CN111095586A - Organic photoelectric device and display device - Google Patents
Organic photoelectric device and display device Download PDFInfo
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- CN111095586A CN111095586A CN201880060459.7A CN201880060459A CN111095586A CN 111095586 A CN111095586 A CN 111095586A CN 201880060459 A CN201880060459 A CN 201880060459A CN 111095586 A CN111095586 A CN 111095586A
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- YLDRZUXMDFTACH-UHFFFAOYSA-N CC1(OB(OC1(C)C)B1OC(C(O1)(C)C)(C)C)C.O1BOCC1 Chemical compound CC1(OB(OC1(C)C)B1OC(C(O1)(C)C)(C)C)C.O1BOCC1 YLDRZUXMDFTACH-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- VETCVOIBHHLDAG-UHFFFAOYSA-N ClC1=C([C-](C=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)Cl.[CH-]1C=CC=C1.[Fe+2] Chemical compound ClC1=C([C-](C=C1)P(C1=CC=CC=C1)C1=CC=CC=C1)Cl.[CH-]1C=CC=C1.[Fe+2] VETCVOIBHHLDAG-UHFFFAOYSA-N 0.000 description 1
- BQHRJUASXACWDG-UHFFFAOYSA-N ClN1NC(=CC(=N1)Cl)C1=CC=CC=C1 Chemical compound ClN1NC(=CC(=N1)Cl)C1=CC=CC=C1 BQHRJUASXACWDG-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- GZEYAHWZGYWNDL-UHFFFAOYSA-N IC=1C=C(C(=CC1)O)C=1C(=CC=CC1)O.IC1=CC=C(C=C1)C1=CC=CC=C1 Chemical compound IC=1C=C(C(=CC1)O)C=1C(=CC=CC1)O.IC1=CC=C(C=C1)C1=CC=CC=C1 GZEYAHWZGYWNDL-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N SnO2 Inorganic materials O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- NACCJOIEZISYCU-UHFFFAOYSA-M [Br-].C1=CC([Mg+])=CC=C1C1=CC=CC=C1 Chemical compound [Br-].C1=CC([Mg+])=CC=C1C1=CC=CC=C1 NACCJOIEZISYCU-UHFFFAOYSA-M 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 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
- 230000009286 beneficial effect Effects 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
- 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
- 238000004364 calculation method Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 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
- 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
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 230000001419 dependent effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-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
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000000694 effects Effects 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
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 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
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 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
- HZZOEADXZLYIHG-UHFFFAOYSA-N magnesiomagnesium Chemical compound [Mg][Mg] HZZOEADXZLYIHG-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 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
- 108091008695 photoreceptors Proteins 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
- 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004576 sand Substances 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
- 238000004544 sputter deposition Methods 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
- 229930192474 thiophene Natural products 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 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
- 229910052727 yttrium Inorganic materials 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention discloses an organic photoelectric device and a display device including the same, the organic photoelectric 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 assist 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 assist layer includes a third compound represented by chemical formula 4. Chemical formulas 1 to 4 are the same as those provided in the specification.
Description
Technical Field
The invention discloses an organic photoelectric device and a display device.
Background
An organic photoelectric device (organic photodiode) is a device that converts electrical energy into optical energy and vice versa.
Organic photoelectric devices may be classified according to their driving principle as follows. One is an optoelectronic device in which excitons (exitons) 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 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 (oled), an organic solar cell, and an organic photoreceptor drum.
Among them, Organic Light Emitting Diodes (OLEDs) have recently attracted attention due to an increase in demand for flat panel display devices (flat panel displays). The organic light emitting diode converts electric energy into light by applying current to the organic light emitting material, and the performance 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 scheme
According to an embodiment, an organic photoelectric 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 assist 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 assist layer includes a third compound represented by chemical formula 4.
[ chemical formula 1]
In the chemical formula 1, the first and second,
X1is O or S, and is a compound of,
Z1to Z3Independently is N or CRa，
Z1To Z3At least two of which are N,
Ar1and Ar2Independently hydrogen, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
L1to L3Independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclyl group, or a combination thereof,
R1to R5And RaIndependently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocycleA group, a substituted or unsubstituted silane group, a substituted or unsubstituted amino group, a halogen, a cyano group, or a combination thereof,
R1to R3Independently exist or R1To R3Are combined to form a ring, and
R4and R5Independently present or fused to each other to form a ring,
wherein, in chemical formula 2 or chemical formula 3,
Y1and Y2Independently a single bond or a substituted or unsubstituted C6 to C30 arylene,
A1and A2Independently a substituted or unsubstituted C6 to C30 aryl group,
two adjacent ones of formula 2 are bonded to two of formula 3, and the remaining two of formula 2 are CRbAnd CRc，
R20To R23、RbAnd RcIndependently 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,
R20and R21Independently exist or are fused to each other to form a ring, an
R22And R23Independently present or fused to each other to form a ring,
[ chemical formula 4]
Wherein, in chemical formula 4,
L4to L9Independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclyl group, or a combination thereof,
R50to R55Independently 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,
R50and R51Independently present or fused to each other to form a ring,
R52and R53Independently exist or are fused to each other to form a ring, an
R54And R55Independently present or fused to each other to form a ring.
