CN111362978B - Boron-nitrogen heteroaromatic compound used as blue fluorescent material and application thereof - Google Patents

Boron-nitrogen heteroaromatic compound used as blue fluorescent material and application thereof Download PDF

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CN111362978B
CN111362978B CN201811590545.7A CN201811590545A CN111362978B CN 111362978 B CN111362978 B CN 111362978B CN 201811590545 A CN201811590545 A CN 201811590545A CN 111362978 B CN111362978 B CN 111362978B
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陈义丽
丰佩川
孙伟
单宏斌
魏鹏
杨阳
陈跃
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Yantai Xianhua Chem Tech Co ltd
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Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a boron-nitrogen heteroaromatic compound used as a blue fluorescent material and application thereof. The compound of the invention can achieve red shift of different degrees of absorption and emission spectra through modification of different groups, and adjust the energy of a front line orbit of a heteroaromatic system to enable the heteroaromatic system to have larger E gap So that the blue-light emitting material can be matched with each blue object light emitting material to form a light emitting layer of the OLED, and can also be used as a hole transport layer material or an electron transport layer material of an OLED device; the organic electroluminescent device has high luminous efficiency and improved device performance.

Description

Boron-nitrogen heteroaromatic compound used as blue fluorescent material and application thereof
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a boron-nitrogen heteroaromatic compound used as a blue fluorescent material and application thereof.
Background
In the research of organic electroluminescent devices (abbreviated as OLEDs), blue luminescent materials are necessary, which can be used as a luminescent layer to prepare blue OLEDs of one of three primary colors, and other luminescent materials can be doped in the blue luminescent materials to obtain green and red luminescent devices. The blue light emitting material generally has a wide energy gap and its Electron Affinity (EA) and first ionization energy (IP) are matched.
The blue luminescent material requires that the chemical structure of the material has a conjugated structure to a certain extent in molecular design, but the dipole of the molecule cannot be too large, otherwise, the luminescent spectrum is easy to red shift to a green region. At present, blue luminescent materials mainly comprise aromatic blue light materials containing only carbon and hydrogen, arylamine blue light materials, boron-nitrogen-containing heterocyclic blue light materials, organic silicon blue light materials and the like.
Boron, an element that is ortho to the carbon elements of the periodic table of elements, is often used in limited applications in chemical reagents and catalysts. The boron-containing organic light emitting materials can be generally classified into two major groups, i.e., trivalent boron and quadrivalent boron. The boron element and the nitrogen element are two elements adjacent to the carbon element, and the carbon atom and the boron atom can form a stable covalent bond; the outermost electron number of the boron atom is 3, and the outermost electron number of the nitrogen atom is 5, so that the boron-nitrogen bond can replace a carbon-carbon bond in an aromatic ring to form a stable boron-nitrogen hetero organic aromatic system, and the position of the boron-nitrogen bond in the heteroaromatic ring can adjust the energy band width of the system, the polarity of the system and the like, so that the boron-nitrogen hetero organic aromatic system possibly has rich photoelectric properties.
The material can be used as a main body material of a light-emitting layer of an OLED device, and can also be used as a hole transport layer material and an electron transport layer material of the OLED device. And the prepared OLED device has good light-emitting characteristics and can be used for preparing light-emitting devices such as blue light and the like.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a boron-nitrogen heteroaromatic compound used as a blue fluorescent material and an application thereof.
The technical scheme for solving the technical problems is as follows: a boron-nitrogen heteroaromatic compound used as a blue fluorescent material has the following structural formula:
Figure BDA0001920145250000021
X 1 、X 2 、X 3 、X 4 、X 5 、X 6 each independently is N or CR 1 ；Y 1 、Y 2 Each independently is N or C;
R 1 、R a 、R b each independently is hydrogen, deuterium, halogen, C (= O) R X 、CN、Si(R X ) 3 、P(＝O)(R X ) 2 、OR X 、S(＝O)R X 、S(＝O) 2 R X Carbonyl group, N (R) X ) 2 Any one of an alkyl or alkoxy group having 1 to 50 carbon atoms, a cycloalkyl group having 3 to 0 carbon atoms, an alkenyl or alkynyl group having 2 to 50 carbon atoms, an aromatic ring system having 6 to 50 aromatic ring atoms, or a heteroaromatic ring system having 5 to 50 aromatic ring atoms;
R X is H, D, F, CN, alkyl having 1 to 50 carbon atoms, an aromatic ring system having 6 to 50 aromatic ring atoms or a heteroaromatic ring system having 5 to 50 aromatic ring atoms.
