CN113999256A - Boron-containing organic compound and light-emitting device - Google Patents
Boron-containing organic compound and light-emitting device Download PDFInfo
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- CN113999256A CN113999256A CN202111418443.9A CN202111418443A CN113999256A CN 113999256 A CN113999256 A CN 113999256A CN 202111418443 A CN202111418443 A CN 202111418443A CN 113999256 A CN113999256 A CN 113999256A
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 229910052796 boron Inorganic materials 0.000 title claims abstract description 39
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 125000003118 aryl group Chemical group 0.000 claims abstract description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 23
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 14
- 239000012044 organic layer Substances 0.000 claims abstract description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims abstract description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract description 4
- -1 n-octyl Chemical group 0.000 claims description 134
- 125000004431 deuterium atom Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 7
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 7
- 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 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 5
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 5
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 2
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 claims description 2
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000006038 hexenyl group Chemical group 0.000 claims description 2
- 125000005980 hexynyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 claims description 2
- 125000005071 nonynyl group Chemical group C(#CCCCCCCC)* 0.000 claims description 2
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 claims description 2
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 claims description 2
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 claims description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 claims description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 2
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- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 abstract 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
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Abstract
The invention discloses a boron-containing organic compound and a light-emitting device, wherein the boron-containing organic compound comprises a compound shown in any one of formulas (I) to (III):
R1～R14are respectively selected from any one of the following groups: hydrogen, deuterium, halogen, cyano, NO2，N(R)2，OR，SR，C(＝O)R，P(＝O)R，Si(R)3Substituted or unsubstituted C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C6-C40 aryl, and C5-C40 heteroaryl; m is substituted or unsubstituted aryl of C6-C48; x1、X2Are respectively selected from any one of the following groups: o, S, N-Y, C (Y)2(ii) a Y is selected from any one of the following groups: getSubstituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C40 aryl or substituted or unsubstituted C5-C40 heteroaryl. The light-emitting device includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer contains at least one of the boron-containing organic compounds.
Description
Technical Field
The invention relates to the technical field of organic photoelectricity, in particular to a boron-containing organic compound and a light-emitting device.
Background
The organic electroluminescent device has a series of advantages of self-luminescence, low-voltage driving, full curing, wide visual angle, simple composition and process and the like; in contrast to liquid crystal displays, organic electroluminescent devices do not require a backlight. Therefore, the organic electroluminescent device has wide application prospect.
Organic electroluminescent devices generally comprise an anode, a metal cathode and an organic layer sandwiched therebetween. The organic layer mainly comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer. In addition, a host-guest structure is often used for the light-emitting layer. That is, the light emitting material is doped in the host material at a certain concentration to avoid concentration quenching and triplet-triplet annihilation, improving the light emitting efficiency. In the structure of the organic electroluminescent device, if a voltage is applied between two electrodes, electrons and holes are injected and transported from the cathode and the anode, respectively, into the light emitting layer to form excitons, and the excitons emit light when falling to the ground state again.
In recent years, some properties peculiar to boron element make boron-containing pi-conjugated materials attract great research interest. In molecular design, by reasonably utilizing the characteristics of boron element and introducing the boron element to different positions of a pi-conjugated system, new organic pi-conjugated materials with different structural types and unique photoelectric properties can be obtained, such as electron transport materials and luminescent materials in organic electroluminescent devices, chemical sensor materials, organic photovoltaic materials and the like.
The currently commercially used blue-light boron-nitrogen-based material is a thermally excited delayed fluorescence material (MR-TADF) with a relatively hot multiple resonance, and although theoretically, the material can utilize triplet state to increase the exciton utilization rate to 100%, the currently commercially used blue-light boron-nitrogen-based triplet exciton has a too long lifetime, which results in a short device lifetime and a large efficiency roll-off at high current density, so that many panel manufacturers mostly select a method for increasing the device lifetime and reducing the device efficiency, that is, only use the singlet state luminescence of the material. How to industrially use triplet excitons of such materials to improve device efficiency and ensure a longer device lifetime still faces many key problems; in addition, the current commercial blue-light boron-nitrogen molecules have good planar structures, so that the self-quenching effect is very serious under high-concentration doping, devices are generally required to be prepared under extremely low doping concentration, and the operability of the process is seriously influenced.
Disclosure of Invention
The invention provides a boron-containing organic compound and a luminescent device, wherein a steric hindrance group and a low triplet state group are introduced: 1) the introduction of the steric hindrance group to form a twisted three-dimensional structure can effectively avoid the occurrence of concentration quenching effect caused by the self planar structure of the thermal excitation delay fluorescent material with multiple resonances; 2) the introduction of low triplet state groups can effectively reduce the triplet state energy of the boron-containing organic compound, increase the energy difference between the singlet state and the triplet state of the material, effectively inhibit long-life triplet state excitons from returning to the singlet state through the process of intersystem crossing, prevent the formation of the long-life excitons, further improve the performance of the device and ensure the long service life of the device.
To achieve the above object, as an embodiment of one aspect of the present invention, there is provided a boron-containing organic compound including a compound represented by any one of formulae (I) to (III):
R1～R14are respectively selected from any one of the following groups: hydrogen atom, deuterium atom, halogen, cyano group, NO2、N(R)2、OR、SR、C(＝O)R、P(＝O)R、Si(R)3The compound is characterized by comprising a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C40 aryl group and a substituted or unsubstituted C5-C40 heteroaryl group, wherein R is selected from any one of the following groups: hydrogen atom, deuterium atom, fluorine atom, cyano group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstitutedSubstituted aryl of C6-C30, substituted or unsubstituted heteroaryl of C5-C30; m is substituted or unsubstituted aryl of C6-C48; x1、X2Are respectively selected from any one of the following groups: o, S, N-Y, C (Y)2Wherein Y is selected from any one of the following groups: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C40 aryl or substituted or unsubstituted C5-C40 heteroaryl.