According to another embodiment, there is provided a display device including the organic photoelectric device.
Beneficial effect
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.
Detailed Description
Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, the invention is not limited thereto, and the invention is defined by the scope of the claims.
In the present specification, when a definition is not otherwise provided, "substituted" means that at least one hydrogen of a substituent or a compound is replaced 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 one embodiment of the invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced with deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, or C2 to C30 heteroaryl. Additionally, in embodiments of the invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced with deuterium, C1 to C20 alkyl, C6 to C30 aryl, or C2 to C30 heteroaryl. In addition, in embodiments 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, dibenzothiophenyl, or carbazolyl. Additionally, in particular examples of the present invention, "substituted" refers to replacement of at least one hydrogen of a substituent or compound with deuterium, C1 to C5 alkyl, C6 to C18 aryl, dibenzofuranyl, or dibenzothiophenyl. In addition, in particular embodiments of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced with deuterium, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, naphthyl, triphenyl, dibenzofuranyl, or dibenzothiophenyl.
In the present specification, when a 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 are carbon.
In the present specification, "aryl group" means a group comprising at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p orbitals forming conjugation, such as phenyl, naphthyl, and the like, two or more hydrocarbon aromatic moieties may be connected by sigma bonds, and may be, for example, biphenyl, terphenyl, tetraphenyl, and the like, and two or more hydrocarbon aromatic moieties are directly or indirectly fused (fuse) to provide a non-aromatic fused ring (e.g., fluorene group).
Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.
In the present specification, "heterocyclic group" is a general concept of heteroaryl group, and may include at least one heteroatom selected from N, O, S, P and Si instead of carbon (C) in a cyclic compound such as aryl group, cycloalkyl group, fused ring 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, a "heteroaryl (heteroaryl) group" 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 bond, or when the C2 to C60 heteroaryl groups contain 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.
Specific examples of the heterocyclic group may be pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl and the like.
More specifically, the substituted or unsubstituted C6-C30 aryl group and/or the substituted or unsubstituted C2-C30 heterocyclic 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 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 group (chrysenyl group), a substituted or unsubstituted biphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl groupA substituted 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 isoquinolyl 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 benzothiophenyl group, a substituted or unsubstituted acridinyl group (acridinyl group), a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group or combinations thereof, but is not limited thereto.
In this specification, the hole characteristics refer to an ability to donate (donate) electrons to form holes when an electric field (electric field) is applied, and due to a conduction characteristic according to a Highest Occupied Molecular Orbital (HOMO) energy level, holes formed in an anode may be easily injected into a light emitting layer and holes formed in the light emitting layer may be easily transported into and in the anode.
In addition, the electron characteristics refer to an ability to accept electrons when an electric field is applied, and due to a conduction characteristic according to a Lowest Unoccupied Molecular Orbital (LUMO) level, 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 transported into the cathode and in the light emitting layer.
Hereinafter, an organic photoelectric 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.
Herein, an organic light emitting diode is described as an example of an organic photoelectric device, but the present invention is not limited thereto, and may be applied to other organic photoelectric 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).
The anode (110) 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 (110) may be, for example, metallic nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and the like; combinations of metals with oxides, e.g. ZnO with Al or SnO2And Sb; conductive polymers, such as poly (3-methylthiophene), poly (3,4- (ethylene-1, 2-dioxy) thiophene) (polyethylenedioxythiophene): PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
The cathode (120) 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 (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 (multi-layer) structural materials, e.g. LiF/Al, LiO2Al, LiF/Ca, LiF/Al andBaF2but 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 a relatively strong electronic characteristic may be represented by chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, the first and second,
X1is O or S, and is a compound of,
Z1to Z3Independently is N or CRa，
Z1To Z3At least two of which are N,
Ar1and Ar2Independently hydrogen, deuterium, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
L1to L3Independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclyl group, or a combination thereof,
R1to R5And RaIndependently 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,
R1to R3Independently exist or R1To R3Are combined to form a ring, and
R4and R5Independently present 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 may increase the planarity of the molecular structure while effectively expanding the LUMO band (energy 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 energy band is enlarged, the electron stability is also increased, and thus the lifetime of the organic photoelectric device may be improved.