Further, R 1 The alkyl, alkoxy, alkenyl, alkynyl, aromatic ring systems and heteroaromatic ring systems described in (a) comprise a ring system substituted with one or more R each X The resulting group after substitution of the group.
Further, R 1 The alkyl, alkoxy, alkenyl and alkynyl groups described in (1) contain one or more CH 2 Radical is-R X C＝CR X -、-C≡C-、Si(R X ) 2 、C＝O、C＝N R X 、-C(＝O)O-、-C(＝O)N R X -、P(＝O)(R X ) -O-, -S-, SO, or SO 2 Instead of the latter radical.
Further, R X The alkyl, aromatic ring system and heteroaromatic ring system described in (1) include groups each substituted with F or CN.
Further, any adjacent two or more substituents are linked to form a cyclic group containing one or more heteroatoms, preferably B, N, S, O, or Se.
Preferably, the boraheteroaromatic compound has the following structural formula:
Figure BDA0001920145250000031
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Figure BDA0001920145250000041
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Figure BDA0001920145250000051
the second object of the present invention is to provide a polymer of a boraheteroaromatic compound, which is obtained by polymerizing two or more of the above boraheteroaromatic compounds.
Further, the borazine heteroaromatic compounds are linked to each other by a covalent bond or a bridging group of- (Z) x-; z is B, C, N, O, S, se, CR 2 、NR 3 、AR 4 R 5 An aromatic ring system having 6 to 50 aromatic ring atoms, a heteroaromatic ring system having 5 to 50 aromatic ring atoms, or a linear or cyclic alkyl or alkoxy group having 1 to 50 carbon atoms; x is more than or equal to 1 and is an integer, and x Z are independent;
a is C, si or Ge;
said R is 2 、R 3 、R 4 、R 5 Each independently is hydrogen, deuterium, halogen, C (C = O) R Y 、CN、Si(R Y ) 3 、P(＝O)(R Y ) 2 、OR Y 、S(＝O)R Y 、S(＝O) 2 R Y Carbonyl group, N (R) Y ) 2 Any of an aromatic ring system having 6 to 30 aromatic ring atoms, a heteroaromatic ring system having 5 to 30 aromatic ring atoms, or a linear or cyclic alkyl or alkoxy group having 1 to 20 carbon atoms;
R Y is H, D, F, CN, alkyl having 1 to 20 carbon atoms, an aromatic ring system having 6 to 30 aromatic ring atoms or a heteroaromatic system having 5 to 30 aromatic ring atoms.
Further, R Y The alkyl, aromatic ring system and heteroaromatic ring system described in (1) include groups each substituted with F or CN.
Preferably, the above multimer has the following structural formula:
Figure BDA0001920145250000061
the third purpose of the invention is to provide the application of the borazine aromatic compound or the polymer as an electroluminescent material in an organic electroluminescent device.
An organic electroluminescent device comprises an anode layer, a cathode layer and a functional layer arranged between the anode layer and the cathode layer, wherein the functional layer contains the boraaza aromatic compound or polymer.
Further, the functional layer refers to a light emitting layer; the light-emitting layer comprises a host light-emitting material and a guest light-emitting material, and the borazine aromatic compound or the polymer is used as the host light-emitting material.
Further, the functional layer refers to an electron transport layer or a hole transport layer, and the borazine aromatic compound or the polymer is used as a material of the electron transport layer or the hole transport layer.
