WO2020096167A1 - 유기 발광 소자 - Google Patents
유기 발광 소자 Download PDFInfo
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- WO2020096167A1 WO2020096167A1 PCT/KR2019/009197 KR2019009197W WO2020096167A1 WO 2020096167 A1 WO2020096167 A1 WO 2020096167A1 KR 2019009197 W KR2019009197 W KR 2019009197W WO 2020096167 A1 WO2020096167 A1 WO 2020096167A1
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- compound
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- 239000010410 layer Substances 0.000 claims abstract description 252
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 48
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- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 229910001417 caesium ion Inorganic materials 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- GQSGZTBDVNUIQS-DGCLKSJQSA-N ciclonicate Chemical group C1C(C)(C)C[C@H](C)C[C@H]1OC(=O)C1=CC=CN=C1 GQSGZTBDVNUIQS-DGCLKSJQSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- MNXYJVWXMUBENA-UHFFFAOYSA-N dinaphthofuran Chemical group C1=CC=CC2=C(C3=C(C4=CC=CC=C4C=C3)O3)C3=CC=C21 MNXYJVWXMUBENA-UHFFFAOYSA-N 0.000 description 1
- SYXXZXWLYNODHL-UHFFFAOYSA-N dinaphthothiophene Chemical group C1=CC=CC2=C(C3=C(C4=CC=CC=C4C=C3)S3)C3=CC=C21 SYXXZXWLYNODHL-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 238000007648 laser printing Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000001748 luminescence spectrum Methods 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- BLFVVZKSHYCRDR-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-2-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 BLFVVZKSHYCRDR-UHFFFAOYSA-N 0.000 description 1
- NYESPUIMUJRIAP-UHFFFAOYSA-N naphtho[1,2-e][1]benzofuran Chemical group C1=CC=CC2=C3C(C=CO4)=C4C=CC3=CC=C21 NYESPUIMUJRIAP-UHFFFAOYSA-N 0.000 description 1
- XRJUVKFVUBGLMG-UHFFFAOYSA-N naphtho[1,2-e][1]benzothiole Chemical group C1=CC=CC2=C3C(C=CS4)=C4C=CC3=CC=C21 XRJUVKFVUBGLMG-UHFFFAOYSA-N 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical class N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229910001419 rubidium ion Inorganic materials 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052706 scandium Inorganic materials 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
- 238000000926 separation method Methods 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 229910001427 strontium ion Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 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
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical group NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K99/00—Subject matter not provided for in other groups of this subclass
Definitions
- the anode A cathode facing the anode; And an organic layer interposed between the anode and the cathode, and including an emission layer and an auxiliary layer, wherein the emission layer and the auxiliary layer are in direct contact, the emission layer comprises a dopant, and the auxiliary layer is the first compound.
- a second compound wherein the dopant, the first compound, and the second compound satisfy Equations 1 to 3 below:
- T 1 (C1) is the lowest excitation triplet energy level of the first compound
- S 1 (D) is the lowest excitation singlet energy level of the dopant
- S 1 (C2) is the lowest excitation singlet energy level of the second compound.
- a plurality of anodes disposed in each of the first subpixel region, the second subpixel region, and the third subpixel region of the substrate;
- the third light emitting layer includes a dopant
- an organic light emitting device is provided:
- T 1 (C1) is the lowest excitation triplet energy level of the first compound
- S 1 (C2) is the lowest excitation singlet energy level of the second compound.
- FIG. 1 is a view schematically showing the structure of an organic light emitting device according to an embodiment of the present invention.
- FIG. 5 is a view showing an electroluminescence spectrum of an organic light emitting device according to Examples and Comparative Examples.
- low excitation triplet energy level is a mixture of CH 2 Cl 2 and each compound (concentration of 1 * 10 -5 M) in a quartz cell, then in liquid helium (4K) and using a PR650 spectra colorimeter.
- the lowest excitation triplet energy level was calculated by measuring the photoluminescence spectrum and comparing it with the normal room temperature photoluminescence spectrum to analyze only the peaks observed only at low temperatures.
- the photoluminescence spectrum of the film obtained by spin coating is measured using a PR650 spectra colorimeter and compared with the normal room temperature photoluminescence spectrum to observe only at low temperatures. Only the peaks of interest were analyzed to calculate the lowest excitation triplet energy level.
- the organic light emitting device 10 includes an anode 110; A cathode 120 opposed to the anode 110; And an organic layer 130 interposed between the anode 110 and the cathode 120 and including a light emitting layer and an auxiliary layer, wherein the light emitting layer and the auxiliary layer are in direct contact, and the light emitting layer includes a dopant,
- the auxiliary layer includes a first compound and a second compound, and the dopant, the first compound, and the second compound satisfy Formulas 1 to 3 below:
- T 1 (C2) is the lowest excitation triplet energy level of the second compound.
- the auxiliary layer may be interposed between the cathode and the light emitting layer.
- the light emitting region (recombination region) of the organic light emitting device may be biased toward the cathode.
- L 12 is an organic ligand
- n12 is an integer selected from 0 to 4
- Z 15 to Z 17 are each independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a C 6 -C 20 aryl group, and a C 1 -C 20 heteroaryl group,
- the dopant may be selected from the following compounds, but is not limited thereto:
- Y 22 is selected from a single bond, O, S, N (Z 23 ) and C (Z 23 ) (Z 24 );
- L 21 is selected from a substituted or unsubstituted C 5 -C 60 carbocyclic group and a substituted or unsubstituted C 1 -C 60 heterocyclic group;
- R 21 to R 28 and Z 21 to Z 26 are, independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, Hydrazono group, substituted or unsubstituted C 1 -C 60 alkyl group, substituted or unsubstituted C 2 -C 60 alkenyl group, substituted or unsubstituted C 2 -C 60 alkynyl group, substituted or unsubstituted C 1- C 60 alkoxy group, substituted or unsubstituted C 3 -C 10 cycloalkyl group, substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 cycloalkenyl group, substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, substituted or unsub
- b27 and b28 are each independently selected from 1, 2 and 3;
- the sum of k21 to k23 may be selected from 2 and 3, but is not limited thereto.
- the first compound may be selected from the following compounds, but is not limited thereto:
- the second compound may satisfy the following formulas 7 and 8-1, or the following formulas 7 and 8-2, but are not limited thereto.