For example, Z1To Z3Two of which may be nitrogen.
For example, Z1And Z2Can be nitrogen, and Z3May be CRa。
For example, Z2And Z3Can be nitrogen, and Z1May be CRa。
For example, Z1And Z3Can be nitrogen, and Z2May be CRa。
For example, Z1To Z3Each of which may be nitrogen.
For example, Ar1And Ar2May independently be hydrogen, deuterium, 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 anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, or a combination thereof.
For example, Ar1And Ar2Can independently be hydrogenDeuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group or a substituted or unsubstituted fluorene group.
For example, Ar1And Ar2Can independently be one of the substituted or unsubstituted groups of group 1.
[ group 1]
For example, L1To L3May 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 dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted carbazolyl group or a substituted or unsubstituted fluorene group. For example, L1May 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. Here, "substituted" means that at least one hydrogen is replaced with deuterium, C1 to C20 alkyl, C6 to C12 aryl, or cyano.
For example, L3May be a single bond.
In one embodiment of the present invention, when L is1When it is a single bond, Ar1Is other than hydrogen and deuterium, and when L2When it is a single bond, Ar2Other than hydrogen and deuterium.
For example, the first compound may be represented by chemical formula 1A.
[ chemical formula 1A ]
In chemical formula 1A, X1、Z1To Z3、Ar1、Ar2、L2、L3And R1To R5As described above.
In the chemical formula 1A, the metal oxide,
Rp、Rq、Rrand RsIndependently 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,
Rpand RqIndependently present or fused to each other to form a ring,
Rrand RsIndependently exist or are fused to each other to form a ring, an
n1 is an integer from 0 to 2.
For example, Rp、Rq、RrAnd RsMay 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 fluorene, cyano or combinations thereof.
The first compound represented by chemical formula 1A includes at least one meta (meta) bonded arylene group, which may inhibit interaction with adjacent molecules and reduce crystallization due to steric hindrance (steric hindrance) 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 (Tg), and may inhibit degradation of the first compound during the manufacturing process and/or operation of the organic photoelectric device, and thus may increase the thermal stability of the first compound.
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 formulae 1A-1 to 1A-3, X1、Z1To Z3、Ar1、Ar2、L2、L3、R1To R5、Rp、Rq、Rr、RsAnd n1 is the same as described above.
In chemical formulas 1A-1 to 1A-3,
X2is O or S, and is a compound of,
Z4to Z6Independently is N or CRa，
Z4To Z6At least one of which is N, is,
R6to R15Independently 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,
R6and R7Independently exist or are fused to each other to form a ring, an
R9To R13Independently exist or R9To R13Are combined to form a ring.
For example, Z4To Z6At least one of which may be nitrogen.
For example, Z4To Z6Two of which may be nitrogen.
For example, Z4And Z5Can be nitrogen, and Z6May be CRa。
For example, Z4And Z6Can be nitrogen, and Z5May be CRa。
For example, Z5And Z6Can be nitrogen, and Z4May be CRa。
For example, Z4To Z6Each of which may be nitrogen.
For example, Ar1、Ar2、R14And R15May independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl or substituted or unsubstituted fluorene.
For example, Rp、Rq、RrAnd RsMay 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 fluorene, cyano or combinations 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 chemical formula 2 or chemical formula 3,
Y1and Y2Independently a single bond or a substituted or unsubstituted C6 to C30 arylene,
A1and A2Independently a substituted or unsubstituted C6 to C30 aryl group,
two adjacent ones of formula 2 are bonded to two of formula 3, and the remaining two of formula 2 are CRbAnd CRc，
R20To R23、RbAnd RcIndependently 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,
R20and R21Independently exist or are fused to each other to form a ring, an
R22And R23Independently present or fused to each other 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 is achieved.
For example, Y1And Y2May 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 fluorene group.
For example, Y1And Y2May 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, Y1And Y2May independently be a single bond, a substituted or unsubstituted meta phenylene group, a substituted or unsubstituted para phenylene group, a substituted or unsubstituted meta biphenylene group, a substituted or unsubstituted para biphenylene group, or a substituted or unsubstituted naphthylene group. Wherein "substituted" means that at least one hydrogen is replaced with deuterium, C1 to C20 alkyl, C6 to C12 aryl, or cyano.
For example, A1And A2May independently be a 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 bistriphenylene, substituted or unsubstituted fluorene, or combinations thereof.
For example, A1And A2And may independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl.
The second compound may be represented by one of chemical formulas 2-a to 2-E depending on a bonding position between chemical formulas 2 and 3.
In chemical formulae 2-A to 2-E, Y1、Y2、A1、A2、R20To R23、RbAnd RcAs described above.
