CN115368293A - Compound for organic photoelectric device, composition for organic photoelectric device, and display device - Google Patents
Compound for organic photoelectric device, composition for organic photoelectric device, and display device Download PDFInfo
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- CN115368293A CN115368293A CN202210542006.6A CN202210542006A CN115368293A CN 115368293 A CN115368293 A CN 115368293A CN 202210542006 A CN202210542006 A CN 202210542006A CN 115368293 A CN115368293 A CN 115368293A
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- 230000005283 ground state Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N isonitrile group Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 238000009740 moulding (composite fabrication) Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 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
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002979 perylenes Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 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
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000001771 vacuum deposition 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 238000003868 zero point energy Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The present invention relates to a compound for an organic photoelectric device, a composition for an organic photoelectric device, and a display device. Specifically, the present invention provides a compound for an organic photoelectric device represented by chemical formula 1, a composition for an organic photoelectric device including the same, an organic photoelectric device, and a display device. The details of chemical formula 1 are as defined in the specification.
Description
Citation of related applications
Priority and benefit of korean patent application No. 10-2021-0088621, filed on 6.7.2021 by the korean intellectual property office, patent application No. 10-2021-0064311, filed on 18.5.2021 by the korean intellectual property office, patent application No. 10-2022-0059688, filed on 16.5.2022 by the korean intellectual property office, and patent application No. 10-2022-0059689, filed on 16.5.2022 by the korean intellectual property office are claimed in this application, the entire contents of which are incorporated herein by reference.
Technical Field
Disclosed are a compound for an organic photoelectric device, a composition for an organic photoelectric device, and a display device.
Background
An organic photoelectric device (organic photodiode) is a device capable of converting electric energy and light energy into each other.
The organic photoelectric device can be classified as follows according to its driving principle. One is a photoelectric 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 a voltage or current to electrodes.
Examples of the organic photoelectric device include an organic photoelectric element, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.
Among them, organic Light Emitting Diodes (OLEDs) have recently attracted attention due to an increase in demand for flat panel displays. Organic light emitting diodes are devices that convert electrical energy into light, and their performance is greatly affected by organic materials between electrodes.
Disclosure of Invention
One embodiment provides a compound for an organic photoelectric device, which can realize an organic photoelectric device having high efficiency and long lifetime.
Another embodiment provides a composition for an organic photoelectric device, including a compound for an organic photoelectric device.
Another embodiment provides an organic photoelectric device including the compound for an organic photoelectric device or the composition for an organic photoelectric device.
Another embodiment provides a display device including an organic photoelectric device.
According to one embodiment, there is provided a compound for an organic photoelectric device represented by chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, the first and second,
R a and R 1 To R 18 Each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,
n1 is one of integers of 1 to 3,
Ar 1 and Ar 2 Each independently is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
L 1 and L 2 Each independently is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and
R a and R 1 To R 18 At least one of which is deuterium;
R a and R 1 To R 18 Is a C1 to C30 alkyl group substituted with at least one deuterium, or a C6 to C30 aryl group substituted with at least one deuterium; or
Ar 1 And Ar 2 At least one of which is a C1 to C30 alkyl group substituted with at least one deuterium, a C6 to C30 aryl group substituted with at least one deuterium, or a C2 group substituted with at least one deuteriumTo C30 heterocyclyl.
According to another embodiment, a composition for an organic photoelectric device includes a first compound and a second compound, wherein the first compound is the above-described compound for an organic photoelectric device, and the second compound is a compound for an organic photoelectric device represented by chemical formula 2.
[ chemical formula 2]
In the chemical formula I, the compound has the following structure,
Z 1 is N or C-L 3 -R 19 ，
Z 2 Is N or C-L 4 -R 20 ，
Z 3 Is N or C-L 5 -R 21 ，
Z 4 Is N or C-L 6 -R 22 ，
Z 5 Is N or C-L 7 -R 23 ，
Z 6 Is N or C-L 8 -R 24 ，
Z 1 To Z 6 At least two of which are N,
L 3 to L 8 Each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclyl group, or a combination thereof,
R 19 to R 24 Each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano, or combinations thereof,
R 19 to R 24 Each independently is present or adjacent groups thereof are linked to each other to provide a substituted or unsubstituted aliphatic monocyclic ring, a substituted or unsubstituted aliphatic polycyclic ring, a substituted or unsubstituted aromatic monocyclic ring, a substituted or unsubstituted aromatic polycyclic-forming ring, a substituted or unsubstituted aromatic polycyclic ringA heteroaromatic monocyclic ring, or a substituted or unsubstituted heteroaromatic polycyclic ring of (A), and
when R is 19 To R 24 Each independently of the other, R 19 To R 24 Is a substituted or unsubstituted C10 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group.
According to another embodiment, an organic photoelectric device includes an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, wherein the organic layer contains a compound for the organic photoelectric device.
According to another embodiment, a display device including an organic photoelectric device is provided.
An organic photoelectric device having low driving and long life can be realized.
Drawings
Fig. 1 is a sectional view illustrating an organic light emitting diode according to an embodiment.
Detailed Description
Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, the present invention is not limited thereto, and the present invention is defined by the scope of the claims.
In one example of the present disclosure, "substituted" means that at least one hydrogen of a substituent or compound is substituted with deuterium, halogen, hydroxyl, 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 particular embodiments of the present disclosure, "substituted" means that at least one hydrogen of the substituent or compound is substituted 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 particular embodiments of the present disclosure, "substituted" means that at least one hydrogen of the substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group. In particular embodiments of the present disclosure, "substituted" means that at least one hydrogen of the substituent or compound is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. In particular embodiments of the present disclosure, "substituted" means that at least one hydrogen in the substituent or compound is substituted with deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.
As used herein, "unsubstituted" means that a hydrogen atom is not substituted with another substituent and that the hydrogen atom remains.
As used herein, "hydrogen substitution (-H)" may include deuterium substitution (-D) or "tritium substitution (-T).
As used herein, when a definition is not otherwise provided, "hetero" means that one to three heteroatoms selected from N, O, S, P, and Si are contained in one functional group and carbon remains.
As used herein, "aryl" refers to a group comprising at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p orbitals forming a conjugate, such as phenyl, naphthyl, and the like, two or more hydrocarbon aromatic moieties may be joined by a sigma bond and may be, for example, biphenyl, terphenyl, quaterphenyl, 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 can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.
