CN117222638A - Compound for organic optoelectronic device, and display device - Google Patents
Compound for organic optoelectronic device, and display device Download PDFInfo
- Publication number
- CN117222638A CN117222638A CN202280031761.6A CN202280031761A CN117222638A CN 117222638 A CN117222638 A CN 117222638A CN 202280031761 A CN202280031761 A CN 202280031761A CN 117222638 A CN117222638 A CN 117222638A
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- deuterium
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 80
- 230000005693 optoelectronics Effects 0.000 title claims abstract description 47
- 239000000126 substance Substances 0.000 claims abstract description 78
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 48
- 229910052805 deuterium Inorganic materials 0.000 claims description 48
- 239000010410 layer Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 239000012044 organic layer Substances 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 19
- 239000002019 doping agent Substances 0.000 description 16
- 230000005525 hole transport Effects 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- -1 hydroxy, amino Chemical group 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
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- 238000006467 substitution reaction Methods 0.000 description 6
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- 125000000753 cycloalkyl group Chemical group 0.000 description 5
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 108010089790 Eukaryotic Initiation Factor-3 Proteins 0.000 description 2
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000005104 aryl silyl group Chemical group 0.000 description 2
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
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- 239000012153 distilled water Substances 0.000 description 2
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- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
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- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003868 zero point energy Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- CUDDLYMAQMEZDS-UHFFFAOYSA-N 2-[3-[3-(9,9-dimethylfluoren-2-yl)phenyl]phenyl]-4,6-diphenyl-1,3,5-triazine Chemical compound CC1(C)C2=CC=CC=C2C2=C1C=C(C=C2)C1=CC=CC(=C1)C1=CC(=CC=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 CUDDLYMAQMEZDS-UHFFFAOYSA-N 0.000 description 1
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical group C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 description 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 1
- GJWBRYKOJMOBHH-UHFFFAOYSA-N 9,9-dimethyl-n-[4-(9-phenylcarbazol-3-yl)phenyl]-n-(4-phenylphenyl)fluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C(C=C1)=CC=C1C1=CC=CC=C1 GJWBRYKOJMOBHH-UHFFFAOYSA-N 0.000 description 1
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- 229940126062 Compound A Drugs 0.000 description 1
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- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- 101100446506 Mus musculus Fgf3 gene Proteins 0.000 description 1
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
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- 125000002541 furyl group Chemical group 0.000 description 1
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- 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
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Abstract
The present invention relates to: a compound for an organic optoelectronic device represented by chemical formula 1; an organic optoelectronic device comprising the same; and a display device. The details of chemical formula 1 are as defined in the specification.
Description
Technical Field
Disclosed are compounds for organic optoelectronic devices, and display devices.
Background
An organic optoelectronic device (organic optoelectronic diode) is a device capable of converting electric energy and optical energy to each other.
Organic optoelectronic devices can be broadly divided into two types according to the principle of operation. One is a photovoltaic device that generates electric energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes, respectively, and the other is a light emitting device that generates light energy from electric energy by supplying voltage or current to the electrodes.
Examples of organic optoelectronic devices include organic optoelectronic devices, organic light emitting diodes, organic solar cells, and organic photoconductor drums.
Among them, organic Light Emitting Diodes (OLEDs) have been attracting attention in recent years due to an increasing demand for flat panel display devices. An organic light emitting diode is a device that converts electric energy into light, and the performance of the organic light emitting diode is greatly affected by organic materials between electrodes.
Disclosure of Invention
Technical problem
One embodiment provides a compound for an organic optoelectronic device capable of realizing an organic optoelectronic device having low driving, high efficiency, and long lifetime.
One embodiment provides an organic optoelectronic device comprising the compound.
Another embodiment provides a display device including the organic optoelectronic device.
Technical proposal
According to one embodiment, a compound for an organic optoelectronic device is provided, the compound being represented by chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, the chemical formula is shown in the drawing,
R 1 to R 4 Each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C30 aryl,
Ar 3 to Ar 6 Each independently hydrogen or a substituted or unsubstituted C6 to C30 aryl,
m1 and m4 are each independently one of integers from 1 to 4,
m2 and m3 are each independently one of integers from 1 to 3,
R 1 to R 4 At least one of which is deuterium and which is,
Ar 1 and Ar is a group 2 Each independently is one selected from the substituents listed in group I and group II, and
Ar 1 and Ar is a group 2 Is one selected from the substituents listed in group II;
group I
Group II
In the above groups I and II,
ra and R b Each independently hydrogen, deuterium, cyano or substituted or unsubstituted C1 to C10 alkyl,
rc to Re are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C20 aryl,
d is deuterium and is a group of atoms,
m5 and m8 are each independently one of integers from 1 to 5,
m6 and m9 are each independently one of integers from 1 to 4, and
m7 and m10 are each independently one of integers from 1 to 3.
