 목적은 상기 화합물을 포함하는 발광 소자를 제공하는 것이다.Another object of the present invention is to provide a light emitting device comprising the compound.
본 발명의 또 다른 목적은 상기 발광 소자를 포함하는 전자 장치를 제공하는 것이다.Still another object of the present invention is to provide an electronic device including the light emitting device.
상기 본 발명의 목적을 실현하기 위한 일 실시예에 따른 화합물은 하기 화학식 1로 나타낸다.Compound according to an embodiment for realizing the object of the present invention is represented by the following formula (1).
<화학식 1><Formula 1>
상기 화학식 1에서,In Chemical Formula 1,
Ar1, Ar2, Ar3 및 Ar4는 각각 독립적으로 수소, 탄소수 1 내지 30을 갖는 알킬기, 탄소수 6 내지 60을 갖는 아릴기, 탄소수 3 내지 60을 갖는 시클로알킬기, 탄소수 2 내지 60을 갖는 헤테로고리기 또는 하기 화학식 2를 나타내되, Ar1, Ar2, Ar3 및 Ar4 중 적어도 하나는 하기 화학식 2를 나타내고,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,
<화학식 2><Formula 2>
La, Lb, Lc, Ld 및 Le는 각각 독립적으로 *-L1-L2-L3-*을 나타내고,L a , L b , L c , L d and L e each independently represent * -L 1 -L 2 -L 3- *,
L1, L2 및 L3은 각각 독립적으로 단일 결합, -O-, -S-, 탄소수 6 내지 60을 갖는 아릴렌기, 탄소수 2 내지 60을 갖는 헤테로아릴렌기, 탄소수 3 내지 60을 갖는 시클로알킬렌기, 탄소수 2 내지 60을 갖는 헤테로시클로알킬렌기 또는 하기 화학식 3을 나타내며,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,
<화학식 3><Formula 3>
상기 화학식 2 및 3에서, R1, R2, R3 및 R4는 각각 독립적으로 수소, 탄소수 1 내지 10을 갖는 알킬기, 탄소수 3 내지 60을 갖는 시클로알킬기 또는 탄소수 6 내지 60을 갖는 아릴기를 나타내고,In Formulas 2 and 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. ,
상기 화학식 1의 수소들 중 하나 이상은 각각 독립적으로 탄소수 1 내지 6을 갖는 알킬기, 탄소수 2 내지 6을 갖는 알케닐기, 탄소수 1 내지 6을 갖는 알콕시기, 탄소수 6 내지 20을 갖는 아릴기, 탄소수 2 내지 20을 갖는 헤테로아릴기, 탄소수 6 내지 20을 갖는 아릴옥시기, 탄소수 6 내지 20을 갖는 아릴티오기, 탄소수 1 내지 6을 갖는 알콕시카르보닐기, 할로겐기, 시아노기, 나이트로기, 하이드록시기 및 카르복시기로 이루어진 군으로부터 선택된 어느 하나로 치환 또는 비치환된다.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.
상기 본 발명의 또 다른 목적을 실현하기 위한 일 실시예에 따른 발광 소자는 제1 전극, 제2 전극, 발광층 및 상기 화학식 1로 나타내는 화합물을 포함하는 정공 수송성층을 포함한다. 상기 제1 전극 및 상기 제2 전극은 서로 마주하고, 상기 발광층은 상기 제1 및 제2 전극들 사이에 개재될 수 있으며, 상기 정공 수송성층은 상기 제1 전극과 상기 발광층 사이에 배치될 수 있다.A light emitting device according to an embodiment for realizing another object of the present invention 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. .
일 실시예에서, 상기 정공 수송성층은 상기 화합물 및 P형 도펀트를 포함하는 제1 층과, 상기 화합물을 포함하는 제2 층을 포함할 수 있다. 예를 들어, 상기 제1 층은 상기 제1 전극과 상기 발광층 사이에 배치되고, 상기 제2 층은 상기 제1 층과 상기 발광층 사이에 배치될 수 있다. 이때, 상기 제2 층이 상기 제1 층의 P형 도펀트와 실질적으로 동일하거나 다른 종류의 도펀트를 더 포함할 수 있다.In one embodiment, the hole transport layer may include a first layer comprising the compound and a P-type dopant, and a second layer comprising the compound. For example, the first layer may be disposed between the first electrode and the light emitting layer, and the second layer may be disposed between the first layer and the light emitting layer. In this case, the second layer may further include a dopant of the same type or different from the P-type dopant of the first layer.
이와 같은 신규한 화합물, 이를 포함하는 발광 소자 및 전자 장치에 따르면, 본 발명의 신규한 화합물이 발광 소자에서 정공(hole)의 주입 및/또는 수송 능력을 향상시킬 수 있다.According to such a novel compound, a light emitting device and an electronic device including the same, the novel compound of the present invention can improve the ability to inject and / or transport holes in the light emitting device.
또한, 상기 화합물을 이용함으로써 상기 발광 소자의 발광 효율을 향상시키고, 수명이 증가될 수 있다. 또한, 상기 발광 소자의 열적 안정성(내열성)을 향상시킬 수 있다.In addition, by using the compound, the light emitting efficiency of the light emitting device may be improved, and the life may be increased. In addition, the thermal stability (heat resistance) of the light emitting device can be improved.
도 1은 본 발명의 일 실시예에 따른 발광 소자를 설명하기 위한 단면도이다.1 is a cross-sectional view illustrating a light emitting device according to an embodiment of the present invention.
도 2는 본 발명의 다른 실시예에 따른 발광 소자를 설명하기 위한 단면도이다.2 is a cross-sectional view illustrating a light emitting device according to another embodiment of the present invention.
도 3은 본 발명의 또 다른 실시예에 따른 발광 소자를 설명하기 위한 단면도이다.3 is a cross-sectional view for describing a light emitting device according to still another embodiment of the present invention.
이하에서는, 본 발명에 따른 신규한 화합물에 대해서 먼저 설명하고, 상기 화합물을 포함하는 발광 소자에 대해서 첨부한 도면들을 참조하여 보다 상세하게 설명하기로 한다.Hereinafter, a novel compound according to the present invention will be described first, and a light emitting device including the compound will be described in more detail with reference to the accompanying drawings.
본 발명에 따른 화합물은 하기 화학식 1로 나타낸다.The compound according to the present invention is represented by the following formula (1).
<화학식 1><Formula 1>
상기 화학식 1에서,In Chemical Formula 1,
Ar1, Ar2, Ar3 및 Ar4는 각각 독립적으로 수소, 탄소수 1 내지 30을 갖는 알킬기, 탄소수 6 내지 60을 갖는 아릴기, 탄소수 3 내지 60을 갖는 시클로알킬기, 탄소수 2 내지 60을 갖는 헤테로고리기 또는 하기 화학식 2를 나타내되, Ar1, Ar2, Ar3 및 Ar4 중 적어도 하나는 하기 화학식 2를 나타내고,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,
<화학식 2><Formula 2>
La, Lb, Lc, Ld 및 Le는 각각 독립적으로 *-L1-L2-L3-*을 나타내고,L a , L b , L c , L d and L e each independently represent * -L 1 -L 2 -L 3- *,
L1, L2 및 L3은 각각 독립적으로 단일 결합, -O-, -S-, 탄소수 6 내지 60을 갖는 아릴렌기, 탄소수 2 내지 60을 갖는 헤테로아릴렌기, 탄소수 3 내지 60을 갖는 시클로알킬렌기, 탄소수 2 내지 60을 갖는 헤테로시클로알킬렌기 또는 하기 화학식 3을 나타내며,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,
<화학식 3><Formula 3>
상기 화학식 2 및 3에서, R1, R2, R3 및 R4는 각각 독립적으로 수소, 탄소수 1 내지 10을 갖는 알킬기, 탄소수 3 내지 60을 갖는 시클로알킬기 또는 탄소수 6 내지 60을 갖는 아릴기를 나타내고,In Formulas 2 and 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. ,
상기 화학식 1의 수소들 중 하나 이상은 각각 독립적으로 탄소수 1 내지 6을 갖는 알킬기, 탄소수 2 내지 6을 갖는 알케닐기, 탄소수 1 내지 6을 갖는 알콕시기, 탄소수 6 내지 20을 갖는 아릴기, 탄소수 2 내지 20을 갖는 헤테로아릴기, 탄소수 6 내지 20을 갖는 아릴옥시기, 탄소수 6 내지 20을 갖는 아릴티오기, 탄소수 1 내지 6을 갖는 알콕시카르보닐기, 할로겐기, 시아노기, 나이트로기, 하이드록시기 및 카르복시기로 이루어진 군으로부터 선택된 어느 하나로 치환 또는 비치환된다.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.
본 발명에서, "아릴기" 는 방향족 탄화수소로부터 유도된 1가의 치환기로 정의된다.In the present invention, "aryl group" is defined as a monovalent substituent derived from an aromatic hydrocarbon.
상기 아릴기의 구체적인 예로서는, 페닐기(phenyl group), 나프틸기(naphthyl group), 안트라세닐기(anthracenyl group), 나프타세닐기(naphthacenyl group), 피레닐기(pyrenyl group), 톨릴기(tolyl group), 바이페닐기(biphenylyl group), 터페닐기(terphenyl group), 크리세닐기(chrycenyl group), 스피로바이플루오레닐(spirobifluorenyl group), 플루오란테닐(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.Specific examples of 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.
“헤테로고리기”는 단환 또는 축합환으로부터 유도된 “방향족 복소환”또는 “헤테로사이클릭”을 나타낸다. 상기 헤테로고리기는, 헤테로 원자로서 질소(N), 황(S), 산소(O), 인(P), 셀레늄(Se) 및 규소(Si) 중에서 적어도 하나를 포함할 수 있다."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.
상기 헤테로고리기의 구체적인 예로서는, 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), 페난트롤리닐기(phenanthrolinyl group), 페나지닐기(phenazinyl group), 이미다조피리디닐기(imidazopyridinyl group), 이미다조피리미디닐기(imidazopyrimidinyl group), 피라졸로피리디닐기(pyrazolopyridinyl group), 하기 화학식 1-1로 나타내는 융합-줄러리디닐기(fused-julolidinyl group) 또는 하기 화학식 1-2로 나타내는 줄러리디닐기(julolidinyl group) 등을 포함하는 함질소 헤테로아릴기; 티에닐기(thienyl group), 벤조티에닐기(benzothienyl group), 디벤조티에닐기(dibenzothienyl group) 등을 포함하는 황함유 헤테로아릴기; 푸릴기(furyl group), 피라닐기(pyranyl group), 사이클로펜타피라닐기(cyclopentapyranyl group), 벤조푸라닐기(benzofuranyl group), 이소벤조푸라닐기(isobenzofuranyl group), 디벤조푸라닐기(dibenzofuranyl group) 등을 포함하는 함산소 헤테로아릴기 등을 들 수 있다. 또한, 상기 헤테로고리기의 구체적인 예로서는, 티아졸릴기(thiazolyl group), 이소티아졸릴기(isothiazolyl group), 벤조티아졸릴기(benzothiazolyl group), 벤조티아디아졸릴기(benzothiadiazolyl group), 페노티아지닐기(phenothiazinyl group), 이속사졸릴기(isoxazolyl group), 푸라자닐기(furazanyl group), 페녹사지닐기(phenoxazinyl group), 옥사졸릴기(oxazolyl group), 벤즈옥사졸릴기(benzoxazolyl group), 옥사디아졸릴기(oxadiazolyl group), 피라졸로옥사졸릴기(pyrazoloxazolyl group), 이미다조티아졸릴기(imidazothiazolyl group), 티에노푸라닐기(thienofuranyl group) 등의 적어도 2개 이상의 헤테로 원자를 포함하는 화합물들을 들 수 있다.Specific examples of the heterocyclic group 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 Cinolinyl group, pterididinyl group, imida Zotriazinyl group (imidazotriazinyl group), acridinyl group (acridinyl group), phenanthridinyl group (phenanthridinyl group), carbazolyl group, phenanthrolinyl group (phenanthrolinyl group), phenazinyl group, An imidazopyridinyl group, an imidazopyrimidinyl group, a pyrazolopyridinyl group, a fused-julolidinyl group represented by the following formula 1-1, or A nitrogen-containing heteroaryl group including a julolidinyl group represented by the following Chemical Formula 1-2; 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. In addition, specific examples of the 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.
