WO2022121920A1 - Composé bore-azote, composition électroluminescente organique et dispositif électroluminescent organique le contenant - Google Patents

Composé bore-azote, composition électroluminescente organique et dispositif électroluminescent organique le contenant Download PDF

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WO2022121920A1
WO2022121920A1 PCT/CN2021/136306 CN2021136306W WO2022121920A1 WO 2022121920 A1 WO2022121920 A1 WO 2022121920A1 CN 2021136306 W CN2021136306 W CN 2021136306W WO 2022121920 A1 WO2022121920 A1 WO 2022121920A1
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aryl
boron
alkoxy
alkyl
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王悦
梁宝炎
毕海
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季华实验室
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Definitions

  • the embodiments of the present disclosure relate to the technical field of organic electroluminescence, such as a boron-nitrogen compound and a method for synthesizing the same, an organic electroluminescence composition, and an organic electroluminescence device comprising the aforementioned compound or composition.
  • Organic electroluminescence technology has shown great application prospects in the fields of full-color display and solid-state white light illumination, and has received extensive research and attention in the scientific research and industrial circles.
  • Organic small-molecule optoelectronic materials have been widely used as high-performance electroluminescent materials due to their clear structure, easy modification, and simple purification and processing.
  • traditional fluorescent dye molecules often have high photoluminescence quantum yields, but electroluminescence devices based on these fluorescent materials are limited by the internal quantum efficiency of 25%, and the external quantum efficiency of electroluminescence devices is generally lower than 5%, there is still a big gap with the efficiency of phosphorescent devices.
  • Delayed fluorescence mechanisms mainly include two types: (1) TTA (Triplet-Triplet Annihilation, triplet-triplet annihilation) mechanism; (2) TADF (Thermally Activated Delayed Fluorescence, thermally activated delayed fluorescence) mechanism.
  • TTA Triplet-Triplet Annihilation, triplet-triplet annihilation
  • TADF Thermally Activated Delayed Fluorescence, thermally activated delayed fluorescence
  • the TTA mechanism is a mechanism that utilizes the fusion of two triplet excitons to generate singlet excitons and improves the generation rate of singlet excitons, but the maximum internal quantum efficiency of the device is only 40% to 62.5%.
  • the TADF mechanism utilizes small organic molecules with a small singlet-triplet energy level difference ( ⁇ E ST ), and its triplet excitons can be transformed into a reverse intersystem crossing (RISC) process under ambient thermal energy.
  • RISC reverse intersystem crossing
  • the mechanism of singlet excitons can reach 100%.
  • its device has a large efficiency roll-off at high brightness, which limits its application in full-color display and white lighting.
  • TADF molecules are mainly doped as guest materials in wide-bandgap host materials to achieve high-efficiency thermally activated delayed fluorescence (see J.Am.Chem.Soc.2012,134,14706;Nature,2012,492,234;Mater.Horiz., 2014, 1, 264).
  • TADF emission mainly originates from the transition of intramolecular charge transfer (ICT: intramolecular charge transfer) state. Since most TADF light-emitting molecular structures adopt the form of conjugation or non-conjugation between electron donor (D:donor) groups and electron acceptor (A;acceptor) groups, the so-called D-A structure (Structure 1) , its electron donor group and electron acceptor group are separated in space, and this type of molecule is defined as: separated D-A structure.
  • ICT intramolecular charge transfer
  • This D-A structure is conducive to the spatial separation of the highest occupied molecular orbital (HOMO: the highest occupied molecular orbital) and the lowest unoccupied molecular orbital (LUMO: the lowest unoccupied molecular orbital), and thus easy to obtain TADF luminescence. Moreover, based on the D-A structure, it is easy to realize the regulation of the peak position (wavelength) of the emission spectrum, that is, the emission color. However, the D-A structure shown in structure 1 can easily lead to configuration and conformation changes when the molecule is in the ground state and excited state, and generate abundant molecular vibrational modes. The emission spectra of most of these luminescent molecules are more than 100 nm wide at half maximum. Although a wider spectrum is beneficial for lighting applications, it cannot meet the requirements of high color purity in the display field. The main purpose of OLED light emission is display, so the narrow spectral design of TADF material (ie, smaller half-peak width) is very necessary.
  • the chromophore core structure, and the three benzene rings that coordinate with B are covalently connected to N.
  • Such molecules are called B-N complexes (structure 2), that is, the compounds are formed by the coordination of aromatic amine organic molecules with B. luminescent compounds.
  • the frontier molecular orbitals of such tricoordinate B complexes have a characteristic, that is, the highest occupied orbital (HOMO: the highest occupied molecular orbital) and the lowest unoccupied orbital (LUMO: the lowest unoccupied molecular orbital) are alternately occupied (the so-called so-called The resonance structure of ) is distributed in the coordination system, with B in the LUMO orbital and N in the HOMO orbital.
  • This type of B-N complexes have excited state charge transfer and TADF luminescence properties due to their unique HOMO and LUMO alternating electronic structure (resonance structure) (this type of molecule is defined as: resonance type D-A molecule), and it is very important.
  • the present disclosure provides an organic compound, a composition and the same that emit light in the green light to red light region and have narrow-spectrum TADF emission characteristics.