According to another embodiment, an organic optoelectronic device comprises an anode and a cathode facing each other and at least one organic layer between the anode and the cathode, wherein the organic layer comprises a compound for the organic optoelectronic device.
According to another embodiment, a display device including an organic optoelectronic device is provided.
Advantageous effects
An organic optoelectronic device having low driving, high efficiency, and long lifetime can be realized.
Drawings
Fig. 1 is a sectional view illustrating an organic light emitting diode according to an embodiment.
< description of reference numerals >
100: organic light emitting diode
105: organic layer
110: cathode electrode
120: anode
130: light-emitting layer
140: hole transfer region (hole transport region)
150: electronic transmission area (electron transport region)
Detailed Description
Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, the invention is not limited thereto, and the invention is defined by the scope of the claims.
In the present specification, when no definition is provided otherwise, "substituted" means that at least one hydrogen of a substituent or compound is replaced with deuterium, halogen, hydroxy, amino, substituted or unsubstituted C1 to C30 amino, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or a combination thereof.
In one example of the invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced with deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, or cyano. In specific examples of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group. In specific examples of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced with deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. In specific examples of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced with deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.
In the present specification, "unsubstituted" means that a hydrogen atom remains as a hydrogen atom without being replaced with another substituent.
In the present specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)".
In the present specification, when no definition is provided otherwise, "hetero" means that one to three hetero atoms selected from N, O, S, P and Si are included in one functional group and carbon remains.
In the present specification, "aryl" means a group including at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p orbitals that form a conjugate, such as phenyl, naphthyl, and the like; two or more hydrocarbon aromatic moieties may be linked by sigma bonds and may be, for example, biphenyl, terphenyl, tetrabiphenyl, and the like; and two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl.
Aryl groups may include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings sharing pairs of adjacent carbon atoms) functional groups.
In the present specification, "heterocyclyl" is a generic term for heteroaryl and may include at least one heteroatom selected from N, O, S, P and Si in place of carbon (C) in a cyclic compound such as aryl, cycloalkyl, fused rings thereof, or combinations thereof. When the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.
For example, "heteroaryl" refers to an aryl group comprising at least one heteroatom selected from N, O, S, P and Si. Two or more heteroaryl groups are directly linked by a sigma linkage, or when a heteroaryl group includes two or more rings, the two or more rings may be fused. When heteroaryl is a fused ring, each ring may include one to three heteroatoms.
More specifically, the substituted or unsubstituted C6 to C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fused tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted droyl group, a substituted or unsubstituted bistriphenyl group (triphenylene group ), a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, or a combination thereof, but is not limited thereto.
More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridine group, a substituted or unsubstituted benzoxazine group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted phenazine group.
In this specification, the hole characteristics refer to an ability to provide electrons to form holes when an electric field is applied, and holes formed in the anode can be easily injected into the light emitting layer and transported in the light emitting layer due to the conductive characteristics according to the Highest Occupied Molecular Orbital (HOMO) level.
Further, the electron characteristics refer to an ability to accept electrons when an electric field is applied, and electrons formed in the cathode may be easily injected into and transported in the light emitting layer due to a conductive characteristic according to a Lowest Unoccupied Molecular Orbital (LUMO) level.
Hereinafter, a compound for an organic optoelectronic device according to one embodiment is described.
A compound for an organic optoelectronic device according to one embodiment is represented by chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, the chemical formula is shown in the drawing,
R 1 to R 4 Each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C30 aryl,
Ar 3 to Ar 6 Each independently hydrogen or a substituted or unsubstituted C6 to C30 aryl,
m1 and m4 are each independently one of integers from 1 to 4,
m2 and m3 are each independently one of integers from 1 to 3,
R 1 to R 4 At least one of which is deuterium and which is,
Ar 1 and Ar is a group 2 Each independently is one selected from the substituents listed in group I and group II, and
Ar 1 and Ar is a group 2 Is one selected from the substituents listed in group II;
group I
Group II
In the above groups I and II,
R a and R is b Each independently hydrogen, deuterium, cyano or substituted or unsubstituted C1 to C10 alkyl,
rc to Re are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C20 aryl,
d is deuterium and is a group of atoms,
m5 and m8 are each independently one of integers from 1 to 5,
m6 and m9 are each independently one of integers from 1 to 4, and
m7 and m10 are each independently one of integers from 1 to 3.
