CN108690060B - Aromatic ring compounds used as electroluminescent material and light-emitting device thereof - Google Patents

Aromatic ring compounds used as electroluminescent material and light-emitting device thereof Download PDF

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CN108690060B
CN108690060B CN201810507847.7A CN201810507847A CN108690060B CN 108690060 B CN108690060 B CN 108690060B CN 201810507847 A CN201810507847 A CN 201810507847A CN 108690060 B CN108690060 B CN 108690060B
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aromatic ring
light
layer
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陈跃
丰佩川
胡灵峰
杨阳
王培祥
张国选
刘鹏
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Yantai Xianhua Photoelectric Material Research Institute Co ltd
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Abstract

The invention relates to a polyaromatic ring compound used as electroluminescent material and a luminescent device thereof, which have a molecular structure shown as a formula (1),
Figure DDA0001671657890000011
the multiple aromatic ring compound provided by the invention connects small conjugated aromatic rings into the multiple aromatic ring compound through elements or groups such as boron, phosphorus and the like, the HOMO-LUMO energy difference of the compound is easy to adjust, so that the adjustment of the color of emitted light is realized, and the material can emit light in a dark blue to green range and is suitable for being used as a luminescent material in an organic electroluminescent device.

Description

Aromatic ring compounds used as electroluminescent material and light-emitting device thereof
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a polycyclic aromatic compound and a light-emitting device thereof.
Background
The organic electroluminescence technology, as a new display technology, has the advantages of high brightness, low driving voltage, high luminous efficiency, simple structure, large viewing angle and the like, and has very wide application prospect. At present, in red, green and blue three-primary-color materials used for preparing full-color organic light-emitting diodes, red light materials and green light materials basically meet the industrial requirements, and blue light materials are still far away from industrial application in the aspects of fluorescence efficiency, color purity, service life, brightness and the like, so that the red light materials and the green light materials become technical problems in the industry.
At present, carbazole, anthracene, comb, perylene, fluorene, styrene and the like are mainly used as core structures of blue light materials. A new blue light material core structure is searched, and a novel blue light emitting material is further designed, so that the blue light emitting material has important significance for improving and enhancing the performance of a blue light OLED material.
As a blue light material, the energy difference between the Highest Occupied Molecular Orbital (HOMO) and the Lowest Unoccupied Molecular Orbital (LUMO) is large enough to emit blue light of high energy. The aromatic ring system with small conjugation has very large HOMO-LUMO energy difference, but the redox stability of the aromatic ring system is not good enough, and the emission spectrum has more large shoulder peaks, so that the color purity is not good enough; while the aromatic system with large conjugated ring has better oxidation-reduction stability, but is easy to generate smaller HOMO-LUMO energy difference and low-energy triplet excited state, and is not suitable for being used as a blue light emitting material.
Disclosure of Invention
Aiming at the defects of the existing blue light materials, the invention designs and synthesizes a series of polyaromatic ring compounds, and the materials can maintain larger HOMO-LUMO energy level and simultaneously enlarge conjugation degree to enhance the redox stability of the polyaromatic ring compounds by connecting a plurality of small aromatic ring structures, and further can adjust the HOMO-LUMO energy level difference by changing the structures and substituents of the aromatic rings, so that the emitted light is changed into sky blue light and green light from blue light.