- S 1 (C2) is the lowest excited singlet energy level of the second compound
- T 2 (C2) is the second excitation triplet energy level of the second compound
- K (T 2- > S 0 ) is the transition rate constant from the second excitation triplet energy level of the second compound to the bottom singlet energy level
- the second compound may be represented by the following Chemical Formula 3, but is not limited thereto:
- the anode 110 may be formed, for example, by providing an anode material on the substrate using an evaporation method or a sputtering method.
- the anode 110 may be selected from materials having a high work function to facilitate hole injection.
- the organic layer 150 is disposed on the first electrode 110.
- the organic layer 150 includes a light emitting layer and an auxiliary layer.
- the organic layer 150 includes a hole transport region interposed between the first electrode 110 and the light emitting layer and an electron transport region interposed between the light emitting layer and the second electrode 190. region).
- the hole transport region is m-MTDATA, TDATA, 2-TNATA, NPB (NPD), ⁇ -NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, TCTA (4,4 ' , 4 "-tris (N-carbazolyl) triphenylamine (4,4 ', 4" -tris (N-carbazolyl) triphenylamine)), PANI / DBSA (Polyaniline / Dodecylbenzenesulfonic acid (polyaniline / dodecylbenzenesulfonic acid)) , PEDOT / PSS (Poly (3,4-ethylenedioxythiophene) / Poly (4-styrenesulfonate) (poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate))), PANI / CSA (Polyaniline / Cam
- L 201 to L 204 are each independently a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cyclo Alkenylene group, substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 arylene group, substituted or unsubstituted C 1 -C 60 heteroarylene group, substituted or unsubstituted A substituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group,
- L 201 to L 205 are independently of each other
- xa5 may be 1, 2, 3 or 4.
- Fluorenyl group spiro-bifluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group;
- R 201 and R 202 may be connected to each other through a single bond, and / or ii) R 203 and R 204 may be connected to each other through a single bond.
- the compound represented by Chemical Formula 201 may be represented by Chemical Formula 201A:
- Chemical Formula 201 may be represented by the following Chemical Formula 201A (1), but is not limited thereto:
- Chemical Formula 201 may be represented by the following Chemical Formula 201A-1, but is not limited thereto:
- Chemical Formula 202A the compound represented by Chemical Formula 202.
- R 211 and R 212 For description of R 211 and R 212 , refer to the description of R 203 in the present specification,
- R 213 to R 217 are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 alkyl group substitution Phenyl group, -F-substituted phenyl group, pentaenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spir
- the hole transport region may have a thickness of about 100 mm2 to about 10000 mm2, for example, about 100 mm2 to about 1000 mm2. If the hole transport region includes at least one of a hole injection layer and a hole transport layer, the hole injection layer has a thickness of about 100 mm 2 to about 9000 mm 2, for example, about 100 mm 2 to about 1000 mm 2, and the hole transport layer has a thickness of about 50 mm 2 To about 2000 mm 2, for example about 100 mm 2 to about 1500 mm 2. When the thickness of the hole transport region, the hole injection layer and the hole transport layer satisfies the above-described range, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.
- the hole transport region may further include a charge-generating material to improve conductivity in addition to the above-described materials.
- the charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region.
- the LUMO of the p-dopant may be -3.5 eV or less.
- the p-dopant may include quinone derivatives such as Tetracyanoquinodimethane (TCNQ) and F4-TCNQ (2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane);
- quinone derivatives such as Tetracyanoquinodimethane (TCNQ) and F4-TCNQ (2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane);
- R 221 to R 223 are each independently a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group.
- the light emitting layer may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer for each subpixel.
- the light emitting layer has a structure in which two or more layers selected from a red light emitting layer, a green light emitting layer, and a blue light emitting layer are stacked by contact or separation, or two or more materials selected from a red light emitting material, a green light emitting material, and a blue light emitting material are layered. It has no mixed structure and can emit white light.
- the emission layer may include a host and a dopant.
- the dopant may include at least one of a phosphorescent dopant and a fluorescent dopant.
- the content of the dopant in the light emitting layer may be generally selected from about 0.01 to about 15 parts by weight with respect to about 100 parts by weight of the host, but is not limited thereto.
- the thickness of the light emitting layer may be about 100 mm 2 to about 1000 mm 2, for example, about 200 mm 2 to about 600 mm 2. When the thickness of the light emitting layer satisfies the above-described range, excellent light emission characteristics may be exhibited without substantially increasing the driving voltage.
- the host may include a compound represented by Formula 301 below.
- Ar 301 is a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
- xb11 is 1, 2 or 3
- L 301 is a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or Unsubstituted C 1 -C 10 heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 arylene group, substituted or unsubstituted C 1 -C 60 heteroarylene group, substituted or unsubstituted divalent non- An aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group,
- xb1 is an integer selected from 0 to 5
- R 301 is deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substituted or unsubstituted C 1 -C 60 Alkyl group, substituted or unsubstituted C 2 -C 60 alkenyl group, substituted or unsubstituted C 2 -C 60 alkynyl group, substituted or unsubstituted C 1 -C 60 alkoxy group, substituted or unsubstituted C 3 -C 10 cycloalkyl group, substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 cycloalkenyl group, substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, substituted or unsubstituted hwandoen C 6
- xb21 is an integer selected from 1 to 5
- Q 301 to Q 303 may be independently selected from C 1 -C 10 alkyl groups, C 1 -C 10 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups, but are not limited thereto.
- Ar 301 in Formula 301 is
- the compound represented by Chemical Formula 301 may be represented by the following Chemical Formula 301-1 or 301-2:
- a 301 to A 304 are independently of each other, benzene group, naphthalene group, phenanthrene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, pyridine group, pyrimidine group, indene group, fluorene Group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, indole group, carbazole group, benzocarbazole group, dibenzocarbazole group, furan group, benzofuran group, dibenzofuran group , Naphthofuran group, benzonaphthofuran group, dinaphthofuran group, thiophene group, benzothiophene group, dibenzothiophene group, naphthothiophene group, benzonaphthothiophene group and dinaphthothiophene group Clearly, benz
- X 301 is O, S or N-[(L 304 ) xb4 -R 304 ],
- xb22 and xb23 are each independently 0, 1 or 2
- L 302 to L 304 is independent of each other, see the description of L 301 above,
- Q 31 to Q 33 may be referred to as described herein.