The compound represented by chemical formula 1 has biscarbazole as a basic skeleton, a benzene moiety constituting the carbazole is substituted with at least one deuterium, and Ar as a 9 th (N-direction) substituent of the carbazole 1 And Ar is a group 2 Is substituted with deuterium.
Since the benzene moiety constituting carbazole and the 9 th (N-direction) substituent of carbazole are simultaneously substituted with deuterium, zero-point energy (zero-point energy) and vibration energy of the compound can be further reduced. Therefore, the ground state energy is further lowered and the intermolecular interaction is weakened, so that the film thus formed can be prepared in an amorphous state, thereby further improving heat resistance and improving lifetime. That is, when the compound is applied, an organic light emitting diode having low driving, high efficiency, and particularly long lifetime can be realized.
Chemical formula 1 may be represented by any one of chemical formulas 1-1 to 1-10 according to the connection position of carbazole.
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
[ chemical formulas 1-7]
[ chemical formulas 1-8]
[ chemical formulas 1-9]
[ chemical formulas 1-10]
In chemical formulas 1-1 to 1-10,
Ar 1 to Ar 6 、R 1 To R 4 And m1 to m4 are as defined above.
If R is 1 2 or more, each R 1 May be the same or different from each other.
If R is 2 2 or more, each R 2 May be the same or different from each other.
If R is 3 2 or more, each R 3 May be the same or different from each other.
If R is 4 2 or more, each R 4 May be the same or different from each other.
If Ar is 3 2 or more, then each Ar 3 May be the same or different from each other.
If Ar is 4 2 or more, then each Ar 4 May be the same or different from each otherAs such.
If Ar is 5 2 or more, then each Ar 5 May be the same or different from each other.
If Ar is 6 2 or more, then each Ar 6 May be the same or different from each other.
For example, R 1 To R 4 At least two of which may be deuterium.
For example, R 1 To R 4 May be deuterium, m1 and m4 may each be an integer 4, and m2 and m3 may each be an integer 3.
For example, R 1 And R is 2 Each of which may be deuterium, m1 may be one of integers from 1 to 4, m2 may be one of integers from 1 to 3, and R 3 And R is 4 May be hydrogen.
For example, R 3 And R is 4 Each may be deuterium, m3 may be one of integers from 1 to 3, m4 may be one of integers from 1 to 4, and R 1 And R is 2 Each may be hydrogen.
For example, R 1 And R is 4 May each be deuterium, m1 and m4 may each be an integer of 1 to 4, and R 2 And R is 3 Each may be hydrogen.
For example, R 1 To R 3 May each be deuterium, m2 and m3 may each be an integer from 1 to 3, m1 may be an integer from 1 to 4, and R 4 May be deuterium or a C6 to C30 aryl group substituted or unsubstituted with deuterium.
For example, according to R 1 To R 4 The substitution position of deuterium substitution in (1) may be represented by any one of chemical formulas 1a to 1 e.
[ chemical formula 1a ]
[ chemical formula 1b ]
[ chemical formula 1c ]
[ chemical formula 1d ]
[ chemical formula 1e ]
In chemical formulas 1a to 1e, ar 1 To Ar 6 Is as defined above.
Ar 3 To Ar 6 Each independently is hydrogen or a C6 to C30 aryl group which is unsubstituted or substituted by deuterium, and
D 3 representing substitution with three deuterium atoms.
As a specific example, ar 3 To Ar 6 And may each independently be hydrogen or a C6 to C20 aryl group unsubstituted or substituted with at least one deuterium.
For example, ar 3 To Ar 6 May each independently be hydrogen or a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a deuterium-substituted or unsubstituted terphenyl group, a deuterium-substituted or unsubstituted naphthyl group, a deuterium-substituted or unsubstituted phenanthryl group, a deuterium-substituted or unsubstituted anthryl group, a deuterium-substituted or unsubstituted bistriphenyl group or a deuterium-substituted or unsubstituted fluorenyl group.