As used herein, "heterocyclyl" is a general concept of 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 a combination thereof. When the heterocyclyl is a fused ring, the entire ring or each ring of the heterocyclyl may contain one or more heteroatoms.
For example, "heteroaryl" may refer to an aryl group containing at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly connected by a sigma bond, or when the heteroaryl group comprises two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 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 tetracenyl 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 chrysyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furyl 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 thiophenyl 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 pyrimidyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof, but is not limited thereto.
In this specification, the hole characteristics refer to an ability to contribute electrons to form holes when an electric field is applied, and the holes formed in the anode may be easily injected into and transported in the light emitting layer due to a conductive characteristic according to a Highest Occupied Molecular Orbital (HOMO) level.
In addition, 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 photoelectric device according to an embodiment is described.
The compound for an organic photoelectric device according to an embodiment is represented by chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, the first and second,
R a and R 1 To R 18 Each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,
n1 is one of integers of 1 to 3,
Ar 1 and Ar 2 Each independently is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
L 1 and L 2 Each independently is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and satisfies one or more of the following conditions of chemical formula 1:
R a and R 1 To R 18 Is deuterium;
R a and R 1 To R 18 Is C1 to C30 alkyl substituted with at least one deuteriumOr a C6 to C30 aryl substituted with at least one deuterium; or
Ar 1 And Ar 2 Is a C1 to C30 alkyl group substituted with at least one deuterium, a C6 to C30 aryl group substituted with at least one deuterium, or a C2 to C30 heterocyclic group substituted with at least one deuterium.
It is known that deuterium substituted compounds have lower ground state energy due to lower zero point energy and lower vibrational energy and reduced intermolecular interaction than hydrogen substituted compounds, and thus make the thin film amorphous, further improve heat resistance, and effectively improve the lifetime of organic light emitting diodes manufactured by applying the same. Therefore, the driving voltage of the organic light emitting diode can be effectively reduced by greatly improving the lifetime through deuterium substitution and improving hole injection and transport characteristics through a structure in which carbazole is directly bonded in the nitrogen direction of biscarbazole.
For example, chemical formula 1 may be represented by any one of chemical formulae 1-I to 1-IV.
In chemical formulas 1-I to 1-IV,
R 1 to R 18 、Ar 1 、Ar 2 、L 1 And L 2 Is the same as above, and R a1 To R a4 Each independently of R a The same definition is applied.
As a specific example, chemical formula 1 may be represented by chemical formulas 1-II or chemical formulas 1-III.
In one embodiment, chemical formula 1 may be represented by chemical formula 1A.
[ chemical formula 1A ]
In the chemical formula 1A, the reaction mixture,
R a 、R 1 to R 7 And R 15 To R 18 Each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,
n1 is one of integers from 1 to 3,
Ar 1 and Ar 2 Each independently is a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and
L 1 and L 2 Each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group.
In a specific embodiment, chemical formula 1 may be represented by chemical formula 1B.
[ chemical formula 1B ]
In the chemical formula 1B, the metal oxide,
R a 、R 1 to R 4 And R 15 To R 18 Each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,
n1 is one of integers of 1 to 3,
Ar 1 and Ar 2 Each independently is a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and
L 1 and L 2 Each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group.
In a more specific embodiment, chemical formula 1 may be represented by chemical formula 1C.
[ chemical formula 1C ]
In the chemical formula 1C, the metal oxide,
R a and R 15 To R 18 Each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,
n1 is one of integers of 1 to 3,
Ar 1 and Ar 2 Each independently is a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and
L 1 and L 2 Each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group.
For example, R a And R 1 To R 18 May be deuterium; r a And R 1 To R 18 May be a C1 to C10 alkyl group substituted with at least one deuterium, or a C6 to C20 aryl group substituted with at least one deuterium; or Ar 1 And Ar 2 May be a C1 to C10 alkyl group substituted with at least one deuterium, or a C6 to C20 aryl group substituted with at least one deuterium.
For example, the C1 to C10 alkyl group substituted with at least one deuterium may include, but is not limited to, a methyl group substituted with at least one deuterium, an ethyl group substituted with at least one deuterium, an n-propyl group substituted with at least one deuterium, an isopropyl group substituted with at least one deuterium, an n-butyl group substituted with at least one deuterium, an isobutyl group substituted with at least one deuterium, a neo-butyl group substituted with at least one deuterium, a pentyl group substituted with at least one deuterium, a heptyl group substituted with at least one deuterium, an octyl group substituted with at least one deuterium, a nonyl group substituted with at least one deuterium, a decyl group substituted with at least one deuterium, and the like.
For example, the C6 to C20 aryl group substituted with at least one deuterium may include a phenyl group substituted with at least one deuterium, a biphenyl group substituted with at least one deuterium, a terphenyl group substituted with at least one deuterium, a naphthyl group substituted with at least one deuterium, a phenanthryl group substituted with at least one deuterium, an anthracenyl group substituted with at least one deuterium, a triphenylene group substituted with at least one deuterium, a fluorenyl group substituted with at least one deuterium, and the like.
According to a more specific embodiment, the C6 to C20 aryl substituted with at least one deuterium may be phenyl substituted with at least one deuterium, or biphenyl substituted with at least one deuterium, and
for example, it may be selected from the substituents of group I.
[ group I ]
In group i, is a connection point.
The most specific examples of the compound for an organic photoelectric device represented by chemical formula 1 may include the compounds of group 1, but are not limited thereto.
[ group 1]
A composition for an organic photoelectric device according to another embodiment includes a first compound and a second compound, wherein the first compound is the above-described compound for an organic photoelectric device, and the second compound is a compound that the organic compound may be a compound for a photoelectric device represented by chemical formula 2.
[ chemical formula 2]
In the chemical formula 2, the first and second organic solvents,
Z 1 is N or C-L 3 -R 19 ，
Z 2 Is N or C-L 4 -R 20 ，
Z 3 Is N or C-L 5 -R 21 ，
Z 4 Is N or C-L 6 -R 22 ，
Z 5 Is N or C-L 7 -R 23 ，
Z 6 Is N or C-L 8 -R 24 ，
Z 1 To Z 6 At least two of which are N,
L 3 to L 8 Each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclyl group, or a combination thereof,
R 19 to R 24 Each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano, or a combination thereof,
R 19 to R 24 Each independently being present or adjacent groups thereof being linked to each other to provide substituted or unsubstitutedA substituted or unsubstituted aliphatic monocyclic ring, a substituted or unsubstituted aromatic polycyclic ring, a substituted or unsubstituted heteroaromatic monocyclic ring, or a substituted or unsubstituted heteroaromatic polycyclic ring, and
when R is 19 To R 24 Each independently of the other, R 19 To R 24 Is a substituted or unsubstituted C10 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group.
