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CN118638124A - Organic electroluminescent material and device thereof - Google Patents

Organic electroluminescent material and device thereof Download PDF

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Publication number
CN118638124A
CN118638124A CN202311128039.7A CN202311128039A CN118638124A CN 118638124 A CN118638124 A CN 118638124A CN 202311128039 A CN202311128039 A CN 202311128039A CN 118638124 A CN118638124 A CN 118638124A
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substituted
carbon atoms
unsubstituted
organic electroluminescent
compound
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陈少福
戴雷
蔡丽菲
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Guangdong Aglaia Optoelectronic Materials Co Ltd
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Guangdong Aglaia Optoelectronic Materials Co Ltd
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Priority to PCT/CN2024/072899 priority Critical patent/WO2024187953A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/16—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight

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  • Electroluminescent Light Sources (AREA)

Abstract

The invention relates to an organic electroluminescent material and a device thereof. The organic electroluminescent material has a structure represented by formula (1). The organic electroluminescent material provided by the invention has the advantages of high light and electricity stability, low sublimation temperature, low driving voltage, high luminous efficiency, long service life of the device and the like, and can be used as a main material for OLED luminescent devices. Meanwhile, the material has a lower melting point, and is favorable for material evaporation stability as a melting type material. The material has the possibility of being applied to the AMOLED industry as a main body material.

Description

Organic electroluminescent material and device thereof
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound formed by connecting indole and pyrrole condensed aza macrocycles with N heterocycle and similar structures, and an organic electroluminescent device containing the compound.
Background
At present, an organic electroluminescent device (OLED) as a new generation display technology has gained more and more attention in the aspects of display and illumination technologies, and has a very wide application prospect. However, the performance of OLED devices such as luminous efficiency, driving voltage, lifetime, etc. is still in need of continued enhancement and improvement as compared to the market demands.
In general, the OLED device has a basic structure in which various organic functional material films with different functions are interposed between metal electrodes, like a sandwich structure, holes and electrons are injected from both electrodes under the driving of current, and after a certain distance, the holes and electrons are recombined in a light emitting layer and released in the form of light or heat, thereby generating light emission of the OLED. However, the nature of phosphorescent OLEDs is not only determined by the triplet emitters used. It is also important to include other types of materials, such as host materials. The main material has remarkable effects of reducing the driving voltage of the device, improving the luminous efficiency of the device, prolonging the service life of the device and the like. Accordingly, there is a need to continue to develop new host materials to further improve the performance of organic electroluminescent devices.
Patent document 1 (CN 108391433B) describesThe nitrogen heteroaromatic ring structural unit bonded at a specific position of quinazoline or quinoxaline is used as a red light main body material, and the thermal stability and the service life of the material are still to be further improved; patent document 2 (CN 114591341 a) describesThe main material of indolocarbazole structural unit has improved device efficiency and service life; patent document 3 (US 20220289681 A1) describes
The combined red main material of indole condensed aza macrocyclic structural unit and triazine with similar structure is different from the present invention, and the efficiency of the device using the material as main material needs to be further improved; patent document 4 (KR 101877961B 1) describesThe bipolar host material of indolocarbazole with similar structure is used as green host material, and the service life of the device is required to be further improved.
Disclosure of Invention
The invention aims to solve the defects, and provides a compound formed by connecting indole and pyrrole condensed aza macrocycles with N heterocycle and similar structures, and an organic electroluminescent device containing the compound.
The organic electroluminescent material has a structure shown in a formula (1). The organic electroluminescent material provided by the invention has the advantages of high light and electricity stability, low sublimation temperature, low driving voltage, high luminous efficiency, long service life of the device and the like, and can be used as a main material for OLED luminescent devices. Meanwhile, the material has a lower melting point, and is favorable for material evaporation stability as a melting type material. The compound has the possibility of being applied to the AMOLED industry as a main body material.
An organic electroluminescent material having a structure represented by formula (1),
Wherein L is selected from any one of single bond, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C20 heteroaryl;
X 1 to X 3 each independently represent N or CR a, and ring A, ring B and ring C are, identically or differently, selected from aromatic rings having 5 to 18 carbon atoms, or heteroaromatic rings having 3 to 18 carbon atoms;
wherein E has a structure represented by formula (2):
Wherein a 1 to a 5 are the same or different, and a 1 to a 5 are each independently selected from N or CR 1; ; and at least one of a 1 to a 5 is N and at least one is C-CN, represents the point of attachment to formula (1);
wherein R a、Rb、Rc、Rd and R 1 are the same or different at each occurrence and are each independently selected from: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 10 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, substituted or unsubstituted acyl having 0 to 20 carbon atoms, carbonyl, substituted or unsubstituted alkenyl having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted acyl having 0 to 20 carbon atoms, cyano, substituted or unsubstituted sulfonyl having 0 to 20 carbon atoms; or adjacent R a, adjacent Rb, adjacent Rc, and adjacent Rd can be respectively connected to form a ring;
the substitution is substitution by deuterium, halogen, cyano, alkyl of 1-6 carbon atoms, aryl of 6-30 carbon atoms.
Wherein m, n, k are each independently integers from 1 to 4;
the hetero atoms in the heteroaromatic ring, the heteroalkyl group, the heterocyclic group and the heteroaryl group are respectively and independently selected from O, S, N, si, ge or P.