For example, ar in chemical formula 1 1 And Ar is a group 2 Can each independently be one selected from the substituents listed in group I-1 and group II-1, and
Ar 1 and Ar is a group 2 At least one of which may be a selectionOne of the substituents listed in ad hoc II-1;
group I-1
Group II-1
In groups I-1 and II-1, are the connection points.
For example, chemical formula 1 may be represented by chemical formulas 1 to 8a or chemical formulas 1 to 8 e.
[ chemical formula 1-8a ]
[ chemical formulas 1-8e ]
In chemical formulas 1 to 8a and chemical formulas 1 to 8e,
Ar 1 and Ar is a group 2 Ar is the same as above 6 Is a C6 to C30 aryl substituted or unsubstituted with deuterium.
For example, ar 6 Can be deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted biphenyl, deuterium-substituted or unsubstituted terphenyl, deuterium-substituted or unsubstituted naphthyl, deuterium-substituted or unsubstitutedPhenanthryl, deuterium-substituted or unsubstituted anthracyl, deuterium-substituted or unsubstituted bistriphenyl or deuterium-substituted or unsubstituted fluorenyl.
For example, the compound for an organic optoelectronic device represented by chemical formula 1 may be one selected from the compounds listed in group 1, but is not limited thereto.
Group 1
As a more specific example, the compound for an organic optoelectronic device according to the present invention is represented by chemical formulas 1 to 8a, and
Ar 1 and Ar is a group 2 Each may be a phenyl group substituted with at least one deuterium, a biphenyl group substituted with at least one deuterium, a ditriphenylene group substituted with at least one deuterium, a dibenzofuranyl group substituted with at least one deuterium, or a dibenzothienyl group substituted with at least one deuterium.
In addition to the compounds described above for organic optoelectronic devices, one or more compounds may be further included.
For example, the above-described compound for an organic optoelectronic device may be applied in the form of a composition further comprising a known host material.
For example, the compounds described above for organic optoelectronic devices may further include dopants.
For example, the dopant may be a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and may be, for example, a red phosphorescent dopant.
The dopant is a material mixed in a small amount with a compound for an organic optoelectronic device to cause light emission, and may generally be a material such as a metal complex that emits light by multiple excitations into a triplet state or more. For example, the dopant may be an inorganic, organic, or organic-inorganic compound, and one or more types thereof may be used.
Examples of dopants may be phosphorescent dopants, and examples of phosphorescent dopants may be organometallic compounds including Ir, pt, os, ti, zr, hf, eu, tb, tm, fe, co, ni, ru, rh, pd or combinations thereof. For example, the phosphorescent dopant may be a compound represented by chemical formula Z, but is not limited thereto.
[ chemical formula Z ]
LMX
In formula Z, M is a metal, and L and X are the same or different and are ligands that form complexes with M.
For example, M may be Ir, pt, os, ti, zr, hf, eu, tb, tm, fe, co, ni, ru, rh, pd or a combination thereof, and L and X may be, for example, bidentate ligands.
Examples of the ligands represented by L and X may be selected from the formulas listed in group a, but are not limited thereto.
[ group A ]
In the group a of which the number of cells is equal,
R 300 to R 302 Each independently is hydrogen, deuterium, C1 to C30 alkyl substituted or unsubstituted by halogen, C6 to C30 aryl substituted or unsubstituted by C1 to C30 alkyl, or halogen, and
R 303 to R 324 Each independently is hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF 5 A trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.
As an example, it may include a dopant represented by chemical formula V.
[ chemical formula V ]
In the chemical formula V, the chemical formula is shown in the specification,
R 101 to R 116 Each independently is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or-SiR 132 R 133 R 134 ，
R 132 To R 134 Each independently of the otherIs a C1 to C6 alkyl group,
R 101 to R 116 At least one of which is a functional group represented by the formula V-1,
L 100 is a monodentate ligand of a monovalent anion and is a ligand that coordinates iridium via a lone pair of electrons of a carbon or heteroatom, and
m15 and m16 are each independently any one of integers from 0 to 3, and m15+m16 is any one of integers from 1 to 3,
[ chemical formula V-1]
In the above chemical formula V-1,
R 135 to R 139 Each independently is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or-SiR 132 R 133 R 134 ，
R 132 To R 134 Each independently is a C1 to C6 alkyl group, and
* Refers to a moiety attached to a carbon atom.
As an example, a dopant represented by formula Z-1 may be included.