In an embodiment of the 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 be specifically 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 an 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 present invention, the first compound and the second compound 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 include at least one compound other than the first compound and the second compound.
The light-emitting layer (130) may further comprise 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 light emission, and may be generally an organic compound or metal complex (e.g., Al) that emits fluorescence by singlet excitation or a material that emits light by multiple excitation from a ground state (multiple excitation) to a triplet state or more than a triplet state (e.g., metal complex). The dopant may be, for example, an inorganic compound, an organic compound, or an organic/inorganic compound, and one or more species 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 formula Z, but is not limited thereto.
[ chemical formula Z ]
L2MX
In formula Z, M is a metal, and L and X are the same or different and are ligands (ligands) that form a complexed compound 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 and X can be, for example, bidentate ligands (bidendate ligands).
The hole transport assisting 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 assist layer (142) can precisely control hole mobility at the interface between the light emitting layer (130) and the hole transport layer (141) by contacting the light emitting layer (130). The hole transport assist layer (142) may include multiple layers.
The hole transport assisting layer (142) may include, for example, a third compound represented by chemical formula 4.
[ chemical formula 4]
In the chemical formula 4, the first and second organic solvents,
L4to L9Independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclyl group, or a combination thereof,
R50to R55Independently 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,
R50and R51Independently present or fused to each other to form a ring,
R52and R53Independently exist or are fused to each other to form a ring, an
R54And R55Independently present 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. Therefore, the third compound is applied to the hole transport auxiliary layer (142), and thus, the hole mobility at the interface between the light emitting layer (130) and the hole transport layer (141) can be effectively improved, and the driving voltage of the organic photoelectric device can be effectively reduced.
For example, L4To L9May 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 dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted carbazolyl group or a substituted or unsubstituted fluorene group. For example, L4To L9Can be independently a single bond, a warpSubstituted or unsubstituted m-phenylene, substituted or unsubstituted p-phenylene, substituted or unsubstituted m-biphenylene, substituted or unsubstituted p-biphenylene or substituted or unsubstituted naphthylene. Here, "substituted" means that at least one hydrogen is replaced with deuterium, C1 to C20 alkyl, C6 to C12 aryl, or cyano.
For example, R50To R55May independently be hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C3 to C30 heterocyclyl.
For example, R50To R55May independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl or substituted or unsubstituted fluorene.
For example, R50To R55May independently be a substituted or unsubstituted C6 to C30 aryl group, or may independently be, for example, 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 bitriphenylene group, or a combination thereof.
For example, R50To R55At least one of which may be a substituted or unsubstituted C3 to C30 heterocyclyl.
For example, R50To R55At least one of the groups may be a group represented by formula a.
[ chemical formula A ]
In the chemical formula A, the compound represented by the formula A,
X3is O or S, and is a compound of,
R60to R67Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclic, substituted or unsubstituted silane, substituted or unsubstituted amino, halogen, cyano, or a combination thereof, or with L of formula 44To L9Is a group to which one of them is attached, and
R60to R67Independently exist or R60To R67Are combined to form a ring.
For example, R50To R55One of the groups may be a group represented by formula A, and R50To R55The others of (a) may independently be substituted or unsubstituted C6 to C30 aryl.
For example, R50To R55May be a group represented by formula A, and R50To R55The others of (a) may independently be substituted or unsubstituted C6 to C30 aryl.
For example, R50To R55May be a group represented by formula A, and R50To R55The others of (a) may independently be substituted or unsubstituted C6 to C30 aryl.
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 can facilitate easy transport of holes from the anode (110) into the light emitting layer (130). For example, the hole transport layer (141) may comprise a material having a HOMO level between the work function of the conductor forming the anode (110) and the HOMO level of the material forming the light emitting layer (130).
The hole transport layer (141) may comprise, 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 first and second organic solvents,
R118to R121Independently 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,
R118and R119Independently present or fused to each other to form a ring,
R120and R121Independently present or fused to each other to form a ring,
Ar10to Ar12Independently is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclyl group, and
L10to L13Independently 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, Ar10May be a substituted or unsubstituted C6 to C30 aryl group, and for example Ar10May be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.
For example, Ar11And Ar12May independently be a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted bisfluorene, substituted or unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted terphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or combinations 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]
In addition to the light-emitting layer 130, the hole transport auxiliary layer 142, and the hole transport layer 141, 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).