The technical scheme for solving the technical problems is as follows:
a polyaromatic ring compound used as electroluminescent material has a molecular structure shown in formula (1):
Figure BDA0001671657870000021
wherein, X1、X2And X3Each independently is B, C or N;
Y1and Y2Each independently is N, O, S, NR1Or CR2；
R1And R2Each independently selected from hydrogen, deuterium, halogen, C (═ O) RX、CN、Si(RX)、P(＝O)(RX)、ORX、S(＝O)RX、S(＝O)2RXA carbonyl group, an 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 said alkyl, alkoxy, alkenyl, alkynyl, aromatic and heteroaromatic rings are each optionally substituted with one or more RXThe group obtained after the group substitution; the alkyl, alkoxy, alkenyl and alkynyl also include one or more CH2Radical is-RXC＝CRX-、-C≡C-、Si(RX)2、C＝O、C＝NRX、-C(＝O)O-、-C(＝O)NRX-、P(＝O))(RX) -O-, -S-, SO or SO2The radical obtained after substitution;
the R isXEach independently selected from the group consisting of hydrogen, deuterium, halogen, CN, substituted or unsubstituted alkyl groups having from 1 to 50 carbon atoms, substituted or unsubstituted aromatic ring systems having from 6 to 50 aromatic ring atoms, and substituted or unsubstituted heteroaromatic ring systems having from 5 to 50 aromatic ring atoms;
z is B, P, P-O, P-S, Al, Ga, SiR3Or GeR4Said R is3And R4Each independently is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy;
the a1 ring, the a2 ring, the A3 ring, and the a4 ring are each independently a substituted or unsubstituted aromatic ring system, a substituted or unsubstituted heteroaromatic ring system.
Further, Y1With ring A1, and/or Y2The ring to which A2 is attached forms a cyclic structure containing at least one heteroatom, preferably B, N, S, O and Se.
Further, ring a1 shares a ring edge with ring a2 to form a fused ring structure, ring A3 shares a ring edge with ring a4 to form a fused ring structure, and the fused ring structures of both are independently selected from the following structures:
Figure BDA0001671657870000031
wherein X4、X5、X6、X7、X8、X9、X10、X11、X12、X13、X14、X15、X16、X17、X18、X19、X20、X21、X22、X23、X24、X25、X26、X27、X28、X29、X30、X31、X32、X33、X34、X35、X36And X37Each independently is B, C or N;
Y3、Y4、Y5、Y6、Y7、Y8、Y9、Y10、Y11、Y12、Y13、Y14、Y15、Y16、Y17、Y18、Y19、Y20、Y21、Y22、Y23、Y24、Y25、Y26、Y27、Y28、Y29、Y30、Y31、Y32、Y33、Y34、Y35、Y36、Y37、Y38、Y39、Y40、Y41、Y42、Y43、Y44、Y45、Y46、Y47、Y48、Y49、Y50、Y51、Y52、Y53、Y54、Y55、Y56、Y57、Y58、Y59、Y60、Y61、Y62、Y63、Y64、Y65、Y66、Y67、Y68、Y69、Y70、Y71、Y72、Y73、Y74、Y75、Y76、Y77、Y78、Y79、Y80、Y81and Y82Each independently is N, O, S, NR5Or CR6；
R5And R6Each independently selected from hydrogen, deuterium, halogen, C (═ O) RX、CN、Si(RX)、P(＝O)(RX)、ORX、S(＝O)RX、S(＝O)2RXA carbonyl group, an 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 said alkyl, alkoxy, alkenyl, alkynyl, aromatic and heteroaromatic rings are each optionally substituted with one or more RXThe group obtained after the group substitution; the alkyl, alkoxy, alkenyl and alkynyl also include one or more CH2Radical is-RXC＝CRX-、-C≡C-、Si(RX)2、C＝O、C＝NRX、-C(＝O)O-、-C(＝O)NRX-、P(＝O))(RX) -O-, -S-, SO or SO2The radical obtained after substitution;
the R isXEach independently selected from the group consisting of hydrogen, deuterium, halogen, CN, substituted or unsubstituted alkyl groups having from 1 to 50 carbon atoms, substituted or unsubstituted aromatic ring systems having from 6 to 50 aromatic ring atoms, and substituted or unsubstituted heteroaromatic ring systems having from 5 to 50 aromatic ring atoms.
Further, the above-mentioned polyaromatic ring compound has a molecular structure shown below:
Figure BDA0001671657870000051
Figure BDA0001671657870000061
Figure BDA0001671657870000071
Figure BDA0001671657870000081
Figure BDA0001671657870000091
Figure BDA0001671657870000101
the invention also claims polymers polymerized from two or more of the above-described polyaromatic ring compounds.