An aromatic ring in the context of the present invention is an aromatic ring which does not comprise any heteroatoms as aromatic ring atoms. Thus, an aromatic ring system in the context of the present invention is to be understood as a system which does not necessarily contain only aryl groups, but wherein a plurality of aryl groups may also be bonded by single bonds or by non-aromatic units (e.g. one or more atoms optionally selected from substituted C, si, N, O or S atoms). In this case, the non-aromatic units contain preferably less than 10% of non-H atoms, based on the total number of non-H atoms in the system. For example, like systems in which two or more aryl groups are linked by a linear or cyclic alkyl, alkenyl or alkynyl group or by a silyl group, such as 9,9 '-spirobifluorene, 9' -diarylfluorene, triarylamine, diaryl ether and stilbene systems, substituted or unsubstituted arylamine groups, substituted or unsubstituted arylthio groups, substituted or unsubstituted aryl ether groups, substituted or unsubstituted dialkylarylsilyl groups, substituted or unsubstituted triarylsilyl groups, substituted or unsubstituted fluorene groups, and the like, are also considered aromatic ring systems in the context of the present invention. Furthermore, systems in which 2 or more than 2 aryl groups are connected to one another by single bonds are also considered to be aromatic ring systems in the context of the present invention, for example systems such as biphenyl and terphenyl.
The heteroaromatic ring is an aromatic ring in which at least one of the aromatic ring atoms is a heteroatom. The heteroatoms are preferably N, O and/or S. The heteroaromatic ring system conforms to the definition of aromatic ring system above, but at least one heteroatom as one of the aromatic ring atoms. In this way, it differs from an aromatic ring system in the sense defined in the application, which according to this definition cannot contain any heteroatoms as aromatic ring atoms.
Aryl groups are those containing from 6 to 50 aromatic ring atoms, none of which are heteroatoms. An aryl group in the context of the present invention is understood to be a simple aromatic ring, i.e. a benzene or fused aromatic polycyclic ring, for example naphthalene, anthracene or phenanthrene. Fused aromatic polycyclic rings in the context of the present application consist of 2 or more than 2 simple aromatic rings fused to one another. Fused between rings is herein understood to mean that the rings share at least one side with each other;
heteroaryl groups are those containing from 5 to 50 aromatic ring atoms, at least one of which is a heteroatom. The heteroatoms of the heteroaryl group are preferably N, O and/or S. Heteroaryl groups in the context of the present invention are understood to mean simple heteroaromatic rings, such as pyridines, pyrimidines or thiophenes, or fused heteroaromatic polycycles, such as quinolines or carbazoles. A fused heteroaromatic polycyclic ring in the context of the present application consists of 2 or more than 2 simple heteroaromatic rings fused to one another. Fused between rings is understood to mean that the rings share at least one side with each other.
Aromatic ring systems having 6 to 40 aromatic ring atoms or heteroaromatic ring systems having 5 to 40 aromatic ring atoms are understood in particular to mean radicals derived from: the groups mentioned above under the aryl group, and also biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, indenofluorene, terpolyfluorene, isotripolyfluorene, spiroterpolyindene, spiroisotridecylene, indenocarbazole, or combinations of these groups.
Aryl or heteroaryl groups, each of which may be substituted by the abovementioned groups and which may be attached to the aromatic or heteroaromatic system via any desired position, are in particular understood as meaning groups which are derived from: benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene,
Figure BDA0001920145250000071
<xnotran> , , , , , , , , , , , , , , , , , , , , , , , , , , -5,6- , -6,7- , -7,8- , , , , , , , , , , , , , , , , ,1,2- ,1,3- , , , , , , , , , , ,1,2,3- ,1,2,4- , ,1,2,3- ,1,2,4- ,1,2,5- ,1,3,4- ,1,2,3- , </xnotran>1,2, 4-thiadiazole, 1,2, 5-thiadiazole, 1,3, 4-thiadiazole, 1,3, 5-triazine, 1,2, 4-triazine, 1,2, 3-triazine, tetrazole, 1,2,4, 5-tetrazine, 1,2,3, 4-tetrazine, 1,2,3, 5-tetrazine, purine, pteridine, indolizine and benzothiadiazole.