In some embodiments, the organic electroluminescent material has a structure represented by formula (3),
Wherein, each of X 1 to X 3 independently represents N or CR a,Y1 to Y 10, which are the same or different, and each of Y 1 to Y 10 is independently selected from N or CR; ra is consistent with the definition above;
R is identical to the definition of Rb, rc and Rd, and each occurrence is the same or different and is independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 10 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 0 to 20 carbon atoms, substituted or unsubstituted amido having 0 to 20 carbon atoms, substituted or unsubstituted carbonyl having 0 to 20 carbon atoms, substituted or unsubstituted sulfonyl having 0 to 20 carbon atoms, cyano, substituted or unsubstituted sulfonyl having 0 to 20 carbon atoms; adjacent R and adjacent Ra can be respectively connected to form a ring, and the substitution is replaced by deuterium, halogen, cyano, alkyl with 1-6 carbon atoms and aryl with 6-30 carbon atoms.
In some of these embodiments, Y 1 to Y 10 are each independently denoted CR.
In some of these embodiments, two N are contained in a 1 to a 5 in formula (2), and at least one of a 1 to a 5 is C-CN.
In some embodiments, the organic electroluminescent material is one of the structures shown in formulas (4) - (27):
in some of these embodiments, the structure represented by E consists of one of the following formulas (28) - (34):
Wherein A 1 to A 5 in the formulae (28) to (34) are CR 1, and R1 is as defined above.
In some of these embodiments, L is a single bond, a substituted or unsubstituted C6-C10 aryl group.
In some embodiments, L is substituted or unsubstituted phenyl.
In some of these embodiments, R 1 is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms.
In some embodiments, R 1 is selected identically or differently at each occurrence from phenyl, deuterated phenyl, methylphenyl, fluorophenyl, t-butylphenyl, tridecylmethylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, carbazolyl, pyridinyl, pyrimidinyl, 4-cyanophenyl, 3-cyanophenyl, benzophenanthrene.
In some of these embodiments, the organic electroluminescent material is of one of the following formulas, either partially or fully deuterated or fluorinated,
An organic electroluminescent device is characterized by comprising the organic electroluminescent material.
The organic electroluminescent device comprises a luminescent layer, wherein the luminescent layer comprises the organic electroluminescent material.
The material has the advantages of high light and electricity stability, low sublimation temperature, low driving voltage, high luminous efficiency, long service life of the device and the like, and can be used as a main material for OLED luminous devices. Meanwhile, the material has a lower melting point, and is favorable for material evaporation stability as a melting type material. The material has the possibility of being applied to the AMOLED industry as a main body material.
Drawings
Figure 1 is a 1 HNMR spectrum of compound CPD125,
FIG. 2 is a 1 HNMR spectrum of compound CPD 143.
Detailed Description
The compound of the invention, an organic electroluminescent material, has a structure shown in a formula (1),
Wherein L is selected from any one of single bond, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C20 heteroaryl;
X 1 to X 3 each independently represent N or CR a, and ring A, ring B and ring C are, identically or differently, selected from carbocycles having 5 to 18 carbon atoms, or heterocycles having 3 to 18 carbon atoms;
wherein E has a structure represented by formula (2):
Wherein a 1 to a 5 are the same or different selected from the group consisting of N and CR 1; and at least one of a 1 to a 5 is N and at least one is C-CN, represents the point of attachment to formula (1);
Wherein R a、Rb、Rc、Rd and R 1 are, identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 1 to 10 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, substituted or unsubstituted acyl having 0 to 20 carbon atoms, carbonyl, carboxylic acid ester, cyano, hydroxy, mercapto, substituted or unsubstituted sulfonyl having 0 to 20 carbon atoms, and combinations thereof; adjacent substituents R a, R b, R c and R d can be optionally connected to form a ring;
the substitution is substitution by deuterium, halogen, cyano, alkyl of 1-6 carbon atoms, aryl of 6-30 carbon atoms.
Wherein m, n, k are each independently integers from 1 to 4;
the hetero atoms in the heteroaromatic ring, the heteroalkyl group, the heterocyclic group and the heteroaryl group are respectively and independently selected from O, S, N, si, ge or P.
Examples of the groups of the compound represented by the formula (1) are described below.
In the present specification, "the carbon number a to b" in the expression "X group of a carbon number a to b which is substituted or unsubstituted" means the carbon number in the case where the X group is unsubstituted, and does not include the carbon number of the substituent in the case where the X group is substituted.
The C1 to C10 alkyl group is a linear or branched alkyl group, specifically, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group and its isomer, an n-hexyl group and its isomer, an n-heptyl group and its isomer, an n-octyl group and its isomer, an n-nonyl group and its isomer, an n-decyl group and its isomer, and the like, and is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, more preferably a propyl group, an isopropyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group.
Examples of the cycloalkyl group having 3 to 20 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl groups, and preferably cyclopentyl and cyclohexyl groups.
Examples of the C2-C10 alkenyl group include vinyl, propenyl, allyl, 1-butadienyl, 2-butadienyl, 1-hexatrienyl, 2-hexatrienyl, and 3-hexatrienyl, and allyl is preferred.
The C1-C10 heteroalkyl group is a linear or branched alkyl group or cycloalkyl group containing an atom other than hydrocarbon, examples thereof include a mercapto methyl group, a methoxy methyl group, an ethoxy methyl group, a t-butoxy methyl group, N, N-dimethylmethylalkyl, epoxybutanoyl, epoxypentanoyl, epoxyhexanoyl, and the like, preferably methoxymethylalkyl, epoxypentanoyl, and the like.