  • the present disclosure provides a boron-nitrogen compound having the structure shown in formula I or II,
  • Each occurrence of R 1 is independently H, D (deuterium), fluorine, CN, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 3 -C 10 cycloalkyl, C 6 -C 14 aryl, C 6 -C 14 aryl substituted by one or more Ra , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more Ra , Diphenylamino, or diphenylamino substituted with one or more Ra ;
  • E is a single key
  • R 11 and R 22 are independently H, D (deuterium), C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
  • R is:
  • R 4 , R 5 and R 6 is independently H, D (deuterium), fluorine, CN, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 3 -C 10 cycloalkane aryl, C 6 -C 14 aryl, C 6 -C 14 aryl substituted by one or more R d , 5- to 18-membered heteroaryl, or 5- to 18 substituted by one or more R d -membered heteroaryl;
  • Each occurrence of R a is independently D (deuterium), fluorine, CN, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 3 -C 10 cycloalkyl, C 6 -C 14 aryl group, C 6 -C 14 aryl substituted by one or more R b , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R b , diphenylamine group, or diphenylamino group substituted by one or more R b ;
  • Each occurrence of R b is independently D (deuterium), fluorine, CN, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 3 -C 10 cycloalkyl, C 6 -C 14 aryl base, C 6 -C 14 aryl substituted by one or more R c , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R c , diphenylamine group, or diphenylamino group substituted by one or more R c ;
  • R c is independently D (deuterium), fluorine, CN, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 3 -C 10 cycloalkyl, C 6 -C 14 aryl group, C 6 -C 14 aryl substituted by one or more R d , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R d , diphenylamine group, or diphenylamino group substituted by one or more R d ;
  • R d is independently D (deuterium), fluorine, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 3 -C 10 cycloalkyl, C 6 -C 14 aryl, or C 6 -C 14 aryl substituted by one or more R e ;
  • R e is independently D (deuterium), fluorine, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 3 -C 10 cycloalkyl, or C 6 -C 14 aryl ;
  • alkyl groups, alkoxy groups, cycloalkyl groups, aryl groups, and heteroaryl groups are optionally substituted by one or more substituents selected from the group consisting of halogen, -CN, C 1 -C 12 alkyl, C 1 - C 12 alkoxy, C 1 -C 12 haloalkyl, C 2 -C 6 alkenyl, C 3 -C 10 cycloalkyl, C 6 -C 14 aryl, or 5- to 18-membered heteroaryl.
  • the present disclosure provides a method for preparing the above-mentioned boron-nitrogen compound, which comprises the steps shown in the following reaction formulas (1) and (2):
  • the carbazole skeleton-containing boron nitrogen core compound is used as the reactant, which is dissolved in an organic solvent, heated to reflux in the presence of a catalyst, and the para-hydrogen atom of the boron atom of the b benzene ring is activated. and replaced by boron ester;
  • the electron-withdrawing group is introduced into the boron-nitrogen skeleton by using the Suzuki reaction, and the introduced electron-withdrawing group is located in the para position of the B atom of the b benzene ring in the boron-nitrogen skeleton;
  • ArX is any one of the following three molecules:
  • X is Br or Cl
  • R 1 , R 4 , R 5 , R 6 , R 11 , R 22 , and R are as defined above.
  • the present disclosure provides an organic electroluminescent composition comprising the above-mentioned boron-nitrogen compound. Further, the present disclosure also provides an organic electroluminescence composition comprising the above-mentioned boron nitride compound and a host material.
  • the present disclosure provides an organic electroluminescent device comprising the above-mentioned boron nitride compound or organic electroluminescent composition.
  • Figure 1 is a schematic diagram of the device structure used in Effect Example 2, wherein 1 is an ITO anode, 2 is a hole injection layer, 3 is a hole transport layer, 4 is a light-emitting layer, 5 is an electron transport layer, and 6 is an electron injection layer layer, 7 is the metal cathode.
  • Figure 2 is the photoluminescence spectrum of the compound BN-66 doped film, wherein the composition of the doped film is H1-1 (97wt%):BN-66 (3wt%).
  • FIG. 4 is the temperature-resolved spectrum of the compound BN-66 doped film, wherein the composition of the doped film is H1-1 (97 wt %):BN-66 (3 wt %).
  • FIG. 5 is a graph showing the change of external quantum efficiency with luminance of the compound BN-66 doped device, wherein the doping weight percentage of the light-emitting layer is composed of H1-1 (97wt%):BN-66 (3wt%).
  • moiety refers to a specific fragment or functional group in a molecule.
  • a chemical moiety is usually thought of as a chemical entity embedded or attached to a molecule.
  • the present disclosure employs standard nomenclature and standard laboratory procedures and techniques of analytical chemistry, synthetic organic chemistry, and optics. In some cases, standard techniques are used for chemical synthesis, chemical analysis, and performance testing of light-emitting devices. Unless otherwise specified, the present disclosure adopts traditional methods of mass spectrometry and elemental analysis, and each step and condition may refer to the conventional operation steps and conditions in the art.
  • the compounds of the present disclosure may contain unnatural proportions of atomic isotopes at one or more of the atoms that constitute the compounds.
  • compounds can be labeled with isotopes, such as deuterium (D). All transformations of the isotopic composition of the compounds of the present disclosure, whether radioactive or not, are included within the scope of the present disclosure.
  • reagents and starting materials used in the present disclosure are commercially available or can be prepared by conventional chemical synthesis methods.
  • optionally fused to a ring means that it is fused to a ring or not to a ring.
  • optionally substituted refers to being unsubstituted or having at least one non-hydrogen substituent that does not destroy the luminescent properties possessed by the unsubstituted analog.