[ chemical formula Z-1]
In formula Z-1, rings A, B, C and D each independently represent a 5-or 6-membered carbocyclic or heterocyclic ring;
R A 、R B 、R C and R is D Each independently represents mono-, di-, tri-, or tetra-substituted or unsubstituted;
L B 、L C and L D Each independently selected from direct bond (direct bond), BR, NR, PR, O, S, se, C = O, S = O, SO 2 CRR ', siRR ', geRR ' and groups thereofCombining;
when nA is 1, L E Selected from direct bond, BR, NR, PR, O, S, se, C = O, S = O, SO 2 CRR ', siRR ', geRR ' and combinations thereof; when nA is 0, L E Absence of; and is also provided with
R A 、R B 、R C 、R D R and R' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphine, and combinations thereof; any adjacent R A 、R B 、R C 、R D R, R and R' are optionally linked to each other to provide a ring; x is X B 、X C 、X D And X E Each independently selected from carbon and nitrogen; and Q is 1 、Q 2 、Q 3 And Q 4 Each represents oxygen or a direct bond.
The dopant according to one embodiment may be a platinum complex and may be represented, for example, by formula VI.
[ chemical formula VI ]
In the formula VI, in which the compound is a compound,
X 100 selected from O, S and NR 131 ，
R 117 To R 131 Each independently is hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or-SiR 132 R 133 R 134 ，
R 132 To R 134 Each independently is a C1 to C6 alkyl group, and
R 117 to R 131 At least one of them is-SiR 132 R 133 R 134 Or tert-butyl.
Hereinafter, an organic optoelectronic device comprising the above-described compound for an organic optoelectronic device is described.
The organic optoelectronic device may be any device that converts electric energy into light energy, and vice versa, without particular limitation, and may be, for example, an organic optoelectronic device, an organic light emitting diode, an organic solar cell, and an organic photoconductor drum.
Herein, an organic light emitting diode as one example of an organic optoelectronic device is described with reference to the accompanying drawings.
Fig. 1 is a sectional view illustrating an organic light emitting diode according to an embodiment.
Referring to fig. 1, an organic light emitting diode (100) according to one embodiment includes an anode (120) and a cathode (110) facing each other and an organic layer (105) disposed between the anode (120) and the cathode (110).
The anode (120) may be made of a conductor with a large work function to aid hole injection and may be, for example, a metal, metal oxide, and/or conductive polymer. The anode (120) may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like, or an alloy thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), and the like; combinations of metals and oxides, such as ZnO and Al or SnO 2 And 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 (110) may be made of a conductor with a small work function to aid electron injection and may be, for example, a metal, metal oxide, and/or conductive polymer. The cathode (110) may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or the like, or alloys thereof; multilayer structural materials, such as LiF/Al, liO 2 Al, liF/Ca and BaF 2 /Ca, but is not limited thereto.
The organic layer (105) may comprise the compounds described above for organic optoelectronic devices.
The organic layer (105) may include a light emitting layer (130), and the light emitting layer (130) may include the above-described compound for an organic optoelectronic device.
The composition for an organic optoelectronic device further comprising a dopant may be, for example, a red light emitting composition.
The light emitting layer (130) may contain a compound for an organic optoelectronic device such as described above as a phosphorescent host.
The organic layer may further include a charge transport region in addition to the light emitting layer.
The charge transport region may be, for example, a hole transport region (140).
The hole transport region (140) may further increase hole injection and/or hole mobility between the anode (120) and the light emitting layer (130) and block electrons.
Specifically, the hole transport region (140) may include a hole transport layer between the anode (120) and the light emitting layer (130) and a hole transport auxiliary layer between the light emitting layer (130) and the hole transport layer, and at least one of the group B compounds may be included in at least one of the hole transport layer and the hole transport auxiliary layer.
[ group B ]
In the hole transporting region (140), in addition to the above-mentioned compounds, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc., or compounds similar thereto can be used.
In addition, the charge transport region may be, for example, an electron transport region (150).
The electron transport region (150) may further increase electron injection and/or electron mobility between the cathode (110) and the light emitting layer (130) and block holes.
In particular, the electron transport region (150) may include an electron transport layer between the cathode (110) and the light emitting layer (130) and an electron transport auxiliary layer between the light emitting layer (130) and the electron transport layer, and at least one of the compounds of group C may be included in at least one of the electron transport layer and the electron transport auxiliary layer.
[ group C ]
One embodiment may provide an organic light emitting diode including a light emitting layer as an organic layer.
Another embodiment may provide an organic light emitting diode including a light emitting layer and a hole transport region as an organic layer.