Further, the aromatic ring compounds pass through- (W)xA bridging group of (A), said W is B, C, N, O, S, Se, Si, P, CR7、NR8、AR9R10Any one of a disubstituted or polysubstituted aromatic ring system and a disubstituted or polysubstituted heteroaromatic ring system; x is more than or equal to 1 and is an integer, and x W are independent;
wherein A is C, Si or Ge; r7、R8、R9、R10Each independently hydrogen, deuterium, halogen, C (═ O) RX、CN、Si(RX)、P(＝O)(RX)、ORX、S(＝O)RX、S(＝O)2RXA carbonyl group, an 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 said alkaneThe radicals, alkoxy, alkenyl, alkynyl, aromatic and heteroaromatic rings each being interrupted by one or more RXThe group obtained after the group substitution; the alkyl, alkoxy, alkenyl and alkynyl also include one or more CH2Radical is-RXC＝CRX-、-C≡C-、Si(RX)2、C＝O、C＝NRX、-C(＝O)O-、-C(＝O)NRX-、P(＝O))(RX) -O-, -S-, SO or SO2The radical obtained after substitution;
the R isXEach independently selected from the group consisting of hydrogen, deuterium, halogen, CN, substituted or unsubstituted alkyl groups having from 1 to 50 carbon atoms, substituted or unsubstituted aromatic ring systems having from 6 to 50 aromatic ring atoms, and substituted or unsubstituted heteroaromatic ring systems having from 5 to 50 aromatic ring atoms.
An aromatic ring system as referred to in the context of the present invention means an aromatic ring comprising 6 to 50 ring atoms, which does not comprise any heteroatoms as aromatic ring atoms. Thus, an aromatic ring system in the context of the present invention does not comprise any heteroaryl groups. An aromatic ring system in the context of the present invention refers to a system which does not necessarily contain only aryl groups, but may also be a system in which a plurality of aryl groups are bonded by single bonds or non-aromatic units. For example, systems in which two or more aromatic groups are linked by a straight-chain alkyl, cycloalkyl, alkenyl, alkynyl or silyl group, B, C, Si, N, O or S atom or the like, such as systems of 9 '9-spirobifluorene, 9' 9-diarylfluorene, triarylamine, diaryl ether, stilbene, triphenylsilane, are likewise considered to be included in the aromatic ring systems in the context of the present invention. Furthermore, systems in which two or more aryl groups are connected to each other by single bonds are also considered to be comprised within an aromatic ring system in the context of the present invention, e.g. systems such as biphenyl, terphenyl, phenylbinaphthyl.
A heteroaromatic ring system in the context of the present invention means a ring system comprising 5 to 50 ring atoms, and at least one of which is a heteroatom. The heteroatom of the heteroaromatic ring system is preferably selected from B, N, O or S. Heteroaromatic ring systems conform to the definition of aromatic ring systems above, but have 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.
An aryl group in the context of the present invention is meant to contain 6 to 50 aromatic ring atoms, none of which are heteroatoms. An aryl group in the context of the present invention means a simple aromatic ring, i.e. benzene, or a fused aromatic ring, such as naphthalene, phenanthrene or anthracene, etc. A fused aromatic ring in the context of the present application consists of two or more simple aromatic rings fused to each other. Fused between rings means here that the rings share at least one edge with each other.
Heteroaryl groups in the context of the present invention are meant to contain 5 to 40 aromatic ring atoms, at least one of which is a heteroatom. The heteroatom of the heteroaryl group is preferably B, N, O or S. Heteroaryl groups in the context of the present invention refer to simple heteroaromatic rings, such as pyridine, furan, thiophene, pyrimidine, etc., or fused heteroaromatic rings, such as quinoline, carbazole, benzofuran, dibenzothiophene, etc. Fused heteroaromatic polycyclic in the context of this application means a group resulting from two or more simple heteroaromatic rings fused to one another being fused to one another, or a group resulting from one or more simple heteroaromatic rings being fused to one or more simple aromatic rings. Fused between rings means that the rings share at least one side with each other.