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
상기 화학식 1-1에서, Q1 및 Q2는 각각 독립적으로 탄소수 6 내지 60을 갖는 아릴기 또는 탄소수 2 내지 60을 갖는 헤테로아릴기를 나타내고,In Formula 1-1, 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,
Ra, Rb, Rc, Rd, Re 및 Rf는 각각 독립적으로 수소, 탄소수 1 내지 6을 갖는 알킬기, 탄소수 1 내지 6을 갖는 알콕시기, 탄소수 6 내지 20을 갖는 아릴기 또는 탄소수 2 내지 20을 갖는 헤테로아릴기를 나타낸다. 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.
상기 화학식 1-2에서, Rg, Rh, Ri 및 Rj는 각각 독립적으로 수소, 탄소수 1 내지 6을 갖는 알킬기, 탄소수 1 내지 6을 갖는 알콕시기, 탄소수 6 내지 20을 갖는 아릴기 또는 탄소수 2 내지 20을 갖는 헤테로아릴기를 나타낸다.In Formula 1-2, 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.
이때, 화학식 1-1 및 1-2 각각에서 헤테로아릴기는, 상기에서 설명한 헤테로고리기와 실질적으로 동일하다. 다만, 헤테로아릴기는 상기 화학식 1-1로 나타내는 융합-줄러리디닐기 및 상기 화학식 1-2로 나타내는 줄러리디닐기는 포함하지 않을 수 있다. 이하, "헤테로아릴기" 는 화학식 1-1 및 1-2에서 설명한 것과 실질적으로 동일하다.In this case, the heteroaryl group in each of Formulas 1-1 and 1-2 is substantially the same as the heterocyclic group described above. However, the heteroaryl group may not include the fused-zurridinyl group represented by Formula 1-1 and the zurridinyl group represented by Formula 1-2. Hereinafter, the "heteroaryl group" is substantially the same as described in the formulas 1-1 and 1-2.
"알킬기" 는 직쇄(linear) 또는 분지(branched) 상 포화탄화수소로부터 유도된 작용기로 정의된다."Alkyl group" is defined as a functional group derived from linear or branched saturated hydrocarbons.
상기 알킬기의 구체적인 예로서는, 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.Specific examples of the alkyl group 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-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-dimeth ylbutyl 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, "아릴렌기" 는 상기에서 설명한 아릴기로부터 유도된 2가의 치환기를 의미할 수 있다.In addition, "arylene group" may mean a divalent substituent derived from the aryl group described above.
또한, "헤테로아릴렌기" 는 상기에서 설명한 헤테로아릴기로부터 유도된 2가의 치환기를 의미할 수 있다.In addition, "heteroarylene group" may mean a divalent substituent derived from the heteroaryl group described above.
일 실시예에서, 상기 화학식 1로 나타내는 화합물은 하기 화학식 4로 나타내는 화합물을 포함할 수 있다.In one embodiment, the compound represented by Formula 1 may include a compound represented by the following formula (4).
<화학식 4><Formula 4>
상기 화학식 4에서,In Chemical Formula 4,
Ar2, Ar3 및 Ar4는 각각 독립적으로 수소, 탄소수 1 내지 30을 갖는 알킬기, 탄소수 6 내지 30을 갖는 아릴기, 탄소수 3 내지 30을 갖는 시클로알킬기, 탄소수 2 내지 30을 갖는 헤테로고리기 또는 하기 화학식 5를 나타내고,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,
<화학식 5><Formula 5>
La, Lb, Lc, Ld 및 Le는 각각 독립적으로 *-L1-L2-L3-*을 나타내고,L a , L b , L c , L d and L e each independently represent * -L 1 -L 2 -L 3- *,
L1, L2 및 L3은 각각 독립적으로 단일 결합, -O-, -S-, 탄소수 6 내지 30의 아릴렌기, 탄소수 2 내지 30을 갖는 헤테로아릴렌기, 탄소수 3 내지 30의 시클로알킬렌기, 탄소수 2 내지 30을 갖는 헤테로시클로알킬렌기 또는 하기 화학식 6을 나타내며,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)
<화학식 6><Formula 6>
R1, R2, R3, R4, R5 및 R6은 각각 독립적으로 수소, 탄소수 1 내지 10을 갖는 알킬기, 탄소수 3 내지 30을 갖는 시클로알킬기, 탄소수 6 내지 30을 갖는 아릴기를 나타내고,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,
상기 화학식 4의 수소들 중 하나 이상은 각각 독립적으로 탄소수 1 내지 6을 갖는 알킬기, 탄소수 2 내지 6을 갖는 알케닐기, 탄소수 1 내지 6을 갖는 알콕시기, 탄소수 6 내지 20을 갖는 아릴기, 탄소수 2 내지 20을 갖는 헤테로아릴기, 탄소수 6 내지 20을 갖는 아릴옥시기, 탄소수 6 내지 20을 갖는 아릴티오기, 탄소수 1 내지 6을 갖는 알콕시카르보닐기, 할로겐기, 시아노기, 나이트로기, 하이드록시기 및 카르복시기로 이루어진 군으로부터 선택된 어느 하나로 치환 또는 비치환된다.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.
일례로, 상기 화학식 1의 상기 헤테로고리기는 하기 화학식 7-1 또는 하기 화학식 7-2로 나타낼 수 있다.For example, the heterocyclic group of Chemical Formula 1 may be represented by Chemical Formula 7-1 or Chemical Formula 7-2.
<화학식 7-1><Formula 7-1>
<화학식 7-2><Formula 7-2>
상기 화학식 7-1 및 7-2 각각에서, R7, R8, R9 및 R10은 각각 독립적으로 탄소수 1 내지 6의 알킬기를 나타낸다.In each of Chemical Formulas 7-1 and 7-2, R 7 , R 8 , R 9 and R 10 each independently represent an alkyl group having 1 to 6 carbon atoms.
일 실시예에서, 상기 화학식 4로 나타내는 화합물은 하기 화학식 8로 나타내는 화합물을 포함할 수 있다.In one embodiment, the compound represented by Formula 4 may include a compound represented by the following formula (8).
<화학식 8><Formula 8>
상기 화학식 8에서, Ar2는 하기 표 1에서 선택된 어느 하나를 나타낼 수 있다.In Formula 8, Ar 2 may represent any one selected from Table 1 below.
표 1
Table 1
| 치환기의 종류 | |
| 1 |  |
| 2 |  |
| 3 |  |
| 4 |  |
| 5 |  |
| 6 |  |
| 7 |  |
| 8 |  |
| Type of substituent | |
| One | |
| 2 | |
| 3 | |
| 4 | |
| 5 | |
| 6 | |
| 7 | |
| 8 | |
또한, 상기 화학식 8에서, Ar3 및 Ar4는 각각 독립적으로 수소 또는 하기 표 2에서 선택된 어느 하나를 나타낼 수 있다.In addition, in Formula 8, Ar 3 and Ar 4 may each independently represent hydrogen or any one selected from Table 2 below.
표 2
TABLE 2
| 치환기의 종류 | |
| 1 |  |
| 2 |  |
| 3 |  |
| 4 |  |
| 5 |  |
| 6 |  |
| Type of substituent | |
| One | |
| 2 | |
| 3 | |
| 4 | |
| 5 | |
| 6 | |
또한, 상기 화학식 8에서, La는 단일 결합 또는 하기 표 3에서 선택된 어느 하나를 나타낼 수 있다.In addition, in Formula 8, L a may represent a single bond or any one selected from Table 3 below.
표 3
TABLE 3
| 치환기의 종류 | |
| 1 |  |
| 2 |  |
| 3 |  |
| 4 |  |
| 5 |  |
| 6 |  |
| Type of substituent | |
| One | |
| 2 | |
| 3 | |
| 4 | |
| 5 | |
| 6 | |
또한, 상기 화학식 8의 R1 및 R2는 각각 독립적으로 탄소수 1 내지 6의 알킬기 또는 페닐기를 나타낼 수 있다.In addition, 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.
예를 들어, 표 1의 5번 치환기의 경우, 구체적으로는 하기 화학식 1-1a 또는 하기 화학식 1-1b로 나타낼 수 있다.For example, in the case of 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.
<화학식 1-1a><Formula 1-1a>
<화학식 1-1b><Formula 1-1b>
표 1의 6번 치환기는 하기 화학식 1-2a 또는 하기 화학식 1-2b로 나타낼 수 있다.Substituent No. 6 in Table 1 may be represented by the following Formula 1-2a or the following Formula 1-2b.
<화학식 1-2a><Formula 1-2a>
<화학식 1-2b><Formula 1-2b>
또한, 표 2의 5번 치환기는 하기 화학식 2-1a 또는 하기 화학식 2-1b로 나타낼 수 있다.In addition, substituent 5 of Table 2 may be represented by the following formula 2-1a or 2-2b.
<화학식 2-1a><Formula 2-1a>
<화학식 2-1b><Formula 2-1b>
표 2의 6번 치환기는 하기 화학식 2-2a 또는 하기 화학식 2-2b로 나타낼 수 있다.Substituent No. 6 in Table 2 may be represented by the following Formula 2-2a or the following Formula 2-2b.
<화학식 2-2a><Formula 2-2a>
<화학식 2-2b><Formula 2-2b>
표 1 내지 표 3의 각 치환기들은 표시된 범위에서 다양한 결합 위치를 가질 수 있으며, 중복되는 설명은 생략한다.Each substituent in Tables 1 to 3 may have various binding positions in the indicated ranges, and overlapping descriptions are omitted.
일 실시예에서, 화학식 1로 나타내는 화합물은 하기 구조 1 내지 구조 36으로 나타내는 화합물들 중에서 선택된 어느 하나일 수 있다.In one embodiment, the compound represented by Formula 1 may be any one selected from compounds represented by Structures 1 to 36 below.
<구조 1><Structure 1>
<구조 2><Structure 2>
<구조 3><Structure 3>
<구조 4><Structure 4>
<구조 5><Structure 5>
<구조 6><Structure 6>
<구조 7><Structure 7>
<구조 8> <Structure 8>
<구조 9><Structure 9>
<구조 10><Structure 10>
<구조 11><Structure 11>
<구조 12><Structure 12>
<구조 13><Structure 13>
<구조 14><Structure 14>
<구조 15><Structure 15>
<구조 16><Structure 16>
<구조 17><Structure 17>
<구조 18><Structure 18>
<구조 19><Structure 19>
<구조 20><Structure 20>
<구조 21><Structure 21>
<구조 22><Structure 22>
<구조 23><Structure 23>
<구조 24><Structure 24>
<구조 25><Structure 25>
<구조 26><Structure 26>
<구조 27><Structure 27>
<구조 28><Structure 28>
<구조 29><Structure 29>
<구조 30><Structure 30>
<구조 31><Structure 31>
<구조 32><Structure 32>
<구조 33><Structure 33>
<구조 34><Structure 34>
<구조 35>Structure 35
<구조 36><Structure 36>
이하에서는, 첨부된 도면들을 참조하여 본 발명에 따른 신규한 화합물을 포함하는 발광 소자에 대해서 설명한다. 상기 화합물을 포함하는 발광 소자의 구조는 첨부된 도면들 및 하기의 설명에 의해 제한되는 것은 아니다.Hereinafter, a light emitting device including the novel compound according to the present invention will be described with reference to the accompanying drawings. The structure of the light emitting device including the compound is not limited by the accompanying drawings and the following description.
도 1은 본 발명의 일 실시예에 따른 발광 소자를 설명하기 위한 단면도이다.1 is a cross-sectional view illustrating a light emitting device according to an embodiment of the present invention.
도 1을 참조하면, 발광 소자(100)는 베이스 기판(10) 상에 형성된 제1 전극(20), 정공 수송성층(30), 발광층(40) 및 제2 전극(50)을 포함한다. 상기 발광 소자(100)는 유기 발광 다이오드(organic light emitting diode, OLED)일 수 있다.Referring to FIG. 1, 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).
