WO2022177399A1 - 신규한 화합물 및 이를 이용한 유기발광 소자 - Google Patents
신규한 화합물 및 이를 이용한 유기발광 소자 Download PDFInfo
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- WO2022177399A1 WO2022177399A1 PCT/KR2022/002559 KR2022002559W WO2022177399A1 WO 2022177399 A1 WO2022177399 A1 WO 2022177399A1 KR 2022002559 W KR2022002559 W KR 2022002559W WO 2022177399 A1 WO2022177399 A1 WO 2022177399A1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 177
- -1 biphenylyl Chemical group 0.000 claims description 79
- 239000011368 organic material Substances 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 39
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 32
- 229910052805 deuterium Inorganic materials 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000006819 (C2-60) heteroaryl group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
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- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
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- 239000012044 organic layer Substances 0.000 description 66
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 58
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- 239000000706 filtrate Substances 0.000 description 37
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- 125000003342 alkenyl group Chemical group 0.000 description 7
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 7
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- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 7
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- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000010405 anode material Substances 0.000 description 5
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- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 4
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- 125000004306 triazinyl group Chemical group 0.000 description 4
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 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
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000007650 screen-printing Methods 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000010345 tape casting 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
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl 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
- 239000010409 thin film Substances 0.000 description 1
- 125000005032 thiofuranyl group Chemical group S1C(=CC=C1)* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 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
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Images
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
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- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- C07B2200/05—Isotopically modified compounds, e.g. labelled
Definitions
- the present invention relates to a novel compound and an organic light emitting device comprising the same.
- the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material.
- the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
- An organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode.
- the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, it may be made of an electron injection layer, etc.
- Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
- the present invention relates to a novel compound and an organic light emitting device comprising the same.
- the present invention provides a compound represented by the following formula (1):
- Y is O or S
- L is a single bond; substituted or unsubstituted C 6-60 arylene; or C 2-60 heteroarylene containing one or more heteroatoms among substituted or unsubstituted N, O and S;
- L 1 and L 2 are each independently a single bond; Or a substituted or unsubstituted C 6-60 arylene,
- Ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl; C 4-60 heteroaryl containing O atom; C 4-60 heteroaryl containing an S atom; C 2-60 heteroaryl containing a substituted or unsubstituted N atom; or C 2-60 heteroaryl containing two or more heteroatoms among substituted or unsubstituted N, O and S;
- R is hydrogen; or C 6-60 aryl unsubstituted or substituted with deuterium.
- the present invention is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. .
- the compound represented by Chemical Formula 1 described above may be used as a material for the organic material layer of the organic light emitting device, and may improve efficiency, low driving voltage and/or lifespan characteristics in the organic light emitting device.
- FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting layer 3 , and a cathode 4 .
- FIG. 2 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), electron blocking layer (7), light emitting layer (3), electron transport layer (8), electron injection layer (9) and an example of an organic light emitting device including a cathode 4 .
- substituted or unsubstituted refers to deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkyl group Thioxy group, arylthioxy group, alkylsulfoxy group, arylsulfoxy group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamine group, aralkylamine substituted or unsubstituted with one or more substituents selected from the group consisting of a group, a heteroarylamine group, an arylamine group, an arylphosphine group, or a
- a substituent in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.
- substituted or unsubstituted means "unsubstituted or at least one selected from the group consisting of deuterium, halogen, C 1-10 alkyl, C 1-10 alkoxy and C 6-20 aryl. , for example, substituted with 1 to 5 substituents.
- substituted with one or more substituents shall be understood to mean, for example, “substituted with 1 to 5 substituents", or “substituted with 1 or 2 substituents”.
- the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably from 1 to 40 carbon atoms. Specifically, it may be a substituent having the following structure, but is not limited thereto.
- the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a substituent of the following structural formula, but is not limited thereto.
- the number of carbon atoms of the imide group is not particularly limited, but it is preferably from 1 to 25 carbon atoms. Specifically, it may be a substituent having the following structure, but is not limited thereto.
- the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like.
- the present invention is not limited thereto.
- the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.
- examples of the halogen group include fluoro, chloro, bromo, or iodo.
- the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms.
- alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5 -Meth
- the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
- Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but is not limited thereto.