Specific examples of the aryl group include phenyl, naphthyl, anthracenyl, phenanthryl, naphthacene, pyrenyl, droyl, benzo [ c ] phenanthryl, benzo [ g ] droyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, biphenyl, terphenyl, tetrabiphenyl, and fluoranthenyl, and phenyl and naphthyl are preferable.
As a specific example of the heteroaryl group, examples include pyrrolyl, pyrazinyl, pyridinyl, pyrimidinyl, triazinyl, indolyl, isoindolyl, imidazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, azadibenzofuranyl, azadibenzothienyl, diazadibenzofuranyl, diazadibenzothienyl, benzofuranyl, and benzofuranyl quinolinyl, isoquinolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolinyl, oxadiazolyl, furazanyl, thienyl, benzothienyl, dihydroacridinyl, azacarbazolyl, diazacarbazolyl, quinazolinyl, and the like, preferably pyridyl, pyrimidinyl, triazinyl, dibenzofuranyl dibenzothienyl, azadibenzofuranyl, azadibenzothienyl, and process for preparing the same dibenzothienyl, azadibenzofuranyl, and azadibenzothienyl.
The optional linkage between adjacent substituents R a, R b, R c, R d means that when Rb, rc or Rd groups are attached to adjacent ring atoms on the A, B or C ring, respectively, the Rb, rc or Rd groups on the adjacent ring atoms can be linked to form a ring; when Ra groups are attached to adjacent ring atoms on the ring formed by X1, X2, X3, ra groups on the adjacent ring atoms can be attached to form a ring.
The following examples are merely for the purpose of facilitating understanding of the technical invention and should not be construed as a specific limitation of the invention.
The starting materials and solvents, etc., involved in the synthesis of the compounds of the present invention are available from suppliers well known to those skilled in the art of Alfa, acros, etc.
Compound CPD001 Synthesis
Synthesis of Compound CPD001-3
Compound CPD001-1 (40.00 g,198.78 mmol), CPD001-2 (37.36 g,238.54 mmol), potassium carbonate (54.95 g,397.56 mmol) and ethanol (600 ml) were added to a 1000ml three-neck round bottom flask, purged three times with nitrogen under vacuum, and reacted overnight at 80 ℃. TLC (ethyl acetate: n-hexane=1:5 as developing solvent) was used up to monitor the consumption of starting material CPD 001-1. Cooling to room temperature, and concentrating under reduced pressure at 65deg.C to remove ethanol. 500ml of deionized water was added, and the mixture was thermally slurried at 80℃for 1 hour, suction filtered, and the same operation was repeated once more, and vacuum-dried overnight at 100℃to give CPD001-3 (46.21 g, purity: 99.41%, yield: 85.06%) as a white solid, mass spectrum: 274.10 (M+H).
Synthesis of Compound CPD001-4
Compound CPD001-3 (45.00 g,164.66 mmol) and phosphorus oxychloride (150 ml,397.56 mmol) were added to a 500ml three neck round bottom flask and reacted for 4 hours at 100 ℃. TLC (ethyl acetate: n-hexane=1:5 as developing solvent) was used up to monitor consumption of starting material CPD 001-3. After cooling to room temperature, the phosphorus oxychloride was removed by concentration under reduced pressure at 70 ℃. Adding dichloromethane (500 ml) to dissolve materials, slowly dropwise adding the dichloromethane solution into 1000ml deionized water, stirring at room temperature for 1 hour, standing for separating liquid, and washing an organic phase with deionized water (300 ml x 3); the organic phase was purified by column chromatography on silica gel (300 g,200-300 mesh, ethyl acetate: n-hexane=1:10 as eluent), and after elution, concentrated under reduced pressure at 70 ℃ for 2 hours to give compound CPD001-4 (39.60 g, purity: 99.56%, yield: 82.44%) as a white solid, mass spectrum: 292.64 (M+H).
Synthesis of Compound CPD001
Compound CPD001-5 (20.38 g,61.70 mmol), N, N-dimethylformamide (300 ml) was added to a 500ml three-necked round bottom flask, the mixture was replaced three times with nitrogen under vacuum, 60% by mass of sodium hydride (2.47 g,61.70 mmol) was slowly added with stirring at room temperature, stirring was carried out at room temperature for 30 minutes, then CPD001-4 (15.00 g,51.42 mmol) was slowly added, and finally the mixture was heated to 100℃and reacted overnight. TLC (ethyl acetate: n-hexane=1:10 as developing solvent) was used up to monitor consumption of starting material CPD 001-4. Cooling to room temperature, slowly dripping the reaction solution into 1000ml of deionized water, stirring at room temperature for 1.5 hours, precipitating a large amount of yellow solid, filtering, washing a filter cake by adopting 300ml of deionized water, and drying at 80 ℃ in vacuum for 2 hours; crystallization twice with toluene and methanol gave CPD001 (15.06 g, purity: 99.95%, yield: 50.00%) as a yellow solid. Sublimation purification of 15.06g of CPD001 crude product gave sublimated pure CPD001 (12.51 g, purity: 99.95%, yield: 83.07%), mass spectrum ：586.24(M+H).1H NMR(400MHz,CDCl3)δ8.25-8.14(m,4H),7.89-7.79(m,2H),7.72(dd,J＝15.0,2.9Hz,1H),7.59-7.42(m,8H),7.42-7.36(m,2H),7.21-7.15(m,3H),7.10-7.05(m,2H),7.04-6.97(m,1H).
