CN114276310B - Organic compound and application thereof - Google Patents
Organic compound and application thereof Download PDFInfo
- Publication number
- CN114276310B CN114276310B CN202111619463.2A CN202111619463A CN114276310B CN 114276310 B CN114276310 B CN 114276310B CN 202111619463 A CN202111619463 A CN 202111619463A CN 114276310 B CN114276310 B CN 114276310B
- Authority
- CN
- China
- Prior art keywords
- organic
- organic compound
- adamantyl
- unsubstituted
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 40
- 230000000903 blocking effect Effects 0.000 claims abstract description 10
- 239000000463 material Substances 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 25
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000010409 thin film Substances 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- -1 trifluoromethyl,Methoxy Chemical group 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 6
- 238000007738 vacuum evaporation Methods 0.000 abstract description 6
- 230000009477 glass transition Effects 0.000 abstract description 5
- 230000002349 favourable effect Effects 0.000 abstract description 3
- 238000005191 phase separation Methods 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 67
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 16
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 10
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 9
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 8
- 101150003085 Pdcl gene Proteins 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 125000006761 (C6-C60) arylene group Chemical group 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 125000006735 (C1-C20) heteroalkyl group Chemical group 0.000 description 3
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000011247 coating layer Substances 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 2
- 239000007769 metal material Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 description 1
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-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
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 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
- 238000007733 ion plating Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229930184652 p-Terphenyl Natural products 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 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
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 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
Abstract
The invention provides an organic compound and application thereof, wherein the organic compound has good thermal stability and film forming property, and proper glass transition temperature Tg, is favorable for forming a stable and uniform film in the thermal vacuum evaporation process, reduces phase separation, and maintains the stability of a device. The organic compound is suitable for an electron transport layer, a hole blocking layer, an organic covering layer or the like of an OLED device, so that the OLED device has higher current efficiency, lower driving voltage and longer service life.
Description
Technical Field
The invention belongs to the field of organic electroluminescent materials, and relates to an organic compound and application thereof.
Background
OLEDs have evolved over several decades with significant progress. Although the internal quantum efficiency is already close to 100%, the external quantum efficiency is only about 20%. Most of the light is confined inside the light emitting device due to substrate mode loss, surface plasmon loss, waveguide effect, and the like, resulting in a large amount of energy loss.
In the top emission device, an organic coating Layer (CPL) is deposited on a semitransparent metal electrode Al, so that the optical interference distance is adjusted, external light reflection is inhibited, extinction caused by surface plasma energy movement is inhibited, and the light extraction efficiency and the light emitting efficiency are improved. The performance requirement on CPL materials is very high: no absorption in the visible wavelength region (400 nm to 700 nm); a high refractive index (typically, n >2.1 eV), a low refractive index (typically, 1.5< n < 1.7), a low extinction coefficient (k.ltoreq.0.00) in the wavelength range 400nm to 600 nm; high glass transition temperature and molecular thermal stability (high glass transition temperature, while being vapor-deposited and without thermal decomposition).
The existing CPL material mostly adopts aromatic amine derivatives, phosphorus oxy derivatives, quinolinone derivatives and the like, has hole transmission and electron transmission functions, and improves the light extraction efficiency to a certain extent. However, in the prior art, a specific structure having a high refractive index or a material meeting specific parameter requirements is used as an organic layer covering material to improve light extraction efficiency and color purity, but the problem of both color purity and luminous efficiency has not been solved, particularly on the premise of preparing a light-emitting element by blue light.
Therefore, it is of great importance in the art for further development of CPL materials.
Disclosure of Invention
In view of the shortcomings of the prior art, the invention aims to provide an organic compound and application thereof.
