TW202222808A - Boron-nitrogen compound, organic electroluminescence composition, and organic electroluminescence device comprising the same - Google Patents

Abstract

The present invention provides a boron-nitrogen compound of formula (I) or formula (II), a composition comprising the compound, and an application of the compound and the composition in the field of organic electroluminescence. The present invention also provides methods for preparing the boron-nitrogen compound of formula (I) or formula (II). An organic electroluminescence device prepared by using the provided compound or composition can achieve efficient green and red electroluminescence with narrow spectral emission.

Description

A boron-nitrogen compound, organic electroluminescent composition and organic electroluminescent device comprising the same

Embodiments of the present invention 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 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. At present, 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%. The efficiency is generally lower than 5%, and there is still a big gap with the efficiency of phosphorescent devices. At present, fluorescent electroluminescent devices that can break through the internal quantum efficiency limit of 25% mainly use the delayed fluorescence mechanism, which can effectively utilize the triplet excited state energy in the device. There are two main types of delayed fluorescence mechanisms: (1) TTA (Triplet-Triplet Annihilation) mechanism; (2) TADF (Thermally Activated Delayed Fluorescence, Thermally Activated Delayed Fluorescence) mechanism. 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%-62.5%. The TADF mechanism utilizes small organic molecules with a small singlet-triplet energy level difference ( ΔE _ST ), and its triplet excitons can be converted into a reverse intersystem crossing (RISC) process under ambient thermal energy. The mechanism of singlet excitons. Theoretically, the internal quantum efficiency of the device can reach 100%. However, 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).

結構 1.D-A型分子結構 Different from traditional fluorescent molecular localized state (LE) emission, 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 DA structure (Structure 1) , its electron donor group and electron acceptor group are separated in space, and this type of molecule is defined as: isolated DA structure . This DA-type 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 DA-type structure, it is easy to realize the regulation of the peak position (wavelength) of the emission spectrum, that is, the emission color, because the structure of the electron donor and the electron acceptor and the relative ability to gain or lose electrons are easy to optimize. However, the DA structure shown in structure 1 can easily lead to the change of configuration and conformation when the molecule is in the ground state and excited state, and generate abundant molecular vibration modes. Most of these luminescent molecules have emission spectra with half-peak widths exceeding 100 nm. 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.

Structure 1. DA-type molecular structure

結構 2.基於三配位B-N配合物分子模型結構。 2018, 130, 11486; J. Am. Chem. Soc., 2018, 140, 1195; Adv. Mater. 2016, 28, 2777; CN109155368A; WO2016/152544A1; WO2017/188111A1; WO2018/150832A1; WO2018/186374A1; WO2018/216990A1) some tri-coordinated B (boron)-based light-emitting compounds, which are structurally characterized in that the light-emitting compounds contain at least one B atom coordinated with three benzene rings to form a very rigid organic compound. The chromophore core structure, and the three benzene rings that coordinate with B are covalently linked to N. Such molecules are called BN complexes (structure 2), that is, the compounds are formed by the coordination of aromatic amine organic molecules with B. Luminescent compounds.

Structure 2. Molecular model structure based on tricoordinate BN complexes.

The frontier molecular orbitals of such tricoordinate B complexes have a characteristic that the highest occupied molecular orbital (HOMO: the highest occupied molecular orbital) and the lowest unoccupied molecular orbital (LUMO: the lowest unoccupied molecular orbital) are alternately arranged (the so-called so-called The resonance structure) is distributed in the coordination system, with B in the LUMO orbital and N in the HOMO orbital. Due to its unique HOMO and LUMO alternating electronic structure (resonance structure), this type of BN complex has excited state charge transfer and TADF luminescence properties (this type of molecule is defined as: resonance type DA molecule ), and it is very important. Its emission spectral band is very narrow, and the half-peak width of the emission spectrum can reach about 20 nm. Based on these compounds, high-performance blue or sky blue (the peak of the luminescence spectrum is between 450 and 490 nm) organic electroluminescent devices can be prepared, and the electroluminescence spectrum is very narrow (the half-peak width is about 25 nm). However, based on this resonant BN coordination structure, materials with narrow emission spectrum for green light (with the emission peak between 520 and 535 nm) and red light (with the emission peak between 625 and 640 nm) have not yet been prepared. 's report. The main reason is that although the molecules with the emission peaks in the green or even red region can be obtained by expanding the degree of aromatic amine conjugation, the expansion of the conjugation system will destroy the electronic structure of the alternate layout of HOMO and LUMO, thus resulting in a change in the emission spectrum. Broad, narrow-spectrum emitting materials cannot be obtained.

Therefore, there is still a need for new green and red organic electroluminescent materials with narrow spectral emission characteristics.

The following is an overview of the subject matter detailed in this specification. This summary is not intended to limit the scope of protection of the patentable scope of the invention.

In order to overcome the defect that the emission spectrum of the existing green light and red light organic electroluminescent materials is too wide, the present invention provides an organic compound, a composition and an organic electroluminescent light that emits light in the green light to red light region and has narrow-spectrum TADF luminescence characteristics. light-emitting device.

The present invention provides a boron-nitrogen compound having the structure shown in formula I or II,

； R ¹¹和R ²²每次出現時獨立地為H、D(氘)、C ₁~C ₆烷基或C ₁~C ₆烷氧基； R為：

、H、C ₁~C ₂₀烷基、C ₁~C ₂₀烷氧基、C ₃~C ₁₀環烷基、C ₆~C ₁₄芳基、被一個或複數個R ^d取代的C ₆~C ₁₄芳基、5-至18-元雜芳基或被一個或複數個R ^d取代的5-至18-元雜芳基； R ⁴、R ⁵和R ⁶每次出現時獨立地為H、D(氘)、氟、CN、C ₁~C ₂₀烷基、C ₁~C ₂₀烷氧基、C ₃~C ₁₀環烷基、C ₆~C ₁₄芳基、被一個或複數個R ^d取代的C ₆~C ₁₄芳基、5-至18-元雜芳基或被一個或複數個R ^d取代的5-至18-元雜芳基； R ^a每次出現時獨立地為D(氘)、氟、CN、C ₁~C ₁₂烷基、C ₁~C ₁₂烷氧基、C ₃~C ₁₀環烷基、C ₆~C ₁₄芳基、被一個或複數個R ^b取代的C ₆~C ₁₄芳基、5-至18-元雜芳基、被一個或複數個R ^b取代的5-至18-元雜芳基、二苯胺基、或者被一個或複數個R ^b取代的二苯胺基； R ^b每次出現時獨立地為D(氘)、氟、CN、C ₁~C ₁₂烷基、C ₁~C ₁₂烷氧基、C ₃~C ₁₀環烷基、C ₆~C ₁₄芳基、被一個或複數個R ^c取代的C ₆~C ₁₄芳基、5-至18-元雜芳基、被一個或複數個R ^c取代的5-至18-元雜芳基、二苯胺基、或者被一個或複數個R ^c取代的二苯胺基； R ^c每次出現時獨立地為D(氘)、氟、CN、C ₁~C ₁₂烷基、C ₁~C ₁₂烷氧基、C ₃~C ₁₀環烷基、C ₆~C ₁₄芳基、被一個或複數個R ^d取代的C ₆~C ₁₄芳基、5-至18-元雜芳基、被一個或複數個R ^d取代的5-至18-元雜芳基、二苯胺基、或者被一個或複數個R ^d取代的二苯胺基； R ^d每次出現時獨立地為D(氘)、氟、C ₁~C ₁₂烷基、C ₁~C ₁₂烷氧基、C ₃~C ₁₀環烷基、C ₆~C ₁₄芳基或者被一個或複數個R ^e取代的C ₆~C ₁₄芳基； R ^e每次出現時獨立地為D(氘)、氟、C ₁~C ₁₂烷基、C ₁~C ₁₂烷氧基、C ₃~C ₁₀環烷基、或者C ₆~C ₁₄芳基； 上述烷基、烷氧基、環烷基、芳基、雜芳基任選被一個或複數個選自以下的取代基所取代：鹵素、-CN、C ₁~C ₁₂烷基、C ₁~C ₁₂烷氧基、C ₁~C ₁₂鹵代烷基、C ₂~C ₆烯基、C ₃~C ₁₀環烷基、C ₆~C ₁₄芳基、或者5-至18-元雜芳基。 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 , Diphenylamine group, or diphenylamine group substituted by one or more R ^a ; E is a single bond or

; R ¹¹ and R ²² are independently H, D (deuterium), C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy at each occurrence; R is:

, H, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₆ -C ₁₄ aryl, C ₆ -C substituted by one or more R ^d ₁₄ -aryl, 5- to 18-membered heteroaryl, or 5- to 18-membered heteroaryl substituted with one or more R ^d ; R ⁴ , R ⁵ and R ⁶ are each 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, by one or more R ^d Substituted C ₆ ~C ₁₄ aryl, 5- to 18-membered heteroaryl or 5- to 18-membered heteroaryl substituted by one or more R ^; R 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, substituted by one or more R ^b C ₆ ~C ₁₄ aryl, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R ^b , diphenylamino, or substituted by one or more R ^b The diphenylamino group; 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, 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 Aryl, diphenylamino, or diphenylamino substituted by one or more R ^c ; each occurrence of 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, C ₆ -C ₁₄ aryl substituted by one or more R ^d , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl, diphenylamino, or diphenylamino substituted with one or more R ^{d ;} each occurrence of 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 substituted by one or more R ^e ₁₄ Aryl; each occurrence of ^Re 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; The above-mentioned alkyl, alkoxy, cycloalkyl, aryl, and heteroaryl are optionally substituted by one or more substituents selected from the following groups: halogen, -CN, C ₁ ~C ₁₂ alkane base, 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.

在反應式(1)中以含咔唑骨架的硼氮母核化合物為反應物，將其溶解在有機溶劑中，在催化劑的存在下加熱回流，b苯環的硼原子對位氫原子被活化並被硼酯取代； 在反應式(2)中利用Suzuki反應將吸電子基團引入到硼氮骨架上，被引入的吸電子基團位於硼氮骨架中b苯環的B原子的對位； 在反應式(2)中，ArX為如下三種分子中的任一種：

、

、

； X為Br或Cl； R ¹、R ⁴、R ⁵、R ⁶、R ¹¹、R ²²、R的定義如前所述。 In another aspect, the present invention provides a method for preparing the above-mentioned boron-nitrogen compound, which comprises the steps shown in the following reaction formulas (1) and (2):

In the reaction formula (1), 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 is substituted by boron ester; In the reaction formula (2), 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; In the reaction formula (2), 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.

In another aspect, the present invention provides an organic electroluminescent composition comprising the above-mentioned boron-nitrogen compound. Further, the present invention also provides an organic electroluminescence composition comprising the above-mentioned boron nitride compound and a host material.

In yet another aspect, the present invention provides an organic electroluminescence device, which comprises the above-mentioned boron nitride compound or organic electroluminescence composition.

Other aspects will become apparent upon reading and understanding of the drawings and detailed description.

The technical means of the embodiments of the present invention will be clearly and completely described below with reference to the drawings of the embodiments of the present invention. Obviously, the described embodiments are some, but not all, embodiments of the present invention. Based on the described embodiments of the present invention, all other embodiments obtained by those with ordinary knowledge in the technical field without creative efforts shall fall within the protection scope of the present invention.

It should be understood that any and all embodiments of the present invention may be combined with technical features of any other embodiment or a plurality of other embodiments to obtain further embodiments, provided that there is no conflict. The present invention encompasses such combinations resulting in additional embodiments.

All publications and patents mentioned in the present invention are hereby incorporated by reference in their entirety, and so forth. To the extent that the usage or terminology used in any publications and patents incorporated by reference conflicts with the usage or terminology used in the present invention, the usage and terminology of the present invention shall control.

Section headings used in this specification are for the purpose of organizing the article only and should not be construed as limitations on the subject matter described.

Unless otherwise defined, all technical and scientific terms used in this specification have the ordinary meaning in the art to which the claimed subject matter belongs. If multiple definitions exist for a term, the definitions in this specification shall prevail.

Unless otherwise stated, when disclosing or claiming a range of any type (eg, wavelength, half width, and number of substituents), it is intended to separately disclose or claim each possible value that the range could reasonably cover, including those encompassed in any subrange within it. For example, the numerical ranges defined in the substituents in this specification, such as 0 to 6, 1 to 4, 1 to 3, etc., indicate integers within the range, wherein 0 to 6 should be understood to include 0, 1, 2, 3, 4, 5 , 6, also includes 1~4 and 1~3.

Words like "including", "containing" or "comprising" used in the present invention mean that the elements appearing before the word cover the elements listed after the word and their equivalents, and do not exclude unrecited elements. The terms "comprising" or "including (including)" as used in this specification can be open, semi-closed and closed. In other words, the term also includes "consisting essentially of," or "consisting of."

The terms "moiety", "structural moiety", "chemical moiety", "group", "chemical group" as used in this specification refer 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.

It should be understood that singular forms (eg, "a") used in the present invention may include plural referents unless stated otherwise.

Unless otherwise indicated, the present invention 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 invention 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 invention may contain unnatural proportions of atomic isotopes at one or more of the atoms that make up the compound. For example, compounds can be labeled with isotopes, such as deuterium (D). All alterations in the isotopic composition of the compounds of the present invention, whether radioactive or not, are included within the scope of the present invention.

The reagents and raw materials used in the present invention are commercially available or can be prepared by conventional chemical synthesis methods.

This specification uses the term "optional" to describe an event, meaning that the event may or may not occur. For example, arbitrarily fused to a ring means that it is fused to a ring or not to a ring. For example, the term "optionally substituted" as used in this specification refers to being unsubstituted or having at least one non-hydrogen substituent that does not destroy the luminescent properties possessed by unsubstituted analogs.

In the present invention, unless otherwise specified, the number of the "substitution" can be one or plural; when there is plural, it can be two, three or four. In addition, when the number of the "substitution" is plural, the "substitution" may be the same or different.

In the present invention, the position of "substitution" can be arbitrary unless otherwise specified.

In the present invention, 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%.

In the present invention, the deuterium is D or ² H, also known as deuterium, and the abundance of deuterium at the deuterium substitution site is greater than 95%.

Definitions of standard chemical terms can be found in references including Carey and Sundberg "ADVANCED ORGANIC CHEMISTRY 4TH ED." Vols. A (2000) and B (2001), Plenum Press, New York.

In this specification, groups and their substituents can be selected by one of ordinary skill in the art to provide stable moieties and compounds. When substituents are described by conventional chemical formulae written from left to right, the substituents also include the chemically equivalent substituents that would result when the structural formula was written from right to left. For example _-CH2O- is equivalent to _-OCH2- .

As used herein, the term "halogen" or "halo" refers to fluorine, chlorine, bromine or iodine. In one embodiment, the halogen or halo agent is desirably fluoro or fluoro.

In the present invention, the term "alkyl" as a group or part of other groups (eg, as used in halogen-substituted alkyl groups and the like) is intended to include both branched and straight chains having the specified number of carbon atoms. Saturated aliphatic hydrocarbon group. For example, the C ₁ -C ₂₀ alkyl group includes straight-chain or branched-chain alkyl groups having 1 to 20 carbon atoms. As defined in "C ₁ -C ₆ alkyl", it includes a group having 1, 2, 3, 4, 5, or 6 carbon atoms in a straight or branched chain structure. For example, in the present invention, 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, ideally 1 to 4 substituents. The term "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 .

The term "alkoxy" as used in this specification refers to an alkyl group as defined above which is attached via an oxygen bond (-O-), respectively. The term "substituted alkoxy" refers to a substituted alkyl group, as defined above, attached via an oxygen bond.

In the present invention, as a group or part of other groups, the term "Cn-m aryl" 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. Examples of the above-mentioned aryl unit include phenyl, biphenyl, naphthyl, indenyl, azulenyl, fluorenyl, phenanthryl, or anthracenyl. In one embodiment, the aryl group is desirably a _C6-14 aryl group such as phenyl, biphenyl, and naphthyl, more desirably phenyl.

In the present invention, the term "n-m membered heteroaryl" as part of a group or other group means that the 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, phthalazinyl, imidazopyridyl, imidazothiazolyl, imidazoxazolyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, isoindolyl, indazolyl, pyrrolo Pyridyl, thienopyridyl, furopyridyl, benzothiadiazolyl, benzoxadiazolyl, pyrrolopyrimidinyl, thienofuranyl. In one embodiment, ideal examples of "5- to 18-membered heteroaryl groups" include furyl, thienyl, pyrrolyl, imidazolyl, thiazolyl, pyrazolyl, oxazolyl, isoxazolyl, Isothiazolyl, pyridyl, pyrimidinyl and carbazolyl, more preferably carbazolyl.

The term "fused" as used in this specification means that two or more carbocyclic or heterocyclic rings share a ring edge to form a polycyclic ring.

The term C _n -C _m cycloalkyl used in this specification 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, C ₃ -C ₁₀ cycloalkyl is ideally adamantyl or cyclohexyl.

結構 3.代表性的模型分子結構。 The present invention provides a method for designing and synthesizing organic light-emitting molecules with a luminescent peak between 495-630 nm and a narrow emission spectrum. ) and HOMO and LUMO alternate layout electronic structure (resonance structure, shown in structure 2) is different. The specific molecular design adopted by the present invention is as follows:

Structure 3. Representative model molecular structure.

Structure 3 shows the representative molecular design model structure provided by the present invention. The definition of Ar group is as described above, which is a pyrimidine derivative with electron withdrawing ability. The general method and principle of molecular design provided are: in HOMO and LUMO An additional pyrimidine derivative electron acceptor group is introduced into the functional skeleton of the alternate layout electronic structure (resonance structure), and a C (carbon) atom of the introduced pyrimidine derivative passes through a C atom on the resonance structure group. A single bond is attached, and the additional pyrimidine derivative is covalently attached by para-substitution with respect to the B atom in the resonance structure (as shown in Structure 3). Since the C atom of the additional pyrimidine derivative is connected to the C of the LUMO orbital arrangement on the resonance structure group, the LUMO orbital of the molecule provided by the present invention is formed by the LUMO orbital of the resonance structure part merged with the LUMO orbital of the additional pyrimidine derivative acceptor The HOMO orbital of the molecule provided by the present invention 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 invention is spatially 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 invention is that it combines the advantages of the isolated DA structure and the resonance type DA molecule , and overcomes the shortcomings of the two types of molecules. Since the additional pyrimidine derivative acceptor and B atom take the para-substitution 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. Using the molecular design method provided by the present invention, 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.

The technical method provided by the present invention can effectively design and synthesize organic molecules that emit light in the green to red region and have narrow-spectrum TADF luminescence characteristics, and the 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.

R ¹每次出現時獨立地為H、D(氘)、氟、CN、C ₁~C ₂₀烷基、C ₁~C ₂₀烷氧基、C ₃~C ₁₀環烷基、C ₆~C ₁₄芳基、被一個或複數個R ^a取代的C ₆~C ₁₄芳基、5-至18-元雜芳基、被一個或複數個R ^a取代的5-至18-元雜芳基、二苯胺基、或者被一個或複數個R ^a取代的二苯胺基； E為單鍵或者

； R ¹¹和R ²²每次出現時獨立地為H、D(氘)、C ₁~C ₆烷基或C ₁~C ₆烷氧基； R為：

、H、C ₁~C ₂₀烷基、C ₁~C ₂₀烷氧基、C ₃~C ₁₀環烷基、C ₆~C ₁₄芳基、被一個或複數個R ^d取代的C ₆~C ₁₄芳基、5-至18-元雜芳基或被一個或複數個R ^d取代的5-至18-元雜芳基； R ⁴、R ⁵和R ⁶每次出現時獨立地為H、D(氘)、氟、CN、C ₁~C ₂₀烷基、C ₁~C ₂₀烷氧基、C ₃~C ₁₀環烷基、C ₆~C ₁₄芳基、被一個或複數個R ^d取代的C ₆~C ₁₄芳基、5-至18-元雜芳基或被一個或複數個R ^d取代的5-至18-元雜芳基； R ^a每次出現時獨立地為D(氘)、氟、CN、C ₁~C ₁₂烷基、C ₁~C ₁₂烷氧基、C ₃~C ₁₀環烷基、C ₆~C ₁₄芳基、被一個或複數個R ^b取代的C ₆~C ₁₄芳基、5-至18-元雜芳基、被一個或複數個R ^b取代的5-至18-元雜芳基、二苯胺基、或者被一個或複數個R ^b取代的二苯胺基； R ^b每次出現時獨立地為D(氘)、氟、CN、C ₁~C ₁₂烷基、C ₁~C ₁₂烷氧基、C ₃~C ₁₀環烷基、C ₆~C ₁₄芳基、被一個或複數個R ^c取代的C ₆~C ₁₄芳基、5-至18-元雜芳基、被一個或複數個R ^c取代的5-至18-元雜芳基、二苯胺基、或者被一個或複數個R ^c取代的二苯胺基； R ^c每次出現時獨立地為D(氘)、氟、CN、C ₁~C ₁₂烷基、C ₁~C ₁₂烷氧基、C ₃~C ₁₀環烷基、C ₆~C ₁₄芳基、被一個或複數個R ^d取代的C ₆~C ₁₄芳基、5-至18-元雜芳基、被一個或複數個R ^d取代的5-至18-元雜芳基、二苯胺基、或者被一個或複數個R ^d取代的二苯胺基； R ^d每次出現時獨立地為D(氘)、氟、C ₁~C ₁₂烷基、C ₁~C ₁₂烷氧基、C ₃~C ₁₀環烷基、C ₆~C ₁₄芳基或者被一個或複數個R ^e取代的C ₆~C ₁₄芳基； R ^e每次出現時獨立地為D(氘)、氟、C ₁~C ₁₂烷基、C ₁~C ₁₂烷氧基、C ₃~C ₁₀環烷基、或者C ₆~C ₁₄芳基； 上述烷基、烷氧基、環烷基、芳基、雜芳基任選被一個或複數個選自以下的取代基所取代：鹵素、-CN、C ₁~C ₁₂烷基、C ₁~C ₁₂烷氧基、C ₁~C ₁₂鹵代烷基、C ₂~C ₆烯基、C ₃~C ₁₀環烷基、C ₆~C ₁₄芳基、或者5-至18-元雜芳基。 The present invention 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 , Diphenylamine group, or diphenylamine group substituted by one or more R ^a ; E is a single bond or

; R ¹¹ and R ²² are independently H, D (deuterium), C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy at each occurrence; R is:

, H, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₆ -C ₁₄ aryl, C ₆ -C substituted by one or more R ^d ₁₄ -aryl, 5- to 18-membered heteroaryl, or 5- to 18-membered heteroaryl substituted with one or more R ^d ; R ⁴ , R ⁵ and R ⁶ are each 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, by one or more R ^d Substituted C ₆ ~C ₁₄ aryl, 5- to 18-membered heteroaryl or 5- to 18-membered heteroaryl substituted by one or more R ^; R 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, substituted by one or more R ^b C ₆ ~C ₁₄ aryl, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R ^b , diphenylamino, or substituted by one or more R ^b The diphenylamino group; 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, 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 Aryl, diphenylamino, or diphenylamino substituted by one or more R ^c ; each occurrence of 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, C ₆ -C ₁₄ aryl substituted by one or more R ^d , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl, diphenylamino, or diphenylamino substituted with one or more R ^{d ;} each occurrence of 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 substituted by one or more R ^e ₁₄ Aryl; each occurrence of ^Re 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; The above-mentioned alkyl, alkoxy, cycloalkyl, aryl, and heteroaryl are optionally substituted by one or more substituents selected from the following groups: halogen, -CN, C ₁ ~C ₁₂ alkane base, 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.