An aromatic ring system having 6 to 50 ring atoms or a heteroaromatic ring system having 5 to 40 ring atoms refers to groups derived from: the groups mentioned above in the context of aryl and heteroaryl groups, and also biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, indenofluorene, triindene, isotridecyl, spirotriindene, spiroisotridecyl, indenocarbazole or combinations of the aforementioned 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 to be understood as meaning groups which are derived from: benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene,
Figure BDA0001671657870000121
Triphenylene, fluoranthene, benzanthracene, triphenylene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinalin, acridine, phenanthridine.
Alkyl having 2 to 50 carbon atoms, cycloalkyl having 3 to 50 carbon atoms and alkenyl or alkynyl groups having 2 to 50 carbon atoms are in the context of the present invention preferably understood as being 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, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl or octynyl groups, the individual hydrogen atoms in each group or the CH group.2The groups may also be substituted with the above groups.
Alkoxy 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, sec-butylthio, tert-butylthio, n-pentylthio, sec-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, pentakis-ethylthio, tert-butylthio, n-pentylthio, sec-pentylthio, n-hexylthio, cyclohexylthio, 2,2, 2-trifluoroethylthio, vinylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthioCyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio or octynylthio, the individual hydrogen atoms in each radical or CH2The groups may also be substituted with the above groups.
In the context of the present application, the wording that two or more groups together may form a ring is to be understood as two groups being connected to each other by a chemical bond. 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 aromatic ring compound and the polymer thereof provided by the invention have the beneficial effects that:
1) the multi-aromatic ring compound provided by the invention connects small conjugated aromatic rings into the multi-aromatic ring compound through elements or groups such as boron, phosphorus and the like, the HOMO-LUMO of the compound is easy to adjust, and the compound can emit high-quality blue light, sky blue light, green light and the like.
2) The polymer adopts a non-carbon bridge group to connect a small conjugated ring system, so that the strong conjugation between multiple rings can be reduced, the degree of the delocalization of HOMO and LUMO is inhibited, the energy difference of HOMO-LUMO cannot become too small, and the energy level of T1 cannot be too low.
A second object of the present invention is to provide an organic electroluminescent device using the above-mentioned polyaromatic ring compound and multimers thereof as an electroluminescent material, comprising an anode layer, a cathode layer, and a functional layer located between the anode layer and the cathode layer, the functional layer comprising the above-mentioned polyaromatic ring compound or multimer of polyaromatic ring compound.
Further, the functional layer is a light-emitting layer, and the aforementioned polyaromatic ring compound or a multimer of the polyaromatic ring compound serves as a guest light-emitting material in the light-emitting layer.
The organic electroluminescent device provided by the invention has the beneficial effects that: the starting voltage is low, the maximum current efficiency is 4.1-4.9cd/A, blue, sky blue or green light is emitted, and the performance is excellent.
Drawings
FIG. 1 is a schematic structural diagram of an organic electroluminescent device;
FIG. 2 is a graph showing an emission spectrum of application example 1;
FIG. 3 is a graph showing an emission spectrum of application example 2;
FIG. 4 is a graph showing an emission spectrum of application example 3;
FIG. 5 is a graph showing an emission spectrum of application example 4;
FIG. 6 is a graph showing an emission spectrum of application example 5;
FIG. 7 is a graph showing an emission spectrum of application example 6;
FIG. 8 is a graph showing an emission spectrum of application example 7;
FIG. 9 is a graph showing an emission spectrum of application example 8;
in fig. 1, LY1, glass substrate; LY2, anode layer; LY3, hole injection layer; LY4, hole transport layer; LY5, light emitting layer; LY6, electron transport layer; LY7, electron injection layer; LY8, 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 BDA0001671657870000151
(2)
Figure BDA0001671657870000152
the preparation method comprises the following steps:
(1) in a 250mL three-necked flask, R1a 5.0.0 g (20mmol), R2a 4.4.4 g (11mmol), potassium carbonate 3.4g (25mmol), toluene 80mL, ethanol 10mL, deionized water 10mL, nitrogen protection and palladium tetrakistriphenylphosphine Pd (PPh)3)41.2g(0.1mmol), slowly heating to 65 ℃, stirring and refluxing for 18 hours, stopping the reaction, cooling to room temperature, separating, collecting an organic phase, and removing the solvent to obtain an intermediate INT1a 3.4.4 g (7mmol, yield 69%);
(2) under the protection of nitrogen, 100ml of intermediate INT1a 3.4.4 g (7mmol) and o-xylene are added into a 250ml three-neck flask at 0 ℃, 2.9ml of 2.5mol/L n-butyllithium hexane solution is added dropwise, and after the dropwise addition is finished, the temperature is raised to 70 ℃, the stirring is carried out for 4 hours, and then the hexane is distilled off after the temperature is raised to 100 ℃. After cooling to-50 ℃, further 2.1g (8.4mmol) of boron tribromide was added, and then the mixture was warmed to 70 ℃ at room temperature and stirred for 2 hours. The mixture was cooled to 0 ℃ again, 1.79g (13.8mmol) of N, N-diisopropylethylamine was added thereto, and the mixture was stirred at room temperature for 20 minutes, then heated to 120 ℃ and stirred for 2 hours. Cooling the reaction liquid to room temperature, adding ethanol to precipitate a white solid (a product Pa, namely a compound 1), then carrying out suction filtration to obtain a precipitate, and cleaning the crude product by using n-hexane.