To achieve the purpose, the invention adopts the following technical scheme:
it is an object of the present invention to provide an organic compound having a structure represented by the following formula I:
wherein A is selected fromAsterisks indicate the attachment site of the group;
R 1 -R 14 are identical or different and are each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl,A substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C1-C20 alkylthio group, a substituted or unsubstituted C1-C20 alkylamino group, a substituted or unsubstituted C1-C20 carbonyl-containing group, a substituted or unsubstituted C1-C20 carboxyl-containing group, or a substituted or unsubstituted C1-C20 oxycarbonyl-containing group; r is R 1 -R 14 Independently or wherein at least two adjacent are bonded to form a ring;
X 1 -X 4 the same or different, are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C60 arylene, and substituted or unsubstituted C5-C60 heteroarylene.
In the present invention, each of the C1-C20 may be independently C1, C3, C5, C6, C9, C10, C12, C13, C14, C15, C16, C18, C20, etc.
The C2-C20 can each independently be C3, C5, C6, C9, C10, C12, C13, C14, C15, C16, C18, C20, and the like.
The C3 to C30 may be C4, C6, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C29, etc. independently of each other.
The C6 to C60 may each independently be C6, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C30, C35, C38, C40, C44, C46, C48, C50, C55, C58, C59, etc.
The C5 to C60 may each independently be C6, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C30, C35, C38, C40, C44, C46, C48, C50, C55, C58, C59, etc.
The organic compound provided by the invention takes the benzoxazole structure connected with the A group as a central skeleton, can improve the light extraction efficiency and the light emitting efficiency (the most effective for blue light pixels) of the top-emission organic photoelectric device, relieves the angle dependence of the OLED device on light emission (the most effective for red/green light pixels), effectively blocks water and oxygen in the external environment, and protects the OLED display panel from being corroded by water and oxygen.
It is a second object of the present invention to provide an electroluminescent material comprising an organic compound according to one of the objects.
It is a further object of the present invention to provide an electron transport layer material comprising an organic compound according to one of the objects.
It is a fourth object of the present invention to provide a hole blocking layer material comprising an organic compound according to one of the objects.
It is a fifth object of the present invention to provide an organic cover material, characterized in that the organic cover material comprises an organic compound according to one of the objects.
It is a sixth object of the present invention to provide an OLED device comprising an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, the material of the organic thin film layer comprising the organic electroluminescent material as defined in the second object.
The seventh object of the present invention is to provide a display panel comprising the OLED device as defined in the fifth object.
An eighth object of the present invention is to provide an organic light emitting display device including the display panel as set forth in the sixth object.
Compared with the prior art, the invention has the following beneficial effects:
the organic compound provided by the invention has good thermal stability and film forming property, and proper glass transition temperature Tg, is favorable for forming a stable and uniform film in the thermal vacuum evaporation process, reduces phase separation, and maintains the stability of a device. The organic compound is suitable for an organic covering layer of an OLED device, so that the OLED device has larger light-emitting rate, lower driving voltage and longer service life.
Drawings
Fig. 1 is a schematic structural diagram of an OLED device according to an embodiment of the present invention;
FIG. 2 is a schematic structural diagram of an OLED device provided in comparative example 1;
wherein 1 is a substrate, 2 is an anode layer, 3 is a hole injection layer, 4 is a first hole transport layer, 5 is a second hole transport layer, 6 is a light emitting layer, 7 is a first electron transport layer, 8 is a second electron transport layer, 9 is a cathode, 10 is a first cap layer, 11 is a second cap layer, and the direction of the arrow represents the light emitting direction of the device.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
It is an object of the present invention to provide an organic compound having a structure represented by the following formula I:
wherein A is selected fromAsterisks indicate the attachment site of the group;
R 1 -R 14 the same or different, are each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 alkylthio, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C1-C20 carbonyl-containing group, substituted or unsubstituted C1-C20 carboxyl-containing group, or substituted or unsubstituted C1-C20 oxycarbonyl-containing group; r is R 1 -R 14 Independently or wherein at least two adjacent are bonded to form a ring;
X 1 -X 4 the same or different, are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C60 arylene, and substituted or unsubstituted C5-C60 heteroarylene.
In the present invention, each of the C1-C20 may be independently C1, C3, C5, C6, C9, C10, C12, C13, C14, C15, C16, C18, C20, etc.
The C2-C20 can each independently be C3, C5, C6, C9, C10, C12, C13, C14, C15, C16, C18, C20, and the like.