In a certain embodiment of the invention, 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.

^In a certain embodiment of the invention, 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 ~ C ₁₂ alkyl, C ₁ -C ₁₂ fluoroalkyl, C ₁ -C ₁₂ alkoxy, phenyl and phenyl substituted by one or more R ^e selected from ^C ₁ -C ₆ Alkyl, C ₁ -C ₆ fluoroalkyl and C ₁ -C ₆ alkoxy.

^In a certain embodiment of the invention, each occurrence of R11 and ^R22 is independently H, methyl, methoxy or _CF3 .

In one embodiment of the present invention, the frontier molecular orbitals of the boron-nitrogen compounds of formulae 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. HOMO is distributed on the two Ns, and LUMO is distributed on the B atom, ring m2 and ring ph2.

In a certain embodiment of the present invention, 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 spectrum is less than or equal to 60 nm.

；R ⁴及R ⁶相同且為叔丁基、苯基、4-甲苯基、3-甲苯基、3,5-二甲苯基、4-叔丁基苯基、3-叔丁基苯基、3,5-二叔丁基苯基、4-C ₁~C ₁₀烷氧基苯基、3-C ₁~C ₁₀烷氧基苯基、或者3,5-二C ₁~C ₁₀烷氧基苯基；R ⁵為H。 In a certain embodiment of the present invention, 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 spectra is less than or equal to 60 nm. In a certain embodiment of the invention, 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 ₁ ~C ₁₀ alkoxyphenyl, or 3,5-diC ₁ ~C ₁₀ alkoxy phenyl; R ⁵ is H.

； 其中式II中的

為

或

。 In a certain embodiment of the present invention, the molecular structure composition of the compounds represented by formula I and II satisfies the following definitions: wherein E in formula I is a single bond or

; wherein in formula II

for

or

.

為如下基團的任一種：

B-1                                   B-2                             B-3                               B-4

B-5                             B-6                                  B-7                            B-8

B-9                              B-10                              B-11                        B-12

B-13                        B-14                             B-15                           B-16

B-17                       B-18                           B-19                             B-20

B-21                             B-22                              B-23                         B-24

B-25                         B-26                            B-27                             B-28

B-29                          B-30                             B-31                           B-32

B-33                            B-34                             B-35                        B-36

B-37                        B-38                             B-39                            B-40

B-41                         B-42                             B-43                          B-44

B-45                             B-46                            B-47                         B-48

B-49                           B-50                            B-51                           B-52

B-53                            B-54                              B-55                       B-56

B-57                        B-58                            B-59                             B-60

B-61                         B-62                            B-63                           B-64

B-65                          B-66                          B-67                          B-68

B-69                           B-70                           B-71                        B-72

B-73                         B-74                              B-75                         B-76

B-77                             B-78                           B-79                           B-80

B-81                            B-82                          B-83                           B-84

B-85                            B-86                           B-87                        B-88

B-89                       B-90                             B-91                           B-92

B-93                         B-94                             B-95                          B-96

B-97                           B-98                            B-99                      B-100        ； 其中式I及II中的

為如下基團的任一種：

。 wherein in formulas I and II

Any of the following groups:

B-1 B-2 B-3 B-4

B-5 B-6 B-7 B-8

B-9 B-10 B-11 B-12

B-13 B-14 B-15 B-16

B-17 B-18 B-19 B-20

B-21 B-22 B-23 B-24

B-25 B-26 B-27 B-28

B-29 B-30 B-31 B-32

B-33 B-34 B-35 B-36

B-37 B-38 B-39 B-40

B-41 B-42 B-43 B-44

B-45 B-46 B-47 B-48

B-49 B-50 B-51 B-52

B-53 B-54 B-55 B-56

B-57 B-58 B-59 B-60

B-61 B-62 B-63 B-64

B-65 B-66 B-67 B-68

B-69 B-70 B-71 B-72

B-73 B-74 B-75 B-76

B-77 B-78 B-79 B-80

B-81 B-82 B-83 B-84

B-85 B-86 B-87 B-88

B-89 B-90 B-91 B-92

B-93 B-94 B-95 B-96

B-97 B-98 B-99 B-100; wherein in formula I and II

Any of the following groups:

.

。 In a certain embodiment of the present invention, the compound represented by formula I and II is any one of the following compounds:

.

在反應式(1)中以含咔唑骨架的硼氮母核化合物為反應物，將其溶解在有機溶劑中，在催化劑的存在下加熱回流，b苯環的硼原子對位氫原子被活化並被硼酯取代； 在反應式(2)中利用Suzuki反應將吸電子基團引入到硼氮骨架上，被引入的吸電子基團位於硼氮骨架中b苯環的B原子的對位； 在反應式(2)中，ArX為如下三種分子中的任一種：

、

、

； X為Br或Cl； R ¹、R ⁴、R ⁵、R ⁶、R ¹¹、R ²²、R的定義如前所述。 The present invention 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):

In the reaction formula (1), 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 is substituted by boron ester; In the reaction formula (2), 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; In the reaction formula (2), 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.

其中

。 The compound of formula I described in the present invention 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 invention provides a kind of preparation method of the compound shown as formula (I and II, it can comprise following scheme:

in

.

The present invention also provides an organic electroluminescent device comprising an anode, a light-emitting layer, an optional hole injection layer, an optional hole transport layer, an optional electron transport layer, an optional electron injection layer, and a cathode, 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 device of the present invention may also include an optional hole blocking layer, an optional electron blocking layer, an optional capping layer, and the like. In one embodiment, the organic electroluminescent device has the structure shown in FIG. 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 transport layer layer, 6 is the electron injection layer, and 7 is the metal cathode.

In a certain embodiment of the present invention, the boron nitride compound represented by formula I or II is used to prepare a light-emitting layer in an organic electroluminescent device.

； 其中式II中的

為

或

； 其中式I和II中的

為式B-1至B-100中的任一種； 其中式I和II中的

為式M-1至M-88中的任一種。 In a certain embodiment of the present invention, the boron-nitrogen 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: wherein E in formula I is a single bond or

; wherein in formula II

for

or

; wherein in formula I and II

is any one of formulas B-1 to B-100; wherein in formulas I and II

is any one of formulae M-1 to M-88.

In a certain embodiment of the present invention, the boron nitride compounds represented by the formulae BN-1 to BN-584 are used to prepare the light-emitting layer in the organic electroluminescent device.

In a certain embodiment of the present invention, 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 boron nitride compound may further comprise any one or a combination 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 invention provides an organic electroluminescent composition comprising a boron nitride compound (as a dopant material) represented by formula I or II and a host material; the host material has electron and/or hole transport ability and is The triplet excited state energy is higher than or close to the triplet excited state energy of the doped material.

其中X ₁、Y ₁及Z ₁為CH或N，並且X ₁、Y ₁及Z ₁中至多有一個為N。 In a certain embodiment of the present invention, the host material in the organic electroluminescent composition can be a carbazole derivative and/or a carboline represented by formulae (H-1) to (H-6) derivative. In the organic electroluminescent composition, it is desirable to contain 0.3-30.0wt% (weight percentage) of any compound represented by formula I or II as a doping material, and the remaining 99.7-70.0wt% components are formula (H -1) A host material composed of 1 or 2 kinds of compounds in (H-6). In one embodiment, the host material contains two compounds of formulae (H-1) to (H-6) in a weight ratio of 1:5 to 5:1.

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.

其中X ₂、Y ₂及Z ₂為CH或N，並且X ₂、Y ₂及Z ₂中至多有一個為N。 wherein R ^1H and R ^2H are independently any of the following:

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 ₆ -C ₂₀ substituted with C ₁ -C ₂₀ alkyl Aryl or C ₆ -C ₂₀ aryl substituted by C ₁ -C ₂₀ alkoxy.

。 In a certain embodiment of the present invention, 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 in compounds H1-1 to H1-427. In an ideal embodiment of the present invention, 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 .

.

In a certain embodiment of the present invention, the doping material in the organic electroluminescent composition is any compound represented by formula I or II (content is 0.3wt% to 30.0wt%); host material (content 99.7wt-70.0wt%) is composed of any one of the 1,3,5-triazine derivatives represented by formulas Trz1-A, Trz2-A and Trz3-A and compounds represented by formulas H-1 to H-6 any of the compositions. In an ideal embodiment, 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.

。 One or two of R ^1a , R ^1b , R ^2a , R ^2b , R ^3a and R ^3b are independently R ^Tz , and the rest are identically or differently 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 groups Tz-n (n=1-61) shown in the following formula:

.

。 In a certain embodiment of the present invention, the doping material in the organic electroluminescent composition is any compound represented by formula I or II (content is 0.3wt% to 30.0wt%); host material (content 99.7wt% to 70.0wt%) derived from 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 composition. In an ideal embodiment, 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 invention provides an application of the above organic electroluminescent composition as an organic electroluminescent material.

In a certain embodiment of the present invention, the organic electroluminescent composition is used to prepare a light-emitting layer in an organic electroluminescent device.

The present invention also provides an organic electroluminescent device comprising an anode, a light-emitting layer, an optional hole injection layer, an optional hole transport layer, an optional electron transport layer, an optional electron injection layer, and a cathode, 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 includes the organic electroluminescence composition as described above. In a desirable embodiment, the light-emitting layer of the organic electroluminescent device comprises an organic electroluminescent composition as described above.

In a certain embodiment of the present invention, 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.

In a certain embodiment of the present invention, 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. In an ideal embodiment, 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 % of the components are from formula (H-1) to The main body composed of 1 or 2 kinds of 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.

In a certain embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the host material in the composition is one or two kinds of compounds H1-1 to H1-427. In an ideal embodiment, 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 % of the components are compounds H1-1 to H1 -1 or 2 compounds in 427. For example, when two kinds of compounds of formula H1-1 to H1-427 are contained in the composition, the weight ratio of the two compounds is 1:5 to 5:1.

In a certain embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any compound represented by formula I or II (content 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 formulas H-1 to H-6. For example, in the host material, 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.

In a certain embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer; the doping material in the organic electroluminescent composition is any compound represented by formula I or II (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 formula TRZ-1 to TRZ-56 and formula H1- 1 to any one of the carbazole or carboline derivatives represented by H1-427. For example, in the host material, the weight ratio between the 1,3,5-triazine derivative and the carbazole or carboline derivative is 1:5 to 5:1.

In a certain embodiment of the present invention, 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 main material (content is 99.7wt-70.0wt%) is any one of 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. For example, in the host material, the weight ratio between the 1,3,5-triazine derivative and the carbazole or carboline derivative is 1:5 to 5:1.

In one embodiment of the present invention, 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 also include any one or more 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 combination.

The present invention provides an application of the organic electroluminescence device in an organic electroluminescence display or an organic electroluminescence illumination light source.

The present invention provides a molecular structure design method for designing and synthesizing organic light-emitting materials. Based on the molecular design method, the existing green and red organic electroluminescent materials can effectively overcome the problem that the emission spectrum is too wide, and provide an organic molecule design and synthesis that emits light in the green-red region or even near-infrared and has narrow-spectrum emission characteristics. Preparation technology and method; and further provide an organic compound, composition and application in the field of organic electroluminescence that emits light in the green light to red light region and has narrow-spectrum light emission characteristics as shown in formula I and II. The organic molecules provided by the present invention and their compositions with some materials can be used as light-emitting materials to prepare the light-emitting layer of the organic electroluminescent device. 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 invention provides a synthesis method based on 1,3-dicarbazole (or its derivative) benzene tricoordinate B complex coupled with pyrimidine derivatives, the advantage of the synthesis method is that pyrimidines with electron withdrawing properties can be synthesized The derivative group is coupled with the C atom occupied by the LUMO orbital in the tricoordinate B resonance framework, so the pyrimidine derivative group with a conjugated structure and strong electron withdrawing properties can be effectively synthesized based on this synthesis method. Introduced into the three-coordinate B resonance framework.

R ¹及Ar的定義如前所述。 According to conventional synthetic ideas, those with ordinary knowledge in the art usually follow the following reaction route (3) to synthesize a molecule containing a tricoordinate B resonance skeleton and a pyrimidine derivative group, where Ar is a pyrimidine derivative in the following reaction formula , our experimental results show that the tricoordinate B structure cannot be formed according to the following reaction route, that is, the boron atom cannot achieve coordination with 1,3-dicarbazole (or its derivative) benzene under this condition. The target product could not be obtained in this reaction mode. The main reason is that when the pyrimidine derivative with strong electron withdrawing group exists, its para carbon atom is in an electron-deficient state, that is, the electron cloud density is low, so that the carbon atom cannot form a covalent bond with the boron atom.

The definitions of R ¹ and Ar are as described above.

The technical means of the embodiments of the present invention will be clearly and completely described below with reference to the drawings. Obviously, the described embodiments are some, but not all, embodiments of the present invention. Based on the described embodiments of the present invention, all other embodiments obtained by those with ordinary knowledge in the technical field without creative efforts shall fall within the protection scope of the present invention.

The present invention is further described below by way of examples, but the present invention is not limited to the scope of the described examples. In the following examples, the experimental methods without specific conditions are selected according to conventional methods and conditions, or according to the product description.

Molecular mass spectrometry data (Mass Spectra: MS) with relative molecular weight below 1000 was measured by ITQ1100 ion trap gas chromatography-mass spectrometer of Thermo Fisher Company, and molecular mass spectrometry data of molecular weight with relative molecular weight above 1000 was obtained by Autoflex Speed of Bruker Company Measured by matrix-assisted group laser-resolved time-of-flight mass spectrometry. The machine used for elemental analysis of the final product was a Flash EA1112 from Elemental analysis company.

The UV-Vis absorption spectrum of the sample film was measured by a LAMBDA 35 UV-Vis spectrophotometer from PerkinElmer. The fluorescence spectrum was measured by the RF-5301PC fluorometer of Shimadzu Corporation of Japan, and the excitation wavelength selected during the test was the maximum absorption wavelength.

具體採用的原料-2包含以下分子：

。 具體採用的原料-3包含以下分子：

。 Specifically, the raw material-1 used contains the following molecules:

Specifically, the raw material-2 used contains the following molecules:

. Specifically, the raw material-3 used contains the following molecules:

.

其中

。 ［實施例］ The basic process route of compound synthesis involved in the present invention 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. We used the originally synthesized boron-nitrogen core containing carbazole skeleton as the substrate, dissolved it in tetrahydrofuran, and added 1% equivalent of the main catalyst methoxy (cyclooctadiene) iridium dimer, 2% equivalent Under the condition of co-catalyst 4,4'-di-tert-butyl-2,2'-bipyridine, the reaction system is heated to reflux, and the boron atom replaces the para-hydrogen atom of the benzene ring to activate and is replaced by boron ester. Next, a simple Suzuki reaction can flexibly obtain a variety of electron-withdrawing substituted compounds. The specific synthesis process steps are:

in

. [Example]

Synthesis Example In the first step, 60 ml of anhydrous DMF (N, N-dimethylformamide) solution containing 35.2 mmol of carbazole derivatives was slowly added dropwise to 50 ml of potassium tert-butoxide (48.0 mmol) containing 5.4 g 20 ml of anhydrous DMF solution containing 3.1 g of 2-bromo-1,3-difluorobenzene (16.0 mmol) was added dropwise thereto after stirring at room temperature for 2 hours. The reaction system was stirred at 140°C for 24 hours, then cooled to room temperature and poured into ice water. The white solid was filtered off with suction, dried in vacuo, and further purified by column chromatography using a mixed eluent of dichloromethane/petroleum ether to give the intermediate BrNCz as a white solid. In the second step, under the protection of nitrogen atmosphere, 19.4 mL of n-hexane solution of tert-butyllithium (25.2 mmol) was slowly added to 100 mL of tert-butylbenzene solution (-30 °C) containing 12.6 mmol of intermediate BrNCz. The temperature was slowly raised to 60°C, and after stirring for 2 hours, n-hexane was removed in vacuo, then cooled to -30°C, 2.4 mL of boron tribromide (6.3 mmol) was added, and the reaction mixture was stirred at room temperature for 1 hour. Next, 15.6 mL of N,N-diisopropylethylamine (91.1 mmol) was added at 0°C, and the reaction mixture was heated to 130°C and stirred for 5 hours, and then cooled to room temperature. 5 ml of methanol was added to the reaction mixture to quench residual _BBr3 . The reaction was concentrated in vacuo and purified by column chromatography eluting with a mixture of dichloromethane/petroleum ether to give the BNCz parent nucleus. In the third step, the carbazole skeleton-containing boron nitrogen raw material (6.5 mmol) and 1.7 g of pinacol biboronate (6.5 mmol) were added to tetrahydrofuran (60 mL) at room temperature, 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). 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. In the fourth step, Ar-X (Ar was defined as before, X is bromine) (0.6 mmol), BN-Bpin (0.5 mmol), 0.14 g potassium carbonate (1 mmol) and water (2 mL) were added to tetrahydrofuran (16 mL), the mixture was sparged with nitrogen for 10 minutes and 28.9 mg of tetrakis(triphenylphosphine)palladium (0.025 mmol) was added under high flow of nitrogen. The mixture was heated to reflux and stirred for 12 hours. After the reaction system was cooled to room temperature, the reaction mixture was extracted with dichloromethane and water, the organic phase was heated and spin-dried under vacuum, and then purified by column chromatography to obtain the target product BN-n (n=1-584).

Taking compound BN-66 as an example to illustrate the specific details of the synthesis example experiment: In the first step, 60 ml of anhydrous DMF (N, N-dimethylcarbazole) containing 9.8 g of 3,6-di-tert-butylcarbazole (35.2 mmol) Formamide) solution was slowly added dropwise to 50 ml of anhydrous DMF solution containing 5.4 g potassium tert-butoxide (48.0 mmol), and after stirring at room temperature for 2 hours, 20 ml containing 3.1 g of 2-bromo was added dropwise. -1,3-Difluorobenzene (16.0 mmol) in dry DMF. The reaction system was stirred at 140°C for 24 hours, then cooled to room temperature and poured into ice water. The white solid was filtered off with suction, dried in vacuo, and further purified by column chromatography using a mixed eluent of dichloromethane/petroleum ether to give 10.5 g of intermediate BrNCz as a white solid (92% yield). In the second step, under the protection of nitrogen atmosphere, 19.4 mL of n-hexane solution of tert-butyllithium (25.2 mmol) was slowly added to 100 mL of tert-butylbenzene solution containing 9.0 g (12.6 mmol) of intermediate BrNCz (-30 °C). ). The temperature was slowly raised to 60°C, and after stirring for 2 hours, n-hexane was removed in vacuo, then cooled to -30°C, 2.4 mL of boron tribromide (6.3 mmol) was added, and the reaction mixture was stirred at room temperature for 1 hour. Next, 15.6 mL of N,N-diisopropylethylamine (91.1 mmol) was added at 0°C, and the reaction mixture was heated to 130°C and stirred for 5 hours, then cooled to room temperature. 5 ml of methanol was added to the reaction mixture to quench residual _BBr3 . The reaction system was concentrated in vacuo and purified by column chromatography with a mixture of dichloromethane/petroleum ether as eluent to obtain 2.9 g of BNCz parent nucleus as a yellow solid (yield 35%) (the experiment can be repeated many times to enrich collection of raw materials). In the third step, 4.2 g of BNCz (6.5 mmol), 1.7 g of pinacol diboronate (6.5 mmol) were added to tetrahydrofuran (60 mL) at room temperature, the mixture was sparged with nitrogen for 10 min, and the mixture was heated on high 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 nitrogen flow. 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 4.5 g BN-Bpin (yield 90%). In the fourth step, 187 mg of 2-bromo-4,6-diphenylpyrimidine (0.6 mmol), 383 mg of BN-Bpin (0.5 mmol), 0.14 g of potassium carbonate (1 mmol) and water (2 mL) were added to In tetrahydrofuran (16 mL), the mixture was sparged with nitrogen for 10 minutes, and 28.9 mg of tetrakis(triphenylphosphine)palladium (0.025 mmol) was added under high flow of nitrogen. The mixture was heated to reflux and stirred for 12 hours. After the reaction system was cooled to room temperature, the reaction mixture was extracted with dichloromethane and water, the organic phase was heated and spin-dried under vacuum, and then purified by column chromatography to obtain 284 mg of the target product BN-66 as a yellow solid (yield). 58%).