- the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
- the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group having aromaticity. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20.
- the aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
- the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, and the like, but is not limited thereto.
- heteroaryl is a heteroaryl containing at least one of O, N, Si and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but is preferably from 2 to 60 carbon atoms.
- heteroaryl include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridyl group, Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl
- the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, and the arylsilyl group is the same as the examples of the aryl group described above.
- the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the above-described alkyl group.
- heteroaryl among heteroarylamines the description regarding heteroaryl described above may be applied.
- the alkenyl group among the aralkenyl groups is the same as the examples of the above-described alkenyl groups.
- the description of the above-described aryl group may be applied except that arylene is a divalent group.
- the description of the aforementioned heteroaryl may be applied, except that heteroarylene is a divalent group.
- the hydrocarbon ring is not a monovalent group, and the description of the above-described aryl group or cycloalkyl group may be applied, except that it is formed by combining two substituents.
- the heterocycle is not a monovalent group, and the description of the above-described heteroaryl may be applied, except that it is formed by combining two substituents.
- the present invention provides a compound represented by the above formula (1).
- the compound represented by Formula 1 has a dibenzofuran/dibenzothiophene core, and a phenyl group (phenyl-D5) substituted with 5 deuteriums at position 6 of the core is substituted, and at position 1 It has a structure in which a triazinyl group is further substituted.
- the compound may have a structure in which carbon at position 8 of the dibenzofuran/dibenzothiophene is unsubstituted or substituted with aryl substituted with deuterium.
- the compound having a structure in which a triazinyl group is substituted at the 1st position and a phenyl group substituted with 5 deuterium at the 6th position of the dibenzofuran/dibenzothiophene core is a C-D bond bond energy (bond energy) ) is greater than the binding energy of the C-H bond, so it has a stronger binding energy in the molecule compared to the compound without a phenyl group substituted with deuterium, and thus improved material stability may be exhibited.
- the compound since deuterium is not directly substituted in the dibenzofuran/dibenzothiophene core, the compound may exhibit higher electronic stability than a compound in which deuterium is directly substituted in the core.
- the lifespan characteristics of the organic light emitting device employing the compound may be remarkably improved.
- Ar 1 and Ar 2 which are substituents of the triazinyl group are any one substituent selected from the group consisting of:
- C 4-60 heteroaryl containing an O atom refers to a monovalent heterocyclic group having 4 to 60 carbon atoms while including at least one O atom which is a hetero atom, and including the O atom
- Examples of C 4-60 heteroaryl include thiofuranyl, dibenzofuranyl, benzonaphthofuranyl and dinaphthofuranyl.
- C 4-60 heteroaryl containing an S atom refers to a monovalent heterocyclic group having 4 to 60 carbon atoms while including at least one S atom, which is a hetero atom, and including the S atom.
- Examples of C 4-60 heteroaryl include thiophenyl, benzothiophenyl, dibenzothiophenyl, benzonaphthothiophenyl and dinaphthothiophenyl.
- C 2-60 heteroaryl containing an N atom means a monovalent heterocyclic group having 2 to 60 carbon atoms while including at least one N atom, which is a hetero atom, and including the N atom
- Examples of C 2-60 heteroaryl include imidazolyl, pyrrolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, indolyl, carbazolyl and benzocarba sleepiness, etc. are mentioned.
- C 2-60 heteroaryl containing two or more heteroatoms from N, O and S means having 2 to 60 carbon atoms while including two or more types of heteroatoms N, O and S atoms.
- Ar 1 and Ar 2 do not include C 4-60 heteroaryl including an O atom substituted with a substituent and C 4-60 heteroaryl including an S atom substituted with a substituent. This is because the compound may exhibit high electronic stability when used as a host material of the light emitting layer compared to the compound in which Ar 1 and/or Ar 2 is an O or S-containing heteroaryl group substituted with a substituent such as a phenyl group.
- Ar 1 and Ar 2 are each independently C 6-20 aryl unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, methyl and phenyl; unsubstituted dibenzofuranyl; unsubstituted dibenzothiophenyl; or C 2-20 heteroaryl comprising N atoms unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, methyl and phenyl.