The C3 to C30 may be C4, C6, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C29, etc. independently of each other.
The C6 to C60 may each independently be C6, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C30, C35, C38, C40, C44, C46, C48, C50, C55, C58, C59, etc.
The C5 to C60 may each independently be C6, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C30, C35, C38, C40, C44, C46, C48, C50, C55, C58, C59, etc.
The organic compound provided by the invention takes the benzoxazole structure connected with the A group as a central skeleton, has good thermal stability and film forming property, and proper glass transition temperature Tg, is favorable for forming a stable and uniform film in the thermal vacuum evaporation process, reduces phase separation, and maintains the stability of a device. The light extraction efficiency and the light emitting efficiency (the most effective for blue light pixels) of the top emission organic photoelectric device can be improved, the angle dependence of the OLED device on light emission (the most effective for red/green light pixels) is relieved, water and oxygen in the external environment are effectively blocked, and the OLED display panel is protected from being corroded by water and oxygen.
In one embodiment, R 1 -R 14 Each independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, methoxy or adamantyl.
In one embodiment, X 1 -X 4 The same or different is used for the purpose of providing the same,each independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, phenyl, biphenyl, terphenyl, tetrabiphenyl, fluorenyl, or spirobifluorenyl.
In one embodiment, the biphenyl is an ortho-, meta-, or para-biphenyl group;
the terphenyl is o-terphenyl, m-terphenyl, p-terphenyl or branched terphenyl;
the tetrabiphenyl is o-tetrabiphenyl, m-tetrabiphenyl, p-tetrabiphenyl or branched-chain tetrabiphenyl;
the fluorenyl is 1-fluorenyl, 2-fluorenyl, 3-fluorenyl or 4-fluorenyl.
In one embodiment, R 1 -R 14 Is bonded to form a ring.
In one embodiment, A isWherein R is 1 、R 2 Each independently selected from fluorine, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 arylene, and substituted or unsubstituted C5-C60 heteroarylene.
In one embodiment, R 1 、R 2 Each independently selected from fluorine, methoxy, trifluoromethyl, phenyl, biphenyl, terphenyl, tetrabiphenyl, fluorenyl, spirobifluorenyl, or adamantyl.
In one embodiment, R 1 、R 2 At least one of them is adamantyl.
In one embodiment, A isWherein R is 3 -R 5 Each independently selected from fluorine, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 arylene, and substituted or unsubstituted C5-C60 heteroarylene.
In one embodiment, R 3 -R 5 Each independently selected from fluorine, methoxy, trifluoromethyl, phenyl, biphenyl, terphenyl, tetrabiphenyl, fluorenyl, spirobifluorenyl, or adamantyl.
In one embodiment, R 3 -R 5 At least one of them is adamantyl.
In one embodiment, A isWherein R is 6 -R 9 Each independently selected from fluorine, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 arylene, and substituted or unsubstituted C5-C60 heteroarylene.
In one embodiment, R 6 -R 9 Each independently selected from fluorine, methoxy, trifluoromethyl, phenyl, biphenyl, terphenyl, tetrabiphenyl, fluorenyl, spirobifluorenyl, or adamantyl.
In one embodiment, R 6 -R 9 At least one of them is adamantyl.
In one embodiment, A isWherein R is 10 -R 14 Each independently selected from fluorine, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 arylene, and substituted or unsubstituted C5-C60 heteroarylene.
In one embodiment, R 10 -R 14 Each independently selected from fluorine, methoxy, trifluoromethyl, phenyl, biphenyl, terphenyl, tetrabiphenyl, fluorenyl, spirobifluorenyl, or adamantyl.
In one embodiment, R 10 -R 14 At least one of them is adamantyl.
In one embodiment, the organic compound has a structure represented by formula II:
wherein R is 10 -R 14 Each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C1-C20 alkylthio, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C1-C20 carbonyl-containing group, substituted or unsubstituted C1-C20 carboxyl-containing group, or substituted or unsubstituted C1-C20 oxycarbonyl-containing group; and R is 10 -R 14 At least one of them is adamantyl;
X 1 -X 4 the same or different, are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C60 arylene, and substituted or unsubstituted C5-C60 heteroarylene.