As an embodiment of another aspect of the present invention, there is provided a light-emitting device including a first electrode, a second electrode, and an organic layer provided between the first electrode and the second electrode, the organic layer containing at least one of the above boron-containing organic compounds.
According to the invention, by introducing the aromatic group into the para position of the boron element, under the conditions of narrow luminous peak, high thermal stability, good transmission performance and high fluorescence quantum yield of the boron-containing compound, the exciton utilization rate of the compound is improved through a triplet state-triplet state quenching (TTA) effect, and the device efficiency is finally improved.
Drawings
FIG. 1 is a fluorescence spectrum of compounds 1-1 and BD2 in a toluene solution in examples of the present invention;
FIG. 2 is a fluorescence spectrum of compounds 2-6, 2-1 and BD1 in a toluene solution in examples of the present invention;
fig. 3 is a configuration diagram of an organic electroluminescent device in an embodiment of the present invention.
Reference numerals:
1-substrate, 2-anode, 3-hole injection layer, 4-hole transport layer, 5-electron blocking layer, 6-luminescent layer, 7-hole blocking layer, 8-electron transport layer, 9-electron injection layer and 10-cathode.
Detailed Description
In order that the objects, technical solutions and advantages of the present invention will become more apparent, the present invention will be further described in detail with reference to the accompanying drawings in conjunction with the following specific embodiments.
The p pi-pi conjugation effect between the empty p orbitals of boron atoms and the pi orbitals of the pi-conjugated system can lead the boron to be introduced into the pi-conjugated system to endow the system with some unique photoelectric properties. The method for constructing the pi-conjugated photoelectric functional material by using boron mainly comprises the following three characteristics of boron elements: (1) special orbital interactions: the p orbital of the outermost empty boron element and the pi orbital of a pi-conjugated system can form p pi-pi conjugate, so that the lowest unoccupied orbital (LUMO) energy level of the system is reduced; (2) lewis acidity: due to the existence of an empty p orbit, boron is easy to complex with Lewis base (such as fluorine ions) and breaks p pi-conjugation, thereby causing the obvious change of the photoelectric property of a corresponding system; (3) large steric hindrance effects: due to the presence of empty p orbitals, it is generally necessary to introduce bulky aromatic groups on the boron atom in order to increase the stability of the organoboron pi-conjugated compounds.
According to one aspect of the present general inventive concept, there is provided a boron-containing organic compound including a compound represented by any one of formulae (I) to (III):
R1～R14are respectively selected from any one of the following groups: hydrogen atom, deuterium atom, halogen, cyano group, NO2、N(R)2、OR、SR、C(＝O)R、P(＝O)R、Si(R)3The compound is characterized by comprising a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C6-C40 aryl group and a substituted or unsubstituted C5-C40 heteroaryl group, wherein R is selected from any one of the following groups: a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C5-C30 heteroaryl group; m is substituted or unsubstituted aryl of C6-C48; x1、X2Are respectively selected from any one of the following groups: o, S, N-Y, C (Y)2Wherein Y is selected from any one of the following groups: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C40 aryl or substituted or unsubstituted C5-C40 heteroaryl.
According to the invention, an aromatic group is introduced on the boron element, and the conjugated system has photoelectric property through p pi-pi conjugation formed between the outermost empty p orbit and the pi orbit of the pi-conjugated system, so that the boron-containing compound has the advantages of narrow light-emitting peak, high thermal stability, good transmission performance and high fluorescence quantum yield.
In the present invention, the term "substituted or unsubstituted" means that a group or ring system may be substituted with one or more groups or ring systems, or may remain unsubstituted.
According to the embodiment of the present invention, the boron-containing organic compound may have a structure represented by the following general formulae (S-1) to (S-6) (not limited thereto), wherein when N-Y is simultaneously used in the general formula (S-6), Y' S may be the same or different. Preferably, Y is independently selected from any one of the following groups: substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, and substituted or unsubstituted C5-C18 heteroaryl.
According to an embodiment of the present invention, R1～R14Selected from any one of the following groups: substituted or unsubstituted alkyl, preferably C1 to C6; substituted or unsubstituted alkenyl, preferably C2 to C6; substituted or unsubstituted alkynyl, preferably C2 to C6; substituted or unsubstituted aryl, preferably C6 to C18; substituted or unsubstituted heteroaryl, preferably C5-C18.
According to an embodiment of the invention, the heteroatom in the heteroaryl group from C5 to C40 is selected from any one of the following: n, O, S, P, As, Si, preferably N, O, S; the number of hetero atoms in the C5-C40 heteroaryl group is 1-10, preferably 1-5.
According to the embodiment of the invention, the aryl of C6-C48 in M is selected from any one of the following: a benzene ring of a monocyclic system, a biphenyl ring of a bicyclic system, a naphthalene ring of a condensed bicyclic system, a terphenyl ring of a tricyclic system (m-terphenyl group, o-terphenyl group, p-terphenyl group), an acenaphthene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, fluoranthene of a tricyclic system, a triphenylene ring, a pyrene ring, a tetracene ring of a tricyclic system, a perylene ring of a pentacene ring of a system.