Dependent on R 19 To R 24 Whether or not the adjacent groups of (a) are further condensed, chemical formula 2 may be represented, for example, by any one of chemical formulae 2-i to 2-iv.
For example, when R is 19 To R 24 Each independently present, it may be represented by chemical formula 2-I. In this case, at least one of R20, R22, and R24 is a substituted or unsubstituted C10 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group.
In another embodiment, R may be attached 20 And R 21 To form a substituted or unsubstituted aromatic monocyclic ring or a substituted or unsubstituted aromatic polycyclic ring, and may be represented by chemical formula 2-ii or chemical formula 2-iii.
In another example, R 20 And R 21 May be linked to form a substituted or unsubstituted heteroaromatic polycyclic ring, which may be represented by chemical formulas 2 to iv.
[ chemical formulas 2-IV ]
In-situ formationFrom chemical formula 2-I to chemical formula 2-IV, Z 1 、Z 3 To Z 6 、L 4 、L 6 、L 8 、R 20 、R 22 And R 24 As is the case with the above-described,
X 1 is an oxygen atom or a sulfur atom,
z of the formula 2-I 1 、Z 3 And Z 5 At least two of which are N,
z of the formula 2-II 1 、Z 4 And Z 5 At least two of which are N,
z of the formulae 2-III and 2-IV 1 、Z 4 To Z 6 At least two of which are N,
R b to R e Each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano, or combinations thereof,
n2, n4 and n5 are each independently one of an integer from 1 to 4, and
n3 is an integer of 1 or 2.
In one embodiment, the second compound may be represented by chemical formula 2-I.
Specifically, in the formula 2-I, Z 1 、Z 3 And Z 5 May each independently be N or CH, and Z 1 、Z 3 And Z 5 At least two of which may be N.
For example, Z 1 、Z 3 And Z 5 May each be N.
For example, Z 1 And Z 3 Can be N, and Z 5 May be CH.
In the chemical formula 2-I, L 4 、L 6 And L 8 May each independently be a single bond, phenylene, biphenylene, carbazolyl, dibenzofuran, dibenzothiophene or pyridylene.
For example, L 4 、L 6 And L 8 Can each independently be a single bond, m-phenylene orP-phenylene.
In the formula 2-I, R 20 、R 22 And R 24 May each independently be a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, R 20 、R 22 And R 24 May be a substituted or unsubstituted C10 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group.
Specifically, R 20 、R 22 And R 24 May each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted fused carbazolyl group, a substituted or unsubstituted fused dibenzofuranyl group, a substituted or unsubstituted fused dibenzothiophenyl group, a substituted or unsubstituted fused indolocarbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, or a substituted or unsubstituted benzoquinazolinyl group, and
R 20 、R 22 and R 24 At least one of which may be a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted fused carbazolyl group, a substituted or unsubstituted fused dibenzofuranyl group, a substituted or unsubstituted fused dibenzothiophenyl group, a substituted or unsubstituted fused indolocarbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, or a substituted or unsubstituted quinoxalinyl groupThe benzoquinazolinyl group of (a).
For example, R 20 、R 22 And R 24 May each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof,
R 20 、R 22 and R 24 At least one of which may be a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
For example, formula 2-I can be represented by any one of formula 2-IA to formula 2-ID.
[ chemical formula 2-ID ]
In the formulae 2-IA to 2-ID,
Z 1 、Z 3 、Z 5 、L 4 、L 6 、L 8 、R 22 and R 24 In the same manner as described above in the above,
X 2 is O, S or NR i ，
Z 7 Is N or C-L 9 -R 34 ，
Z 8 Is N or C-L 10 -R 35 ，
Z 9 Is N or C-L 11 -R 36 ，
Z 10 Is N or C-L 12 -R 37 ，
Z 11 Is N or C-L 13 -R 38 ，
Z 7 To Z 11 Is N is the number of N,
L 9 to L 13 Each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclyl group, or a combination thereof,
R i is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R 25 to R 38 And R 42 To R 44 Each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano, or combinations thereof,
R 25 to R 38 Each independently being present or adjacent groups thereof being linked to each other to provide a substituted or unsubstituted aliphatic monocyclic ring, a substituted or unsubstituted aliphatic polycyclic ring, a substituted or unsubstituted aromatic monocyclic ring, a substituted or unsubstituted aromatic-forming polycyclic ring, a substituted or unsubstituted heteroaromatic monocyclic ring, or a substituted or unsubstituted heteroaromatic polycyclic ring,
m is an integer of 0 to 3,
n6 to n8 are each independently one of an integer from 1 to 4,
n7 is one of integers from 1 to 3, and
ring A is represented by any one of chemical formulas A-1 to A-6,
X 3 each of which is independently O or S,
R 45 to R 49 Each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano, or combinations thereof,
n10, n12 and n14 are each independently one of an integer from 1 to 4,
n11 and n13 are integers of 1 or 2, and
* Is each fusion point.
In a specific embodiment, L 9 To L 13 May each independently be a single bond, phenylene or biphenylene,
R i may be a C6 to C12 aryl group, and
m may be one of integers of 0 to 2.
For example, the second compound may be represented by the formula 2-IB, and
for example, adjacent R 25 To R 28 The groups may be linked to form a group of the formula 2-IB-1
A substituted or unsubstituted heteroaromatic polycyclic ring represented by any one of formulas 2-ib-6.
In the chemical formulae 2-IB-1 to 2-IB-6,
X 4 is O, S CR j R k Or N-L 14 -Ar 3 ，
L 4 、L 6 、L 8 And L 14 Each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclyl group, or a combination thereof,
R j and R k Each independently substituted or unsubstitutedA C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,
Ar 3 、R 22 and R 24 Each independently substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
R 25 to R 32 And R 50 Each independently is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano, or a combination thereof, and
n15 is one of integers from 1 to 4.
In a more specific embodiment, R j And R k May each independently be a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group.
In a more specific embodiment, ar 3 May be a substituted or unsubstituted C6 to C18 aryl group, or a substituted or unsubstituted C2 to C20 heterocyclic group.
In a more specific embodiment, R 22 And R 24 May each independently be a substituted or unsubstituted C6 to C12 aryl group.