In the context of the present invention, straight-chain alkyl groups having from 1 to 50 carbon atoms, branched or cyclic alkyl groups having from 3 to 50 carbon atoms and alkenyl or alkynyl groups having from 2 to 50 carbon atoms are preferably understood to mean methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptene, cycloheptenyl, octenyl, cyclooctenyl, ethynylpropynyl, butynyl, pentynyl, hexynyl or octynyl groups, the individual hydrogen atoms in the individual groups or the CH or CH groups 2 The radicals may also be substituted by the radicals mentioned above.
In the context of the present invention alkyl or thioalkyl groups having 1 to 50 carbon atoms, preferably understood as meaning methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, sec-pentyloxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, 2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, tert-butyloxy n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, sec-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethionine, pentafluoroethylthio, 2-trifluoroethylthio, vinylthio, alkenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthioThio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio or octynylthio, the individual hydrogen atoms in each radical or CH 2 The groups may also be substituted with the above groups.
In the context of the present application, the wording that 2 or more than 2 groups together may form a ring is understood to mean in particular that the two groups are linked to each other by a chemical bond. In addition, the above wording is also understood to mean that if one of the two groups is hydrogen, the second group is bonded to the position to which the hydrogen atom is bonded, thereby forming a ring.
The invention has the beneficial effects that: the compound of the invention can achieve red shift of different degrees of absorption and emission spectra through modification of different groups, and adjust the energy of a front line orbit of a heteroaromatic system to enable the heteroaromatic system to have larger E gap So that the blue-light emitting material can be matched with each blue object light emitting material to form a light emitting layer of the OLED, and can also be used as a hole transport layer material or an electron transport layer material of an OLED device; the organic electroluminescent device has high luminous efficiency and improved device performance.
Drawings
FIG. 1 is a schematic diagram of an OLED structure of an organic electroluminescent material;
in the figure, 1, a glass substrate; 2. an anode layer; 3. a hole injection layer; 4. a hole transport layer; 5. a light emitting layer; 6. an electron transport layer; 7. an electron injection layer; 8. a cathode layer.
Detailed Description
The principles and features of this invention are described below in conjunction with examples which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
1. Synthesis examples of the Compounds
The synthesis of the compound T in the I class has the following reaction general formula:
(1)
Figure BDA0001920145250000101
(2)
Figure BDA0001920145250000102
(3)
Figure BDA0001920145250000103
the preparation method comprises the following steps:
(1) Adding R into a microwave reaction bottle which is dried by an oven and provided with a stirring rod 01X BF 3 K (0.5mmol, 1equiv.), sealing the reaction bottle with a bottle cap lined with a disposable polytetrafluoroethylene film, vacuumizing, and cleaning with argon for three times; under the protection of argon, CPME (0.5 mL), toluene (0.5 mL), re1 (0.75mmol, 1.5equv, or 0.60mmol, 1.2equv), siCl were added in sequence 4 (0.5mmol，1equiv.)、NEt 3 (0.75 equiv., if necessary); the resulting mixture was heated at 60 ℃ for 4h or 40 ℃ for 18h, then cooled to room temperature and diluted with hexane (2 mL); the mixture was filtered (2 inch silica column) and charged with 20% CH 2 Cl 2 Eluting with hexane (10 ml), and vacuum desolventizing to obtain intermediate INT1a; a few need to pass through the column (30% CH) 2 Cl 2 N-hexane as mobile phase);
adding INT1a into a round bottom flask with a stirring rod, sealing with a rubber pad, vacuumizing, cleaning with argon for three times, and adding anhydrous CH 2 Cl 2 (10 mL), cooled to 0 ℃; under the protection of argon, bromine CH is added at a rate of 1.1mmol/h 2 Cl 2 The solution (352mg, 2.2mmol, 1.1equiv.) was slowly warmed to room temperature, and after completion of the reaction as indicated by TLC, the solvent was removed in vacuo; the crude product was passed through a column (0-30% CH) 2 Cl 2 N-hexane as a mobile phase) to obtain an intermediate INT2a;
(2) Preparing a bromine-containing compound Re2 into a Grignard reagent INT1b under the anhydrous and anaerobic conditions;
(3) Sequentially adding t-Bu into a microwave reaction bottle with a stirring rod 3 P-Pd-G2 (3.3. Mu. Mol,1 mol%), reaction intermediate INT2a of step (1) (0.33mmol, 1equiv.), lined once with linerSealing the reaction bottle by a bottle cap of a polytetrafluoroethylene film, vacuumizing, and cleaning with argon for three times; degassed THF (0.8 mL) was added under argon and the temperature was reduced to 0 deg.C; dropwise adding the intermediate INT1b prepared in the step (2) (1M THF solution, and diluting from 0.4mL to 0.8 mL) at 0 ℃ for more than 15min; overnight and slowly warmed to room temperature, NH 4 Cl (0.5 mL) salt solution quenched, etOAc (3X 2 mL) extracted, mgSO 4 Drying, vacuum desolventizing, and purifying with column (silica gel as stationary phase, 0-20% CH) 2 Cl 2 Hexane as mobile phase) to obtain product T.