According to an embodiment of the invention, the boron-containing organic compound of the invention is selected from any one of the following compounds:
according to an embodiment of the invention, M is selected from any one of the following groups:
wherein A is1～A6，B1～B9，C1～C8，D1～D9，E1～E6，F1～F7，G1～G10，H1～H9，K1～K12，L1～L6，M1～M12，N1～N10，O1～O17，P1～P15，Q1～Q15，I1～I15,R1～R15，S1～S13，T1～T13，U1～U12，V1～V12，W1～W17，X1～X15，Y1～Y15，Z1～Z15，J1～J15，Aa1～Aa15，Bb1～Bb15，Cc1～Cc16，Dd1～Dd15，Ee1～Ee15，Ff1～Ff15，Gg1～Gg15，Hh1～Hh17，Ii1～Ii15，Jj1～Jj15Are respectively selected from any one of the following groups: a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C5-C30 heteroaryl group.
According to the embodiments of the present invention, the "position of the dotted line is movable" means that a group has a plurality of different positions, such as one position and two positions, which can be connected to the main body portion.
According to an embodiment of the invention, the alkyl of C1-C20 is selected from any one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, 2-methylhexyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, 3-methylheptyl, n-nonyl, n-decyl, hexadecyl, octadecyl, eicosyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl.
According to an embodiment of the invention, the alkyl group of C1-C20 is linear, branched or cyclic.
According to an embodiment of the invention, the alkenyl of C2-C20 is selected from any one of the following groups: vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, 2-ethylhexenyl, allyl, or cyclohexenyl.
According to embodiments of the present invention, the alkenyl group of C2 to C20 is linear, branched, or cyclic.
According to an embodiment of the invention, the alkynyl group of C2-C20 is selected from any one of the following groups: ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl.
According to an embodiment of the invention, the alkynyl group of C2 to C20 is linear, branched or cyclic.
According to an embodiment of the invention, the aryl group of C6-C40 is selected from any one of the following groups: phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, perylenyl, anthryl, benzofluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, pentabiphenyl, terphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, cis-or trans-monobenzindenofluorenyl, cis-or trans-dibenzoindenofluorenyl, trimeric indenyl, isotridecylindenyl, spirotrimeric indenyl, spiroisotridecylindenyl.
According to the embodiment of the invention, the aryl of C6-C40 is preferably phenyl, naphthyl, anthryl, phenanthryl, benzanthryl and benzophenanthryl.
According to an embodiment of the invention, the heteroaryl of C5-C40 is selected from any one of the following groups: furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, indolocarbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthraoxazolyl, phenanthrooxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, thiazoyl, phenanthroimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthoxazolyl, and a naphthoxazolyl, Benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazanthryl, 2, 7-diazylpyryl, 2, 3-diazylpyryl, 1, 6-diazylpyryl, 1, 8-diazylpyryl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluoresceinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,3, 4-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl and the like, preferably phenyl, naphthyl, anthryl, phenanthryl, benzanthryl, benzophenanthryl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl.
According to the embodiment of the invention, the heteroaryl of C6-C40 is preferably furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl or carbazolyl, and more preferably carbazolyl.
According to the embodiment of the invention, the substituent of the substituted aryl of C6-C40 and the substituted heteroaryl of C5-C40 is selected from any one of the following groups: deuterium atom, halogen, amino group, hydroxyl group, cyano group, C1-C6 alkyl group.
According to the embodiment of the invention, the number of the substituents in the aryl group of C6-C40 and the heteroaryl group of C5-C40 is 1-5, and the preferable number is 1-3.
According to an embodiment of the invention, the C1-C6 alkyl is selected from any one of the following groups: methyl, tert-butyl.
The present invention will be described in detail with reference to specific examples.
Synthesis of Compound 1-1 Using the following synthetic route
The method comprises the following steps: synthesis of intermediate 1-1
To a three-necked flask equipped with a reflux condenser tube, 5-bromo-1, 3-difluoro-2-iodobenzene (15.9g, 50.0mmol), 3, 6-di-tert-butylcarbazole (27.86g, 100.0mmol), sodium hydride (3.00g, 125.0mmol) and DMF (200mL) were added in this order under a nitrogen atmosphere, and heated under reflux for 6 h. After the reaction was completed, the system was cooled to room temperature. Adding a large amount of water to generate white precipitate, and performing suction filtration and collection. The precipitate was washed successively with water and 50% by volume of methanol solution. Finally, the obtained filter cake is dissolved in a proper amount of dichloromethane and further purified by column chromatography (mobile phase is petroleum ether and dichloromethane in a volume ratio of 3: 1) to obtain 37.6g of white solid with a yield of 90%.
The mass spectrum detection result of the obtained sample is as follows: MS (EI) M/z 836.22[ M ]+]；C46H50BIN2Calculated in percent C, 65.95; h, 6.02; n, 3.34; found C, 65.92; h, 5.99; and N, 3.31.
Step two: synthesis of intermediate 1-1-2
To a three-necked flask equipped with a reflux condenser tube, intermediate 1-1-1(37.6g, 50.0mmol) and anhydrous m-xylene (m-xylene) (300mL) were sequentially added under a nitrogen atmosphere, and the system was cooled to-40 ℃. N-butyllithium (25mL, 60mmol, 2.4M) was added dropwise to the system, and after completion of the addition, stirring was continued at that temperature for 2h, and boron tribromide (19.0g, 75mmol) was added dropwise. After the addition was complete, the reaction was continued at 50 ℃ for 4 h. The system was then cooled to 0 deg.C, N-ethyldiisopropylamine (13.5g, 100mmol) was added, after which the temperature was gradually raised to 125 deg.C and the reaction continued at this temperature for 12 h. After the reaction is finished, the solvent is evaporated under reduced pressure, and the crude product is purified by column chromatography (the mobile phase is petroleum ether and dichloromethane in a volume ratio of 9: 1) to obtain 19.4g of yellow solid with the yield of 60%.