[Table 1] Elemental analysis of compounds BN-1 to BN-584 (percentage content of C, H and N in the compounds), molecular weight measured by mass spectrometry and data of synthesis reaction yield (total yield of four-step reaction). compound raw material -1 raw material -2 Raw material -3 molecular weight Elemental Analysis (%) ( C , H , N ) Yield (%) BN-1 S1 S2-1 S3-1 494.36 C, 82.61; H, 3.87; N, 11.33 17 BN-2 S1 S2-1 S3-2 646.56 C, 85.45; H, 4.21; N, 8.67 18 BN-3 S1 S2-1 S3-3 758.78 C, 85.48; H, 5.71; N, 7.38 20 BN-4 S1 S2-1 S3-4 814.88 C, 85.49; H, 6.31; N, 6.88 twenty one BN-5 S1 S2-1 S3-5 702.67 C, 85.47; H, 5.02; N, 7.97 20 BN-6 S1 S2-1 S3-6 702.67 C, 85.47; H, 5.02; N, 7.97 17 BN-7 S1 S2-1 S3-7 870.99 C, 85.50; H, 6.83; N, 6.43 16 BN-8 S1 S2-1 S3-8 846.88 C, 82.26; H, 6.07; N, 6.62 twenty three BN-9 S1 S2-1 S3-9 730.72 C, 85.47; H, 5.38; N, 7.67 15 BN-10 S1 S2-1 S3-10 1151.53 C, 85.53; H, 8.67; N, 4.87 twenty two BN-11 S1 S2-1 S3-11 1247.53 C, 78.95; H, 8.00; N, 4.49 twenty one BN-12 S1 S2-1 S3-12 798.76 C, 87.22; H, 4.42; N, 7.01 20 BN-13 S1 S2-1 S3-13 910.97 C, 87.02; H, 5.64; N, 6.15 19 BN-14 S1 S2-1 S3-14 910.97 C, 87.02; H, 5.64; N, 6.15 17 BN-15 S1 S2-1 S3-15 950.95 C, 88.41; H, 4.56; N, 5.89 15 NN-16 S1 S2-1 S3-16 950.95 C, 88.41; H, 4.56; N, 5.89 twenty three BN-17 S1 S2-1 S3-17 722.66 C, 86.43; H, 4.32; N, 7.75 twenty one BN-18 S1 S2-1 S3-18 834.87 C, 86.32; H, 5.67; N, 6.71 25 BN-19 S1 S2-1 S3-19 834.87 C, 86.32; H, 5.67; N, 6.71 twenty one BN-20 S1 S2-1 S3-20 890.98 C, 86.28; H, 6.22; N, 6.29 20 BN-21 S1 S2-1 S3-21 778.77 C, 86.37; H, 5.05; N, 7.19 15 BN-22 S1 S2-1 S3-22 778.77 C, 86.37; H, 5.05; N, 7.19 twenty two BN-23 S1 S2-1 S3-23 947.09 C, 86.24; H, 6.71; N, 5.92 twenty one BN-24 S1 S2-1 S3-24 922.98 C, 83.29; H, 6.01; N, 6.07 20 BN-25 S1 S2-1 S3-25 806.82 C, 86.34; H, 5.37; N, 6.94 20 BN-26 S1 S2-1 S3-26 1227.63 C, 86.10; H, 8.46; N, 4.56 twenty one BN-27 S1 S2-1 S3-27 1323.62 C, 79.85; H, 7.84; N, 4.23 20 BN-28 S1 S2-1 S3-28 874.85 C, 87.87; H, 4.49; N, 6.40 17 BN-29 S1 S2-1 S3-29 987.07 C, 87.61; H, 5.62; N, 5.68 16 BN-30 S1 S2-1 S3-30 989.07 C, 86.22; H, 5.61; N, 7.08 twenty three BN-31 S1 S2-1 S3-31 1027.05 C, 88.88; H, 4.61; N, 5.46 15 BN-32 S1 S2-1 S3-32 1027.05 C, 88.88; H, 4.61; N, 5.46 20 BN-33 S1 S2-2 S3-1 550.47 C, 82.91; H, 4.94; N, 10.18 twenty one BN-34 S1 S2-2 S3-2 702.67 C, 85.47; H, 5.02; N, 7.97 20 BN-35 S1 S2-2 S3-3 814.88 C, 85.49; H, 6.31; N, 6.88 20 BN-36 S1 S2-2 S3-4 870.99 C, 85.50; H, 6.83; N, 6.43 twenty one BN-37 S1 S2-2 S3-5 758.78 C, 85.48; H, 5.71; N, 7.38 20 BN-38 S1 S2-2 S3-6 758.78 C, 85.48; H, 5.71; N, 7.38 twenty one BN-39 S1 S2-2 S3-7 927.10 C, 85.51; H, 7.28; N, 6.04 20 BN-40 S1 S2-2 S3-8 902.99 C, 82.47; H, 6.59; N, 6.20 17 BN-41 S1 S2-2 S3-9 786.83 C, 85.48; H, 6.02; N, 7.12 16 BN-42 S1 S2-2 S3-10 1207.64 C, 85.53; H, 8.93; N, 4.64 20 BN-43 S1 S2-2 S3-11 1303.63 C, 79.24; H, 8.27; N, 4.30 19 BN-44 S1 S2-2 S3-12 854.86 C, 87.11; H, 5.07; N, 6.55 17 BN-45 S1 S2-2 S3-13 967.08 C, 86.94; H, 6.15; N, 5.79 15 BN-46 S1 S2-2 S3-14 967.08 C, 86.94; H, 6.15; N, 5.79 twenty three BN-47 S1 S2-2 S3-15 1007.06 C, 88.26; H, 5.10; N, 5.56 twenty one BN-48 S1 S2-2 S3-16 1007.06 C, 88.26; H, 5.10; N, 5.56 15 BN-49 S1 S2-2 S3-17 778.77 C, 86.37; H, 5.05; N, 7.19 twenty three BN-50 S1 S2-2 S3-18 890.98 C, 86.28; H, 6.22; N, 6.29 twenty one BN-51 S1 S2-2 S3-19 890.98 C, 86.28; H, 6.22; N, 6.29 25 BN-52 S1 S2-2 S3-20 947.09 C, 86.24; H, 6.71; N, 5.92 twenty one BN-53 S1 S2-2 S3-21 834.87 C, 86.32; H, 5.67; N, 6.71 15 BN-54 S1 S2-2 S3-22 834.87 C, 86.32; H, 5.67; N, 6.71 20 BN-55 S1 S2-2 S3-23 1003.20 C, 86.20; H, 7.13; N, 5.58 twenty one BN-56 S1 S2-2 S3-24 979.09 C, 83.42; H, 6.49; N, 5.72 20 BN-57 S1 S2-2 S3-25 862.93 C, 86.30; H, 5.96; N, 6.49 20 BN-58 S1 S2-2 S3-26 1283.74 C, 86.08; H, 8.72; N, 4.36 twenty one BN-59 S1 S2-2 S3-27 1379.73 C, 80.09; H, 8.11; N, 4.06 20 BN-60 S1 S2-2 S3-28 930.96 C, 87.73; H, 5.09; N, 6.02 20 BN-61 S1 S2-2 S3-29 1043.18 C, 87.51; H, 6.09; N, 5.37 17 BN-62 S1 S2-2 S3-30 1043.18 C, 87.51; H, 6.09; N, 5.37 16 BN-63 S1 S2-2 S3-31 1083.16 C, 88.71; H, 5.12; N, 5.17 twenty three BN-64 S1 S2-2 S3-32 1083.16 C, 88.71; H, 5.12; N, 5.17 15 BN-65 S1 S2-3 S3-1 718.80 C, 83.55; H, 7.15; N, 7.79 twenty two BN-66 S1 S2-3 S3-2 870.99 C, 85.50; H, 6.83; N, 6.43 16 BN-67 S1 S2-3 S3-3 983.21 C, 85.51; H, 7.69; N, 5.70 20 BN-68 S1 S2-3 S3-4 1039.32 C, 85.52; H, 8.05; N, 5.39 19 BN-69 S1 S2-3 S3-5 927.10 C, 85.51; H, 7.28; N, 6.04 17 BN-70 S1 S2-3 S3-6 927.10 C, 85.51; H, 7.28; N, 6.04 15 BN-71 S1 S2-3 S3-7 1053.34 C, 85.52; H, 8.13; N, 5.32 twenty three BN-72 S1 S2-3 S3-8 1071.31 C, 82.96; H, 7.81; N, 5.23 twenty one BN-73 S1 S2-3 S3-9 955.15 C, 85.51; H, 7.49; N, 5.87 25 BN-74 S1 S2-3 S3-10 1375.96 C, 85.55; H, 9.60; N, 4.07 twenty one BN-75 S1 S2-3 S3-11 1471.96 C, 79.97; H, 8.97; N, 3.81 20 BN-76 S1 S2-3 S3-12 1023.19 C, 86.87; H, 6.60; N, 5.48 15 BN-77 S1 S2-3 S3-13 1135.40 C, 86.74; H, 7.37; N, 4.93 twenty two BN-78 S1 S2-3 S3-14 1135.40 C, 86.74; H, 7.37; N, 4.93 twenty one BN-79 S1 S2-3 S3-15 1175.38 C, 87.88; H, 6.43; N, 4.77 20 BN-80 S1 S2-3 S3-16 1175.38 C, 87.88; H, 6.43; N, 4.77 20 BN-81 S1 S2-3 S3-17 947.09 C, 86.24; H, 6.71; N, 5.92 twenty one BN-82 S1 S2-3 S3-18 1059.31 C, 86.17; H, 7.52; N, 5.29 20 BN-83 S1 S2-3 S3-19 1059.31 C, 86.17; H, 7.52; N, 5.29 17 BN-84 S1 S2-3 S3-20 1115.41 C, 86.15; H, 7.86; N, 5.02 16 BN-85 S1 S2-3 S3-21 1003.20 C, 86.20; H, 7.13; N, 5.58 twenty three BN-86 S1 S2-3 S3-22 1003.20 C, 86.20; H, 7.13; N, 5.58 15 BN-87 S1 S2-3 S3-23 1171.52 C, 86.12; H, 8.17; N, 4.78 20 BN-88 S1 S2-3 S3-24 1147.41 C, 83.74; H, 7.64; N, 4.88 twenty one BN-89 S1 S2-3 S3-25 1031.25 C, 86.19; H, 7.33; N, 5.43 20 BN-90 S1 S2-3 S3-26 1452.06 C, 86.03; H, 9.37; N, 3.86 20 BN-91 S1 S2-3 S3-27 1548.06 C, 80.69; H, 8.79; N, 3.62 twenty one BN-92 S1 S2-3 S3-28 1099.29 C, 87.41; H, 6.51; N, 5.10 20 BN-93 S1 S2-3 S3-29 1211.50 C, 87.24; H, 7.24; N, 4.62 twenty one BN-94 S1 S2-3 S3-30 1211.50 C, 87.24; H, 7.24; N, 4.62 20 BN-95 S1 S2-3 S3-31 1251.48 C, 88.30; H, 6.36; N, 4.48 17 BN-96 S1 S2-3 S3-32 1251.48 C, 88.30; H, 6.36; N, 4.48 16 BN-97 S1 S2-4 S3-1 798.76 C, 87.22; H, 4.42; N, 7.01 20 BN-98 S1 S2-4 S3-2 950.95 C, 88.41; H, 4.56; N, 5.89 19 BN-99 S1 S2-4 S3-3 1001.10 C, 87.58; H, 5.74; N, 5.60 17 BN-100 S1 S2-4 S3-4 1119.28 C, 87.99; H, 6.03; N, 5.01 15 BN-101 S1 S2-4 S3-5 1007.06 C, 88.26; H, 5.10; N, 5.56 twenty three BN-102 S1 S2-4 S3-6 1007.06 C, 88.26; H, 5.10; N, 5.56 twenty one BN-103 S1 S2-4 S3-7 1175.38 C, 87.88; H, 6.43; N, 4.77 15 BN-104 S1 S2-4 S3-8 1151.27 C, 85.55; H, 5.87; N, 4.87 twenty three BN-105 S1 S2-4 S3-9 1035.11 C, 88.19; H, 5.36; N, 5.41 twenty one NN-106 S1 S2-4 S3-10 1455.92 C, 87.45; H, 7.96; N, 3.85 25 BN-107 S1 S2-4 S3-11 1551.92 C, 82.04; H, 7.47; N, 3.61 15 BN-108 S1 S2-4 S3-12 1103.15 C, 89.28; H, 4.66; N, 5.08 20 BN-109 S1 S2-4 S3-13 1215.36 C, 88.94; H, 5.56; N, 4.61 twenty one BN-110 S1 S2-4 S3-14 1215.36 C, 88.94; H, 5.56; N, 4.61 20 BN-111 S1 S2-4 S3-15 1255.34 C, 89.94; H, 4.74; N, 4.46 20 BN-112 S1 S2-4 S3-16 1255.34 C, 89.94; H, 4.74; N, 4.46 twenty one BN-113 S1 S2-4 S3-17 1027.05 C, 88.88; H, 4.61; N, 5.46 20 BN-114 S1 S2-4 S3-18 1139.27 C, 88.56; H, 5.57; N, 4.92 twenty one BN-115 S1 S2-4 S3-19 1139.27 C, 88.56; H, 5.57; N, 4.92 20 BN-116 S1 S2-4 S3-20 1195.37 C, 88.42; H, 5.99; N, 4.69 17 BN-117 S1 S2-4 S3-21 1083.16 C, 88.71; H, 5.12; N, 5.17 16 BN-118 S1 S2-4 S3-22 1083.16 C, 88.71; H, 5.12; N, 5.17 20 BN-119 S1 S2-4 S3-23 1251.48 C, 88.30; H, 6.36; N, 4.48 19 BN-120 S1 S2-4 S3-24 1227.37 C, 86.12; H, 5.83; N, 4.56 17 BN-121 S1 S2-4 S3-25 1111.21 C, 88.63; H, 5.35; N, 5.04 15 BN-122 S1 S2-4 S3-26 1532.02 C, 87.81; H, 7.83; N, 3.66 twenty three BN-123 S1 S2-4 S3-27 1628.02 C, 82.63; H, 7.37; N, 3.44 twenty one BN-124 S1 S2-4 S3-28 1179.25 C, 89.63; H, 4.70; N, 4.75 twenty two BN-125 S1 S2-4 S3-29 1291.46 C, 89.28; H, 5.54; N, 4.34 twenty one BN-126 S1 S2-4 S3-30 1291.46 C, 89.28; H, 5.54; N, 4.34 20 BN-127 S1 S2-4 S3-31 1331.44 C, 90.21; H, 4.77; N, 4.21 20 BN-128 S1 S2-4 S3-32 1331.44 C, 90.21; H, 4.77; N, 4.21 twenty one BN-129 S1 S2-5 S3-1 1155.14 C, 85.26; H, 4.10; N, 9.70 20 BN-130 S1 S2-5 S3-2 1307.34 C, 86.36; H, 4.24; N, 8.57 17 BN-131 S1 S2-5 S3-3 1419.56 C, 86.30; H, 5.04; N, 7.89 16 BN-132 S1 S2-5 S3-4 1475.66 C, 86.28; H, 5.40; N, 7.59 twenty three BN-133 S1 S2-5 S3-5 1363.45 C, 86.33; H, 4.66; N, 8.22 15 BN-134 S1 S2-5 S3-6 1363.45 C, 86.33; H, 4.66; N, 8.22 20 BN-135 S1 S2-5 S3-7 1531.77 C, 86.25; H, 5.73; N, 7.32 twenty one BN-136 S1 S2-5 S3-8 1507.66 C, 84.45; H, 5.28; N, 7.43 20 BN-137 S1 S2-5 S3-9 1391.50 C, 86.32; H, 4.85; N, 8.05 20 BN-138 S1 S2-5 S3-10 1812.31 C, 86.16; H, 7.06; N, 6.18 twenty one BN-139 S1 S2-5 S3-11 1908.31 C, 81.82; H, 6.71; N, 5.87 20 BN-140 S1 S2-5 S3-12 1459.54 C, 87.23; H, 4.35; N, 7.68 twenty one BN-141 S1 S2-5 S3-13 1571.75 C, 87.12; H, 5.07; N, 7.13 20 BN-142 S1 S2-5 S3-14 1571.75 C, 87.12; H, 5.07; N, 7.13 17 BN-143 S1 S2-5 S3-15 1611.73 C, 87.94; H, 4.44; N, 6.95 16 BN-144 S1 S2-5 S3-16 1611.73 C, 87.94; H, 4.44; N, 6.95 20 BN-145 S1 S2-5 S3-17 1383.44 C, 86.82; H, 4.30; N, 8.10 19 BN-146 S1 S2-5 S3-18 1495.65 C, 86.73; H, 5.05; N, 7.49 17 BN-147 S1 S2-5 S3-19 1495.65 C, 86.73; H, 5.05; N, 7.49 15 BN-148 S1 S2-5 S3-20 1551.76 C, 86.69; H, 5.39; N, 7.22 twenty three BN-149 S1 S2-5 S3-21 1439.55 C, 86.77; H, 4.69; N, 7.78 twenty one BN-150 S1 S2-5 S3-22 1439.55 C, 86.77; H, 4.69; N, 7.78 15 BN-151 S1 S2-5 S3-23 1607.87 C, 86.65; H, 5.70; N, 6.97 twenty three BN-152 S1 S2-5 S3-24 1583.76 C, 84.94; H, 5.28; N, 7.08 twenty one BN-153 S1 S2-5 S3-25 1467.60 C, 86.75; H, 4.88; N, 7.64 twenty two BN-154 S1 S2-5 S3-26 1888.41 C, 86.50; H, 6.99; N, 5.93 20 BN-155 S1 S2-5 S3-27 1984.40 C, 82.32; H, 6.65; N, 5.65 20 BN-156 S1 S2-5 S3-28 1535.63 C, 87.60; H, 4.40; N, 7.30 twenty one BN-157 S1 S2-5 S3-29 1647.85 C, 87.47; H, 5.08; N, 6.80 20 BN-158 S1 S2-5 S3-30 1647.85 C, 87.47; H, 5.08; N, 6.80 twenty one BN-159 S1 S2-5 S3-31 1687.83 C, 88.24; H, 4.48; N, 6.64 20 BN-160 S1 S2-5 S3-32 1687.83 C, 88.24; H, 4.48; N, 6.64 17 BN-161 S1 S2-6 S3-1 1163.21 C, 84.67; H, 4.77; N, 9.63 twenty three BN-162 S1 S2-6 S3-2 1315.40 C, 85.83; H, 4.83; N, 8.52 twenty one BN-163 S1 S2-6 S3-3 1427.62 C, 85.82; H, 5.58; N, 7.85 twenty two BN-164 S1 S2-6 S3-4 1483.73 C, 85.81; H, 5.91; N, 7.55 20 BN-165 S1 S2-6 S3-5 1371.51 C, 85.82; H, 5.22; N, 8.17 20 BN-166 S1 S2-6 S3-6 1371.51 C, 85.82; H, 5.22; N, 8.17 twenty one BN-167 S1 S2-6 S3-7 1539.84 C, 85.80; H, 6.22; N, 7.28 20 BN-168 S1 S2-6 S3-8 1515.73 C, 84.00; H, 5.79; N, 7.39 twenty one BN-169 S1 S2-6 S3-9 1399.57 C, 85.82; H, 5.40; N, 8.01 20 BN-170 S1 S2-6 S3-10 1820.38 C, 85.78; H, 7.48; N, 6.16 twenty one BN-171 S1 S2-6 S3-11 1916.37 C, 81.48; H, 7.10; N, 5.85 20 BN-172 S1 S2-6 S3-12 1467.60 C, 86.75; H, 4.88; N, 7.64 20 BN-173 S1 S2-6 S3-13 1579.82 C, 86.67; H, 5.55; N, 7.09 twenty one BN-174 S1 S2-6 S3-14 1579.82 C, 86.67; H, 5.55; N, 7.09 20 BN-175 S1 S2-6 S3-15 1619.80 C, 87.50; H, 4.92; N, 6.92 17 BN-176 S1 S2-6 S3-16 1619.80 C, 87.50; H, 4.92; N, 6.92 16 BN-177 S1 S2-6 S3-17 1391.50 C, 86.32; H, 4.85; N, 8.05 twenty three BN-178 S1 S2-6 S3-18 1503.72 C, 86.27; H, 5.56; N, 7.45 15 BN-179 S1 S2-6 S3-19 1503.72 C, 86.27; H, 5.56; N, 7.45 20 BN-180 S1 S2-6 S3-20 1559.83 C, 86.24; H, 5.88; N, 7.18 twenty one BN-181 S1 S2-6 S3-21 1447.61 C, 86.29; H, 5.22; N, 7.74 20 BN-182 S1 S2-6 S3-22 1447.61 C, 86.29; H, 5.22; N, 7.74 20 BN-183 S1 S2-6 S3-23 1615.93 C, 86.22; H, 6.18; N, 6.93 twenty one BN-184 S1 S2-6 S3-24 1591.82 C, 84.51; H, 5.76; N, 7.04 20 BN-185 S1 S2-6 S3-25 1475.66 C, 86.28; H, 5.40; N, 7.59 twenty one BN-186 S1 S2-6 S3-26 1896.47 C, 86.13; H, 7.39; N, 5.91 20 BN-187 S1 S2-6 S3-27 1992.47 C, 81.98; H, 7.03; N, 5.62 17 BN-188 S1 S2-6 S3-28 1543.70 C, 87.14; H, 