In a more specific embodiment, R 25 To R 32 And R 50 May each independently represent hydrogen, deuterium, cyano, C1 to C10 alkyl or C6 to C12 aryl.
For example, R j And R k And may each independently be a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a combination thereof.
For example, ar 3 May be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
For example, R 22 And R 24 May each independently be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.
For example, R 25 To R 32 And R 50 May each independently be hydrogen or deuterium, or at least one thereof may be phenyl, but is not limited thereto.
For example, R 42 To R 44 May each independently be hydrogen or deuterium, or at least one thereof may be phenyl, but is not limited thereto.
In a most specific embodiment, the second compound may be represented by the above chemical formula 2-IB-2, wherein X 4 Can be N-L 14 -Ar 3 Wherein n15 may be an integer from 1 to 4, wherein L 4 、L 6 、L 8 And L 14 May each independently be a single bond, or a substituted or unsubstituted phenylene group, ar 3 May be a substituted or unsubstituted C6 to C12 aryl group, R 22 And R 24 May each independently be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, and R 25 To R 32 And R 50 May each independently be hydrogen or deuterium, or at least one of them may be phenyl.
The most specific examples of the compound for an organic photoelectric device represented by chemical formula 2 may include, but are not limited to, compounds of group 2.
[ group 2]
For example, the first compound and the second compound may be included in a weight ratio of about 1. Within the above range, an appropriate weight ratio may be adjusted using the electron transport ability of the first compound and the hole transport ability of the second compound to achieve bipolar characteristics and improve efficiency and lifetime. Within the above ranges, for example, they can be contained in a weight ratio of about 10. As a specific example, they may be included in a weight ratio of about 40.
In addition to the above-described compounds for organic photoelectric devices, one or more compounds may be contained.
For example, the composition may further comprise a dopant.
The dopant may be, for example, a phosphorescent dopant, e.g., a red, green, or blue phosphorescent dopant, e.g., a red or green phosphorescent dopant.
The dopant is a material that emits light by being mixed in a small amount with a compound or a composition for an organic photoelectric device. In general, the dopant may be a material such as a metal complex which emits light by multiple excitation into a triplet state or more. The dopant may be, for example, an inorganic, organic or organic-inorganic compound, and may contain one or two or more species.
Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may include an organic metal compound including Ir, pt, os, ti, zr, hf, eu, tb, tm, fe, co, ni, ru, rh, pd, or a combination thereof. The phosphorescent dopant may use, for example, a compound represented by formula Z, but is not limited thereto.
[ chemical formula Z ]
L 15 MX 5
In formula Z, M is a metal, and L 15 And X 5 Identical to or different from each other and are ligands which form complexes with M.
M can be, for example, ir, pt, os, ti, zr, hf, eu, tb, tm, fe, co, ni, ru, rh, pd, or combinations thereof, and L 15 And X 5 May be, for example, a bidentate ligand.
From L 15 And X 5 Examples of the represented ligand may be selected from the chemical formula of group a, but are not limited thereto.
[ group A ]
In the case of the group a, the first group,
R 300 to R 302 Each independently is hydrogen, deuterium, a C1 to C30 alkyl group substituted or unsubstituted with halogen, a C6 to C30 aryl group substituted or unsubstituted with a C1 to C30 alkyl group, 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 one example, a dopant represented by formula v may be included.
[ chemical formula V ]
In the chemical formula V, the reaction mixture is,
R 101 to R 116 Each independently 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 a C1 to C6 alkyl group,
R 101 to R 116 Is a functional group represented by the chemical formula V-1,
L 100 is a bidentate ligand of a monovalent anion and is coordinated to the iridium by a lone pair of carbons or heteroatoms, and
m15 and m16 are each independently any one of integers of 0 to 3, and m15+ m16 is any one of integers of 1 to 3.
[ chemical formula V-1 ]
In the chemical formula V-1,
R 135 to R 139 Each independently 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
* Represents a moiety attached to a carbon atom.
As an example, a dopant represented by the chemical 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 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, BR, NR, PR, O, S, se, C = O, S = O, SO 2 CRR ', siRR ', geRR ', and combinations thereof;
when nA is 1, L E Selected from the group consisting of 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 Is absent; and is
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, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; any adjacent R A 、R B 、R C 、R D R and R' are optionally linked to each other to provide a ring; x B 、X C 、X D And X E Each independently selected from carbon and nitrogen; and Q 1 、Q 2 、Q 3 And Q 4 Each represents oxygen or a direct bond.
The dopant according to an embodiment may be a platinum complex, and may be represented by, for example, chemical formula vi.
[ chemical formula VI ]
In the chemical formula VI, the reaction mixture is,
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-SiR 132 R 133 R 134 Or a tert-butyl group.
Hereinafter, an organic photoelectric device including the above-described compound for an organic photoelectric device or composition for an organic photoelectric device is described.
The organic photoelectric 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 photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.
Herein, an organic light emitting diode as one example of an organic photoelectric 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 an 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 having a large work function to aid hole injection, and may be, for example, a metal oxide, and/or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), and the like; metals and oxides such as ZnO and Al or SnO 2 And Sb in combination; 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 having a small work function to aid in electron injection, and may be, for example, a metal oxide, and/or a conductive polymer. The cathode 110 mayTo be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum silver, tin, lead, cesium, barium, or an alloy thereof; such as LiF/Al, liO 2 Al, liF/Ca and BaF 2 The multi-layer structure of/Ca, but not limited thereto.
The organic layer 105 may include the above-described compound for an organic photoelectric device or a composition for an organic photoelectric device.
The organic layer 105 may include, for example, the light emitting layer 130, and the light emitting layer 130 may include, for example, the compound for an organic photoelectric device or the composition for an organic photoelectric device described above.
For example, the composition for an organic photoelectric device further comprising a dopant may be a green light emitting composition.
The light emitting layer 130 may include, for example, the above-described composition for an organic photoelectric device as a phosphorescent host.
The organic layer may include a charge transport region in addition to the light emitting layer.
The charge transport region can 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 emission layer 130, and a hole transport auxiliary layer between the emission layer 130 and the hole transport layer, and
the above-described compound for an organic photoelectric device or composition for an organic photoelectric device may be contained in at least one layer of the hole transport layer and the hole transport auxiliary layer.
For example, it may be contained in the hole transport assisting layer.
As another example, at least one of the compounds of group B 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, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A and the like, and compounds similar thereto may be used in addition to these compounds.