Synthesis of Compound CPD009
Synthesis of Compound CPD009-2
The synthesis and purification method of the reference compound CPD001-3 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD009-2 (32.55 g, purity: 99.31%, yield: 81.01%), mass spectrum: 324.26 (M+H). Synthesis of Compound CPD009-3
The synthesis and purification method of the reference compound CPD001-4 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD009-3 (27.63 g, purity: 99.59%, yield: 83.33%), mass spectrum: 342.07 (M+H).
Synthesis of Compound CPD009
The synthesis and purification method of the reference compound CPD001 were carried out by changing the corresponding starting material, and yellow solid was obtained as the objective compound CPD009 (14.25 g, purity: 99.94%, yield: 51.66%). Sublimation purification of 14.25g of CPD009 crude product gave sublimated pure CPD009 (11.29 g, purity: 99.94%, yield: 79.23%), mass Spectrometry ：636.22(M+H).1H NMR(400MHz,CDCl3)δ8.65(s,1H),8.49(dd,J＝15.0,3.0Hz,1H),8.21-8.14(m,3H),8.10-8.06(m,1H),8.02-7.98(m,1H),7.86-7.82(m,2H),7.74-7.70(m,1H),7.68-7.47(m,6H),7.45-7.40(m,3H),7.21-7.13(m,3H),7.13-6.97(m,3H).
Synthesis of Compound CPD019
Synthesis of Compound CPD019-4
The compound CPD019-1 (30.00 g,206.67 mmol), CPD019-2 (37.66 g,206.67 mmol), CPD019-3 (37.23 g,620.00 mmol), potassium carbonate (85.69 g,620.00 mmol) and N, N-dimethylformamide (500 ml) were added to a 1000ml three port round bottom flask, purged three times with nitrogen in vacuo and allowed to react overnight at 80 ℃. TLC (ethyl acetate: n-hexane=1:5 as developing solvent) was used up to monitor consumption of both starting materials CPD019-1 and CPD 019-2. After cooling to room temperature, N-dimethylformamide was removed by concentration under reduced pressure at 65 ℃. Adding 500ml of deionized water, carrying out hot pulping for 1 hour at 70 ℃, carrying out suction filtration, washing a filter cake by adopting 500ml of deionized water, washing by adopting 100ml of ethanol, and carrying out vacuum drying at 100 ℃ overnight to obtain a white solid which is a compound CPD019-4 (44.87 g, purity: 99.21%, yield: 62.14%), and carrying out mass spectrometry: 350.12 (M+H).
Synthesis of Compound CPD019-5
The synthesis and purification method of the reference compound CPD001-4 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD019-5 (30.06 g, purity: 99.42%, yield: 80.09%), mass spectrum: 368.12 (M+H).
Synthesis of Compound CPD019
The method for synthesizing and purifying CPD001 as a reference compound was only required to change the corresponding starting material, and CPD019 (17.51 g, purity: 99.93%, yield: 53.85%) as a yellow solid was obtained as a target compound. Sublimation purification of 17.51g of CPD019 crude product gave sublimated pure CPD019 (14.20 g, purity: 99.93%, yield: 81.10%), mass Spectrometry ：662.24(M+H).1H NMR(400MHz,CDCl3)δ8.34-8.26(m,2H),8.22-8.15(m,2H),7.90-7.79(m,4H),7.79 -7.67(m,3H),7.61-7.34(m,10H),7.26-7.11(m,3H),7.11-6.95(m,3H).
Synthesis of Compound CPD033
Synthesis of Compound CPD033-2
The synthesis and purification method of the reference compound CPD019-4 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD033-2 (18.88 g, purity: 99.32%, yield: 65.33%) and mass spectrum: 279.22 (M+H).
Synthesis of Compound CPD033-3
The synthesis and purification method of the reference compound CPD001-4 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD033-3 (15.23 g, purity: 99.55%, yield: 86.78%) and mass spectrum: 297.08 (M+H).
Synthesis of Compound CPD033
The synthesis and purification method of the reference compound CPD001 were carried out by changing the corresponding starting material, and yellow solid was obtained as the objective compound CPD033 (11.44 g, purity: 99.95%, yield: 56.12%). Sublimation purification of 11.44g of crude CPD033 gave sublimated pure CPD033 (8.68 g, purity: 99.95%, yield: 75.88%), mass spectrum ：591.24(M+H).1H NMR(400MHz,CDCl3)δ8.19(dd,J＝7.4,1.5Hz,2H),7.85-7.83(m,2H),7.72(dd,J＝7.5,1.4Hz,1H),7.60-.47(m,4H),7.47-7.42(m,1H),7.40(dd,J＝7.4,1.7Hz,2H),7.24-7.15(m,3H),7.10(t,J＝7.5Hz,1H),7.05(t,J＝7.5Hz,1H),7.01-6.99(m,1H).
