CN111095586B - Organic photoelectric device and display device - Google Patents
Organic photoelectric device and display device Download PDFInfo
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- CN111095586B CN111095586B CN201880060459.7A CN201880060459A CN111095586B CN 111095586 B CN111095586 B CN 111095586B CN 201880060459 A CN201880060459 A CN 201880060459A CN 111095586 B CN111095586 B CN 111095586B
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- SWJBITNFDYHWBU-UHFFFAOYSA-N [I].[I] Chemical compound [I].[I] SWJBITNFDYHWBU-UHFFFAOYSA-N 0.000 description 1
- 125000003275 alpha amino acid group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000005566 carbazolylene group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- PJVZQNVOUCOJGE-CALCHBBNSA-N chembl289853 Chemical class N1([C@H]2CC[C@H](O2)N2[C]3C=CC=CC3=C3C2=C11)C2=CC=C[CH]C2=C1C1=C3C(=O)N(C)C1=O PJVZQNVOUCOJGE-CALCHBBNSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- JOTOPCOJPUYXPE-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1.ClC1=CC=CC=C1 JOTOPCOJPUYXPE-UHFFFAOYSA-N 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- JQOAQUXIUNVRQW-UHFFFAOYSA-N hexane Chemical compound CCCCCC.CCCCCC JQOAQUXIUNVRQW-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 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
- 230000003993 interaction Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- JWQLJPBJNSPKSG-UHFFFAOYSA-M magnesium;phenylbenzene;bromide Chemical compound [Mg+2].[Br-].C1=CC=CC=C1C1=CC=[C-]C=C1 JWQLJPBJNSPKSG-UHFFFAOYSA-M 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 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
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229930184652 p-Terphenyl Natural products 0.000 description 1
- YNEMPXKRLPZFAX-UHFFFAOYSA-N p-Terphenyl A Natural products COC1=CC(C=2C=CC(O)=CC=2)=C(OC)C(O)=C1C1=CC=C(O)C=C1 YNEMPXKRLPZFAX-UHFFFAOYSA-N 0.000 description 1
- 150000002979 perylenes Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 229910052697 platinum Inorganic materials 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
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 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
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 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
- 238000005406 washing Methods 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C—CHEMISTRY; METALLURGY
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- Electroluminescent Light Sources (AREA)
Abstract
An organic optoelectronic device and a display device including the same are disclosed, the organic optoelectronic device including: an anode and a cathode facing each other; a light-emitting layer disposed between the anode and the cathode; a hole transport layer disposed between the anode and the light emitting layer; and a hole transport auxiliary layer disposed between the light emitting layer and the hole transport layer, wherein the light emitting layer includes a first compound represented by chemical formula 1 and a second compound represented by a combination of chemical formula 2 and chemical formula 3, and the hole transport auxiliary layer includes a third compound represented by chemical formula 4. Chemical formulas 1 to 4 are the same as provided in the specification.
Description
Technical Field
The invention discloses an organic photoelectric device and a display device.
Background
An organic optoelectronic device (organic photodiode (organic optoelectric diode)) is a device that converts electrical energy into optical energy and vice versa.
Organic optoelectronic devices can be classified according to their driving principles as follows. One is an optoelectronic device in which excitons (exiton) are generated from light energy, the excitons are separated into electrons and holes and transferred to different electrodes to generate electric energy, and the other is a light emitting device in which a voltage or current is supplied to the electrodes to generate light energy from the electric energy.
Examples of the organic photoelectric device may be an organic photoelectric device (organic photoelectric device), an organic light emitting diode, an organic solar cell, and an organic photosensitive drum (organic photo conductor drum).
Among them, organic light emitting diodes (organic light emitting diode, OLED) have recently attracted attention due to an increasing demand for flat panel displays (flat panel display device). The organic light emitting diode converts electric energy into light by applying a current to the organic light emitting material, and the efficiency of the organic light emitting diode may be affected by the organic material disposed between the electrodes.
Disclosure of Invention
Technical problem
An embodiment provides an organic photoelectric device capable of improving power efficiency by reducing a driving voltage.
Another embodiment provides a display device including the organic photoelectric device.
Technical proposal
According to one embodiment, an organic optoelectronic device includes: an anode and a cathode facing each other; a light-emitting layer disposed between the anode and the cathode; a hole transport layer disposed between the anode and the light emitting layer; and a hole transport auxiliary layer disposed between the light emitting layer and the hole transport layer, wherein the light emitting layer includes a first compound represented by chemical formula 1 and a second compound represented by a combination of chemical formula 2 and chemical formula 3, and the hole transport auxiliary layer includes a third compound represented by chemical formula 4.
[ chemical formula 1]
In the chemical formula 1, the chemical formula is shown in the drawing,
X 1 is either O or S, and is preferably selected from the group consisting of,
Z 1 to Z 3 Independently N or CR a ，
Z 1 To Z 3 At least two of which are N,
Ar 1 ar and Ar 2 Independently hydrogen, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
L 1 to L 3 Independently a single bond, a substituted or unsubstituted C6 to C30 arylene, a divalent substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
R 1 to R 5 R is as follows a Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or a combination thereof,
R 1 to R 3 Independently present or R 1 To R 3 Two adjacent of them are combined to form a ring, and
R 4 r is R 5 Independently or fused to each other to form a ring,
wherein, in chemical formula 2 or chemical formula 3,
Y 1 y and Y 2 Independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,
A 1 a is a 2 Independently a substituted or unsubstituted C6 to C30 aryl,
two adjacent ones of chemical formula 2 are bonded to two of chemical formula 3, and the remaining two of chemical formula 2 are CR, respectively b CR (computed tomography) c ，
R 20 To R 23 、R b R is R c Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, or a combination thereof,
R 20 r is R 21 Independently present or condensed with each other to form a ring, and
R 22 r is R 23 Independently or fused to each other to form a ring,
[ chemical formula 4]
Wherein, in the chemical formula 4,
L 4 to L 9 Independently a single bond, a substituted or unsubstituted C6 to C30 arylene, a divalent substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
R 50 to R 55 Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or a combination thereof,
R 50 r is R 51 Independently or fused to each other to form a ring,
R 52 r is R 53 Independently present or condensed with each other to form a ring, and
R 54 r is R 55 Independently or fused to each other to form a ring.
According to another embodiment, there is provided a display device including the organic photoelectric device.
Advantageous effects
An organic photoelectric device having high efficiency and long life can be achieved.
Drawings
Fig. 1 is a schematic cross-sectional view of an organic optoelectronic device according to an embodiment.
Symbol description
300: organic light emitting diode
105: organic layer
110: anode
120: cathode electrode
130: light-emitting layer
141: hole transport layer
142: hole transport auxiliary layer
Detailed Description
Hereinafter, embodiments of the present invention are described in detail. However, the embodiments are exemplary, the invention is not limited thereto, and the invention is defined by the scope of the claims.