Another embodiment may provide an organic light emitting diode including a light emitting layer and an electron transport region as an organic layer.
As shown in fig. 1, the organic light emitting diode according to an embodiment of the present invention may further include a hole transport region (140) and an electron transport region (150) as the organic layer (105) in addition to the light emitting layer (130).
On the other hand, the organic light emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. as the above organic layers in addition to the light emitting layer.
The organic layer may be formed by forming an anode or a cathode on the substrate using a dry film forming method such as a vacuum deposition method (evaporation), sputtering, plasma plating, and ion plating, and forming a cathode or an anode thereon to produce the organic light emitting diode (100).
The organic light emitting diode may be applied to an organic light emitting display device.
Detailed Description
Hereinafter, embodiments are described in more detail with reference to examples. However, these embodiments are exemplary, and the scope of the claims is not limited thereto.
Starting materials and reactants used in the examples and synthesis examples were purchased from Sigma Aldrich co.ltd., TCI company (TCI inc.), tokyo chemical industry (Tokyo chemical industry) or P & H technology (P & H tech) or synthesized by known methods unless otherwise specified.
(preparation of Compounds for organic optoelectronic devices)
The compounds shown as a more specific example of the compounds of the present invention were synthesized by the following steps.
Synthesis example 1: synthesis of Compounds 1-38
[ reaction type 1]
Step 1: synthesis of Compound Int1
Compound Int1 was synthesized by referring to the method disclosed in korean patent laid-open publication No. 2016-0049842.
Step 2: synthesis of Compounds 1-38
30g (0.0535 mol) of compound Int1, 40g (0.267 mol) of trifluoromethanesulfonic acid and 282g (3.35 mol) of D 6 Benzene was stirred at 10 ℃ for 24 hours. Subsequently, pure water was added thereto, followed by saturation with K 3 PO 4 And (5) neutralizing the solution. The organic layer thus obtained was concentrated and column-purified to obtain 18g of compounds 1-38 (white solid, LC-Mass Mz 578.79, C 42 H 10 D 18 N 2 )。
Synthesis example 2: synthesis of Compounds 1-98
[ reaction type 2]
19g of Compounds 1 to 98 (white solid, LC-Mass Mz 655.29, C) were obtained in the same synthetic manner as in Synthesis example 1, except that 30g (0.047 mol) of Int 2 was used instead of Int1 48 H 14 D 18 N 2 )。
Synthesis example 3: synthesis of Compounds 1-110
[ reaction type 3]
15g of Compounds 1 to 110 (white solid, LC-Mass Mz 657.31, C) were obtained in the same manner as in Synthesis example 1, except that 20g (0.036 mol) of Int 3 was used in place of Int1 48 H 13 D 19 N 2 )。
Comparative synthesis example 1: synthesis of Compound Y1
47g (0.281 mol) of carbazole and 50g (0.310 mol) of bromobenzene-D were placed 5 、53g(0.028mol)CuI、58g(0.42mol)K 2 CO 3 5g (0.028 mol) of 1, 10-phenanthroline and 560ml of DMF are stirred under reflux. When the reaction was completed, the resultant was cooled to room temperature, and pure water was added thereto to form a solid. The solid column was purified to obtain 62g of Int 4 (molecular weight: 248.33).
62g (0.25 mol) of Int 4 are added to DMF and dissolved therein. 45g (0.25 mol) of NBS was slowly added thereto at 0℃and then stirred at room temperature, thereby completing the reaction. Subsequently, pure water was added to the reaction solution to produce crystals, and the solid column was purified, thereby obtaining 80g of Int 5 (molecular weight: 327.23).
80g (0.245 mol) of Int 5, 120g (0.27 mol) of 4-biphenyl-carbazole-3-boronate, 68g (0.49 mol) of K are placed 2 CO 3 、14g(0.0122mol)Pd(PPh 3 ) 4 320ml of pure water and 490ml of THF were stirred and refluxed. When the reaction was completed, pure water was added thereto for extraction, and the organic layer thus obtained was concentrated. The mixture was purified by column to obtain 90g of Compound Y1 (molecular weight: 565.72).
Comparative synthesis example 2: synthesis of Compound Y2
35g (0.095 mol) of (phenyl-4-boronic acid) -9H-carbazole, 17g (0.105 mol) of bromobenzene-D are placed 5 、3.3g(0.0028mol)Pd(PPh 3 ) 4 、32.7g(0.237mol)K 2 CO 3 120ml of pure water and 320ml of THF were stirred and refluxed. When the reaction was completed, the resultant was cooled, pure water was added thereto and the organic layer thus separated was concentrated. The concentrate was purified by column to obtain 25g of Int 6 (molecular weight: 324.43).