  • the number of “substitutions” can be one or more; when there are more than one, it can be 2, 3 or 4. In addition, when the number of the "substitution” is plural, the “substitution” may be the same or different.
  • substitution can be arbitrary unless otherwise specified.
  • the hydrogen or H is the hydrogen element in natural abundance, that is, a mixture of the isotopes protium, deuterium and tritium, wherein the abundance of protium is 99.98%.
  • the deuterium is D or 2 H, also called deuterium, and the abundance of deuterium at the deuterium substitution site is greater than 95%.
  • groups and their substituents can be selected by those skilled in the art to provide stable moieties and compounds.
  • substituents When substituents are described by conventional chemical formulae written from left to right, the substituents also include the chemically equivalent substituents obtained when the structural formula is written from right to left. For example -CH2O- is equivalent to -OCH2- .
  • halogen or halo as used herein refers to fluorine, chlorine, bromine or iodine. In one embodiment, the halogen or halo is preferably fluoro or fluoro.
  • alkyl as a group or part of other groups (eg, as used in halogen-substituted alkyl groups and the like) is meant to include branched and straight chain chains having the specified number of carbon atoms.
  • Saturated aliphatic hydrocarbon group For example, C 1 -C 20 alkyl includes straight-chain or branched-chain alkyl groups having 1 to 20 carbon atoms.
  • C1 - C6 alkyl is meant to include groups having 1, 2, 3, 4, 5, or 6 carbon atoms in a straight or branched chain structure.
  • the C 1 -C 6 alkyl groups are each independently methyl, ethyl, propyl, butyl, pentyl or hexyl; wherein, the propyl group is a C 3 alkyl group (including the same isomers such as n-propyl or isopropyl); butyl is C4 alkyl (including isomers such as n-butyl, sec-butyl, isobutyl or tert-butyl); pentyl is C5 alkyl (including isomers such as n-pentyl, 1-methyl-butyl, 1-ethyl-propyl, 2-methyl-1-butyl, 3-methyl-1- butyl, isopentyl, tert-amyl or neopentyl); hexyl is C6 alkyl (including isomers such as n-hexyl or isohexyl).
  • Substituted alkyl refers to an alkyl group substituted at any available point of attachment with one or more substituents, preferably 1 to 4 substituents.
  • haloalkyl refers to an alkyl group having one or more halogen substituents, eg, halomethyl including, but not limited to, eg -CH2Br, -CH2I , -CH2Cl , -CH2F , - Groups such as CHF 2 and -CF 3 .
  • alkoxy refers to an alkyl group, as defined above, attached via an oxygen bond (-O-), respectively.
  • substituted alkoxy refers to a substituted alkyl group, as defined above, attached via an oxygen bond.
  • Cn-m aryl as part of a group or other group refers to a monocyclic or polycyclic aromatic group having n to m ring carbon atoms (the ring atoms are only carbon atoms) having at least one carbocyclic ring with a conjugated pi electron system.
  • aryl unit examples include phenyl, biphenyl, naphthyl, indenyl, azulenyl, fluorenyl, phenanthryl, or anthracenyl.
  • the aryl group is preferably a C6-14 aryl group such as phenyl, biphenyl and naphthyl, more preferably phenyl.
  • n-m membered heteroaryl as part of a group or other group means that ring atoms contain one or more (eg 1, 2, 3 and 4) selected from nitrogen, oxygen and sulfur
  • the heteroatom of the aromatic group has n to m ring atoms, and the heteroaryl group is a monocyclic, bicyclic, tricyclic or tetracyclic ring system, wherein at least one ring is an aromatic ring.
  • Heteroaryl groups within the scope of this definition include, but are not limited to: acridinyl, carbazolyl, cinnolinyl, quinoxalinyl, pyrazolyl, indolyl, benzotriazolyl, furyl, thienyl , benzothienyl, benzofuranyl, quinolinyl, isoquinolinyl, oxazolyl, isoxazolyl, pyrazinyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, tetrahydroquinoline , imidazolyl, triazolyl, tetrazolyl, thiazolyl, isothiazolyl, furazanyl, thiadiazolyl, oxadiazolyl, triazinyl, purinyl, pteridyl, naphthyridinyl, quinazole Linoyl,
  • furyl, thienyl, pyrrolyl, imidazolyl, thiazolyl, pyrazolyl, oxazolyl, isoxazolyl can be listed , isothiazolyl, pyridyl, pyrimidinyl and carbazolyl, more preferably carbazolyl.
  • fused means that two or more carbocyclic or heterocyclic rings share a ring edge to form a polycyclic ring.
  • C n -C m cycloalkyl refers to a monocyclic or polycyclic alkyl group having n to m carbon atoms, such as C 3 -C 10 cycloalkyl and C 3 -C 6 cycloalkyl. Examples include adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and bicycloheptyl. In one embodiment, the C3 - C10 cycloalkyl is preferably adamantyl or cyclohexyl.
  • the present disclosure provides a method for designing and synthesizing organic light-emitting molecules with a luminescent peak between 495-630 nm and a narrow emission spectrum. 1) and HOMO and LUMO alternate layout electronic structure (resonance structure, as shown in structure 2) is different.
  • the specific molecular design adopted in the present disclosure is as follows:
  • Structure 3 Representative model molecular structure.
  • Structure 3 presents a representative molecular design model structure provided by the present disclosure.