The mass spectrum detection result of the obtained sample is as follows: MS (EI) M/z 720.31[ M ]+]；C46H48BBrN2Calculated in percent C, 76.78; h, 6.72; n, 3.89; found C, 76.73; h, 6.69; n, 3.84.
Step three: synthesis of Compound 1-1
Under nitrogen, 3.6g (5.0mmol) of intermediate 1-1-2, 1.3g (12.4mmol) of anhydrous sodium carbonate, 2.5g (5.3mmol) of deuterated phenyl boronate, 68.3mg (0.06mmol) of tetrakis (triphenylphosphine) palladium and 45mL of a mixed solvent (30: 8: 7 by volume of toluene: water: ethanol) are sequentially added into a clean 100mL three-necked flask, and the system is heated to reflux and reacted under reflux overnight. After the reaction is finished, stopping heating, and automatically cooling the reaction system to room temperature. The reaction solution was poured into about 200mL of water and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and further purified by column chromatography (350 mesh silica gel, mobile phase petroleum ether and dichloromethane in a volume ratio of 3: 2) to give 3.5g of a yellow solid in 80% yield.
The mass spectrum detection result of the obtained sample is as follows: ms (ei): m/z 897.53[ M+]. Calculated value of elemental analysis C66H56D5BN2(%): c, 88.27; h, 7.41; b, 1.20; n, 3.12; measured value: c, 88.23; h, 7.37; b, 1.15; and N, 3.07.
Compounds 2-6 were synthesized using the following route
The method comprises the following steps: synthesis of intermediate 2-6-1
To a three-necked flask equipped with a reflux condenser tube, 5-bromo-1, 3-difluoro-2-iodobenzene (15.9g, 50.0mmol), bis (4-tert-butylphenyl) amine (28.07g, 100.0mmol), sodium hydride (3.00g, 125.0mmol) and DMF (200mL) were added in this order under a nitrogen atmosphere, and heated under reflux for 6 h. After the reaction was completed, the system was cooled to room temperature. Adding a large amount of water to generate white precipitate, and performing suction filtration and collection. The precipitate was washed successively with water and 50% by volume of methanol solution. Finally, the obtained filter cake is dissolved in a proper amount of dichloromethane and further purified by column chromatography (mobile phase is petroleum ether and dichloromethane in a volume ratio of 3: 1) to obtain 39g of white solid with a yield of 95%.
The mass spectrum detection result of the obtained sample is as follows: MS (EI) M/z 840.25[ M ]+]；C46H54BrIN2(%) calculated C, 65.64; h, 6.47; n, 3.33; found C, 65.59; h, 6.45; and N, 3.31.
Step two: synthesis of intermediate 2-6-2
To a three-necked flask equipped with a reflux condenser tube, intermediate 2-6-1(39g, 46.33mmol) and anhydrous m-xylene (m-xylene) (300mL) were sequentially added under a nitrogen atmosphere, and the system was cooled to-40 ℃. N-butyllithium (25mL, 60mmol, 2.4M) was added dropwise to the system, and after completion of the addition, stirring was continued at that temperature for 2h, and boron tribromide (19.0g, 75mmol) was added dropwise. After the addition was complete, the reaction was continued at 50 ℃ for 4 h. The system was then cooled to 0 deg.C, N-ethyldiisopropylamine (13.5g, 100mmol) was added, after which the temperature was gradually raised to 125 deg.C and the reaction continued at this temperature for 12 h. After the reaction is finished, the solvent is evaporated under reduced pressure, and the crude product is purified by column chromatography (the mobile phase is petroleum ether and dichloromethane in a volume ratio of 9: 1) to obtain 20.11g of yellow solid with the yield of 60%.
The mass spectrum detection result of the obtained sample is as follows: MS (EI) M/z 722.34[ M ]+]；C46H52BBrN2Calculated in percent C, 76.78; h, 6.72; n, 3.89; found 76.75 for C; h, 6.65; and N, 3.87.
Step three: synthesis of Compounds 2 to 6
Under nitrogen, 3.62g (5.0mmol) of intermediate 2-6-2, 1.3g (12.4mmol) of anhydrous potassium carbonate, 1.9g (5.00mmol) of 1-perylene boronate, 68.3mg (0.06mmol) of tetrakis (triphenylphosphine) palladium and 45mL of a mixed solvent (30: 8: 7 by volume of toluene: water: ethanol) are sequentially added into a clean 100mL three-necked flask, and the system is heated to reflux and reacted under reflux overnight. After the reaction is finished, stopping heating, and automatically cooling the reaction system to room temperature. The reaction solution was poured into about 200mL of water and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and further purified by column chromatography (350 mesh silica gel, eluent petroleum ether and dichloromethane at a volume ratio of 3: 2) to give 2.7g of a yellow solid with a yield of 60%.
The mass spectrum detection result of the obtained sample is as follows: ms (ei): m/z 890.23[ M+]. Calculated value of elemental analysis C66H59BN2(%): c, 88.97; h, 6.67; n, 3.14; measured value: c, 88.80; h, 6.61; and N, 3.10.