20g (0.062 mol) Int 6 was dissolved in 200ml DMF and 11.5g (0.065 mol) NBS was slowly added thereto at 0 ℃. The resulting mixture was stirred at room temperature to complete the reaction, and pure water was added thereto to give a solid. The solid column was purified to obtain 23g Int 7 (molecular weight 403.33).
20g (0.0496 mol) Int 7, 22g (0.06 mol) phenyl are placed-9H-carbazole-3-boronate, 1.72g (0.0015 mol) Pd (PPh 3 ) 4 、13.7g(0.099mol)K 2 CO 3 50ml of pure water and 165ml of THF were stirred and refluxed. When the reaction was completed, the resultant was cooled, pure water was added thereto and thus the organic layer was separated and concentrated. The concentrate was purified by column to obtain 11.5g of Compound Y2 (molecular weight: 565.72).
Comparative synthesis example 3: synthesis of Compound Y3
5g of Compound Y3 (white solid, LC-Mass Mz 659.78, C) was obtained in the same manner as in Synthesis example 1, except that 20g (0.036 mol) of Int 8 was used in place of Int1 48 H 10 D 22 N 2 )。
(manufacture of organic light-emitting diode)
Example 1
The glass substrate coated with ITO (indium tin oxide) was washed with distilled water and ultrasonic waves. After washing with distilled water, the glass substrate is ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol, etc., and dried, and then transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and transferred to a vacuum deposition device. Using the obtained ITO transparent electrode as an anode, a compound a doped with 1% NDP-9 (obtained from Novaled GmbH) was vacuum deposited on an ITO substrate to formA thick hole injection layer and depositing a compound A onto the hole injection layer to form +.>A thick hole transport layer. On the hole transport layer, formation of +.>A thick hole transport auxiliary layer. In hole transport assistOn the layer, the compounds 1 to 38 obtained in synthesis example 1 as a host were formed by vacuum deposition and doped with 7wt% of PhGD as dopant +.>A thick light emitting layer. Subsequently, compound C is deposited on the light-emitting layer to form +.>A thick electron transport auxiliary layer and simultaneously vacuum depositing compound D and Liq in a weight ratio of 1:1 to form +.>A thick electron transport layer. Sequentially vacuum depositing LiQ+ on the electron transport layer>And Al->To form a cathode, and manufacturing the organic light emitting diode.
ITO/compound a (1% NDP-9 doped,) Compound A->Compound B->EML [93wt% host (Compounds 1-38): 7wt% PhGD] Compound C->Compounds D LiQ/LiQ/Al
Compound a: n- (biphenyl-4-yl) -9, 9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluoren-2-amine
Compound B: n, N-bis (9, 9-dimethyl-9H-fluoren-4-yl) -9, 9-spirodi (fluoren) -2-amine
Compound C:2- [3'- (9, 9-dimethyl-9H-fluoren-2-yl) [1,1' -biphenyl ] -3-yl ] -4, 6-diphenyl-1, 3, 5-triazine
Compound D:2- [4- [4- (4 '-cyano-1, 1' -biphenyl-4-yl) -1-naphthyl ] phenyl ] -4, 6-diphenyl-1, 3, 5-triazine
[PhGD]
Comparative examples 1 to 3
Diodes of comparative examples 1 to 3 were manufactured in the same manner as in example 1 except that the main body was changed as shown in tables 1 and 2.
Evaluation
(1) Measuring current density variation according to voltage variation
The current value flowing through the cell device in the obtained organic light emitting diode was measured using a current-voltage meter (Keithley 2400) while increasing the voltage from 0V to 10V, and the measured current value was divided by the area to provide a result.
(2) Measuring brightness change according to voltage change
Brightness was measured using a brightness meter (Minolta Cs-1000A) while increasing the voltage of the organic light emitting diode from 0V to 10V.
(3) Measurement of luminous efficiency
Using the brightness and current density measured by the above (1) and (2), the same current density (10 mA/cm 2 ) Is a light-emitting efficiency (cd/A).
The relative values based on the luminous efficiency of comparative example 3 are shown in table 2.
(4) Measurement of lifetime
At the luminance (cd/m) 2 ) Maintained at 6000cd/m 2 The time taken until the luminous efficiency (cd/a) was reduced to 97% was measured.