In one embodiment, R 10 -R 14 Independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, adamantyl or methoxy, and R 10 -R 14 At least one of them is adamantyl.
In one embodiment, the organic compound is any one of the following compounds:
in the invention, the organic compound with the structure shown in the formula I can be prepared by the following synthetic route:
it is a second object of the present invention to provide an electroluminescent material comprising an organic compound according to one of the objects.
It is a further object of the present invention to provide an electron transport layer material comprising an organic compound according to one of the objects.
It is a fourth object of the present invention to provide a hole blocking layer material comprising an organic compound according to one of the objects.
It is a fifth object of the present invention to provide an organic cover material, characterized in that the organic cover material comprises an organic compound according to one of the objects.
It is a sixth object of the present invention to provide an OLED device comprising an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, the material of the organic thin film layer comprising the organic electroluminescent material as defined in the second object.
In one embodiment, the organic thin film layer includes a light emitting layer including the organic electroluminescent material as described in the second object as a host material.
In one embodiment, the organic thin film layer comprises an electron transport layer, and the material of the electron transport layer comprises the organic electroluminescent material as described in the second object.
In one embodiment, the organic thin film layer comprises a hole blocking layer, and the material of the hole blocking layer comprises the organic electroluminescent material as described in the second object.
In one embodiment, the OLED device further comprises an organic capping layer, the material of which comprises the organic electroluminescent material as described for two purposes.
In the OLED device provided by the invention, the anode material can be metal, metal oxide or conductive polymer; wherein the metal comprises copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum and the like and alloys thereof, the metal oxide comprises Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), zinc oxide, indium Gallium Zinc Oxide (IGZO) and the like, and the conductive polymer comprises polyaniline, polypyrrole, poly (3-methylthiophene) and the like. In addition to the above materials and combinations thereof that facilitate hole injection, materials known to be suitable as anodes are included.
In the OLED device, the cathode material may be a metal or a multi-layer metal material; wherein the metal comprises aluminum, magnesium, silver, indium, tin, titanium, etc. and their alloys, and the multilayer metal material comprises LiF/Al, liO 2 /Al、BaF 2 Al, etc. Materials suitable for use as cathodes are also known in addition to the above materials that facilitate electron injection and combinations thereof.
In the OLED device, the organic thin film layer includes at least one light emitting layer (EML) and any one or a combination of at least two of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), or an Electron Injection Layer (EIL) disposed at both sides of the light emitting layer.
The OLED device can be prepared by the following method: an anode is formed on a transparent or opaque smooth substrate, an organic thin layer is formed on the anode, and a cathode is formed on the organic thin layer. Among them, known film forming methods such as vapor deposition, sputtering, spin coating, dipping, ion plating, and the like can be used for forming the organic thin layer.
The seventh object of the present invention is to provide a display panel comprising the OLED device as defined in the fifth object.
An eighth object of the present invention is to provide an organic light emitting display device including the display panel as set forth in the sixth object.
The following are illustrative examples of the preparation of the organic compounds according to the invention:
preparation example
Synthesis of Compounds 1-56
Compounds A1 (0.5 mmol), A2 (0.75 mmol), K were prepared 2 CO 3 (0.5mmol)、PdCl 2 (5×10 - 4 mmol)、Pd(pph 3 ) 4 (5×10 -4 mmol) was added to a toluene 3mL solution, mixed, placed in a 50mL flask, and reacted at 100℃for 24 hours. Cooled to room temperature and then saturated MgSO was slowly added to the solution 4 The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to rotary evaporator to remove the solvent, followed by column chromatography to obtain the products 1 to 56.