- R 301 to R 304 in Formulas 301, 301-1, and 301-2 are independently of each other,
- Q 31 to Q 33 may be referred to as described herein.
- the phosphorescent dopant may include a compound represented by Chemical Formula 1.
- the fluorescent dopant may include a compound represented by the following Chemical Formula 501:
- L 501 to L 503 are each independently a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cyclo Alkenylene group, substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 arylene group, substituted or unsubstituted C 1 -C 60 heteroarylene group, substituted or unsubstituted A substituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group,
- R 501 and R 502 are each independently a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group.
- Substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted C 6 -C 60 aryloxy group, substituted or unsubstituted C 6 -C 60 arylthio group, substituted or unsubstituted C 1 -C 60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group Is selected,
- xd4 may be selected from integers from 1 to 6.
- Ar 501 in Formula 501 is
- L 501 to L 503 in Formula 501 are independently of each other
- R 501 and R 502 in Formula 501 are independently of each other
- the Q 31 to Q 33 may be selected from C 1 -C 10 alkyl groups, C 1 -C 10 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups.
- the fluorescent dopant can be selected from the following compounds FD1 to FD22:
- the fluorescent dopant may be selected from the following compounds, but is not limited thereto.
- the electron transport region includes i) a single layer structure composed of a single material, ii) a single layer structure composed of a plurality of different materials, or iii) a multilayer structure having a plurality of layers made of a plurality of different materials.
- the electron transport region may include at least one layer selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer (ETL), and an electron injection layer, but is not limited thereto.
- the electron transport region may be an electron transport layer / electron injection layer, a hole blocking layer / electron transport layer / electron injection layer, an electron control layer / electron transport layer / electron injection layer, or a buffer layer / electron transport layer / stacked sequentially from the light emitting layer / It may have a structure such as an electron injection layer, but is not limited thereto.
- the electron transport region (eg, a buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may include a metal-free compound containing at least one ⁇ electron-deficient nitrogen-containing ring. .
- ⁇ electron-deficient nitrogen-containing ring examples include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine , Quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, sinoline, phenanthridine, acridine, phenanthroline, phenazine, benzoimidazole, isobenzothiazole, benzo Oxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, azacarbazole, and the like, but is not limited thereto.
- Ar 601 is a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
- xe11 is 1, 2 or 3
- L 601 is a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or Unsubstituted C 1 -C 10 heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 arylene group, substituted or unsubstituted C 1 -C 60 heteroarylene group, substituted or unsubstituted divalent non- An aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group,
- xe1 is an integer selected from 0 to 5
- R 601 is a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted C 6 -C 60 aryloxy group, substituted or unsubstituted C 6 -C 60 arylthio group , Substituted or unsubstituted C 1 -C 60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si (Q 601 ) (
- Q 601 to Q 603 are, independently of each other, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group,
- At least one of the xe11 Ar 601 and the xe21 R 601 may include a ⁇ electron-deficient nitrogen-containing ring as described above.
- ring Ar 601 is
- xe11 in Formula 601 is 2 or more, two or more Ar 601 may be connected to each other through a single bond.
- the compound represented by 601 may be represented by the following Chemical Formula 601-1:
- X 614 is N or C (R 614 ), X 615 is N or C (R 615 ), X 616 is N or C (R 616 ), and at least one of X 614 to X 616 is N,
- L 611 to L 613 independently of each other refer to the description of L 601 above,
- xe611 to xe613 independently of each other, refer to the description of xe1 above,
- R 614 to R 616 are independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C 1 It may be selected from -C 20 alkyl group, C 1 -C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group and naphthyl group.
- xe1 and xe611 to xe613 may be 0, 1, or 2 independently of each other.
- R 601 and R 611 to R 613 are independently of each other
- the electron transport region may include, but is not limited to, at least one compound selected from the following compounds ET1 to ET36:
- the electron transport region is BCP (2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-Diphenyl-1,10-phenanthroline), Alq 3 , BAlq, TAZ ( 3- (Biphenyl-4-yl) -5- (4- tert- butylphenyl) -4-phenyl-4 H -1,2,4-triazole), NTAZ and TSPO1 (diphenyl (4- (triphenylsilyl) phenyl)- phosphine oxide).
- the thickness of the buffer layer, hole blocking layer, or electron control layer may be, independently of each other, about 20 mm 2 to about 1000 mm 2, for example, about 30 mm 2 to about 300 mm 2.
- excellent hole blocking characteristics or electron regulation characteristics may be obtained without a substantial increase in driving voltage.
- the electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material in addition to the above-described materials.
- the metal-containing material may include at least one selected from alkali metal complexes and alkaline earth metal complexes.
- the metal ion of the alkali metal complex can be selected from Li ions, Na ions, K ions, Rb ions, and Cs ions, and the metal ions of the alkaline earth metal complexes are Be ions, Mg ions, Ca ions, Sr ions and Ba It can be selected from ions.
- the ligands coordinated to the metal ions of the alkali metal complex and alkaline earth metal complex are, independently of each other, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl Oxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline And cyclopentadiene, but is not limited thereto.
- the metal-containing material may include a Li complex.
- the Li complex may include, for example, the following compound ET-D1 (lithium quinolate, LiQ) or ET-D2.
- the electron injection layer comprises: i) a single layer structure made of a single material, ii) a single layer structure made of a plurality of different materials, or iii) a multi-layer structure having a plurality of layers made of a plurality of different materials.
- the electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
- the alkali metal may be selected from Li, Na, K, Rb and Cs. According to one embodiment, the alkali metal may be Li, Na or Cs. According to another embodiment, the alkali metal may be Li or Cs, but is not limited thereto.
- the alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.
- the alkali metal compound, the alkaline earth metal compound and the rare earth metal compound may be selected from oxides and halides (eg, fluoride, chloride, bromide, iodide, etc.) of the alkali metal, the alkaline earth metal, and the rare earth metal. have.
- oxides and halides eg, fluoride, chloride, bromide, iodide, etc.
- the alkali metal compound may be selected from alkali metal oxides such as Li 2 O, Cs 2 O, K 2 O, and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, and the like. . According to an embodiment, the alkali metal compound may be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI, and KI, but is not limited thereto.