The relative values based on the lifetime of comparative example 1 are shown in table 1.
(5) Measurement of drive voltage
At 15mA/cm by using a current-voltage meter (Keithley 2400) 2 The driving voltage of the organic light emitting diode is measured.
The relative values of the drive voltages based on comparative example 3 are shown in table 2.
TABLE 1
TABLE 2
Referring to tables 1 and 2, the driving voltage, efficiency, and lifetime characteristics of the organic light emitting diode according to the embodiment of the present invention were significantly improved as compared to the organic light emitting diode according to the comparative example.
While the invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments. On the contrary, the invention is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.
Claims (8)
1. A compound for an organic optoelectronic device, the compound represented by chemical formula 1:
[ chemical formula 1]
In the chemical formula 1, the chemical formula is shown in the drawing,
R 1 to R 4 Each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C30 aryl,
Ar 3 to Ar 6 Each independently hydrogen or a substituted or unsubstituted C6 to C30 aryl,
m1 and m4 are each independently one of integers from 1 to 4,
m2 and m3 are each independently one of integers from 1 to 3,
R 1 to R 4 At least one of which is deuterium and which is,
Ar 1 and Ar is a group 2 Each independently is one selected from the substituents listed in group I and group II, and
Ar 1 and Ar is a group 2 Is one selected from the substituents listed in group II;
group I
Group II
In the above groups I and II,
R a and R is b Each independently hydrogen, deuterium, cyano or substituted or unsubstituted C1 to C10 alkyl,
R c to R e Each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C20 aryl,
d is deuterium and is a group of atoms,
m5 and m8 are each independently one of integers from 1 to 5,
m6 and m9 are each independently one of integers from 1 to 4, and
m7 and m10 are each independently one of integers from 1 to 3.
2. The compound for an organic optoelectronic device according to claim 1, wherein
Chemical formula 1 is represented by any one of chemical formulas 1-1 to 1-10:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
[ chemical formulas 1-7]
[ chemical formulas 1-8]
[ chemical formulas 1-9]
[ chemical formulas 1-10]
In chemical formulas 1-1 to 1-10,
Ar 1 to Ar 6 、R 1 To R 4 And m1 to m4 are as defined in claim 1.
3. The compound for an organic optoelectronic device according to claim 1, wherein
Ar in chemical formula 1 1 And Ar is a group 2 Each independently is one selected from the substituents listed in group I-1 and group II-1, and
Ar 1 and Ar is a group 2 Is one selected from the substituents listed in group II-1:
group I-1
Group II-1
In groups I-1 and II-1 above, are the connection points.
4. The compound for an organic optoelectronic device according to claim 1, wherein chemical formula 1 is represented by chemical formulas 1 to 8a or chemical formulas 1 to 8 e:
[ chemical formula 1-8a ]
[ chemical formulas 1-8e ]
In chemical formulas 1 to 8a and chemical formulas 1 to 8e,
Ar 1 and Ar is a group 2 As defined in claim 1, and
Ar 6 is a C6 to C30 aryl substituted or unsubstituted with deuterium.
5. The compound for an organic optoelectronic device according to claim 1, wherein
The compound is one selected from the compounds listed in group 1:
group 1
6. An organic optoelectronic device comprising
An anode and a cathode facing each other, and
at least one organic layer between the anode and the cathode,
wherein the organic layer comprises the compound for an organic optoelectronic device according to any one of claims 1 to 5.
7. The organic optoelectronic device of claim 6, wherein
The organic layer includes a light emitting layer, and
the light emitting layer comprises the compound for an organic optoelectronic device.
8. A display device comprising the organic optoelectronic device of claim 6.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2021-0088619 | 2021-07-06 | ||
| KR1020220082645A KR20230007961A (en) | 2021-07-06 | 2022-07-05 | Compound for organic optoelectronic device and organic optoelectronic device and display device |
| KR10-2022-0082645 | 2022-07-05 | ||
| PCT/KR2022/009714 WO2023282602A1 (en) | 2021-07-06 | 2022-07-06 | Compound for organic optoelectronic device, organic optoelectronic device, and display device |
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|---|---|
| CN117222638A true CN117222638A (en) | 2023-12-12 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202280031761.6A Pending CN117222638A (en) | 2021-07-06 | 2022-07-06 | Compound for organic optoelectronic device, and display device |
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| Country | Link |
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| CN (1) | CN117222638A (en) |
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