4.90; N, 7.26 16 BN-189 S1 S2-6 S3-29 1655.91 C, 87.04; H, 5.54; N, 6.77 20 BN-190 S1 S2-6 S3-30 1655.91 C, 87.04; H, 5.54; N, 6.77 19 BN-191 S1 S2-6 S3-31 1695.89 C, 87.82; H, 4.93; N, 6.61 17 BN-192 S1 S2-6 S3-32 1695.89 C, 87.82; H, 4.93; N, 6.61 15 BN-193 S1 S2-1 S3-33 872.97 C, 82.55; H, 6.58; N, 9.63 twenty three BN-194 S1 S2-1 S3-34 977.12 C, 83.59; H, 6.71; N, 8.60 twenty one BN-195 S1 S2-1 S3-35 1185.42 C, 85.11; H, 6.89; N, 7.09 15 BN-196 S1 S2-1 S3-36 952.93 C, 85.71; H, 4.34; N, 8.82 twenty three BN-197 S1 S2-1 S3-37 1009.04 C, 85.70; H, 4.89; N, 8.33 twenty one BN-198 S1 S2-1 S3-38 1009.04 C, 85.70; H, 4.89; N, 8.33 twenty two BN-199 S1 S2-1 S3-39 1177.36 C, 85.69; H, 6.25; N, 7.14 20 BN-200 S1 S2-1 S3-40 1177.36 C, 85.69; H, 6.25; N, 7.14 20 BN-201 S1 S2-1 S3-41 1177.36 C, 85.69; H, 6.25; N, 7.14 twenty one BN-202 S1 S2-1 S3-42 1289.58 C, 85.69; H, 6.96; N, 6.52 20 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, 7.50 20 BN-211 S1 S2-1 S3-51 1962.87 C, 85.67; H, 9.50; N, 4.28 twenty one BN-212 S1 S2-1 S3-52 2154.86 C, 78.03; H, 8.65; N, 3.90 20 BN-213 S1 S2-1 S3-53 1257.32 C, 87.89; H, 4.57; N, 6.68 twenty one BN-214 S1 S2-1 S3-54 1313.43 C, 87.79; H, 4.99; N, 6.40 20 BN-215 S1 S2-1 S3-55 1481.75 C, 87.54; H, 6.05; N, 5.67 16 BN-216 S1 S2-1 S3-56 1481.75 C, 87.54; H, 6.05; N, 5.67 20 BN-217 S1 S2-1 S3-57 1257.32 C, 87.89; H, 4.57; N, 6.68 19 BN-218 S1 S2-1 S3-58 1313.43 C, 87.79; H, 4.99; N, 6.40 17 BN-219 S1 S2-1 S3-59 1481.75 C, 87.54; H, 6.05; N, 5.67 15 BN-220 S1 S2-1 S3-60 1481.75 C, 87.54; H, 6.05; N, 5.67 twenty three BN-221 S1 S2-1 S3-61 1561.71 C, 89.21; H, 4.71; N, 5.38 twenty one BN-222 S1 S2-1 S3-62 1786.14 C, 88.76; H, 5.93; N, 4.71 twenty two BN-223 S1 S2-1 S3-63 1561.71 C, 89.21; H, 4.71; N, 5.38 twenty one BN-224 S1 S2-1 S3-64 2010.58 C, 88.41; H, 6.87; N, 4.18 20 BN-225 S1 S2-1 S3-65 682.68 C, 84.45; H, 5.76; N, 8.21 20 BN-226 S1 S2-1 S3-66 734.75 C, 85.00; H, 5.90; N, 7.63 twenty one BN-227 S1 S2-1 S3-67 838.91 C, 85.90; H, 6.13; N, 6.68 20 BN-228 S1 S2-1 S3-68 722.66 C, 86.43; H, 4.32; N, 7.75 17 BN-229 S1 S2-1 S3-69 750.71 C, 86.40; H, 4.70; N, 7.46 16 BN-230 S1 S2-1 S3-70 750.71 C, 86.40; H, 4.70; N, 7.46 twenty three BN-231 S1 S2-1 S3-71 834.87 C, 86.32; H, 5.67; N, 6.71 15 BN-232 S1 S2-1 S3-72 834.87 C, 86.32; H, 5.67; N, 6.71 20 BN-233 S1 S2-1 S3-73 834.87 C, 86.32; H, 5.67; N, 6.71 twenty one BN-234 S1 S2-1 S3-74 890.98 C, 86.28; H, 6.22; N, 6.29 20 BN-235 S1 S2-1 S3-75 947.09 C, 86.24; H, 6.71; N, 5.92 20 BN-236 S1 S2-1 S3-76 778.77 C, 86.37; H, 5.05; N, 7.19 twenty one BN-237 S1 S2-1 S3-77 778.77 C, 86.37; H, 5.05; N, 7.19 19 BN-238 S1 S2-1 S3-78 947.09 C, 86.24; H, 6.71; N, 5.92 17 BN-239 S1 S2-1 S3-79 947.09 C, 86.24; H, 6.71; N, 5.92 15 BN-240 S1 S2-1 S3-80 979.09 C, 83.42; H, 6.49; N, 5.72 twenty three BN-241 S1 S2-1 S3-81 922.98 C, 83.29; H, 6.01; N, 6.07 twenty one BN-242 S1 S2-1 S3-82 806.82 C, 86.34; H, 5.37; N, 6.94 twenty two BN-243 S1 S2-1 S3-83 1227.63 C, 86.10; H, 8.46; N, 4.56 twenty one BN-244 S1 S2-1 S3-84 1323.62 C, 79.85; H, 7.84; N, 4.23 20 BN-245 S1 S2-1 S3-85 874.85 C, 87.87; H, 4.49; N, 6.40 20 BN-246 S1 S2-1 S3-86 902.91 C, 87.80; H, 4.80; N, 6.21 twenty one BN-247 S1 S2-1 S3-87 987.07 C, 87.61; H, 5.62; N, 5.68 20 BN-248 S1 S2-1 S3-88 987.07 C, 87.61; H, 5.62; N, 5.68 17 BN-249 S1 S2-1 S3-89 874.85 C, 87.87; H, 4.49; N, 6.40 16 BN-250 S1 S2-1 S3-90 902.91 C, 87.80; H, 4.80; N, 6.21 twenty three BN-251 S1 S2-1 S3-90 987.07 C, 87.61; H, 5.62;; N, 5.68 15 BN-252 S1 S2-1 S3-92 987.07 C, 87.61; H, 5.62;; N, 5.68 20 BN-253 S1 S2-1 S3-93 1027.05 C, 88.88; H, 4.61; N, 5.46 twenty one BN-254 S1 S2-1 S3-94 1139.27 C, 88.56; H, 5.57; N, 4.92 20 BN-255 S1 S2-1 S3-95 1027.05 C, 88.88; H, 4.61; N, 5.46 20 BN-256 S1 S2-1 S3-96 1139.27 C, 88.56; H, 5.57; N, 4.92 twenty one BN-257 S1 S2-2 S3-33 929.08 C, 82.74; H, 7.05; N, 9.05 20 BN-258 S1 S2-2 S3-34 1033.23 C, 83.70; H, 7.12; N, 8.13 twenty one BN-259 S1 S2-2 S3-35 1241.53 C, 85.13; H, 7.23; N, 6.77 20 BN-260 S1 S2-2 S3-36 1009.04 C, 85.70; H, 4.89; N, 8.33 17 BN-261 S1 S2-2 S3-37 1065.14 C, 85.70; H, 5.39; N, 7.89 16 BN-262 S1 S2-2 S3-38 1065.14 C, 85.70; H, 5.39; N, 7.89 20 BN-263 S1 S2-2 S3-39 1233.47 C, 85.69; H, 6.62; N, 6.81 19 BN-264 S1 S2-2 S3-40 1233.47 C, 85.69; H, 6.62; N, 6.81 17 BN-265 S1 S2-2 S3-41 1233.47 C, 85.69; H, 6.62; N, 6.81 15 BN-266 S1 S2-2 S3-42 1345.68 C, 85.69; H, 7.27; N, 6.25 twenty three BN-267 S1 S2-2 S3-43 1457.90 C, 85.68; H, 7.81; N, 5.76 twenty one BN-268 S1 S2-2 S3-44 1121.25 C, 85.70; H, 5.84; N, 7.50 15 BN-269 S1 S2-2 S3-45 1121.25 C, 85.70; H, 5.84; N, 7.50 twenty three BN-270 S1 S2-2 S3-46 1457.90 C, 85.68; H, 7.81; N, 5.76 twenty one BN-271 S1 S2-2 S3-47 1457.90 C, 85.68; H, 7.81; N, 5.76 25 BN-272 S1 S2-2 S3-48 1521.90 C, 82.08; H, 7.48; N, 5.52 twenty one BN-273 S1 S2-2 S3-49 1409.68 C, 81.80; H, 6.94; N, 5.96 15 BN-274 S1 S2-2 S3-50 1177.36 C, 85.69; H, 6.25; N, 7.14 20 BN-275 S1 S2-2 S3-51 2018.98 C, 85.67; H, 9.64; N, 4.16 twenty one BN-276 S1 S2-2 S3-52 2210.97 C, 78.23; H, 8.80; N, 3.80 20 BN-277 S1 S2-2 S3-53 1313.43 C, 87.79; H, 4.99; N, 6.40 20 BN-278 S1 S2-2 S3-54 1369.54 C, 87.70; H, 5.37; N, 6.14 twenty one BN-279 S1 S2-2 S3-55 1537.86 C, 87.47; H, 6.36; N, 5.46 20 BN-280 S1 S2-2 S3-56 1537.86 C, 87.47; H, 6.36; N, 5.46 20 BN-281 S1 S2-2 S3-57 1313.43 C, 87.79; H, 4.99; N, 6.40 17 BN-282 S1 S2-2 S3-58 1369.54 C, 87.70; H, 5.37; N, 6.14 16 BN-283 S1 S2-2 S3-59 1537.86 C, 87.47; H, 6.36; N, 5.46 twenty three BN-284 S1 S2-2 S3-60 1537.86 C, 87.47; H, 6.36; N, 5.46 15 BN-285 S1 S2-2 S3-61 1617.82 C, 89.09; H, 5.05; N, 5.19 twenty two BN-286 S1 S2-2 S3-62 1842.25 C, 88.67; H, 6.18; N, 4.56 twenty one BN-287 S1 S2-2 S3-63 1617.82 C, 89.09; H, 5.05; N, 5.19 20 BN-288 S1 S2-2 S3-64 1842.25 C, 88.67; H, 6.18; N, 4.56 19 BN-289 S1 S2-2 S3-65 738.79 C, 84.54; H, 6.41; N, 7.58 17 BN-290 S1 S2-2 S3-66 790.86 C, 85.05; H, 6.50; N, 7.08 15 BN-291 S1 S2-2 S3-67 895.01 C, 85.89; H, 6.64; N, 6.26 twenty three BN-292 S1 S2-2 S3-68 778.77 C, 86.37; H, 5.05; N, 7.19 twenty one BN-293 S1 S2-2 S3-69 806.82 C, 86.34; H, 5.37; N, 6.94 twenty two BN-294 S1 S2-2 S3-70 806.82 C, 86.34; H, 5.37; N, 6.94 twenty one BN-295 S1 S2-2 S3-71 890.98 C, 86.28; H, 6.22; N, 6.29 20 BN-296 S1 S2-2 S3-72 890.98 C, 86.28; H, 6.22; N, 6.29 20 BN-297 S1 S2-2 S3-73 890.98 C, 86.28; H, 6.22; N, 6.29 twenty one BN-298 S1 S2-2 S3-74 947.09 C, 86.24; H, 6.71;; N, 5.92 20 BN-299 S1 S2-2 S3-75 1003.20 C, 86.20; H, 7.13; N, 5.58 17 BN-300 S1 S2-2 S3-76 834.87 C, 86.32; H, 5.67; N, 6.71 16 BN-301 S1 S2-2 S3-77 834.87 C, 86.32; H, 5.67; N, 6.71 twenty three BN-302 S1 S2-2 S3-78 1003.20 C, 86.20; H, 7.13; N, 5.58 15 BN-303 S1 S2-2 S3-79 1003.20 C, 86.20; H, 7.13; N, 5.58 20 BN-304 S1 S2-2 S3-80 1035.20 C, 83.54; H, 6.91; N, 5.41 twenty one BN-305 S1 S2-2 S3-81 979.09 C, 83.42; H, 6.49; N, 5.72 20 BN-306 S1 S2-2 S3-82 862.93 C, 86.30; H, 5.96; N, 6.49 20 BN-307 S1 S2-2 S3-83 1283.74 C, 86.08; H, 8.72; N, 4.36 twenty one BN-308 S1 S2-2 S3-84 1379.73 C, 80.09; H, 8.11; N, 4.06 20 BN-309 S1 S2-2 S3-85 930.96 C, 87.73; H, 5.09; N, 6.02 twenty one BN-310 S1 S2-2 S3-86 959.02 C, 87.67; H, 5.36; N, 5.84 15 BN-311 S1 S2-2 S3-87 1043.18 C, 87.51; H, 6.09; N, 5.37 20 BN-312 S1 S2-2 S3-88 1043.18 C, 87.51; H, 6.09; N, 5.37 twenty one BN-313 S1 S2-2 S3-89 930.96 C, 87.73; H, 5.09; N, 6.02 20 BN-314 S1 S2-2 S3-90 959.02 C, 87.67; H, 5.36; N, 5.84 20 BN-315 S1 S2-2 S3-90 1043.18 C, 87.51; H, 6.09; N, 5.37 twenty one BN-316 S1 S2-2 S3-92 1043.18 C, 87.51; H, 6.09; N, 5.37 20 BN-317 S1 S2-2 S3-93 1083.16 C, 88.71; H, 5.12; N, 5.17 20 BN-318 S1 S2-2 S3-94 1195.37 C, 88.42; H, 5.99; N, 4.69 17 BN-319 S1 S2-2 S3-95 1083.16 C, 88.71; H, 5.12; N, 5.17 16 BN-320 S1 S2-2 S3-96 1195.37 C, 88.42; H, 5.99; N, 4.69 twenty three BN-321 S1 S2-3 S3-33 1097.40 C, 83.18; H, 8.17; N, 7.66 15 BN-322 S1 S2-3 S3-34 1201.55 C, 83.97; H, 8.14; N, 6.99 twenty two BN-323 S1 S2-3 S3-35 1409.86 C, 85.19; H, 8.08; N, 5.96 twenty one BN-324 S1 S2-3 S3-36 1177.36 C, 85.69; H, 6.25; N, 7.14 20 BN-325 S1 S2-3 S3-37 1233.47 C, 85.69; H, 6.62; N, 6.81 19 BN-326 S1 S2-3 S3-38 1233.47 C, 85.69; H, 6.62; N, 6.81 17 BN-327 S1 S2-3 S3-39 1401.79 C, 85.68; H, 7.55; N, 6.00 15 BN-328 S1 S2-3 S3-40 1401.79 C, 85.68; H, 7.55; N, 6.00 twenty three BN-329 S1 S2-3 S3-41 1401.79 C, 85.68; H, 7.55; N, 6.00 twenty one BN-330 S1 S2-3 S3-42 1514.01 C, 85.68; H, 8.06; N, 5.55 15 BN-331 S1 S2-3 S3-43 1626.22 C, 85.68; H, 8.49; N, 5.17 20 BN-332 S1 S2-3 S3-44 1289.58 C, 85.69; H, 6.96; N, 6.52 twenty one BN-333 S1 S2-3 S3-45 1289.58 C, 85.69; H, 6.96; N, 6.52 20 BN-334 S1 S2-3 S3-46 1626.22 C, 85.68; H, 8.49; N, 5.17 20 BN-335 S1 S2-3 S3-47 1626.22 C, 85.68; H, 8.49; N, 5.17 twenty one BN-336 S1 S2-3 S3-48 1690.22 C, 82.43; H, 8.17; N, 4.97 20 BN-337 S1 S2-3 S3-49 1578.00 C, 82.20; H, 7.73; N, 5.33 20 BN-338 S1 S2-3 S3-50 1345.68 C, 85.69; H, 7.27; N, 6.25 17 BN-339 S1 S2-3 S3-51 2187.30 C, 85.66; H, 10.00; N, 3.84 16 BN-340 S1 S2-3 S3-52 2379.29 C, 78.75; H, 9.19; N, 3.53 15 BN-341 S1 S2-3 S3-53 1481.75 C, 87.54; H, 6.05; N, 5.67 twenty three BN-342 S1 S2-3 S3-54 1537.86 C, 87.47; H, 6.36; N, 5.46 twenty one BN-343 S1 S2-3 S3-55 1664.10 C, 87.33; H, 6.97; N, 5.05 twenty two BN-344 S1 S2-3 S3-56 1664.10 C, 87.33; H, 6.97; N, 5.05 twenty one BN-345 S1 S2-3 S3-57 1481.75 C, 87.54; H, 6.05; N, 5.67 20 BN-346 S1 S2-3 S3-58 1537.86 C, 87.47; H, 6.36; N, 5.46 20 BN-347 S1 S2-3 S3-59 1706.18 C, 87.29; H, 7.15; N, 4.93 twenty one BN-348 S1 S2-3 S3-60 1706.18 C, 87.29; H, 7.15; N, 4.93 20 BN-349 S1 S2-3 S3-61 1786.14 C, 88.76; H, 5.93; N, 4.71 17 BN-350 S1 S2-3 S3-62 2010.58 C, 88.41; H, 6.87; N, 4.18 16 BN-351 S1 S2-3 S3-63 1786.14 C, 88.76; H, 5.93; N, 4.71 twenty three BN-352 S1 S2-3 S3-64 2235.01 C, 88.13; H, 7.62; N, 3.76 15 BN-353 S1 S2-3 S3-65 907.11 C, 84.74; H, 7.89; N, 6.18 20 BN-354 S1 S2-3 S3-66 959.19 C, 85.15; H, 7.88; N, 5.84 twenty one BN-355 S1 S2-3 S3-67 1063.34 C, 85.85; H, 7.87; N, 5.27 20 BN-356 S1 S2-3 S3-68 947.09 C, 86.24; H, 6.71; N, 5.92 20 BN-357 S1 S2-3 S3-69 975.14 C, 86.22; H, 6.93; N, 5.75 twenty one BN-358 S1 S2-3 S3-70 975.14 C, 86.22; H, 6.93; N, 5.75 20 BN-359 S1 S2-3 S3-71 1059.31 C, 86.17; H, 7.52; N, 5.29 twenty one BN-360 S1 S2-3 S3-72 1059.31 C, 86.17; H, 7.52; N, 5.29 15 BN-361 S1 S2-3 S3-73 1059.31 C, 86.17; H, 7.52; N, 5.29 20 BN-362 S1 S2-3 S3-74 1115.41 C, 86.15; H, 7.86; N, 5.02 twenty one BN-363 S1 S2-3 S3-75 1171.52 C, 86.12; H, 8.17; N, 4.78 20 BN-364 S1 S2-3 S3-76 1003.20 C, 86.20; H, 7.13; N, 5.58 20 BN-365 S1 S2-3 S3-77 1003.20 C, 86.20; H, 7.13; N, 5.58 twenty one BN-366 S1 S2-3 S3-78 1171.52 C, 86.12; H, 8.17; N, 4.78 20 BN-367 S1 S2-3 S3-79 1171.52 C, 86.12; H, 8.17; N, 4.78 20 BN-368 S1 S2-3 S3-80 1203.52 C, 83.83; H, 7.96; N, 4.66 17 BN-369 S1 S2-3 S3-81 1147.41 C, 83.74; H, 7.64; N, 4.88 16 BN-370 S1 S2-3 S3-82 1031.25 C, 86.19; H, 7.33; N, 5.43 twenty three BN-371 S1 S2-3 S3-83 1452.06 C, 86.03; H, 9.37; N, 3.86 15 BN-372 S1 S2-3 S3-84 1548.06 C, 80.69; H, 8.79; N, 3.62 twenty two BN-373 S1 S2-3 S3-85 1099.29 C, 87.41; H, 6.51; N, 5.10 twenty one BN-374 S1 S2-3 S3-86 1127.34 C, 87.37; H, 6.71; N, 4.97 20 BN-375 S1 S2-3 S3-87 1211.50 C, 87.24; H, 7.24; N, 4.62 19 BN-376 S1 S2-3 S3-88 1211.50 C, 87.24; H, 7.24; N, 4.62 17 BN-377 S1 S2-3 S3-89 1099.29 C, 87.41; H, 6.51; N, 5.10 15 BN-378 S1 S2-3 S3-90 1127.34 C, 87.37; H, 6.71; N, 4.97 twenty three BN-379 S1 S2-3 S3-90 1211.50 C, 87.24; H, 7.24; N, 4.62 twenty one BN-380 S1 S2-3 S3-92 1211.50 C, 87.24; H, 7.24; N, 4.62 15 BN-381 S1 S2-3 S3-93 1251.48 C, 88.30; H, 6.36; N, 4.48 20 BN-382 S1 S2-3 S3-94 1363.70 C, 88.08; H, 7.02; N, 4.11 twenty one BN-383 S1 S2-3 S3-95 1251.48 C, 88.30; H, 6.36; N, 4.48 20 BN-384 S1 S2-3 S3-96 1363.70 C, 88.08; H, 7.02; N, 4.11 20 BN-385 S1 S2-4 S3-33 1177.36 C, 85.69; H, 6.25; N, 7.14 