Synthesis of Compounds 1-37
Compounds A1 (0.5 mmol), A3 (0.75 mmol), K were prepared 2 CO 3 (0.5mmol)、PdCl 2 (5×10 - 4 mmol)、Pd(pph 3 ) 4 (5×10 -4 mmol) was added to a toluene 3mL solution, mixed, placed in a 50mL flask, and reacted at 100℃for 24 hours. Cooled to room temperature and then saturated MgSO was slowly added to the solution 4 The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to rotary evaporator to remove the solvent, followed by column chromatography to obtain the products 1 to 37.
Synthesis of Compounds 1-21
Compounds A1 (0.5 mmol), A4 (0.75 mmol), K were prepared 2 CO 3 (0.5mmol)、PdCl 2 (5×10 - 4 mmol)、Pd(pph 3 ) 4 (5×10 -4 mmol) was added to a toluene 3mL solution, mixed, placed in a 50mL flask, and reacted at 100℃for 24 hours. Cooled to room temperature and then saturated MgSO was slowly added to the solution 4 The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to rotary evaporator to remove the solvent, followed by column chromatography to obtain the products 1 to 21.
Synthesis of Compounds 1-31
Compounds A1 (0.5 mmol), A5 (0.75 mmol), K were prepared 2 CO 3 (0.5mmol)、PdCl 2 (5×10 - 4 mmol)、Pd(pph 3 ) 4 (5×10 -4 mmol) was added to a toluene 3mL solution, mixed, placed in a 50mL flask, and reacted at 100℃for 24 hours. Cooled to room temperature and then saturated MgSO was slowly added to the solution 4 The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to rotary evaporator to remove the solvent, followed by column chromatography to obtain the products 1 to 31.
Synthesis of Compounds 1-57
Compounds A1 (0.5 mmol), A6 (0.75 mmol), K were prepared 2 CO 3 (0.5mmol)、PdCl 2 (5×10 - 4 mmol)、Pd(pph 3 ) 4 (5×10 -4 mmol) was added to a toluene 3mL solution, mixed, placed in a 50mL flask, and reacted at 100℃for 24 hours. Cooled to room temperature and then saturated MgSO was slowly added to the solution 4 The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to rotary evaporator to remove the solvent, followed by column chromatography to obtain the products 1 to 57.
Synthesis of Compounds 1-40
Compounds A1 (0.5 mmol), A6 (0.75 mmol), K were prepared 2 CO 3 (0.5mmol)、PdCl 2 (5×10 - 4 mmol)、Pd(pph 3 ) 4 (5×10 -4 mmol) was added to a toluene 3mL solution and mixed, placed in a 50mL flask, and thenThe reaction was carried out at 100℃for 24 hours. Cooled to room temperature and then saturated MgSO was slowly added to the solution 4 The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to rotary evaporator to remove the solvent, followed by column chromatography to obtain the products 1 to 40.
Synthesis of Compounds 1-58
Compounds A1 (0.5 mmol), A7 (0.75 mmol), K were prepared 2 CO 3 (0.5mmol)、PdCl 2 (5×10 - 4 mmol)、Pd(pph 3 ) 4 (5×10 -4 mmol) was added to a toluene 3mL solution, mixed, placed in a 50mL flask, and reacted at 100℃for 24 hours. Cooled to room temperature and then saturated MgSO was slowly added to the solution 4 The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to rotary evaporator to remove the solvent, followed by column chromatography to obtain the products 1 to 58.
Synthesis of Compounds 1-5
Compounds A1 (0.5 mmol), A8 (0.75 mmol), K were prepared 2 CO 3 (0.5mmol)、PdCl 2 (5×10 - 4 mmol)、Pd(pph 3 ) 4 (5×10 -4 mmol) was added to a toluene 3mL solution, mixed, placed in a 50mL flask, and reacted at 100℃for 24 hours. Cooled to room temperature and then saturated MgSO was slowly added to the solution 4 The aqueous solution and ethyl acetate were extracted three times, and then the organic layer was subjected to rotary evaporator to remove the solvent, followed by column chromatography to obtain the products 1 to 5.
The compounds were characterized for refractive index and the results are shown in table 1.
