CN113185517A - Aza-aromatic compound used as blue fluorescent material and application thereof - Google Patents

Aza-aromatic compound used as blue fluorescent material and application thereof Download PDF

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CN113185517A
CN113185517A CN202011294049.4A CN202011294049A CN113185517A CN 113185517 A CN113185517 A CN 113185517A CN 202011294049 A CN202011294049 A CN 202011294049A CN 113185517 A CN113185517 A CN 113185517A
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aromatic ring
ring system
group
atoms
alkyl
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陈义丽
丰佩川
孙伟
王茂林
胡灵峰
陈跃
宋佳俊
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Yantai Xianhua Chem Tech Co ltd
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Abstract

The invention relates to aza aromatic compounds used as blue fluorescent materials and application thereof, and the structural formula is as follows:
Figure DDA0002784822460000011
wherein, X1、X2、X3、X4、X5、X6、X7、X8Each independently is CR1(ii) a The series of organic materials designed and synthesized by the invention can achieve red shift of different degrees of absorption and emission spectra through modification of different groups, and have larger Egap, so that the organic materials can be matched with various blue object luminescent materials to form a luminescent layer of an OLED (organic light emitting diode) and can also be independently used as blue light luminescent materials.

Description

Aza-aromatic compound used as blue fluorescent material and application thereof
The invention is a divisional application with application number of 2018111942599, application date of 2018.10.15 and name of 'a class of aza aromatic compounds used as blue fluorescent materials and application thereof'.
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a nitrogen heteroaromatic compound used as a fluorescent main material and application thereof.
Background
The luminescent material is used as an important component of an organic electroluminescent device (abbreviated as OLED), and can be mainly divided into a fluorescent material, a phosphorescent material and a thermal activity delayed fluorescent material (abbreviated as TADF material) from the macroscopic view according to a luminescent mechanism; can be mainly divided into host materials and guest materials according to the structure composition; the organometallic complex light-emitting material and the pure organic light-emitting material can be mainly classified according to whether the metal element is used or not.
On a microscopic level, organic light emitting material molecules can be roughly classified into three basic models: alpha type, i.e. the molecules that make up the luminescent material consist of molecular fragments of similar conjugation degrees; beta type, i.e. the molecules that make up the luminescent material are made up of molecular fragments that differ greatly in conjugation; gamma-type, i.e., a molecular fragment constituting a light emitting material, one of which has a stable Highest Occupied Molecular Orbital (HOMO) and highest unoccupied molecular orbital (LUMO) compared to the other, thereby constituting a d (donor) -a (accumulator) structure.
In any model, as an important component of the luminescent material, the following influencing parameters need to be considered in designing the molecule: the host material has larger Egap (HOMO, LUMO energy level difference), namely the Egap of the host material molecule is larger than that of the guest; a higher Tg (glass transition temperature), i.e. the host molecules should have a larger molecular weight, be non-planar, bulky, high molecular weight, have rigid groups, etc.
The use of deep blue light materials in OLEDs can greatly improve the color gamut of OLED displays while reducing the power consumption of the device. However, deep blue light-emitting materials are relatively scarce, and a host material corresponding thereto requires a larger EgapTherefore, the search for a suitable deep blue host material is of great significance.
Disclosure of Invention
Aiming at the current situation of lack of a deep blue luminescent material, the invention provides a nitrogen-mixed aromatic compound used as a blue fluorescent material and application thereof.
The technical scheme for solving the technical problems is as follows:
an aza-aromatic compound used as a blue fluorescent material has the following structural formula:
Figure RE-GDA0003095152170000021
wherein, X1、X2、X3、X4、X5、X6、X7、X8Each independently is N or CR1；
R1Each independently selected from hydrogen, deuterium, halogen, C (C ═ O) RX、CN、Si(RX)3、P(＝O)(RX)2、 ORX、S(＝O)RX、S(＝O)2RXCarbonyl group, N (R)X)2A linear alkyl or alkoxy group having 1 to 50 carbon atoms, a cycloalkyl group having 3 to 50 carbon atoms, an alkenyl or alkynyl group having 2 to 50 carbon atoms, an aromatic ring system having 6 to 50 aromatic ring atoms, a heteroaromatic ring system having 5 to 50 aromatic ring atoms; wherein R is1The alkyl, alkoxy, alkenyl, alkynyl, aromatic ring systems and heteroaromatic ring systems described in (a) comprise a ring system substituted with one or more R eachXThe group obtained after the group substitution; and R is1The alkyl, alkoxy, alkenyl and alkynyl groups described in (1) further contain one or more CH2Radical is-RXC＝CRX-、-C≡C-、 Si(RX)2、C＝O、C＝N RX、-C(＝O)O-、-C(＝O)N RX-、P(＝O)(RX) -O-, -S-, SO, or SO2The radical obtained after substitution;
RXeach independently selected from H, D, F, CN, an alkyl group 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; and R isXThe 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 R1The linkage forms a cyclic group comprising more than one heteroatom, preferably B, N, S, O or Se.