Also, the charge transport region may be, for example, the 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.
Specifically, 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.
The light-emitting layer may include the above-described composition for an organic photoelectric device.
Another embodiment may provide an organic light emitting diode including a light emitting layer and a hole transport region as organic layers.
The hole transport region may include the above-described compound for an organic photoelectric device.
For example, the hole transport assist layer may include the above-described compound for an organic photoelectric device.
Another embodiment may provide an organic light emitting diode including a light emitting layer and an electron transport region as organic layers.
In addition to the light emitting layer 130 as the organic layer 105, the organic light emitting diode according to an embodiment of the present invention may include a hole transport region 140 and an electron transport region 150, as shown in fig. 1.
On the other hand, the organic light emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), and the like, in addition to the light emitting layer as the above-described organic layer.
The organic light emitting diode 100 may be manufactured by forming an anode or a cathode on a substrate, forming an organic layer using a dry film forming method such as a vacuum deposition method (evaporation), sputtering, plasma plating, and ion plating, and forming the cathode or the anode thereon.
The organic light emitting diode may be applied to an organic light emitting display device.
Hereinafter, embodiments are explained in more detail with reference to examples. However, these embodiments are exemplary, and the scope is not limited thereto.
Hereinafter, the starting materials and reactants used in the examples and synthesis examples were purchased from Sigma-Aldrich co.ltd., TCI inc., or Tokyo chemical index, as long as there was no specific comment or synthesis by a known method.
(preparation of Compound for organic photoelectric device)
Synthesis example 1: synthesis of Compounds 1-32
[ reaction scheme 1]
The first step is as follows: synthesis of intermediate Int-1
Under the nitrogen condition, 9-phenyl-3, 3' -di-9H-carbazole (20g, 49.0mmol), 2-bromo-9-phenylcarbazole (15.8g, 49.0mmol), naOtBu (7.1g, 73.5mmol), pd 2 (dba) 3 (2.2g, 2.5mmol) and P (t-Bu) 3 (1.5g, 7.4 mmol) was placed in a round-bottom flask and dissolved in xylene (245 ml), followed by stirring at 120 ℃ for 12 hours under reflux. When the reaction was completed, an excess amount of distilled water was poured thereto, and then, stirred for 1 hour. The solid therein was filtered and dissolved in toluene at high temperature. In the presence of MgSO 4 After removing water and filtering the organic solvent with a pad of silica gel, the filtrate therefrom was stirred. When a solid formed, the solid was filtered and dried in vacuo to give 21.6g (68%) of intermediate Int-1.
The second step is that: synthesis of Compounds 1-32
Under nitrogen, intermediate Int-1 (21.6 g, 33.27mmol), trifluoromethanesulfonic acid (24.96g, 166.35mmol) and benzene-D 6 (174.97g, 2079.32mmol) was placed in a round bottom flask and stirred at 50 ℃ under reflux for 20 hours. When the reaction is complete, D is slowly added 2 O (124.82 ml) was poured into it for quenching, then stirred well. Titration K 3 PO 4 (aq) saturated solution to neutralize the resultant. After the reaction was completed and the aqueous layer was removed with a separatory funnel, the organic solvent was removed therefrom under reduced pressure to obtain a solid. The solid obtained was dissolved in toluene at high temperature. In the presence of MgSO 4 Removing water and using silica gel padAfter filtering the organic solvent, the filtrate therefrom was stirred. When a solid formed, the solid was filtered and dried in vacuo to give 16.73g (75%) of compounds 1-32.
Synthesis example 2: synthesis of Compounds 1-62
[ reaction scheme 2]
The first step is as follows: synthesis of intermediate Int-2
Intermediate Int-2 (22.6 g, 71%) was obtained in the same manner as in the first step of synthesis example 1 except that the reactant was changed from 2-bromo-9-phenylcarbazole to 3-bromo-9-phenylcarbazole.
The second step is that: synthesis of Compounds 1-62
Compounds 1-62 (16.6 g, 71%) were obtained in the same manner as in the second step of Synthesis example 1, except that intermediate Int-2 was used instead of intermediate Int-1.
Synthesis example 3: synthesis of Compounds 1-76[ reaction scheme 3]
The first step is as follows: synthesis of intermediate Int-3
Under nitrogen, 3' -bis-carbazole (20g, 60.2mmol), 3-bromobiphenyl (7g, 30.1mmol), naOtBu (8.7g, 90.3mmol), pd 2 (dba) 3 (2.8g, 3.0mmol) and P (t-Bu) 3 (1.8g, 9.0mmol) was placed in a round-bottom flask and dissolved in 300ml of xylene, followed by stirring at 120 ℃ for 12 hours under reflux. When the reaction was completed, an excess amount of distilled water was poured therein, and then after stirring the mixture for 1 hour, the aqueous layer was removed therefrom. Subsequent column chromatography (hexane: DCM (20%)) was used to afford 11.1g (38%) of intermediate Int-3.
The second step: synthesis of intermediate Int-4
Intermediate Int-4 (6.5g, 59%) was obtained in the same manner as the first step of synthesis example 1 except that the reactant was changed from 9-phenyl-3, 3' -di-9H-carbazole to intermediate Int-3 and from 2-bromo-9-phenylcarbazole to 3-bromo-9-phenylcarbazole.
The third step: synthesis of Compounds 1-76
Compounds 1-76 (3.5g, 52%) were obtained in the same manner as in the second step of Synthesis example 1 except that intermediate Int-4 was used instead of intermediate Int-1.
Synthesis example 4: synthesis of Compounds 1-33
[ reaction scheme 4]
The first step is as follows: synthesis of intermediate Int-5
Under nitrogen, 9-phenyl-3, 3' -di-9H-carbazole (25g, 61.2 mmol), trifluoromethanesulfonic acid (45.9g, 306.01mmol) and benzene-D 6 (321.88g, 3825.06mmol) was placed in a round bottom flask and stirred at 50 ℃ for 20 hours under reflux. When the reaction is complete, D is slowly added 2 O (229.61 ml) was poured into it for quenching, and then stirred well. Titration K 3 PO 4 (aq) saturated solution to neutralize the resultant. After completion of the reaction and removal of the aqueous layer with a separatory funnel, the organic solvent was treated by column chromatography (hexane: DCM (20%)) to give 15.5g (60%) of intermediate Int-5
The second step is that: synthesis of intermediate Int-6
Under the condition of nitrogen, iodobenzene-d is added 5 (15g, 71.8mmol), 2-bromo-9H-carbazole (17.7g, 71.8mmol), naOtBu (10.3 g)，107.6mmol)、Pd 2 (dba) 3 (3.3g, 3.6 mmol), and P (t-Bu) 3 (2.2 g,10.8 mmol) was placed in a round-bottom flask and dissolved in 360ml of xylene, followed by stirring at 120 ℃ under reflux for 12 hours. When the reaction was completed, an excess amount of distilled water was poured therein, and then after stirring the mixture for 1 hour, the aqueous layer was removed therefrom. Subsequent column chromatography (hexane: DCM (20%)) afforded 16.4g (70%) of intermediate Int-6.