20 BN-386 S1 S2-4 S3-34 1281.51 C, 86.23; H, 6.37; N, 6.56 19 BN-387 S1 S2-4 S3-35 1489.82 C, 87.07; H, 6.56; N, 5.64 17 BN-388 S1 S2-4 S3-36 1257.32 C, 87.89; H, 4.57; N, 6.68 15 BN-389 S1 S2-4 S3-37 1313.43 C, 87.79; H, 4.99; N, 6.40 twenty three BN-390 S1 S2-4 S3-38 1313.43 C, 87.79; H, 4.99; N, 6.40 twenty one BN-391 S1 S2-4 S3-39 1481.75 C, 87.54; H, 6.05; N, 5.67 15 BN-392 S1 S2-4 S3-40 1481.75 C, 87.54; H, 6.05; N, 5.67 20 BN-393 S1 S2-4 S3-41 1481.75 C, 87.54; H, 6.05; N, 5.67 twenty one BN-394 S1 S2-4 S3-42 1593.97 C, 87.41; H, 6.64; N, 5.27 20 BN-395 S1 S2-4 S3-43 1706.18 C, 87.29; H, 7.15; N, 4.93 20 BN-396 S1 S2-4 S3-44 1369.54 C, 87.70; H, 5.37; N, 6.14 twenty one BN-397 S1 S2-4 S3-45 1369.54 C, 87.70; H, 5.37; N, 6.14 20 BN-398 S1 S2-4 S3-46 1706.18 C, 87.29; H, 7.15; N, 4.93 20 BN-399 S1 S2-4 S3-47 1706.18 C, 87.29; H, 7.15; N, 4.93 17 BN-400 S1 S2-4 S3-48 1770.18 C, 84.14; H, 6.89; N, 4.75 16 BN-401 S1 S2-4 S3-49 1657.96 C, 84.04; H, 6.38; N, 5.07 20 BN-402 S1 S2-4 S3-50 1425.64 C, 87.62; H, 5.73; N, 5.90 19 BN-403 S1 S2-4 S3-51 2267.26 C, 86.88; H, 8.94; N, 3.71 17 BN-404 S1 S2-4 S3-52 2459.25 C, 80.10; H, 8.24; N, 3.42 15 BN-405 S1 S2-4 S3-53 1561.71 C, 89.21; H, 4.71; N, 5.38 twenty three BN-406 S1 S2-4 S3-54 1617.82 C, 89.09; H, 5.05; N, 5.19 twenty one BN-407 S1 S2-4 S3-55 1786.14 C, 88.76; H, 5.93; N, 4.71 15 BN-408 S1 S2-4 S3-56 1786.14 C, 88.76; H, 5.93; N, 4.71 20 BN-409 S1 S2-4 S3-57 1561.71 C, 89.21; H, 4.71; N, 5.38 twenty one BN-410 S1 S2-4 S3-58 1617.82 C, 89.09; H, 5.05; N, 5.19 20 BN-411 S1 S2-4 S3-59 1786.14 C, 88.76; H, 5.93; N, 4.71 20 BN-412 S1 S2-4 S3-60 1786.14 C, 88.76; H, 5.93; N, 4.71 twenty one BN-413 S1 S2-4 S3-61 1866.10 C, 90.11; H, 4.81; N, 4.50 20 BN-414 S1 S2-4 S3-62 2090.54 C, 89.63; H, 5.83; N, 4.02 20 BN-415 S1 S2-4 S3-63 1866.10 C, 90.11; H, 4.81; N, 4.50 17 BN-416 S1 S2-4 S3-64 2090.54 C, 89.63; H, 5.83; N, 4.02 16 BN-417 S1 S2-4 S3-65 987.07 C, 87.61; H, 5.62; N, 5.68 20 BN-418 S1 S2-4 S3-66 1039.15 C, 87.84; H, 5.72; N, 5.39 19 BN-419 S1 S2-4 S3-67 1143.30 C, 88.25; H, 5.91; N, 4.90 17 BN-420 S1 S2-4 S3-68 1027.05 C, 88.88; H, 4.61; N, 5.46 15 BN-421 S1 S2-4 S3-69 1055.10 C, 88.79; H, 4.87; N, 5.31 twenty three BN-422 S1 S2-4 S3-70 1055.10 C, 88.79; H, 4.87; N, 5.31 twenty one BN-423 S1 S2-4 S3-71 1139.27 C, 88.56; H, 5.57; N, 4.92 15 BN-424 S1 S2-4 S3-72 1139.27 C, 88.56; H, 5.57; N, 4.92 20 BN-425 S1 S2-4 S3-73 1139.27 C, 88.56; H, 5.57; N, 4.92 twenty one BN-426 S1 S2-4 S3-74 1195.37 C, 88.42; H, 5.99; N, 4.69 20 BN-427 S1 S2-4 S3-75 1251.48 C, 88.30; H, 6.36; N, 4.48 20 BN-428 S1 S2-4 S3-76 1083.16 C, 88.71; H, 5.12; N, 5.17 twenty one BN-429 S1 S2-4 S3-77 1083.16 C, 88.71; H, 5.12; N, 5.17 20 BN-430 S1 S2-4 S3-78 1251.48 C, 88.30; H, 6.36; N, 4.48 20 BN-431 S1 S2-4 S3-79 1251.48 C, 88.30; H, 6.36; N, 4.48 17 BN-432 S1 S2-4 S3-80 1283.48 C, 86.09; H, 6.20; N, 4.37 20 BN-433 S1 S2-4 S3-81 1227.37 C, 86.12; H, 5.83; N, 4.56 19 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 twenty one BN-441 S1 S2-4 S3-89 1179.25 C, 89.63; H, 4.70; N, 4.75 20 BN-442 S1 S2-4 S3-90 1207.30 C, 89.54; H, 4.93; N, 4.64 20 BN-443 S1 S2-4 S3-90 1229.39 C, 88.91; H, 5.66; N, 4.56 20 BN-444 S1 S2-4 S3-92 1229.39 C, 88.91; H, 5.66; N, 4.56 19 BN-445 S1 S2-4 S3-93 1331.44 C, 90.21; H, 4.77; N, 4.21 17 BN-446 S1 S2-4 S3-94 1443.66 C, 89.85; H, 5.52; N, 3.88 15 BN-447 S1 S2-4 S3-95 1331.44 C, 90.21; H, 4.77; N, 4.21 twenty three BN-448 S1 S2-4 S3-96 1443.66 C, 89.85; H, 5.52; N, 3.88 twenty one BN-449 S1 S2-5 S3-33 1533.75 C, 84.58; H, 5.59; N, 9.13 15 BN-450 S1 S2-5 S3-34 1637.90 C, 85.06; H, 5.72; N, 8.55 20 BN-451 S1 S2-5 S3-35 1846.20 C, 85.88; H, 5.95; N, 7.59 twenty one BN-452 S1 S2-5 S3-36 1613.71 C, 86.34; H, 4.31; N, 8.68 20 BN-453 S1 S2-5 S3-37 1669.82 C, 86.32; H, 4.65; N, 8.39 20 BN-454 S1 S2-5 S3-38 1669.82 C, 86.32; H, 4.65; N, 8.39 twenty one BN-455 S1 S2-5 S3-39 1838.14 C, 86.25; H, 5.54; N, 7.62 20 BN-456 S1 S2-5 S3-40 1838.14 C, 86.25; H, 5.54; N, 7.62 20 BN-457 S1 S2-5 S3-41 1838.14 C, 86.25; H, 5.54; N, 7.62 17 BN-458 S1 S2-5 S3-42 1950.36 C, 86.22; H, 6.05; N, 7.18 16 BN-459 S1 S2-5 S3-43 2062.57 C, 86.19; H, 6.50; N, 6.79 20 BN-460 S1 S2-5 S3-44 1725.92 C, 86.29; H, 4.96; N, 8.12 19 BN-461 S1 S2-5 S3-45 1725.92 C, 86.29; H, 4.96; N, 8.12 17 BN-462 S1 S2-5 S3-46 2062.57 C, 86.19; H, 6.50; N, 6.79 15 BN-463 S1 S2-5 S3-47 2062.57 C, 86.19; H, 6.50; N, 6.79 twenty three BN-464 S1 S2-5 S3-48 2126.57 C, 83.59; H, 6.30; N, 6.59 twenty one BN-465 S1 S2-5 S3-49 2014.35 C, 83.48; H, 5.85; N, 6.95 15 BN-466 S1 S2-5 S3-50 1782.03 C, 86.27; H, 5.26; N, 7.86 20 BN-467 S1 S2-5 S3-51 2623.65 C, 86.07; H, 8.18; N, 5.34 twenty one BN-468 S1 S2-5 S3-52 2815.64 C, 80.20; H, 7.63; N, 4.97 20 BN-469 S1 S2-5 S3-53 1918.10 C, 87.67; H, 4.47; N, 7.30 20 BN-470 S1 S2-5 S3-54 1974.21 C, 87.61; H, 4.75; N, 7.09 twenty one BN-471 S1 S2-5 S3-55 2142.53 C, 87.45; H, 5.50; N, 6.54 20 BN-472 S1 S2-5 S3-56 2142.53 C, 87.45; H, 5.50; N, 6.54 20 BN-473 S1 S2-5 S3-57 1918.10 C, 87.67; H, 4.47; N, 7.30 17 BN-474 S1 S2-5 S3-58 1974.21 C, 87.61; H, 4.75; N, 7.09 16 BN-475 S1 S2-5 S3-59 2142.53 C, 87.45; H, 5.50; N, 6.54 20 BN-476 S1 S2-5 S3-60 2142.53 C, 87.45; H, 5.50; N, 6.54 20 BN-477 S1 S2-5 S3-61 2222.49 C, 88.63; H, 4.58; N, 6.30 twenty one BN-478 S1 S2-5 S3-62 2446.92 C, 88.36; H, 5.48; N, 5.72 20 BN-479 S1 S2-5 S3-63 2222.49 C, 88.63; H, 4.58; N, 6.30 20 BN-480 S1 S2-5 S3-64 2446.92 C, 88.36; H, 5.48; N, 5.72 20 BN-481 S1 S2-5 S3-65 1343.46 C, 85.83; H, 5.03; N, 8.34 19 BN-482 S1 S2-5 S3-66 1395.53 C, 86.07; H, 5.13; N, 8.03 17 BN-483 S1 S2-5 S3-67 1499.69 C, 86.50; H, 5.31; N, 7.47 15 BN-484 S1 S2-5 S3-68 1383.44 C, 86.82; H, 4.30; N, 8.10 twenty three BN-485 S1 S2-5 S3-69 1411.49 C, 86.80; H, 4.50; N, 7.94 twenty one BN-486 S1 S2-5 S3-70 1411.49 C, 86.80; H, 4.50; N, 7.94 15 BN-487 S1 S2-5 S3-71 1495.65 C, 86.73; H, 5.05; N, 7.49 20 BN-488 S1 S2-5 S3-72 1495.65 C, 86.73; H, 5.05; N, 7.49 twenty one BN-489 S1 S2-5 S3-73 1495.65 C, 86.73; H, 5.05; N, 7.49 20 BN-490 S1 S2-5 S3-74 1551.76 C, 86.69; H, 5.39; N, 7.22 20 BN-491 S1 S2-5 S3-75 1607.87 C, 86.65; H, 5.70; N, 6.97 twenty one BN-492 S1 S2-5 S3-76 1439.55 C, 86.77; H, 4.69; N, 7.78 20 BN-493 S1 S2-5 S3-77 1439.55 C, 86.77; H, 4.69; N, 7.78 20 BN-494 S1 S2-5 S3-78 1607.87 C, 86.65; H, 5.70; N, 6.97 17 BN-495 S1 S2-5 S3-79 1607.87 C, 86.65; H, 5.70; N, 6.97 16 BN-496 S1 S2-5 S3-80 1639.87 C, 84.96; H, 5.59; N, 6.83 20 BN-497 S1 S2-5 S3-81 1583.76 C, 84.94; H, 5.28; N, 7.08 19 BN-498 S1 S2-5 S3-82 1467.60 C, 86.75; H, 4.88; N, 7.64 17 BN-499 S1 S2-5 S3-83 1888.41 C, 86.50; H, 6.99; N, 5.93 15 BN-500 S1 S2-5 S3-84 1984.40 C, 82.32; H, 6.65; N, 5.65 twenty three BN-501 S1 S2-5 S3-85 1535.63 C, 87.60; H, 4.40; N, 7.30 twenty one BN-502 S1 S2-5 S3-86 1563.69 C, 87.57; H, 4.58; N, 7.17 15 BN-503 S1 S2-5 S3-87 1647.85 C, 87.47; H, 5.08; N, 6.80 20 BN-504 S1 S2-5 S3-88 1647.85 C, 87.47; H, 5.08; N, 6.80 twenty one BN-505 S1 S2-5 S3-89 1535.63 C, 87.60; H, 4.40; N, 7.30 20 BN-506 S1 S2-5 S3-90 1563.69 C, 87.57; H, 4.58; N, 7.17 20 BN-507 S1 S2-5 S3-90 1647.85 C, 87.47; H, 5.08; N, 6.80 twenty one BN-508 S1 S2-5 S3-92 1647.85 C, 87.47; H, 5.08; N, 6.80 20 BN-509 S1 S2-5 S3-93 1687.83 C, 88.24; H, 4.48; N, 6.64 20 BN-510 S1 S2-5 S3-94 1800.05 C, 88.08; H, 5.10; N, 6.23 17 BN-511 S1 S2-5 S3-95 1687.83 C, 88.24; H, 4.48; N, 6.64 16 BN-512 S1 S2-5 S3-96 1800.05 C, 88.08; H, 5.10; N, 6.23 20 BN-513 S1 S2-6 S3-33 1541.81 C, 84.13; H, 6.08; N, 9.08 20 BN-514 S1 S2-6 S3-34 1645.96 C, 84.65; H, 6.19; N, 8.51 twenty one BN-515 S1 S2-6 S3-35 1854.27 C, 85.50; H, 6.36; N, 7.55 15 BN-516 S1 S2-6 S3-36 1621.77 C, 85.91; H, 4.79; N, 8.64 20 BN-517 S1 S2-6 S3-37 1677.88 C, 85.90; H, 5.11; N, 8.35 twenty one BN-518 S1 S2-6 S3-38 1677.88 C, 85.90; H, 5.11; N, 8.35 20 BN-519 S1 S2-6 S3-39 1846.20 C, 85.88; H, 5.95; N, 7.59 20 BN-520 S1 S2-6 S3-40 1846.20 C, 85.88; H, 5.95; N, 7.59 twenty one BN-521 S1 S2-6 S3-41 1846.20 C, 85.88; H, 5.95; N, 7.59 20 BN-522 S1 S2-6 S3-42 1958.42 C, 85.86; H, 6.43; N, 7.15 20 BN-523 S1 S2-6 S3-43 2070.64 C, 85.85; H, 6.86; N, 6.76 17 BN-524 S1 S2-6 S3-44 1733.99 C, 85.89; H, 5.41; N, 8.08 16 BN-525 S1 S2-6 S3-45 1733.99 C, 85.89; H, 5.41; N, 8.08 20 BN-526 S1 S2-6 S3-46 2070.64 C, 85.85; H, 6.86; N, 6.76 20 BN-527 S1 S2-6 S3-47 2070.64 C, 85.85; H, 6.86; N, 6.76 16 BN-528 S1 S2-6 S3-48 2134.63 C, 83.28; H, 6.66; N, 6.56 20 BN-529 S1 S2-6 S3-49 2022.42 C, 83.15; H, 6.23; N, 6.93 20 BN-530 S1 S2-6 S3-50 1790.10 C, 85.88; H, 5.69; N, 7.82 twenty one BN-531 S1 S2-6 S3-51 2631.72 C, 85.80; H, 8.46; N, 5.32 15 BN-532 S1 S2-6 S3-52 2823.70 C, 79.97; H, 7.89; N, 4.96 20 BN-533 S1 S2-6 S3-53 1926.16 C, 87.30; H, 4.87; N, 7.27 twenty one BN-534 S1 S2-6 S3-54 1982.27 C, 87.25; H, 5.14; N, 7.07 20 BN-535 S1 S2-6 S3-55 2150.60 C, 87.13; H, 5.86; N, 6.51 20 BN-536 S1 S2-6 S3-56 2150.60 C, 87.13; H, 5.86; N, 6.51 twenty one BN-537 S1 S2-6 S3-57 1926.16 C, 87.30; H, 4.87; N, 7.27 20 BN-538 S1 S2-6 S3-58 1982.27 C, 87.25; H, 5.14; N, 7.07 20 BN-539 S1 S2-6 S3-59 2150.60 C, 87.13; H, 5.86; N, 6.51 17 BN-540 S1 S2-6 S3-60 2150.60 C, 87.13; H, 5.86; N, 6.51 16 BN-541 S1 S2-6 S3-61 2230.56 C, 88.31; H, 4.93; N, 6.28 20 BN-542 S1 S2-6 S3-62 2454.99 C, 88.06; H, 5.79; N, 5.71 20 BN-543 S1 S2-6 S3-63 2230.56 C, 88.31; H, 4.93; N, 6.28 17 BN-544 S1 S2-6 S3-64 2454.99 C, 88.06; H, 5.79; N, 5.71 16 BN-545 S1 S2-6 S3-65 1351.52 C, 85.32; H, 5.59; N, 8.29 20 BN-546 S1 S2-6 S3-66 1403.60 C, 85.57; H, 5.67;; N, 7.98 20 BN-547 S1 S2-6 S3-67 1507.75 C, 86.03; H, 5.82; N, 7.43 twenty one BN-548 S1 S2-6 S3-68 1391.50 C, 86.32; H, 4.85; N, 8.05 20 BN-549 S1 S2-6 S3-69 1419.56 C, 86.30; H, 5.04; N, 7.89 20 BN-550 S1 S2-6 S3-70 1419.56 C, 86.30; H, 5.04; N, 7.89 20 BN-551 S1 S2-6 S3-71 1503.72 C, 86.27; H, 5.56; N, 7.45 19 BN-552 S1 S2-6 S3-72 1503.72 C, 86.27; H, 5.56; N, 7.45 17 BN-553 S1 S2-6 S3-73 1503.72 C, 86.27; H, 5.56; N, 7.45 15 BN-554 S1 S2-6 S3-74 1559.83 C, 86.24; H, 5.88; N, 7.18 twenty three BN-555 S1 S2-6 S3-75 1615.93 C, 86.22; H, 6.18; N, 6.93 twenty one BN-556 S1 S2-6 S3-76 1447.61 C, 86.29; H, 5.22; N, 7.74 15 BN-557 S1 S2-6 S3-77 1447.61 C, 86.29; H, 5.22; N, 7.74 20 BN-558 S1 S2-6 S3-78 1615.93 C, 86.22; H, 6.18; N, 6.93 twenty one BN-559 S1 S2-6 S3-79 1615.93 C, 86.22; H, 6.18; N, 6.93 20 BN-560 S1 S2-6 S3-80 1647.93 C, 84.55; H, 6.06; N, 6.80 20 BN-561 S1 S2-6 S3-81 1591.82 C, 84.51; H, 5.76; N, 7.04 twenty one BN-562 S1 S2-6 S3-82 1475.66 C, 86.28; H, 5.40; N, 7.59 20 BN-563 S1 S2-6 S3-83 1896.47 C, 86.13; H, 7.39; N, 5.91 20 BN-564 S1 S2-6 S3-84 1992.47 C, 81.98; H, 7.03; N, 5.62 17 BN-565 S1 S2-6 S3-85 1543.70 C, 87.14; H, 4.90; N, 7.26 16 BN-566 S1 S2-6 S3-86 1571.75 C, 87.12; H, 5.07; N, 7.13 20 BN-567 S1 S2-6 S3-87 1655.91 C, 87.04; H, 5.54; N, 6.77 19 BN-568 S1 S2-6 S3-88 1655.91 C, 87.04; H, 5.54; N, 6.77 17 BN-569 S1 S2-6 S3-89 1543.70 C, 87.14; H, 4.90; N, 7.26 15 BN-570 S1 S2-6 S3-90 1571.75 C, 87.12; H, 5.07; N, 7.13 twenty three BN-571 S1 S2-6 S3-90 1655.91 C, 87.04; H, 5.54; N, 6.77 twenty one BN-572 S1 S2-6 S3-92 1655.91 C, 87.04; H, 5.54; N, 6.77 15 BN-573 S1 S2-6 S3-93 1695.89 C, 87.82; H, 4.93; N, 6.61 20 BN-574 S1 S2-6 S3-94 1808.11 C, 87.69; H, 5.52; N, 6.20 twenty one BN-575 S1 S2-6 S3-95 1695.89 C, 87.82; H, 4.93; N, 6.61 20 BN-576 S1 S2-6 S3-96 1808.11 C, 87.69; H, 5.52; N, 6.20 20 BN-577 S1 S2-7 S3-1 1610.97 C, 84.91; H, 7.47; N, 6.93 17 BN-578 S1 S2-7 S3-3 1875.15 C, 85.75; H, 6.71; N, 5.97 18 BN-579 S1 S2-7 S3-5 1819.09 C, 85.78; H, 7.51; N, 6.18 20 BN-580 S1 S2-7 S3-7 1987.28 C, 85.79; H, 8.01; N, 5.68 twenty one BN-581 S1 S2-7 S3-9 1847.12 C, 85.77; H, 7.52; N, 6.07 20 BN-582 S1 S2-7 S3-97 2019.27 C, 84.47; H, 7.92; N, 5.57 17 BN-583 S1 S2-7 S3-98 2019.27 C, 84.40; H, 7.93; N, 5.53 16 BN-584 S1 S2-7 S3-99 2277.13 C, 83.36; H, 8.57; N, 4.92; twenty three