Further, the specific structural formula of the nitrogen heterocyclic aromatic compound is as follows:
Figure RE-GDA0003095152170000041
Figure RE-GDA0003095152170000051
Figure RE-GDA0003095152170000061
the invention also provides a polymer of the aza-aromatic compound, which is formed by polymerizing more than two aza-aromatic compounds.
Further, the nitrogen heteroaromatic compounds are connected with each other through covalent bonds or a bridge group of- (Z) x-, wherein Z is B, C, N, O, S, Se, Si, P, CR2、NR3、AR4R5An aromatic ring system having 6 to 50 aromatic ring atoms, a heteroaromatic ring system having 5 to 50 aromatic ring atoms, a straight-chain 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;
the A is C, Si or Ge;
the R is2、R3、R4、R5Each independently selected from hydrogen, deuterium, halogen, C (C ═ O) RY、CN、 Si(RY)3、P(＝O)(RY)2、ORY、S(＝O)RY、S(＝O)2RYCarbonyl group, N (R)Y)2Any one of an aromatic ring system having 6 to 30 aromatic ring atoms, a heteroaromatic ring system having 5 to 30 aromatic ring atoms, and a linear or cyclic alkyl or alkoxy group having 1 to 20 carbon atoms;
RYeach independently selected from H, D, F, CN, an alkyl group 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; and R isYThe alkyl, aromatic ring system and heteroaromatic ring system described in (1) include groups each substituted with F or CN.
Further, the specific structure of the multimer is as follows:
Figure RE-GDA0003095152170000071
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, e.g., by a linear or cyclic alkyl, alkenyl, or alkynyl group or by a silyl group, such as systems of 9, 9 '-spirobifluorene, 9, 9' -diarylfluorene, triarylamines, diaryl ethers, and stilbenes, substituted or unsubstituted arylamino, substituted or unsubstituted arylthio, substituted or unsubstituted arylene ether, substituted or unsubstituted dialkylarylsilyl, substituted or unsubstituted triarylsilyl, substituted or unsubstituted fluorene, and the like. Are likewise considered to be 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 selected from N, O and/or S. The heteroaromatic ring system conforms to the definition of the 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 present application, which, according to this definition, cannot contain any heteroatoms as aromatic ring atoms.
The aryl groups contain 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 5 to 50 aromatic ring atoms, at least one of which is a heteroatom. The heteroatom of the heteroaryl group is preferably selected from N, O and S. Heteroaryl groups in the context of the present invention are understood to mean simple heteroaromatic rings, such as pyridine, pyrimidine or thiophene, or fused heteroaromatic polycycles, such as quinoline or carbazole. 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 in particular understood to be derived from the following groups: 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 RE-GDA0003095152170000091
Perylene, triphenylene, fluoranthene, phenylanthracene, triphenylene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, mido-5, 6-quinoline, benzo-6, 7-quinoline, benzo-7, 8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxaloimidazole, oxazole, benzoxazole, naphthoxazole, anthraoxazole, phenanthroimidazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, benzopyridazineQuinoxaline, pyrazine, phenazine, naphthyridine, azacarbazole, benzocarbazine, phenanthroline, 1, 2, 3-triazole, 1, 2, 4-triazole, benzotriazole, 1, 2, 3-oxadiazole, 1, 2, 4-oxadiazole, 1, 2, 5-oxadiazole, 1, 3, 4-oxadiazole, 1, 2, 3-thiadiazole, 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, 2, 2-trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptene, cycloheptenyl, octenyl, cyclooctenyl, ethynylpropynyl, butynyl, pentynyl, hexynyl or octynyl groups, individual hydrogen atoms or CH in each radical2The groups may also be substituted with the above groups.
Alkyl or thioalkyl radicals having from 1 to 50 carbon atoms are preferably understood in the context of the present invention to mean 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, 2, 2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, sec-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthioCyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2, 2, 2-trifluoroethylthio, vinylthio, endoalkenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio or octynylthio, the individual hydrogen atoms in the individual radicals or CH2The 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 binds to the position to which the hydrogen atom is bonded, thereby forming a ring.
The aza-aromatic compound and the polymer thereof provided by the invention have the beneficial effects that:
1) the series of organic materials designed and synthesized by the invention can achieve different degrees of red shift of absorption and emission spectra through modification of different groups, and have larger EgapSo that the blue-light emitting material can be matched with each blue object light emitting material to form an OLED light emitting layer, and can also be independently used as a blue light emitting material;
2) the organic material provided by the invention has high luminous efficiency after being applied to an organic electroluminescent device, and the performance of the device is improved.