상기 제1 전극(20)은 도전성 물질로 상기 베이스 기판(10) 상에 형성될 수 있다. 일례로, 상기 제1 전극(20)은 투명 전극일 수 있다. 이때, 상기 제1 전극(20)은 인듐 틴 옥사이드(indium tin oxide, ITO)로 형성할 수 있다. 이와 달리, 상기 제1 전극(20)은 불투명(반사) 전극일 수 있다. 이때, 상기 제1 전극(20)은 ITO/은(Ag)/ITO 구조를 가질 수 있다. 상기 제1 전극(20)은 상기 발광 소자(100)의 양극(anode)이 될 수 있다.The first electrode 20 may be formed on the base substrate 10 with a conductive material. For example, the first electrode 20 may be a transparent electrode. In this case, the first electrode 20 may be formed of indium tin oxide (ITO). Alternatively, the first electrode 20 may be an opaque (reflective) electrode. In this case, 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.
상기 정공 수송성층(30)은 상기 제1 전극(20) 상에 형성되어 상기 제1 전극(20)과 상기 발광층(40) 사이에 개재된다. 상기 정공 수송성층(30)은 정공 수송성 화합물로서 하기 화학식 1로 나타내는 화합물을 포함한다.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.
[화학식 1][Formula 1]
상기 화학식 1로 나타내는 화합물은, 본 발명에 따른 신규한 화합물로서 상기에서 설명한 것과 실질적으로 동일하다. 따라서, Ar1, Ar2, Ar3, Ar4, La, Lb, Lc, Ld 및 Le에 대한 구체적인 설명은 생략한다.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.
상기 발광층(40)을 형성하는 화합물의 종류에 따라서 상기 발광층(40)이 방출하는 광의 파장이 달라질 수 있다.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.
상기 제2 전극(50)은 도전성 물질로 상기 발광층(40) 상에 형성될 수 있다. 상기 제1 전극(20)이 투명 전극인 경우, 상기 제2 전극(50)은 불투명(반사) 전극일 수 있다. 이때, 상기 제2 전극(50)은 알루미늄 전극일 수 있다. 이와 달리, 상기 제1 전극(20)이 불투명 전극인 경우, 상기 제2 전극(50)은 투명 또는 반투명 전극일 수 있다. 이때, 상기 제2 전극(50)은 100Å 내지 150Å의 두께를 가질 수 있고, 마그네슘 및 은을 포함하는 합금일 수 있다. 상기 제2 전극(50)은 상기 발광 소자(100)의 음극(cathode)이 될 수 있다.The second electrode 50 may be formed on the light emitting layer 40 with a conductive material. When the first electrode 20 is a transparent electrode, the second electrode 50 may be an opaque (reflective) electrode. In this case, the second electrode 50 may be an aluminum electrode. In contrast, when the first electrode 20 is an opaque electrode, the second electrode 50 may be a transparent or translucent electrode. In this case, 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.
상기 발광층(40)과 상기 제2 전극(50) 사이에는 전자 수송성층으로서, 전자 수송층 및/또는 전자 주입층이 형성될 수 있다.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.
상기 발광 소자(100)의 상기 제1 및 제2 전극들(20, 50) 사이에 전류를 흘려주는 경우, 상기 제1 전극(20)으로부터 상기 발광층(40)으로 주입된 정공(hole)과 상기 제2 전극(50)으로부터 상기 발광층(40)으로 주입된 전자(electron)가 결합하여 여기자(exciton)을 형성한다. 상기 여기자가 기저 상태로 전이되는 과정에서, 특정 영역대의 파장을 갖는 광이 생성된다. 이때, 상기 여기자는 일중항(singlet) 여기자일 수 있으며, 또한 삼중항(triplet) 여기자일 수 있다. 이에 따라, 상기 발광 소자(100)가 외부로 광을 제공할 수 있다.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.
도면으로 도시하지 않았으나, 상기 발광 소자(100)는 상기 발광층(40)과 상기 제2 전극(50) 사이에 배치된 전자 수송층(electron transporting layer, ETL) 및 전자 주입층(electron injecting layer, EIL)을 더 포함할 수 있다. 상기 발광층(40) 상에 상기 전자 수송층 및 상기 전자 주입층이 순차적으로 적층되어 형성될 수 있다.Although not shown in the drawings, 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.
또한, 상기 발광 소자(100)는 상기 제1 전극(20)과 상기 발광층(40) 사이에 배치되는 제1 차단층(미도시) 및/또는 상기 발광층(40)과 상기 제2 전극(50) 사이에 배치되는 제2 차단층(미도시)을 더 포함할 수 있다. In addition, 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.
예를 들어, 상기 제1 차단층은 상기 정공 수송성층(30)과 상기 발광층(40) 사이에 배치되어, 상기 제2 전극(50)에서 주입된 전자가 상기 발광층(40)을 경유하여 상기 정공 수송성층(30)으로 유입되는 것을 방지하는 전자 차단층(electron blocking layer, EBL)일 수 있다. 또한, 상기 제1 차단층은 상기 발광층(40)에서 형성된 여기자가 상기 제1 전극(20)의 방향으로 확산되어 상기 여기자가 비발광 소멸하는 것을 방지하는 여기자 차단층일 수 있다. 또한, 상기 제1 차단층은 여기자 분리 차단층(exciton dissociation blocking layer, EDBL)일 수 있다. 상기 여기자 분리 차단층은, 상기 발광층(40)에서 형성된 여기자가 상기 발광층(40)과 상기 정공 수송성층(30) 사이의 계면에서 ‘여기자 분리(exciton dissociation)’ 과정을 거쳐 비발광 소멸하는 것을 방지할 수 있다. 상기 계면에서의 여기자 분리를 방지하기 위해서, 상기 제1 차단층을 형성하는 화합물은 상기 발광층(40)을 형성하는 화합물과 유사한 레벨의 HOMO 값을 갖도록 선택될 수 있다.For example, 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. In addition, 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. In addition, 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. In order to prevent exciton separation at the interface, 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.
이때, 상기 제1 차단층은 상기에서 설명한 본 발명에 따른 화합물을 포함할 수 있다.In this case, the first blocking layer may include the compound according to the present invention described above.
상기 제2 차단층은 상기 발광층(40)과 상기 제2 전극(50), 구체적으로는 상기 발광층(40)과 상기 전자 수송층 사이에 배치되어 정공이 상기 제1 전극(20)에서부터 상기 발광층(40)을 경유하여 상기 전자 수송층으로 유입되는 것을 방지하는 정공 차단층(hole blocking layer, HBL)일 수 있다. 또한, 상기 제2 차단층은 상기 발광층(40)에서 형성된 여기자가 상기 제2 전극(50)의 방향으로 확산되어 상기 여기자가 비발광 소멸하는 것을 방지하는 여기자 차단층일 수 있다.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.
상기 제1 및 제2 차단층들 각각의 두께를, 상기 발광 소자(100)의 공진 길이에 맞게 조절하면 발광 효율을 증가시킬 수 있고, 여기자가 상기 발광층(40)의 중앙부에서 형성될 수 있도록 조절될 수 있다.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.
도 2는 본 발명의 다른 실시예에 따른 발광 소자를 설명하기 위한 단면도이다.2 is a cross-sectional view illustrating a light emitting device according to another embodiment of the present invention.
도 2를 참조하면, 발광 소자(102)는 베이스 기판(10) 상에 형성된 제1 전극(20), 정공 수송성층(32), 발광층(40) 및 제2 전극(50)을 포함한다. 상기 정공 수송성층(32)을 제외하고는 도 1에서 설명한 것과 실질적으로 동일하므로 중복되는 설명은 생략한다.Referring to FIG. 2, 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.
상기 정공 수송성층(32)은 상기 화학식 1로 나타내는 화합물 및 P형 도펀트를 포함한다. 상기 정공 수송성층(32)에 포함되는 화합물은 상기에서 설명한 것과 실질적으로 동일하므로 중복되는 구체적인 설명은 생략한다.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.
상기 P형 도펀트는 P형 유기물 도펀트 및/또는 P형 무기물 도펀트를 포함할 수 있다.The P-type dopant may include a P-type organic dopant and / or a P-type inorganic dopant.
상기 P형 유기물 도펀트의 구체적인 예로서는, 하기 화학식 9 내지 13으로 나타내는 화합물들, 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) 또는 테트라시아노퀴노디메탄(Tetracyanoquinodimethane, TCNQ) 등을 포함할 수 있다. 이들은 각각 단독으로 또는 2 이상이 조합되어 이용될 수 있다.Specific examples of the P-type organic dopant 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.
[화학식 9][Formula 9]
상기 화학식 9에서, R은 시아노기, 설폰기, 설폭사이드기, 설폰아미드기, 설포네이트기, 니트로기 또는 트리플루오로메틸기를 나타낸다.In Formula 9, R represents a cyano group, a sulfone group, a sulfoxide group, a sulfonamide group, a sulfonate group, a nitro group or a trifluoromethyl group.
[화학식 10][Formula 10]
[화학식 11][Formula 11]
[화학식 12][Formula 12]
[화학식 13][Formula 13]
상기 화학식 13에서, m 및 n은 각각 독립적으로 1 내지 5의 정수를 나타내고, Y1 및 Y2는 각각 독립적으로 탄소수 6 내지 20의 아릴기 또는 탄소수 2 내지 20의 헤테로아릴기를 나타낼 수 있다. 이때, 상기 화학식 13에서, Y1 및 Y2가 나타내는 아릴기 또는 헤테로아릴기의 수소는 탄소수 1 내지 5의 알킬기, 탄소수 1 내지 5의 알콕시기 또는 하이드록시기로 치환 또는 비치환될 수 있고, 치환 또는 비치환된 Y1 및 Y2의 수소들은 각각 독립적으로 할로겐기로 치환 또는 비치환될 수 있다.In Chemical Formula 13, m and n each independently represent an integer of 1 to 5, and 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. At this time, in Formula 13, 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. Alternatively, unsubstituted hydrogen of Y 1 and Y 2 may be each independently substituted or unsubstituted with a halogen group.
예를 들어, 상기 화학식 13으로 나타내는 화합물은 하기 화학식 13a 또는 하기 화학식 13b로 나타내는 화합물을 포함할 수 있다.For example, the compound represented by Chemical Formula 13 may include a compound represented by Chemical Formula 13a or Chemical Formula 13b.
[화학식 13a][Formula 13a]
[화학식 13b][Formula 13b]
상기 P형 무기물 도펀트의 예로서는, 금속산화물 또는 금속 할라이드 등을 들 수 있다. 상기 P형 무기물 도펀트의 구체적인 예로서는, MoO3, V2O5, WO3, SnO2, ZnO, MnO2, CoO2, ReO3, TiO2, FeCl3, SbCl5 또는 MgF2 등을 들 수 있다. 이들은 각각 단독으로 또는 2 이상이 조합되어 이용될 수 있다.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.
상기 P형 도펀트는, 정공 수송성 화합물인 본 발명에 따른 신규 화합물 100 중량부에 대해서, 약 0.5 중량부 내지 약 20 중량부일 수 있다. 예를 들어, 상기 P형 도펀트는 상기 정공 수송성 화합물 100 중량부에 대하여, 약 0.5 중량부 내지 약 15 중량부이거나, 약 0.5 중량부 내지 약 5 중량부일 수 있다. 이와 달리, 상기 P형 도펀트는 상기 정공 수송성 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. 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. For example, 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. Alternatively, 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.
상기 P형 도펀트의 함량이 상기 정공 수송성 화합물 100 중량부에 대해서, 약 0.5 중량부 내지 약 20 중량부인 경우, 상기 P형 도펀트가 상기 정공 수송성 화합물의 물성을 저하시키지 않으면서도 과도한 누설 전류의 발생을 방지할 수 있다. 또한, 상기 P형 도펀트에 의해서 상기 정공 수송성층(32)과 접촉하는 상, 하부층들 각각과의 계면에서의 에너지 장벽을 감소시킬 수 있다.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.