Synthesis of Compound CPD053
Synthesis of Compound CPD053-2
Compound CPD001-4 (20.00 g,68.55 mmol), CPD053-1 (10.55 g,75.41 mmol), tetrakis (triphenylphosphine) palladium (3.96 g,3.43 mmol), potassium carbonate (18.95 g,137.11 mmol), tetrahydrofuran (300 ml), deionized water (100 ml) were added to a 1000ml three port round bottom flask, purged three times with nitrogen under vacuum, and the temperature was raised to 65℃for 4 hours. TLC (ethyl acetate: n-hexane=1:10 as developing solvent) was used up to monitor consumption of starting material CPD 001-4. After cooling to room temperature, the solvent was removed by concentration under reduced pressure at 65 ℃. Adding 500ml of dichloromethane to dissolve the material, washing with deionized water (250 ml of 3), separating liquid, and concentrating; the organic phase was purified by column chromatography on silica gel (350 g,200-300 mesh, ethyl acetate: n-hexane=1:20 as eluent), and after elution, concentrated under reduced pressure at 70 ℃ for 2 hours to give compound CPD053-2 (20.90 g, purity: 99.46%, yield: 86.78%) as a white solid, mass spectrum: 352.12 (M+H)
Synthesis of Compound CPD053
The synthesis and purification method of the reference compound CPD001 were carried out by changing the corresponding starting material, and yellow solid CPD053 (21.20 g, purity: 99.93%, yield: 75.06%) was obtained as the objective compound. Sublimation purification of 21.20g of CPD053 crude product gave sublimated pure CPD053 (17.54 g, purity: 99.95%, yield: 82.74%), mass spectrum ：662.13(M+H).1H NMR(400MHz,CDCl3)δ8.41-8.29(m,2H),8.25-8.15(m,2H),7.95-7.90(m,4H),7.88 -7.79(m,2H),7.72(dd,J＝15.0,2.9Hz,1H),7.61-7.45(m,7H),7.45-7.35(m,3H),7.21-7.18(m,3H),7.14-6.97(m,3H).
Synthesis of Compound CPD074
Synthesis of Compound CPD074-2
The synthesis and purification method of the reference compound CPD019-4 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD074-2 (15.23 g, purity: 99.33%, yield: 64.05%) and mass spectrum: 350.22 (M+H).
Synthesis of Compound CPD074-3
The synthesis and purification method of the reference compound CPD001-4 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD074-3 (14.55 g, purity: 99.56%, yield: 81.36%) and mass spectrum: 368.24 (M+H).
Synthesis of Compound CPD074-4
The synthesis and purification method of the reference compound CPD053-2 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD074-4 (15.65 g, purity: 99.46%, yield: 83.25%) and mass spectrum: 428.16 (M+H).
Synthesis of Compound CPD074
The synthesis and purification method of the reference compound CPD001 were carried out by changing the corresponding starting material, and yellow solid CPD074 (16.86 g, purity: 99.94%, yield: 72.11%) was obtained as the objective compound. Sublimation purification of 16.86g of crude CPD074 gave sublimated pure CPD074 (13.30 g, purity: 99.94%, yield: 78.89%), mass Spectrometry ：738.26(M+H).1H NMR(400MHz,CDCl3)δ8.22-8.16(m,2H),8.11(t,J＝2.9Hz,1H),7.98-7.89(m,5H),7.87-7.81(m,2H),7.79-7.66(m,4H),7.63-7.59(m,1H),7.57-7.36(m,10H),7.21-7.13(m,3H),7.13-6.97(m,3H).
Synthesis of Compound CPD089
Synthesis of Compound CPD089-2
The synthesis and purification method of the reference compound CPD053-2 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD089-2 (18.25 g, purity: 99.53%, yield: 84.22%), mass spectrum: 352.16 (M+H).
Synthesis of Compound CPD089
The synthesis and purification method of the reference compound CPD001 were carried out by changing the corresponding starting material, and yellow solid CPD089 (17.47 g, purity: 99.96%, yield: 75.62%) was obtained as the objective compound. Sublimation purification of 17.47g of crude CPD089 gave sublimated pure CPD089 (14.01 g, purity: 99.96%, yield: 80.20%), mass spectrum ：662.23(M+H).1H NMR(400MHz,CDCl3)δ8.40-8.29(m,2H),8.25-8.14(m,3H),7.89-7.80(m,2H),7.80-7.67(m,2H),7.66-7.59(m,2H),7.58-7.35(m,10H),7.25-7.12(m,3H),7.07(dd,J＝14.9,10.4Hz,2H),7.02-6.96(m,1H).
Synthesis of Compound CPD100
Synthesis of Compound CPD100-2
The synthesis and purification method of the reference compound CPD019-4 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD100-2 (19.45 g, purity: 99.42%, yield: 62.96%) and mass spectrum: 292.06 (M+H).
Synthesis of Compound CPD100-3
The synthesis and purification method of the reference compound CPD001-4 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD100-3 (18.08 g, purity: 99.51%, yield: 88.05%), mass spectrum: 310.05 (M+H).
Synthesis of Compound CPD100-5
The synthesis and purification method of the reference compound CPD053-2 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD100-5 (17.06 g, purity: 99.63%, yield: 85.33%), mass spectrum: 353.21 (M+H).
Synthesis of Compound CPD100
The synthesis and purification method of the reference compound CPD001 were carried out by changing the corresponding starting material, and yellow solid CPD100 (18.96 g, purity: 99.93%, yield: 78.09%) was obtained as the objective compound. Sublimation purification of 18.96g of CPD100 crude product gave sublimated pure CPD100 (15.74 g, purity: 99.95%, yield: 83.02%), mass Spectrometry ：663.22(M+H).1H NMR(400MHz,CDCl3)δ9.10(s,1H),8.77-8.64(m,1H),8.33(dt,J＝15.0,3.0Hz,1H),8.25-8.13(m,3H),7.91-7.76(m,3H),7.76 -7.59(m,3H),7.59-7.45(m,5H),7.45-7.34(m,3H),7.22-7.12(m,3H),7.07(dd,J＝14.9,10.4Hz,2H),7.03-6.95(m,1H).