The invention also claims an organic electroluminescent device which comprises an anode, a cathode and a functional layer positioned between the anode and the cathode, wherein the functional layer contains the nitrogen-mixed aromatic compound or the polymer of the nitrogen-mixed aromatic compound.
Further, the functional layer means a light-emitting layer, and the azaaromatic compound or a polymer of the azaaromatic compound is used as a host light-emitting material in the light-emitting layer.
Further, the functional layer comprises a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer which are sequentially stacked on the anode.
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.
First, Synthesis examples of the Compounds
Example 1:
synthesis of Compound 1, the reaction equation is as follows:
(1)
Figure RE-GDA0003095152170000121
(2)
Figure RE-GDA0003095152170000122
the specific preparation process is as follows:
(1) to a 250mL three-necked flask at-78 ℃ were added R1a2.50g (9.92mmol), Re110mL, CuI0.076g (0.4mmol), Pd (PPh)3)2Cl20.14g(0.2mmol)，Et3N70mL, slowly heating to 50 ℃, stirring for 3h, cooling to room temperature, quenching with NH4Cl solution, separating liquid, collecting an organic phase, and removing the solvent to obtain an intermediate INT2 a;
(2) under the dark condition, CuBr161mg (1.12mmol) and Et were added3Sequentially adding N (6mL), DMA (40mL) and INT2a obtained in the step (1) into a 100mL three-necked bottle; then heating to 180 ℃, and stirring for 18 h; cooling to room temperature and using NH4And (3) quenching the Cl solution, separating liquid, collecting an organic phase, and removing the solvent.
Example 2:
synthesis of Compound 2, the reaction equation is as follows:
(1)
Figure RE-GDA0003095152170000123
(2)
Figure RE-GDA0003095152170000131
the specific preparation method can be referred to the preparation process of example 1, except that R1b is used to react with Re1 in step (1) to obtain INT2 b; INT2b generates product 2 via step (2).
Example 3:
synthesis of Compound 3, the reaction equation is as follows:
(1)
Figure RE-GDA0003095152170000132
(2)
Figure RE-GDA0003095152170000133
the specific preparation method can refer to the preparation process of example 1, except that R1c is used to react with Re1 in step (1) to generate INT2 c; INT2c produced product 3 via step (2).
Example 4:
synthesis of Compound 7, the reaction equation is as follows:
(1)
Figure RE-GDA0003095152170000141
(2)
Figure RE-GDA0003095152170000142
the specific preparation method can refer to the preparation process of example 1, except that R1d is used to react with Re1 in step (1) to generate INT2 d; INT2d produced product 7 via step (2).
Example 5:
synthesis of Compound 9, the reaction equation is as follows:
(1)
Figure RE-GDA0003095152170000143
(2)
Figure RE-GDA0003095152170000144
(3)
Figure RE-GDA0003095152170000151
the preparation method comprises the following steps:
(1) INT2e was prepared with reference to the method of example 1, except that in step (1) the R1e, Re2 reaction was used to generate INT2 e;
(2) INT2e generates INT3e through step (2), and the specific process of step (2) refers to step (2) of example 1;
(3) INT3e, Re33.53g (20.83mmol), toluene 60mL, and Pd [ (t-Bu) produced in step (2) were sequentially added to a 250mL three-necked flask under nitrogen atmosphere3]230.42mg, heating to 110 ℃, refluxing for 8h to perform Buchwald-Hartwig coupling reaction, cooling to room temperature, separating, collecting organic phase, and removing solvent to obtain the product 9.
Example 6:
synthesis of Compound 10, the reaction equation is as follows:
(1)
Figure RE-GDA0003095152170000152
(2)
Figure RE-GDA0003095152170000153
(3)
Figure RE-GDA0003095152170000161
a specific preparation method can be referred to example 5, except that INT3e is used to react with Re4 in step (3) to produce product 10.
Application example of organic electroluminescent device
The structure of the organic electroluminescent device in an application example is shown in fig. 1, and comprises a glass substrate 1, an anode layer 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7 and a cathode layer 8 which are sequentially laminated and combined.
The preparation method of the organic electroluminescent device in the application example comprises the following steps:
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 the thickness of 10nm is vacuum-evaporated on the transparent anode layer 2 to be used as a hole injection layer 3, wherein F4-TCNQ (2, 3, 5, 6-tetrafluoro-7, 7 ', 8, 8' -tetracyanoquinodimethane) is doped with 3 percent of impurities;
3) a layer of spiro-TAD (2, 2 ', 7, 7 ' -tetra (diphenylamino) -9, 9 ' -spirobifluorene) with the thickness of 100nm is arranged on the hole injection layer 3 to be used as a hole transport layer 4;
4) a light-emitting layer 5 with the thickness of 40nm is vacuum-evaporated on the hole transport layer 4, the light-emitting layer 5 is formed by mixing a host material and a guest material, the host material of the light-emitting layer in application examples 1-6 is respectively the compound 1, 2, 3, 7, 9 and 10 of the invention, and 4 wt% of TPPDA (N1, N1, N6, N6-tetraphenylpyrene-1, 6-diamine) is doped as the guest material;
5) vacuum evaporating a layer of TPQ (2, 3, 5, 8-tetraphenylquinoxaline) with the thickness of 30nm on the luminous layer 5 to be used as an electron transport layer 6;
6) a Liq layer with the thickness of 1nm is vacuum evaporated on the electron transmission layer 6 to be used as 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.