In the present specification, "substituted" means that at least one hydrogen of a substituent or compound is replaced by: 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 alkylsilane, C6 to C30 arylsilane, 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 alkylsilane, C6 to C30 arylsilane, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, or C2 to C30 heteroaryl. In addition, 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 C2 to C30 heteroaryl group. In addition, 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, pyridyl, quinolinyl, isoquinolinyl, dibenzofuranyl, dibenzothienyl, or carbazolyl. In addition, 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, dibenzofuranyl, or dibenzothiophenyl. In addition, in specific examples of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced with deuterium, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, naphthyl, triphenyl, dibenzofuranyl, or dibenzothiophenyl.
In the present specification, when definition is not otherwise provided, "hetero" means that one to three hetero atoms selected from N, O, S, P and Si are contained in one functional group and the rest is carbon.
In the present specification, "aryl" refers to a group comprising at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p-orbitals that form a conjugate (conjugation), e.g., phenyl, naphthyl, etc., two or more hydrocarbon aromatic moieties may be linked by sigma bonds, and may be, e.g., biphenyl, terphenyl, tetrabiphenyl, etc., and two or more hydrocarbon aromatic moieties are directly or indirectly fused (fused) to provide a non-aromatic fused ring, e.g., a fluorene group (fluorine group).
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 (heterocyclic group)" 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 heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group may contain one or more heteroatoms.
For example, "heteroaryl" may refer to an aryl group comprising at least one heteroatom selected from N, O, S, P and Si in place of carbon (C). Two or more heteroaryl groups are directly linked by a sigma linkage, or when a C2 to C60 heteroaryl group comprises two or more rings, the two or more rings may be fused. When heteroaryl is a fused ring, each ring may contain 1 to 3 heteroatoms.
Specific examples of the heterocyclic group may be pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl and the like.
More specifically, the substituted or unsubstituted C6 to C30 aryl and/or substituted or unsubstituted C2 to C30 heterocyclyl may be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthryl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted fused tetraphenyl (naphthacenyl group), a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted p-terphenyl A group (chrysenyl group), a substituted or unsubstituted biphenylenyl group, a substituted or unsubstituted perylene group (perylenyl group), a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group (indenyl group), a substituted or unsubstituted furanyl group, 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 pyridinyl 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 Substituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl (acridinyl group), substituted or unsubstituted porphyrazinyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, or a combination thereof, but are not limited thereto.
In this specification, the hole feature refers to an ability to donate (date) electrons to form holes when an electric field (electric field) is applied, and holes formed in the anode may be easily injected into the light emitting layer and holes formed in the light emitting layer may be easily transported to the anode and in the light emitting layer due to a conduction feature according to a highest occupied molecular orbital (highest occupied molecular orbital, HOMO) energy 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 the light emitting layer and electrons formed in the light emitting layer may be easily transferred into the cathode and transferred in the light emitting layer due to a conductive characteristic according to a lowest unoccupied molecular orbital (lowest unoccupied molecular orbital, LUMO) energy level.
Hereinafter, an organic optoelectronic device according to an embodiment is described.
The organic photoelectric device may be any device that converts electric energy into light energy or 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.
Here, an organic light emitting diode is described as an example of an organic optoelectronic device, but the present invention is not limited thereto, and may be applied to other organic optoelectronic devices in the same manner.
In the drawings, the thickness of layers, films, plates, regions, etc. are exaggerated for clarity. Like reference numerals designate like elements throughout the specification. It will be understood that when an element (e.g., a layer, film, region, or substrate) is referred to as being "on" another element, it can be directly on the other element or intervening elements may also be present. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.
Fig. 1 is a schematic cross-sectional view of an organic optoelectronic device according to an embodiment.
Referring to fig. 1, an organic light emitting diode 300 according to an embodiment includes an anode 110 and a cathode 120 facing each other, and an organic layer 105 disposed between the anode 110 and the cathode 120, wherein the organic layer 105 includes a light emitting layer 130, a hole transport auxiliary layer 142, and a hole transport layer 141.
Anode 110 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. Anode 110 may be, for example, metallic nickel, platinum, vanadium, chromium, copper, zinc, gold, etc., or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), indium zinc oxide (indium zinc oxide, IZO), and the like; combinations of metals with oxides, e.g. ZnO with Al or SnO 2 And Sb; conductive polymers such as poly (3-methylthiophene), poly (3, 4- (ethylene-1, 2-dioxythiophene) (poly (3, 4- (ehtylene-1, 2-dioxy) thiophen): PEDOT), polypyrrole and polyaniline, but are not limited thereto.
The cathode 120 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 120 may be, for example, a metal or alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum silver, tin, lead, cesium, barium, and the like; multi-layer (layer) structural materials, e.g. LiF/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 and/Ca, but is not limited thereto.
The light emitting layer 130 is disposed between the anode 110 and the cathode 120, and includes a plurality of hosts (host) and at least one dopant (dopant).
The light emitting layer 130 may include a first compound having a relatively strong electron characteristic and a second compound having a relatively strong hole characteristic as a host.
The first compound having relatively strong electronic characteristics may be represented by chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, the chemical formula is shown in the drawing,
X 1 is either O or S, and is preferably selected from the group consisting of,
Z 1 to Z 3 Independently N or CR a ，
Z 1 To Z 3 At least two of which are N,
Ar 1 ar and Ar 2 Independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
L 1 to L 3 Independently a single bond, a substituted or unsubstituted C6 to C30 arylene, a divalent substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
R 1 to R 5 R is as follows a Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or a combination thereof,
R 1 to R 3 Independently present or R 1 To R 3 Two adjacent of them are combined to form a ring, and
R 4 r is R 5 Independently or fused to each other to form a ring.
The first compound includes a dibenzofuran or dibenzothiophene moiety and a nitrogen-containing six-membered ring moiety, and thus can increase the planarity of the molecular structure while effectively expanding the LUMO band. Accordingly, the first compound may have a structure that is easy to accept electrons when an electric field is applied to an organic photoelectric device manufactured by using the first compound, and thus may reduce a driving voltage of the organic photoelectric device. In addition, as the LUMO band is enlarged, the electron stability is also increased, and thus the lifetime of the organic photoelectric device can be improved.
For example, Z 1 To Z 3 Both of which may be nitrogen.
For example, Z 1 Z is as follows 2 Can be nitrogen, and Z 3 Can be CR a 。
For example, Z 2 Z is as follows 3 Can be nitrogen, and Z 1 Can be CR a 。
For example, Z 1 Z is as follows 3 Can be nitrogen, and Z 2 Can be CR a 。
For example, Z 1 To Z 3 May be nitrogen.
For example, ar 1 Ar and Ar 2 May independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenylyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or a combination thereof.
For example, ar 1 Ar and Ar 2 May independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, or substituted or unsubstituted fluorenyl.