The organic light emitting diode (300) may be manufactured by: forming an anode or a cathode on a substrate, forming an organic layer using a dry film forming method or a solution process such as evaporation (sputtering), plasma plating (plasma plating), and ion plating (ion plating), and forming a cathode or an anode 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 present 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 (g) (81.34 mmol) of cyanuric chloride (cyanuric chloride) were dissolved in 200 mL of anhydrous tetrahydrofuran in a 500 mL (mL) round bottom flask, 1 equivalent of 4-biphenylylmagnesium bromide solution (0.5M tetrahydrofuran) was added dropwise thereto at 0 ℃ under a nitrogen atmosphere, and the mixture was slowly heated 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. From this, an organic layer was separated, 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-bottomed flask, 2 equivalents of dibenzofuran-3-boronic acid (Chemical Abstracts Service, cas): 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 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 (monochlororobenzene) to obtain 13.05 g of compound B-24-2.
c) Synthesis of Compound B-24
Compound B-24 was synthesized in the same manner as B) using intermediate B-24-2 and 1.1 equivalents of B- [1,1':4',1 "-Terphenyl ] -3-ylboronic acid (B- [1,1':4', 1" -Terphenyl ] -3-yl boronic acid).
Liquid Chromatography (LC)/Mass Spectrometry (MS) calculation yields (calculated for): C45H29N3O Exact Mass (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 a 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, 0.05 equivalent of dichlorodiphenylphosphinoylferrocene palladium (dichlorodiphenylphosphinoferrocene palladium), 1.2 equivalents of bis (pinacolato) diboron and 2 equivalents of potassium acetate were added thereto, and the mixture was heated and refluxed for 18 hours under a nitrogen atmosphere. 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 together 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 according to the same method as in Synthesis example a) 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' -biphenyl ] -4-yl) -6-chloro-1,3,5-triazine) in amounts of 1.0 equivalent, respectively.
Calculated by LC/MS (calculated for): C45H29N3O Exact Mass (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 is placed in a 500 ml round-bottomed flask together with 100 ml of tetrahydrofuran, 100 ml of toluene and 100 ml of distilled water, 0.9 equivalent of dibenzofuran-3-boronic acid (CAS number: 395087-89-5), 0.03 equivalent of tetrakis-triphenylphosphine palladium and 2 equivalents of potassium carbonate are added thereto, and the mixture is 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 with 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 method as B) of Synthesis example 3, using intermediate B-20-1 and 1.1 equivalents of (5' -phenyl [1,1':3',1 "-terphenyl ] -4-yl) -boronic acid) (CAS No.: 491612-72-7) to synthesize Compound B-20.
Calculated by LC/MS (calculated for): C45H29N3O Exact Mass (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
Intermediate B-124-1 was synthesized according to B) of Synthesis example 1 using 1-bromo-3-chloro-5-phenylbenzene and 1.1 equivalents of biphenyl-4-boronic acid. Here, the resultant obtained therefrom was purified with hexane via flash column (flash column) without 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-bottomed flask, 0.05 equivalent of dichlorodiphenylphosphinoylferrocene palladium), 1.2 equivalents of bis (pinacolato) diboron and 2 equivalents of potassium acetate were added thereto, and the mixture was heated and refluxed for 18 hours under a nitrogen atmosphere. 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 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 in the same manner as in B) of Synthesis example 3, using intermediates B-124-2 and B-17-1 in amounts of 1.0 equivalent, respectively.
Calculated by LC/MS (calculated for): C45H29N3O Exact Mass (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 (magnesium) (7.86 g, 323 mmol) and iodine (iododine) (1.64 g, 6.46 mmol) were stirred with 0.1 l Tetrahydrofuran (THF) under nitrogen for 30 minutes and 1-bromo-3,5-diphenylbenzene (1-bromo-3, 5-diphenylbezene) (100 g, 323 mmol) dissolved in 0.3 l tetrahydrofuran was slowly added dropwise thereto over 30 minutes at 0 ℃. The resulting mixed solution was slowly added dropwise over 30 minutes at 0 ℃ to 64.5 g (350 mmol) of a solution of cyanuric chloride dissolved in 0.5 l of Tetrahydrofuran (THF). When the reaction was completed, water was added to the reaction solution, and an extract was obtained with dichloromethane (dichromethane, DCM) over anhydrous MgSO4After removing water 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.
Calculated by LC/MS (calculated for): C45H27N3O2 Exact Mass (Exact Mass): 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 4,4,4',4',5,5,5',5' -octamethyl-2,2' -bis (1,3, 2-dioxaborolan) (4,4,4',4',5,5,5',5' -octamethyl-2,2' -bi (1,3,2-dioxaborolane)), 2 equivalents of potassium acetate, 0.03 equivalents of 1,1' -bis (diphenylphosphino) ferrocene-palladium (ii) dichloride, and 0.2 equivalents 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 white solid 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 at 90 ℃ under a nitrogen stream for 16 hours. After the reaction solvent was removed therefrom, the resultant obtained therefrom was dissolved in dichloromethane, filtered through silica gel/celite, and recrystallized with methanol after an appropriate amount of organic solvent was removed therefrom, to obtain a 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)2And 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 and refluxed under a stream of nitrogen for 12 hours. After removing xylene, 200 ml of methanol was added to the mixture obtained therefrom to crystallize the solid, and the solid was filtered, dissolved in dichloromethane, filtered through silica gel/celite, and recrystallized with acetone after removing an appropriate amount of organic solvent therefrom, 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 (528 ml, 3.08 mol) were placed in a 1000 ml flask, and after displacement 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 evaporated. 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 in the same manner as in Synthesis example c) 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 method as that of c) of Synthesis example 9, using 4-bromobiphenyl as an intermediate in place of 2-bromonaphthalene, an intermediate HC-18-1 was synthesized.
b) Synthesis of intermediate HC-18-2
According to the same method as d) of Synthesis example 9, intermediate HC-18-2 was synthesized.
c) Synthesis of intermediate HC-18-3
[ reaction scheme 9]
The intermediate HC-18-3 was synthesized in the same manner as in B) in Synthesis example 1, using the intermediate HC-18-A and the 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 intermediate HC-18-2 and intermediate HC-18-3.
Synthesis example 8: synthesis of Compound HC-20
a) Synthesis of intermediate HC-20-1
[ reaction scheme 11]
The intermediate HC-20-1 was synthesized according to the same method as that of B) of Synthesis example 1, using the intermediate HC-20-A and the intermediate HC-20-B.
b) Synthesis of Compound HC-20
[ reaction scheme 12]
Compound HC-20 was synthesized in the same manner as in e) of Synthesis example 9, using intermediate HC-18-2 and intermediate HC-20-1.
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 intermediate HC-28-4 and intermediate HC-18-3.
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-iodobiphenol), 1.19 g (6.24 mmol) of CuI, 1.12 g (6.24 mmol) of 1,10-phenanthroline (1,10-phenanthroline) and 12.9 g (93.6 mmol) of K2CO3Put into a round bottom flask, 50 ml of DMF was added thereto, and the mixture was refluxed and stirred under a nitrogen atmosphere for 24 hours. When the reaction was completed, distilled water was added thereto to precipitate a solid, and the solid was filtered. The solid was dissolved in 250 ml of xylene (xylene) and filtered through 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
Refer to korean registered patent No. 10-1627746 for the synthesis of compound F-148.
Comparative synthesis examples 1 and 2
With reference to Korean patent laid-open publication No. 10-2016-0149527, compound Ref.1 and compound Ref.2 were synthesized, respectively.
Manufacture of organic light-emitting diode
Example 1
Coating with Indium Tin Oxide (ITO) to 1500 angstroms by distilled water
The thick thin film glass substrate is washed. After washing with distilled water, the glass substrate is ultrasonically washed (ultrasonically-washed) with a solvent such as isopropyl alcohol, acetone, methanol, etc., and dried, and then moved to a plasma cleaner (plasma cleaner), cleaned with oxygen plasma for 10 minutes, and moved to a vacuum depositor. Using this obtained ITO transparent electrode as an anode, compound a was vacuum-deposited on an ITO substrate to form a hole injection layer 700 a thick, compound B was deposited on the injection layer to 50 a thick, and compound C was deposited to 700 a thick 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. By simultaneous vacuum deposition of the compound B-24 synthesized in Synthesis example 1 and the compound HC-28 synthesized in Synthesis example 6 as hosts and vacuum deposition of 2 weight% (wt%) [ Ir (piq)2acac]As a dopant, a light-emitting layer of 400 angstroms in thickness 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, compounds D and Liq were simultaneously vacuum-deposited on the light emitting layer at a ratio of 1:1 to form an electron transport layer 300 angstroms thick, and a cathode was formed by sequentially vacuum-depositing Liq to 15 angstroms thick and Al to 1200 angstroms thick on the electron transport layer, thereby manufacturing an organic light emitting diode.
The organic light emitting diode has a six-layer organic thin structure, and specifically, the following structure.
ITO/Compound A (700. ANG.)/Compound B (50. ANG.)/Compound C (700. ANG.)/Compound F-148 (400. ANG.)/EML [ Compound B-24: HC-28: [ Ir (piq) ]2acac](2% by weight)](400. ANG)/Compound D Liq (300. ANG)/Liq (15. ANG)/Al (1200. ANG).
A 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-fluoren-2-amine (N- (biphenyl-4-yl) -9,9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluoren-2-amine)
Compound D: 8- (4- (4, 6-bis (naphthalen-2-yl) -1,3,5-triazin-2-yl) phenyl) quinolone (8- (4- (4,6-di (naphthalen-2-yl) -1,3,5-triazin-2-yl) phenyl) quinonone)
Examples 2 to 9 and comparative examples 1 to 6
An organic light-emitting diode was manufactured in the same manner as in example 1, except that each compound shown in table 1 was used instead of the compound B-24 and the compound HC-28 as a host of the light-emitting layer and each compound shown in table 1 was used instead of the compound F-148 of the hole transport auxiliary layer.
Evaluation of
The driving voltage and power efficiency of the organic light emitting diodes according to examples 1 to 9 and comparative examples 1 to 6 were measured.
Specific measurement methods are as follows, and the results are shown in table 1.
(1) Measuring drive 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
As for the value of the current flowing in the unit device, the obtained organic light emitting diode was measured while the voltage was increased from 0 volt to 10 volts using a current-voltmeter (Keithley)2400, and the measured current value was divided by the area, thereby obtaining the result.
(3) Measuring a change in brightness as a function of a change in voltage
The luminance was measured using a luminance meter (Minolta) Cs-1000A) while the voltage of the organic light emitting diode was increased from 0 volt to 10 volts.
(4) Measuring power efficiency
The power efficiency (lm/w) is calculated using the luminance, 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 show significantly lower driving voltage 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.
Description of the symbols
300: organic light emitting diode
110: anode
120: cathode electrode
130: luminescent layer
141: hole transport layer
142: hole transport auxiliary layer
Claims (15)
1. An organic optoelectronic device comprising:
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, an
And the hole transmission auxiliary layer is arranged between the light-emitting layer and the hole transmission 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]
Wherein, in chemical formula 1,
X1is O or S, and is a compound of,
Z1to Z3Independently is N or CRa，
Z1To Z3At least two of which are N,
Ar1and Ar2Independently hydrogen, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
L1to L3Independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclyl group, or a combination thereof,
R1to R5And RaIndependently 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,
R1to R3Independently exist or R1To R3Are combined to form a ring, and
R4and R5Independently present or fused to each other to form a ring,
wherein, in chemical formula 2 or chemical formula 3,
Y1and Y2Independently a single bond or a substituted or unsubstituted C6 to C30 arylene,
A1and A2Independently a substituted or unsubstituted C6 to C30 aryl group,
two adjacent ones of formula 2 are bonded to two of formula 3, and the remaining two of formula 2 are CRbAnd CRc，
R20To R23、RbAnd RcIndependently 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,
R20and R21Independently exist or are fused to each other to form a ring, an
R22And R23Independently present or fused to each other to form a ring,
[ chemical formula 4]
Wherein, in chemical formula 4,
L4to L9Independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclyl group, or a combination thereof,
R50to R55Independently 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,
R50and R51Independently present or fused to each other to form a ring,
R52and R53Independently exist or are fused to each other to form a ring, an
R54And R55Independently present or fused to each other to form a ring.
2. The organic photoelectric device according to claim 1, wherein Ar of chemical formula 11And Ar2Independently 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 anthrylSubstituted ditriphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or combinations thereof.
3. The organic photoelectric device according to claim 1, wherein Ar of chemical formula 11And Ar2Independently one of the substituted or unsubstituted groups listed in group 1:
[ group 1]
4. The organic photoelectric device according to claim 1, wherein the first compound is represented by chemical formula 1A:
[ chemical formula 1A ]
Wherein, in chemical formula 1A,
X1is O or S, and is a compound of,
Z1to Z3Independently is N or CRa，
Z1To Z3At least two of which are N,
Ar1and Ar2Independently hydrogen, deuterium, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
L2and L3Independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstitutedSubstituted C2 to C30 heterocyclyl or combinations thereof,
R1to R5、Ra、Rp、Rq、RrAnd RsIndependently 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,
R1to R3Independently exist or R1To R3Are combined to form a ring,
R4and R5Independently present or fused to each other to form a ring,
Rpand RqIndependently present or fused to each other to form a ring,
Rrand RsIndependently exist or are fused to each other to form a ring, an
n1 is an integer from 0 to 2.
5. The organic photoelectric device according to claim 4, wherein the first compound is represented by one of chemical formulae 1A-1 to 1A-3:
[ chemical formulas 1A-3]
Wherein, in chemical formulas 1A-1 to 1A-3,
X1and X2Independently of each other is O or S,
Z1to Z6Independently is N or CRa，
Z1To Z3At least two of which are N,
Z4to Z6At least one of which is N, is,
Ar1and Ar2Independently hydrogen, deuterium, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclyl, or a combination thereof,
L2and L3Independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclyl group, or a combination thereof,
R1to R15、Ra、Rp、Rq、RrAnd RsIndependently 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,
R1to R3Independently exist or R1To R3Are combined to form a ring,
R4and R5Independently present or fused to each other to form a ring,
R6and R7Independently present or fused to each other to form a ring,
R9to R13Independently exist or R9To R13Are combined to form a ring,
Rpand RqIndependently present or fused to each other to form a ring,
Rrand RsIndependently exist or are fused to each other to form a ring, an
n1 is an integer from 0 to 2.
6. The organic optoelectronic device according to claim 5, wherein
Ar1、Ar2、R14And R15Independently of each otherIs hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group or a substituted or unsubstituted fluorene group, and
Rp、Rq、Rrand RsIndependently 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 fluorene, cyano or combinations thereof.
7. The organic photoelectric device according to claim 1, wherein the second compound is represented by one of chemical formulae 2-a to 2-E:
wherein, in chemical formulas 2-A to 2-E,
Y1and Y2Independently a single bond or a substituted or unsubstituted C6 to C30 arylene,
A1and A2Independently a substituted or unsubstituted C6 to C30 aryl group,
R20to R23、RbAnd RcIndependently 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,
R20and R21Independently exist or are fused to each other to form a ring, an
R22And R23Independently present or fused to each other to form a ring.
8. The organic optoelectronic device according to claim 1, wherein Y is1And Y2Independently a single bondA substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene or a substituted or unsubstituted naphthylene group, and
A1and A2Independently a 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 bistriphenylene, substituted or unsubstituted fluorene group or combinations thereof.
9. The organic photoelectric device according to claim 1, wherein R of chemical formula 450To R55Independently 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 bitriphenylene, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorene, or combinations thereof.
10. The organic photoelectric device as claimed in claim 1, wherein R of chemical formula 450To R55Independently a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted biphenylenyl, or combinations thereof.
11. The organic photoelectric device according to claim 1, wherein R of chemical formula 450To R55At least one of which is a group represented by formula a:
[ chemical formula A ]
Wherein, in the chemical formula A,
X3is O or S, and is a compound of,
R60to R67Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heterocyclic, substituted or unsubstituted silane, substituted or unsubstituted amino, halogen, cyano, or a combination thereof, or with L of formula 44To L9Is a group to which one of them is attached, and
R60to R67Independently exist or R60To R67Are combined 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 photoelectric device according to claim 1, wherein the hole transport layer comprises a compound represented by chemical formula 5:
[ chemical formula 5]
Wherein, in chemical formula 5,
R118to R121Independently 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,
R118and R119Independently present or fused to each other to form a ring,
R120and R121Independently present or fused to each other to form a ring,
Ar10to Ar12Independently is a substituted or unsubstituted C6 to C30 aryl groupOr a substituted or unsubstituted C2 to C30 heterocyclic group, and
L10to L13Independently 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 photoelectric device according to claim 13, wherein Ar of chemical formula 510Is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, and
ar of chemical formula 511And Ar12Independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted pretilachlor, a substituted or unsubstituted bisfluorene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted anthryl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl or combinations thereof.
15. A display device comprising the organic photoelectric device according to any one of claims 1 to 14.
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| KR10-2017-0128161 | 2017-09-29 | ||
| KR1020170128161A KR102199075B1 (en) | 2017-09-29 | 2017-09-29 | Organic optoelectric device and display device |
| PCT/KR2018/010637 WO2019066315A2 (en) | 2017-09-29 | 2018-09-11 | Organic photoelectronic element and display device |
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| KR (1) | KR102199075B1 (en) |
| CN (1) | CN111095586B (en) |
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| CN110010783B (en) * | 2019-04-09 | 2021-07-20 | 江苏三月科技股份有限公司 | Tandem type organic electroluminescent device |
| CN110010784B (en) * | 2019-04-09 | 2021-07-13 | 江苏三月科技股份有限公司 | Panchromatic organic electroluminescent device containing multi-channel carrier transmission material |
| CN109928886B (en) * | 2019-04-09 | 2022-03-29 | 江苏三月科技股份有限公司 | Compound containing triarylamine and fluorene and application thereof |
| CN109994640B (en) * | 2019-04-09 | 2021-06-15 | 江苏三月科技股份有限公司 | Organic electroluminescent device containing multi-channel carrier transmission material |
| 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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| Publication number | Publication date |
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| KR102199075B1 (en) | 2021-01-07 |
| KR20190038108A (en) | 2019-04-08 |
| TWI703203B (en) | 2020-09-01 |
| CN111095586B (en) | 2023-09-01 |
| TW201920603A (en) | 2019-06-01 |
| WO2019066315A3 (en) | 2019-05-23 |
| WO2019066315A2 (en) | 2019-04-04 |
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