Synthesis of Compound CPD125
Synthesis of Compound CPD125-2
The synthesis and purification method of the reference compound CPD053-2 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD125-2 (17.63 g, purity: 99.40%, yield: 85.23%), mass spectrum: 352.12 (M+H).
Synthesis of Compound CPD125
The synthesis and purification method of the reference compound CPD001 were carried out by changing the corresponding starting material, and yellow solid was obtained as the objective compound CPD125 (15.05 g, purity: 99.96%, yield: 74.63%). Sublimation purification of 15.05g of CPD125 crude product gave sublimated pure CPD125 (12.24 g, purity: 99.96%, yield: 81.33%), mass Spectrometry ：662.23(M+H).1H NMR(400MHz,CDCl3)δ8.01-7.93(m,5H),7.86-7.74(m,6H),7.65(d,J＝7.7Hz,1H),7.55-7.46(m,3H),7.38(t,J＝6.6Hz,3H),7.28-7.22(m,4H),7.20-7.12(m,3H),7.09(d,J＝8.0Hz,1H),6.89(d,J＝8.0Hz,1H).
Synthesis of Compound CPD127
Synthesis of Compound CPD127-2
The synthesis and purification method of the reference compound CPD019-4 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD127-2 (19.89 g, purity: 99.36%, yield: 65.18%) and mass spectrum: 368.11 (M+H).
Synthesis of Compound CPD127-3
The synthesis and purification method of the reference compound CPD001-4 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD127-3 (17.85 g, purity: 99.54%, yield: 85.36%), mass spectrum: 386.08 (M+H).
Synthesis of Compound CPD127-5
The synthesis and purification method of the reference compound CPD053-2 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD127-5 (16.63 g, purity: 99.71%, yield: 82.55%), mass spectrum: 504.08 (M+H).
Synthesis of Compound CPD127
The method for synthesizing and purifying CPD001 as reference compound was only required to change the corresponding starting material, and CPD127 (16.52 g, purity: 99.94%, yield: 72.21%) as a yellow solid was obtained as the objective compound. 16.52g of CPD127 crude product was purified by sublimation to obtain sublimated pure CPD127 (12.99 g, purity: 99.95%, yield: 78.64%), mass spectrum ：814.30(M+H).1H NMR(400MHz,CDCl3)δ8.34-8.26(m,2H),8.23-8.15(m,2H),8.00-7.88(m,4H),7.88 -7.78(m,3H),7.78-7.69(m,5H),7.56-7.35(m,11H),7.30-7.23(m,2H),7.21-7.18(m,3H),7.13-6.94(m,3H).
Synthesis of Compound CPD143
Synthesis of Compound CPD143-2
The synthesis and purification method of the reference compound CPD019-4 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD143-2 (25.36 g, purity: 99.21%, yield: 61.18%) and mass spectrum: 274.08 (M+H).
Synthesis of Compound CPD143-3
The synthesis and purification method of the reference compound CPD001-4 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD143-3 (24.58 g, purity: 99.61%, yield: 86.41%), mass spectrum: 292.06 (M+H).
Synthesis of Compound CPD143-4
The synthesis and purification method of the reference compound CPD053-2 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD143-4 (20.35 g, purity: 99.68%, yield: 81.41%) and mass spectrum: 352.08 (M+H).
Synthesis of Compound CPD143
The synthesis and purification method of the reference compound CPD001 were carried out by changing the corresponding starting material, and yellow solid CPD143 (14.04 g, purity: 99.95%, yield: 68.57%) was obtained as the objective compound. Sublimation purification of 14.04g of CPD143 crude product gave sublimated pure CPD143 (10.99 g, purity: 99.95%, yield: 78.27%), mass Spectrometry ：662.24(M+H).1H NMR(400MHz,CDCl3)δ8.47(d,J＝7.1Hz,1H),8.05(dd,J＝17.1,8.0Hz,2H),7.85-7.57(m,9H),7.46-7.21(m,11H),7.17-7.12(m,2H),6.89(d,J＝8.0Hz,1H),6.72(d,J＝8.0Hz,1H).
Synthesis of Compound CPD159
Synthesis of Compound CPD159-3
The synthesis and purification method of the reference compound CPD019-4 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD159-3 (18.88 g, purity: 99.21%, yield: 62.74%), mass spectrum: 284.16 (M+H).
Synthesis of Compound CPD159-4
The synthesis and purification method of the reference compound CPD001-4 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD159-4 (17.60 g, purity: 99.50%, yield: 87.54%), mass spectrum: 302.24 (M+H).
Synthesis of Compound CPD159-5
The synthesis and purification method of the reference compound CPD053-2 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD159-5 (16.32 g, purity: 99.75%, yield: 82.95%), mass spectrum: 362.02 (M+H).