For example, ar 1 Ar and Ar 2 May independently be one of the substituted or unsubstituted groups of group 1.
Group 1
For example, L 1 To L 3 May independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazole group, or a substituted or unsubstituted fluorenylene group. For example, L 1 May be a single bond, a substituted or unsubstituted m-phenylene group, a substituted or unsubstituted p-phenylene group, a substituted or unsubstituted m-biphenylene group, a substituted or unsubstituted p-biphenylene group, or a substituted or unsubstituted naphthylene group. Herein, "substituted" means that at least one hydrogen is replaced with deuterium, a C1 to C20 alkyl group, a C6 to C12 aryl group, or a cyano group.
For example, L 3 May be a single bond.
In one embodiment of the invention, when L 1 Ar is a single bond 1 Not hydrogen and deuterium, and when L 2 Ar is a single bond 2 Not hydrogen or deuterium.
For example, the first compound may be represented by chemical formula 1A.
[ chemical formula 1A ]
In chemical formula 1A, X 1 、Z 1 To Z 3 、Ar 1 、Ar 2 、L 2 、L 3 R is R 1 To R 5 As described above.
In the chemical formula 1A, a compound represented by the formula 1A,
R p 、R q 、R r r is as follows s Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or a combination thereof,
R p r is R q Independently or fused to each other to form a ring,
R r r is R s Independently present or condensed with each other to form a ring, and
n1 is an integer from 0 to 2.
For example, R p 、R q 、R r R is as follows s May independently be hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, cyano, or a combination thereof.
The first compound represented by chemical formula 1A includes at least one meta (meta) bonded arylene group, which can inhibit interactions with neighboring molecules and reduce crystallization (crystallization) due to steric hindrance (steric) characteristics, and thus further improve efficiency and lifetime characteristics of the organic photoelectric device.
In addition, the first compound includes a kinked moiety (e.g., meta-bonded arylene) and thus has a higher glass transition temperature (glass transition temperature, tg), and degradation of the first compound may be inhibited during the fabrication and/or operation of the organic optoelectronic device and thus thermal stability of the first compound may be increased.
For example, the first compound may be represented by one of chemical formulas 1A-1 to 1A-3, but is not limited thereto.
In chemical formulas 1A-1 to 1A-3, X 1 、Z 1 To Z 3 、Ar 1 、Ar 2 、L 2 、L 3 、R 1 To R 5 、R p 、R q 、R r 、R s And n1 is the same as described above.
In chemical formulas 1A-1 to 1A-3,
X 2 is either O or S, and is preferably selected from the group consisting of,
Z 4 to Z 6 Independently N or CR a ，
Z 4 To Z 6 At least one of which is N,
R 6 to R 15 Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or a combination thereof,
R 6 r is R 7 Independently present or condensed with each other to form a ring, and
R 9 to R 13 Independently present or R 9 To R 13 Which combine to form a ring.
For example, Z 4 To Z 6 At least one of which may be nitrogen.
For example, Z 4 To Z 6 Both of which may be nitrogen.
For example, Z 4 Z is as follows 5 Can be nitrogen, and Z 6 Can be CR a 。
For example, Z 4 Z is as follows 6 Can be nitrogen, and Z 5 Can be CR a 。
For example, Z 5 Z is as follows 6 Can be nitrogen, and Z 4 Can be CR a 。
For example, Z 4 To Z 6 May be nitrogen.
By way of exampleIn other words, ar 1 、Ar 2 、R 14 R is as follows 15 May independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, or substituted or unsubstituted fluorenyl.
For example, R p 、R q 、R r R is as follows s May independently be hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, cyano, or a combination thereof.
The first compound may be, for example, one of the compounds of group 2, but is not limited thereto.
Group 2
The second compound having a relatively strong hole characteristic may be represented by a combination of chemical formula 2 and chemical formula 3.
In the chemical formula 2 or the chemical formula 3,
Y 1 y and Y 2 Independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,
A 1 a is a 2 Independently a substituted or unsubstituted C6 to C30 aryl,
two adjacent ones of chemical formula 2 are bonded to two of chemical formula 3, and the remaining two of chemical formula 2 are CR, respectively b CR (computed tomography) c ，
R 20 To R 23 、R b R is R c Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, or a combination thereof,
R 20 r is R 21 Independently present or condensed with each other to form a ring, and
R 22 r is R 23 Independently of each other or present in each otherFused to form a ring.
The second compound may be an aryl-substituted indolocarbazole compound, and may have excellent hole characteristics. The second compound is included together with the first compound, and thus the balance between electrons and holes in the light emitting layer 130 can be increased, and an organic photoelectric device having a long lifetime can be achieved.
For example, Y 1 Y and Y 2 May independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, or a substituted or unsubstituted fluorenylene group.
For example, Y 1 Y and Y 2 May independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.
For example, Y 1 Y and Y 2 May independently be a single bond, a substituted or unsubstituted m-phenylene, a substituted or unsubstituted p-phenylene, a substituted or unsubstituted m-biphenylene, a substituted or unsubstituted p-biphenylene, or a substituted or unsubstituted naphthylene. Wherein "substituted" means that at least one hydrogen is replaced with deuterium, a C1 to C20 alkyl group, a C6 to C12 aryl group, or a cyano group.
For example, A 1 A is a 2 May 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 anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted ditolylphenyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof.
For example, A 1 A is a 2 May independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.
The second compound may be represented by one of chemical formulas 2-a to 2-E depending on a bonding position between chemical formula 2 and chemical formula 3.
In chemical formulas 2-A to 2-E, Y 1 、Y 2 、A 1 、A 2 、R 20 To R 23 、R b R is R c As described above.
In one embodiment of the present invention, the second compound may be selected from chemical formula 2-a or chemical formula 2-E according to the driving voltage effect, and may specifically be chemical formula 2-a.
The second compound may be, for example, one of the compounds of group 3, but is not limited thereto.
Group 3
In one embodiment of the present invention, the first compound may be represented by chemical formula 1A, and the second compound may be represented by chemical formula 2-a.
In one embodiment of the invention, the first and second compounds may be included in a weight ratio of about 1:99 to 99:1, such as about 10:90 to 90:10, about 20:80 to 80:20, about 30:70 to 70:30, about 40:60 to 60:40, or about 50:50.
The body may further comprise at least one compound other than the first compound and the second compound.
The light emitting layer 130 may further include a dopant. The dopant may be a red dopant, a green dopant, or a blue dopant.
The dopant is mixed with the host in a small amount to cause luminescence, and may be generally an organic compound or a metal complex (e.g., al) that emits fluorescence by singlet excitation (singlet excitation) or a material that emits luminescence by multiple excitation (multiple excitation) from a ground state to a triplet state or more (e.g., a metal complex). The dopant may be, for example, an inorganic compound, an organic compound, or an organic/inorganic compound, and one or more kinds thereof may be used.