- the alkaline earth metal compound may be selected from alkaline earth metal compounds such as BaO, SrO, CaO, Ba x Sr 1-x O (0 ⁇ x ⁇ 1), Ba x Ca 1-x O (0 ⁇ x ⁇ 1), etc. have. According to an embodiment, the alkaline earth metal compound may be selected from BaO, SrO and CaO, but is not limited thereto.
- the rare earth metal compound may be selected from YbF 3 , ScF 3 , ScO 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 , and TbF 3 .
- the rare earth metal compound are YbF 3, ScF 3, TbF 3 , YbI 3, ScI 3, TbI 3 may be selected from, but is not limited to such.
- the electron injection layer is made of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described above, or , It may further include the organic material.
- the electron injection layer further includes an organic substance, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any of these The combination may be uniformly or non-uniformly dispersed in the matrix made of the organic material.
- the thickness of the electron injection layer may be about 1 mm 2 to about 100 mm 2, and about 3 mm 2 to about 90 mm 2. When the thickness of the electron injection layer satisfies the above-described range, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.
- the second electrode 190 is disposed on the organic layer 150 as described above.
- the second electrode 190 may be a cathode, which is an electron injection electrode.
- a metal, alloy, electroconductive compound having a low work function, and combinations thereof (combination) can be used as a material for the second electrode 190.
- the second electrode 190 is lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In) ), Magnesium-silver (Mg-Ag), may include at least one selected from ITO and IZO, but is not limited thereto.
- the second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
- the organic light emitting device may further include a first capping layer and / or a second capping layer.
- the first capping layer, the first electrode, the organic layer and the second electrode 190 have a structure in which they are sequentially stacked, or the first electrode, the organic layer, the second electrode and the second capping layer are sequentially stacked.
- the first capping layer, the first electrode, the organic layer, the second electrode, and the second capping layer may have a stacked structure.
- the light generated in the light emitting layer of the organic layer of the organic light emitting device may be taken out through the first electrode and the first capping layer, which are semi-transmissive or transmissive electrodes, or light generated in the light emitting layer of the organic layer of the organic light emitting device may be half It may be taken out through the second electrode and the second capping layer which are the transmissive electrode or the transmissive electrode.
- the first capping layer and the second capping layer may serve to improve external light emission efficiency by the principle of constructive interference.
- At least one of the first capping layer and the second capping layer, independently of each other, may include a compound represented by Formula 201 or a compound represented by Formula 202.
- At least one of the first capping layer and the second capping layer may include a compound selected from the compounds HT28 to HT33 and the following compounds CP1 to CP5, but is not limited thereto. no.
- deposition conditions are, for example, a deposition temperature of about 100 to about 500 ° C, about 10 It can be selected in consideration of the material to be included in the layer to be formed and the structure of the layer to be formed, within a vacuum degree of -8 to about 10 -3 torr and a deposition rate range of about 0.01 to about 100 kPa / sec.
- the organic light emitting device 20 includes a substrate partitioned into a first subpixel region, a second subpixel region, and a third subpixel region; A plurality of anodes (221, 222, 223) disposed in each of the first subpixel area, the second subpixel area, and the third subpixel area of the substrate; A cathode 280 facing the plurality of anodes; And interposed between the plurality of anodes 221, 222, and 223 and the cathode 280, and disposed in each of the first subpixel region, the second subpixel region, and the third subpixel region of the substrate.
- An organic layer including a first light emitting layer 221, a second light emitting layer 222, and a third light emitting layer 223;
- the organic layer includes an auxiliary layer disposed in the first sub-pixel region;
- the first light emitting layer includes a dopant, the auxiliary layer includes a first compound and a second compound, and the dopant, the first compound and the second compound satisfy the following formulas 1 to 3:
- T 1 (D) is the lowest excitation triplet energy level of the dopant
- T 1 (C1) is the lowest excitation triplet energy level of the first compound
- S 1 (D) is the lowest excitation singlet energy level of the dopant
- S 1 (C1) is the lowest excitation singlet energy level of the first compound
- S 1 (C2) is the lowest excitation singlet energy level of the second compound.
- an auxiliary layer may be further included in the second subpixel region and the third subpixel region of the organic layer, but is not limited thereto.
- the first light emitting layer emits blue phosphorescence
- the second light emitting layer emits green phosphorescence
- the third light emitting layer may emit red phosphorescence, but is not limited thereto.
- C 1 -C 60 alkyl group used herein refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples include methyl, ethyl, propyl, isobutyl, and sec-butyl. Group, ter-butyl group, pentyl group, iso-amyl group, hexyl group, and the like.
- the C 1 -C 60 alkylene group used herein refers to a divalent group having the same structure as the C 1 -C 60 alkyl group.
- C 2 -C 60 alkynyl group used herein refers to a hydrocarbon group containing at least one carbon triple bond at the middle or terminal of the C 2 -C 60 alkyl group, and specific examples thereof include ethynyl group, propynyl group, and the like. Is included.
- C 2 -C 60 alkynylene group used herein refers to a divalent group having the same structure as the C 2 -C 60 alkynyl group.
- the C 1 -C 60 alkoxy group used herein refers to a monovalent group having the formula -OA 101 (where A 101 is the C 1 -C 60 alkyl group), and specific examples thereof include a methoxy group and an ethoxy group. , Isopropyloxy group, and the like.
- C 3 -C 10 cycloalkyl group used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cyclo group. Heptyl groups and the like.
- the C 3 -C 10 cycloalkylene group of the specification and the second having the same structure as the above C 3 -C 10 cycloalkyl group means a group.
- C 1 -C 10 heterocycloalkyl group used herein refers to a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom. , Specific examples thereof include 1,2,3,4-oxatriazolidinyl group (1,2,3,4-oxatriazolidinyl), tetrahydrofuranyl group, tetrahydrothiophenyl group, and the like.
- AC 1 -C 10 heterocycloalkylene group used herein refers to a divalent group having the same structure as the C 1 -C 10 heterocycloalkyl group.
- a C 1 -C 10 heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom, and is a ring. Has at least one double bond in it.
- Specific examples of the C 1 -C 10 heterocycloalkenyl group include 4,5-dihydro-1,2,3,4-oxatriazolyl group, 2,3-dihydrofuranyl group, and 2,3-dihydro And thiophenyl groups.
- AC 1 -C 10 heterocycloalkenylene group used herein refers to a divalent group having the same structure as the C 1 -C 10 heterocycloalkenyl group.