- Ar 1 and Ar 2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl;
- phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl and carbazolyl are each independently unsubstituted or at least one selected from the group consisting of deuterium, methyl and phenyl, preferably It may be substituted with 1 to 5 substituents.
- Ar 1 and Ar 2 may each independently be any one selected from the group consisting of, but are not limited thereto:
- Ar 1 and Ar 2 may be the same as each other.
- Ar 1 and Ar 2 may be different.
- At least one of Ar 1 and Ar 2 may be unsubstituted or substituted C 6-12 aryl with deuterium.
- At least one of Ar 1 and Ar 2 is , , , or can be
- L, L 1 and L 2 may be a single bond, or C 6-20 arylene unsubstituted or substituted with deuterium.
- L may be a single bond.
- L 1 and L 2 may each independently be a single bond or phenylene.
- L 1 and L 2 may each independently be a single bond, 1,2-phenylene, 1,3-phenylene, or 1,4-phenylene.
- L 1 and L 2 are both single bonds;
- L 1 and L 2 may be a single bond, and the other may be 1,2-phenylene, 1,3-phenylene, or 1,4-phenylene.
- L 1 and L 2 may be the same as each other. or L 1 and L 2 may be different.
- R is hydrogen; or unsubstituted or substituted C 6-20 aryl with deuterium.
- R is hydrogen; phenyl unsubstituted or substituted with deuterium; biphenylyl unsubstituted or substituted with deuterium; or unsubstituted or naphthyl substituted with deuterium.
- R is hydrogen, , , , or can be
- R when R is not hydrogen, that is, when R is C 6-60 aryl unsubstituted or substituted with deuterium, R may be the same as Ar 1 or Ar 2 .
- the compound may be represented by any one of the following 1-1 to 1-5:
- Y, L 1 , L 2 , Ar 1 and Ar 2 are as defined in Formula 1 above.
- X is halogen, preferably bromo, or chloro, and the description of the remaining substituents is as defined above.
- the compound represented by Formula 1 may be prepared by Suzuki-coupling reaction of reactants A1 and A2.
- the Suzuki-coupling reaction is preferably performed under a palladium catalyst and a base, and the reactor for the reaction may be changed to a reactor known in the art.
- Such a manufacturing method may be more specific in Preparation Examples to be described later.
- the present invention provides an organic light emitting device including the compound represented by the formula (1).
- the present invention provides a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. .
- the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
- the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer.
- the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
- the organic material layer may include a light emitting layer, wherein the organic material layer including the compound may be a light emitting layer.
- the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein the organic material layer including the compound may be a light emitting layer or an electron transport layer.
- the organic material layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein the organic material layer containing the compound may be a light emitting layer or an electron transport layer.
- the organic material layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer, wherein the organic material layer comprising the compound is a light emitting layer or an electron transport layer can be
- the organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
- the organic light emitting device of the present invention further comprises a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, and an electron transport layer and an electron injection layer between the light emitting layer and the second electrode in addition to the light emitting layer as an organic layer can have a structure that
- the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic layers.
- an anode, one or more organic material layers and a cathode are sequentially stacked on a substrate, wherein the first electrode is an anode and the second electrode is a cathode.
- the first electrode is a cathode and the second electrode is an anode
- a cathode, one or more organic material layers and an anode are sequentially stacked on a substrate of an inverted type organic structure. It may be a light emitting device.
- the structure of the organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS. 1 and 2 .
- FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting layer 3 , and a cathode 4 .
- the compound represented by Formula 1 may be included in the emission layer.
- the compound represented by Formula 1 may be included in the emission layer.
- the organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Formula 1 above. Also, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
- the organic light emitting device may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
- a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
- a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode.
- an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
- an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
- the compound represented by Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
- the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
- an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890).
- the manufacturing method is not limited thereto.
- the first electrode is an anode
- the second electrode is a cathode
- the first electrode is a cathode and the second electrode is an anode
- anode material a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer.
- the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
- the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
- the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
- the hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and in the light emitting layer A compound that prevents the generated exciton from moving to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
- HOMO highest occupied molecular orbital
- the hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto.
- the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer, and as a hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and transferring them to the light emitting layer Mobility with respect to holes This large material is suitable.