Examples of dopants may be organometallic compounds comprising Ir, pt, os, ti, zr, hf, eu, tb, tm, fe, co, ni, ru, rh, pd or combinations thereof. The dopant may be, for example, a compound represented by chemical formula Z, but is not limited thereto.
[ chemical formula Z ]
L 2 MX
In formula Z, M is a metal, and L and X are the same or different and are ligands (ligands) that form a complex compound with M.
M may be, for example, 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 (bidentate ligands).
The hole transport auxiliary layer 142 may be disposed between the light emitting layer 130 and a hole transport layer 141 to be described later, and may particularly contact the light emitting layer 130. The hole transport auxiliary layer 142 may precisely control hole mobility (hole mobility) at an interface between the light emitting layer 130 and the hole transport layer 141 by contacting the light emitting layer 130. The hole transport auxiliary layer 142 may include a plurality of layers.
The hole transport auxiliary layer 142 may include, for example, a third compound represented by chemical formula 4.
[ chemical formula 4]
In the chemical formula 4, the chemical formula is shown in the drawing,
L 4 to L 9 Independently a single bond, a substituted or unsubstituted C6 to C30 arylene, a divalent substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
R 50 To R 55 Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or a combination thereof,
R 50 r is R 51 Independently or fused to each other to form a ring,
R 52 r is R 53 Independently present or condensed with each other to form a ring, and
R 54 r is R 55 Independently or fused to each other to form a ring.
The third compound has a high HOMO energy level, and thus has sufficient hole injection characteristics. Accordingly, the third compound is applied to the hole transport auxiliary layer 142, and thus hole mobility at the interface between the light emitting layer 130 and the hole transport layer 141 can be effectively improved, and driving voltage of the organic photoelectric device can be effectively reduced.
For example, L 4 To L 9 Can be independently a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted phenyleneNaphthyl, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted carbazolylene, or substituted or unsubstituted fluorenylene. For example, L 4 To L 9 May independently be a single bond, a substituted or unsubstituted m-phenylene, a substituted or unsubstituted p-phenylene, a substituted or unsubstituted m-biphenylene, a substituted or unsubstituted p-biphenylene, or a substituted or unsubstituted naphthylene. Herein, "substituted" means that at least one hydrogen is replaced with deuterium, a C1 to C20 alkyl group, a C6 to C12 aryl group, or a cyano group.
For example, R 50 To R 55 May independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C3 to C30 heterocyclic group.
For example, R 50 To R 55 May independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, or substituted or unsubstituted fluorenyl.
For example, R 50 To R 55 May independently be a substituted or unsubstituted C6 to C30 aryl group, or may, for example, 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 anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenylyl group, or a combination thereof.
For example, R 50 To R 55 At least one of which may be a substituted or unsubstituted C3 to C30 heterocyclyl.
For example, R 50 To R 55 At least one of them may be a group represented by chemical formula a.
[ chemical formula A ]
In the chemical formula a, the amino acid sequence of the formula a,
X 3 is either O or S, and is preferably selected from the group consisting of,
R 60 to R 67 Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or a combination thereof, or with L of formula 4 4 To L 9 A group attached to one of them, an
R 60 To R 67 Independently present or R 60 To R 67 Which combine to form a ring.
For example, R 50 To R 55 One of them may be a group represented by formula A, and R 50 To R 55 The remainder of (C) may independently be a substituted or unsubstituted C6 to C30 aryl group.
For example, R 50 To R 55 Two of them may be groups represented by formula A, and R 50 To R 55 The remainder of (C) may independently be a substituted or unsubstituted C6 to C30 aryl group.
For example, R 50 To R 55 Three of (a) may be groups represented by formula A, and R 50 To R 55 The remainder of (C) may independently be a substituted or unsubstituted C6 to C30 aryl group.
The third compound may be, for example, one of the compounds of group 4, but is not limited thereto.
Group 4
The hole transport layer 141 is disposed between the anode 110 and the light emitting layer 130, and may facilitate easy transport of holes from the anode 110 into the light emitting layer 130. For example, the hole transport layer 141 may include a material having a HOMO energy level between a work function of a conductor forming the anode 110 and a HOMO energy level of a material forming the light emitting layer 130.
The hole transport layer 141 may include, for example, an amine derivative.
The hole transport layer 141 may include, for example, a compound represented by chemical formula 5, but is not limited thereto.
[ chemical formula 5]
In the chemical formula 5, the chemical formula is shown in the drawing,
R 118 to R 121 Independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
R 118 r is R 119 Independently or fused to each other to form a ring,
R 120 r is R 121 Independently or fused to each other to form a ring,
Ar 10 to Ar 12 Independently is a substituted or unsubstituted C6 to C30 aryl or a substituted or unsubstituted C2 to C30 heterocyclyl, and
L 10 to L 13 Independently a single bond, a substituted or unsubstituted C6 to C30 arylene, a divalent substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof.
For example, ar 10 May be a substituted or unsubstituted C6 to C30 aryl group, and for example Ar 10 May be a substituted or unsubstituted phenyl group orSubstituted or unsubstituted biphenyl.
For example, ar 11 Ar and Ar 12 May independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted bifluorenyl group, a substituted or unsubstituted ditriarenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a combination thereof.
The compound represented by chemical formula 5 may be, for example, one of the compounds of group 5, but is not limited thereto.
Group 5
The organic layer 105 may further include a hole injection layer, an electron blocking layer, an electron transport layer, an electron injection layer, and/or a hole blocking layer (not shown) in addition to the light emitting layer 130, the hole transport auxiliary layer 142, and the hole transport layer 141.
The organic light emitting diode 300 may be manufactured by: an anode or a cathode is formed on a substrate, an organic layer is formed using a dry film forming method or a solution process such as evaporation (evapration), sputtering (sputtering), plasma plating (plasma plating), and ion plating (ion plating), and a cathode or an anode is formed on the organic layer.
The organic photoelectric device may be applied to a display device. For example, the organic light emitting diode may be applied to an Organic Light Emitting Diode (OLED) display.
Best mode
Hereinafter, embodiments are described in more detail with reference to examples. However, these examples are exemplary, and the scope of the invention is not limited thereto.