Synthesis of Compound 2-1 Using the following route
Under nitrogen, 3.62g (5.0mmol) of intermediate 2-6-2, 1.3g (12.4mmol) of anhydrous sodium carbonate, 1.64g (5.00mmol) of 1-pyreneboronic acid, 68.3mg (0.06mmol) of tetrakis (triphenylphosphine) palladium and 45mL of a mixed solvent (toluene: water: ethanol in a volume ratio of 30: 8: 7) were sequentially added to a clean 100mL three-necked flask, and the system was heated to reflux and reacted overnight under reflux. After the reaction is finished, stopping heating, and automatically cooling the reaction system to room temperature. The reaction solution was poured into about 200mL of water and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and further purified by column chromatography (350 mesh silica gel, eluent petroleum ether: dichloromethane in a volume ratio of 3: 2) to give 2.5g of a yellow solid with a yield of 60%.
The mass spectrum detection result of the obtained sample is as follows: ms (ei): m/z 844.49[ M+]. Calculated value of elemental analysis C62H61BN2(%): c, 88.13; h, 7.28; n, 3.32; measured value: c, 88.10; h, 7.26; and N, 3.27.
Compounds 2-7 were synthesized using the following route
Under nitrogen, 3.62g (5.0mmol) of intermediate 2-6-2, 1.3g (12.4mmol) of anhydrous sodium carbonate, 1.80g (5.00mmol) of 9,9' -spirobifluorene-3-boronic acid, 68.3mg (0.06mmol) of tetrakis (triphenylphosphine) palladium and 45mL of a mixed solvent (30: 8: 7 by volume of toluene: water: ethanol) were sequentially added to a clean 100mL three-necked flask, and the system was heated to reflux and reacted overnight under reflux. After the reaction is finished, stopping heating, and automatically cooling the reaction system to room temperature. The reaction solution was poured into about 200mL of water and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and further purified by column chromatography (350 mesh silica gel, eluent petroleum ether: dichloromethane in a volume ratio of 3: 2) to give 3.1g of a yellow solid in 65% yield.
The mass spectrum detection result of the obtained sample is as follows: ms (ei): m/z 958.49[ M+]. Calculated value of elemental analysis C71H67BN2(%): c, 88.91; h, 7.04; n, 2.92; measured value: c, 88.90; h, 7.02; and N, 2.90.
According to the present general inventive concept in another aspect of the present invention, there is provided a light emitting device including a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, the organic layer containing at least one of the above boron-containing organic compounds therein.
The boron-containing organic compound can be used for organic electroluminescent devices, organic solar cells, organic diodes and the like. The organic light-emitting device prepared from the polycyclic boron-containing compound has the advantages of high light-emitting efficiency, long service life, low driving voltage, narrow half-peak width, high color purity and the like, is an organic electroluminescent material with excellent performance, and finally, in the OLED device, the device performance of the material is further improved.
Fig. 3 is a configuration diagram of an organic electroluminescent device in an example of the present invention. As shown in fig. 3, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10 are sequentially provided on a substrate 1.
According to an embodiment of the present invention, an organic electroluminescent device may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. The specific manufacturing process is as follows: an anode is formed by depositing metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method, an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and a substance which can be used as a cathode is deposited on the organic layer.
According to the embodiment of the present invention, the organic electroluminescent device may be configured in such a manner that the hole injection layer 3 between the anode 2 and the hole transport layer 4, the hole blocking layer 7 between the light emitting layer 6 and the electron transport layer 8, and the electron injection layer 9 between the electron transport layer 8 and the cathode 10 are omitted, and the anode 2, the hole transport layer 4, the light emitting layer 6, the electron transport layer 8, and the cathode 10 are sequentially disposed on the substrate 1.
According to the embodiment of the invention, the anode material of the organic electroluminescent device is selected from any one of the following materials: (1) metals such as vanadium, chromium, copper, zinc, gold, etc., or alloys thereof, e.g., zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), ZnO: Al, SnO2Sb; (2) conductive polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-bis)Oxy) thiophene](PEDOT), polypyrrole and polyaniline. Preferably Indium Tin Oxide (ITO).
According to the embodiment of the present invention, the material of the hole injection layer of the organic electroluminescent device is selected from any one of the following: porphyrin compounds represented by copper phthalocyanine, naphthalene diamine derivatives, star-shaped triphenylamine derivatives, arylamine compounds having a structure in which more than 3 triphenylamine structures are connected by single bonds or divalent groups containing no heteroatom in the molecule, triphenylamine trimers and tetramers, hexacyanoazatriphenylene receptor-type heterocyclic compounds, and coating-type high-molecular materials. The hole injection layer material of the organic electroluminescent device can be formed into a thin film by an evaporation method, a spin coating method, or an ink jet method.
According to the embodiment of the present invention, the material of the hole transport layer of the organic electroluminescent device is selected from any one of the following materials: (1) m-carbazolylphenyl-containing compounds, such as N, N ' -diphenyl-N, N ' -di (m-tolyl) benzidine (TPD), N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), (2) benzidine derivatives, such as N, N ' -tetrabiphenylylbenzidine; (3)1, 1-bis [ (di-4-tolylamino) phenyl ] cyclohexane (TAPC); (4) various triphenylamine trimers and tetramers; (4)9,9',9 "-triphenyl-9H, 9' H, 9" H-3,3':6',3 "-tricarbazole (Tris-PCz). The above materials may be used in the form of a single layer formed by separately forming a film or by mixing with other materials to form a film, or may be used in the form of a laminated structure of layers formed by separately forming a film, a laminated structure of layers formed by mixing films, or a laminated structure of layers formed by separately forming a film and layers formed by mixing films. The above materials can be formed into a thin film by a vapor deposition method, a spin coating method, an ink jet method, or the like.