。 Effect Example 1 The light-emitting molecular structure adopted in the comparative effect example is as follows:

.

The compounds represented by the formulae BN-1 to BN-584 are the molecular structures of the materials provided by the present invention (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. Any compound shown in formula BN-n (n=1-584) or BN-Rm (m=1-7) was used as the doped light-emitting material and H-1 as the host material to prepare a doped thin film (thickness of 150±15nm), the doping concentration of the doped luminescent material is 3wt% (weight percent concentration), and then the emission spectra of the doped films are tested respectively. The test results are listed in Table 2 .

The luminescent peak positions of the luminescent compounds provided by the present invention listed in Table 2 and the corresponding pairs

The comparison of the luminescence peak positions of the comparative compounds shows that the luminescence peak positions of the luminescent compounds provided by the present invention are red-shifted by 7-62 nm, that is, shifted to long wavelengths by 7-62 nm, compared with the luminescence peak positions of the corresponding comparative compounds. The above-mentioned effect examples prove that the luminescence peak of the boron-nitrogen compound of the present invention 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 provided by the present invention is designed. The principles and methods are effective in providing a luminescent material with a narrow emission peak in the green to red region.

[Table 2] BN-n (n = 1-584) emission spectrum test parameters. Compound (Dn-m) Compound luminescence spectrum peak position (nm) Compound luminescence spectrum half width (nm) Comparative compound (Dn-mR) The peak position of the emission spectrum of the comparative compound (nm) The half-peak width (nm) of the emission spectrum of the comparative compound BN-1 520 41 BN-R-1 487 37 BN-2 520 40 BN-R-1 487 37 BN-3 519 41 BN-R-1 487 37 BN-4 520 43 BN-R-1 487 37 BN-5 521 42 BN-R-1 487 37 BN-6 519 43 BN-R-1 487 37 BN-7 520 42 BN-R-1 487 37 BN-8 519 43 BN-R-1 487 37 BN-9 521 44 BN-R-1 487 37 BN-10 519 43 BN-R-1 487 37 BN-11 520 43 BN-R-1 487 37 BN-12 521 44 BN-R-1 487 37 BN-13 522 42 BN-R-1 487 37 BN-14 521 43 BN-R-1 487 37 BN-15 522 44 BN-R-1 487 37 BN-16 522 44 BN-R-1 487 37 BN-17 509 43 BN-R-1 487 37 BN-18 509 41 BN-R-1 487 37 BN-19 510 44 BN-R-1 487 37 BN-20 509 43 BN-R-1 487 37 BN-21 509 45 BN-R-1 487 37 BN-22 510 45 BN-R-1 487 37 BN-23 509 44 BN-R-1 487 37 BN-24 510 44 BN-R-1 487 37 BN-25 510 43 BN-R-1 487 37 BN-26 509 44 BN-R-1 487 37 BN-27 510 43 BN-R-1 487 37 BN-28 511 45 BN-R-1 487 37 BN-29 511 42 BN-R-1 487 37 BN-30 510 43 BN-R-1 487 37 BN-31 512 42 BN-R-1 487 37 BN-32 512 44 BN-R-1 487 37 BN-33 529 42 BN-R-2 496 36 BN-34 530 43 BN-R-2 496 36 BN-35 529 42 BN-R-2 496 36 BN-36 530 41 BN-R-2 496 36 BN-37 531 43 BN-R-2 496 36 BN-38 530 43 BN-R-2 496 36 BN-39 529 42 BN-R-2 496 36 BN-40 530 42 BN-R-2 496 36 BN-41 531 43 BN-R-2 496 36 BN-42 530 42 BN-R-2 496 36 BN-43 529 43 BN-R-2 496 36 BN-44 530 42 BN-R-2 496 36 BN-45 531 42 BN-R-2 496 36 BN-46 531 43 BN-R-2 496 36 BN-47 532 42 BN-R-2 496 36 BN-48 532 42 BN-R-2 496 36 BN-49 518 41 BN-R-2 496 36 BN-50 519 43 BN-R-2 496 36 BN-51 519 43 BN-R-2 496 36 BN-52 520 43 BN-R-2 496 36 BN-53 519 42 BN-R-2 496 36 BN-54 520 41 BN-R-2 496 36 BN-55 519 42 BN-R-2 496 36 BN-56 519 44 BN-R-2 496 36 BN-57 520 43 BN-R-2 496 36 BN-58 520 43 BN-R-2 496 36 BN-59 518 44 BN-R-2 496 36 BN-60 519 42 BN-R-2 496 36 BN-61 519 43 BN-R-2 496 36 BN-62 520 43 BN-R-2 496 36 BN-63 521 42 BN-R-2 496 36 BN-64 522 43 BN-R-2 496 36 BN-65 526 42 BN-R-3 493 35 BN-66 527 42 BN-R-3 493 35 BN-67 527 41 BN-R-3 493 35 BN-68 526 42 BN-R-3 493 35 BN-69 527 43 BN-R-3 493 35 BN-70 527 42 BN-R-3 493 35 BN-71 525 43 BN-R-3 493 35 BN-72 525 42 BN-R-3 493 35 BN-73 526 43 BN-R-3 493 35 BN-74 527 43 BN-R-3 493 35 BN-75 526 42 BN-R-3 493 35 BN-76 527 43 BN-R-3 493 35 BN-77 527 44 BN-R-3 493 35 BN-78 528 42 BN-R-3 493 35 BN-79 527 43 BN-R-3 493 35 BN-80 528 42 BN-R-3 493 35 BN-81 515 43 BN-R-3 493 35 BN-82 516 42 BN-R-3 493 35 BN-83 516 43 BN-R-3 493 35 BN-84 516 42 BN-R-3 493 35 BN-85 515 43 BN-R-3 493 35 BN-86 515 43 BN-R-3 493 35 BN-87 516 42 BN-R-3 493 35 BN-88 517 44 BN-R-3 493 35 BN-89 517 44 BN-R-3 493 35 BN-90 516 45 BN-R-3 493 35 BN-91 515 42 BN-R-3 493 35 BN-92 517 43 BN-R-3 493 35 BN-93 517 43 BN-R-3 493 35 BN-94 516 42 BN-R-3 493 35 BN-95 518 43 BN-R-3 493 35 BN-96 518 42 BN-R-3 493 35 BN-97 538 44 BN-R-4 505 33 BN-98 537 43 BN-R-4 505 33 BN-99 539 43 BN-R-4 505 33 BN-100 538 44 BN-R-4 505 33 BN-101 538 45 BN-R-4 505 33 BN-102 538 42 BN-R-4 505 33 BN-103 537 43 BN-R-4 505 33 BN-104 537 44 BN-R-4 505 33 BN-105 537 44 BN-R-4 505 33 BN-106 538 42 BN-R-4 505 33 BN-107 535 42 BN-R-4 505 33 BN-108 539 45 BN-R-4 505 33 BN-109 538 44 BN-R-4 505 33 BN-110 539 42 BN-R-4 505 33 BN-111 539 43 BN-R-4 505 33 BN-112 539 42 BN-R-4 505 33 BN-113 526 42 BN-R-4 505 33 BN-114 525 43 BN-R-4 505 33 BN-115 526 42 BN-R-4 505 33 BN-116 526 43 BN-R-4 505 33 BN-117 525 43 BN-R-4 505 33 BN-118 526 43 BN-R-4 505 33 BN-119 527 44 BN-R-4 505 33 BN-120 526 42 BN-R-4 505 33 BN-121 526 43 BN-R-4 505 33 BN-122 527 43 BN-R-4 505 33 BN-123 524 44 BN-R-4 505 33 BN-124 527 42 BN-R-4 505 33 BN-125 528 44 BN-R-4 505 33 BN-126 528 43 BN-R-4 505 33 BN-127 528 44 BN-R-4 505 33 BN-128 529 45 BN-R-4 505 33 BN-129 563 53 BN-R-5 541 42 BN-130 564 53 BN-R-5 541 42 BN-131 564 54 BN-R-5 541 42 BN-132 565 50 BN-R-5 541 42 BN-133 565 51 BN-R-5 541 42 BN-134 566 52 BN-R-5 541 42 BN-135 564 53 BN-R-5 541 42 BN-136 565 51 BN-R-5 541 42 BN-137 566 53 BN-R-5 541 42 BN-138 565 51 BN-R-5 541 42 BN-139 564 52 BN-R-5 541 42 BN-140 566 50 BN-R-5 541 42 BN-141 567 51 BN-R-5 541 42 BN-142 566 52 BN-R-5 541 42 BN-143 567 51 BN-R-5 541 42 BN-144 566 52 BN-R-5 541 42 BN-145 554 52 BN-R-5 541 42 BN-146 555 52 BN-R-5 541 42 BN-147 554 51 BN-R-5 541 42 BN-148 555 52 BN-R-5 541 42 BN-149 555 54 BN-R-5 541 42 BN-150 556 52 BN-R-5 541 42 BN-151 553 52 BN-R-5 541 42 BN-152 556 53 BN-R-5 541 42 BN-153 556 54 BN-R-5 541 42 BN-154 557 52 BN-R-5 541 42 BN-155 554 53 BN-R-5 541 42 BN-156 557 53 BN-R-5 541 42 BN-157 556 54 BN-R-5 541 42 BN-158 556 52 BN-R-5 541 42 BN-159 557 53 BN-R-5 541 42 BN-160 557 52 BN-R-5 541 42 BN-161 630 54 BN-R-6 570 43 BN-162 629 55 BN-R-6 570 43 BN-163 629 56 BN-R-6 570 43 BN-164 629 56 BN-R-6 570 43 BN-165 628 55 BN-R-6 570 43 BN-166 630 56 BN-R-6 570 43 BN-167 628 54 BN-R-6 570 43 BN-168 629 55 BN-R-6 570 43 BN-169 630 54 BN-R-6 570 43 BN-170 629 53 BN-R-6 570 43 BN-171 630 55 BN-R-6 570 43 BN-172 631 54 BN-R-6 570 43 BN-173 630 56 BN-R-6 570 43 BN-174 630 55 BN-R-6 570 43 BN-175 631 57 BN-R-6 570 43 BN-176 630 55 BN-R-6 570 43 BN-177 619 56 BN-R-6 570 43 BN-178 619 54 BN-R-6 570 43 BN-179 619 55 BN-R-6 570 43 BN-180 620 53 BN-R-6 570 43 BN-181 621 54 BN-R-6 570 43 BN-182 620 55 BN-R-6 570 43 BN-183 621 53 BN-R-6 570 43 BN-184 621 54 BN-R-6 570 43 BN-185 620 53 BN-R-6 570 43 BN-186 622 53 BN-R-6 570 43 BN-187 621 55 BN-R-6 570 43 BN-188 621 56 BN-R-6 570 43 BN-189 622 54 BN-R-6 570 43 BN-190 622 55 BN-R-6 570 43 BN-191 621 53 BN-R-6 570 43 BN-192 622 54 BN-R-6 570 43 BN-193 496 38 BN-R-1 487 37 BN-194 497 39 BN-R-1 487 37 BN-195 497 40 BN-R-1 487 37 BN-196 498 38 BN-R-1 487 37 BN-197 498 39 BN-R-1 487 37 BN-198 499 39 BN-R-1 487 37 BN-199 498 40 BN-R-1 487 37 BN-200 499 37 BN-R-1 487 37 BN-201 497 38 BN-R-1 487 37 BN-202 497 38 BN-R-1 487 37 BN-203 498 37 BN-R-1 487 37 BN-204 498 39 BN-R-1 487 37 BN-205 497 41 BN-R-1 487 37 BN-206 498 40 BN-R-1 487 37 BN-207 498 42 BN-R-1 487 37 BN-208 498 38 BN-R-1 487 37 BN-209 497 41 BN-R-1 487 37 BN-210 499 43 BN-R-1 487 37 BN-211 499 43 BN-R-1 487 37 BN-212 497 41 BN-R-1 487 37 BN-213 498 42 BN-R-1 487 37 BN-214 499 43 BN-R-1 487 37 BN-215 498 42 BN-R-1 487 37 BN-216 499 44 BN-R-1 487 37 BN-217 499 43 BN-R-1 487 37 BN-218 498 44 BN-R-1 487 37 BN-219 499 42 BN-R-1 487 37 BN-220 499 45 BN-R-1 487 37 BN-221 498 43 BN-R-1 487 37 BN-222 498 46 BN-R-1 487 37 BN-223 499 45 BN-R-1 487 37 BN-224 499 43 BN-R-1 487 37 BN-225 501 45 BN-R-1 487 37 BN-226 501 43 BN-R-1 487 37 BN-227 502 42 BN-R-1 487 37 BN-228 502 44 BN-R-1 487 37 BN-229 502 45 BN-R-1 487 37 BN-230 501 43 BN-R-1 487 37 BN-231 502 43 BN-R-1 487 37 BN-232 502 44 BN-R-1 487 37 BN-233 502 42 BN-R-1 487 37 BN-234 501 42 BN-R-1 487 37 BN-235 501 43 BN-R-1 487 37 BN-236 502 44 BN-R-1 487 37 BN-237 502 42 BN-R-1 487 37 BN-238 502 42 BN-R-1 487 37 BN-239 503 44 BN-R-1 487 37 BN-240 501 42 BN-R-1 487 37 BN-241 502 43 BN-R-1 487 37 BN-242 502 42 BN-R-1 487 37 BN-243 503 44 BN-R-1 487 37 BN-244 502 43 BN-R-1 487 37 BN-245 502 42 BN-R-1 487 37 BN-246 503 41 BN-R-1 487 37 BN-247 504 40 BN-R-1 487 37 BN-248 502 43 BN-R-1 487 37 BN-249 503 42 BN-R-1 487 37 BN-250 503 44 BN-R-1 487 37 BN-251 504 43 BN-R-1 487 37 BN-252 503 44 BN-R-1 487 37 BN-253 503 42 BN-R-1 487 37 BN-254 504 44 BN-R-1 487 37 BN-255 503 43 BN-R-1 487 37 BN-256 504 42 BN-R-1 487 37 BN-257 505 44 BN-R-2 496 36 BN-258 505 42 BN-R-2 496 36 BN-259 506 43 BN-R-2 496 36 BN-260 506 42 BN-R-2 496 36 BN-261 507 43 BN-R-2 496 36 BN-262 508 42 BN-R-2 496 36 BN-263 507 44 BN-R-2 496 36 BN-264 508 43 BN-R-2 496 36 BN-265 508 43 BN-R-2 496 36 BN-266 508 42 BN-R-2 496 36 BN-267 507 43 BN-R-2 496 36 BN-268 509 44 BN-R-2 496 36 BN-269 508 43 BN-R-2 496 36 BN-270 507 42 BN-R-2 496 36 BN-271 507 43 BN-R-2 496 36 BN-272 506 42 BN-R-2 496 36 BN-273 508 44 BN-R-2 496 36 BN-274 508 43 BN-R-2 496 36 BN-275 507 42 BN-R-2 496 36 BN-276 506 43 BN-R-2 496 36 BN-277 508 43 BN-R-2 496 36 BN-278 509 42 BN-R-2 496 36 BN-279 509 44 BN-R-2 496 36 BN-280 508 42 BN-R-2 496 36 BN-281 508 43 BN-R-2 496 36 BN-282 509 44 BN-R-2 496 36 BN-283 509 43 BN-R-2 496 36 BN-284 508 42 BN-R-2 496 36 BN-285 508 43 BN-R-2 496 36 BN-286 509 41 BN-R-2 496 36 BN-287 509 43 BN-R-2 496 36 BN-288 509 43 BN-R-2 496 36 BN-289 506 44 BN-R-2 496 36 BN-290 506 43 BN-R-2 496 36 BN-291 507 45 BN-R-2 496 36 BN-292 508 43 BN-R-2 496 36 BN-293 510 44 BN-R-2 496 36 BN-294 510 43 BN-R-2 496 36 BN-295 509 44 BN-R-2 496 36 BN-296 509 45 BN-R-2 496 36 BN-297 510 43 BN-R-2 496 36 BN-298 509 42 BN-R-2 496 36 BN-299 510 43 BN-R-2 496 36 BN-300 510 42 BN-R-2 496 36 BN-301 511 42 BN-R-2 496 36 BN-302 510 45 BN-R-2 496 36 BN-303 509 44 BN-R-2 496 36 BN-304 509 42 BN-R-2 496 36 BN-305 508 45 BN-R-2 496 36 BN-306 511 42 BN-R-2 496 36 BN-307 510 43 BN-R-2 496 36 BN-308 509 44 BN-R-2 496 36 BN-309 510 43 BN-R-2 496 36 BN-310 511 42 BN-R-2 496 36 BN-311 512 44 BN-R-2 496 36 BN-312 511 44 BN-R-2 496 36 BN-313 510 42 BN-R-2 496 36 BN-314 512 42 BN-R-2 496 36 BN-315 511 44 BN-R-2 496 36 BN-316 511 42 BN-R-2 496 36 BN-317 512 44 BN-R-2 496 36 BN-318 510 42 BN-R-2 496 36 BN-319 511 43 BN-R-2 496 36 BN-320 511 43 BN-R-2 496 36 BN-321 503 43 BN-R-3 493 35 BN-322 502 42 BN-R-3 493 35 BN-323 503 41 BN-R-3 493 35 BN-324 504 42 BN-R-3 493 35 BN-325 503 43 BN-R-3 493 35 BN-326 504 42 BN-R-3 493 35 BN-327 503 43 BN-R-3 493 35 BN-328 505 42 BN-R-3 493 35 BN-329 504 45 BN-R-3 493 35 BN-330 505 44 BN-R-3 493 35 BN-331 506 42 BN-R-3 493 35 BN-332 504 43 BN-R-3 493 35 BN-333 506 44 BN-R-3 493 35 BN-334 505 43 BN-R-3 493 35 BN-335 505 45 BN-R-3 493 35 BN-336 503 42 BN-R-3 493 35 BN-337 506 43 BN-R-3 493 35 BN-338 506 42 BN-R-3 493 35 BN-339 503 43 BN-R-3 493 35 BN-340 505 43 BN-R-3 493 35 BN-341 504 44 BN-R-3 493 35 BN-342 506 43 BN-R-3 493 35 BN-343 505 42 BN-R-3 493 35 BN-344 506 44 BN-R-3 493 35 BN-345 505 42 BN-R-3 493 35 BN-346 505 41 BN-R-3 493 35 BN-347 506 43 BN-R-3 493 35 BN-348 506 43 BN-R-3 493 35 BN-349 505 42 BN-R-3 493 35 BN-350 506 44 BN-R-3 493 35 BN-351 506 45 BN-R-3 493 35 BN-352 506 44 BN-R-3 493 35 BN-353 508 44 BN-R-3 493 35 BN-354 507 43 BN-R-3 493 35 BN-355 507 45 BN-R-3 493 35 BN-356 508 42 BN-R-3 493 35 BN-357 508 44 BN-R-3 493 35 BN-358 507 43 BN-R-3 493 35 BN-359 507 42 BN-R-3 493 35 BN-360 508 44 BN-R-3 493 35 BN-361 508 42 BN-R-3 493 35 BN-362 508 43 BN-R-3 493 35 BN-363 509 42 BN-R-3 493 35 BN-364 508 43 BN-R-3 493 35 BN-365 507 44 BN-R-3 493 35 BN-366 508 43 BN-R-3 493 35 BN-367 507 44 BN-R-3 493 35 BN-368 506 42 BN-R-3 493 35 BN-369 508 43 BN-R-3 493 35 BN-370 507 42 BN-R-3 493 35 BN-371 508 42 BN-R-3 493 35 BN-372 506 43 BN-R-3 493 35 BN-373 509 44 BN-R-3 493 35 BN-374 509 42 BN-R-3 493 35 BN-375 508 43 BN-R-3 493 35 BN-376 508 42 BN-R-3 493 35 BN-377 509 45 BN-R-3 493 35 BN-378 508 44 BN-R-3 493 35 BN-379 508 42 BN-R-3 493 35 BN-380 509 43 BN-R-3 493 35 BN-381 509 42 BN-R-3 493 35 BN-382 508 43 BN-R-3 493 35 BN-383 509 45 BN-R-3 493 35 BN-384 509 45 BN-R-3 493 35 BN-385 516 42 BN-R-4 505 33 BN-386 517 43 BN-R-4 505 33 BN-387 516 42 BN-R-4 505 33 BN-388 518 43 BN-R-4 505 33 BN-389 517 43 BN-R-4 505 33 BN-390 516 44 BN-R-4 505 33 BN-391 517 42 BN-R-4 505 33 BN-392 517 45 BN-R-4 505 33 BN-393 517 44 BN-R-4 505 33 BN-394 518 43 BN-R-4 505 33 BN-395 517 42 BN-R-4 505 33 BN-396 518 45 BN-R-4 505 33 BN-397 519 44 BN-R-4 505 33 BN-398 518 43 BN-R-4 505 33 BN-399 518 42 BN-R-4 505 33 BN-400 516 43 BN-R-4 505 33 BN-401 518 44 BN-R-4 505 33 BN-402 517 43 BN-R-4 505 33 BN-403 518 43 BN-R-4 505 33 BN-404 515 45 BN-R-4 505 33 BN-405 518 43 BN-R-4 505 33 BN-406 518 44 BN-R-4 505 33 BN-407 519 43 BN-R-4 505 33 BN-408 518 43 BN-R-4 505 33 BN-409 519 42 BN-R-4 505 33 BN-410 519 42 BN-R-4 505 33 BN-411 518 43 BN-R-4 505 33 BN-412 519 43 BN-R-4 505 33 BN-413 518 44 BN-R-4 505 33 BN-414 518 42 BN-R-4 505 33 BN-415 519 42 BN-R-4 505 33 BN-416 519 44 BN-R-4 505 33 BN-417 520 43 BN-R-4 505 33 BN-418 520 42 BN-R-4 505 33 BN-419 520 43 BN-R-4 505 33 BN-420 521 42 BN-R-4 505 33 BN-421 521 44 BN-R-4 505 33 BN-422 520 43 BN-R-4 505 33 BN-423 520 43 BN-R-4 505 33 BN-424 521 42 BN-R-4 505 33 BN-425 520 43 BN-R-4 505 33 BN-426 520 42 BN-R-4 505 33 BN-427 521 44 BN-R-4 505 33 BN-428 520 45 BN-R-4 505 33 BN-429 521 43 BN-R-4 505 33 BN-430 520 44 BN-R-4 505 33 BN-431 521 43 BN-R-4 505 33 BN-432 521 43 BN-R-4 505 33 BN-433 520 44 BN-R-4 505 33 BN-434 520 43 BN-R-4 505 33 BN-435 519 42 BN-R-4 505 33 BN-436 520 43 BN-R-4 505 33 BN-437 520 43 BN-R-4 505 33 BN-438 522 45 BN-R-4 505 33 BN-439 521 43 BN-R-4 505 33 BN-440 522 42 BN-R-4 505 33 BN-441 522 43 BN-R-4 505 33 BN-442 521 45 BN-R-4 505 33 BN-443 521 44 BN-R-4 505 33 BN-444 520 43 BN-R-4 505 33 BN-445 521 44 BN-R-4 505 33 BN-446 522 43 BN-R-4 505 33 BN-447 521 44 BN-R-4 505 33 BN-448 522 45 BN-R-4 505 33 BN-449 549 53 BN-R-5 541 42 BN-450 548 52 BN-R-5 541 42 BN-451 550 51 BN-R-5 541 42 BN-452 551 52 BN-R-5 541 42 BN-453 551 53 BN-R-5 541 42 BN-454 552 52 BN-R-5 541 42 BN-455 551 52 BN-R-5 541 42 BN-456 552 53 BN-R-5 541 42 BN-457 551 52 BN-R-5 541 42 BN-458 551 53 BN-R-5 541 42 BN-459 550 53 BN-R-5 541 42 BN-460 552 52 BN-R-5 541 42 BN-461 551 53 BN-R-5 541 42 BN-462 552 52 BN-R-5 541 42 BN-463 551 54 BN-R-5 541 42 BN-464 552 52 BN-R-5 541 42 BN-465 551 53 BN-R-5 541 42 BN-466 550 51 BN-R-5 541 42 BN-467 552 52 BN-R-5 541 42 BN-468 551 54 BN-R-5 541 42 BN-469 552 51 BN-R-5 541 42 BN-470 551 53 BN-R-5 541 42 BN-471 551 52 BN-R-5 541 42 BN-472 552 54 BN-R-5 541 42 BN-473 552 53 BN-R-5 541 42 BN-474 551 52 BN-R-5 541 42 BN-475 552 54 BN-R-5 541 42 BN-476 552 54 BN-R-5 541 42 BN-477 552 52 BN-R-5 541 42 BN-478 551 53 BN-R-5 541 42 BN-479 552 51 BN-R-5 541 42 BN-480 552 52 BN-R-5 541 42 BN-481 554 53 BN-R-5 541 42 BN-482 553 52 BN-R-5 541 42 BN-483 554 53 BN-R-5 541 42 BN-484 556 52 BN-R-5 541 42 BN-485 556 53 BN-R-5 541 42 BN-486 557 54 BN-R-5 541 42 BN-487 557 53 BN-R-5 541 42 BN-488 556 52 BN-R-5 541 42 BN-489 556 54 BN-R-5 541 42 BN-490 557 52 BN-R-5 541 42 BN-491 556 53 BN-R-5 541 42 BN-492 556 54 BN-R-5 541 42 BN-493 557 53 BN-R-5 541 42 BN-494 558 53 BN-R-5 541 42 BN-495 557 54 BN-R-5 541 42 BN-496 556 52 BN-R-5 541 42 BN-497 557 52 BN-R-5 541 42 BN-498 557 53 BN-R-5 541 42 BN-499 558 52 BN-R-5 541 42 BN-500 556 53 BN-R-5 541 42 BN-501 557 55 BN-R-5 541 42 BN-502 557 53 BN-R-5 541 42 BN-503 558 53 BN-R-5 541 42 BN-504 557 54 BN-R-5 541 42 BN-505 557 52 BN-R-5 541 42 BN-506 558 52 BN-R-5 541 42 BN-507 558 53 BN-R-5 541 42 BN-508 559 51 BN-R-5 541 42 BN-509 558 52 BN-R-5 541 42 BN-510 558 54 BN-R-5 541 42 BN-511 557 53 BN-R-5 541 42 BN-512 559 53 BN-R-5 541 42 BN-513 580 55 BN-R-6 570 43 BN-514 579 54 BN-R-6 570 43 BN-515 580 54 BN-R-6 570 43 BN-516 582 53 BN-R-6 570 43 BN-517 581 55 BN-R-6 570 43 BN-518 581 53 BN-R-6 570 43 BN-519 582 52 BN-R-6 570 43 BN-520 582 53 BN-R-6 570 43 BN-521 581 54 BN-R-6 570 43 BN-522 581 55 BN-R-6 570 43 BN-523 582 54 BN-R-6 570 43 BN-524 583 53 BN-R-6 570 43 BN-525 582 54 BN-R-6 570 43 BN-526 581 55 BN-R-6 570 43 BN-527 581 55 BN-R-6 570 43 BN-528 580 54 BN-R-6 570 43 BN-529 581 53 BN-R-6 570 43 BN-530 582 52 BN-R-6 570 43 BN-531 582 54 BN-R-6 570 43 BN-532 580 55 BN-R-6 570 43 BN-533 582 55 BN-R-6 570 43 BN-534 582 56 BN-R-6 570 43 BN-535 581 54 BN-R-6 570 43 BN-536 582 54 BN-R-6 570 43 BN-537 583 52 BN-R-6 570 43 BN-538 582 55 BN-R-6 570 43 BN-539 582 54 BN-R-6 570 43 BN-540 582 56 BN-R-6 570 43 BN-541 583 53 BN-R-6 570 43 BN-542 583 54 BN-R-6 570 43 BN-543 582 55 BN-R-6 570 43 BN-544 582 53 BN-R-6 570 43 BN-545 584 54 BN-R-6 570 43 BN-546 583 53 BN-R-6 570 43 BN-547 583 55 BN-R-6 570 43 BN-548 585 55 BN-R-6 570 43 BN-549 585 56 BN-R-6 570 43 BN-550 585 55 BN-R-6 570 43 BN-551 586 54 BN-R-6 570 43 BN-552 586 53 BN-R-6 570 43 BN-553 585 55 BN-R-6 570 43 BN-554 586 56 BN-R-6 570 43 BN-555 585 56 BN-R-6 570 43 BN-556 586 57 BN-R-6 570 43 BN-557 585 55 BN-R-6 570 43 BN-558 586 54 BN-R-6 570 43 BN-559 585 56 BN-R-6 570 43 BN-560 584 55 BN-R-6 570 43 BN-561 586 54 BN-R-6 570 43 BN-562 586 55 BN-R-6 570 43 BN-563 586 53 BN-R-6 570 43 BN-564 584 54 BN-R-6 570 43 BN-565 585 57 BN-R-6 570 43 BN-566 586 56 BN-R-6 570 43 BN-567 586 54 BN-R-6 570 43 BN-568 584 55 BN-R-6 570 43 BN-569 586 56 BN-R-6 570 43 BN-570 586 55 BN-R-6 570 43 BN-571 585 54 BN-R-6 570 43 BN-572 585 56 BN-R-6 570 43 BN-573 586 55 BN-R-6 570 43 BN-574 586 55 BN-R-6 570 43 BN-575 587 57 BN-R-6 570 43 BN-576 587 55 BN-R-6 570 43 BN-577 630 54 BN-R-7 573 45 BN-578 628 53 BN-R-7 573 45 BN-579 628 52 BN-R-7 573 45 BN-580 629 51 BN-R-7 573 45 BN-581 629 49 BN-R-7 573 45 BN-582 626 50 BN-R-7 573 45 BN-583 627 49 BN-R-7 573 45 BN-584 627 48 BN-R-7 573 45

The molecular structures of some materials involved in the embodiments of electroluminescent devices are as follows:

The following examples of electroluminescent devices are prepared by using the materials of the present invention, and the specific device preparation process is as follows: (1) Substrate processing: transparent ITO glass is used as the substrate material for preparing the device, and then ultrasonically treated with 5% ITO lotion for 30 minutes. min, followed by ultrasonic washing with distilled water (2 times), acetone (2 times), and isopropanol (2 times) in turn, and finally the ITO glass was stored in isopropanol. Before each use, carefully wipe the surface of the ITO glass with an acetone cotton ball and an isopropyl alcohol cotton ball, rinse with isopropyl alcohol, dry it, and then treat it with plasma for 5 min for use. The fabrication of the device is accomplished by a combination of spin coating and vacuum evaporation. (2) Preparation of hole injection layer and hole transport layer: First, spin-coat a layer of PEDOT:PSS (poly3,4-ethylenedioxythiophene):polystyrene sulfonate with a thickness of 20 nm on the surface of ITO. The material was purchased from Heraeus, Germany and used directly) as a hole injection layer, and then a 50 nm-thick Poly-HTL was spin-coated on the hole injection layer as a hole transport layer, and then the hole injection layer and hole transport layer were applied. The layered ITO glass was annealed at 200°C for 30 minutes in a nitrogen-protected glove box (to cross-link the Poly-HTL ). (3) 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. The light-emitting layer was prepared by the method, and the thickness of the light-emitting layer was 50 nm. (4) Preparation of electron transport layer, electron injection layer and metal electrode: The electron transport layer, electron injection layer and metal electrode are prepared by evaporation process. When the vacuum degree of the vacuum evaporation system reaches below 5×10 ^-4 Pa Evaporation, 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 (for the specific device structure, see the following effect example). Among them, the deposition rate of organic materials is 0.5 Å/s, that of LiF is 0.1 Å/s, and that of Al is 5 Å/s. 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 according to the Lambertian distribution of luminescence, which is calculated from the current density, brightness and electro-spectrum combined with the visual function.