- C 6 -C 60 aryl group used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and C 6 -C 60 arylene group having 6 to 60 carbocyclic aromatic systems having 6 to 60 carbon atoms. It means a divalent group having.
- Specific examples of the C 6 -C 60 aryl group include a phenyl group, a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, chrysenyl group, and the like.
- the C 6 -C 60 aryl group and the C 6 -C 60 arylene group include two or more rings, the two or more rings may be condensed with each other.
- the C 1 -C 60 heteroaryl group used herein includes a monovalent group having at least one hetero atom selected from N, O, Si, P, and S as a ring-forming atom and having a heterocyclic aromatic system having 1 to 60 carbon atoms.
- C 1 -C 60 heteroarylene group includes at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom and has 2 to 60 carbon atoms having a heterocyclic aromatic system. Means group.
- the C 1 -C 60 heteroaryl group examples include a pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, and the like.
- the C 1 -C 60 heteroaryl group and the C 1 -C 60 heteroarylene group include two or more rings, two or more rings may be condensed with each other.
- C 6 -C 60 aryloxy group -OA point 102 (where, A 102 is the C 6 -C 60 aryl group), a C 6 -C 60 arylthio group (arylthio) is -SA 103 (where , A 103 refers to the C 6 -C 60 aryl group).
- the C 1 -C 60 heteroaryloxy group refers to -OA 104 (where A 104 is the C 1 -C 60 heteroaryl group), and the C 1 -C 60 heteroarylthio group is -SA 105 (here, A 105 refers to the C 1 -C 60 heteroaryl group).
- a monovalent non-aromatic condensed polycyclic group has two or more rings condensed with each other, contains only carbon as a ring-forming atom, and the entire molecule is non-aromaticity.
- a specific example of the monovalent non-aromatic condensed polycyclic group includes a fluorenyl group and the like.
- a divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
- the monovalent non-aromatic condensed heteropolycyclic group of the present specification is at least one selected from N, O, Si, P, and S other than carbon as two or more rings condensed with each other and as ring-forming atoms.
- Specific examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group and the like.
- a divalent non-aromatic condensed heteropolycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
- the C 5 -C 60 carbocyclic group used herein refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms including only carbon as a ring-forming atom.
- the C 5 -C 60 carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group.
- the C 5 -C 60 carbocyclic group may be a ring such as benzene, a monovalent group such as a phenyl group, or a divalent group such as a phenylene group.
- a C 5 -C 60 carbocyclic group during the various modifications can be made, such as in 3 or 4 is the group number of a group.
- the C 1 -C 60 heterocyclic group has the same structure as the C 5 -C 60 carbocyclic group, and as a ring-forming atom, carbon (the number of carbon atoms may be 1 to 60), N , O, Si, P and S means a group including at least one hetero atom selected from.
- the Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, army Dino group, hydrazino group, hydrazono group, C 1 -C 60 alkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, C 1 -C 60 alkoxy group, C 3 -C 10 cycloalkyl group, C 1 -C 10 heterocycloalkyl group, C 3 -C 10 cycloalkenyl group, C 1 -C 10 heterocycloalkenyl group, C 6 -C 60 aryl group, C 1 -C 60 heteroaryl group, C 1 -C 60 C 1 -substituted with at least one selected from heteroaryloxy group, C 1 -C 60 heteroarylthio group, monovalent non-ar
- Ph means a phenyl group
- Me means a methyl group
- Et means an ethyl group
- ter-Bu or “Bu t” means a tert-butyl group
- OMe means a methoxy group
- biphenyl group means "phenyl group substituted with a phenyl group”.
- the "biphenyl group” belongs to a “substituted phenyl group” in which the substituent is "C 6 -C 60 aryl group”.
- Terphenyl group in the present specification means “phenyl group substituted with a biphenyl group”.
- the "terphenyl group” belongs to a "substituted phenyl group” in which the substituent is "C 6 -C 60 aryl group substituted with a C 6 -C 60 aryl group”.
- Evaluation Example 1 Measurement of the lowest excited triplet energy level (T 1 ) and the lowest excited singlet energy level (S 1 )
- the transient EL was measured for the compounds 301 to 304, and the results are shown in FIG. 4.
- ITO glass substrate (anode) is cut to a size of 50 mm x 50 mm x 0.7 mm, ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, followed by UV light for 30 minutes Was irradiated, exposed to ozone, cleaned, and this glass substrate was installed in a vacuum deposition apparatus.
- NPD was vacuum-deposited to a thickness of 300 mm2 to form a hole transport layer.
- Compound 201 and compound 304 were co-deposited on the hole transport layer at a volume ratio of 10:90 to form a 30 mm thick auxiliary layer.
- an electron transport layer was formed by vacuum-depositing BPyPmB to a thickness of 300 MPa on the auxiliary layer.
- LiQ was vacuum-deposited to a thickness of 10 Pa to form an electron injection layer
- Al was vapor-deposited to a thickness of 100 Pa (cathode) to prepare an organic light emitting device.
- An organic light-emitting device was manufactured in the same manner as in Example 1, except that the thickness of the light-emitting layer was set to 300 MPa.
- An organic light-emitting device was manufactured in the same manner as in Example 1, except that the first compound and the second compound of the auxiliary layer were changed as shown in Table 2, respectively.
- An organic light emitting device was manufactured in the same manner as in Example 1, except that the auxiliary layer was not formed.