According to the embodiment of the present invention, in the hole injection layer or the hole transport layer of the organic electroluminescent element, a material obtained by p-doping a material generally used in the layer with tribromoaniline hexaantimony chloride, an axial olefin derivative, or the like, a polymer compound having a structure of a benzidine derivative such as TPD in a partial structure thereof, or the like can be used.
According to the embodiment of the invention, the material of the electron blocking layer of the organic electroluminescent device is selected from any one of the following materials: carbazole derivatives such as 3,3' -bis (N-carbazolyl) -1,1' -biphenyl (mCBP), 4',4 ″ -tris (N-carbazolyl) triphenylamine (TCTA), 9-bis [4- (carbazol-9-yl) phenyl ] fluorene, 1, 3-bis (carbazol-9-yl) benzene (mCP), and 2, 2-bis (4-carbazol-9-ylphenyl) adamantane (Ad-Cz); a compound having a triphenylsilyl and triarylamine structure represented by 9- [4- (carbazol-9-yl) phenyl ] -9- [4- (triphenylsilyl) phenyl ] -9H-fluorene; monoamine compounds having a high electron-blocking property, various triphenylamine dimers, and the like. The above-mentioned materials may be used in the form of a single layer formed by film formation alone or by mixing with other materials, or may be used in the form of a laminated structure of layers formed by film formation alone, a laminated structure of layers formed by mixing into films, or a laminated structure of layers formed by film formation alone and layers formed by mixing into films. These materials can be formed into a thin film by a method such as vapor deposition, spin coating, or ink jet.
According to the embodiment of the present invention, the material of the light emitting layer of the organic electroluminescent device is selected from any one of the following: a light-emitting material comprising an organic electroluminescent compound (boron-containing organic compound) represented by the formulae (I) to (III) and Alq3Various metal complexes such as metal complexes of a first hydroxyquinoline derivative, compounds having a pyrimidine ring structure, anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, and polyparaphenylene vinylene derivatives.
According to an embodiment of the present invention, the light emitting layer of the organic electroluminescent device may be composed of a host material and a dopant material. The host material may be selected from any one of: mCBP, mCP, anthracene derivatives, thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, heterocyclic compounds having a partial structure in which an indole ring is a condensed ring, and the like. The doping material may be selected from any of the following: pyrene derivatives, anthracene derivatives, quinacridones, coumarins, rubrene, perylenes and their derivatives, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives, spirobifluorene derivatives, and the like, and light-emitting materials containing organic electroluminescent compounds represented by formulae (I) to (iii) (boron-containing organic compounds) are preferred. The doping weight ratio of the organic electroluminescent compound of the present invention is preferably 0.1 to 50%, more preferably 0.2 to 20%, and particularly preferably 0.5 to 10%.
According to the embodiment of the present invention, the material of the hole blocking layer of the organic electroluminescent device is selected from any one of the following materials: metal complexes of quinolyl derivatives such as 2,4, 6-tris (3-phenyl) -1,3, 5-triazine (T2T), 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBi), aluminum (III) bis (2-methyl-8-hydroxyquinoline) -4-phenylphenate (BAlq), and various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, and the like. The above-mentioned materials may be used as a single layer formed by mixing them with other materials, or may be used as a laminated structure of layers formed by forming films separately, a laminated structure of layers formed by mixing them together, or a laminated structure of layers formed by forming films separately and layers formed by mixing them together. These materials can be formed into a thin film by a method such as vapor deposition, spin coating, or ink jet.
According to the embodiment of the invention, the material of the electron transport layer of the organic electroluminescent device is selected from any one of the following materials: alq3Metal complexes of quinolinol derivatives including BAlq; various metal complexes; a triazole derivative; a triazine derivative; an oxadiazole derivative; a pyridine derivative; bis (10-hydroxybenzo [ H ]]Quinoline) beryllium (Be (bq)2) ); such as 2- [4- (9, 10-dinaphthalen-2-anthracen-2-yl) phenyl]Benzimidazole derivatives such as-1-phenyl-1H-benzimidazole (ZADN); a thiadiazole derivative; an anthracene derivative; a carbodiimide derivative; quinoxaline derivatives; pyridoindole derivatives; phenanthroline derivatives; silole derivatives and the like. The above-mentioned materials may be used as a single layer formed by mixing them with other materials, or may be used as a laminated structure of layers formed by forming films separately, a laminated structure of layers formed by mixing them together, or a laminated structure of layers formed by forming films separately and layers formed by mixing them together. These materials can be formed into a thin film by a method such as vapor deposition, spin coating, or ink jet.
According to the embodiment of the present invention, the material of the electron injection layer of the organic electroluminescent device is selected from any one of the following materials: alkali metal salts such as lithium fluoride and cesium fluoride; alkaline earth metal salts such as magnesium fluoride; metal complexes of quinolinol derivatives such as lithium quinolinol; and metal oxides such as alumina.
In the electron injection layer or the electron transport layer of the organic electroluminescent device according to the embodiment of the present invention, a material obtained by further N-doping a metal such as cesium or a triarylphosphine oxide derivative may be used as a material generally used for the layer.
According to the embodiment of the invention, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer and the electron transport layer of the organic electroluminescent device
According to the embodiment of the invention, the material of the cathode of the organic electroluminescent device is selected from any one of the following materials: electrode materials having a low work function such as aluminum, magnesium, or alloys having a low work function such as magnesium-silver alloy, magnesium-indium alloy, aluminum-magnesium alloy are used as the electrode materials.
According to the embodiment of the invention, the substrate of the organic electroluminescent device can be a substrate in a traditional organic electroluminescent device, such as glass or plastic, and preferably a glass substrate.
The organic electroluminescent device according to the present invention will be described in detail with reference to specific examples.
Preparation of organic electroluminescent device 1 (organic EL device 1)
A hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9 and a cathode 10 were sequentially formed on a transparent anode 2 previously formed on a glass substrate 1 to prepare an organic electroluminescent device as shown in fig. 3. The preparation process comprises the following steps: the glass substrate on which the ITO film with the film thickness of 100nm is formed is subjected to ultrasonic treatment in Decon 90 alkaline cleaning solution, washed in deionized water, washed three times in acetone and ethanol respectively, baked in a clean environment until the moisture is completely removed, cleaned by ultraviolet light and ozone, and the surface is bombarded by low-energy cation beams. Placing the glass substrate with ITO electrode into a vacuum chamber, and vacuumizing to 4 × 10-4～2×10-5Pa. Then, on the glass substrate with the ITO electrode, vapor deposition was performed at 0.2nm/s50% HIL 1/50% HTL1 was vapor-deposited at a rate to form a layer having a film thickness of 10nm as a hole injection layer. On the hole injection layer, HTL1 was deposited at a deposition rate of 2.0nm/s to form a layer having a thickness of 30nm as a hole transport layer. Three-source co-evaporation was performed on the hole transport layer at respective evaporation rates of BH1 and 5Cz-TRZ as host materials of 1.6nm/s and 0.4nms and at a rate of 1-1 as a dopant of 0.04nm/s to form a layer having a thickness of 20nm as a light-emitting layer, with the doping weight ratio of 1-1 being 2 wt%. HBL1 was deposited on the light-emitting layer at a deposition rate of 2.0nm/s to form a layer having a thickness of 20nm as a hole-blocking layer. 50% ETL 1/50% Liq was vapor-deposited on the hole block at a vapor deposition rate of 2.0nm/s to form a layer having a thickness of 40nm as an electron transport layer. 8-hydroxyquinoline-lithium (Liq) was vapor-deposited on the electron transport layer at a vapor deposition rate of 0.2nm/s to form a layer having a thickness of 2nm as an electron injection layer. Finally, aluminum was deposited at a deposition rate of 3.0nm/s or more to form a cathode having a film thickness of 100 nm.
Preparation of organic electroluminescent devices 2 to 3 (organic EL devices 2 to 3)
Comparative organic electroluminescent device preparation of comparative examples 1 to 2
Comparative organic EL devices 1 to 2 were produced under the same conditions as the organic EL device 1 except that the compounds in table 1 below were used instead of the compounds in each layer of the organic electroluminescent device 1 (organic EL device 1).
TABLE 1
The examples relate to compounds having the following structure:
the light emission characteristics of the organic EL devices 1 to 3 and comparative examples 1 to 2 of the organic EL devices manufactured in comparative examples 1 to 2 were measured at normal temperature in the atmosphere when a direct current voltage was applied. The measurement results are shown in tables 2 and 3.
TABLE 2
TABLE 3
The current-luminance-voltage characteristics of the device were obtained from a Keithley source measuring system (Keithley 2400 Sourcemeter, Keithley 2000 Currentmeter) with calibrated silicon photodiodes, the electroluminescence spectra were measured by a Photo research PR655 spectrometer, and the external quantum efficiencies of the devices were calculated by the method of the documents adv.mater, 2003,15, 1043-.
As can be seen from table 2 and fig. 1, compared with BD2, in the boron-containing compound 1-1 of the present invention, by introducing low triplet deuterated phenylanthracene to the p-position benzene ring of B, both the fluorescence peak and the half-peak width of the material are not significantly changed, and finally, the turn-on voltage of the device is significantly reduced in the device, the lifetime and efficiency of the device are improved, and the efficiency roll-off of the device under high current density is reduced.
As can be seen from table 2 and fig. 2, compared with BD1, in the boron-containing compounds 2-6 and 2-1 of the present invention, the low triplet perylene group is introduced to the benzene ring at the B para position, and both the fluorescence peak and the half-peak width of the material are not significantly changed, so that the turn-on voltage of the device is significantly reduced in the device, the lifetime and the efficiency of the device are improved, and the efficiency roll-off of the device under a large current density is reduced.
As can be seen from table 3, compared with BD1, the boron-containing compounds 2-7 of the present invention have significantly improved device performance and significantly reduced turn-on voltage by introducing a bulky steric group. Meanwhile, the device efficiency is not obviously changed under the conditions of different doping concentrations, compared with the device efficiency of the comparative example material BD1, which is quenched more seriously along with the increase of the doping concentration.
According to the invention, through introducing groups such as anthracene and pyrene on the boron para-position aromatic ring, the generation of long-life triplet excitons is avoided, and meanwhile, the fluorescence peak of the material is not subjected to obvious blue shift or red shift, so that the device performance of the material is further improved in an OLED device. In addition, the preparation method of the polycyclic boron-containing compound is simple, raw materials are easy to obtain, no isomer is generated, the purification process is simple, and the industrialized development requirement can be met.
The above-mentioned embodiments are intended to illustrate the objects, technical solutions and advantages of the present invention in further detail, and it should be understood that the above-mentioned embodiments are only exemplary embodiments of the present invention and are not intended to limit the present invention, and any modifications, equivalents, improvements and the like made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A boron-containing organic compound comprising a compound represented by any one of formulae (I) to (III):
R1～R14are respectively selected from any one of the following groups: hydrogen atom, deuterium atom, halogen, cyano group, NO2、N(R)2、OR、SR、C(＝O)R、P(＝O)R、Si(R)3Get, getSubstituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl, wherein R is selected from any one of the following groups: a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C5-C30 heteroaryl group;
m is substituted or unsubstituted aryl of C6-C48;
X1、X2are respectively selected from any one of the following groups: o, S, N-Y, C (Y)2Wherein Y is selected from any one of the following groups: substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C40 aryl or substituted or unsubstituted C5-C40 heteroaryl.
2. The compound of claim 1, wherein M is selected from any one of the following groups:
wherein A is1～A6，B1～B9，C1～C8，D1～D9，E1～E6，F1～F7，G1～G10，H1～H9，K1～K12，L1～L6，M1～M12，N1～N10，O1～O17，P1～P15，Q1～Q15，I1～I15,R1～R15，S1～S13，T1～T13，U1～U12，V1～V12，W1～W17，X1～X15，Y1～Y15，Z1～Z15，J1～J15，Aa1～Aa15，Bb1～Bb15，Cc1～Cc16，Dd1～Dd15，Ee1～Ee15，Ff1～Ff15，Gg1～Gg15，Hh1～Hh17，Ii1～Ii15，Jj1～Jj15Are respectively selected from any one of the following groups: a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C5-C30 heteroaryl group.
3. The compound of claim 1, wherein the C1-C20 alkyl is selected from any one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, 2-methylhexyl, n-octyl, isooctyl, tert-octyl, 2-ethylhexyl, 3-methylheptyl, n-nonyl, n-decyl, hexadecyl, octadecyl, eicosyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl.
4. The compound of claim 1, wherein the alkenyl group having 2-20 is selected from any one of the following groups: vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, 2-ethylhexenyl, allyl, or cyclohexenyl.
5. The compound of claim 1, wherein the alkynyl group having 2-20 is selected from any one of the following groups: ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl.
6. The compound of claim 1, wherein the aryl group having 6-40 is selected from any one of the following groups: phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, perylenyl, anthryl, benzofluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, pentabiphenyl, terphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, cis-or trans-monobenzindenofluorenyl, cis-or trans-dibenzoindenofluorenyl, trimeric indenyl, isotridecylindenyl, spirotrimeric indenyl, spiroisotridecylindenyl.
7. The compound of claim 1, wherein the heteroaryl of C5-C40 is selected from any one of the following groups: furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl, indolocarbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthraoxazolyl, phenanthrooxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, thiazoyl, phenanthroimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthoxazolyl, and a naphthoxazolyl, Benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazanthryl, 2, 7-diazylpyryl, 2, 3-diazylpyryl, 1, 6-diazylpyryl, 1, 8-diazylpyryl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenoxazinyl, phenothiazinyl, fluoresceinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,3, 4-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl and the like, preferably phenyl, naphthyl, anthryl, phenanthryl, benzanthryl, benzophenanthryl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, indolyl, isoindolyl, carbazolyl.
8. The compound of claim 1, wherein the substituents of the substituted aryl group having 6-40 and the substituted heteroaryl group having 5-40 are selected from any one of the following groups: deuterium atom, halogen, amino group, hydroxyl group, cyano group, C1-C6 alkyl group.
9. The compound of claim 1, wherein the boron-containing organic compound is selected from any one of:
10. a light-emitting device comprising a first electrode, a second electrode and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer contains at least one compound according to any one of claims 1 to 9.
Priority Applications (2)
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| CN114560879A (en) * | 2022-03-02 | 2022-05-31 | 武汉华星光电半导体显示技术有限公司 | Fluorescent compound, mixture and light-emitting device |
| CN116023402A (en) * | 2023-02-17 | 2023-04-28 | 季华实验室 | Boron-nitrogen compound and preparation method and application thereof |
| WO2023142486A1 (en) * | 2022-01-28 | 2023-08-03 | 季华恒烨(佛山)电子材料有限公司 | Boron-nitrogen compound, preparation method therefor, and application thereof |
| WO2023142485A1 (en) * | 2022-01-28 | 2023-08-03 | 季华恒烨(佛山)电子材料有限公司 | Boron-nitrogen compound, preparation method therefor, and application thereof |
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| CN110407859A (en) * | 2019-07-18 | 2019-11-05 | 清华大学 | A kind of luminescent material and its organic electroluminescence device using and comprising it |
| CN110719914A (en) * | 2017-07-07 | 2020-01-21 | 学校法人关西学院 | Polycyclic aromatic compound |
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| CN110407859A (en) * | 2019-07-18 | 2019-11-05 | 清华大学 | A kind of luminescent material and its organic electroluminescence device using and comprising it |
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| WO2023142486A1 (en) * | 2022-01-28 | 2023-08-03 | 季华恒烨(佛山)电子材料有限公司 | Boron-nitrogen compound, preparation method therefor, and application thereof |
| WO2023142485A1 (en) * | 2022-01-28 | 2023-08-03 | 季华恒烨(佛山)电子材料有限公司 | Boron-nitrogen compound, preparation method therefor, and application thereof |
| CN114560879A (en) * | 2022-03-02 | 2022-05-31 | 武汉华星光电半导体显示技术有限公司 | Fluorescent compound, mixture and light-emitting device |
| CN114560879B (en) * | 2022-03-02 | 2023-11-28 | 武汉华星光电半导体显示技术有限公司 | Fluorescent compound, mixture and light-emitting device |
| CN116023402A (en) * | 2023-02-17 | 2023-04-28 | 季华实验室 | Boron-nitrogen compound and preparation method and application thereof |
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