Synthesis of Compound CPD159
The synthesis and purification method of the reference compound CPD001 were carried out by changing the corresponding starting material, and yellow solid CPD159 (14.44 g, purity: 99.92%, yield: 67.50%) was obtained as the objective compound. 14.44g of crude CPD159 was purified by sublimation to give sublimated pure CPD159 (11.31 g, purity: 99.95%, yield: 78.32%), mass spectrometry ：672.29(M+H).1H NMR(400MHz,CDCl3)δ8.23-8.16(m,2H),7.94-7.89(m,2H),7.84-7.68(m,2H),7.56-7.45(m,2H),7.45-7.36(m,3H),7.26-7.08(m,4H),7.07-6.98(m,2H).
Synthesis of Compound CPD165
Synthesis of Compound CPD165-2
The synthesis and purification method of the reference compound CPD001-3 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD165-2 (20.63 g, purity: 99.50%, yield: 84.21%), mass spectrum: 292.07 (M+H).
Synthesis of Compound CPD165-3
The synthesis and purification method of the reference compound CPD001-4 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD165-3 (18.95 g, purity: 99.57%, yield: 86.46%), mass spectrum: 310.06 (M+H).
Synthesis of Compound CPD165-5
The synthesis and purification method of the reference compound CPD053-2 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD165-5 (20.08 g, purity: 99.64%, yield: 81.07%) and mass spectrum: 442.13 (M+H).
Synthesis of Compound CPD165
The synthesis and purification method of the reference compound CPD001 were carried out by changing the corresponding starting material, and CPD165 (17.41 g, purity: 99.93%, yield: 66.48%) was obtained as a yellow solid as the objective compound. Sublimation purification of 17.41g of CPD165 crude product gave sublimated pure CPD165 (14.63 g, purity: 99.95%, yield: 84.03%), mass spectrometry ：802.25(M+H).1H NMR(400MHz,CDCl3)δ8.51(dd,J＝14.9,3.0Hz,1H),8.40-8.29(m,2H),8.24-8.11(m,2H),8.04-7.88(m,5H),7.88-7.77(m,2H),7.75-7.69(m,3H),7.62-7.29(m,12H),7.29-7.14(m,2H),7.10-7.02(m,2H).
Synthesis of Compound CPD180
Synthesis of Compound CPD180-1
The synthesis and purification method of the reference compound CPD053-2 only needs to change the corresponding original material, and white solid is obtained as the target compound CPD180-1 (24.16 g, purity: 99.74%, yield: 80.43%), mass spectrum: 428.15 (M+H).
Synthesis of Compound CPD180
The synthesis and purification method of the reference compound CPD001 were carried out by changing the corresponding starting material, and yellow solid CPD180 (18.96 g, purity: 99.94%, yield: 65.36%) was obtained as the objective compound. Sublimation purification of 18.96g of CPD180 crude product gave sublimated pure CPD180 (15.19 g, purity: 99.94%, yield: 80.11%), mass Spectrometry ：788.06(M+H).1H NMR(400MHz,CDCl3)δ8.67(d,J＝2.9Hz,1H),8.54(dd,J＝14.8,3.1Hz,1H),8.42-8.10(m,3H),7.94-7.90(m,2H),7.89-7.77(m,6H),7.76-7.72(m,2H),7.67-7.34(m,13H),7.21-7.15(m,3H),7.10-6.95(m,2H).
Synthesis of Compound CPD220
Synthesis of Compound CPD220
The synthesis and purification method of the reference compound CPD001 were carried out by changing the corresponding starting material, and yellow solid CPD220 (17.53 g, purity: 99.95%, yield: 61.23%) was obtained as the objective compound. Sublimation purification of 17.53g of CPD220 crude product gave sublimated pure CPD220 (13.94 g, purity: 99.95%, yield: 79.52%), mass spectrum ：752.24(M+H).1H NMR(400MHz,CDCl3)δ8.41-8.26(m,3H),8.24-8.14(m,2H),8.02-7.88(m,3H),7.88-7.76(m,3H),7.72(dd,J＝15.0,2.9Hz,1H),7.59-7.44(m,9H),7.44-7.26(m,3H),7.25-7.12(m,3H),7.12-6.98(m,2H).
Application example: fabrication of organic electroluminescent device
50Mm 1.0mm glass substrate with ITO (100 nm) transparent electrode was ultrasonically cleaned in ethanol for 10 minutes, dried at 150 degrees and then subjected to N 2 Plasma treatment for 30 minutes. The washed glass substrate is arranged on a substrate support of a vacuum evaporation device, a hole injection layer with the film thickness of 10nm is formed by evaporation of a compound NDP-9 and a compound HTM1 according to the weight ratio of 97:3, a layer of HTM1 is formed into a film with the film thickness of 60nm by evaporation to serve as the HTL1, a layer of HTM2 is formed into a film with the film thickness of 10nm by evaporation on the HTM1 film to serve as the HTL2, and then a light-emitting layer with the film thickness of 40nm (main material: doping material=97%: 3%) is evaporated on the HTM2 film by adopting a co-evaporation mode, wherein the main materials are respectively the compound of the invention and the comparison compound 1-5. And co-evaporating (35 nm) ETL and LiQ on the light-emitting layer in a weight ratio of 50:50 to form an electron transport material, evaporating LiQ (1 nm) on the electron transport material layer to form an electron injection material, and evaporating Mg/Ag (100 nm, 1:9) in a co-evaporation mode to form a cathode material.