- An arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion may be used as the hole transport material, but the present invention is not limited thereto.
- the electron blocking layer is formed on the hole transport layer, preferably provided in contact with the light emitting layer, to adjust the hole mobility and prevent excessive movement of electrons by increasing the hole-electron coupling probability by increasing the organic light emitting device It means a layer that plays a role in improving the efficiency of
- the electron blocking layer includes an electron blocking material, and an example of such an electron blocking material may be an arylamine-based organic material, but is not limited thereto.
- the emission layer may include a host material and a dopant material.
- a host material the compound represented by Formula 1 may be used.
- the host material may further include a condensed aromatic ring derivative or a hetero ring-containing compound in addition to the compound represented by Formula 1 above.
- condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
- heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
- the light emitting layer may further include a compound represented by the following formula (2) in addition to the compound represented by the formula (1):
- Ar' 1 and Ar' 2 are each independently, substituted or unsubstituted C 6-60 aryl; or C 2-60 heteroaryl containing one or more heteroatoms among substituted or unsubstituted N, O and S;
- R′ 1 and R′ 2 are each independently hydrogen; heavy hydrogen; C 1-60 alkyl; C 6-60 aryl; or C 2-60 heteroaryl containing one or more heteroatoms among N, O and S;
- r and s are each independently an integer of 0 to 7.
- the organic light emitting device further includes a compound represented by Formula 2 capable of efficiently transferring holes to a dopant material as a host material of the emission layer, together with the compound represented by Formula 1 having excellent electron transport ability in the emission layer.
- a compound represented by Formula 2 capable of efficiently transferring holes to a dopant material as a host material of the emission layer, together with the compound represented by Formula 1 having excellent electron transport ability in the emission layer.
- the compound represented by Formula 2 may be represented by Formula 2':
- Ar′ 1 , Ar′ 2 , R′ 1 , R′ 2 , r and s are as defined in Formula 2 above.
- Ar' 1 and Ar' 2 are each independently C 6-20 aryl, or C 2-20 heteroaryl including one heteroatom among N, O and S;
- Ar′ 1 may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and C 6-20 aryl.
- Ar' 1 and Ar' 2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, or dibenzothiophenyl;
- Ar′ 1 may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and C 6-20 aryl.
- At least one of Ar' 1 and Ar' 2 may be phenyl or biphenylyl.
- R' 1 and R' 2 may each independently be hydrogen, deuterium, or C 6-20 aryl.
- R′ 1 and R′ 2 may each independently be hydrogen, deuterium, or phenyl, but is not limited thereto.
- r and s each representing the number of R′ 1 and R′ 2 , may each independently be 0, 1, 2, 3, 4, 5, 6, or 7.
- r and s may each independently be 0, 1, or 7.
- r+s may be 0 or 1.
- the two host materials may be included in the light emitting layer in a weight ratio of 10:90 to 90:10, for example, 50:50.
- examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex.
- the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group.
- styrylamine compound a substituted or unsubstituted It is a compound in which at least one arylvinyl group is substituted in the arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
- substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
- the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
- the hole blocking layer is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to control electron mobility and prevent excessive movement of holes to increase the hole-electron coupling probability, thereby increasing the efficiency of the organic light emitting device. It means the layer that plays a role in improving.
- the hole blocking layer includes a hole blocking material, and examples of the hole blocking material include azine derivatives including triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; A compound into which an electron withdrawing group is introduced, such as a phosphine oxide derivative, may be used, but the present invention is not limited thereto.
- the electron transport layer serves to transport the electrons received from the electron injection layer to the emission layer, and is formed on the emission layer or the hole blocking layer.
- the electron transport layer includes an electron transport material, and as the electron transport material, a material having high electron mobility is suitable. Specific examples of the electron transport material include an Al complex of 8-hydroxyquinoline; complexes comprising Alq 3 ; organic radical compounds; hydroxyflavone-metal complexes; and triazine derivatives, but is not limited thereto.
- a complex compound or a nitrogen-containing 5-membered ring derivative may be used together as an electron transport material.
- the electron injection layer serves to inject electrons from the electrode, and is formed on the electron transport layer.