Synthesis example
Synthesis example 1: synthesis of Compound B-24
[ reaction scheme 1]
a) Synthesis of intermediate B-24-1
15 g (81.34 mmol) of cyanuric chloride (cyanuric chloride) are dissolved in 200 mL of anhydrous tetrahydrofuran in a 500 mL (mL) round bottom flask, 1 equivalent of 4-biphenylmagnesium bromide solution (0.5M tetrahydrofuran) is added dropwise thereto under nitrogen atmosphere at 0 ℃ and the mixture is slowly warmed to room temperature. The reaction solution was stirred at room temperature for 1 hour, and 500 ml of ice water was added thereto to separate the layers. The organic layer was separated therefrom, treated with anhydrous magnesium sulfate and concentrated. The concentrated residue was recrystallized from tetrahydrofuran and methanol to obtain 17.2 g of intermediate B-24-1.
b) Synthesis of intermediate B-24-2
17.2 g (56.9 mmol) of intermediate B-24-1 was added to 200 ml of tetrahydrofuran and 100 ml of distilled water in a 500 ml round bottom flask, 2 equivalents of dibenzofuran-3-boronic acid (chemical abstract service (Chemical Abstracts Service, cas): 395087-89-5), 0.03 equivalent of tetrakis-triphenylphosphine palladium (tetrakistriphenylphosphine palladium) and 2 equivalents of potassium carbonate were added thereto, and the mixture was heated and refluxed under nitrogen atmosphere. After 18 hours, the reaction solution was cooled, and the solid precipitated therein was filtered and washed with 500 ml of water. The solid was recrystallized from 500 ml of monochlorobenzene (monochlorobenzene) to give 13.05 g of intermediate B-24-2.
c) Synthesis of Compound B-24
Compound B-24 was synthesized according to the same method as B) using intermediate B-24-2 and 1.1 equivalent of B- [1,1':4',1"-Terphenyl ] -3-yl boronic acid (B- [1,1':4',1" -terpenyl ] -3-yl carboxylic acid).
Liquid chromatography (liquid chromatography, LC)/Mass Spectrometry (MS) calculated (calculated for): exact Mass of C45H29N3O (Exact Mass): 627.2311 Experimental value (found for) 628.24[ M+H ]
Synthesis example 2: synthesis of Compound B-71
[ reaction scheme 2]
a) Synthesis of intermediate B-71-1
14.06 g (56.90 mmol) of 3-bromo-dibenzofuran, 200 ml of tetrahydrofuran and 100 ml of distilled water were placed in a 500 ml round bottom flask, 1 equivalent of 3' -chloro-phenylboronic acid, 0.03 equivalent of tetrakis-triphenylphosphine palladium and 2 equivalents of potassium carbonate were added thereto, and the mixture was heated and refluxed under nitrogen atmosphere. After 18 hours, the reaction solution was cooled, and the solid precipitated therein was filtered and washed with 500 ml of water. The solid was recrystallized from 500 ml of monochlorobenzene to obtain 12.05 g of intermediate B-71-1. (yield 76%)
b) Synthesis of intermediate B-71-2
24.53 g (88.02 mmol) of intermediate B-71-1 and 250 ml of Dimethylformamide (DMF) were placed in a 500 ml round bottom flask, to which 0.05 equivalent of dichlorodiphenylphosphino ferrocene palladium (dichlorodiphenylphosphinoferrocene palladium), 1.2 equivalent of dipyridyl diboron (bispinacolato diboron) and 2 equivalent of potassium acetate were added, and the mixture was heated under nitrogen atmosphere and refluxed for 18 hours. The reaction solution was cooled and added dropwise to 1 liter (L) of water. The solid obtained therefrom was dissolved in boiling toluene, treated with activated carbon, and filtered through silica gel, and the filtrate obtained therefrom was concentrated. The concentrated solid was stirred with a small amount of hexane and filtered to obtain 22.81 g of intermediate B-71-2. (yield 70%)
c) Synthesis of Compound B-71
Compound B-71 was synthesized by the same method as B) of synthesis example 1 by using the intermediates B-71-2 and 2,4-Bis ([ 1,1'-biphenyl ] -4-yl) -6-chloro-1,3,5-triazine (2, 4-Bis ([ 1,1' -biphen ] -4-yl) -6-chloro-1,3, 5-triazine) in amounts of 1.0 equivalent, respectively.
LC/MS calculated (calculated for): exact Mass of C45H29N3O (Exact Mass): 627.2311 Experimental value (found for) 628.25[ M+H ]
Synthesis example 3: synthesis of Compound B-20
[ reaction scheme 3]
a) Synthesis of intermediate B-20-1
22.6 g (100 mmol) of 2, 4-dichloro-6-phenyltriazine together with 100 ml of tetrahydrofuran, 100 ml of toluene and 100 ml of distilled water were placed in a 500 ml round-bottomed flask, 0.9 equivalent of dibenzofuran-3-boronic acid (CAS No. 395087-89-5), 0.03 equivalent of tetrakis-triphenylphosphine palladium and 2 equivalents of potassium carbonate were added thereto, and the mixture was heated and refluxed under a nitrogen atmosphere. After 6 hours, the reaction solution was cooled, and the organic layer obtained after removing the aqueous layer was dried under reduced pressure. The solid obtained therefrom was washed with water and hexane, and recrystallized from 200 ml of toluene to obtain 21.4 g of intermediate B-20-1 (yield 60%).
b) Synthesis of Compound B-20
According to the same manner as in B) of Synthesis example 1, intermediate B-20-1 and 1.1 equivalent of (5 '-phenyl [1,1':3', 1' -terphenyl ] -4-yl) -boronic acid were used (CAS number: 491612-72-7) Synthesis of Compound B-20.
LC/MS calculated (calculated for): exact Mass of C45H29N3O (Exact Mass): 627.2311 Experimental value (found for) 628.24[ M+H ]
Synthesis example 4: synthesis of Compound B-124
[ reaction scheme 4]
a) Synthesis of intermediate B-124-1
Synthesis of intermediate B-124-1 according to Synthesis example 1B) using 1-bromo-3-chloro-5-phenylbenzene and 1.1 equivalent of biphenyl-4-boronic acid. Here, the product obtained therefrom was purified with hexane via flash column (flash column) instead of recrystallization.
b) Synthesis of intermediate B-124-2
30 g (88.02 mmol) of intermediate B-124-1 was added to 250 ml of Dimethylformamide (DMF) in a 500 ml round bottom flask, 0.05 equivalent of dichlorodiphenylphosphino ferrocene palladium), 1.2 equivalent of dipyruvyldiboron and 2 equivalents of potassium acetate were added thereto, and the mixture was heated under nitrogen atmosphere and refluxed for 18 hours. The reaction solution was cooled and added dropwise to 1 liter of water to obtain a solid. The solid was dissolved in boiling toluene, treated with activated carbon, filtered through a silica gel, and the filtrate was concentrated. The concentrated solid was stirred with a small amount of hexane and filtered to obtain 28.5 g of intermediate B-124-2 (yield 70%).
c) Synthesis of Compound B-124
Compound B-124 was synthesized according to the same method as in B) of Synthesis example 1, using intermediate B-124-2 and intermediate B-17-1 in amounts of 1.0 equivalent, respectively.