Effect Example 2 In the organic electroluminescent device (structure shown in Figure 1) in Effect Example 2, PEDOT:PSS is used as a hole injection layer, Poly-HTL is used as a hole transport layer, and in the light emitting layer H1-48 was used as host material, BN-1 to BN-584 were used as doped light-emitting materials (the doping concentration was 3wt%), TmPyPB was used as electron transport material, LiF was used as electron injection layer, and Al was used as metal Cathode use. Effect Example The structure of the organic electroluminescent device is [ITO/PEDOT:PSS (20 nm)/Poly-HTL(50 nm)/ /H1-48 +3wt%BN-n/TmPyPB(50 nm)/LiF(1 nm) )/Al(100 nm)]. where n = 1-584. The results of the effect examples are shown in Table 3. The implementation data of electroluminescence device effects listed in Table 3 prove that the luminescent material provided by the present invention 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.

[Table 3] Main parameters of electroluminescence performance of BN-n (n = 1-584). Compound (BN-n) Electroluminescence spectrum peak position (nm) Electroluminescence spectrum half width (nm) Electroluminescence External Quantum Efficiency (%) BN-1 519 41 26.2 BN-2 520 41 25.8 BN-3 520 42 26.1 BN-4 521 42 25.7 BN-5 520 43 25.6 BN-6 519 42 25.9 BN-7 521 41 25.8 BN-8 520 43 26.0 BN-9 520 43 25.7 BN-10 519 42 25.5 BN-11 521 43 25.4 BN-12 520 43 25.5 BN-13 522 44 25.9 BN-14 521 44 25.8 BN-15 520 43 26.3 BN-16 522 42 25.9 BN-17 509 43 25.7 BN-18 510 42 25.6 BN-19 510 42 25.9 BN-20 509 44 25.6 BN-21 510 44 25.6 BN-22 509 43 26.2 BN-23 509 42 25.8 BN-24 510 44 26.1 BN-25 509 44 25.7 BN-26 510 43 25.6 BN-27 511 45 25.5 BN-28 510 43 25.6 BN-29 511 42 25.7 BN-30 511 44 25.8 BN-31 511 43 25.6 BN-32 512 42 25.9 BN-33 530 42 26.2 BN-34 530 44 25.6 BN-35 529 43 25.7 BN-36 531 42 25.8 BN-37 530 43 25.6 BN-38 531 44 25.8 BN-39 530 43 25.6 BN-40 531 42 25.6 BN-41 530 43 25.7 BN-42 530 43 25.6 BN-43 529 44 25.8 BN-44 531 42 26.3 BN-45 530 43 25.6 BN-46 532 43 25.5 BN-47 531 43 26.6 BN-48 532 43 25.9 BN-49 518 42 25.8 BN-50 518 43 25.5 BN-51 519 42 25.7 BN-52 520 43 26.0 BN-53 520 44 25.6 BN-54 519 41 25.7 BN-55 519 43 25.5 BN-56 520 43 25.7 BN-57 521 44 25.6 BN-58 520 42 25.8 BN-59 518 43 25.7 BN-60 520 44 26.2 BN-61 520 41 25.8 BN-62 519 42 25.9 BN-63 522 43 26.0 BN-64 521 41 25.6 BN-65 526 43 25.6 BN-66 526 43 26.0 BN-67 526 41 25.6 BN-68 527 41 25.5 BN-69 526 42 25.5 BN-70 527 43 25.8 BN-71 526 44 25.7 BN-72 525 42 25.6 BN-73 525 41 25.8 BN-74 526 42 25.8 BN-75 527 42 25.9 BN-76 527 43 25.6 BN-77 528 42 25.7 BN-78 527 43 25.5 BN-79 528 42 25.4 BN-80 527 43 25.6 BN-81 516 42 25.5 BN-82 515 44 25.7 BN-83 516 43 25.6 BN-84 515 43 25.6 BN-85 516 42 25.7 BN-86 516 41 25.6 BN-87 517 43 26.2 BN-88 516 42 25.8 BN-89 517 43 25.7 BN-90 517 44 25.7 BN-91 517 42 25.5 BN-92 516 42 25.7 BN-93 516 41 25.6 BN-94 517 43 25.5 BN-95 518 44 25.8 BN-96 517 43 26.2 BN-97 537 42 25.9 BN-98 538 41 25.4 BN-99 538 44 25.6 BN-100 539 42 25.9 BN-101 538 43 25.7 BN-102 539 43 25.7 BN-103 538 42 25.6 BN-104 537 45 25.8 BN-105 539 43 25.6 BN-106 538 43 25.7 BN-107 536 42 25.5 BN-108 538 44 25.6 BN-109 539 42 25.8 BN-110 538 43 25.9 BN-111 538 42 25.5 BN-112 539 44 26.2 BN-113 526 43 25.9 BN-114 526 42 25.7 BN-115 525 41 25.6 BN-116 526 42 25.6 BN-117 526 44 25.7 BN-118 527 43 25.6 BN-119 527 42 25.5 BN-120 527 43 25.5 BN-121 526 44 25.7 BN-122 526 43 25.7 BN-123 524 43 25.5 BN-124 526 43 25.9 BN-125 527 42 25.7 BN-126 527 44 25.6 BN-127 528 42 25.5 BN-128 529 44 25.5 BN-129 563 52 25.7 BN-130 563 54 26.0 BN-131 564 53 25.5 BN-132 565 52 25.6 BN-133 564 51 25.5 BN-134 565 53 25.8 BN-135 565 54 25.6 BN-136 566 52 25.6 BN-137 565 51 25.7 BN-138 566 53 25.5 BN-139 564 52 25.7 BN-140 566 52 25.7 BN-141 566 51 25.9 BN-142 567 53 25.5 BN-143 566 54 25.8 BN-144 567 54 25.7 BN-145 555 51 25.9 BN-146 554 52 25.6 BN-147 555 52 25.8 BN-148 556 53 25.5 BN-149 555 54 25.6 BN-150 556 53 25.8 BN-151 554 52 25.5 BN-152 556 52 25.6 BN-153 555 53 25.9 BN-154 556 53 25.5 BN-155 555 54 25.7 BN-156 556 54 26.0 BN-157 557 53 25.8 BN-158 556 53 25.6 BN-159 556 53 25.5 BN-160 557 54 25.6 BN-161 630 56 25.2 BN-162 630 55 25.3 BN-163 629 55 25.1 BN-164 630 56 25.2 BN-165 628 56 25.5 BN-166 629 57 25.3 BN-167 629 55 25.1 BN-168 630 56 25.2 BN-169 629 53 25.0 BN-170 630 55 25.2 BN-171 631 53 25.4 BN-172 630 54 25.1 BN-173 631 55 25.2 BN-174 630 56 25.4 BN-175 630 55 25.2 BN-176 631 56 25.3 BN-177 619 55 25.4 BN-178 620 55 25.5 BN-179 619 56 25.3 BN-180 620 54 25.1 BN-181 620 55 25.1 BN-182 621 54 25.2 BN-183 620 55 25.2 BN-184 621 53 25.1 BN-185 621 56 25.4 BN-186 622 55 25.1 BN-187 620 55 25.3 BN-188 622 54 25.5 BN-189 622 55 25.1 BN-190 621 55 25.2 BN-191 621 56 25.3 BN-192 622 53 25.5 BN-193 496 37 25.7 BN-194 496 38 25.8 BN-195 497 40 25.6 BN-196 497 39 25.5 BN-197 498 40 25.6 BN-198 498 38 25.7 BN-199 499 39 26.2 BN-200 498 37 25.7 BN-201 497 37 25.5 BN-202 498 39 25.7 BN-203 497 40 25.6 BN-204 498 39 25.5 BN-205 498 40 25.6 BN-206 499 38 25.4 BN-207 498 43 25.5 BN-208 497 40 25.3 BN-209 498 41 25.4 BN-210 498 42 25.7 BN-211 499 43 25.6 BN-212 498 42 25.7 BN-213 499 43 25.8 BN-214 498 44 25.5 BN-215 497 43 25.5 BN-216 498 44 25.8 BN-217 498 42 25.7 BN-218 499 43 25.6 BN-219 498 42 25.5 BN-220 497 44 25.7 BN-221 498 42 25.6 BN-222 499 44 25.6 BN-223 498 44 25.7 BN-224 499 45 25.6 BN-225 502 43 25.5 BN-226 501 43 25.7 BN-227 501 44 25.5 BN-228 501 43 25.6 BN-229 502 42 25.7 BN-230 502 43 25.6 BN-231 501 42 25.8 BN-232 502 43 25.5 BN-233 501 43 25.7 BN-234 502 42 25.5 BN-235 501 44 25.8 BN-236 501 43 25.5 BN-237 502 43 25.9 BN-238 501 42 25.7 BN-239 502 43 26.1 BN-240 502 42 25.8 BN-241 503 42 25.5 BN-242 502 43 25.7 BN-243 502 44 25.6 BN-244 503 44 25.8 BN-245 502 43 26.2 BN-246 502 42 25.7 BN-247 503 42 25.6 BN-248 503 43 25.7 BN-249 502 43 25.8 BN-250 503 44 25.5 BN-251 503 42 25.6 BN-252 504 42 25.5 BN-253 503 43 25.6 BN-254 503 43 25.5 BN-255 504 42 25.6 BN-256 504 43 25.5 BN-257 505 43 25.8 BN-258 506 44 25.6 BN-259 505 43 25.5 BN-260 506 44 25.5 BN-261 506 41 25.7 BN-262 507 41 25.6 BN-263 508 42 25.7 BN-264 507 43 25.6 BN-265 508 44 25.5 BN-266 507 43 25.6 BN-267 508 42 25.7 BN-268 508 43 25.6 BN-269 507 45 25.7 BN-270 508 42 25.8 BN-271 507 42 25.6 BN-272 507 44 25.7 BN-273 509 43 25.6 BN-274 508 43 26.1 BN-275 508 44 25.7 BN-276 506 42 25.7 BN-277 508 43 25.8 BN-278 508 43 25.6 BN-279 509 42 25.5 BN-280 509 43 25.5 BN-281 508 43 25.7 BN-282 508 42 25.8 BN-283 509 44 25.6 BN-284 509 43 26.1 BN-285 509 43 25.5 BN-286 508 42 25.5 BN-287 508 42 26.0 BN-288 509 44 25.9 BN-289 507 42 25.5 BN-290 506 42 25.6 BN-291 506 45 25.6 BN-292 507 44 25.8 BN-293 509 45 25.7 BN-294 510 44 25.8 BN-295 510 42 25.5 BN-296 509 43 25.7 BN-297 509 44 25.9 BN-298 510 43 25.7 BN-299 511 42 25.5 BN-300 511 44 25.6 BN-301 510 42 25.6 BN-302 509 43 25.9 BN-303 509 44 25.7 BN-304 510 42 25.6 BN-305 509 43 25.7 BN-306 510 44 25.5 BN-307 511 43 25.5 BN-308 509 43 25.8 BN-309 511 44 25.6 BN-310 512 43 25.6 BN-311 511 42 25.5 BN-312 511 44 25.6 BN-313 511 43 25.7 BN-314 512 43 25.5 BN-315 512 42 25.6 BN-316 511 44 26.2 BN-317 511 43 25.9 BN-318 511 43 25.6 BN-319 512 42 25.5 BN-320 512 43 25.6 BN-321 503 44 25.6 BN-322 502 43 25.8 BN-323 502 42 25.9 BN-324 503 43 25.6 BN-325 504 42 25.6 BN-326 503 44 25.7 BN-327 504 43 25.5 BN-328 505 43 25.4 BN-329 505 42 25.6 BN-330 506 43 25.7 BN-331 505 42 25.5 BN-332 505 44 25.7 BN-333 506 43 26.0 BN-334 506 43 25.8 BN-335 505 44 25.6 BN-336 504 44 25.7 BN-337 505 43 25.9 BN-338 505 44 25.7 BN-339 504 42 25.5 BN-340 505 43 25.7 BN-341 505 43 25.6 BN-342 506 43 25.5 BN-343 506 44 25.5 BN-344 505 43 25.7 BN-345 506 42 25.4 BN-346 506 43 25.5 BN-347 505 42 25.8 BN-348 506 44 25.5 BN-349 505 43 25.6 BN-350 505 43 25.5 BN-351 505 43 25.8 BN-352 506 42 25.6 BN-353 507 45 25.6 BN-354 508 43 25.7 BN-355 507 44 25.8 BN-356 508 43 25.6 BN-357 507 43 25.9 BN-358 508 45 25.5 BN-359 508 43 25.6 BN-360 507 42 25.6 BN-361 508 43 25.9 BN-362 507 43 25.4 BN-363 508 44 25.5 BN-364 508 45 25.6 BN-365 508 43 25.7 BN-366 507 42 25.5 BN-367 508 43 25.6 BN-368 507 43 25.7 BN-369 508 44 25.7 BN-370 508 42 25.4 BN-371 507 43 25.6 BN-372 507 43 25.7 BN-373 508 42 25.5 BN-374 508 44 25.5 BN-375 509 43 25.7 BN-376 508 43 25.5 BN-377 509 42 25.6 BN-378 509 43 25.8 BN-379 508 44 25.8 BN-380 508 44 25.7 BN-381 509 43 25.4 BN-382 509 43 25.7 BN-383 508 44 25.9 BN-384 509 43 25.6 BN-385 517 43 25.8 BN-386 516 42 25.5 BN-387 516 43 25.6 BN-388 517 43 25.4 BN-389 518 42 25.4 BN-390 517 41 25.8 BN-391 518 42 25.7 BN-392 517 44 25.6 BN-393 518 43 25.9 BN-394 517 44 25.7 BN-395 518 45 25.6 BN-396 517 44 25.7 BN-397 518 42 25.8 BN-398 518 43 25.6 BN-399 519 44 25.7 BN-400 517 42 25.5 BN-401 518 42 25.6 BN-402 518 42 25.7 BN-403 519 44 25.8 BN-404 515 43 25.9 BN-405 518 43 25.5 BN-406 519 42 25.6 BN-407 518 42 25.6 BN-408 518 43 25.8 BN-409 519 43 25.7 BN-410 518 42 25.6 BN-411 519 44 25.7 BN-412 519 42 25.5 BN-413 518 43 25.8 BN-414 519 44 25.9 BN-415 519 43 25.5 BN-416 518 44 25.6 BN-417 520 42 25.5 BN-418 520 43 26.2 BN-419 521 44 25.9 BN-420 520 42 25.8 BN-421 521 43 25.5 BN-422 521 42 25.5 BN-423 520 42 25.7 BN-424 520 44 26.2 BN-425 521 45 26.0 BN-426 521 43 25.8 BN-427 520 44 25.6 BN-428 521 43 25.7 BN-429 521 43 25.8 BN-430 520 42 25.6 BN-431 520 43 25.5 BN-432 521 44 25.6 BN-433 521 42 25.5 BN-434 520 42 25.7 BN-435 519 43 25.5 BN-436 521 44 25.6 BN-437 521 42 25.5 BN-438 522 42 25.5 BN-439 521 45 25.6 BN-440 521 44 25.7 BN-441 522 43 25.9 BN-442 522 43 25.9 BN-443 522 42 25.6 BN-444 521 42 25.7 BN-445 522 45 26.2 BN-446 521 44 26.3 BN-447 522 42 25.8 BN-448 522 43 25.9 BN-449 548 53 25.6 BN-450 549 54 25.7 BN-451 550 53 25.7 BN-452 551 52 25.6 BN-453 552 52 25.8 BN-454 552 53 25.6 BN-455 551 54 25.7 BN-456 551 53 25.8 BN-457 552 54 25.7 BN-458 551 52 25.6 BN-459 551 52 25.6 BN-460 552 54 25.6 BN-461 552 53 25.5 BN-462 551 54 25.7 BN-463 552 53 25.7 BN-464 552 52 25.5 BN-465 551 54 25.8 BN-466 551 52 25.6 BN-467 551 53 25.5 BN-468 552 52 25.7 BN-469 551 53 25.6 BN-470 551 53 25.9 BN-471 552 54 25.7 BN-472 551 54 25.8 BN-473 552 54 25.6 BN-474 552 53 26.2 BN-475 552 53 25.9 BN-476 551 52 25.7 BN-477 552 53 25.7 BN-478 552 53 25.5 BN-479 551 52 25.6 BN-480 552 54 25.5 BN-481 553 52 25.7 BN-482 554 53 25.6 BN-483 553 53 25.8 BN-484 556 54 25.5 BN-485 557 53 25.7 BN-486 556 52 25.6 BN-487 557 52 25.5 BN-488 557 52 25.5 BN-489 556 54 25.7 BN-490 556 52 25.6 BN-491 557 53 25.7 BN-492 557 54 25.5 BN-493 556 53 25.6 BN-494 557 53 25.8 BN-495 558 54 25.7 BN-496 557 52 25.5 BN-497 558 52 25.6 BN-498 557 54 25.5 BN-499 557 53 25.5 BN-500 556 54 25.7 BN-501 558 54 25.6 BN-502 557 52 25.5 BN-503 557 53 25.5 BN-504 557 53 25.8 BN-505 558 54 25.7 BN-506 557 53 25.6 BN-507 559 52 25.7 BN-508 558 53 25.5 BN-509 559 53 25.5 BN-510 558 52 25.8 BN-511 558 54 25.6 BN-512 559 53 25.5 BN-513 580 54 25.7 BN-514 580 55 25.5 BN-515 581 53 25.6 BN-516 582 54 25.8 BN-517 582 55 25.6 BN-518 582 54 25.5 BN-519 581 54 25.6 BN-520 582 55 25.9 BN-521 582 53 25.7 BN-522 581 54 25.7 BN-523 582 55 25.6 BN-524 582 53 26.1 BN-525 582 55 25.8 BN-526 583 54 25.5 BN-527 582 53 25.6 BN-528 581 54 25.6 BN-529 582 55 25.7 BN-530 583 54 25.8 BN-531 582 53 25.7 BN-532 581 55 25.6 BN-533 583 54 25.6 BN-534 583 56 25.7 BN-535 582 55 25.5 BN-536 582 54 25.8 BN-537 582 54 25.8 BN-538 583 53 25.6 BN-539 583 53 25.5 BN-540 582 55 25.6 BN-541 582 54 25.9 BN-542 582 55 25.7 BN-543 582 53 25.6 BN-544 583 55 25.5 BN-545 584 53 25.6 BN-546 584 55 25.6 BN-547 584 56 25.7 BN-548 585 55 25.6 BN-549 586 55 25.7 BN-550 585 54 25.6 BN-551 585 53 25.5 BN-552 586 53 25.6 BN-553 586 54 25.7 BN-554 585 55 25.5 BN-555 585 56 25.6 BN-556 585 56 25.7 BN-557 586 54 25.7 BN-558 585 55 25.6 BN-559 586 56 25.7 BN-560 585 54 25.5 BN-561 585 55 25.7 BN-562 586 56 25.6 BN-563 585 54 25.6 BN-564 584 53 25.8 BN-565 586 55 25.6 BN-566 585 55 25.7 BN-567 586 56 25.6 BN-568 585 54 25.8 BN-569 586 55 25.6 BN-570 585 55 25.5 BN-571 586 56 25.5 BN-572 586 57 25.6 BN-573 587 55 25.7 BN-574 586 55 25.8 BN-575 587 56 25.9 BN-576 587 56 26.1 BN-577 631 52 25.2 BN-578 629 51 25.1 BN-579 628 52 25.3 BN-580 629 50 25.2 BN-581 628 51 25.0 BN-582 626 49 25.1 BN-583 626 48 25.3 BN-584 627 49 25.2

Effect Example 3 In the organic electroluminescence device in Effect Example 3, in the organic electroluminescence device in Effect Example 2 (the structure is shown in Figure 1 ), PEDOT:PSS is used as a hole injection layer, Poly-HTL is used as a hole transport layer, a mixture of H1-33 and TRZ-1 is used as a host material in the light-emitting layer (the weight mixing ratio of H1-33 and TRZ-1 is 1:1), BN-1 to BN- 584 was used as a doped light-emitting material (the doping concentration was 3wt%), TmPyPB was used as an electron transport material, LiF was used as an electron injection layer, and Al was used as a metal cathode. Effect Example The structure of the organic electroluminescent device is [ITO/PEDOT:PSS (20 nm)/Poly-HTL(50 nm)/H1-33:TRZ-1+3wt%BN-n/TmPyPB(50 nm)/LiF (1 nm)/Al(100 nm)]. where 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 prove that the luminescent material provided by the present invention 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. The results of the effect examples are shown in Table 4.