- the electron injection material included in the electron injection layer include LiF, NaCl, CsF, Li 2 O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, Imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, etc. derivatives thereof, metal complex compounds and nitrogen-containing 5-membered ring derivatives may be used, but the present invention is not limited thereto.
- the organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided light emitting device, and in particular, may be a bottom emission device requiring relatively high luminous efficiency.
- the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
- A-1 50 g, 166.7 mmol
- potassium carbonate was added, and stirred and heated to 140°C.
- the mixture was cooled to room temperature and then water was added.
- the formed solid was filtered. This was again added to 497 mL of chloroform to dissolve, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure.
- A-2 50 g, 178.6 mmol
- phenylboronic acid-D5 22.7 g, 178.6 mmol
- potassium carbonate 74.1 g, 535.8 mmol
- tetrakistriphenyl-phosphinopalladium 6.2 g, 5.4 mmol
- A-3 50 g, 139.2 mmol
- bis (pinacolato) diboron 38.9 g, 153.2 mmol
- potassium acetate 40.1 g, 417.7 mmol
- palladium dibenzylideneacetone palladium 2.4 g, 4.2 mmol
- tricyclohexylphosphine 2.3 g, 8.4 mmol
- A-1 50 g, 166.7 mmol
- phenylboronic acid-D5 21.2 g, 166.7 mmol
- potassium carbonate 69.1 g, 500.1 mmol
- tetrakistriphenyl-phosphinopalladium 5.8 g, 5 mmol
- B-4 50 g, 138.5 mmol
- phenylboronic acid 16.9 g, 138.5 mmol
- potassium carbonate 57.4 g, 415.5 mmol
- tetrakistriphenyl-phosphinopalladium 4.8 g, 4.2 mmol
- C-1 50 g, 139.2 mmol
- bis (pinacolato) diboron 38.9 g, 153.2 mmol
- potassium acetate 40.1 g, 417.7 mmol
- palladium dibenzylideneacetone palladium 2.4 g, 4.2 mmol
- tricyclohexylphosphine 2.3 g, 8.4 mmol
- B-4 50 g, 138.5 mmol
- phenylboronic acid-D5 17.6 g, 138.5 mmol
- potassium carbonate 57.4 g, 415.5 mmol
- tetrakistriphenyl-phosphinopalladium 4.8 g, 4.2 mmol
- B-4 50 g, 138.5 mmol
- naphthalen-2-ylboronic acid 23.8 g, 138.5 mmol
- potassium carbonate 57.4 g, 415.5 mmol
- tetrakistriphenyl-phosphinopalladium 4.8 g, 4.2 mmol
- F-1 50 g, 122.2 mmol
- bis(pinacolato)diboron 34.2 g, 134.4 mmol
- potassium acetate 35.2 g, 366.6 mmol
- palladium dibenzylideneacetone palladium 2.1 g, 3.7 mmol
- tricyclohexylphosphine 2.1 g, 7.3 mmol
- G-1 50 g, 168.9 mmol
- bis (pinacolato) diboron 47.2 g, 185.8 mmol
- potassium acetate 48.7 g, 506.7 mmol
- palladium dibenzylideneacetone palladium 2.9 g, 5.1 mmol
- tricyclohexylphosphine 2.8 g, 10.1 mmol
- A-4 (20 g, 53.3 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (14.2 g, 53.3 mmol) were placed in 400 mL of tetrahydrofuran, stirred and refluxed. .
- potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 2 hours, the resulting solid was filtered after cooling to room temperature.
- A-4 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 3 hours, the resulting solid was filtered after cooling to room temperature.
- A-4 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-4-yl)-3-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 3 hours, the resulting solid was filtered after cooling to room temperature.
- A-4 (20 g, 53.3 mmol) and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (19 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature.
- A-4 (20 g, 53.3 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine (19.9 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After 2 hours of reaction, the resulting solid was filtered after cooling to room temperature.
- A-4 (20 g, 53.3 mmol) and 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (16.9 g, 53.3 mmol) were mixed with tetrahydrofuran in a nitrogen atmosphere. It was added to 400 mL, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature.
- A-4 (20 g, 53.3 mmol) and 2-chloro-4-(4-(naphthalen-1-yl)phenyl)-6-phenyl-1,3,5-triazine (21 g, 53.3 mmol) in nitrogen atmosphere ) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature.