  • the definition of the Ar group is as described above. It is a pyrimidine derivative with electron withdrawing ability.
  • the general method and principle of molecular design provided are: in HOMO and An additional pyrimidine derivative electron acceptor group is introduced into the functional skeleton of the LUMO alternate layout electronic structure (resonance structure), a C (carbon) atom of the introduced pyrimidine derivative and a C atom on the resonance structure group They are linked by a single bond, and the additional pyrimidine derivatives are covalently linked by para-substitution with respect to the B atom in the resonance structure (as shown in structure 3).
  • the LUMO orbital of the molecule provided by the present disclosure is formed by the LUMO orbital of the resonance structure part merged with the LUMO orbital of the additional pyrimidine derivative acceptor formed, and the HOMO orbital of the molecule provided by the present disclosure is the same as the HOMO orbital of the resonance structure part in the molecule. Therefore, the organic light-emitting molecule provided by the present disclosure is sterically separated from the molecular structure to the frontier orbital electronic structure and the existing electron donor group and electron acceptor group. D-A type structure and HOMO and LUMO alternate layout electronic structure (resonance structure) are different.
  • the advantage of the organic light-emitting molecule design method provided by the present disclosure is that it combines the advantages of the isolated D-A structure and the resonance D-A molecule, and overcomes the disadvantages of these two types of molecules. Since the additional pyrimidine derivative acceptor and B atom take a para-substituted form, and because the pyrimidine derivative acceptor has a strong electron-withdrawing ability, it will significantly improve the intramolecular charge transfer characteristics of the target molecule, and the strong intramolecular charge transfer characteristics It is beneficial to the realization of long-wavelength emission.
  • an organic light-emitting material with a narrow emission spectrum with an emission peak wavelength from 495 nm to 630 nm can be obtained, for example, the half-peak width of the emission spectrum is less than or equal to 65 nm.
  • organic molecules that emit light in the green to red region and have narrow-spectrum TADF luminescence characteristics.
  • Such organic molecules and their compositions with some materials can be used as luminescent materials to prepare organic electroluminescence.
  • the light-emitting layer of the device, the organic electroluminescent device prepared here has the advantages of narrow emission spectrum, high efficiency, and high color purity of the device.
  • the present disclosure provides a boron-nitrogen compound having the structure shown in formula I or II,
  • Each occurrence of R 1 is independently H, D (deuterium), fluorine, CN, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 3 -C 10 cycloalkyl, C 6 -C 14 aryl, C 6 -C 14 aryl substituted by one or more Ra , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more Ra , Diphenylamino, or diphenylamino substituted with one or more Ra ;
  • E is a single key
  • R 11 and R 22 are independently H, D (deuterium), C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
  • R is:
  • R 4 , R 5 and R 6 is independently H, D (deuterium), fluorine, CN, C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 3 -C 10 cycloalkane aryl, C 6 -C 14 aryl, C 6 -C 14 aryl substituted by one or more R d , 5- to 18-membered heteroaryl, or 5- to 18 substituted by one or more R d -membered heteroaryl;
  • Each occurrence of R a is independently D (deuterium), fluorine, CN, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 3 -C 10 cycloalkyl, C 6 -C 14 aryl group, C 6 -C 14 aryl substituted by one or more R b , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R b , diphenylamine group, or diphenylamino group substituted by one or more R b ;
  • Each occurrence of R b is independently D (deuterium), fluorine, CN, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 3 -C 10 cycloalkyl, C 6 -C 14 aryl base, C 6 -C 14 aryl substituted by one or more R c , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R c , diphenylamine group, or diphenylamino group substituted by one or more R c ;
  • R c is independently D (deuterium), fluorine, CN, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 3 -C 10 cycloalkyl, C 6 -C 14 aryl group, C 6 -C 14 aryl substituted by one or more R d , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R d , diphenylamine group, or diphenylamino group substituted by one or more R d ;
  • R d is independently D (deuterium), fluorine, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 3 -C 10 cycloalkyl, C 6 -C 14 aryl, or C 6 -C 14 aryl substituted by one or more R e ;
  • R e is independently D (deuterium), fluorine, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, C 3 -C 10 cycloalkyl, or C 6 -C 14 aryl ;
  • alkyl, alkoxy, cycloalkyl, aryl, and heteroaryl are optionally substituted by one or more substituents selected from the group consisting of halogen, -CN, C 1 -C 12 alkyl, C 1 - C 12 alkoxy, C 1 -C 12 haloalkyl, C 2 -C 6 alkenyl, C 3 -C 10 cycloalkyl, C 6 -C 14 aryl, or 5- to 18-membered heteroaryl.
  • each occurrence of R 1 is independently H, F, CF 3 , C 1 -C 20 alkyl, C 1 -C 20 alkoxy, cyclohexyl, adamantyl, phenyl, naphthyl, phenyl substituted by one or more Ra , carbazolyl, carbazolyl substituted by one or more Ra , diphenylamino, or diphenyl substituted by one or more Ra Anilino, the R a is selected from C 1 -C 6 alkyl, C 1 -C 6 fluoroalkyl and C 1 -C 6 alkoxy.
  • each occurrence of R4, R5 and R6 is independently H, F, CF3 , C1 - C20 alkyl, C1 - C20 alkoxy, cyclo Hexyl, adamantyl, phenyl, naphthyl, phenyl substituted by one or more R d , carbazolyl and carbazolyl substituted by one or more R d selected from C 1 to C 12 alkyl, C 1 -C 12 fluoroalkyl, C 1 -C 12 alkoxy, phenyl and phenyl substituted with one or more Re selected from C 1 -C 6 Alkyl, C 1 -C 6 fluoroalkyl and C 1 -C 6 alkoxy.