The third step: synthesis of Compounds 1-33
Compounds 1-33 (17.4 g, 71%) were obtained in the same manner as in the first step of Synthesis example 1 except that intermediate Int-5 was used instead of 9-phenyl-3, 3' -di-9H-carbazole and intermediate Int-6 was used instead of 2-bromo-9H-carbazole.
Synthesis example 5: synthesis of Compounds 2-69
[ reaction scheme 5]
Under the condition of nitrogen, 2- ([ 1,1' -biphenyl radical)]-4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine (15g, 43.6mmol), 11, 12-dihydro-11-phenylindolo [2, 3-a)]Carbazole (11.6g, 34.9mmol), and NaH (1.6g, 65.4mmol) were placed in a round-bottomed flask and dissolved in 220ml of DMF, and then stirred at room temperature for 12 hours. When the reaction was completed, an excess amount of distilled water was poured thereto, and then stirred for 1 hour. The solid therein was filtered and dissolved in MCB at high temperature. Over MgSO 4 After removing water and filtering the organic solvent with a pad of silica gel, the filtrate therefrom was stirred. When a solid formed, the solid was filtered and dried in vacuo to give 20.4g (73%) of compounds 2-69.
Synthesis example 6: synthesis of Compound 3
[ reaction scheme 6]
7.6g (42%) of Compound 3 was synthesized in the same manner as in the first step of Synthesis example 1 except that 4-bromo-1, 1' -biphenyl was used instead of 2-bromo-9H-carbazole, followed by purification by column chromatography (hexane: DCM (20%)).
Comparative synthesis example 1: synthesis of Compound C-1
[ reaction scheme 7]
The first step is as follows: synthesis of intermediate Int-7
9-phenyl-3, 6-bis (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -9H-carbazole (20g, 40.4 mmol), 3-bromo-9-phenylcarbazole (32.5g, 101mmol), K 2 CO 3 (16.7g, 121.2mmol) and Pd (PPh) 3 ) 4 (2.3 g, 2mmol) was placed in a round-bottom flask and dissolved in 135ml of THF and 70ml of distilled water, followed by stirring at 60 ℃ under reflux for 12 hours. When the reaction was completed, after removing the aqueous layer, the organic solvent m was removed therefrom under reduced pressure to obtain a solid. The solid was dissolved in MCB at high temperature.
Over MgSO 4 After removing water and filtering the organic solvent with a pad of silica gel, the filtrate therefrom was stirred. When a solid formed, the solid was filtered and dried in vacuo to yield 18.2g (62%) of intermediate Int-7.
The second step: synthesis of Compound C-1
Compound C-1 (13.3g, 71%) was obtained in the same manner as in the second step of Synthesis example 1, except that intermediate Int-7 was used instead of intermediate Int-1.
Comparative synthesis example 2: synthesis of Compound C-2
[ reaction scheme 8]
The first step is as follows: synthesis of intermediate Int-8
Intermediate Int-8 (11.6 g, 54%) was obtained in the same manner as in the first step of comparative synthesis example 1 except that 9-phenyl-3- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) carbazole was used instead of 9-phenyl-3, 6-bis (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -9H-carbazole and 1-bromo-4-iodobenzene instead of 3-bromo-9-phenylcarbazole.
The second step: synthesis of intermediate Int-9
Intermediate Int-9 (26.6 g, 73%) was obtained in the same manner as in the first step of Synthesis example 1 except that intermediate Int-8 was used instead of 2-bromo-9H-carbazole.
The third step: synthesis of Compound C-2
Compound C-2 (20g, 73%) was obtained in the same manner as in the second step of Synthesis example 1, except that intermediate Int-9 was used instead of intermediate Int-1.
(production of organic light emitting diode)
Example 1
The ITO (indium tin oxide) coated glass substrate was ultrasonically cleaned with distilled water. After the washing with distilled water, the glass substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned for 10 minutes by using oxygen plasma, and moved to a vacuum depositor. Using the prepared ITO transparent electrode as an anode, 1% NDP-9-doped Compound A (Novaled GmbH) was vacuum-deposited on an ITO substrate to form
A thick hole injection layer, and depositing a compound A to
To form a hole transport layer. Synthesis of Compounds 1 to 32 of example 1 on the hole transport layer
To form a hole transport assist layer. On the hole transport auxiliary layer, a mixture of compounds 2 to 69 obtained in synthesis example 5 and compound 3 obtained in synthesis example 6 was used as a host at a weight ratio of 3
A thick light emitting layer. Subsequently, compound C is deposited on the light-emitting layer to form
A thick electron transport assist layer, and simultaneously vacuum depositing compound D and LiQ at a weight ratio of 1
A thick electron transport layer. Sequentially vacuum-depositing LiQ and Al on the electron transport layer
Thickness and
thick, thereby fabricating an organic light emitting diode.
The structure is ITO/Compound A (1% NDP-9 doping,
) Compound A
Compound 1-32
[90wt% host (compound 2-69: compound 3= 3): 10wt% PhGD]
Compound C
Compound D LiQ
/LiQ
/Al
A 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-spirobi (fluoren) -2-amine
Compound C:2- (3- (3- (9, 9-dimethyl-9H-fluoren-2-yl) phenyl) -4, 6-biphenyl-1, 3, 5-triazine
Compound D:2- (Biphenyl-4-yl) -4- (9, 9-Biphenyl-9H-fluoren-4-yl) -6-phenyl-1, 3, 5-triazine
[PhGD]
Example 2
An organic light emitting diode was fabricated in the same manner as in example 1, except that the compounds 1 to 62 of synthesis example 2 were used instead of the compounds 1 to 32.
Comparative example 1
An organic light-emitting diode was fabricated in the same manner as in example 1, except that the compound C-1 of comparative synthesis example 1 was used instead of the compounds 1 to 32.