TABLE 1
| Compounds of formula (I) | n 460nm | n 620nm | △n |
| 1-56 | 1.60 | 1.58 | 0.02 |
| 1-37 | 1.60 | 1.58 | 0.02 |
| 1-21 | 1.61 | 1.59 | 0.02 |
| 1-31 | 1.62 | 1.60 | 0.02 |
| 1-57 | 1.60 | 1.58 | 0.02 |
| 1-40 | 1.60 | 1.58 | 0.02 |
| 1-58 | 1.61 | 1.59 | 0.02 |
| 1-5 | 1.61 | 1.59 | 0.02 |
| Comparative example 1 (D1) | 1.81 | 1.69 | 0.12 |
Wherein Deltan represents the difference in refractive index between 460nm and 620 nm.
As can be seen from the results in table 1, the compound provided by the present invention has a lower refractive index in the visible light region, and satisfies that the difference between the refractive index at 460nm wavelength and the refractive index at 620nm wavelength is 0.02, which can effectively improve color shift when multi-angle display is realized.
The following examples of applications of the organic compounds of the present invention in OLED devices are listed:
application example 1
The application example provides an organic electroluminescent device, the structure of which is shown in figure 1, and the specific preparation steps are as follows:
1) Cutting a glass substrate 1 with an Indium Tin Oxide (ITO) anode layer 2 (thickness of 15 nm) into a size of 50mm×50mm×0.7mm, respectively performing ultrasonic treatment in isopropyl alcohol and deionized water for 30 minutes, then exposing to ozone for about 10 minutes for cleaning, and mounting the cleaned substrate 1 on a vacuum deposition apparatus;
2) Evaporating a hole injection layer material compound 2 and a p-doped material compound 1 on the ITO anode layer 2 by a vacuum evaporation mode, wherein the doping proportion is 3 percent (mass ratio); a thickness of 5nm as the hole injection layer 3;
3) Vacuum evaporating a hole transport layer material compound 2 on the hole injection layer 3, wherein the thickness of the hole transport layer material compound is 100nm to serve as a first hole transport layer 4;
4) Vacuum evaporating a hole transport material compound 3 on the first hole transport layer 4 to a thickness of 5nm as a second hole transport layer 5;
5) Vacuum evaporation of a luminescent layer 6 on the second hole transport layer 5, wherein the compound 4 is used as a main material, the compound 5 is used as a doping material, the doping proportion is 3% (mass ratio), and the thickness is 30nm;
6) Vacuum evaporating an electron transport material compound 6 having a thickness of 30nm on the light-emitting layer 6 as a first electron transport layer 7;
7) Vacuum evaporation of an electron transport material compound 7 and an n-doped material compound 8 on the first electron transport layer 7, wherein the doping mass ratio is 1:1; a thickness of 5nm as a second electron transport layer 8;
8) Vacuum evaporating a magnesium-silver electrode on the second electron transport layer 8, wherein Mg: ag is 9:1, and the thickness is 10nm, and the magnesium-silver electrode is used as a cathode 9;
9) The organic small molecules D1 having a high refractive index were vacuum-deposited on the cathode 9 to a thickness of 100nm, and used as the first cap layer 10.
10 The compounds 1 to 56 of the present invention were vacuum-evaporated on the first cap layer 10 to a thickness of 20nm, and used as the second cap layer 11.
The structure of the compound used in the above steps is as follows:
application examples 2 to 11
The difference from application example 1 is only that the cap layer was prepared by replacing compounds 1 to 56 in step 10) with compounds 1 to 37, 1 to 21, 1 to 31, 1 to 58, 1 to 11, 1 to 15, 1 to 28, 1 to 30, 1 to 58, respectively, and the remaining manufacturing steps are the same, and details are shown in Table 2.
Comparative example 1
The comparative example differs from application example 1 only in that the second cap layer 11 (the structural schematic diagram of which is shown in fig. 2) is not included, and all other preparation steps are the same.
Comparative example 2
The comparative example differs from application example 1 only in that no cover layer was applied and the other preparation steps were the same.