  • each occurrence of R 11 and R 22 is independently H, methyl, methoxy or CF 3 .
  • the frontier molecular orbitals of the boron-nitrogen compounds of Formulas I and II have the following characteristics:
  • HOMO and LUMO are distributed alternately on the ring atoms of ring c11, ring c12, ring c13, ring c14, ring b1 of formula I and one B and two N which are connected to three of the rings at the same time.
  • HOMO is distributed on the two Ns, and LUMO is distributed on the B atom, ring m1 and ring ph1;
  • HOMO and LUMO are distributed alternately on the ring atoms of ring c21, ring c22, ring c23, ring c24, ring b2 of formula II and one B and two N which are connected to three of the rings at the same time.
  • the HOMO is distributed on the two Ns, and the LUMO is distributed on the B atom, ring m2 and ring ph2.
  • the emission peaks of the emission spectra of the compounds of formula I and II are at 490-630 nm and the half-peak width of the emission spectra is less than or equal to 60 nm.
  • the emission peaks of the emission spectra of the compounds of formula I and II are 500-600 nm and the half-peak width of the emission spectrum is less than or equal to 60 nm.
  • E is a single bond or a benzene ring; each occurrence of R is independently H, methyl, tert-butyl, phenyl, 4-tolyl, 3-tolyl, 3 ,5-xylyl, 4-tert-butylphenyl, 3-tert-butylphenyl, 3,5-di-tert-butylphenyl, diphenylamino, bis(p-tolyl)amino, or bis( p-tert-butylphenyl)amino; R 11 and R 22 are H; R is H or R 4 and R 6 are the same and are tert-butyl, phenyl, 4-tolyl, 3-tolyl, 3,5-xylyl, 4-tert-butylphenyl, 3-tert-butylphenyl, 3 ,5-di-tert-butylphenyl, 4-C 1 -C 10 alkoxyphenyl, 3-C
  • the molecular structure composition of the compounds represented by formulas I and II satisfies the following definitions:
  • the compound represented by formula I and II is any one of the following compounds:
  • the present disclosure also provides a method for preparing the above-mentioned boron-nitrogen compound, which comprises the steps shown in the following reaction formulas (1) and (2):
  • the carbazole skeleton-containing boron nitrogen core compound is used as the reactant, which is dissolved in an organic solvent, heated to reflux in the presence of a catalyst, and the para-hydrogen atom of the boron atom of the b benzene ring is activated. and replaced by boron ester;
  • the electron-withdrawing group is introduced into the boron-nitrogen skeleton by using the Suzuki reaction, and the introduced electron-withdrawing group is located in the para position of the B atom of the b benzene ring in the boron-nitrogen skeleton;
  • ArX is any one of the following three molecules:
  • X is Br or Cl
  • R 1 , R 4 , R 5 , R 6 , R 11 , R 22 , and R are as defined above.
  • the compound of formula I described in the present disclosure can be prepared according to conventional chemical synthesis methods in the art, and its steps and conditions can refer to the steps and conditions of similar reactions in the art.
  • the present disclosure provides a preparation method of compounds represented by formulas (I and II, which may include the following schemes:
  • the present disclosure also provides an organic electroluminescent device comprising an anode, an emission layer, an optional hole injection layer, an optional hole transport layer, an optional electron transport layer, an optional electron injection layer, and a cathode , wherein at least one layer of the light-emitting layer, the electron injection layer, the electron transport layer, the hole transport layer, and the hole injection layer contains the above-mentioned boron nitride compound.
  • the organic electroluminescent devices of the present disclosure may also include an optional hole blocking layer, an optional electron blocking layer, an optional capping layer, and the like.
  • the organic electroluminescent device has the structure shown in Figure 1, wherein 1 is an ITO anode, 2 is a hole injection layer, 3 is a hole transport layer, 4 is a light-emitting layer, and 5 is an electron The transport layer, 6 is the electron injection layer, and 7 is the metal cathode.
  • the boron nitride compound represented by formula I or II is used to prepare a light-emitting layer in an organic electroluminescent device.
  • the boron nitride compound represented by formula I or II is used to prepare a light-emitting layer in an organic electroluminescent device, and the molecular structures of the compounds represented by I and II are defined as follows:
  • the boron nitride compounds represented by formulae BN-1 to BN-584 are used to prepare light-emitting layers in organic electroluminescent devices.
  • the organic electroluminescent device further includes a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer sequentially formed on the substrate; the organic light-emitting functional layer includes
  • the light-emitting layer containing the above-mentioned boron nitride compound may further comprise any one or a combination of any one of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer .
  • the present disclosure provides an organic electroluminescent composition
  • a boron nitride compound as represented by formula I or II and a host material; the host material is capable of transporting electrons and/or holes And its triplet excited state energy is higher than or close to the triplet excited state energy of the doped material.
  • the host material in the organic electroluminescent composition may be a carbazole derivative and/or a carboline represented by formulae (H-1) to (H-6) derivative.
  • the organic electroluminescent composition preferably contains 0.3-30.0wt% (weight percentage) any compound represented by formula I or II as a doping material, and the remaining 99.7-70.0wt% components are formula (H -1)
  • the host material contains two compounds of formulae (H-1) to (H-6) in a weight ratio of 1:5 to 5:1.