Evaluation:
the above devices were subjected to device performance testing, and the compounds of examples of the present invention and comparative examples 1 to 5 were compared as host materials, respectively, and the luminescence spectrum was tested using a constant current power supply (Keithley 2400), a constant current density flowing through the light emitting element, and a spectroscopic radiation system (CS 2000). The voltage value, current efficiency, spectrum and time for which the test luminance was 95% of the initial luminance were measured simultaneously (LT 95). The results are shown in Table 1 below:
Sublimation temperature contrast: the sublimation temperature is defined as: at a vacuum level of 10- 7 Torr, the sublimation rate is at a temperature corresponding to 1 angstrom per second. The test results were as follows:
Material Sublimation temperature/. Degree.C
CPD001 254
CPD125 261
CPD143 263
Comparative Compound 2 278
Comparative Compound 3 274
Comparative Compound 4 281
As can be seen from the comparison of the data in the above tables, the host material of the present invention has a lower sublimation temperature, which is beneficial for industrial application.
The material has the advantages of high light and electricity stability, low sublimation temperature, low driving voltage, high luminous efficiency, long service life of the device and the like, and can be used as a main material for OLED luminous devices. Meanwhile, the material has a lower melting point, and is favorable for material evaporation stability as a melting type material. The compound has the possibility of being applied to the AMOLED industry as a main body material.

Claims (13)

1. An organic electroluminescent material having a structure represented by formula (1),
Wherein L is selected from any one of single bond, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C20 heteroaryl;
X 1 to X 3 each independently represent N or CR a, and ring A, ring B and ring C are, identically or differently, selected from aromatic rings having 5 to 18 carbon atoms, or heteroaromatic rings having 3 to 18 carbon atoms;
wherein E has a structure represented by formula (2):
Wherein a 1 to a 5 are the same or different, and a 1 to a 5 are each independently selected from N or CR 1; and at least one of a 1 to a 5 is N and at least one is C-CN, represents the point of attachment to formula (1);
Wherein R a、Rb、Rc、Rd、R1 is the same or different at each occurrence and is independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 10 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, substituted or unsubstituted acyl having 0 to 20 carbon atoms, cyano, substituted or unsubstituted sulfonyl having 0 to 20 carbon atoms; adjacent R a, adjacent Rb, adjacent Rc, adjacent Rd can each be joined to form a ring, said substitution being with deuterium, halogen, cyano, alkyl of 1 to 6 carbon atoms, aryl of 6 to 30 carbon atoms,
Wherein m, n, k are each independently integers from 1 to 4;
the hetero atoms in the heteroaromatic ring, the heteroalkyl group, the heterocyclic group and the heteroaryl group are respectively and independently selected from O, S, N, si, ge or P.
2. The organic electroluminescent material as claimed in claim 1, which has a structure represented by formula (3),
Wherein, each of X 1 to X 3 independently represents N or CR a,Y1 to Y 10, which are the same or different, and each of Y 1 to Y 10 is independently selected from N or CR; ra is as defined in claim 1;
R is identical to the definition of Rb, rc, rd in claim 1, R is identical or different at each occurrence and is each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 10 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, substituted or unsubstituted acyl groups having 0 to 20 carbon atoms, carbonyl groups, carboxylic acid groups, substituted or unsubstituted ester groups having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, substituted or unsubstituted sulfinyl groups having 0 to 20 carbon atoms, substituted or unsubstituted sulfonyl groups having 0 to 20 carbon atoms, phosphino groups; adjacent R and adjacent Ra can be respectively connected to form a ring, and the substitution is replaced by deuterium, halogen, cyano, alkyl with 1-6 carbon atoms and aryl with 6-30 carbon atoms.
3. The organic electroluminescent material according to claim 2, wherein Y 1 to Y 10 are each independently denoted CR, R being as defined in claim 2.
4. The organic electroluminescent material according to claim 3, which is one of structures represented by formulae (4) to (27):
5. the organic electroluminescent material according to claim 4, wherein L is a single bond, a substituted or unsubstituted C6-C10 aryl group.
6. The organic electroluminescent material according to claim 5, wherein L is a substituted or unsubstituted phenyl group.
7. The organic electroluminescent material according to any one of claims 1 to 6, wherein a 1 to a 5 in formula (2) contain two N, and at least one of a 1 to a 5 is C-CN.
8. The organic electroluminescent material according to claim 7, wherein the structure represented by E consists of one of the following formulas (28) to (34):
Wherein a 1 to a 5 in formulae (28) to (34) are CR 1, and R1 is as defined in claim 1.
9. The organic electroluminescent material of claim 8, wherein R 1 is a substituted or unsubstituted aryl group having 6-18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3-18 carbon atoms.
10. The organic electroluminescent material as claimed in claim 9, wherein R 1 is selected identically or differently at each occurrence from phenyl, deuterated phenyl, methylphenyl, fluorophenyl, tert-butylphenyl, tridentate methylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, carbazolyl, pyridinyl, pyrimidinyl, 4-cyanophenyl, 3-cyanophenyl, benzophenanthrene.
11. The organic electroluminescent material as claimed in claim 1, which is one of the following structural formulae, or corresponding partially or completely deuterated or fluorinated,
12. An organic electroluminescent device comprising the organic electroluminescent material as claimed in any one of claims 1 to 11.
13. The organic electroluminescent device of claim 12, comprising a light-emitting layer comprising the organic electroluminescent material.
CN202311128039.7A 2023-03-13 2023-09-04 Organic electroluminescent material and device thereof Pending CN118638124A (en)

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