The synthesis of the II compound T1 has the following reaction equation:
Figure BDA0001920145250000111
the preparation method comprises the following steps:
adding R into a microwave reaction bottle which is dried by an oven and provided with a stirring rod in sequence 01Y BF 3 K (1.0 equiv.), re (1.0 equiv.), the reaction flask is sealed by a bottle cap lined with a disposable polytetrafluoroethylene film, the reaction flask is vacuumized and is washed with nitrogen for three times, and then CPME (9 equiv.), toluene (10 equiv.), and SiCl are added 4 (1.0 equiv.), stirring at room temperature for 2min, and adding Et under the protection of nitrogen 3 N (0.75 equiv.), heating to 180 ℃ under microwave radiation, heating for 30min, cooling to room temperature, removing the solvent in vacuum, and passing through a column to obtain T1.
Examples of the synthesis of compounds of type I are shown in Table 1;
TABLE 1
Figure BDA0001920145250000121
Examples of the synthesis of compounds of class II are shown in Table 2;
TABLE 2
Figure BDA0001920145250000131
/>
Figure BDA0001920145250000141
2. Application example of organic electroluminescent device
The structure of the compound used in the application example is as follows:
Figure BDA0001920145250000151
/>
application example 1
The preparation process of the organic electroluminescent device is as follows:
(1) Depositing a layer of Indium Tin Oxide (ITO) with the thickness of 100nm on a glass substrate 1 to be used as a transparent anode layer 2;
(2) NPB (N, N '-di (1-naphthyl) -N, N' -diphenyl-1, 1 '-biphenyl-4-4' -diamine) hole transport material with a thickness of 10nm is vacuum-evaporated on the transparent anode layer 2 as a hole injection layer 3, wherein F4-TCNQ (2, 3,5, 6-tetrafluoro-7, 7', 8' -tetracyanoquinodimethane) is doped with an impurity in an amount of 3%;
(3) On the hole injection layer 3, a layer of spiro-TAD (2, 2', 7' -tetrakis (diphenylamino) -9,9' -spirobifluorene) having a thickness of 100nm was formed as a hole transport layer 4;
(4) A luminescent layer 5 with the thickness of 30nm is evaporated on the hole transport layer 4 in vacuum, and the luminescent layer comprises a host luminescent material and an object luminescent material; the main body luminescent material is compound 1 doped with 4wt% of TPPDA (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine);
(5) Sequentially vacuum evaporating a layer of TPQ (2, 3,5, 8-tetraphenylquinoxaline) with the thickness of 30nm on the light-emitting layer 5 to be used as an electron transport layer 6;
(6) Vacuum evaporating Liq with the thickness of 1nm on the electron transport layer 6 to form an electron injection layer 7;
(7) Finally, metal aluminum (Al) with the thickness of 100nm is deposited on the electron injection layer 7 by adopting a vacuum vapor deposition technology to be used as a cathode layer 8 of the device.
Application example 2
The same as in application example 1, except that: the light-emitting layer 5 was a 30nm thick compound 2 doped with 4wt% of TPPDA (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine).
Application example 3
The same as in application example 1, except that: the electron transport layer 6 was a compound 3 having a thickness of 30 nm.