LC/MS calculated (calculated for): exact Mass of C45H29N3O (Exact Mass): 627.2311 Experimental value (found for) 628.22[ M+H ]
Synthesis example 5: synthesis of Compound B-3
[ reaction scheme 5]
a) Synthesis of intermediate B-3-1
Magnesium (7.86 g, 323 mmol) and iodine (iodine) (1.64 g, 6.46 mmol) were stirred with 0.1 liter Tetrahydrofuran (THF) under nitrogen for 30 minutes and exceeded at 0 °c1-bromo-3,5-diphenylbenzene (1-bromo-3, 5-diphenobenzene) (100 g, 323 mmol) dissolved in 0.3 l tetrahydrofuran was slowly added dropwise thereto over 30 minutes. The obtained mixed solution was slowly dropped into 64.5 g (350 mmol) of a cyanuric chloride solution dissolved in 0.5 l of Tetrahydrofuran (THF) at 0 ℃ for 30 minutes. When the reaction was completed, water was added to the reaction solution, and an extract was obtained with Dichloromethane (DCM) using anhydrous MgSO 4 After removing moisture therefrom, filtration was performed, and concentration was performed under reduced pressure. The residue obtained therefrom was separated via flash column chromatography (flash column chromatography) to obtain intermediate B-3-1 (79.4 g, 65%).
b) Synthesis of Compound B-3
Compound B-3 was synthesized according to the same method as in B) of Synthesis example 1, using intermediate B-3-1.
LC/MS calculated (calculated for): exact Mass (Exact Mass) of C45H27N3O 2: 641.2103 Experimental value (found for) 642.21[ M+H ]
Synthesis example 6: synthesis of Compound HC-28
[ reaction scheme 6]
a) Synthesis of intermediate HC-28-1
Intermediate a (30 g, 121.9 mmol), 1 equivalent of 4,4', 5',5' -octamethyl-2,2' -bis (1, 3, 2-dioxapentaborane) (4, 4', 5',5' -octamethyl-2,2' -bi (1, 3, 2-dioxablonane)), 2 equivalents of potassium acetate, 0.03 equivalent of 1,1' -bis (diphenylphosphino) ferrocene-palladium (ii) dichloride and 0.2 equivalent of tricyclohexylphosphine were added to 300 ml of N, N-dimethylformamide in a 500 ml flask, and the mixture was stirred at 130 ℃ for 12 hours. When the reaction was completed, the reaction solution was extracted with water and EA to obtain an organic layer, and the organic layer was concentrated after removing moisture therefrom with magnesium sulfate, and then purified via column chromatography to obtain intermediate HC-28-1 (29.66 g, yield 83%).
b) Synthesis of intermediate HC-28-2
29.66 g (0.4 mol) of intermediate HC-28-1, 2 equivalents of intermediate B (1-bromo-20 nitrobenzene), 2 equivalents of potassium carbonate and 0.02 equivalents of tetrakis (triphenylphosphine) palladium (0) were added to 200 ml of 1, 4-dioxane and 100 ml of water in a 500 ml flask, and the mixture was heated under a nitrogen stream at 90℃for 16 hours. After the reaction solvent was removed therefrom, the resultant obtained therefrom was dissolved in methylene chloride, filtered through silica gel/celite, and recrystallized with methanol after an appropriate amount of organic solvent was removed therefrom to obtain solid intermediate HC-28-2 (16.92 g, yield 58%).
c) Synthesis of intermediate HC-28-3
8.7 g (30.2 mmol) of intermediate HC-28-2, 7.5 g (36.2 mmol) of intermediate C (2-bromonaphthalene), 4.3 g (45.3 mmol) of sodium tert-butoxide (NaOtBu), 1.0 g (1.8 mmol) of Pd (dba) were reacted with each other 2 And 2.2 g of tri-tert-butylphosphine (P (tBu) 3 ) (50% in toluene) was added to 150 ml of xylene in a 500 ml flask, and the mixture was heated under a nitrogen stream and refluxed for 12 hours. After removal of xylene, 200 ml of methanol was added to the mixture obtained therefrom to crystallize the solid, and the solid was filtered, dissolved in methylene chloride, filtered through silica gel/celite, and after an appropriate amount of organic solvent was removed therefrom, recrystallized with acetone to obtain intermediate HC-28-3 (9.83 g, yield 77%).
d) Synthesis of intermediate HC-28-4
Intermediate HC-28-3 (211.37 g, 0.51 mol) and triethyl phosphite (triethyl phosphite) (528 ml, 3.08 mol) were placed in a 1000 ml flask and after being replaced with nitrogen, the mixture was stirred at 160 ℃ for 12 hours. When the reaction was complete, 3 liters of MeOH was added thereto, and the obtained mixture was stirred and filtered, and the filtrate was volatilized. The residue was purified by column chromatography using hexane (hexane) to obtain intermediate HC-28-4 (152.14 g, yield 78%).
e) Synthesis of Compound HC-28
[ reaction scheme 7]
Compound HC-28 was synthesized according to the same method as in c) of synthesis example 6 using intermediate HC-28-4 and intermediate HC-28-B.
Synthesis example 7: synthesis of Compound HC-18
[ reaction scheme 8]
a) Synthesis of intermediate HC-18-1
According to the same manner as in c) of Synthesis example 9, 4-bromobiphenyl was used as an intermediate instead of 2-bromonaphthalene, and intermediate HC-18-1 was synthesized.
b) Synthesis of intermediate HC-18-2
Intermediate HC-18-2 was synthesized according to the same method as in d) of Synthesis example 9.
c) Synthesis of intermediate HC-18-3
[ reaction scheme 9]
Intermediate HC-18-3 was synthesized in the same manner as in B) of Synthesis example 1 using intermediate HC-18-A and intermediate HC-18-B.
d) Synthesis of Compound HC-18
[ reaction scheme 10]
Compound HC-18 was synthesized in the same manner as in e) of Synthesis example 9 using HC-18-2 as an intermediate and HC-18-3 as an intermediate.
Synthesis example 8: synthesis of Compound HC-20
a) Synthesis of intermediate HC-20-1
[ reaction scheme 11]
Intermediate HC-20-1 was synthesized using intermediate HC-20-A and intermediate HC-20-B in the same manner as in B) of Synthesis example 1.
b) Synthesis of Compound HC-20
[ reaction scheme 12]
Compound HC-20 was synthesized using intermediate HC-18-2 and intermediate HC-20-1 according to the same method as in e) of synthesis example 9.
Synthesis example 9: synthesis of Compound HC-37
[ reaction scheme 13]
Compound HC-37 was synthesized in the same manner as in e) of Synthesis example 9 using HC-28-4 as an intermediate and HC-18-3 as an intermediate.