  • 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.
  • R 1H and R 2H are independently any of the following:
  • 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.
  • 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 host material in the organic electroluminescent composition is 1-2 kinds of compounds H1-1 to H1-427; in the organic electroluminescent composition, It contains 0.3-30.0wt% (weight percentage) of any compound represented by formula I or II, and the remaining 99.7-70.0wt% components are 1-2 compounds among compounds H1-1 to H1-427.
  • the organic electroluminescent composition contains two compounds of formula H1-1 to H1-427 as host materials, and the weight ratio of the two compounds is 1:5 to 5: 1.
  • the dopant material in the organic electroluminescent composition is any compound represented by formula I or II (the content is 0.3wt%-30.0wt%); the host material ( content of 99.7wt%-70.0wt%) is represented by any one of the 1,3,5-triazine derivatives represented by formulae Trz1-A, Trz2-A and Trz3-A and formulae H-1 to H-6 The composition of any of the compounds shown.
  • the 1,3,5-triazine derivatives represented by Trz1-A, Trz2-A or Trz3-A in the host material are combined with H-1, H-2, H-3, H- 4.
  • the weight ratio between the compounds represented by H-5 or H-6 is 1:5 to 5:1.
  • R 1a , R 1b , R 2a , R 2b , R 3a and R 3b are independently R Tz , and the rest are the same or different 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;
  • the dopant material in the organic electroluminescent composition is any compound represented by formula I or II (the content is 0.3wt%-30.0wt%); the host material ( The content is 99.7wt%-70.0wt%) by any one of 1,3,5-triazine derivatives represented by formulae TRZ-1 to TRZ-56 and carbazole or carbazole represented by formulae H1-1 to H1-427 Any of the morpholine derivatives.
  • the weight ratio between the 1,3,5-triazine derivative and the carbazole or carboline derivative in the host material is 1:5 to 5:1.
  • the present disclosure provides an application of the organic electroluminescent composition as described above as an organic electroluminescent material.
  • the organic electroluminescent composition is used to prepare a light-emitting layer in an organic electroluminescent device.
  • the present disclosure also provides an organic electroluminescent device comprising an anode, an emission layer, an optional hole injection layer, an optional hole transport layer, an optional electron transport layer, an optional electron injection layer, and a cathode , wherein at least one layer of the light-emitting layer, the electron injection layer, the electron transport layer, the hole transport layer, and the hole injection layer comprises the organic electroluminescence composition as described above.
  • the light-emitting layer of the organic electroluminescent device comprises an organic electroluminescent composition as described above.
  • the organic electroluminescent composition is a light-emitting layer, and the light-emitting principle of the light-emitting layer is based on the energy transfer from the host material to any compound represented by formula I or II or the loading of the light-emitting material itself. Stream capture.
  • the organic electroluminescent composition is a light-emitting layer; the host material in the organic electroluminescent composition can be as formula (H-1) to (H-6) The carbazole derivatives and/or carboline derivatives shown.
  • the organic electroluminescent composition contains 0.3-30.0 wt % of any compound represented by formula I or II, and the remaining 99.7-70.0 wt % components are formula (H-1) The main body composed of 1-2 compounds in (H-6). For example, when the host contains two compounds of formulae (H-1) to (H-6), the weight ratio of the two compounds is 1:5 to 5:1.
  • the organic electroluminescent composition is a light-emitting layer; the host material in the composition is 1-2 kinds of compounds H1-1 to H1-427.
  • the organic electroluminescent composition contains 0.3-30.0wt% of any compound represented by formula I or II, and the remaining 99.7-70.0wt% components are compounds H1-1 to 1-2 compounds in H1-427.
  • the weight ratio of the two compounds is 1:5 to 5:1.
  • the organic electroluminescent composition is a light-emitting layer;
  • the dopant material in the organic electroluminescent composition is any compound represented by formula I or II ( The content is 0.3wt-30.0wt%);
  • the host material content is 99.7wt-70.0wt%) is composed of any of the 1,3,5-triazine derivatives shown in formula Trz1-A, Trz2-A and Trz3-A One and any one of the compounds represented by formulae H-1 to H-6.
  • 1,3,5-triazine derivatives represented by Trz1-A, Trz2-A or Trz3-A are combined with H-1, H-2, H-3, H-4, H
  • the weight ratio between the compounds represented by -5 or H-6 is 1:5 to 5:1.
  • the organic electroluminescent composition is a light-emitting layer;
  • the dopant material in the organic electroluminescent composition is any compound represented by formula I or II ( The content is 0.3wt-30.0wt%);
  • the host material content is 99.7wt-70.0wt%) is composed of any one of the 1,3,5-triazine derivatives shown in the formula TRZ-1 to TRZ-56 and the formula It is composed of any one of the carbazole or carboline derivatives represented by H1-1 to H1-427.
  • the weight ratio between the 1,3,5-triazine derivative and the carbazole or carboline derivative is 1:5 to 5:1.
  • the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any of the formulas BN-1 to BN-584.
  • a compound (content is 0.3wt-30.0wt%); the host material (content is 99.7wt-70.0wt%) is composed of any of the 1,3,5-triazine derivatives shown in formula TRZ-1 to TRZ-56 It is composed of any one of the carbazole or carboline derivatives represented by the formulae H1-1 to H1-427.