Application example 4
The same as in application example 1, except that: the light-emitting layer 5 was a 30nm thick compound 4 doped with 4wt% of TPPDA (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine).
Application example 5
The same as in application example 1, except that: the electron transport layer 6 was a compound 5 having a thickness of 30 nm.
Application example 6
The same as in application example 1, except that: the light-emitting layer 5 was a 30nm thick compound 6 doped with 4wt% of TPPDA (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine).
Application example 7
The same as in application example 1, except that: the light-emitting layer 5 was a 30nm thick compound 7 doped with 4wt% of TPPDA (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine).
Application example 8
The same as in application example 1, except that: the light-emitting layer 5 was a 30nm thick compound 8 doped with 4wt% of TPPDA (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine).
Application example 9
The same as in application example 1, except that: the light-emitting layer 5 was a 30nm thick compound 9 doped with 4wt% of TPPDA (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine).
Application example 10
The same as in application example 1, except that: the light-emitting layer 5 is a 30nm thick compound 10 doped with 4wt% of TPPDA (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine).
Application example 11
The same as in application example 1, except that: the light-emitting layer 5 was a 30nm thick compound 11 doped with 4wt% of TPPDA (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine).
Application example 12
The same as in application example 1, except that: the hole transport layer 4 is a compound 12 having a thickness of 100 nm.
Application example 13
The same as in application example 1, except that: the hole transport layer 4 is a compound 13 having a thickness of 100 nm.
Application example 14
The same as in application example 1, except that: the light-emitting layer 5 was a 30nm thick compound 14 doped with 4wt% of TPPDA (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine).
Application example 15
The same as in application example 1, except that: the electron transport layer 6 is a compound 15 having a thickness of 30 nm.
Application example 16
The same as in application example 1, except that: the light-emitting layer 5 was a 30nm thick compound 16 doped with 4wt% of TPPDA (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine).
Application example 17
The same as in application example 1, except that: the light-emitting layer 5 was a 30nm thick compound 17 doped with 4wt% of TPPDA (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine).
Application example 18
The same as in application example 1, except that: the light-emitting layer 5 was a 30nm thick compound 18 doped with 4wt% of TPPDA (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine).
The results of the performance tests of the organic electroluminescent devices of application examples 1 to 18 are shown in tables 3,4 and 5;
TABLE 3
Figure BDA0001920145250000191
As can be seen from the data in Table 3, the maximum current efficiency of the device manufactured by using the material provided by the invention as the host material of the light-emitting layer and TPPDA as the guest light-emitting material is 4.2-5.0cd/A, and the light emitted by the device is blue, which indicates that the material provided by the invention is suitable for being used as the host material of blue light.
TABLE 4
Figure BDA0001920145250000201
As can be seen from the data in Table 4, the maximum current efficiency of the device manufactured by using the material provided by the invention as the hole transport material is 4.4-4.6cd/A, and the light emitted by the device is blue, which indicates that the material provided by the invention is suitable for being used as the hole transport material.
TABLE 5
Figure BDA0001920145250000202
As can be seen from the data in Table 5, the maximum current efficiency of the device manufactured by using the material provided by the invention as the electron transport material is 4.4-4.9cd/A, and the light emitted by the device is blue, which indicates that the material provided by the invention is suitable for being used as the electron transport material.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (4)

1. A boron-nitrogen heteroaromatic compound used as a blue fluorescent material is characterized by having the following structural formula:
Figure FDA0004077512980000011
2. an organic electroluminescent device comprising an anode, a cathode and a functional layer disposed between the anode and the cathode, wherein the functional layer contains the boron-nitrogen heteroaromatic compound according to claim 1 as a blue fluorescent material.
3. The organic electroluminescent device according to claim 2, wherein the functional layer is a light-emitting layer, and the borazine heteroaromatic compound according to claim 1 used as a blue fluorescent material is used as a host light-emitting material in the light-emitting layer.
4. The organic electroluminescent device according to claim 2, wherein the functional layer is an electron transport layer or a hole transport layer, and the boron-nitrogen heteroaromatic compound used as the blue fluorescent material according to claim 1 is used as an electron transport layer or a hole transport layer material.
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