- A-4 (20 g, 53.3 mmol) and 2-chloro-3-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (19 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After 2 hours of reaction, the resulting solid was filtered after cooling to room temperature.
- D-2 (20 g, 43.8 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (17.2 g, 43.8 mmol) were added to 400 mL of tetrahydrofuran, stirred and refluxed. .
- potassium carbonate (18.2 g, 131.5 mmol) was dissolved in 18 mL of water, and the mixture was sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (1.5 g, 1.3 mmol) was added. After 2 hours of reaction, the resulting solid was filtered after cooling to room temperature.
- A-4 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 3 hours, the resulting solid was filtered after cooling to room temperature.
- A-4 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-4-yl)-3-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature.
- A-4 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-4-yl)-3-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After the reaction for 3 hours, the resulting solid was filtered after cooling to room temperature.
- A-4 (20 g, 53.3 mmol) and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (19 g, 53.3 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.6 mmol) was added. After 2 hours of reaction, the resulting solid was filtered after cooling to room temperature.
- E-2 (20 g, 37.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (10.1 g, 37.9 mmol) were placed in 400 mL of tetrahydrofuran, stirred and refluxed. . Thereafter, potassium carbonate (15.7 g, 113.8 mmol) was dissolved in 16 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.3 g, 1.1 mmol) was added. After the reaction for 1 hour, the resulting solid was filtered after cooling to room temperature.
- F-2 (20 g, 39.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (10.7 g, 39.9 mmol) were placed in 400 mL of tetrahydrofuran, stirred and refluxed. . Thereafter, potassium carbonate (16.5 g, 119.7 mmol) was dissolved in 17 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.4 g, 1.2 mmol) was added. After the reaction for 3 hours, the resulting solid was filtered after cooling to room temperature.
- G-2 (20 g, 51.1 mmol) and 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine (19.1 g, 51.1 mmol) was added to 400 mL of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (21.2 g, 153.4 mmol) was dissolved in 21 mL of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.8 g, 1.5 mmol) was added. After 2 hours of reaction, the resulting solid was filtered after cooling to room temperature.
- Example 1 Fabrication of an organic light emitting device
- a glass substrate coated with indium tin oxide (ITO) to a thickness of 1,300 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
- ITO indium tin oxide
- a product manufactured by Fischer Co. was used as the detergent
- distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water.
- ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water.
- ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner.
- the substrate was transported to a vacuum evaporator.
- a hole injection layer was formed by thermal vacuum deposition of the following HI-1 compound to a thickness of 50 ⁇ on the ITO transparent electrode prepared as described above.
- the following HT-1 compound was thermally vacuum-deposited to a thickness of 250 ⁇ on the hole injection layer to form a hole transport layer, and the following HT-2 compound was vacuum-deposited to a thickness of 50 ⁇ on the HT-1 deposition film to form an electron blocking layer.
- ET-1 compound was vacuum deposited to a thickness of 250 ⁇ on the light emitting layer to form an electron transport layer
- ET-2 compound and LiF were vacuum deposited at a weight ratio of 98:2 on the electron transport layer to form an electron injection layer with a thickness of 100 ⁇ formed.
- a cathode was formed by depositing aluminum to a thickness of 1000 ⁇ on the electron injection layer.
- the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ /sec
- the deposition rate of aluminum was maintained at 2 ⁇ /sec
- the vacuum degree during deposition was maintained at 1 ⁇ 10 -7 ⁇ 5 ⁇ 10 -8 torr did.
- An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 of Synthesis Example 1 as one of the host materials of the light emitting layer in Example 1.
- An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 of Synthesis Example 1 as one of the host materials of the light emitting layer in Example 1. At this time, the compounds of CE1 to CE5 of Table 1 are as follows.
- the organic light emitting device of the example using the compound represented by Formula 1 as the host material of the light emitting layer is significantly improved without a decrease in efficiency compared to the organic light emitting device of the comparative example using a compound having a different structure. It can be seen that the lifetime characteristics are shown. Therefore, it is confirmed that the compound of the present invention can improve the characteristics of the organic light emitting device compared to the comparative compound, considering that the luminous efficiency and lifespan characteristics of the organic light emitting device have a trade-off relationship with each other in general. It is possible.