Example 3
The glass substrate coated with ITO (indium tin oxide) was ultrasonically cleaned with distilled water. After the washing with distilled water, the glass substrate is ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned for 10 minutes by using oxygen plasma, andmove to a vacuum depositor. Using the prepared ITO transparent electrode as an anode, 1% NDP-9-doped Compound A (Novaled GmbH) was vacuum-deposited on an ITO substrate to form
A thick hole injection layer, and depositing a compound A to
To form a hole transport layer. Depositing a layer of thickness of
To form a hole transport auxiliary layer. On the hole transport auxiliary layer, a mixture of compounds 1 to 32 obtained in synthesis example 1 and compounds 2 to 69 obtained in synthesis example 5 was used as a host at a weight ratio of 7
A thick light emitting layer. Subsequently, compound C is deposited to form on the light emitting layer
A thick electron transport assist layer, and simultaneously vacuum depositing compound D and LiQ at a weight ratio of 1
A thick electron transport layer. Sequentially vacuum-depositing LiQ and Al on the electron transport layer
Thickness of
Thick, thereby fabricating an organic light emitting diode.
The structure is ITO/Compound A (1% NDP-9 doping,
) Compound A
Compound B
EML [90wt% host (compound 1-32: compound 2-69= 7)]
Compound C
Compound D LiQ
/LiQ
/Al
Example 4
An organic light-emitting diode was fabricated in the same manner as in example 3, except that the compounds 1 to 62 of synthesis example 2 were used instead of the compounds 1 to 32.
Comparative example 2
An organic light-emitting diode was fabricated in the same manner as in example 3, except that the compound C-1 of comparative synthesis example 1 was used instead of the compounds 1 to 32.
Comparative example 3
An organic light-emitting diode was fabricated in the same manner as in example 3, except that the compound C-2 of comparative synthesis example 2 was used instead of the compounds 1 to 32.
Comparative example 4
An organic light-emitting diode was fabricated in the same manner as in example 3, except that the compound Int-1 of synthesis example 1 was used instead of the compounds 1 to 32.
Comparative example 5
An organic light-emitting diode was fabricated in the same manner as in example 3, except that the compound Int-2 of synthesis example 2 was used in place of the compounds 1 to 32.
Evaluation of
The driving voltage and life span characteristics of the organic light emitting diodes according to examples 1 to 4 and comparative examples 1 to 5 were evaluated.
Specific measurement methods are as follows, and the results are shown in tables 1 and 2.
(1) Measurement of current density change according to voltage change
The obtained organic light emitting diode was measured with respect to a current value flowing in the unit device while increasing the voltage from 0V to 10V using a current-voltage meter (Keithley 2400), and the measured current value was divided by the area to provide a result.
(2) Measurement of brightness variation according to voltage variation
The luminance was measured by using a luminance meter (Minolta Cs-1000A) while the voltage of the organic light emitting diode was increased from 0V to 10V.
(3) Measurement of current efficiency
The luminance and current density and voltage at the same current density (10 mA/cm) were calculated by using the luminance and current density and voltage from items (1) and (2) 2 ) Current efficiency (cd/A).
(4) Driving voltage
By using a current-voltage meter (Keithley 2400) at 15mA/cm 2 The driving voltage of each diode is measured.
(5) Power efficiency
The power efficiency value was calculated by equation 1, and calculated based on the relative value of the power efficiency of comparative example 1 and shown in table 1.
[ equation 1]
Power efficiency (lm/W) = [ current efficiency (cd/a)/drive voltage (V) ] = Π
(II represents the ratio of the circumferential length)
(6) Measurement of lifetime
Luminance (cd/m) 2 ) Maintained at 24000cd/m 2 And the reduction in current efficiency (cd/A) to 97 was measured% of time to obtain results.
Table 2 shows relative values obtained by converting the lifetime of T97 of example 4 to 100%.
(Table 1)
| Numbering | Hole transport auxiliary layer | Power efficiency ratio (%) |
| Example 1 | 1-32 | 114％ |
| Example 2 | 1-62 | 110％ |
| Comparative example 1 | C-1 | 100％ |
Referring to table 1, the organic light emitting diode manufactured by using the compound represented by the above chemical formula 1 as a hole transport auxiliary layer material particularly achieves high efficiency characteristics.
(Table 2)
| Numbering | First main body | Second body | T97 Life ratio (%) |
| Example 3 | 1-32 | 2-69 | 117％ |
| Example 4 | 1-62 | 2-69 | 100％ |
| Comparative example 2 | C-1 | 2-69 | 13％ |
| Comparative example 3 | C-2 | 2-69 | 71％ |
| Comparative example 4 | Int-1 | 2-69 | 90％ |
| Comparative example 5 | Int-2 | 2-69 | 76％ |
Referring to table 2, the organic light emitting diode manufactured by using the compound represented by the above chemical formula 1 as a host material of the light emitting layer realizes especially long life characteristics. In particular, the organic light emitting diode using the compound represented by the above chemical formula 1 shows a significant increase in lifetime as compared to a diode using a different compound having the same or similar skeleton as that of chemical formula 1 but carbazole and deuterium substituted bonding positions or the like.
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 to be limited to the disclosed embodiments, but on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.
< description of reference numerals >
100: organic light emitting diode
105: organic layer
110: cathode electrode
120: anode
130: luminescent layer
140: hole transport region
150: an electron transport region.
Claims (15)
1. A compound for an organic photoelectric device, represented by chemical formula 1:
[ chemical formula 1]
Wherein, in chemical formula 1,
R a and R 1 To R 18 Each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,
n1 is one of integers of 1 to 3,
Ar 1 and Ar 2 Each independently is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
L 1 and L 2 Each independently is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and
R a and R 1 To R 18 At least one of which is deuterium;
R a and R 1 To R 18 Is a C1 to C30 alkyl substituted with at least one deuterium, or a C6 to C30 aryl substituted with at least one deuterium; or
Ar 1 And Ar 2 Is a C1 to C30 alkyl group substituted with at least one deuterium, a C6 to C30 aryl group substituted with at least one deuterium, or a C2 to C30 heterocyclic group substituted with at least one deuterium.
2. The compound for an organic photoelectric device according to claim 1, wherein,
chemical formula 1 is represented by any one of chemical formulae 1-i to 1-iv:
wherein, in chemical formula 1-I to chemical formula 1-IV,
R 1 to R 18 、Ar 1 、Ar 2 、L 1 And L 2 As defined in claim 1, and
R a1 to R a4 Each independently of R of claim 1 a The same definition is applied.