Example 2
Synthesis of Compound 2, the reaction equation is as follows:
(1)
Figure BDA0001671657870000161
(2)
Figure BDA0001671657870000162
the specific preparation method refers to example 1, except that in step (1), R1b and R2a are used to react to obtain INT2 b; INT2b generates the product Pb (compound 2) through step (2).
Example 3
Synthesis of Compound 3, the reaction equation is as follows:
(1)
Figure BDA0001671657870000171
(2)
Figure BDA0001671657870000172
the specific preparation method refers to example 1, except that in step (1), R1c and R2a are used to react to generate INT2 c; INT2c generates the product Pc (compound 3) through step (2).
Example 4
Synthesis of Compound 4, the reaction equation is as follows:
(1)
Figure BDA0001671657870000173
(2)
Figure BDA0001671657870000174
the specific preparation method refers to example 1, except that in step (1), R1d and R2a are used to react to generate INT2 d; INT2d produced the product Pd (compound 4) via step (2).
Example 5
Synthesis of compounds 272 and 254, the reaction equation is as follows:
(1)
Figure BDA0001671657870000181
(2)
Figure BDA0001671657870000182
(3)
Figure BDA0001671657870000183
the preparation method comprises the following steps:
(1) step (1) the reaction sequence of step (1) of example 1 was referred to, except that R1b was used to react with R2a to generate INT2 b;
(2) under nitrogen protection, and at 0 ℃, intermediate INT2b 15.86.86 g (30mmol) and benzene 200ml are added to a 500ml three-necked flask, then 18.4ml of a 1.64mol/L hexane solution of n-butyllithium is added dropwise, after the addition is completed, stirring is performed for 2 hours, phosphorus trichloride 2.87ml (33mmol) is added at 0 ℃, then the temperature is raised to 80 ℃, and stirring is performed at the temperature for 1 hour. After removing the solvent under reduced pressure, 1.16g (36mmol) of sulfur and o-dichlorobenzene (300ml) were added thereto, and the mixture was stirred at 80 ℃ for 1 hour, cooled to-95 ℃ and then 27.9g (210mmol) of aluminum trichloride was added thereto, and 12.3g (72mmol) of N, N-diisopropylethylamine was added thereto at 0 ℃ and the mixture was stirred at 100 ℃ for 16 hours. The reaction mixture was cooled to room temperature and then added to a dichloromethane solution of 1, 4-diazabicyclo [2.2.2] octane. The solid product Pe1 (compound 272) precipitated and was then filtered off with suction to give a precipitate, and the crude product was washed with acetonitrile and n-hexane.