  • the weight ratio between the 1,3,5-triazine derivative and the carbazole or carboline derivative is 1:5 to 5:1.
  • the organic electroluminescent device further includes a substrate, and an anode layer, an organic light-emitting functional layer and a cathode layer sequentially formed on the substrate;
  • the organic light-emitting functional layer includes
  • the light-emitting layer containing the organic electroluminescent composition as described above may further comprise any one of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer, or various combinations.
  • the present disclosure provides an application of the organic electroluminescence device in an organic electroluminescence display or an organic electroluminescence illumination light source.
  • the present disclosure provides a molecular structure design method for designing and synthesizing organic light-emitting materials, which has the advantages of combining the advantages of the isolated D-A structure and the resonance D-A molecule, and overcoming the disadvantages of these two types of molecules.
  • the existing green and red organic electroluminescent materials can effectively overcome the defects of excessively broad emission spectrum, and provide an organic molecule that emits light in the green-red region and even near-infrared and has narrow-spectrum emission characteristics.
  • Design synthesis and preparation technology methods and further provide an organic compound and composition that emits light in the green to red light region and has narrow-spectrum emission characteristics as shown in formulas I and II, and its use in the field of organic electroluminescence Applications.
  • the organic molecules provided by the present disclosure and their compositions with some materials can be used as light-emitting materials to prepare the light-emitting layer of the organic electroluminescent device, and the organic electroluminescent device prepared here has a narrow emission spectrum (relative to the separated D-A structure emitting light) The electroluminescence spectrum of the material), high efficiency and high efficiency.
  • the present disclosure provides a synthesis method for coupling a tricoordinate B complex of 1,3-dicarbazole (or its derivative) benzene with a pyrimidine derivative.
  • the advantage of the synthesis method is that it can combine electron withdrawing properties
  • the pyrimidine derivative group is coupled with the C atom occupied by the LUMO orbital in the tricoordinate B resonance framework, so based on this synthesis method, pyrimidine derivatives with a conjugated structure and strong electron withdrawing properties can be effectively synthesized groups are introduced into the tricoordinate B resonance framework.
  • R 1 and Ar are as previously described.
  • the UV-Vis absorption spectrum of the sample film was measured by a LAMBDA 35 UV-Vis spectrophotometer of PerkinElmer Company.
  • the fluorescence spectrum was measured by the RF-5301PC fluorescence photometer of Shimadzu Company in Japan, and the excitation wavelength selected during the test was the maximum absorption wavelength.
  • the raw material-1 used includes the following molecules:
  • the raw material-2 used includes the following molecules:
  • the raw material-3 used includes the following molecules:
  • the basic process route of the compound synthesis involved in the present disclosure is as follows, and the reaction is divided into four steps.
  • the first two steps are the synthesis of BNCz parent nucleus; the core of the final product synthesis is the successful preparation of the precursor BN-Bpin.
  • the carbazole skeleton-containing boron nitrogen raw material (6.5 mmol) and 1.7 g of pinacol diboronate (6.5 mmol) were added to tetrahydrofuran (60 mL), and the mixture was bubbled with nitrogen for 10 minutes, and 34.9 mg of 4,4'-di-tert-butyl-2,2'-bipyridine (0.13 mmol) and 43.1 mg of methoxy(cyclooctadiene)iridium dimer (0.065 mmol) were added under high flow of nitrogen . After stirring for 10 minutes, the mixture was heated to reflux and stirred for 24 hours. After the reaction system was cooled to room temperature, it was directly concentrated under reduced pressure and purified by column chromatography to obtain the precursor BN-Bpin.
  • BN-203 S1 S2-1 S3-43 1401.79 C, 85.68; H, 7.55; N, 6.00 twenty one BN-204 S1 S2-1 S3-44 1401.79 C, 85.68; H, 7.55; N, 6.00 20 BN-205 S1 S2-1 S3-45 1065.14 C, 85.70; H, 5.39; N, 7.89 17 BN-206 S1 S2-1 S3-46 1065.14 C, 85.70; H, 5.39; N, 7.89 twenty three BN-207 S1 S2-1 S3-47 1401.79 C, 85.68; H, 7.55; N, 6.00 twenty one BN-208 S1 S2-1 S3-48 1465.79 C, 81.94; H, 7.22; N, 5.73 twenty two BN-209 S1 S2-1 S3-49 1353.57 C, 81.64; H, 6.63; N, 6.21 20 BN-210 S1 S2-1 S3-50 1121.25 C, 85.70; H, 5.84; N
  • BN-434 S1 S2-4 S3-82 1111.21 C, 88.63; H, 5.35; N, 5.04 17 BN-435 S1 S2-4 S3-83 1532.02 C, 87.81; H, 7.83; N, 3.66 15 BN-436 S1 S2-4 S3-84 1628.02 C, 82.63; H, 7.37; N, 3.44 twenty three BN-437 S1 S2-4 S3-85 1179.25 C, 89.63; H, 4.70; N, 4.75 twenty one BN-438 S1 S2-4 S3-86 1207.30 C, 89.54; H, 4.93; N, 4.64 15 BN-439 S1 S2-4 S3-87 1229.39 C, 88.91; H, 5.66; N, 4.56 20 BN-440 S1 S2-4 S3-88 1229.39 C, 88.91; H, 5.66; N, 4.56 20 BN-440 S1 S2-4 S3-88 1229.39 C, 88.91;
  • the compounds represented by formulae BN-1 to BN-584 are the molecular structures of the materials provided by the present disclosure (the specific molecular structures are shown above), and the compounds represented by BN-R-1 to BN-R-7 are the molecular structures of the comparative materials.