Synthesis example 10: synthesis of Compound C-14
[ reaction scheme 14]
8 g (31.2 mmol) of intermediate I-1, 20.5 g (73.32 mmol) of 4-iodobiphenyl (4-iodobiphenyl), 1.19 g (6.24 mmol) of CuI, 1.12 g (6.24 mmol) of 1,10-phenanthroline (1, 10-phenanthrine) and 12.9 g (93.6 mmol) of K 2 CO 3 Put into a round bottom flask, 50 ml DMF was added thereto, and the mixture was refluxed under nitrogen atmosphere and stirred for 24 hours. When the reaction is completed, distilled water is added thereto toThe solid was precipitated and filtered. The solid was dissolved in 250 ml of xylene (xylene) and filtered through a silica gel to precipitate a white solid, thereby obtaining 16.2 g of compound C-14 (yield 93%).
Synthesis example 11: synthesis of Compound F-148
Reference is made to korean registered patent No. 10-1627746 for the synthesis of compound F-148.
Comparative Synthesis example 1 and comparative Synthesis example 2
Referring to Korean patent laid-open No. 10-2016-0149527, compound Ref.1 and compound Ref.2 were synthesized, respectively.
Manufacturing organic light emitting diode
Example 1
Coating with Indium Tin Oxide (ITO) with distilled water to 1500 angstromsThe thick film glass substrate was washed. After washing with distilled water, the glass substrate is ultrasonically washed (ultra sonic wave-washed) and dried with a solvent such as isopropyl alcohol, acetone, methanol, etc., and then moved to a plasma cleaner (plasma cleaner), cleaned with oxygen plasma for 10 minutes, and moved to a vacuum deposition device. Using such an ITO transparent electrode obtained as an anode, compound a was vacuum deposited on an ITO substrate to form a 700 a thick hole injection layer, compound B was deposited to a thickness of 50 a on the injection layer, and compound C was deposited to a thickness of 700 a to form a hole transport layer. Compound F-148 synthesized in synthesis example 11 was deposited on the hole transport layer to form a 400 angstrom thick hole transport auxiliary layer. Compound B-24 synthesized in Synthesis example 1 and Compound HC-28 synthesized in Synthesis example 6 were subjected to simultaneous vacuum deposition as a host and 2% by weight (wt.%) of [ Ir (piq) 2 acac]As a dopant, a 400 angstrom thick light emitting layer was formed on the hole transport auxiliary layer. Here, compound B-24 and compound HC-28 were used in a weight ratio of 3:7. Subsequently, the compound D and Liq were simultaneously vacuum deposited on the light emitting layer at a ratio of 1:1 to form a 300 angstrom thick electron transport layer, and a cathode was formed by sequentially vacuum depositing Liq to a thickness of 15 angstrom and Al to a thickness of 1200 angstrom on the electron transport layer, thereby manufacturing an organic light emitting diode.
The organic light emitting diode has a six-layered organic thin structure, and in particular, the following structure.
ITO/Compound A (700A)/Compound B (50A)/Compound C (700A)/Compound F-148 (400A)/EML [ Compound B-24:HC-28: [ Ir (piq) ] 2 acac](2 wt.%)](400 angstroms)/compound D Liq (300 angstroms)/Liq (15 angstroms)/Al (1200 angstroms).
Compound a: n4, N4'-diphenyl-N4, N4' -bis (9-phenyl-9H-carbazol-3-yl) biphenyl-4,4'-diamine (N4, N4' -diphenyl-N4, N4'-bis (9-phenyl-9H-carbazol-3-yl) biphenyl-4,4' -diamine)
Compound B:1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile (1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile, HAT-CN),
compound C: n- (biphenyl-4-yl) -9,9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluorene-2-amine (N- (biphen-4-yl) -9,9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluoren-2-amine)
Compound D:8- (4, 6-bis (naphthalen-2-yl) -1,3, 5-triazin-2-yl) phenyl) quinolone (8- (4, 6-di (naphthalen-2-yl) -1,3, 5-triazin-2-yl) phenyl) quinone)
Examples 2 to 9 and comparative examples 1 to 6
An organic light-emitting diode was fabricated in the same manner as in example 1, except that each of the compounds shown in table 1 was used instead of the compound B-24 and the compound HC-28 as the main bodies of the light-emitting layers, and each of the compounds shown in table 1 was used instead of the compound F-148 of the hole-transport auxiliary layer.
Evaluation
The driving voltages and power efficiencies of the organic light emitting diodes according to examples 1 to 9 and comparative examples 1 to 6 were measured.
The specific measurement method is as follows, and the results are shown in table 1.
(1) Measuring driving voltage
The driving voltage of each diode was measured using a current-voltage meter (Keithley) 2400 to obtain a result.
(2) Measuring current density variations dependent on voltage variations
Regarding the value of the current flowing in the unit device, the obtained organic light emitting diode was measured using a current-voltage meter (Keithley) 2400 when the voltage was increased from 0 volt to 10 volts, and the measured current value was divided by the area, thereby obtaining a result.
(3) Measuring brightness change dependent on voltage change
Brightness was measured using a brightness meter (Minolta) Cs-1000A as the voltage of the organic light emitting diode increased from 0 volts to 10 volts.
(4) Measuring power efficiency
The power efficiency (lm/w) is calculated using the brightness, current density and voltage measured in (2) and (3).
TABLE 1
Referring to table 1, the organic light emitting diodes according to examples 1 to 9 showed significantly low driving voltages and significantly improved power efficiency compared to the organic light emitting diodes according to comparative examples 1 to 6.
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.
Claims (15)
1. An organic optoelectronic device, comprising:
an anode and a cathode facing each other,
a light-emitting layer arranged between the anode and the cathode,
a hole transport layer disposed between the anode and the light emitting layer, and
a hole transport auxiliary layer disposed between the light emitting layer and the hole transport layer, wherein the light emitting layer comprises a first compound represented by chemical formula 1 and a second compound represented by a combination of chemical formula 2 and chemical formula 3, and
the hole transport auxiliary layer includes a third compound represented by chemical formula 4:
[ chemical formula 1]
Wherein, in the chemical formula 1,
X 1 is either O or S, and is preferably selected from the group consisting of,
Z 1 to Z 3 Independently N or CR a ，
Z 1 To Z 3 At least two of which are N,
Ar 1 ar and Ar 2 Independently hydrogen, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
L 1 to L 3 Independently a single bond, a substituted or unsubstituted C6 to C30 arylene, a divalent substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
R 1 To R 5 R is as follows a Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or a combination thereof,
R 1 to R 3 Independently present or R 1 To R 3 Two adjacent of them are combined to form a ring, and
R 4 r is R 5 Independently or fused to each other to form a ring,
wherein, in chemical formula 2 or chemical formula 3,
Y 1 y and Y 2 Independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,
A 1 a is a 2 Independently a substituted or unsubstituted C6 to C30 aryl,
two adjacent ones of chemical formula 2 are bonded to two of chemical formula 3, and the remaining two of chemical formula 2 are CR, respectively b CR (computed tomography) c ，
R 20 To R 23 、R b R is R c Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, or a combination thereof,
R 20 r is R 21 Independently present or condensed with each other to form a ring, and
R 22 r is R 23 Independently or fused to each other to form a ring,
[ chemical formula 4]
Wherein, in the chemical formula 4,
L 4 To L 9 Independently a single bond, a substituted or unsubstituted C6 to C30 arylene, a divalent substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
R 50 to R 55 Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or a combination thereof,
R 50 r is R 51 Independently or fused to each other to form a ring,
R 52 r is R 53 Independently present or condensed with each other to form a ring, and
R 54 r is R 55 Independently or fused to each other to form a ring.