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Abstract
Description
T 1(eV) | S 1(eV) | |
화합물 101 | 2.70 | 2.77 |
화합물 102 | 2.68 | 2.85 |
화합물 103 | 2.69 | 2.76 |
화합물 201 | 2.47 | 2.78 |
화합물 202 | 2.55 | 2.86 |
화합물 301 | 1.74 | 2.94 |
화합물 302 | 1.74 | 2.87 |
화합물 303 | 1.74 | 2.88 |
화합물 304 | 1.74 | 2.88 |
발광층 | 보조층 | 전류효율(Cd/A) | T 95(시간) | TTA(%) | TPQ(%) | ||
도펀트 | 제1화합물 | 제2화합물 | |||||
실시예 1 | 103 | 201 | 304 | 29 | 28 | 5 | 2.8 |
실시예 2 | 103 | 201 | 304 | 29.3 | 40 | 3 | 1.6 |
실시예 3 | 103 | 202 | 303 | 28.9 | 39 | 4 | 2.0 |
실시예 4 | 103 | 202 | 304 | 29.8 | 35 | 4 | 2.2 |
실시예 5 | 103 | 203 | 303 | 29.7 | 37 | 4 | 2.1 |
비교예 1 | 103 | 없음 | 32 | 15 | 11 | 9 |
Claims (20)
- 애노드;상기 애노드에 대향된 캐소드; 및상기 애노드 및 상기 캐소드 사이에 개재되고, 발광층 및 보조층을 포함하는 유기층; 을 포함하고,상기 발광층과 상기 보조층은 직접 접촉하고,상기 발광층은 도펀트를 포함하고,상기 보조층은 제1화합물 및 제2화합물을 포함하고,상기 도펀트, 상기 제1화합물 및 상기 제2화합물은 하기 식 1 내지 3을 만족하는, 유기 발광 소자:<식 1>T 1(D) > T 1(C1)<식 2>S 1(D) < S 1(C1)<식 3>S 1(C1) < S 1(C2)상기 식 1 내지 3 중,T 1(D)은 상기 도펀트의 최저 여기 삼중항 에너지 레벨이고,T 1(C1)은 상기 제1화합물의 최저 여기 삼중항 에너지 레벨이고,S 1(D)은 상기 도펀트의 최저 여기 일중항 에너지 레벨이고,S 1(C1)은 상기 제1화합물의 최저 여기 일중항 에너지 레벨이고,S 1(C2)은 상기 제2화합물의 최저 여기 일중항 에너지 레벨이다.
- 제1항에 있어서,상기 도펀트는 빛을 방출하고,상기 제1화합물 및 상기 제2화합물은 각각 빛을 방출하지 않는, 유기 발광 소자.
- 제1항에 있어서,상기 도펀트는 440 nm 내지 480 nm의 최대 발광 파장을 갖는 청색 인광을 방출하는, 유기 발광 소자.
- 제1항에 있어서,하기 식 4를 더 만족하는, 유기 발광 소자:<식 4>T 1(C1) > T 1(C2)상기 식 4 중,T 1(C1)은 상기 제1화합물의 최저 여기 삼중항 에너지 레벨이고,T 1(C2)은 상기 제2화합물의 최저 여기 삼중항 에너지 레벨이다.
- 제1항에 있어서,상기 보조층은 상기 애노드 및 상기 발광층 사이에 개재되는, 유기 발광 소자.
- 제5항에 있어서,상기 발광층은 호스트를 더 포함하고,상기 도펀트와 상기 호스트는 하기 식 5를 더 만족하는, 유기 발광 소자:<식 5>HOMO(D) > HOMO(H)상기 식 5 중,HOMO(D)는 상기 도펀트의 최저 점유 분자 오비탈 에너지 레벨이고,HOMO(H)는 상기 호스트의 최저 점유 분자 오비탈 에너지 레벨이다.
- 제1항에 있어서,상기 보조층은 상기 캐소드 및 상기 발광층 사이에 개재되는, 유기 발광 소자.
- 제7항에 있어서,상기 발광층은 호스트를 더 포함하고,상기 도펀트와 상기 호스트는 하기 식 6를 더 만족하는, 유기 발광 소자:<식 6>HOMO(D) < HOMO(H)상기 식 6 중,HOMO(D)는 상기 도펀트의 최저 점유 분자 오비탈 에너지 레벨이고,HOMO(H)는 상기 호스트의 최저 점유 분자 오비탈 에너지 레벨이다.
- 제1항에 있어서,상기 도펀트는 전이 금속을 포함하는, 유기 발광 소자.
- 제1항에 있어서,상기 도펀트는 하기 화학식 1로 표시되는, 유기 발광 소자:<화학식 1>M 11(L 11) n11(L 12) n12<화학식 1A>상기 화학식 1 및 1A 중,M 11은 1주기 전이 금속, 2주기 전이 금속 및 3주기 전이 금속 중에서 선택되고;L 11은 상기 화학식 1A로 표시되는 리간드 중에서 선택되고, n11은 1, 2 또는 3이고,L 12는 유기 리간드이고, n12는 0 내지 4의 정수 중에서 선택되고,X 111 내지 X 14는 서로 독립적으로, N 또는 C이고, X 11과 X 12는 단일 결합 또는 이중 결합을 통하여 연결되고, X 13와 X 14는 단일 결합 또는 이중 결합을 통하여 연결되고,A 11 및 A 12는 서로 독립적으로, C 5-C 60카보시클릭 그룹 또는 C 1-C 60헤테로시클릭 그룹이고,Y 11은 단일 결합, O, S, C(=O), N(Z 13), C(Z 13)(Z 14), C(Z 13)=C(Z 14) 또는 C(Z 13)이고, Y 11과 X 12는 단일 결합 또는 이중 결합을 통하여 연결되고, Y 11과 X 14는 단일 결합 또는 이중 결합을 통하여 연결되고,Z 11 및 Z 12는 서로 독립적으로, 단일 결합, O 또는 S이고,R 11 및 R 12는 서로 독립적으로, 수소, 중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 아미디노기, 히드라지노기, 히드라조노기, 치환 또는 비치환된 C 1-C 20알킬기, 치환 또는 비치환된 C 1-C 20알콕시기, 치환 또는 비치환된 C 3-C 10시클로알킬기, 치환 또는 비치환된 C 1-C 10헤테로시클로알킬기, 치환 또는 비치환된 C 3-C 10시클로알케닐기, 치환 또는 비치환된 C 1-C 10헤테로시클로알케닐기, 치환 또는 비치환된 C 6-C 60아릴기, 치환 또는 비치환된 C 6-C 60아릴옥시기, 치환 또는 비치환된 C 6-C 60아릴티오기, 치환 또는 비치환된 C 1-C 60헤테로아릴기, 치환 또는 비치환된 1가 비-방향족 축합다환 그룹 및 치환 또는 비치환된 1가 비-방향족 헤테로축합다환 그룹, -Si(Z 15)(Z 16)(Z 17), -N(Z 15)(Z 16), -B(Z 15)(Z 16), -C(=O(Z 15), -S(=O) 2(Z 15) 및 -P(=O)(Z 15)(Z 16) 중에서 선택되고, R 11 및 R 12 중 이웃한 두 개의 기는 선택적으로(optionally) 서로 결합하여 치환 또는 비치환된 C 5-C 30카보시클릭 그룹 또는 치환 또는 비치환된 C 1-C 30헤테로시클릭 그룹을 형성할 수 있고,Z 13 및 Z 14는, 수소, 중수소, C 1-C 20알킬기, C 1-C 20알콕시기, 페닐기, 비페닐기, 터페닐기 또는 나프틸기이고,Z 15 내지 Z 17은 서로 독립적으로, C 1-C 10알킬기, C 1-C 10알콕시기, C 6-C 20아릴기 및 C 1-C 20헤테로아릴기 중에서 선택되고,서로 인접한 복수의 R 11 및 R 12 중 2개, 3개 또는 4개는 선택적으로 서로 결합하여 4배위, 6배위 또는 8배위 리간드를 형성할 수 있고,b11 및 b12는 서로 독립적으로, 0 내지 10의 정수 중에서 선택되고,* 및 *'은 상기 화학식 1 중의 M 11과의 결합 사이트이다.