도면으로 도시하지 않았으나, 상기 발광 소자(102)는 전자 수송층, 전자 주입층, 제1 차단층 및/또는 제2 차단층을 더 포함할 수 있다. 상기 층들 각각은 도 1의 발광 소자(100)에서 설명한 것과 실질적으로 동일하므로 구체적인 설명은 생략한다. 상기 발광 소자(102)가 상기 제1 차단층을 포함하는 경우, 상기 제1 차단층은 상기에서 설명한 본 발명에 따른 화합물을 포함할 수 있다.Although not illustrated in the drawings, 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. When the light emitting device 102 includes the first blocking layer, the first blocking layer may include the compound according to the present invention described above.
한편, 도 1에 도시된 발광 소자(100)가 중간층(interlayer, 미도시)을 더 포함할 수 있다. 상기 중간층은 도 1의 상기 제1 전극(20)과 상기 정공 수송성층(30) 사이에 배치될 수 있고, 도 2에서 설명한 P형 도펀트로 이용되는 화합물로 형성될 수 있다.Meanwhile, 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.
도 3은 본 발명의 또 다른 실시예에 따른 발광 소자를 설명하기 위한 단면도이다.3 is a cross-sectional view for describing a light emitting device according to still another embodiment of the present invention.
도 3을 참조하면, 발광 소자(104)는 베이스 기판(10) 상에 형성된 제1 전극(20), 정공 수송성층(34), 발광층(40) 및 제2 전극(50)을 포함한다. 상기 정공 수송성층(34)을 제외하고는 도 1에서 설명한 것과 실질적으로 동일하므로 중복되는 설명은 생략한다.Referring to FIG. 3, 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.
상기 정공 수송성층(34)은 상기 제1 전극(20)과 접촉하는 제1 층(33a) 및 상기 제1 층(33a)과 상기 발광층(40) 사이에 배치된 제2 층(33b)을 포함한다. 즉, 상기 정공 수송성층(34)은 2층 구조를 가질 수 있다. 또한, 상기 정공 수송성층(34)은 상기 제1 및 제2 층들(33a, 33b)을 포함하는 2층 이상의 다층 구조를 가질 수 있다.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.
상기 제1 및 제2 층들(33a, 33b)은 서로 동일한 종류의 정공 수송성 화합물을 포함할 수 있다. 상기 제1 층(33a)과 상기 제2 층(33b)에 포함되는 정공 수송성 화합물의 성분을 동일하게 함으로써, 이종 물질간의 계면에서 발생될 수 있는 물리화학적 결함을 감소시켜 발광층으로의 정공 주입을 용이하게 할 수 있다. 또 다른 측면에서, 제1층(33a)과 제2층(33b)에 동일한 호스트 물질을 사용하면, 하나의 챔버 내에서 제1층(33a)과 제2층(33b)을 연속적으로 형성할 수 있게 되므로 제작 공정이 단순해지고 제작 시간을 단축시킬 수 있는 이점이 있다. 나아가, 인접하고 있는 층간의 유리전이온도 등의 물성이 유사하게 되므로 소자의 내구성을 높일 수 있는 이점도 있다.The first and second layers 33a and 33b may include the same kind of hole transport compound. By making the components of the hole transporting compound included in the first layer 33a and the second layer 33b the same, physicochemical defects that may occur at the interface between different materials are reduced, thereby easily injecting holes into the light emitting layer. It can be done. In another aspect, when 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.
상기 제1 층(33a)은 정공 수송성 화합물로서 상기 화학식 1로 나타내는 본 발명에 따른 신규한 화합물과 P형 도펀트를 포함한다. 상기 제1 층(33a)은 두께를 제외하고는 도 2에서 설명한 상기 정공 수송성층(32)과 실질적으로 동일하다. 따라서, 중복되는 설명은 생략한다. 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.
상기 제2 층(33b)은 정공 수송성 화합물로서 상기 화학식 1로 나타내는 본 발명에 따른 신규한 화합물을 포함하되, 상기 제2 층(33b)을 구성하는 정공 수송성 화합물은 상기 제1 층(33a)을 구성하는 정공 수송성 화합물과 동일할 수 있다. 상기 제2 층(33b)도 두께를 제외하고는 도 1에서 설명한 상기 정공 수송성층(30)과 실질적으로 동일하므로, 중복되는 상세한 설명은 생략한다.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.
이와 달리, 상기 제1 및 제2 층들(33a, 33b)은 서로 다른 종류의 정공 수송성 화합물을 포함할 수 있다. 상기 제1 및 제2 층들(33a, 33b)을 구성하는 상기 정공 수송성 화합물은 상기 화학식 1로 나타내는 본 발명에 따른 신규한 화합물이되, Ar1, Ar2, Ar3, Ar4, La, Lb, Lc, Ld 및 Le는 각각 독립적으로 상이할 수 있다. 이때, 상기 제1 및 제2 층들(33a, 33b) 각각을 구성하는 화합물은, 정공을 상기 발광층(40)으로 효율적으로 전달하기 위한 HOMO값을 갖도록 선택될 수 있다.Alternatively, 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. In this case, 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.
추가적으로, 상기 제2 층(33b)이 상기 정공 수송성 화합물과 함께 P형 도펀트를 더 포함할 수 있다. 이때, 상기 제1 층(33a)과 상기 제2 층(33b)에 도핑되는 P형 도펀트의 종류는 서로 다를 수 있고, 동일한 종류가 이용되더라도 도핑량이 달라질 수 있다. 예를 들어, 상기 제1 층(33a)에 도핑된 P형 도펀트의 함량(P1)과, 상기 제2 층(33b)에 도핑된 P형 도펀트의 함량(P2)은 하기 수학식 1의 관계를 만족할 수 있다.In addition, the second layer 33b may further include a P-type dopant together with the hole transport compound. In this case, 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. For example, 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.
[수학식 1][Equation 1]
P1/P2 ≥ 1P1 / P2 ≥ 1
상기 수학식 1에서,“P1”은 상기 제1 층(33a)에서 정공 수송성 화합물 100 중량부 대비 도핑된 P형 도펀트의 함량이고, “P2”는 상기 제2 층(33b)에서 정공 수송성 화합물 100 중량부 대비 도핑된 P형 도펀트의 함량이다.In 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.
예를 들어, 상기 제1 층(33a)에 도핑된 P형 도펀트의 함량은, 정공 수송성 화합물 100 중량부를 기준으로, 0.3 내지 20중량부, 1 내지 15 중량부, 2 내지 10 중량부, 또는 4 내지 6 중량부 범위일 수 있다. 또한, 제2층(33b)에 도핑된 P형 도펀트의 함량은, 정공 수송성 화합물 100 중량부를 기준으로, 0.3 내지 20 중량부, 0.5 내지 10 중량부, 1 내지 8 중량부, 또는 2 내지 4 중량부 범위일 수 있다.For example, 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. In addition, 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.
또한, 도면으로 도시하지 않았으나, 상기 발광 소자(104)는 전자 수송층, 전자 주입층, 제1 차단층 및/또는 제2 차단층을 더 포함할 수 있다. 상기 층들 각각은 도 1의 발광 소자(100)에서 설명한 것과 실질적으로 동일하므로 구체적인 설명은 생략한다.In addition, although not shown in the drawings, 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. 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.
상기에서 설명한 상기 발광 소자들(100, 102, 104) 각각이, 상기 화학식 1로 나타내는 본 발명에 따른 신규한 화합물을 포함함으로써 상기 발광 소자들(100, 102, 104)은 발광 효율이 향상되고 수명이 길어질 수 있다.Since 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.
도 1 내지 도 3에서는, 상기 베이스 기판(10) 상에 상기 발광 소자들(100, 102, 104)이 직접적으로 형성된 것으로 도시하고 있으나, 상기 발광 소자들(100, 102, 104) 각각의 상기 제1 전극(20)과 상기 베이스 기판(10) 사이에 화소를 구동하는 구동 소자로서 박막 트랜지스터가 배치될 수 있다. 이때, 상기 제1 전극(20)이 상기 박막 트랜지스터와 연결된 화소 전극이 될 수 있다. 상기 제1 전극(20)이 화소 전극인 경우, 다수의 화소들 각각에 상기 제1 전극(20)이 서로 분리되어 배치되고 상기 베이스 기판(10)에는 상기 제1 전극(20)의 가장자리를 따라 형성되는 격벽 패턴이 형성되어 서로 인접한 화소들에 배치된 상기 제1 전극(20) 상에 적층되는 층들이 서로 격리될 수 있다. 즉, 도면으로 도시하지 않았으나 상기 발광 소자들(100, 102, 104)이 백라이트 없이 영상을 표시하는 디스플레이 장치에 이용될 수 있다.1 to 3, 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. In this case, the first electrode 20 may be a pixel electrode connected to the thin film transistor. When 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.
또한, 상기 발광 소자들(100, 102, 104)은 조명 장치로 이용될 수 있다.In addition, the light emitting devices 100, 102, and 104 may be used as lighting devices.
이와 같이, 본 발명에서 예시한 상기 발광 소자들(100, 102, 104)은 상기 디스플레이 장치 또는 상기 조명 장치와 같은 다양한 전자 장치에 이용될 수 있다.As such, 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.
이하에서는, 본 발명에 따른 구체적인 실시예들을 통해서 본 발명에 따른 신규한 화합물들을 보다 상세히 설명한다. 하기에 예시되는 실시예들은 발명의 상세한 설명을 위한 것일 뿐, 이에 의해 권리범위를 제한하려는 것은 아니다.Hereinafter, the novel compounds according to the present invention will be described in more detail through specific examples according to the present invention. The embodiments exemplified below are only for the detailed description of the present invention, and are not intended to limit the scope of the rights.
실시예 1Example 1
250 mL 3구 둥근 바닥 플라스크에 질소를 충전한 후, 화합물 A(20.55 mmol, 10 g), 화합물 B(22.60 mmol, 6.53 g), 팔라듐 아세테이트(Pd(OAc)2) (0.411 mmol, 0.09 g), 소듐 tert-부톡시드(sodium tert-butoxide) (24.66 mmol, 2.37 g), o-자일렌(o-xylene) 50 mL 및 트리-tert-부틸포스핀(50w/w% tri-tert-butylphosphine in xylene) (2.055 mmol, 0.4 mL)을 넣은 후, 130 ℃ 에서 3시간 동안 가열하였다. After charging a 250 mL three neck round bottom flask with nitrogen, Compound A (20.55 mmol, 10 g), Compound B (22.60 mmol, 6.53 g), palladium acetate (Pd (OAc) 2 ) (0.411 mmol, 0.09 g) , sodium tert - butoxide (sodium tert -butoxide) (24.66 mmol , 2.37 g), o - xylene (o -xylene) 50 mL and tri - tert - butylphosphine (50w / w% tri- tert -butylphosphine in xylene) (2.055 mmol, 0.4 mL) was added and then heated at 130 ° C. for 3 hours.
상기 반응 혼합물을 식힌 후 테트라하이드로퓨란(tetrahydrofuran, THF) 50 mL에 용해시키고 메탄올(methanol) 300 mL가 담긴 1 L 용기에 첨가하여 20분간 교반하였다. 이를 여과하여 연회색 고체인 화합물 1을 약 12 g 수득하였다(수율 84%).The reaction mixture was cooled, dissolved in 50 mL of tetrahydrofuran (THF), added to a 1 L container containing 300 mL of methanol, and stirred for 20 minutes. This was filtered to yield about 12 g of Compound 1 as a light gray solid (yield 84%).
MALDI-TOF : m/z = 694.2765 (C50H38N2Si = 694.3)MALDI-TOF: m / z = 694.2765 (C 50 H 38 N 2 Si = 694.3)
실시예 2Example 2
250 mL 3구 둥근 바닥 플라스크에 질소를 충전한 후, 화합물 A(30.82 mmol, 15 g), 화합물 C(33.90 mmol, 14 g), 팔라듐 아세테이트 (0.616 mmol, 0.13 g), 소듐 tert-부톡시드(36.99 mmol, 3.55 g), o-자일렌 75 mL 및 트리-tert-부틸포스핀 (50w/w% tri-tert-butylphosphine in xylene) (3.082 mmol, 0.4 mL)을 넣은 후, 135 ℃ 에서 5시간 동안 가열하였다. After charging a 250 mL three neck round bottom flask with nitrogen, Compound A (30.82 mmol, 15 g), Compound C (33.90 mmol, 14 g), palladium acetate (0.616 mmol, 0.13 g), sodium tert -butoxide ( 36.99 mmol, 3.55 g), o -xylene 75 mL and tri- tert -butylphosphine (50w / w% tri- tert- butylphosphine in xylene) (3.082 mmol, 0.4 mL) were added and then 5 hours at 135 ° C. Heated during.