2. The organic photoelectric device according to claim 1, wherein Ar of chemical formula 1 1 Ar and Ar 2 Independently is hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenylyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or a combination thereof.
3. The organic photoelectric device according to claim 1, wherein Ar of chemical formula 1 1 Ar and Ar 2 Independently one of the substituted or unsubstituted groups listed in group 1:
group 1
4. The organic optoelectronic device according to claim 1, wherein the first compound is represented by chemical formula 1A:
[ chemical formula 1A ]
Wherein, in the chemical formula 1A,
X 1 is either O or S, and is preferably selected from the group consisting of,
Z 1 to Z 3 Independently N or CR a ，
Z 1 To Z 3 At least two of which are N,
Ar 1 ar and Ar 2 Independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
L 2 l and L 3 Independently a single bond, a substituted or unsubstituted C6 to C30 arylene, a divalent substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
R 1 to R 5 、R a 、R p 、R q 、R r R is as follows s Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or a combination thereof,
R 1 to R 3 Independently present or R 1 To R 3 Which are combined to form a ring,
R 4 r is R 5 Independently or fused to each other to form a ring,
R p R is R q Independently or fused to each other to form a ring,
R r r is R s Independently present or condensed with each other to form a ring, and
n1 is an integer from 0 to 2.
5. The organic optoelectronic device according to claim 4, wherein the first compound is represented by one of chemical formulas 1A-1 to 1A-3:
[ chemical formulas 1A-3]
Wherein, in chemical formulas 1A-1 to 1A-3,
X 1 x is X 2 Independently of which is O or S,
Z 1 to Z 6 Independently N or CR a ，
Z 1 To Z 3 At least two of which are N,
Z 4 to Z 6 At least one of which is N,
Ar 1 ar and Ar 2 Independently hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
L 2 l and L 3 Independently a single bond, a substituted or unsubstituted C6 to C30 arylene, a divalent substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
R 1 to R 15 、R a 、R p 、R q 、R r R is as follows s Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or a combination thereof,
R 1 to R 3 Independently present or R 1 To R 3 Which are combined to form a ring,
R 4 R is R 5 Independently or fused to each other to form a ring,
R 6 r is R 7 Independently or fused to each other to form a ring,
R 9 to R 13 Independently present or R 9 To R 13 Which are combined to form a ring,
R p r is R q Independently or fused to each other to form a ring,
R r r is R s Independently present or condensed with each other to form a ring, and
n1 is an integer from 0 to 2.
6. The organic optoelectronic device according to claim 5, wherein
Ar 1 、Ar 2 、R 14 R is as follows 15 Independently is hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl or substituted or unsubstituted fluorenyl, and
R p 、R q 、R r r is as follows s Independently is hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, cyano, or a combination thereof.
7. The organic optoelectronic device according to claim 1, wherein the second compound is represented by one of chemical formula 2-a to chemical formula 2-E:
Wherein, in chemical formulas 2-A to 2-E,
Y 1 y and Y 2 Independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,
A 1 a is a 2 Independently a substituted or unsubstituted C6 to C30 aryl,
R 20 to R 23 、R b R is R c Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, or a combination thereof,
R 20 r is R 21 Independently present or condensed with each other to form a ring, and
R 22 r is R 23 Independently or fused to each other to form a ring.
8. The organic optoelectronic device according to claim 1, wherein Y 1 Y and Y 2 Independently is a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted naphthylene, and
A 1 a is a 2 Independently is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthryl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted polytrimethylphenyl, a substituted or unsubstituted fluorenyl, or a combination thereof.
9. The organic optoelectronic device according to claim 1, wherein R of chemical formula 4 50 To R 55 Independently is hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted polytrimethylenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, or a combination thereof.
10. The organic optoelectronic device according to claim 1, wherein R of chemical formula 4 50 To R 55 Independently is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthryl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted polytrimethylphenyl, or a combination thereof.
11. The organic optoelectronic device according to claim 1, wherein R of chemical formula 4 50 To R 55 At least one of which is a group represented by formula a:
[ chemical formula A ]
Wherein, in the chemical formula A,
X 3 is either O or S, and is preferably selected from the group consisting of,
R 60 to R 67 Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclyl, substituted or unsubstituted silyl, substituted or unsubstituted amino, halogen, cyano, or a combination thereof, or with L of formula 4 4 To L 9 A group attached to one of them, an
R 60 To R 67 Independently present or R 60 To R 67 Which combine to form a ring.
12. The organic optoelectronic device according to claim 1, wherein the hole transport auxiliary layer contacts the light emitting layer.
13. The organic optoelectronic device according to claim 1, wherein the hole transport layer comprises a compound represented by chemical formula 5:
[ chemical formula 5]
Wherein, in the chemical formula 5,
R 118 to R 121 Independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
R 118 r is R 119 Independently or fused to each other to form a ring,
R 120 r is R 121 Independently or fused to each other to form a ring,
Ar 10 to Ar 12 Independently is a substituted or unsubstituted C6 to C30 aryl or a substituted or unsubstituted C2 to C30 heterocyclyl, and
L 10 to L 13 Independently a single bond, a substituted or unsubstituted C6 to C30 arylene, a divalent substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof.
14. The organic optoelectronic device according to claim 13, wherein Ar of chemical formula 5 10 Is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, and
Ar of chemical formula 5 11 Ar and Ar 12 Independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted bifluorenyl group, a substituted or unsubstituted bistriphenyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a combination thereof.
15. A display device comprising the organic optoelectronic device according to any one of claims 1 to 14.
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| KR102368409B1 (en) | 2019-05-30 | 2022-02-25 | 삼성에스디아이 주식회사 | Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device |
| CN117343078A (en) | 2021-11-25 | 2024-01-05 | 北京夏禾科技有限公司 | Organic electroluminescent material and device |
| KR20240031014A (en) | 2022-08-30 | 2024-03-07 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same |
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20190038108A (en) | 2019-04-08 |
| WO2019066315A3 (en) | 2019-05-23 |
| WO2019066315A2 (en) | 2019-04-04 |
| TWI703203B (en) | 2020-09-01 |
| KR102199075B1 (en) | 2021-01-07 |
| CN111095586A (en) | 2020-05-01 |
| TW201920603A (en) | 2019-06-01 |
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