The device layer structures of application examples 1 to 6 are shown in table 1.
Table 1 application examples 1-6 device layer structures
Figure RE-GDA0003095152170000171
Through the test, the performance test results of the organic electroluminescent devices of application examples 1 to 6 are shown in table 2.
Table 2: performance test results of organic electroluminescent devices of application examples 1 to 6
Figure RE-GDA0003095152170000172
As can be seen from the data in Table 2, 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 4.3-5.0cd/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.
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 (8)

1. An aza-aromatic compound used as a blue fluorescent material is characterized in that the structural formula is as follows:
Figure FDA0002784822440000011
wherein, X1、X2、X3、X4、X5、X6、X7、X8Each independently is CR1；
R1Each independently selected from hydrogen, deuterium, halogen, C (═ O) RX、CN、Si(RX)3、P(＝O)(RX)2、ORX、S(＝O)RX、S(＝O)2RXCarbonyl group, N (R)X)2A linear alkyl or alkoxy group having 1 to 50 carbon atoms, a cycloalkyl group having 3 to 50 carbon atoms, an alkenyl or alkynyl group having 2 to 50 carbon atoms, an aromatic ring system having 6 to 50 aromatic ring atoms, a heteroaromatic ring system having 5 to 50 aromatic ring atoms; wherein R is1The alkyl, alkoxy, alkenyl, alkynyl, aromatic ring systems and heteroaromatic ring systems described in (a) comprise a ring system substituted with one or more R eachXThe group obtained after the group substitution; and R is1The alkyl, alkoxy, alkenyl and alkynyl groups described in (1) further contain one or more CH2Radical is-RXC＝CRX-、-C≡C-、Si(RX)2、C＝O、C＝N RX、-C(＝O)O-、-C(＝O)N RX-、P(＝O)(RX) -O-, -S-, SO, or SO2The radical obtained after substitution;
RXeach independently selected from H, D, F, CN, an alkyl group 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; and R isXThe alkyl, aromatic ring system and heteroaromatic ring system described in (1) include groups each substituted with F or CN.
2. An azaaromatic compound as claimed in claim 1 wherein any adjacent two or more R' s1The linkage forms a cyclic group that includes more than one heteroatom.
3. An azaaromatic compound according to claim 1, having the following specific formula:
Figure FDA0002784822440000021
Figure FDA0002784822440000031
Figure FDA0002784822440000041
4. a polymer of an azaaromatic compound, which is obtained by polymerizing two or more azaaromatic compounds according to any one of claims 1 to 3.
5. The multimer of claim 4, wherein the azaaromatic compounds are linked to each other by a covalent bond or a bridging group of- (Z) x-, wherein Z is B, C, N, O, S, Se, CR2、NR3、AR4R5An aromatic ring system having 6 to 50 aromatic ring atoms, a heteroaromatic ring system having 5 to 50 aromatic ring atoms, or a straight-chain 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;
the A is C, Si or Ge;
the R is2、R3、R4、R5Each independently selected from hydrogen, deuterium, halogen, C (C ═ O) RY、CN、Si(RY)3、P(＝O)(RY)2、ORY、S(＝O)RY、S(＝O)2RYCarbonyl group, N (R)Y)2Any one of an aromatic ring system having 6 to 30 aromatic ring atoms, a heteroaromatic ring system having 5 to 30 aromatic ring atoms, and a linear or cyclic alkyl or alkoxy group having 1 to 20 carbon atoms;
RYeach independently selected from H, D, F, CN, an alkyl group 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; and R isYThe alkyl, aromatic ring system and heteroaromatic ring system described in (1) include groups each substituted with F or CN.
6. The multimer of claim 4 or 5, having a molecular structure as represented by P1-P15:
Figure FDA0002784822440000051
7. an organic electroluminescent device comprising an anode, a cathode and a functional layer between the anode and the cathode, wherein the functional layer comprises the aza-aromatic compound as defined in any one of claims 1 to 3 or the multimer as defined in any one of claims 4 to 6.
8. The organic electroluminescent device according to claim 7, wherein the functional layer is a light-emitting layer, and the azaaromatic compound according to any one of claims 1 to 3 or the multimer according to any one of claims 4 to 6 is used as a host light-emitting material in the light-emitting layer.
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