상기 반응 혼합물을 식힌 후 테트라하이드로퓨란(THF) 75 mL에 용해시키고 메탄올 400 mL가 담긴 1 L 용기에 첨가하여 25분간 교반하였다. 이를 여과하여 회색 고체인 화합물 2를 약 20 g 수득하였다(수율 80%).The reaction mixture was cooled, dissolved in 75 mL of tetrahydrofuran (THF), added to a 1 L vessel containing 400 mL of methanol, and stirred for 25 minutes. This was filtered to give about 20 g of Compound 2 as a gray solid (yield 80%).
MALDI-TOF : m/z = 819.2518 (C60H42N2Si = 818.3)MALDI-TOF: m / z = 819.2518 (C 60 H 42 N 2 Si = 818.3)
실시예 3 Example 3
250 mL 3구 둥근 바닥 플라스크에 질소를 충전한 후, 화합물 D(19.39 mmol, 12 g), 화합물 B(31.33 mmol, 6.16 g), 팔라듐 아세테이트(0.387 mmol, 0.08 g), 소듐 tert-부톡시드(23.27 mmol, 2.23 g), o-자일렌 60 mL 및 트리-tert-부틸포스핀(50w/w% tri-tert-butylphosphine in xylene) (1.939 mmol, 0.5 mL)을 넣은 후, 130 ℃ 에서 4시간 동안 가열하였다. After charging a 250 mL three neck round bottom flask with nitrogen, Compound D (19.39 mmol, 12 g), Compound B (31.33 mmol, 6.16 g), palladium acetate (0.387 mmol, 0.08 g), sodium tert-butoxide ( 23.27 mmol, 2.23 g), o -xylene 60 mL and tri- tert -butylphosphine (50w / w% tri- tert- butylphosphine in xylene) (1.939 mmol, 0.5 mL) were added, followed by 4 hours at 130 ° C. Heated during.
상기 반응 혼합물을 식힌 후 테트라하이드로퓨란(THF) 60 mL에 용해시키고 메탄올 350 mL가 담긴 1L 용기에 첨가하여 30분간 교반하였다. 이를 여과하여 연회색 고체인 화합물 3을 약 13 g 수득하였다(수율 81%).The 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%).
MALDI-TOF : m/z = 826.2011 (C58H46N2Si2 = 826.3)MALDI-TOF: m / z = 826.2011 (C 58 H 46 N 2 Si 2 = 826.3)
실시예 4Example 4
250 mL 3구 둥근 바닥 플라스크에 질소를 충전한 후, 화합물 E(16.16 mmol, 10 g), 화합물 B(17.77 mmol, 5.14 g), 팔라듐 아세테이트(0.323 mmol, 0.07 g), 소듐 tert-부톡시드(19.39 mmol, 1.86 g), o-자일렌 50 mL 및 트리-tert-부틸포스핀(50w/w% tri-tert-butylphosphine in xylene) (1.616 mmol, 0.4 mL)을 넣은 후, 130 ℃ 에서 5시간 동안 가열하였다.After charging a 250 mL three neck round bottom flask with nitrogen, Compound E (16.16 mmol, 10 g), Compound B (17.77 mmol, 5.14 g), palladium acetate (0.323 mmol, 0.07 g), sodium tert-butoxide ( 19.39 mmol, 1.86 g), o - xylene, 50 mL and tri - tert - butylphosphine, insert the pin (50w / w% tri- tert -butylphosphine in xylene) (1.616 mmol, 0.4 mL), 5 hours at 130 ℃ Heated during.
상기 반응 혼합물을 식힌 후 테트라하이드로퓨란(THF) 50 mL에 용해시키고 메탄올 300 mL가 담긴 1L 용기에 첨가하여 20분간 교반하였다. 이를 여과하여 회색 고체인 화합물 4를 약 11 g 수득하였다(수율 82%).The 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%).
MALDI-TOF : m/z = 826.2089 (C58H46N2Si2 = 826.3)MALDI-TOF: m / z = 826.2089 (C 58 H 46 N 2 Si 2 = 826.3)
실시예 5Example 5
250 mL 3구 둥근 바닥 플라스크에 질소를 충전한 후, 화합물 F(25.30 mmol, 15 g), 화합물 B(27.83 mmol, 8.0 g), 팔라듐 아세테이트(0.506 mmol, 0.11 g), 소듐 tert-부톡시드(30.36 mmol, 2.91 g), o-자일렌 75 mL 및 트리-tert-부틸포스핀(50w/w% tri-tert-butylphosphine in xylene) (2.530 mmol, 0.6 mL)을 넣은 후, 130 ℃ 에서 7시간 동안 가열하였다. After charging a 250 mL three neck round bottom flask with nitrogen, Compound F (25.30 mmol, 15 g), Compound B (27.83 mmol, 8.0 g), palladium acetate (0.506 mmol, 0.11 g), sodium tert-butoxide ( 30.36 mmol, 2.91 g), 75 mL of o -xylene and tri- tert -butylphosphine (50w / w% tri- tert- butylphosphine in xylene) (2.530 mmol, 0.6 mL) were added, followed by 7 hours at 130 ° C. Heated during.
상기 반응 혼합물을 식힌 후 테트라하이드로퓨란(THF) 75 mL에 용해시키고 메탄올 500 mL가 담긴 1 L 용기에 첨가하여 40분간 교반하였다. 이를 여과하여 연갈색 고체인 화합물 5을 약 18 g 수득하였다(수율 88%). The reaction mixture was cooled, dissolved in 75 mL of tetrahydrofuran (THF), added to a 1 L vessel containing 500 mL of methanol, and stirred for 40 minutes. This was filtered to yield about 18 g of a light brown solid, Compound 5 (yield 88%).
MALDI-TOF : m/z = 800.2890 (C56H40N2SSi = 800.3)MALDI-TOF: m / z = 800.2890 (C 56 H 40 N 2 SSi = 800.3)
실시예 6Example 6
500 mL 3구 둥근 바닥 플라스크에 질소를 충전한 후, 화합물 G(37.70 mmol, 20 g), 화합물 H(41.47 mmol, 7.0 g), 팔라듐 아세테이트(0.754 mmol, 0.17 g), 소듐 tert-부톡시드(45.24 mmol, 4.34 g), o-자일렌 100 mL 및 트리-tert-부틸포스핀 (50w/w% tri-tert-butylphosphine in xylene)(3.770 mmol, 0.9 mL)을 넣은 후, 130 ℃ 에서 2시간 동안 가열하였다.500 mL three-necked round bottom flask was charged with nitrogen, then compound G (37.70 mmol, 20 g), compound H (41.47 mmol, 7.0 g), palladium acetate (0.754 mmol, 0.17 g), sodium tert-butoxide ( 45.24 mmol, 4.34 g), 100 mL of o -xylene and tri- tert -butylphosphine (50w / w% tri- tert- butylphosphine in xylene) (3.770 mmol, 0.9 mL) were added, followed by 2 hours at 130 ° C. Heated during.
상기 반응 혼합물을 식힌 후 테트라하이드로퓨란(THF) 100 mL에 용해시키고 메탄올 500 mL가 담긴 1 L 용기에 첨가하여 60분간 교반하였다. 이를 여과하여 아이보리색 고체인 화합물 6을 약 20 g 수득하였다(수율 86%).The 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%).
MALDI-TOF : m/z = 618.3269 (C44H34N2Si = 618.3)MALDI-TOF: m / z = 618.3269 (C 44 H 34 N 2 Si = 618.3)
실시예 7Example 7
250 mL 3구 둥근 바닥 플라스크에 질소를 충전한 후, 화합물 I(17.34 mmol, 10 g), 화합물 B(19.07 mmol, 5.51 g), 팔라듐 아세테이트(0.346 mmol, 0.07 g), 소듐 tert-부톡시드(20.80 mmol, 2.0 g), o-자일렌 50 mL 및 트리-tert-부틸포스핀(50w/w% tri-tert-butylphosphine in xylene) (1.734 mmol, 0.4 mL)을 넣은 후, 130 ℃ 에서 3시간 동안 가열하였다. After charging a 250 mL three neck round bottom flask with nitrogen, Compound I (17.34 mmol, 10 g), Compound B (19.07 mmol, 5.51 g), palladium acetate (0.346 mmol, 0.07 g), sodium tert-butoxide ( 20.80 mmol, 2.0 g), 50 mL o -xylene and tri- tert -butylphosphine (50w / w% tri- tert- butylphosphine in xylene) (1.734 mmol, 0.4 mL) were added and then 3 hours at 130 ° C. Heated during.
상기 반응 혼합물을 식힌 후 테트라하이드로퓨란(THF) 50 mL에 용해시키고 메탄올 300 mL가 담긴 1 L 용기에 첨가하여 50분간 교반하였다. 이를 여과하여 연회색 고체인 화합물 7을 약 12 g 수득하였다(수율 88%).The 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%).
MALDI-TOF : m/z = 784.2910 (C56H40N2OSi = 784.3)MALDI-TOF: m / z = 784.2910 (C 56 H 40 N 2 OSi = 784.3)
실시예 8Example 8
250 mL 3구 둥근 바닥 플라스크에 질소를 충전한 후, 화합물 J(20.63 mmol, 15 g), 화합물 C(22.69 mmol, 6.56 g), 팔라듐 아세테이트(0.412 mmol, 0.09 g), 소듐 tert-부톡시드(24.76 mmol, 2.38 g), o-자일렌 75 mL 및 트리-tert-부틸포스핀(50w/w% tri-tert-butylphosphine in xylene) (2.063 mmol, 0.5 mL)을 넣은 후, 135 ℃ 에서 5시간 동안 가열하였다. After charging a 250 mL three neck round bottom flask with nitrogen, Compound J (20.63 mmol, 15 g), Compound C (22.69 mmol, 6.56 g), palladium acetate (0.412 mmol, 0.09 g), sodium tert-butoxide ( 24.76 mmol, 2.38 g), o -xylene 75 mL and tri- tert -butylphosphine (50w / w% tri- tert -butylphosphine in xylene) (2.063 mmol, 0.5 mL) were added and 5 hours at 135 ° C. Heated during.
상기 반응 혼합물을 식힌 후 테트라하이드로퓨란(THF) 75 mL에 용해시키고 메탄올 500 mL가 담긴 1L 용기에 첨가하여 50분간 교반하였다. 이를 여과하여 연갈색 고체인 화합물 8을 약 17 g 수득하였다(수율 88%).The reaction mixture was cooled, dissolved in 75 mL of tetrahydrofuran (THF), added to a 1 L vessel containing 500 mL of methanol, and stirred for 50 minutes. This was filtered to yield about 17 g of a light brown solid, Compound 8 (yield 88%).
MALDI-TOF : m/z = 934.3744 (C69H50N2Si = 934.4)MALDI-TOF: m / z = 934.3744 (C 69 H 50 N 2 Si = 934.4)
비교예 1 내지 3Comparative Examples 1 to 3
하기 화학식 a, b 및 c의 구조를 갖는 화합물들을 상업적으로 입수 내지 제조하여, 각각 비교예 1 내지 3으로 사용하였다.Compounds having the structures of Formulas (a), (b) and (c) were obtained commercially and prepared, and used in Comparative Examples 1 to 3, respectively.
[화학식 a][Formula a]
[화학식 b][Formula b]
[화학식 c][Formula c]
발광 소자 A-1 내지 A-8의 제조Manufacturing of Light Emitting Diodes A-1 to A-8
인듐 틴 옥사이드(indium tin oxide, ITO)로 형성된 제1 전극 상에, 정공 수송성층의 호스트 물질로서 실시예 1에 따른 화합물을 1 Å/sec의 속도로 증착하고 동시에 하기 화학식 14로 나타내는 P형 도펀트(HAT-CN)를 상기 호스트 물질 100 중량부에 대해 약 3 중량부의 비율로 공증착(Co-evaporation)하여 100 Å두께의 제1 층을 형성하였다. 상기 제1 층 상에 실시예 1에 따른 화합물을 300Å의 두께로 증착하여 제2 층을 형성하였다.On the first electrode formed of indium tin oxide (ITO), a compound according to Example 1 was deposited as a host material of the hole transporting layer at a rate of 1 Å / 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.