- Substrate 2 Anode
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Abstract
Description
Claims (14)
- 하기 화학식 1로 표시되는 화합물:[화학식 1]상기 화학식 1에서,Y는 O 또는 S이고,D는 중수소를 의미하고,L은 단일 결합; 치환 또는 비치환된 C6-60 아릴렌; 또는 치환 또는 비치환된 N, O 및 S 중 1개 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴렌이고,L1 및 L2는 각각 독립적으로 단일 결합; 또는 치환 또는 비치환된 C6-60 아릴렌이고,Ar1 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6-60 아릴; O 원자를 포함하는 C4-60 헤테로아릴; S 원자를 포함하는 C4-60 헤테로아릴; 치환 또는 비치환된 N 원자를 포함하는 C2-60 헤테로아릴; 또는 치환 또는 비치환된 N, O 및 S 중 2종 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고,R은 수소; 또는 비치환되거나 또는 중수소로 치환된 C6-60 아릴이다.
- 제1항에 있어서,L은 단일 결합인,화합물.
- 제1항에 있어서,L1 및 L2는 각각 독립적으로 단일 결합, 또는 페닐렌인,화합물.
- 제1항에 있어서,Ar1 및 Ar2는 각각 독립적으로 페닐, 비페닐릴, 터페닐릴, 나프틸, 페난트릴, 플루오레닐, 디벤조퓨라닐, 디벤조티오페닐, 또는 카바졸일이고,여기서, 페닐, 비페닐릴, 터페닐릴, 나프틸, 페난트릴, 플루오레닐 및 카바졸일은 각각 독립적으로 비치환되거나, 또는 중수소, 메틸 및 페닐로 구성되는 군으로부터 선택되는 1개 이상의 치환기로 치환되는,화합물.
- 제1항에 있어서,Ar1 및 Ar2 중 적어도 하나는 비치환되거나, 또는 중수소로 치환된 C6-12 아릴인,화합물.
- 제1항에 있어서,R은 수소; 비치환되거나, 또는 중수소로 치환된 페닐; 비치환되거나, 또는 중수소로 치환된 비페닐릴; 또는 비치환되거나, 또는 중수소로 치환된 나프틸인,화합물.
- 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 제1항 내지 제10항 중 어느 하나의 항에 따른 화합물을 포함하는 것인, 유기 발광 소자.
- 제11항에 있어서,상기 화합물을 포함하는 유기물층은 발광층인,유기 발광 소자.
- 제12항에 있어서,상기 발광층은 하기 화학식 2로 표시되는 화합물을 더 포함하는,유기 발광 소자:[화학식 2]상기 화학식 2에서,Ar'1 및 Ar'2는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S 중 1개 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고,R'1 및 R'2는 각각 독립적으로, 수소; 중수소; C1-60 알킬; C6-60 아릴; 또는 N, O 및 S 중 1개 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고,r 및 s는 각각 독립적으로, 0 내지 7의 정수이다.
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US18/267,078 US20240083878A1 (en) | 2021-02-22 | 2022-02-22 | Compound and organic light emitting device comprising the same |
JP2023536073A JP2024500696A (ja) | 2021-02-22 | 2022-02-22 | 新規な化合物およびこれを利用した有機発光素子 |
CN202280008850.9A CN116670130A (zh) | 2021-02-22 | 2022-02-22 | 新的化合物和包含其的有机发光器件 |
EP22756597.5A EP4253378A1 (en) | 2021-02-22 | 2022-02-22 | Novel compound and organic light emitting device comprising same |
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- 2022-02-22 WO PCT/KR2022/002559 patent/WO2022177399A1/ko active Application Filing
- 2022-02-22 JP JP2023536073A patent/JP2024500696A/ja active Pending
- 2022-02-22 US US18/267,078 patent/US20240083878A1/en active Pending
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KR20000051826A (ko) | 1999-01-27 | 2000-08-16 | 성재갑 | 신규한 착물 및 그의 제조 방법과 이를 이용한 유기 발광 소자 |
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EP4253378A1 (en) | 2023-10-04 |
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