- 제1항에 있어서,상기 제1화합물는 하기 화학식 2로 표시되는, 유기 발광 소자:<화학식 2>상기 화학식 2 중,X 21은 N 및 C(R 21) 중에서 선택되고, X 22는 N 및 C(R 22) 중에서 선택되고, X 23은 N 및 C(R 23) 중에서 선택되고, X 24는 N 및 C(R 24) 중에서 선택되고, X 25는 N 및 C(R 25) 중에서 선택되고, X 21 내지 X 25 중 적어도 하나는 N이고,Y 21은 단일 결합, O, S, N(Z 21) 및 C(Z 21)(Z 22) 중에서 선택되고;Y 22는 단일 결합, O, S, N(Z 23) 및 C(Z 23)(Z 24) 중에서 선택되고;Y 23는 단일 결합, O, S, N(Z 25) 및 C(Z 25)(Z 26) 중에서 선택되고;k21 내지 k23은 서로 독립적으로, 0, 1 및 2 중에서 선택되되, k21가 0인 경우 Y 21은 존재하지 않고, k22가 0인 경우 Y 22는 존재하지 않고, k23이 0인 경우 Y 23는 존재하지 않고,L 21은 치환 또는 비치환된 C 5-C 60카보시클릭 그룹 및 치환 또는 비치환된 C 1-C 60헤테로시클릭 그룹 중에서 선택되고;a21은 0, 1, 2 및 3 중에서 선택되고;R 21 내지 R 28 및 Z 21 내지 Z 26는 서로 독립적으로, 수소, 중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 아미디노기, 히드라지노기, 히드라조노기, 치환 또는 비치환된 C 1-C 60알킬기, 치환 또는 비치환된 C 2-C 60알케닐기, 치환 또는 비치환된 C 2-C 60알키닐기, 치환 또는 비치환된 C 1-C 60알콕시기, 치환 또는 비치환된 C 3-C 10시클로알킬기, 치환 또는 비치환된 C 1-C 10헤테로시클로알킬기, 치환 또는 비치환된 C 3-C 10시클로알케닐기, 치환 또는 비치환된 C 1-C 10헤테로시클로알케닐기, 치환 또는 비치환된 C 6-C 60아릴기, 치환 또는 비치환된 C 6-C 60아릴옥시기, 치환 또는 비치환된 C 6-C 60아릴티오기, 치환 또는 비치환된 C 1-C 60헤테로아릴기, 치환 또는 비치환된 C 1-C 60헤테로아릴옥시기, 치환 또는 비치환된 C 1-C 60헤테로아릴티오기, 치환 또는 비치환된 1가 비-방향족 축합다환 그룹, 치환 또는 비치환된 1가 비-방향족 헤테로축합다환 그룹, -Si(Q 1)(Q 2)(Q 3), -B(Q 1)(Q 2), -N(Q 1)(Q 2), -P(Q 1)(Q 2), -C(=O)(Q 1), -S(=O)(Q 1), -S(=O) 2(Q 1), -P(=O)(Q 1)(Q 2) 및 -P(=S)(Q 1)(Q 2) 중에서 선택되고; R 21 내지 R 28 중 이웃한 두 개의 기는 선택적으로 서로 결합하여, 치환 또는 비치환된 C 5-C 30카보시클릭 그룹 또는 치환 또는 비치환된 C 1-C 30헤테로시클릭 그룹을 형성할 수 있고,b26은 1, 2, 3 및 4 중에서 선택되고;b27 및 b28은 서로 독립적으로, 1, 2 및 3 중에서 선택되고;Q 1 내지 Q 3는 서로 독립적으로, 수소, 중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 아미디노기, 히드라지노기, 히드라조노기, C 1-C 60알킬기, C 2-C 60알케닐기, C 2-C 60알키닐기, C 1-C 60알콕시기, C 3-C 10시클로알킬기, C 1-C 10헤테로시클로알킬기, C 3-C 10시클로알케닐기, C 1-C 10헤테로시클로알케닐기, C 6-C 60아릴기, C 6-C 60아릴옥시기, C 6-C 60아릴티오기, C 1-C 60헤테로아릴기, C 1-C 60헤테로아릴옥시기, C 1-C 60헤테로아릴티오기, 1가 비-방향족 축합다환 그룹, 1가 비-방향족 헤테로축합다환 그룹, 비페닐기 및 터페닐기 중에서 선택된다.