Performing performance tests on the OLED devices prepared by the examples and the comparative examples, testing currents of the OLED devices under different voltages by using a Keithley2365A digital nano-volt meter, and dividing the currents by the light emitting areas to obtain current densities of the OLED devices under different voltages; testing the brightness and radiant energy density of the OLED device under different voltages by using a Konicaminolta CS-2000 spectroradiometer; according to the current density and brightness of the OLED device under different voltages, the OLED device with the same current density (10 mA/cm 2 ) The ignition voltage and current efficiency (CE, cd/A), V on Is the brightness of 1Cd/m 2 A lower turn-on voltage; lifetime LT95 (at 50 mA/cm) was obtained by measuring the time when the luminance of the OLED device reached 95% of the initial luminance 2 Under test conditions; the specific test result data are shown in table 2.
Table 2 results of device performance tests for application examples and comparative examples
As can be seen from table 2, it was confirmed that the efficiency can be improved by using the high refractive index and low refractive index coating layers in combination as the light efficiency improving layer. According to the results of Table 2 above, the specific organic compounds of the present invention are useful as a light source for use in a light-emitting device including an organic light-emitting deviceAn organic electronic device and a low refractive index capping layer material for an organic electronic device including the organic light emitting device. The light emitting device using the same has efficiency and driving efficiency. It can be seen that it exhibits excellent characteristics in terms of voltage, stability, etc. When the refractive index is high (n>1.69@620 nm) and the material (n) of the invention<1.69@620 nm) when used in combination with a capping layer, has higher current efficiency (5.70 cd A -1 Above) and longer life (83 h above) with lower turn-on voltage (below 4.46V). Thus, the compounds of the present invention may be used as low refractive index cladding layers in OLEDs. The method is applied to industrial organic electronic device products and improves device efficiency.
The applicant states that the organic compounds of the present invention and their use are illustrated by the above examples, but the present invention is not limited to, i.e. it is not meant that the present invention must be practiced in dependence upon the above examples. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of selected raw materials, addition of auxiliary components, selection of specific modes, etc. fall within the scope of the present invention and the scope of disclosure.
Claims (18)
1. An organic compound, characterized in that the organic compound has a structure represented by the following formula I:
wherein A is selected fromAsterisks indicate the attachment site of the group;
R 1 -R 14 identical or different, each independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, methoxy or adamantyl, and R 1 、R 2 At least one of them is adamantyl, R 3 -R 5 At least one of them is adamantyl, R 6 -R 9 At least one ofWherein R is adamantyl 10 -R 14 At least one of them is an adamantyl group,
X 1 -X 4 the same or different are respectively and independently selected from hydrogen, deuterium or trifluoromethyl.
2. The organic compound according to claim 1, wherein A isWherein R is 1 、R 2 Independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, methoxy or adamantyl, and R 1 、R 2 At least one of them is adamantyl.
3. The organic compound according to claim 1, wherein A isWherein R is 3 -R 5 Are each independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, methoxy or adamantyl, and R 3 -R 5 At least one of them is adamantyl.
4. The organic compound according to claim 1, wherein A isWherein R is 6 -R 9 Are each independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, methoxy or adamantyl, and R 6 -R 9 At least one of them is adamantyl.
5. The organic compound according to claim 1, wherein A isWherein R is 10 -R 14 Are independently selected from hydrogen, deuterium, fluorine, trifluoromethyl,Methoxy or adamantyl, and R 10 -R 14 At least one of them is adamantyl.
6. An organic compound, characterized in that the organic compound is any one of the following compounds:
7. an organic electroluminescent material, characterized in that it comprises an organic compound according to any one of claims 1 to 6.
8. An electron transport layer material, characterized in that the electron transport layer material comprises the organic compound according to any one of claims 1-6.
9. A hole blocking layer material, characterized in that it comprises an organic compound according to any one of claims 1-6.
10. An organic capping material comprising the organic compound of any one of claims 1-6.
11. An OLED device comprising an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode, wherein the material of the organic thin film layer comprises the organic electroluminescent material of claim 7.