(3) Adding 0.52g (3mmol) of m-chloroperbenzoic acid to 1.78g (3mmol) of the product Pe in the step (2) and 230ml of dichloromethane at the temperature of 0 ℃, raising the temperature to room temperature, stirring for 16 hours, adding 15ml of a saturated solution of sodium sulfite and 60ml of water, stirring and filtering to remove insoluble substances, extracting with dichloromethane, combining organic phases, concentrating, and adding a solvent with the volume ratio of 1: 1 as eluent, desolvation under reduced pressure, washing the crude product with methanol to give product Pe2 (compound 254).
Example 6
Synthesis of compounds 273 and 255, the reaction equation is as follows:
(1)
Figure BDA0001671657870000191
(2)
Figure BDA0001671657870000192
(3)
Figure BDA0001671657870000201
the specific production method is the same as that of example 5 except that in step (1), R1c and R1b are used to react to produce INT2c, in step (2), INT2c is used to react to produce Pf1 (compound 273), and in step (3), Pf1 and Pf2 (compound 255) produced by m-chloroperbenzoic acid are used.
Application example of organic electroluminescent device
As shown in fig. 1, the structure of the organic electroluminescent device (OLED) includes a glass substrate LY1, an anode layer LY2, a hole injection layer LY3, a hole transport layer LY4, a light emitting layer LY5, an electron transport layer LY6, an electron injection layer LY7, and a cathode layer LY8, which are sequentially stacked 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 the glass substrate LY1 to serve as a transparent anode layer LY 2;
2) vacuum evaporating NPB (N, N '-di (1-naphthyl) -N, N' -diphenyl-1, 1 '-biphenyl-4-4' -diamine) hole transport material with the thickness of 10nm on the transparent anode layer LY2 as a hole injection layer LY3, wherein the doping amount is 3% of F4-TCNQ (2,3,5, 6-tetrafluoro-7, 7',8,8' -tetracyanoquinodimethane);
3) on the hole injection layer LY3, there was a layer of spiro-TAD (2,2',7,7' -tetrakis (diphenylamino) -9,9' -spirobifluorene) as a hole transport layer LY4 with a thickness of 100 nm;
4) a light-emitting layer LY5 with the thickness of 30nm is vacuum-evaporated on the hole transport layer LY4, a main light-emitting material in the light-emitting layer is CDBP (4,4 ' -N, N ' -dicarbazole-2, 2' -dimethylbiphenyl), wherein 4 wt% of the compound provided by the invention is doped, and the compounds doped in application examples 1-8 are respectively compound 1, 2,3, 4, 254, 255, 272 and 273 of the invention;
5) a layer of TPQ (2,3,5, 8-tetraphenylquinoxaline) with the thickness of 30nm is evaporated on the luminescent layer LY5 in vacuum to be used as an electron transport layer LY 6;
6) vacuum evaporating a Liq layer with the thickness of 1nm on the electron transport layer LY6 to form an electron injection layer LY 7;
7) finally, metal aluminum (Al) with the thickness of 100nm is deposited on the electron injection layer LY7 by adopting a vacuum evaporation film deposition technology to be used as a cathode layer LY8 of the device.
The structural formula of the compound used in the application example is as follows:
Figure BDA0001671657870000211
through the test, the performance test results of the organic electroluminescent devices of application examples 1 to 8 are shown in table 1.
Table 1: performance test result of organic electroluminescent device of application examples 1-8
Figure BDA0001671657870000221
As can be seen from the data in Table 1, the maximum current efficiency of the light-emitting device is 4.1-4.9cd/A and the light emitted by the device is blue, sky blue or green by using the material provided by the invention as the doping material in the light-emitting layer, which indicates that the material provided by the invention is suitable for OLED light-emitting materials.
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 kind of polyaromatic ring compound used as electroluminescent material is characterized in that it has the following molecular structure:
Figure FDA0002454770010000011
2. an organic electroluminescent device comprising an anode layer, a cathode layer and a functional layer disposed between the anode layer and the cathode layer, wherein the functional layer contains any one of the polyaromatic ring compounds of claim 1.
3. The organic electroluminescent device according to claim 2, characterized in that the functional layer is in particular a light-emitting layer.
4. The organic electroluminescent device according to claim 3, wherein any one of the polyaromatic ring compounds of claim 1 is used as a guest light-emitting material in the light-emitting layer.
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