상기 제2 층 위에 하기 화학식 15로 나타내는 mCBP와 화학식 16으로 나타내는 Ir(ppy)3을 100:9 중량비로 공증착하여 약 400Å 두께의 발광층을 형성하고, 상기 발광층 상에 다시 mCBP를 약 50Å 두께로 증착하여 차단층(blocking layer)을 형성하였다.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.
그런 다음, 상기 차단층 상에 하기 화학식 17로 나타내는 화합물과 하기 화학식 18로 나타내는 Liq를 50:50 중량비로 공증착하여 약 360 Å 두께의 전자 수송층을 형성하였다. 이어서, 상기 전자 수송층 상에 다시 하기 화학식 18로 나타내는 Liq를 이용하여 약 5 Å 두께의 전자 주입층을 형성하였다. Thereafter, the compound represented by the following Chemical Formula 17 and Liq represented by the following Chemical Formula 18 were co-deposited at a weight ratio of 50:50 on the blocking layer to form an electron transport layer having a thickness of about 360 kHz. Subsequently, an electron injection layer having a thickness of about 5 kW was formed on the electron transport layer by using Liq represented by the following Chemical Formula 18.
상기 전자 주입층 상에, 1,000Å 두께의 알루미늄 박막을 이용한 제2 전극을 형성하였다.On the electron injection layer, a second electrode using an aluminum thin film having a thickness of 1,000 Å was formed.
[화학식 14][Formula 14]
[화학식 15][Formula 15]
[화학식 16][Formula 16]
[화학식 17][Formula 17]
[화학식 18][Formula 18]
위 방법으로 본 발명의 실시예 1에 따른 화합물을 포함하는 발광 소자 A-1을 제조하였다.In the above method, the light emitting device A-1 including the compound according to Example 1 of the present invention was prepared.
또한, 제1 층 및 제2 층의 호스트 물질로서 실시예 1에 따른 화합물 대신에, 실시예 2 내지 8에 따른 화합물들 각각을 이용하여 형성하는 것을 제외하고는 상기 발광 소자 A-1을 제조하는 공정과 실질적으로 동일한 공정을 통해서 발광 소자 A-2 내지 A-8을 제조하였다.In addition, except that 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.
비교 소자 1 내지 3의 제조Preparation of Comparative Elements 1 to 3
제1 층 및 제2 층의 호스트 물질로서 실시예 1에 따른 화합물 대신에 비교예 1 내지 3에 따른 화합물을 이용하여 형성하는 것을 제외하고는 상기 발광 소자 A-1을 제조하는 공정과 실질적으로 동일한 공정을 통해서 비교 소자 1 내지 3을 제조하였다.Substantially the same as the process of manufacturing the light emitting device A-1 except that it is formed using the compound according to Comparative Examples 1 to 3 instead of the compound according to Example 1 as the host material of the first layer and the second layer. Comparative elements 1 to 3 were manufactured through the process.
발광 소자의 전력 효율 및 수명 평가 -1Evaluation of power efficiency and lifespan of light emitting device -1
상기 발광 소자 A-1 내지 A-8과, 비교 소자 1 내지 3 각각에 대해서, 질소 분위기의 글로브 박스 안에서 흡습제(Getter)가 부착된 커버 글래스 가장자리에 UV 경화용 실런트를 디스펜싱한 후, 발광 소자들 및 비교 소자들 각각과 커버 글래스를 합착하고 UV 광을 조사하여 경화시켰다. 상기와 같이 준비된 발광 소자 A-1 내지 A-8과, 비교 소자 1 내지 3 각각에 대해서, 휘도가 1,000 cd/m2일 때의 값을 기준으로 하여 전력 효율을 측정하였다. 그 결과를 표 4에 나타낸다. 또한, 수명 측정기로서 폴라로닉스 M6000S(상품명, 맥사이언스사, 한국)을 이용하여 발광 소자 A-1 내지 A-8과, 비교 소자 1 내지 3 각각의 수명을 측정하였다. 그 결과를 표 4에 나타낸다.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. For each of the light emitting elements A-1 to A-8 and Comparative Elements 1 to 3 prepared as described above, 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. In addition, using the Polaronics M6000S (trade name, McScience, Korea) as the life measuring instrument, 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.
표 4에서, 전력 효율을 측정한 결과의 단위는 lm/W이다. 또한, 표 4에서, T80은 발광 소자의 초기 휘도가 10,000 cd/m2인 경우, 상기 발광 소자의 휘도가 상기 초기 휘도 대비 80%가 되기까지 걸린 시간을 의미한다. 수명에 대한 값은 당업자에게 공지된 전환식을 기초로 하여 전환될 수 있다.In Table 4, the unit of the result of measuring the power efficiency is lm / W. In addition, 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.
표 4
Table 4
| 소자 No. | 전력효율[lm/W] | 수명(T80[hr]) |
| 발광 소자 A-1 | 27.8 | 151 |
| 발광 소자 A-2 | 29.9 | 169 |
| 발광 소자 A-3 | 24.8 | 141 |
| 발광 소자 A-4 | 25.9 | 159 |
| 발광 소자 A-5 | 19.8 | 127 |
| 발광 소자 A-6 | 22.5 | 135 |
| 발광 소자 A-7 | 17.4 | 113 |
| 발광 소자 A-8 | 20.7 | 119 |
| 비교 소자 1 | 11.3 | 66 |
| 비교 소자 2 | 14.8 | 79 |
| 비교 소자 3 | 12.9 | 71 |
| Element No. | Power Efficiency [lm / W] | Life (T 80 [hr]) |
| Light emitting element A-1 | 27.8 | 151 |
| Light emitting element A-2 | 29.9 | 169 |
| Light emitting element A-3 | 24.8 | 141 |
| Light emitting element A-4 | 25.9 | 159 |
| Light emitting element A-5 | 19.8 | 127 |
| Light emitting element A-6 | 22.5 | 135 |
| Light emitting element A-7 | 17.4 | 113 |
| Light emitting element A-8 | 20.7 | 119 |
| Comparative element 1 | 11.3 | 66 |
| Comparative element 2 | 14.8 | 79 |
| Comparative element 3 | 12.9 | 71 |
표 4를 참조하면, 발광 소자 A-1 내지 A-8의 전력 효율은 각각 27.8 lm/W, 29.9 lm/W, 24.8 lm/W, 25.9 lm/W, 19.8 lm/W, 22.5 lm/W, 17.4 lm/W 및 20.7 lm/W임을 알 수 있다. 즉, 본 발명의 실시예 1 내지 8에 따른 화합물들을 이용하여 제조된 발광 소자의 전력 효율은 적어도 약 17.4 lm/W임을 알 수 있다. 반면, 비교 소자 1 내지 3의 전력 효율은 각각 11.3 lm/W, 14.8 lm/W 및 12.9 lm/W이므로, 본 발명의 실시예 1 내지 8에 따른 화합물들을 이용하여 제조된 발광 소자의 전력 효율이 비교 소자 1 내지 3의 전력 효율보다 좋은 것을 알 수 있다. 특히, 비교 소자 1 내지 3 중에서 최대 전력 효율을 갖는 비교 소자 2와, 발광 소자 A-1 내지 A-8 중에서 최소 전력 효율을 갖는 발광 소자 A-7을 비교할 때, 본 발명에 따른 화합물을 이용한 발광 소자의 전력 효율이 적어도 약 17% 증가된 것을 알 수 있다.Referring to Table 4, 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. On the other hand, 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. In particular, when comparing 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, 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 17%.
또한, 발광 소자 A-1 내지 A-8의 수명은 각각 151시간, 169시간, 141시간, 159시간, 127시간, 135시간, 113시간 및 119시간인 반면, 비교 소자 1 내지 3 각각의 수명은 66시간, 79시간 및 71시간임을 알 수 있다. 비교 소자 2의 수명과 발광 소자 A-7의 수명을 비교할 때, 본 발명에 따른 화합물을 이용한 발광 소자의 수명은 적어도 약 43% 길어짐을 알 수 있다.In addition, 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.
발광 소자 B-1 내지 B-8의 제조Manufacturing of Light Emitting Diodes B-1 to B-8
인듐 틴 옥사이드(ITO)로 형성된 제1 전극 상에, 상기 화학식 14로 나타내는 HAT-CN을 약 100 Å의 두께로 증착하여 제1 층을 형성하고, 상기 제1 층 상에 NPB(N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4'-diamine)를 약 300 Å 두께로 증착하여 제2 층을 형성하였다.On the first electrode formed of indium tin oxide (ITO), 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. -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.
상기 제2 층 상에 실시예 1에 따른 화합물로 약 100 Å두께의 제1 차단층을 형성하고, 상기 제1 차단층 상에 상기 화학식 15로 나타내는 mCBP와 상기 화학식 16으로 나타내는 Ir(ppy)3를 100:9 중량비로 공증착하여 약 400 Å 두께의 발광층을 형성하였다. 상기 발광층 상에 다시 mCBP를 약 50 Å 두께로 증착하여 제2 차단층을 형성하였다.A first blocking layer having a thickness of about 100 μm 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. Was co-deposited at a weight ratio of 100: 9 to form a light emitting layer having a thickness of about 400 mW. MCBP was deposited on the emission layer again to a thickness of about 50 mW to form a second blocking layer.
이어서, 상기 제2 차단층 상에 상기 화학식 17로 나타내는 화합물과 상기 화학식 18로 나타내는 Liq를 50:50 중량비로 공증착하여 약 360 Å 두께의 전자 수송층을 형성하였다. 이어서, 상기 전자 수송층 상에 다시 Liq를 약 5 Å 두께로 증착하여 전자 주입층을 형성하였다.Subsequently, 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.
상기 전자 주입층 상에, 1,000Å 두께의 알루미늄 박막을 이용한 제2 전극을 형성하여, 본 발명의 실시예 1에 따른 화합물을 포함하는 발광 소자 B-1을 제조하였다.On the electron injection layer, a second electrode using an aluminum thin film having a thickness of 1,000 Å was formed to manufacture light emitting device B-1 including the compound according to Example 1 of the present invention.
상기 제1 차단층을, 본 발명의 실시예 1에 따른 화합물 대신에, 본 발명의 실시예 2 내지 8에 따른 화합물들 각각을 이용하여 제조하는 것을 제외하고는 상기 발광 소자 B-1을 제조하는 공정과 실질적으로 동일한 공정을 통해서 발광 소자 B-2 내지 B-8을 제조하였다.Except for manufacturing 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.
비교 소자 4 내지 6의 제조Preparation of Comparative Elements 4-6
상기 발광 소자 B-1을 제조하는 공정에서 제1 차단층을 상기 화학식 a로 나타내는 비교예 1에 따른 화합물을 이용하여 제조한 것을 제외하고는 실질적으로 동일한 공정으로 비교 소자 4를 제조하였다.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.
또한, 상기 발광 소자 B-1을 제조하는 공정에서 제1 차단층을 상기 화학식 b 및 상기 화학식 c로 나타내는 비교예 2 및 3에 따른 화합물을 이용하여 제조한 것을 제외하고는 실질적으로 동일한 공정으로 비교 소자 5 및 6을 각각 제조하였다.In addition, except that the first blocking layer in the step of manufacturing the light emitting device B-1 using a compound according to Comparative Examples 2 and 3 represented by the formula b and the formula c compared in substantially the same process Devices 5 and 6 were prepared, respectively.
발광 소자의 전력 효율 및 수명 평가 -2Evaluation of power efficiency and lifespan of light emitting device -2
상기와 같이 준비된 발광 소자 B-1 내지 B-8과 비교 소자 4 내지 6 각각에 대해서, 상기 발광 소자 A-1 내지 A-8에 대한 전력 효율 측정 실험과 실질적으로 동일한 방법으로 휘도가 1,000 cd/m2일 때의 값을 기준으로 하여 전력 효율을 측정하였다.For each of the light emitting elements B-1 to B-8 and the comparative elements 4 to 6 prepared as described above, 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 .