12. The OLED device according to claim 11, wherein the organic thin film layer includes a light-emitting layer including the organic electroluminescent material according to claim 7 as a host material.
13. The OLED device of claim 11, wherein the organic thin film layer includes an electron transport layer, and wherein the material of the electron transport layer includes the organic electroluminescent material of claim 7.
14. The OLED device of claim 11, wherein the organic thin film layer includes a hole blocking layer, and wherein the material of the hole blocking layer includes the organic electroluminescent material of claim 7.
15. The OLED device of claim 11, further comprising an organic capping layer, wherein the material of the organic capping layer comprises the organic electroluminescent material of claim 7.
16. A display panel comprising an OLED device as claimed in any one of claims 11 to 15.
17. An organic light-emitting display device comprising the display panel according to claim 16.
18. An electronic device comprising the display panel of claim 16.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111619463.2A CN114276310B (en) | 2021-12-27 | 2021-12-27 | Organic compound and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111619463.2A CN114276310B (en) | 2021-12-27 | 2021-12-27 | Organic compound and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114276310A CN114276310A (en) | 2022-04-05 |
| CN114276310B true CN114276310B (en) | 2023-11-03 |
Family
ID=80876664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111619463.2A Active CN114276310B (en) | 2021-12-27 | 2021-12-27 | Organic compound and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114276310B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114907280B (en) * | 2022-04-22 | 2024-03-05 | 武汉天马微电子有限公司 | Organic compound and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021057890A1 (en) * | 2019-09-25 | 2021-04-01 | 南京明德新药研发有限公司 | 2h-benzopyran derivatives as crac inhibitors |
| CN113527280A (en) * | 2021-07-09 | 2021-10-22 | 长春海谱润斯科技股份有限公司 | Heterocyclic compound and organic electroluminescent device thereof |
-
2021
- 2021-12-27 CN CN202111619463.2A patent/CN114276310B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021057890A1 (en) * | 2019-09-25 | 2021-04-01 | 南京明德新药研发有限公司 | 2h-benzopyran derivatives as crac inhibitors |
| CN113527280A (en) * | 2021-07-09 | 2021-10-22 | 长春海谱润斯科技股份有限公司 | Heterocyclic compound and organic electroluminescent device thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114276310A (en) | 2022-04-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110028459B (en) | Compound, display panel and display device | |
| CN109608452B (en) | Organic compound, display panel, and display device | |
| CN110330472B (en) | Blue light material and preparation method and application thereof | |
| KR101429961B1 (en) | Organic Light Emitting Material and Organic Light Emitting Diode Having The Same | |
| CN110437081B (en) | Organic compound containing tricycloheptane, preparation method thereof and organic electroluminescent device comprising the same | |
| CN113937233B (en) | Organic electroluminescent device and application thereof | |
| CN111253377B (en) | Compound, display panel and display device | |
| CN113512045A (en) | Compound, material for organic electroluminescent device and application thereof | |
| CN109503466A (en) | Organic compound, display panel and display device | |
| CN109503576B (en) | Organic compound, display panel, and display device | |
| Okada et al. | A novel red organic electroluminescent device using Eu complex as an emitting layer | |
| CN114276310B (en) | Organic compound and application thereof | |
| CN111740020B (en) | High-efficiency long-service-life blue light device | |
| CN111978292B (en) | Compound and application thereof, and organic electroluminescent device comprising compound | |
| CN114478574B (en) | Organic compound and application thereof | |
| CN116283943A (en) | Organic compound, electroluminescent material and electroluminescent device | |
| CN115260114B (en) | Compound, material for organic electroluminescent device and application thereof | |
| CN114105873A (en) | Organic compound and application thereof | |
| CN109265445B (en) | Azabiphenyl organic compound, display panel and display device | |
| CN113582938A (en) | Organic compound and application thereof | |
| CN114907280B (en) | Organic compound and application thereof | |
| CN114315882B (en) | Organic compound and application thereof | |
| CN114230597B (en) | Organic compound and application thereof | |
| CN114276377B (en) | Organic compound and application thereof | |
| CN114621142B (en) | Organic compound and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |