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CN-121991105-A - Boron nitride compound and application thereof

CN121991105ACN 121991105 ACN121991105 ACN 121991105ACN-121991105-A

Abstract

The invention provides a boron nitrogen compound and application thereof, wherein the boron nitrogen compound has a structure shown in a formula I and a formula II, and the boron nitrogen compound is based on a compound formed by optimizing a carbazole derivative-boron nitrogen compound structure. The boron nitride compound has narrow spectrum luminescence characteristic, is used as a narrow spectrum luminescent material for preparing a luminescent layer of an organic electroluminescent device, and the prepared organic electroluminescent device realizes narrow spectrum TADF emission, has half-peak width smaller than 45nm, and ensures that the electroluminescent highest external quantum efficiency of the device is more than 30 percent.

Inventors

  • WANG YUE

Assignees

  • 吉林大学

Dates

Publication Date
20260508
Application Date
20241105

Claims (10)

  1. 1. A boron nitride compound, characterized in that the boron nitride compound has a structure represented by formula I or formula II: R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 and R 9 are independently selected from H, deuterium, C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C18 aryl substituted with one or more R a , 5-to 18-membered heteroaryl substituted with one or more R a , diphenylamino, or diphenylamino substituted with one or more R a ; R 10 is selected from C1-C20 alkyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C18 aryl substituted with one or more R a , 5-to 18-membered heteroaryl substituted with one or more R a , diphenylamino, or diphenylamino substituted with one or more R a ; R a is independently at each occurrence deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C14 aryl substituted with one or more R b , 5-to 18-membered heteroaryl substituted with one or more R b , diphenylamino, or diphenylamino substituted with one or more R b ; R b is independently at each occurrence deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl substituted with one or more R c , 5-to 18-membered heteroaryl substituted with one or more R c , diphenylamino, or diphenylamino substituted with one or more R c ; R c is independently at each occurrence deuterium, fluorine, CN, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl substituted with one or more R d , 5-to 18-membered heteroaryl substituted with one or more R d , diphenylamino, or diphenylamino substituted with one or more R d ; R d is independently at each occurrence deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, C6-C14 aryl or C6-C14 aryl substituted by one or more R e ; R e is independently at each occurrence deuterium, fluorine, C1-C12 alkyl, C1-C12 alkoxy, C3-C10 cycloalkyl, or C6-C14 aryl; R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 and R 9 R 10 are independently present or at least one of R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 forms a ring with the attached aromatic ring; R 11 、R 12 and R 13 are H, D (deuterium), C1-C18 alkyl, C6-C18 aryl substituted with one or more R a , 5-to 24-membered heteroaryl or 5-to 18-membered heteroaryl substituted with one or more R a ; The alkyl, alkoxy, cycloalkyl, aryl, heteroaryl groups are optionally substituted with one or more substituents selected from the group consisting of halogen, -CN, C1-C12 alkyl, C1-C12 alkoxy, C1-C12 haloalkyl, C3-C10 cycloalkyl, C6-C14 aryl, and 5-to 18-membered heteroaryl.
  2. 2. The boron nitride compound according to claim 1, wherein R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 and R 9 are independently H, deuterium, C1-C12 alkyl, C 1 ～C 12 alkoxy, C 3 -C 10 cycloalkyl, phenyl-C 1 ～C 12 alkyl, diphenylamino substituted by at least one C 1 -C 12 alkyl, carbazolyl substituted by at least one C 1 -C 12 alkyl; R 10 is C1-C12 alkyl, C 1 ～C 12 alkoxy, C 3 -C 10 cycloalkyl, phenyl-C 1 ～C 12 alkyl, diphenylamino substituted by at least one C 1 -C 12 alkyl, carbazolyl substituted by at least one C 1 -C 12 alkyl; Preferably, each occurrence of said R a is independently deuterium, fluoro, C 1 ～C 12 alkyl, C 1 ～C 12 alkoxy, C 3 -C 10 cycloalkyl, phenyl substituted with at least one C 1 -C 12 alkyl, phenyl substituted with at least one C 1 -C 12 alkoxy, phenyl-C 1 ～C 12 alkyl, diphenylamino substituted with at least one C 1 -C 12 alkyl, carbazolyl substituted with at least one C 1 -C 12 alkyl; Preferably, each occurrence of said R b is independently deuterium, fluoro, C 1 ～C 12 alkyl, C 1 ～C 12 alkoxy, C 3 -C 10 cycloalkyl, phenyl substituted with at least one C 1 -C 12 alkyl, phenyl substituted with at least one C 1 -C 12 alkoxy, phenyl-C 1 ～C 12 alkyl, diphenylamino substituted with at least one C 1 -C 12 alkyl, carbazolyl substituted with at least one C 1 -C 12 alkyl; Preferably, each occurrence of said R c is independently deuterium, fluoro, C 1 ～C 12 alkyl, C 1 ～C 12 alkoxy, C 3 -C 10 cycloalkyl, phenyl substituted with at least one C 1 -C 12 alkyl, phenyl substituted with at least one C 1 -C 12 alkoxy, phenyl-C 1 ～C 12 alkyl, diphenylamino substituted with at least one C 1 -C 12 alkyl, carbazolyl substituted with at least one C 1 -C 12 alkyl; Preferably, each occurrence of said R d is independently deuterium, fluoro, C 1 ～C 12 alkyl, C 1 ～C 12 alkoxy, C 3 -C 10 cycloalkyl, phenyl substituted with at least one C 1 -C 12 alkyl, phenyl substituted with at least one C 1 -C 12 alkoxy, carbazolyl substituted with at least one C 1 -C 12 alkyl; Preferably, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 are independently methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, hexyl, octyl, decyl, Methoxy, ethoxy, butoxy, hexyloxy, Cyclohexyl, adamantyl, phenyl, 2-methyl-phenyl, 4-ethyl-phenyl, 4-propyl-phenyl, 4-isopropylphenyl, 4-n-butylphenyl, Wherein the wavy line represents the attachment site of the group; preferably, the R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 are independently methyl, 2-methyl-phenyl, Phenyl group, Wherein the wavy line represents the attachment site of the group; Preferably, the R 11 、R 12 and R 13 are selected from H, deuterium, C6-C18 aryl or 5-to 24-membered heteroaryl; preferably, the R 11 、R 12 and R 13 are selected from H, phenyl, biphenyl, Preferably, at least one of R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and R 10 is in the following ring structure with the attached aromatic ring: wherein the bond is a bond shared with the aromatic ring.
  3. 3. The boron nitride compound according to claim 1 or 2, wherein the boron nitride compound is any one of the following compounds:
  4. 4. An organic electroluminescent composition, characterized in that it comprises the boron nitride compound according to any one of claims 1 to 3 and a host material as doping materials; Preferably, the host material is a material having an electron transport ability and/or a hole transport ability and having a triplet excited state energy higher than or equal to that of the doped light emitting material.
  5. 5. The organic electroluminescent composition according to claim 4, wherein the host material is a compound having a structure represented by any one of formulae (H-1) to (H-10): Wherein X 1 、Y 1 and Z 1 are CH or N and at most one of X 1 、Y 1 and Z 1 is N; Wherein R 1H and R 2H are independently any of the following groups: Wherein X 2 、Y 2 and Z 2 are CH or N and at most one of X 2 、Y 2 and Z 2 is N; Wherein R aH and R bH are independently H, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 6 -C 20 aryl, C 1 -C 20 alkyl substituted C 6 -C 20 aryl or C 1 -C 20 alkoxy substituted C 6 -C 20 aryl, the numbers represent the attachment site of the group; W 1 、W 2 、W 3 、W 4 、W 5 、W 6 、W 7 、W 8 and W 9 are independently S or O; R 3H 、R 4H 、R 5H 、R 6H 、R 7H 、R 8H 、R 9H 、R 10H 、R 11H 、R 12H 、R 13H And R 14H is independently H, deuterium, C1-C6 alkyl or C6-C24 aryl; Preferably, the organic electroluminescent composition comprises 0.3 to 30.0wt% of the boron-nitrogen compound according to any one of claims 1 to 3 as a doping material, and the remaining 99.7 to 70.0wt% of the host material composed of 1 to 2 compounds having the structures of formulae (H-1) to (H-10); Preferably, the host material contains 2 compounds having the structures of formula (H-1) to formula (H-10) in a weight ratio of 1:5 to 5:1; Preferably, the host material in the organic electroluminescent composition is one or two of the compounds H1-1 to H1-254; Preferably, the organic electroluminescent composition comprises 0.3-30.0wt% of the boron-nitrogen compound according to any one of claims 1-3, and the rest 99.7-70.0wt% is 1 or 2 of the compounds H1-1 to H1-254; preferably, the organic electroluminescent composition contains 2 compounds H1-1 to H1-254 as main materials, and the weight ratio of the two compounds is 1:5 to 5:1; Preferably, the doping material in the organic electroluminescent composition is any one of the boron-nitrogen compounds in any one of claims 1-3, and the host material is composed of any one of compounds shown as formulas Trz1-A, trz2-A, trz3-A, trz4-A, trz5-A or Trz6-A and any one of compounds with structures shown as formulas H-1 to H-10; Wherein 1 or 2 of R 1a 、R 1b 、R 2a 、R 2b 、R 3a and R 3b are independently R Tz , the remainder are the same or different and are independently hydrogen, deuterium, C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 6 -C 18 aryl, C 1 -C 8 alkyl substituted C 6 -C 18 aryl or C 1 -C 8 alkoxy substituted C 6 -C 18 aryl, R Tz is any one of the substituents shown in the following formula: Wherein asterisks represent the attachment site of the group; Preferably, the amount ratio of Trz1-A, trz2-A, trz3-A, trz4-A, trz-A or Trz6-A to H-1, H-2, H-3, H-4, H-5H-6, H-7, H-8, H9 or H-10 is 1:20 to 20:1; Preferably, the weight ratio between the compound shown in the formulas TRZ-1 to TRZ-86 and the carbazole or carboline derivative with the structure shown in any one of the formulas (H-1) to (H-10) in the main body material is 1:20 to 20:1; Preferably, the weight ratio between the compound represented by the formulas TRZ-1 to TRZ-86 and the compound of H1-1 to H1-254 in the host material is 1:20 to 20:1; preferably, the doping material in the organic electroluminescent composition is the boron nitrogen compound as claimed in any one of claims 1 to 3, the host material is composed of any one of the compounds of the formulas Trz1-A, trz2-A, trz3-A, trz4-A, trz-A or Trz6-A and any one of the compounds of the formulas H-1 to H-10, and the weight ratio of the Trz1-A, trz2-A, trz3-A, trz4-A, trz5-A or Trz6-A compound to the compounds of the formulas H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H-9 or H-10 is 1:20 to 20:1; preferably, the doping material in the organic electroluminescent composition is the boron nitrogen compound as defined in any one of claims 1-3, the host material is composed of any one of 1,3, 5-triazine derivatives shown in formulas TRZ-1 to TRZ-86 and any one of carbazole or carboline derivatives shown in formulas H1-1 to H1-254, and the weight ratio of the 1,3, 5-triazine derivatives to the carbazole or carboline derivatives in the host material is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is any one compound shown in formulas BN-1 to BN-148, the host material is composed of any one compound shown in formulas Trz1-A, trz-A, trz3-A, trz4-A, trz-A and Trz6-A and any one carbazole or carboline derivative shown in formulas H1-1 to H1-254, and the weight ratio of the compound shown in formulas Trz1-A, trz2-A, trz3-A, trz4-A, trz5-A and Trz6-A to the carbazole or carboline derivative shown in formulas H1-1 to H1-254 is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is any one compound shown in the formulas BN-1 to BN-148, the host material consists of any one of 1,3, 5-triazine derivatives shown in the formulas TRZ-1 to TRZ-86 and any one of carbazole or carboline derivatives shown in the formulas H1-1 to H1-254, and the weight ratio of the 1,3, 5-triazine derivatives shown in the formulas TRZ-1 to TRZ-86 to the carbazole or carboline derivatives shown in the formulas H1-1 to H1-254 is 1:20 to 20:1; Preferably, in the organic electroluminescent composition, the host material is composed of any one of compounds having structures represented by formulas H-1 to H-10 and any one of compounds represented by formulas Ph-2CN-1, ph-2CN-2, ph-2CN-3, ph-2CN-4, ph-2CN-5 or Ph-2 CN-6; Y 1 、Y 2 、Y 3 、Y 4 、Y 5 、Y 6 、Y 7 and Y 8 are independently O (oxygen) or S (sulfur); R s1 、R s2 、R s3 、R s4 、R s5 and R s6 are independently C6-C24 aryl or C12-C36 heteroaryl; R si (i=7-39) is independently H, deuterium, C1-C6 alkyl, C1-C6 alkoxy or C6-C24 aryl; preferably, R s1 、R s2 、R s3 、R s4 、R s5 and R s6 are independently selected from any of the following 24 groups: asterisks indicate the attachment site of the group; preferably, rs i (i=7-39) is independently selected from any of the following 5 groups: ＊ H＊-D * -CH3 asterisks indicate the attachment site of the group; Preferably, the doping material in the organic electroluminescent composition is any one of the boron nitride compounds as described in any one of claims 1 to 3, and the host material is a structure composed of any one of the compounds represented by formulas 2CN-1 to 2CN-60 and any one of the compounds represented by formulas H1-1 to H1-254; Preferably, the doping material in the organic electroluminescent composition is the boron-nitrogen compound as claimed in any one of claims 1 to 3, the host material is composed of any one of compounds shown as formula Ph-2CN-1, ph-2CN-2, ph-2CN-3, ph-2CN-4, ph-2CN-5 or Ph-2CN-6 and any one of compounds shown as formulas H-1 to H-10, and preferably, the weight ratio of the Ph-2CN-1, ph-2CN-2, ph-2CN-3, ph-2CN-4, ph-2CN-5 or Ph-2CN-6 to the compounds shown as H-1, H-2, H-3, H-4, H-5, H-6, H-7, H-8, H-9 or H-10 is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is the boron nitride compound as defined in any one of claims 1-3, the host material is composed of any one of dicyanobenzene derivatives as shown in formulas 2CN-1 to 2CN-60 and any one of carbazole derivatives as shown in formulas H1-1 to H1-254, and preferably, the weight ratio of dicyanobenzene derivatives to carbazole derivatives in the host material is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is any one compound shown in the formulas BN-1 to BN-148, the host material is composed of any one compound shown in the formulas Ph-2CN-1, ph-2CN-2, ph-2CN-3, ph-2CN-4, ph-2CN-5 or Ph-2CN-6 and any one compound shown in the formulas H1-1 to H1-254, and preferably, the weight ratio of the compounds shown in the formulas Ph-2CN-1, ph-2CN-2, ph-2CN-3, ph-2CN-4, ph-2CN-5 or Ph-2CN-6 to the compounds shown in the formulas H1-1 to H1-254 in the host material is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is any one compound shown in formulas BN-1 to BN-148, the host material is composed of any one dicyanobenzene derivative shown in formulas 2CN-1 to 2CN-60 and any one compound shown in formulas H1-1 to H1-254, and preferably, the weight ratio of the dicyanobenzene derivative shown in formulas 2CN-1 to 2CN-60 to the carbazole derivative shown in formulas H1-1 to H1-254 in the host material is 1:20 to 20:1; Preferably, the doping material in the organic electroluminescent composition is the boron-nitrogen compound as defined in any one of claims 1-3, the host material is composed of any one of compounds shown in formulas H1-1 to H1-254 and phosphorescent compounds containing metal Ir or Pt shown in formulas Ir-1, ir-2 and Pt-1, and preferably, the weight ratio of the compounds shown in formulas H1-1 to H1-254 to the phosphorescent compounds containing metal Ir or Pt in the host material is 1:20 to 20:1; R ri is independently hydrogen, deuterium, C1-C18 alkyl or C6-C18 aryl, wherein i is an integer from 1 to 22, wherein the dashed line represents two bonds spaced apart from each other of the four bonds comprised are double bonds; Any one of the R ri groups may form a ring with the aromatic or heteroaromatic ring to which it is attached; Preferably, the phosphorescent compound containing metallic Ir or Pt is any one of the following compounds: Preferably, the organic electroluminescent composition is a luminescent layer, the doping material in the organic electroluminescent composition is any one compound shown in formulas BN-1 to BN-148, the host material is composed of any one of carbazole or carboline derivatives shown in formulas H1-1 to H1-254 and phosphorescent compounds containing metal Ir shown in formulas Ir-1 and Ir-2, and preferably, the weight ratio of the carbazole or carboline derivatives shown in formulas H1-1 to H1-254 to the phosphorescent compounds containing metal Ir in the host material is 1:20 to 20:1.
  6. 6. An organic electroluminescent material, characterized in that it comprises the boron-nitrogen compound according to any one of claims 1 to 3 or the organic electroluminescent composition according to claim 4 or 5.
  7. 7. An organic electroluminescent device comprising an anode and a cathode and an organic thin film layer interposed between the anode and the cathode, the organic thin film layer comprising the boron-nitrogen compound of any one of claims 1 to 3 or the organic electroluminescent composition of claim 4 or 5.
  8. 8. The organic electroluminescent device according to claim 7, wherein the organic thin film layer comprises a light emitting layer, an optional hole injection layer, an optional hole transport layer, an optional electron injection layer, wherein at least one of the light emitting layer, the electron injection layer, the electron transport layer, the hole injection layer comprises the boron nitrogen compound of any one of claims 1 to 3 or the organic electroluminescent composition of claim 4 or 5.
  9. 9. The organic electroluminescent device according to claim 7 or 8, wherein a material of a light-emitting layer in the organic electroluminescent device comprises the boron-nitrogen compound according to any one of claims 1 to 3 or the organic electroluminescent composition according to claim 4 or 5; Preferably, the organic electroluminescent device further comprises an optional hole blocking layer, an optional electron blocking layer and an optional capping layer.
  10. 10. Use of an organic electroluminescent device according to any of claims 7-9 in an organic electroluminescent display or an organic electroluminescent illumination source.

Description

Boron nitride compound and application thereof Technical Field The invention belongs to the technical field of organic electroluminescence, and relates to a boron-nitrogen compound and application thereof. Background The organic photoelectric material (Organic Optoelectronic Materials) is an organic material with the characteristics of photon and electron generation, conversion and transmission. Currently, controllable photoelectric properties of Organic photoelectric materials have been applied to Organic Light-Emitting diodes (OLEDs), organic solar cells (Organic Photovoltage, OPV), organic FIELD EFFECT Transistors (OFETs), and even Organic lasers. In recent years, OLEDs have become a very popular new flat display product at home and abroad. The OLED display has the characteristics of self-luminescence, wide viewing angle, short reaction time, high luminous efficiency, wide color gamut, low working voltage, thin panel, capability of manufacturing a large-size flexible panel and low cost, and is known as a star flat display product in the 21 st century. In relation to the history of organic electroluminescence, it was traced back to report (Holst G A,Kster T,Voges E,et al.FLOX—an oxygen-flux-measuring system using a phase-modulation method to evaluate the oxygen-dependent fluorescence lifetime,ScienceDirect.Sensors and Actuators B:Chemical,1995,29,213.), of Bernanose et al in 1953, that in 1963, pope et al at new york university applied a voltage to anthracene crystals, and it was observed that anthracene fluorescence emission was (M.Pope,H.Kallmann and P.Magnante,Electroluminescence in Organic Crystals,J.Chem.Phys.,1963,38,2042).1987, c.w. tang et al of Kodak corporation in usa used an ultrathin film technique with aromatic amine having a good hole transporting effect as a hole transporting layer, an aluminum complex of 8-hydroxyquinoline as a light emitting layer, and Indium Tin Oxide (ITO) thin film and a metal alloy as an anode and a cathode, respectively, to prepare a light emitting device. The device obtains green light emission with the brightness as high as 1000cd/m 2 under the driving voltage of 10V, the efficiency of the device is 1.5lm/W (C.W.Tang and S.A.VanSlyke, organic electroluminescent diodes, appl.Phys.Lett.,1987,51,913), and the breakthrough progress enables the organic electroluminescence research to be rapidly and deeply developed worldwide. In 1990, burroughes et al, university of Cambridge, proposed the first polymer (PPV) -based light emitting diode. The PPV is shown to be an emitting material with high fluorescence in a single-layer device, and has higher luminous efficiency of (Burroughes J.H.et al.,Light-emitting diodes based on conjugated polymers,Nature,1990,347,539.).1998 years, baldo and Forrest of Pranceton university report a first phosphorescence device based on electroluminescence, which can in principle have an internal quantum yield of (M.A.Baldo,D.F.O'Brienetal.,Highly efficient phosphorescent emission from organic electroluminescent devices,Nature,1998,395,151), of 100%, but on the one hand, the phosphorescence material generally uses noble metals such as iridium platinum and the like, and is expensive, on the other hand, the dark blue phosphorescence material still has chemical instability, and the device has the problems of larger efficiency roll-off and the like under high current density, so that the development of an OLED device which uses cheap and stable organic small molecular materials and can realize high-efficiency luminescence is very important. In 2012, the Adachi research group at the university of ninety reports that the efficient fully fluorescent OLED device (Uoyama H,Goushi K,Shizu K,et al.Highly efficient organic light-emitting diodes from delayed fluorescence,Nature,2012,492(7428):234-238.), based on the Thermally Activated Delayed Fluorescence (TADF) mechanism can absorb thermal energy when the S1 and T1 energy levels of the molecules are sufficiently small, and the triplet excitons return to the singlet state through the RISC process, thereby emitting fluorescence, and the Internal Quantum Efficiency (IQE) of the device can theoretically reach 100%, and the External Quantum Efficiency (EQE) can even reach 30%, as compared to the level of the shoulder phosphorescence device. As a next-generation light-emitting material, a TADF material is being studied. TADF molecules are mainly used as guest materials to be doped in a wide-bandgap host material to realize high-efficiency heat-activated delayed fluorescence (Q.Zhang,J.Li,K.Shizu,et al.Design of Efficient Thermally Activated Delayed Fluorescence Materials for Pure Blue Organic Light Emitting Diodes,J.Am.Chem.Soc.2012,134,14706;H.Uoyama,K.Goushi,K.Shizu,H.Nomura,C.Adachi,Highly efficient organic light-emitting diodes from delayed fluorescence,Nature,2012,492,234;T.Nishimoto,T.Yasuda,et al.,A six-carbazole-decorated cyclophosphazene as a host with high triplet energy to realize efficient delayed-fluo