[Table 4] Main parameters of electroluminescence performance of BN-n (n = 1-584). Compound (BN-n) Electroluminescence spectrum peak position (nm) Electroluminescence spectrum half width (nm) Electroluminescence External Quantum Efficiency (%) BN-1 520 43 25.5 BN-2 519 41 25.7 BN-3 520 42 25.4 BN-4 519 44 25.7 BN-5 520 42 25.6 BN-6 520 44 25.8 BN-7 521 43 25.5 BN-8 520 43 25.8 BN-9 519 42 25.5 BN-10 520 43 25.6 BN-11 521 44 25.6 BN-12 520 43 25.8 BN-13 521 45 25.5 BN-14 521 45 25.6 BN-15 520 43 25.7 BN-16 521 44 25.5 BN-17 509 44 25.6 BN-18 510 43 26.0 BN-19 509 44 25.4 BN-20 510 43 25.6 BN-21 510 44 25.8 BN-22 511 43 25.5 BN-23 509 45 25.7 BN-24 511 44 25.4 BN-25 510 45 25.5 BN-26 510 43 25.6 BN-27 509 44 26.1 BN-28 511 45 25.4 BN-29 511 44 25.5 BN-30 510 45 25.7 BN-31 511 44 25.5 BN-32 512 43 25.4 BN-33 529 44 25.9 BN-34 530 45 25.6 BN-35 530 43 25.5 BN-36 531 43 25.6 BN-37 530 45 25.4 BN-38 530 43 25.5 BN-39 529 44 25.6 BN-40 531 43 26.0 BN-41 530 43 25.8 BN-42 531 44 25.7 BN-43 530 43 25.6 BN-44 532 45 25.9 BN-45 531 44 25.5 BN-46 530 43 25.7 BN-47 531 43 25.8 BN-48 531 42 25.8 BN-49 518 43 25.4 BN-50 518 44 25.6 BN-51 519 43 25.7 BN-52 519 45 26.0 BN-53 520 43 25.6 BN-54 519 44 25.5 BN-55 519 45 25.5 BN-56 520 44 25.7 BN-57 520 43 25.9 BN-58 521 44 25.7 BN-59 518 45 25.5 BN-60 520 43 25.4 BN-61 519 44 25.8 BN-62 521 43 25.6 BN-63 521 45 25.6 BN-64 522 44 25.5 BN-65 527 45 25.7 BN-66 526 45 25.8 BN-67 525 43 25.6 BN-68 526 44 25.5 BN-69 527 44 25.8 BN-70 526 43 25.6 BN-71 526 43 25.7 BN-72 525 45 25.5 BN-73 527 43 25.5 BN-74 526 44 25.8 BN-75 527 44 25.9 BN-76 526 45 25.5 BN-77 528 44 25.5 BN-78 527 43 25.8 BN-79 527 43 25.6 BN-80 528 44 25.7 BN-81 515 43 25.6 BN-82 515 43 25.8 BN-83 516 45 25.8 BN-84 515 43 25.5 BN-85 516 45 25.7 BN-86 515 43 25.6 BN-87 516 44 25.7 BN-88 516 45 25.8 BN-89 517 44 25.5 BN-90 517 43 25.4 BN-91 516 43 25.5 BN-92 516 44 25.9 BN-93 517 43 25.4 BN-94 516 43 25.8 BN-95 517 44 25.6 BN-96 517 43 25.5 BN-97 538 43 25.8 BN-98 538 45 25.5 BN-99 539 43 25.5 BN-100 539 43 25.7 BN-101 538 44 25.6 BN-102 539 45 25.4 BN-103 538 44 25.5 BN-104 539 45 25.7 BN-105 537 44 25.8 BN-106 538 43 25.6 BN-107 536 44 25.8 BN-108 538 43 25.5 BN-109 539 45 25.7 BN-110 538 44 25.5 BN-111 539 45 25.6 BN-112 538 44 25.5 BN-113 526 43 25.6 BN-114 526 43 25.9 BN-115 525 44 25.8 BN-116 526 45 25.7 BN-117 525 43 25.7 BN-118 527 44 25.9 BN-119 526 43 25.4 BN-120 527 43 25.5 BN-121 526 45 25.8 BN-122 526 43 25.9 BN-123 525 43 25.8 BN-124 526 44 25.6 BN-125 527 45 25.7 BN-126 528 43 25.5 BN-127 529 43 25.4 BN-128 529 46 25.7 BN-129 563 54 25.6 BN-130 563 55 26.1 BN-131 564 55 25.9 BN-132 564 53 25.8 BN-133 565 54 25.4 BN-134 565 54 25.4 BN-135 565 53 25.7 BN-136 566 55 25.7 BN-137 565 54 25.5 BN-138 564 53 25.4 BN-139 565 54 25.7 BN-140 565 55 25.5 BN-141 566 54 25.8 BN-142 567 53 25.6 BN-143 566 54 25.6 BN-144 567 54 25.5 BN-145 555 55 25.7 BN-146 554 54 25.6 BN-147 555 53 25.8 BN-148 556 53 25.9 BN-149 555 54 25.5 BN-150 555 54 25.5 BN-151 554 54 25.7 BN-152 556 53 25.8 BN-153 557 55 25.7 BN-154 556 54 25.5 BN-155 555 54 25.6 BN-156 556 53 25.7 BN-157 557 53 25.4 BN-158 556 54 25.5 BN-159 556 53 25.7 BN-160 557 55 25.6 BN-161 630 54 25.6 BN-162 630 53 25.5 BN-163 629 55 25.4 BN-164 630 56 25.4 BN-165 629 56 25.6 BN-166 629 55 25.4 BN-167 628 54 25.3 BN-168 630 54 25.4 BN-169 629 55 25.3 BN-170 629 54 25.5 BN-171 631 56 25.4 BN-172 631 55 25.5 BN-173 629 54 25.3 BN-174 630 54 25.4 BN-175 630 55 25.2 BN-176 631 56 25.3 BN-177 619 55 25.5 BN-178 620 56 25.4 BN-179 619 54 25.3 BN-180 619 55 25.2 BN-181 620 56 25.5 BN-182 621 54 25.3 BN-183 620 55 25.4 BN-184 621 55 25.4 BN-185 621 54 25.3 BN-186 622 54 25.3 BN-187 622 56 25.2 BN-188 621 55 25.3 BN-189 621 55 25.6 BN-190 621 54 25.3 BN-191 622 54 25.2 BN-192 622 55 25.4 BN-193 497 40 25.8 BN-194 496 41 25.6 BN-195 496 41 25.5 BN-196 497 40 25.4 BN-197 498 41 25.4 BN-198 498 40 25.5 BN-199 499 39 25.8 BN-200 498 39 25.6 BN-201 497 40 25.4 BN-202 499 41 25.7 BN-203 497 40 25.6 BN-204 498 39 25.4 BN-205 497 40 25.7 BN-206 499 42 25.5 BN-207 497 41 25.6 BN-208 499 40 25.7 BN-209 497 42 25.5 BN-210 498 44 25.5 BN-211 499 44 25.6 BN-212 497 42 25.8 BN-213 499 42 25.4 BN-214 498 42 25.7 BN-215 499 43 25.5 BN-216 498 45 25.6 BN-217 498 44 25.7 BN-218 499 43 25.7 BN-219 499 44 25.5 BN-220 498 45 25.6 BN-221 499 44 25.7 BN-222 498 45 25.5 BN-223 498 44 25.6 BN-224 499 45 25.6 BN-225 502 46 25.7 BN-226 502 44 25.5 BN-227 501 43 25.6 BN-228 501 43 25.4 BN-229 502 45 25.4 BN-230 502 44 25.9 BN-231 501 44 25.8 BN-232 501 45 25.7 BN-233 502 44 25.4 BN-234 502 43 25.5 BN-235 501 44 25.6 BN-236 501 45 25.7 BN-237 502 43 25.8 BN-238 503 44 25.6 BN-239 503 44 25.4 BN-240 502 45 25.6 BN-241 501 44 25.6 BN-242 502 43 25.7 BN-243 502 43 25.8 BN-244 503 45 25.8 BN-245 502 43 25.6 BN-246 502 43 25.4 BN-247 503 42 25.7 BN-248 502 44 25.8 BN-249 502 43 25.6 BN-250 504 45 25.5 BN-251 503 44 25.7 BN-252 503 44 25.8 BN-253 504 43 25.5 BN-254 503 45 25.4 BN-255 503 44 25.6 BN-256 504 43 25.7 BN-257 505 43 26.1 BN-258 506 44 25.7 BN-259 505 43 25.5 BN-260 506 43 25.6 BN-261 506 44 25.5 BN-262 507 43 25.5 BN-263 508 44 25.7 BN-264 507 45 25.8 BN-265 507 44 25.7 BN-266 508 44 25.6 BN-267 508 45 25.4 BN-268 509 43 25.6 BN-269 509 44 25.4 BN-270 508 44 25.5 BN-271 507 45 25.5 BN-272 507 43 25.6 BN-273 509 45 25.7 BN-274 508 45 25.8 BN-275 507 44 25.7 BN-276 507 45 25.5 BN-277 507 44 25.7 BN-278 508 43 25.6 BN-279 509 44 25.4 BN-280 509 43 25.6 BN-281 508 44 25.5 BN-282 508 45 25.4 BN-283 509 43 25.7 BN-284 509 43 25.7 BN-285 508 44 25.5 BN-286 508 42 25.6 BN-287 509 44 25.7 BN-288 509 43 25.8 BN-289 507 45 25.5 BN-290 506 44 25.7 BN-291 508 44 25.5 BN-292 508 45 25.8 BN-293 509 45 25.6 BN-294 510 44 25.5 BN-295 510 43 25.6 BN-296 509 45 25.7 BN-297 509 43 25.8 BN-298 511 44 25.5 BN-299 510 44 25.7 BN-300 510 43 25.6 BN-301 511 45 25.7 BN-302 510 44 25.8 BN-303 509 44 25.6 BN-304 510 43 25.5 BN-305 509 44 25.4 BN-306 511 45 25.8 BN-307 511 43 26.1 BN-308 510 43 25.8 BN-309 511 45 25.7 BN-310 512 44 25.7 BN-311 511 45 25.5 BN-312 512 44 25.7 BN-313 511 43 25.9 BN-314 512 44 25.7 BN-315 511 45 25.6 BN-316 512 43 25.6 BN-317 512 43 25.6 BN-318 511 45 25.5 BN-319 512 44 25.5 BN-320 512 43 25.8 BN-321 502 44 25.6 BN-322 503 43 25.5 BN-323 504 43 25.4 BN-324 503 44 25.4 BN-325 504 43 25.8 BN-326 503 43 25.5 BN-327 504 44 25.5 BN-328 505 44 25.6 BN-329 505 43 25.7 BN-330 504 44 25.6 BN-331 505 44 25.5 BN-332 506 45 25.6 BN-333 505 45 25.7 BN-334 505 44 25.6 BN-335 506 45 25.5 BN-336 504 44 25.7 BN-337 505 45 25.5 BN-338 506 45 25.6 BN-339 504 44 25.8 BN-340 506 45 25.6 BN-341 505 45 25.9 BN-342 506 44 25.7 BN-343 506 43 25.5 BN-344 505 44 25.5 BN-345 506 44 25.8 BN-346 505 43 25.9 BN-347 506 43 25.7 BN-348 505 43 25.6 BN-349 506 45 25.5 BN-350 505 43 25.7 BN-351 505 44 25.6 BN-352 506 43 25.7 BN-353 507 45 25.7 BN-354 508 44 25.4 BN-355 507 44 25.8 BN-356 507 43 25.7 BN-357 507 44 25.5 BN-358 508 45 25.5 BN-359 507 43 25.6 BN-360 507 43 25.4 BN-361 509 45 25.7 BN-362 508 44 25.6 BN-363 508 43 25.5 BN-364 507 44 25.9 BN-365 508 45 25.8 BN-366 509 45 26.1 BN-367 507 44 25.9 BN-368 507 43 25.4 BN-369 508 44 25.7 BN-370 509 43 25.6 BN-371 507 43 25.7 BN-372 506 43 25.5 BN-373 508 45 25.7 BN-374 509 44 25.5 BN-375 507 43 25.7 BN-376 509 44 25.5 BN-377 508 44 25.8 BN-378 507 45 25.7 BN-379 508 43 25.6 BN-380 508 43 25.5 BN-381 508 44 25.5 BN-382 509 43 25.5 BN-383 508 44 25.8 BN-384 509 43 25.5 BN-385 517 44 25.7 BN-386 516 43 25.6 BN-387 517 45 25.8 BN-388 518 44 25.7 BN-389 516 43 25.8 BN-390 517 43 25.9 BN-391 518 44 25.4 BN-392 518 45 25.7 BN-393 517 45 25.7 BN-394 517 44 25.6 BN-395 518 43 25.9 BN-396 517 45 25.4 BN-397 518 46 25.5 BN-398 519 44 25.6 BN-399 518 43 25.7 BN-400 517 44 25.5 BN-401 519 44 25.6 BN-402 518 43 25.4 BN-403 519 45 25.7 BN-404 516 44 25.8 BN-405 519 45 25.9 BN-406 518 45 25.6 BN-407 518 46 25.4 BN-408 519 44 25.8 BN-409 519 45 25.6 BN-410 518 45 25.7 BN-411 519 44 25.6 BN-412 518 43 25.8 BN-413 519 44 25.5 BN-414 518 45 25.6 BN-415 518 43 25.7 BN-416 519 43 25.4 BN-417 520 45 25.5 BN-418 521 44 25.6 BN-419 521 43 25.4 BN-420 520 43 25.7 BN-421 521 43 25.7 BN-422 521 45 25.6 BN-423 520 43 25.8 BN-424 520 43 25.4 BN-425 521 44 25.8 BN-426 521 43 25.9 BN-427 520 45 25.6 BN-428 521 44 25.9 BN-429 522 43 25.5 BN-430 521 45 25.4 BN-431 520 43 25.7 BN-432 521 43 25.8 BN-433 521 43 25.6 BN-434 519 44 25.6 BN-435 520 43 25.7 BN-436 521 44 25.6 BN-437 521 44 25.5 BN-438 522 45 25.7 BN-439 522 44 25.9 BN-440 521 43 25.5 BN-441 521 44 25.6 BN-442 522 43 25.7 BN-443 521 44 25.8 BN-444 521 45 25.8 BN-445 522 43 25.5 BN-446 521 44 25.6 BN-447 522 45 25.7 BN-448 522 44 25.6 BN-449 549 54 25.6 BN-450 549 53 25.9 BN-451 551 52 25.5 BN-452 550 52 25.8 BN-453 550 54 25.6 BN-454 551 53 25.5 BN-455 552 54 25.9 BN-456 552 54 25.7 BN-457 551 55 25.7 BN-458 552 54 25.4 BN-459 551 53 25.7 BN-460 551 54 25.5 BN-461 552 55 25.6 BN-462 552 53 25.6 BN-463 552 53 25.9 BN-464 551 54 25.4 BN-465 552 54 25.7 BN-466 551 53 25.6 BN-467 552 52 25.5 BN-468 551 53 25.7 BN-469 551 53 25.7 BN-470 552 54 25.8 BN-471 552 55 25.5 BN-472 551 53 25.7 BN-473 551 54 25.6 BN-474 552 54 25.8 BN-475 552 55 25.7 BN-476 551 54 25.9 BN-477 552 55 25.6 BN-478 552 54 25.5 BN-479 551 53 25.4 BN-480 552 54 25.5 BN-481 553 53 25.6 BN-482 554 53 25.8 BN-483 554 54 25.9 BN-484 555 54 25.8 BN-485 556 53 25.9 BN-486 556 54 25.5 BN-487 557 55 25.7 BN-488 557 53 25.7 BN-489 557 55 25.8 BN-490 556 54 25.4 BN-491 556 54 25.7 BN-492 557 53 25.6 BN-493 558 54 25.8 BN-494 557 55 25.4 BN-495 556 55 25.5 BN-496 557 54 25.8 BN-497 558 53 25.7 BN-498 557 54 25.5 BN-499 557 54 25.6 BN-500 557 53 25.5 BN-501 558 54 25.9 BN-502 558 54 25.8 BN-503 557 53 25.7 BN-504 558 53 25.6 BN-505 558 54 25.7 BN-506 557 55 25.6 BN-507 559 54 25.6 BN-508 558 53 25.9 BN-509 557 54 25.6 BN-510 557 55 25.5 BN-511 558 54 25.4 BN-512 559 54 25.7 BN-513 581 55 25.7 BN-514 580 55 25.6 BN-515 581 54 25.4 BN-516 582 55 25.7 BN-517 582 56 25.5 BN-518 582 53 25.6 BN-519 581 53 25.7 BN-520 582 54 25.6 BN-521 582 53 25.7 BN-522 581 54 25.4 BN-523 581 54 25.5 BN-524 583 55 25.5 BN-525 583 55 25.7 BN-526 582 56 25.6 BN-527 582 54 25.7 BN-528 581 55 25.9 BN-529 582 54 25.4 BN-530 583 54 25.8 BN-531 583 55 25.5 BN-532 581 54 25.6 BN-533 581 56 25.7 BN-534 582 55 25.6 BN-535 582 55 25.7 BN-536 583 54 25.7 BN-537 582 53 25.6 BN-538 583 54 25.5 BN-539 583 55 25.4 BN-540 582 55 25.7 BN-541 582 54 25.6 BN-542 582 55 25.5 BN-543 583 54 25.6 BN-544 583 55 25.9 BN-545 584 53 25.7 BN-546 583 53 25.5 BN-547 584 54 25.4 BN-548 584 56 25.6 BN-549 585 55 25.4 BN-550 584 54 25.6 BN-551 585 55 25.5 BN-552 586 54 25.7 BN-553 586 56 25.7 BN-554 585 55 25.6 BN-555 585 55 25.8 BN-556 585 56 25.7 BN-557 586 54 25.5 BN-558 585 55 25.7 BN-559 586 55 25.6 BN-560 585 56 25.5 BN-561 585 55 25.7 BN-562 586 56 25.8 BN-563 585 55 25.4 BN-564 585 54 25.6 BN-565 586 55 25.9 BN-566 586 55 25.7 BN-567 585 54 25.8 BN-568 585 54 25.6 BN-569 585 55 25.4 BN-570 586 56 25.5 BN-571 586 55 25.8 BN-572 586 55 25.9 BN-573 587 56 25.8 BN-574 586 56 25.6 BN-575 586 57 25.6 BN-576 587 56 25.9 BN-577 631 50 25.0 BN-578 629 52 25.1 BN-579 629 49 25.2 BN-580 630 51 25.2 BN-581 628 50 25.3 BN-582 627 52 25.1 BN-583 627 50 25.2 BN-584 626 51 25.0

The above descriptions are only exemplary embodiments of the present invention, and are not intended to limit the protection scope of the present invention. The protection scope of the present invention is determined by the patent scope of the attached invention application.

1: ITO anode 2: hole injection layer 3: hole transport layer 4: Light-emitting layer 5: Electron transport layer 6: Electron injection layer 7: Metal cathode

The drawings of the embodiments will be briefly introduced below. Obviously, the drawings in the following description only relate to some embodiments of the present invention, rather than limit the present invention. [Fig. 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 transport layer. Electron injection layer, 7 is a metal cathode. [Fig. 2] is the photoluminescence 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. 3] is the electroluminescence spectrum of the compound BN-66 doped thin film in Effect Example 2, wherein the composition of the doped thin film is H1-1 (97 wt%): BN-66 (3 wt%). [Fig. 4] is the temperature-variable time-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 variation of external quantum efficiency with brightness of compound BN-66 doped device, in which the doping weight percentage composition of the light-emitting layer is H1-1 (97 wt%): BN-66 (3 wt%).

1: ITO anode

2: hole injection layer

3: hole transport layer

4: Light-emitting layer

5: Electron transport layer

6: Electron injection layer

7: Metal cathode

Claims (20)

A boron-nitrogen compound, characterized by having the structure shown in formula I or II,

Wherein, 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 E is ^a single bond or

; R ¹¹ and R ²² are independently H, D (deuterium), C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy at each occurrence; R is:

, H, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₆ -C ₁₄ aryl, C ₆ -C substituted by one or more R ^d ₁₄ -aryl, 5- to 18-membered heteroaryl, or 5- to 18-membered heteroaryl substituted with one or more R ^d ; R ⁴ , R ⁵ and R ⁶ are each 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, by one or more R ^d Substituted C ₆ ~C ₁₄ aryl, 5- to 18-membered heteroaryl or 5- to 18-membered heteroaryl substituted by one or more R ^; R 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, substituted by one or more R ^b C ₆ ~C ₁₄ aryl, 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl substituted by one or more R ^b , diphenylamino, or substituted by one or more R ^b The diphenylamino group; 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, 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 Aryl, diphenylamino, or diphenylamino substituted by one or more R ^c ; each occurrence of 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, C ₆ -C ₁₄ aryl substituted by one or more R ^d , 5- to 18-membered heteroaryl, 5- to 18-membered heteroaryl, diphenylamino, or diphenylamino substituted with one or more R ^{d ;} each occurrence of 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 substituted by one or more R ^e ₁₄ Aryl; each occurrence of ^Re 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; The above-mentioned alkyl, alkoxy, cycloalkyl, aryl, and heteroaryl are optionally substituted by one or more substituents selected from the following groups: halogen, -CN, C ₁ ~C ₁₂ alkane base, 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 boron-nitrogen compound according to claim 1, wherein the frontier molecular orbital has 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. HOMO is distributed on the two Ns, and LUMO is distributed on the B atom, ring m2 and ring ph2. The boron-nitrogen compound according to claim 1, wherein E in formula I is a single bond or

; wherein in formula II

for

or

; wherein in formula I and II

Any of the following groups:

; wherein in formula I and II

Any of the following groups:

. The boron-nitrogen compound according to claim 1, wherein R ¹¹ and R ²² are independently H or D (deuterium), and at least one of R ¹¹ and R ²² appearing in pairs is hydrogen. The boron-nitrogen compound according to claim 4, wherein both R ¹¹ and R ²² are hydrogen. The boron-nitrogen compound according to claim 5, wherein each occurrence of R ¹ is independently H, F, CF ₃ , C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, cyclohexyl, adamantane base, phenyl, naphthyl, phenyl substituted by one or more ^Ra , carbazolyl, carbazolyl substituted by one or more ^Ra , diphenylamino, or substituted by one or more ^Ra The diphenylamino group, the R ^a is selected from C ₁ -C ₆ alkyl, C ₁ -C ₆ fluoroalkyl and C ₁ -C ₆ alkoxy. The boron nitrogen compound according to claim 1, wherein, E is a single bond or a benzene ring; R ¹ is independently H, methyl, tert-butyl, phenyl, 4-tolyl, 3-toluene each time it occurs base, 3,5-xylyl, 4-tert-butylphenyl, 3-tert-butylphenyl, 3,5-di-tert-butylphenyl, diphenylamine, bis(p-tolyl)amine, or di(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-methylphenyl, 3-methylphenyl, 3,5-xylyl, 4-tert-butylphenyl, 3-tert-butylphenyl, 3,5-di-tert-butylphenyl, 4-C ₁ ~C ₁₀ alkoxyphenyl, 3-C ₁ ~C ₁₀ alkoxyphenyl, or 3,5-diC ₁ ~C ₁₀ alkoxy phenyl; R ⁵ is H. The boron-nitrogen compound according to claim 1, wherein it is any one of the following compounds:

. An organic electroluminescent composition characterized by comprising the boron-nitrogen compound as described in any one of claims 1 to 8. The organic electroluminescent composition according to claim 9, wherein it also includes a host material, the host material has electron and/or hole transport capability, and the triplet excited state energy of the host material is higher than that of the boron nitride compound triplet excited state energy. The organic electroluminescent composition of claim 10, wherein the host material accounts for 99.7wt% to 70.0wt% of the composition, and the boron-nitrogen compound accounts for 0.3wt% to -30.0wt% of the composition. The organic electroluminescent composition according to claim 11, wherein the host material comprises one or more of the compounds represented by the formulae (H-1) to (H-6),

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 organic electroluminescent composition according to claim 12, wherein the host material comprises two kinds of compounds of formula (H-1) to (H-6), and the weight ratio of the two compounds is 1:5 to 5:1. The organic electroluminescent composition according to claim 12, wherein the host material is one or two of the compounds H1-1 to H1-427, and when the host material is two of the compounds H1-1 to H1-427 When planting, the weight ratio of the two compounds is 1:5 to 5:1,

. The organic electroluminescent composition according to claim 12, wherein the host material also comprises any one of the 1,3,5-triazine derivatives represented by the formulae Trz1-A, Trz2-A and Trz3-A; And the 1,3,5-triazine derivatives represented by Trz1-A, Trz2-A or Trz3-A are represented by H-1, H-2, H-3, H-4, H-5 and H-6 The weight ratio between the compounds is 1:5 to 5:1,

Wherein, one or two of 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; R ^Tz is any one of the substituent groups shown in the following formula:

. The organic electroluminescent composition according to claim 15, wherein the host material comprises any one of 1,3,5-triazine derivatives represented by formulae TRZ-1 to TRZ-56 and formulas H1-1 to TRZ-56 It is composed of any one of carbazole or carboline derivatives shown in H1-427; in the host material, the weight ratio between 1,3,5-triazine derivatives and carbazole or carboline derivatives is 1:5 to 5 :1,

. An organic electroluminescence device, characterized in that at least one of the light-emitting layer, electron injection layer, electron transport layer, hole transport layer, and hole injection layer comprises boron as described in any one of claims 1 to 8 A nitrogen compound or the organic electroluminescent composition according to any one of claims 9 to 16. The organic electroluminescent device according to claim 17, wherein the light-emitting layer comprises the boron nitride compound or the organic electroluminescent composition. The organic electroluminescent device according to claim 17 or 18, wherein it is used for preparing an organic electroluminescent display or a lighting source. A method for preparing a boron-nitrogen compound as claimed in claim 1, characterized by comprising the steps shown in the following reaction formulas (1) and (2):

In the reaction formula (1), 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 is substituted by boron ester; In the reaction formula (2), 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; In the reaction formula (2), 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 , R are as defined in claim 1 .

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