- 제1항에 있어서,상기 제2화합물은 하기 화학식 3으로 표시되는, 유기 발광 소자:<화학식 3>상기 화학식 3 중,X 31 및 X 32는 서로 독립적으로, 치환 또는 비치환된 C 6-C 60아릴기, 치환 또는 비치환된 C 1-C 60헤테로아릴기, 치환 또는 비치환된 1가 비-방향족 축합다환 그룹 및 치환 또는 비치환된 1가 비-방향족 헤테로축합다환 그룹 중에서 선택되고;R 31 내지 R 38은 서로 독립적으로, 수소, 중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 아미디노기, 히드라지노기, 히드라조노기, 치환 또는 비치환된 C 1-C 60알킬기, 치환 또는 비치환된 C 2-C 60알케닐기, 치환 또는 비치환된 C 2-C 60알키닐기, 치환 또는 비치환된 C 1-C 60알콕시기, 치환 또는 비치환된 C 3-C 10시클로알킬기, 치환 또는 비치환된 C 1-C 10헤테로시클로알킬기, 치환 또는 비치환된 C 3-C 10시클로알케닐기, 치환 또는 비치환된 C 1-C 10헤테로시클로알케닐기, 치환 또는 비치환된 C 6-C 60아릴기, 치환 또는 비치환된 C 6-C 60아릴옥시기, 치환 또는 비치환된 C 6-C 60아릴티오기, 치환 또는 비치환된 C 1-C 60헤테로아릴기, 치환 또는 비치환된 C 1-C 60헤테로아릴옥시기, 치환 또는 비치환된 C 1-C 60헤테로아릴티오기, 치환 또는 비치환된 1가 비-방향족 축합다환 그룹, 치환 또는 비치환된 1가 비-방향족 헤테로축합다환 그룹, -Si(Q 1)(Q 2)(Q 3), -B(Q 1)(Q 2), -N(Q 1)(Q 2), -P(Q 1)(Q 2), -C(=O)(Q 1), -S(=O)(Q 1), -S(=O) 2(Q 1), -P(=O)(Q 1)(Q 2) 및 -P(=S)(Q 1)(Q 2) 중에서 선택되고;Q 1 내지 Q 3는 서로 독립적으로, 수소, 중수소, -F, -Cl, -Br, -I, 히드록실기, 시아노기, 니트로기, 아미디노기, 히드라지노기, 히드라조노기, C 1-C 60알킬기, C 2-C 60알케닐기, C 2-C 60알키닐기, C 1-C 60알콕시기, C 3-C 10시클로알킬기, C 1-C 10헤테로시클로알킬기, C 3-C 10시클로알케닐기, C 1-C 10헤테로시클로알케닐기, C 6-C 60아릴기, C 6-C 60아릴옥시기, C 6-C 60아릴티오기, C 1-C 60헤테로아릴기, C 1-C 60헤테로아릴옥시기, C 1-C 60헤테로아릴티오기, 1가 비-방향족 축합다환 그룹, 1가 비-방향족 헤테로축합다환 그룹, 비페닐기 및 터페닐기 중에서 선택된다.
- 제1항에 있어서,상기 보조층의 두께는 30 Å 내지 100 Å인, 유기 발광 소자.
- 제1항에 있어서,상기 유기층은 상기 애노드와 상기 발광층 사이에 개재된 정공 수송 영역 및/또는 상기 발광층과 상기 캐소드 사이에 개재된 전자 수송 영역을 더 포함하고,상기 정공 수송 영역은, 정공 주입층, 정공 수송층, 발광 보조층, 전자 저지층 또는 이의 임의의 조합을 포함하고,상기 전자 수송 영역은, 정공 저지층, 전자 수송층, 전자 주입층 또는 이의 임의의 조합을 포함한, 유기 발광 소자.
- 제1부화소 영역, 제2부화소 영역 및 제3부화소 영역으로 구획된 기판;상기 기판의 상기 제1부화소 영역, 상기 제2부화소 영역 및 상기 제3부화소 영역 각각에 배치된 복수의 애노드;상기 복수의 애노드와 대향된 캐소드; 및상기 복수의 애노드와 상기 캐소드 사이에 개재되고, 상기 기판의 상기 제1부화소 영역, 상기 제2부화소 영역 및 상기 제3부화소 영역 각각에 배치된 제1발광층, 제2발광층 및 제3발광층을 포함하는 유기층;을 포함하고;상기 유기층은 상기 제3부화소 영역에 배치된 보조층을 포함하고;상기 제3발광층은 도펀트를 포함하고,상기 보조층은 제1화합물 및 제2화합물을 포함하고,상기 도펀트, 상기 제1화합물 및 상기 제2화합물은 하기 식 1 내지 3을 만족하는, 유기 발광 소자:<식 1>T 1(D) > T 1(C1)<식 2>S 1(D) < S 1(C1)<식 3>S 1(C1) < S 1(C2)상기 식 1 내지 3 중,T 1(D)은 상기 도펀트의 최저 여기 삼중항 에너지 레벨이고,T 1(C1)은 상기 제1화합물의 최저 여기 삼중항 에너지 레벨이고,S 1(D)은 상기 도펀트의 최저 여기 일중항 에너지 레벨이고,S 1(C1)은 상기 제1화합물의 최저 여기 일중항 에너지 레벨이고,S 1(C2)은 상기 제2화합물의 최저 여기 일중항 에너지 레벨이다.
- 제18항에 있어서,상기 유기층의 상기 제2부화소 영역 및 상기 제3부화소 영역에도 보조층을 더 포함하는, 유기 발광 소자.
- 제18항에 있어서,상기 제1발광층은 청색 인광을 방출하고,상기 제2발광층은 녹색 인광을 방출하고,상기 제3발광층은 적색 인광을 방출하는, 유기 발광 소자.
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GB2103652.0A GB2591047B (en) | 2018-11-05 | 2019-07-24 | Organic light-emitting device |
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KR20150114791A (ko) * | 2014-04-02 | 2015-10-13 | 주식회사 이엘엠 | 방향족 화합물을 포함하는 유기 전기 발광 조성물 및 이를 이용한 유기 전기 발광 소자 |
KR20160110764A (ko) * | 2015-03-12 | 2016-09-22 | 덕산네오룩스 주식회사 | 유기발광소자 및 유기발광 표시장치 |
US20170077420A1 (en) * | 2015-08-25 | 2017-03-16 | Arizona Board Of Regents On Behalf Of Arizona State University | Thermally Activated Delayed Fluorescent Material Based on 9,10-Dihydro-9,9-dimethylacridine Analogues for Prolonging Device Longevity |
KR20170103358A (ko) * | 2016-03-04 | 2017-09-13 | 성균관대학교산학협력단 | 지연형광 재료 및 이를 포함하는 유기 발광장치 |
KR20180104258A (ko) * | 2017-03-10 | 2018-09-20 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
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KR20150114791A (ko) * | 2014-04-02 | 2015-10-13 | 주식회사 이엘엠 | 방향족 화합물을 포함하는 유기 전기 발광 조성물 및 이를 이용한 유기 전기 발광 소자 |
KR20160110764A (ko) * | 2015-03-12 | 2016-09-22 | 덕산네오룩스 주식회사 | 유기발광소자 및 유기발광 표시장치 |
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