3. The compound for an organic photoelectric device according to claim 1, wherein,
chemical formula 1 is represented by chemical formula 1A:
[ chemical formula 1A ]
Wherein, in chemical formula 1A,
R a 、R 1 to R 7 And R 15 To R 18 Each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,
n1 is one of integers from 1 to 3,
Ar 1 and Ar 2 Each independently is a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and
L 1 and L 2 Each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group.
4. The compound for an organic photoelectric device according to claim 1, wherein,
chemical formula 1 is represented by chemical formula 1B:
[ chemical formula 1B ]
Wherein, in chemical formula 1B,
R a 、R 1 to R 4 And R 15 To R 18 Each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,
n1 is one of integers of 1 to 3,
Ar 1 and Ar 2 Each independently is a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and
L 1 and L 2 Each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group.
5. The compound for an organic photoelectric device according to claim 1, wherein,
chemical formula 1 is represented by chemical formula 1C:
[ chemical formula 1C ]
Wherein, in chemical formula 1C,
R a and R 15 To R 18 Each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,
n1 is one of integers of 1 to 3,
Ar 1 and Ar 2 Each independently is a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and
L 1 and L 2 Each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group.
6. The compound for an organic photoelectric device according to claim 1, wherein,
R a and R 1 To R 18 Is deuterium;
R a and R 1 To R 18 Is a C1 to C10 alkyl group substituted with at least one deuterium, or a C6 to C20 aryl group substituted with at least one deuterium; or
Ar 1 And Ar 2 Is a C1 to C10 alkyl group substituted with at least one deuterium, or a C6 to C20 aryl group substituted with at least one deuterium.
7. The compound for an organic photoelectric device according to claim 6, wherein,
c6 to C20 aryl substituted with at least one deuterium is selected from the group consisting of substituents of group i:
[ group I ]
Wherein, in group i, is a connection point.
8. The compound for an organic photoelectric device according to claim 1, wherein,
the compound is one of the compounds of group 1:
[ group 1]
9. A composition for use in an organic optoelectronic device comprising
A first compound and a second compound, wherein the first compound and the second compound are different,
wherein the first compound is the compound for an organic photoelectric device according to claim 1, and
the second compound is a compound represented by chemical formula 2:
[ chemical formula 2]
Wherein, in chemical formula 2,
Z 1 is N or C-L 3 -R 19 ，
Z 2 Is N or C-L 4 -R 20 ，
Z 3 Is N or C-L 5 -R 21 ，
Z 4 Is N or C-L 6 -R 22 ，
Z 5 Is N or C-L 7 -R 23 ，
Z 6 Is N or C-L 8 -R 24 ，
Z 1 To Z 6 Is N is a number of N,
L 3 to L 8 Each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclyl group, or a combination thereof,
R 19 to R 24 Each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, substituted or unsubstituted silyl, substituted or unsubstituted amine, halogen, cyano, or a combination thereof,
R 19 to R 24 Each independently being present or adjacent groups thereof are linked to each other to provide a substituted or unsubstituted aliphatic monocyclic ring, a substituted or unsubstituted aliphatic polycyclic ring, a substituted or unsubstituted aromatic monocyclic ring, a substituted or unsubstituted aromatic-forming polycyclic ring, a substituted or unsubstituted heteroaromatic monocyclic ring, or a substituted or unsubstituted heteroaromatic polycyclic ring, and
when R is 19 To R 24 Each independently of the other, R 19 To R 24 Is a substituted or unsubstituted C10 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group.
10. The composition for an organic photoelectric device according to claim 9, wherein,
the second compound is represented by chemical formula 2-ib:
[ chemical formula 2-IB ]
Wherein, in the chemical formula 2-IB,
Z 1 、Z 3 and Z 5 Each of which is independently N or CH,
Z 1 、Z 3 and Z 5 At least two of which are N,
L 4 、L 6 and L 8 Each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclyl group, or a combination thereof,
R 22 and R 24 Each independently substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
R 25 to R 32 Each independently is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, halogen, cyano, or a combination thereof, and
R 25 to R 32 Each independently is present or adjacent groups thereof are linked to each other to provide a substituted or unsubstituted aliphatic monocyclic ring, a substituted or unsubstituted aliphatic polycyclic ring, a substituted or unsubstituted aromatic monocyclic ring, a substituted or unsubstituted aromatic-forming polycyclic ring, a substituted or unsubstituted heteroaromatic monocyclic ring, or a substituted or unsubstituted heteroaromatic polycyclic ring.
11. The composition for an organic photoelectric device according to claim 10, wherein,
the second compound is represented by any one of chemical formulas 2-IB-1 to 2-IB-6:
wherein, in chemical formula 2-IB-1 to chemical formula 2-IB-6,
X 4 is O, S CR j R k Or N-L 14 -Ar 3 ，
n15 is an integer of 1 to 4,
L 4 、L 6 、L 8 and L 14 Each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclyl group, or a combination thereof,
R j and R k Each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,
Ar 3 、R 22 and R 24 Each independently is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclyl group, or a combination thereof, and
R 25 to R 32 And R 50 Each independently is hydrogen, deuterium, substituted or unsubstitutedA substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof.
12. An organic photoelectric device comprises
An anode and a cathode facing each other,
at least one organic layer between the anode and the cathode,
wherein the organic layer comprises the compound for an organic photoelectric device according to any one of claims 1 to 8 or the composition for an organic photoelectric device according to any one of claims 9 to 11.
13. The organic photoelectric device according to claim 12,
the organic layer includes a light emitting layer, and
the light-emitting layer includes the composition for an organic photoelectric device.
14. The organic optoelectronic device of claim 12,
the organic layer includes a light-emitting layer, a hole transport layer between the anode and the cathode, and a hole transport auxiliary layer between the light-emitting layer and the hole transport layer, and
the hole transport auxiliary layer includes the compound for an organic photoelectric device.
15. A display device comprising the organic photoelectric device according to claim 12.
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| KR10-2021-0088621 | 2021-07-06 | ||
| KR1020220059688A KR20220156454A (en) | 2021-05-18 | 2022-05-16 | Composition for organic optoelectronic device, organic optoelectronic device and display device |
| KR1020220059689A KR20230007931A (en) | 2021-07-06 | 2022-05-16 | Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display device |
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