  • the comparison between the luminescent peak positions of the luminescent compounds provided by the present disclosure and the luminescent peak positions of the corresponding comparative compounds listed in Table 2 shows that the luminescent peak positions of the luminescent compounds provided by the present disclosure are red-shifted by 7- to the luminescent peak positions of the corresponding comparative compounds. 62nm, that is, a shift of 7-62nm to long wavelengths.
  • the luminescence peak of the boron-nitrogen compound of the present disclosure has a significant red shift relative to its isomer, and the half-peak width of the luminescence spectrum is not significantly deteriorated (still narrow), so the luminescent molecule design provided by the present disclosure
  • the principles and methods are effective in providing a luminescent material with a narrow emission peak in the green to red region.
  • Substrate treatment transparent ITO glass is used as the base material for preparing the device, and then ultrasonically treated with 5% ITO lotion for 30 min, followed by distilled water (2 times), acetone (2 times), and isopropanol (2 times) ) ultrasonically washed, and finally the ITO glass was stored in isopropanol. Before each use, carefully wipe the surface of the ITO glass with acetone cotton balls and isopropyl alcohol cotton balls, rinse with isopropyl alcohol, dry, and then treat with plasma for 5 minutes for use. The fabrication of the device is accomplished by a combination of spin coating and vacuum evaporation.
  • Preparation of light-emitting layer Dissolve the host material and light-emitting material in xylene according to the ratio of 97wt%:3wt% (wt% is the weight percentage concentration) to prepare a solution with a concentration of 2wt%, and use the prepared solution by spin coating method.
  • a light-emitting layer was prepared, and the thickness of the light-emitting layer was 50 nm.
  • the electron transport layer, electron injection layer and metal electrode are prepared by evaporation process.
  • the deposition rate is determined by the Sainz film thickness meter, and the organic electron transport layer, the LiF electron injection layer and the metal Al electrode are sequentially deposited on the light-emitting layer by the vacuum evaporation process (see the following effect example for the specific device structure).
  • the deposition rate of organic material is The deposition rate of LiF is The deposition rate of Al is
  • the current, voltage, brightness, luminescence spectrum and other characteristics of the device were tested synchronously with Photo Research PR 655 spectral scanning luminance meter and Keithley K 2400 digital source meter system.
  • the performance test of the device was carried out at room temperature under ambient atmosphere.
  • the external quantum efficiency (EQE) of the device is calculated from the current density, brightness and electro-spectrum combined with the visual function when the luminescence is Lambertian distribution.
  • PEDOT:PSS is used as the hole injection layer
  • Poly-HTL is used as the hole transport layer
  • H1-48 is used as the hole transport layer in the light-emitting layer.
  • Host materials, BN-1 to BN-584 were used as doped light-emitting materials (3 wt % doping concentration)
  • TmPyPB was used as electron transport material
  • LiF was used as electron injection layer
  • Al was used as metal cathode.
  • the results of the effect examples are shown in Table 3.
  • the electroluminescence device effect implementation data listed in Table 3 proves that the luminescent materials provided by the present disclosure can be used to prepare high-efficiency organic electroluminescence devices, and the electroluminescence spectrum has narrow band characteristics, and the electroluminescence spectrum is half of the The peak width is less than 60 nm.
  • PEDOT:PSS is used as the hole injection layer
  • Poly-HTL is used as the hole injection layer.
  • the hole transport layer is used, and the mixture of H1-33 and TRZ-1 is used as the host material in the light-emitting layer (the weight mixing ratio of H1-33 and TRZ-1 is 1:1), and BN-1 to BN-584 are used as dopant materials respectively.
  • a hetero light-emitting material (doping concentration of 3 wt %) was used, TmPyPB was used as an electron transport material, LiF was used as an electron injection layer, and Al was used as a metal cathode.
  • the organic electroluminescent device structure is [ITO/PEDOT:PSS(20nm)/Poly-HTL(50nm)/H1-33:TRZ-1+3wt%BN-n/TmPyPB(50nm)/LiF(1nm) /Al(100nm)].
  • n 1-584.
  • the results of the effect examples are shown in Table 4.
  • the implementation data of electroluminescence device effects listed in Table 4 proves that the luminescent materials provided by the present disclosure can be used to prepare high-efficiency organic electroluminescence devices, and the electroluminescence spectrum has narrow-band characteristics, half of the electroluminescence spectrum. The peak width is less than 60 nm.
  • the results of the effect examples are shown in Table 4.

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Abstract

L'invention concerne un composé bore-azote représenté par la formule (I) ou (II), une composition contenant le composé et une application de celui-ci dans le domaine de l'électroluminescence organique. L'invention concerne également un procédé de préparation d'un composé bore-azote représenté par la formule (I) ou (II). Un dispositif électroluminescent organique fabriqué à l'aide du composé ou de la composition de la présente invention permet d'obtenir une électroluminescence verte et rouge efficace ayant une émission spectrale étroite.
PCT/CN2021/136306 2020-12-10 2021-12-08 Composé bore-azote, composition électroluminescente organique et dispositif électroluminescent organique le contenant WO2022121920A1 (fr)

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CN115557979A (zh) * 2022-10-27 2023-01-03 深圳大学 一种硼氮杂化合物及其制备方法、有机电致发光器件

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