또한, 상기에서 발광 소자 A-1 내지 A-8에 대한 수명 평가 실험과 실질적으로 동일한 방법으로, 발광 소자 B-1 내지 B-8 및 비교 소자 4 내지 6 각각의 수명을 측정하였다.In addition, 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.
상기 발광 소자 B-1 내지 B-8 및 비교 소자 4 내지 6 각각의 전력 효율 및 수명의 결과를 표 5에 나타낸다. 표 5에서, 전력 효율을 측정한 결과의 단위는 lm/W이다. 또한, 표 5에서, T80은 발광 소자의 초기 휘도가 10,000cd/m2인 경우, 상기 발광 소자의 휘도가 상기 초기 휘도 대비 80%가 되기까지 걸린 시간을 의미한다. 수명에 대한 값은 당업자에게 공지된 전환식을 기초로 하여 전환될 수 있다.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. In Table 5, the unit of the result of measuring the power efficiency is lm / W. In addition, in Table 5, 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.
표 5
Table 5
| 소자 No. | 전력효율[lm/W] | 수명(T80[hr]) |
| 발광 소자 B-1 | 25.9 | 114 |
| 발광 소자 B-2 | 27.4 | 137 |
| 발광 소자 B-3 | 28.6 | 129 |
| 발광 소자 B-4 | 26.3 | 116 |
| 발광 소자 B-5 | 35.7 | 148 |
| 발광 소자 B-6 | 33.8 | 159 |
| 발광 소자 B-7 | 34.5 | 163 |
| 발광 소자 B-8 | 29.2 | 141 |
| 비교 소자 4 | 12.7 | 73 |
| 비교 소자 5 | 15.9 | 83 |
| 비교 소자 6 | 14.2 | 76 |
| Element No. | Power Efficiency [lm / W] | Life (T 80 [hr]) |
| Light emitting element B-1 | 25.9 | 114 |
| Light emitting element B-2 | 27.4 | 137 |
| Light emitting element B-3 | 28.6 | 129 |
| Light emitting element B-4 | 26.3 | 116 |
| Light emitting element B-5 | 35.7 | 148 |
| Light emitting element B-6 | 33.8 | 159 |
| Light emitting element B-7 | 34.5 | 163 |
| Light emitting element B-8 | 29.2 | 141 |
| Comparative element 4 | 12.7 | 73 |
| Comparative element 5 | 15.9 | 83 |
| Comparative element 6 | 14.2 | 76 |
표 5를 참조하면, 발광 소자 B-1 내지 B-8의 전력 효율은 각각 25.9 lm/W, 27.4 lm/W, 28.6 lm/W, 26.3 lm/W, 35.7 lm/W, 33.8 lm/W, 34.5 lm/W 및 29.2 lm/W임을 알 수 있다. 반면, 비교 소자 4 내지 6의 전력 효율은 각각 12.7 lm/W, 15.9 lm/W 및 14.2 lm/W임을 알 수 있다. 즉, 본 발명의 실시예 1 내지 8에 따른 화합물들을 이용하여 제조된 발광 소자의 전력 효율이 비교 소자 4 내지 6의 전력 효율보다 좋은 것을 알 수 있다. 특히, 비교 소자 4 내지 6 중에 최대 전력 효율을 갖는 비교 소자 5와, 발광 소자 B-1 내지 B-8 중에서 최소 전력 효율을 갖는 발광 소자 B-1을 비교할 때, 본 발명에 따른 화합물을 이용한 발광 소자의 전력 효율이 적어도 약 62% 증가된 것을 알 수 있다.Referring to Table 5, 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. 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 better than that of the comparative devices 4 to 6. In particular, when comparing 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%.
또한, 발광 소자 B-1 내지 B-8의 수명은 각각 114시간, 137시간, 129시간, 116시간, 148시간, 159시간, 163시간 및 141시간인 반면, 비교 소자 4 내지 6의 수명은 73시간, 83시간 및 76시간임을 알 수 있다. 비교 소자 5의 수명과 발광 소자 B-1의 수명을 비교할 때, 본 발명에 따른 화합물을 이용한 발광 소자의 수명이 적어도 37% 길어짐을 알 수 있다.In addition, 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.
발광 소자 C-1 내지 C-8의 제조Manufacturing of Light Emitting Diodes C-1 to C-8
인듐 틴 옥사이드(ITO)로 형성된 제1 전극 상에, 정공 수송성층의 호스트 물질로서 NPB를 1 Å/sec의 속도로 증착하고 동시에 상기 화학식 14로 나타내는 P형 도펀트(HAT-CN)를 상기 호스트 물질 100 중량부에 대해 약 3 중량부의 비율로 공증착하여 100 Å 두께의 제1 층을 형성하였다. 상기 제1 층 상에 NPB를 300 Å의 두께로 증착하여 제2 층을 형성하였다. 상기 제2 층 상에 실시예 1에 따른 화합물로 약 100 Å 두께의 제1 차단층을 형성하고, 상기 제1 차단층 상에 상기 화학식 15로 나타내는 mCBP와 상기 화학식 16으로 나타내는 Ir(ppy)3를 100:9 중량비로 공증착하여 약 400Å 두께의 발광층을 형성하였다. 상기 발광층 상에 다시 mCBP를 약 50 Å 두께로 증착하여 제2 차단층을 형성하였다.On the first electrode formed of indium tin oxide (ITO), NPB is deposited as a host material of the hole transporting layer at a rate of 1 Å / sec, and at the same time, the P-type dopant (HAT-CN) represented by Formula 14 is formed on the host material. Co-deposited at a ratio of about 3 parts by weight to 100 parts by weight to form a 100 mm thick first layer. 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 μs 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. Was co-deposited at a weight ratio of 100: 9 to form a light emitting layer having a thickness of about 400 GPa. MCBP was deposited on the emission layer again to a thickness of about 50 mW to form a second blocking layer.
이어서, 상기 제2 차단층 상에 상기 화학식 17로 나타내는 화합물과 상기 화학식 18로 나타내는 Liq를 50:50 중량비로 공증착하여 약 360 Å 두께의 전자 수송층을 형성하였다. 이어서, 상기 전자 수송층 상에 다시 Liq를 이용하여 약 5 Å 두께의 전자 주입층을 형성하였다.Subsequently, 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.
상기 전자 주입층 상에, 1,000Å 두께의 알루미늄 박막을 이용한 제2 전극을 형성하여, 본 발명의 실시예 1에 따른 화합물을 포함하는 발광 소자 C-1을 제조하였다.On the electron injection layer, a second electrode using an aluminum thin film having a thickness of 1,000 Å was formed to manufacture a light emitting device C-1 including the compound according to Example 1 of the present invention.
상기 제1 차단층을, 실시예 1에 따른 화합물 대신에, 본 발명의 실시예 2 내지 8에 따른 화합물들 각각을 이용하여 제조하는 것을 제외하고는, 상기 발광 소자 C-1을 제조하는 공정과 실질적으로 동일한 공정을 통해서 발광 소자 C-2 내지 C-8를 제조하였다.A process of manufacturing the light emitting device C-1, except that the first blocking layer, instead of the compound according to Example 1, using each of the compounds according to Examples 2 to 8 of the present invention and Light emitting devices C-2 to C-8 were manufactured through substantially the same process.
비교 소자 7 내지 9의 제조Preparation of Comparative Elements 7-9
상기 발광 소자 C-1을 제조하는 공정에서 제1 차단층을 상기 화학식 a로 나타내는 비교예 1에 따른 화합물을 이용하여 제조한 것을 제외하고는 실질적으로 동일한 공정으로 비교 소자 7을 제조하였다.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.
또한, 상기 발광 소자 C-1을 제조하는 공정에서 제1 차단층을 상기 화학식 b 및 상기 화학식 c로 나타내는 비교예 2 및 3에 따른 화합물을 이용하여 제조한 것을 제외하고는 실질적으로 동일한 공정으로 비교 소자 8 및 9를 각각 제조하였다.In addition, in the process of manufacturing the light emitting device C-1, 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.
발광 소자의 전력 효율 및 수명 평가 -3Evaluation of Power Efficiency and Lifespan of Light-Emitting Element -3
상기와 같이 준비된 발광 소자 C-1 내지 C-8과 비교 소자 7 내지 9 각각에 대해서, 상기 발광 소자 A-1 내지 A-10에 대한 전력 효율 측정 실험과 실질적으로 동일한 방법으로 휘도가 1,000 cd/m2일 때의 값을 기준으로 하여 전력 효율을 측정하였다.For each of the light emitting devices C-1 to C-8 and the comparative devices 7 to 9 prepared as described above, 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 .
또한, 상기에서 발광 소자 A-1 내지 A-10에 대한 수명 평가 실험과 실질적으로 동일한 방법으로 발광 소자 C-1 내지 C-8과 비교 소자 7 내지 9 각각의 수명을 측정하였다.In addition, the lifespan of each of the light emitting devices C-1 to C-8 and the comparative devices 7 to 9 was measured in the same manner as the life evaluation experiments for the light emitting devices A-1 to A-10.
상기 발광 소자 C-1 내지 C-8 및 비교 소자 7 내지 9 각각의 전력 효율 및 수명의 결과를 표 6에 나타낸다. 표 6에서, 전력 효율을 측정한 결과의 단위는 lm/W이다. 또한, 표 6에서, T80은 발광 소자의 초기 휘도가 10,000cd/m2인 경우, 상기 발광 소자의 휘도가 상기 초기 휘도 대비 80%가 되기까지 걸린 시간을 의미한다. 수명에 대한 값은 당업자에게 공지된 전환식을 기초로 하여 전환될 수 있다.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. In Table 6, the unit of the result of measuring the power efficiency is lm / W. In addition, in Table 6, 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.
표 6
Table 6
| 소자 No. | 전력효율[lm/W] | 수명(T80[hr]) |
| 발광 소자 C-1 | 26.8 | 119 |
| 발광 소자 C-2 | 28.9 | 141 |
| 발광 소자 C-3 | 29.1 | 137 |
| 발광 소자 C-4 | 27.8 | 122 |
| 발광 소자 C-5 | 36.8 | 157 |
| 발광 소자 C-6 | 34.7 | 165 |
| 발광 소자 C-7 | 35.9 | 179 |
| 발광 소자 C-8 | 30.7 | 150 |
| 비교 소자 7 | 13.8 | 83 |
| 비교 소자 8 | 16.3 | 91 |
| 비교 소자 9 | 15.1 | 85 |
| Element No. | Power Efficiency [lm / W] | Life (T 80 [hr]) |
| Light emitting element C-1 | 26.8 | 119 |
| Light emitting element C-2 | 28.9 | 141 |
| Light emitting element c-3 | 29.1 | 137 |
| Light emitting element C-4 | 27.8 | 122 |
| Light emitting element C-5 | 36.8 | 157 |
| Light emitting element C-6 | 34.7 | 165 |
| Light emitting element C-7 | 35.9 | 179 |
| Light emitting element C-8 | 30.7 | 150 |
| Comparative element 7 | 13.8 | 83 |
| Comparative element 8 | 16.3 | 91 |
| Comparative element 9 | 15.1 | 85 |
표 6을 참조하면, 발광 소자 C-1 내지 C-8 각각의 전력 효율은 26.8 lm/W, 28.9 lm/W, 29.1 lm/W, 27.8 lm/W, 36.8 lm/W, 34.7 lm/W, 35.9 lm/W 및 30.7 lm/W임을 알 수 있다. 반면, 비교 소자 7 내지 9 각각의 전력 효율은 13.8 lm/W, 16.3 lm/W 및 15.1 lm/W임을 알 수 있다. 즉, 본 발명의 실시예 1 내지 8에 따른 화합물들을 이용하여 제조된 발광 소자의 전력 효율이 비교 소자 7 내지 9의 전력 효율보다 좋은 것을 알 수 있다. 특히, 비교 소자 7 내지 9 중에 최대 전력 효율을 갖는 비교 소자 8과, 발광 소자 C-1 내지 C-8 중에서 최소 전력 효율을 갖는 발광 소자 C-1을 비교할 때, 본 발명에 따른 화합물을 이용한 발광 소자의 전력 효율이 적어도 약 64% 증가된 것을 알 수 있다.Referring to Table 6, 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. On the other hand, it can be seen that 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. 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 better than that of the comparative devices 7 to 9. In particular, when comparing 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%.
또한, 발광 소자 C-1 내지 C-8의 수명은 각각 119시간, 141시간, 137시간, 122시간, 157시간, 165시간, 179시간 및 150시간인 반면, 비교 소자 7 내지 9의 수명은 83시간, 91시간 및 85시간임을 알 수 있다. 비교 소자 8과 발광 소자 C-1의 수명을 비교할 때, 본 발명에 따른 화합물을 이용한 발광 소자의 수명이 적어도 30% 길어짐을 알 수 있다.In addition, 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.
Claims (10)
- 하기 화학식 1로 나타내는 화합물;A compound represented by Formula 1;<화학식 1><Formula 1>
상기 화학식 1에서,In Chemical Formula 1,Ar1, Ar2, Ar3 및 Ar4는 각각 독립적으로 수소, 탄소수 1 내지 30을 갖는 알킬기, 탄소수 6 내지 60을 갖는 아릴기, 탄소수 3 내지 60을 갖는 시클로알킬기, 탄소수 2 내지 60을 갖는 헤테로고리기 또는 하기 화학식 2를 나타내되, Ar1, Ar2, Ar3 및 Ar4 중 적어도 하나는 하기 화학식 2를 나타내고,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,<화학식 2><Formula 2>
La, Lb, Lc, Ld 및 Le는 각각 독립적으로 *-L1-L2-L3-*을 나타내고,L a , L b , L c , L d and L e each independently represent * -L 1 -L 2 -L 3- *,L1, L2 및 L3은 각각 독립적으로 단일 결합, -O-, -S-, 탄소수 6 내지 60을 갖는 아릴렌기, 탄소수 2 내지 60을 갖는 헤테로아릴렌기, 탄소수 3 내지 60을 갖는 시클로알킬렌기, 탄소수 2 내지 60을 갖는 헤테로시클로알킬렌기 또는 하기 화학식 3을 나타내며,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,<화학식 3><Formula 3>
상기 화학식 2 및 3에서, R1, R2, R3 및 R4는 각각 독립적으로 수소, 탄소수 1 내지 10을 갖는 알킬기, 탄소수 3 내지 60을 갖는 시클로알킬기 또는 탄소수 6 내지 60을 갖는 아릴기를 나타내고,In Formulas 2 and 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. ,상기 화학식 1의 수소들 중 하나 이상은 각각 독립적으로 탄소수 1 내지 6을 갖는 알킬기, 탄소수 2 내지 6을 갖는 알케닐기, 탄소수 1 내지 6을 갖는 알콕시기, 탄소수 6 내지 20을 갖는 아릴기, 탄소수 2 내지 20을 갖는 헤테로아릴기, 탄소수 6 내지 20을 갖는 아릴옥시기, 탄소수 6 내지 20을 갖는 아릴티오기, 탄소수 1 내지 6을 갖는 알콕시카르보닐기, 할로겐기, 시아노기, 나이트로기, 하이드록시기 및 카르복시기로 이루어진 군으로부터 선택된 어느 하나로 치환 또는 비치환된다.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. - 제 1 항에 있어서, 상기 화학식 1로 나타내는 화합물은 하기 화학식 4로 나타내는 것을 특징으로 하는 화합물;The compound of claim 1, wherein the compound represented by Chemical Formula 1 is represented by the following Chemical Formula 4;<화학식 4><Formula 4>
상기 화학식 4에서,In Chemical Formula 4,Ar2, Ar3 및 Ar4는 각각 독립적으로 수소, 탄소수 1 내지 30을 갖는 알킬기, 탄소수 6 내지 30을 갖는 아릴기, 탄소수 3 내지 30을 갖는 시클로알킬기, 탄소수 2 내지 30을 갖는 헤테로고리기 또는 하기 화학식 5를 나타내고,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,<화학식 5><Formula 5>
La, Lb, Lc, Ld 및 Le는 각각 독립적으로 *-L1-L2-L3-*을 나타내고,L a , L b , L c , L d and L e each independently represent * -L 1 -L 2 -L 3- *,L1, L2 및 L3은 각각 독립적으로 단일 결합, -O-, -S-, 탄소수 6 내지 30의 아릴렌기, 탄소수 2 내지 30을 갖는 헤테로아릴렌기, 탄소수 3 내지 30의 시클로알킬렌기, 탄소수 2 내지 30을 갖는 헤테로시클로알킬렌기 또는 하기 화학식 6을 나타내며,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)<화학식 6><Formula 6>
R1, R2, R3, R4, R5 및 R6은 각각 독립적으로 수소, 탄소수 1 내지 10을 갖는 알킬기, 탄소수 3 내지 30을 갖는 시클로알킬기, 탄소수 6 내지 30을 갖는 아릴기를 나타내고,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,상기 화학식 4의 수소들 중 하나 이상은 각각 독립적으로 탄소수 1 내지 6을 갖는 알킬기, 탄소수 2 내지 6을 갖는 알케닐기, 탄소수 1 내지 6을 갖는 알콕시기, 탄소수 6 내지 20을 갖는 아릴기, 탄소수 2 내지 20을 갖는 헤테로아릴기, 탄소수 6 내지 20을 갖는 아릴옥시기, 탄소수 6 내지 20을 갖는 아릴티오기, 탄소수 1 내지 6을 갖는 알콕시카르보닐기, 할로겐기, 시아노기, 나이트로기, 하이드록시기 및 카르복시기로 이루어진 군으로부터 선택된 어느 하나로 치환 또는 비치환된다.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. - 제 1 항에 있어서, 상기 헤테로고리기는The method of claim 1, wherein the heterocyclic group하기 화학식 7-1 또는 하기 화학식 7-2로 나타내는 치환기를 포함하는 것을 특징으로 하는 화합물;A compound comprising a substituent represented by the following Chemical Formula 7-1 or the following Chemical Formula 7-2;<화학식 7-1><Formula 7-1>
<화학식 7-2><Formula 7-2>
상기 화학식 7-1 및 7-2 각각에서,In each of Formulas 7-1 and 7-2,R7, R8, R9 및 R10은 각각 독립적으로 탄소수 1 내지 6의 알킬기를 나타낸다.R 7 , R 8 , R 9 and R 10 each independently represent an alkyl group having 1 to 6 carbon atoms. - 제 2 항에 있어서, 상기 화학식 4로 나타내는 화합물은 하기 화학식 8로 나타내는 것을 특징으로 하는 화합물;The compound according to claim 2, wherein the compound represented by Chemical Formula 4 is represented by the following Chemical Formula 8;<화학식 8><Formula 8>
상기 화학식 8에서, Ar2는 하기 치환기 1-1 내지 1-8 중에서 선택된 어느 하나를 나타내고,In Formula 8, Ar 2 represents any one selected from the following substituents 1-1 to 1-8,<치환기 1-1><Substituent 1-1>
<치환기 1-2><Substitute 1-2>
<치환기 1-3><Substitution 1-3>
<치환기 1-4><Substituent 1-4>
<치환기 1-5><Substituent 1-5>
<치환기 1-6><Substituent 1-6>
<치환기 1-7><Substituent 1-7>
<치환기 1-8><Substituent 1-8>
Ar3 및 Ar4는 각각 독립적으로 수소 또는 하기 치환기 2-1 내지 2-6 중에서 선택된 어느 하나를 나타내고,Ar 3 and Ar 4 each independently represent hydrogen or any one selected from the following substituents 2-1 to 2-6,<치환기 2-1><Substituent 2-1>
<치환기 2-2><Substituent 2-2>
<치환기 2-3><Substitute 2-3>
<치환기 2-4><Substituent 2-4>
<치환기 2-5><Substituent 2-5>
<치환기 2-6><Substituent 2-6>
La는 단일 결합 또는 하기 치환기 3-1 내지 3-6 중에서 선택된 어느 하나를 나타내고,L a represents a single bond or any one selected from the following substituents 3-1 to 3-6,<치환기 3-1><Substituent 3-1>
<치환기 3-2><Substituent 3-2>
<치환기 3-3><Substituent 3-3>
<치환기 3-4><Substituent 3-4>
<치환기 3-5><Substitution 3-5>
<치환기 3-6><Substituent 3-6>
R1 및 R2는 각각 독립적으로 탄소수 1 내지 6의 알킬기 또는 페닐기를 나타낸다.R 1 and R 2 each independently represent an alkyl group having 1 to 6 carbon atoms or a phenyl group. - 제 1 항에 있어서, 상기 화학식 1로 나타내는 화합물은According to claim 1, wherein the compound represented by Formula 1하기 구조 1 내지 구조 34로 나타내는 화합물들 중에서 선택된 것을 특징으로 하는 화합물.A compound selected from compounds represented by structures 1 to 34 below.<구조 1><Structure 1>
<구조 2><Structure 2>
<구조 3><Structure 3>
<구조 4><Structure 4>
<구조 5><Structure 5>
<구조 6><Structure 6>
<구조 7><Structure 7>
<구조 8> <Structure 8>
<구조 9><Structure 9>
<구조 10><Structure 10>
<구조 11><Structure 11>
<구조 12><Structure 12>
<구조 13><Structure 13>
<구조 14><Structure 14>
<구조 15><Structure 15>
<구조 16><Structure 16>
<구조 17><Structure 17>
<구조 18><Structure 18>
<구조 19><Structure 19>
<구조 20><Structure 20>
<구조 21><Structure 21>
<구조 22><Structure 22>
<구조 23><Structure 23>
<구조 24><Structure 24>
<구조 25><Structure 25>
<구조 26><Structure 26>
<구조 27><Structure 27>
<구조 28><Structure 28>
<구조 29><Structure 29>
<구조 30><Structure 30>
<구조 31><Structure 31>
<구조 32><Structure 32>
<구조 33><Structure 33>
<구조 34><Structure 34>
<구조 35>Structure 35
<구조 36><Structure 36>
- 제1 전극;A first electrode;제2 전극;Second electrode;제1 전극과 제2 전극 사이에 배치된 발광층; 및A light emitting layer disposed between the first electrode and the second electrode; And제1 전극과 발광층 사이에 배치되고, 제1항 내지 제5항 중 어느 한 항에 따른 화합물을 포함하는 정공 수송성층을 포함하는 발광 소자.A light emitting device comprising a hole transport layer, disposed between the first electrode and the light emitting layer, comprising the compound according to any one of claims 1 to 5.
- 제 6 항에 있어서, 상기 정공 수송성층은 P형 도펀트를 더 포함하는 것을 특징으로 하는 발광 소자.The light emitting device of claim 6, wherein the hole transport layer further comprises a P-type dopant.
- 제 6 항에 있어서, 상기 정공 수송성층은The method of claim 6, wherein the hole transport layer상기 화합물 및 P형 도펀트를 포함하는 제1 층; 및A first layer comprising the compound and a P-type dopant; And상기 화합물을 포함하는 제2 층을 포함하는 것을 특징으로 하는 발광 소자.A light emitting device comprising a second layer comprising the compound.
- 제 6 항에 따른 발광 소자를 포함하는 전자 장치.An electronic device comprising the light emitting element according to claim 6.
- 제 9 항에 따른 전자 장치는 디스플레이 장치 또는 조명 장치인 것을 특징으로 하는 전자 장치.The electronic device of claim 9, wherein the electronic device is a display device or a lighting device.
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| CN109503643A (en) * | 2017-09-14 | 2019-03-22 | 北京夏禾科技有限公司 | Siliceous luminous organic material |
| CN111196822A (en) * | 2018-11-20 | 2020-05-26 | 北京夏禾科技有限公司 | Compound containing silicon fluorenyl and fluorenyl structures and electroluminescent device containing compound |
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| KR102554212B1 (en) | 2018-01-18 | 2023-07-11 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof |
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