CN112679531A - Boron-containing compound and organic electroluminescent device containing same - Google Patents

Boron-containing compound and organic electroluminescent device containing same Download PDF

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CN112679531A
CN112679531A CN201910991373.2A CN201910991373A CN112679531A CN 112679531 A CN112679531 A CN 112679531A CN 201910991373 A CN201910991373 A CN 201910991373A CN 112679531 A CN112679531 A CN 112679531A
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魏金贝
曾礼昌
李熠烺
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Beijing Eternal Material Technology Co Ltd
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    • H—ELECTRICITY
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Abstract

The present invention relates to a novel organic compound having a structure represented by the following formula (1):
Figure DDA0002238396900000011
rings A, B, C, D, E each independently represent an aromatic or heteroaromatic ring, and adjacent rings may be fused to form a fused ring containing X1Or X2A five-membered ring or a six-membered ring of (a); x1And X2Each independently selected from O, S, N, C, Si; m and n are respectively and independently 0, 1 or 2, R1To R5Are respectively and independentlyOne selected from hydrogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, ester group, silyl, amino, arylamino, heteroarylamino, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl, wherein at least one is represented by formula G. When the compound is used as a light emitting layer material in an OLED device, excellent device performance and stability are shown. The invention also protects the organic electroluminescent device adopting the compound with the general formula.

Description

Boron-containing compound and organic electroluminescent device containing same
Technical Field
The invention relates to a boron-containing organic material, belongs to the technical field of organic luminescent materials, and also relates to an application of the compound in an organic electroluminescent device.
Background
The main way people acquire information is through vision, so that a display device is of great importance in the process of human interaction with information. Organic electroluminescent diodes (OLEDs) have many advantages such as flexibility, self-luminescence, high contrast, large size, and low power consumption, and are one of the mainstream display devices at present.
Among them, the red and green dyes as three primary colors generally contain heavy atoms such as Ir, Pt, etc., theoretically can achieve 100% internal quantum efficiency, have high electroluminescent efficiency and low power consumption, and become the mainstream of the current commercial display devices. However, the chromaticity and lifetime of blue phosphorescent materials are not sufficient for current commercial display. Currently, blue devices still use traditional fluorescent materials to achieve high color purity and long device lifetime.
Recently, researchers of Takuji Hatakeyyama and Junji Kido in Japan reported a series of DABNA-1(Adv. Mater.2016,28, 2777-. Compared with the traditional blue fluorescent dye, the compound has narrower spectrum and high color purity. However, the rigid planar structure also causes the difference between the singlet state and the triplet state energy level to be large, the reverse system crossing from the triplet state to the singlet state is slow, excitons can cause serious efficiency roll-off after being compounded on the dye, and the service life of the device is short. In addition, a rigid structure that is too planar also tends to cause adverse effects such as spectral broadening and red-shift due to too high a doping concentration.
Figure BDA0002238396890000011
The existing organic electroluminescent materials still have a lot of room for improvement in light emitting performance, and there is a need to develop a new light emitting material system to meet the commercialization demand.
Disclosure of Invention
In order to solve the technical problems, the invention provides a novel compound, which belongs to a thermal activation delayed fluorescent material, aryl alkyl is introduced into the structure of the series of compounds, the molecular distance is increased, the molecular accumulation and the Dexter energy transfer are inhibited, and the problem of the efficiency roll-off of an organic electroluminescent device adopting the compound is further improved; in addition, the aryl alkyl has a relatively ideal anchoring effect, can promote molecules to be arranged in parallel with the plane of the OLED substrate, and is beneficial to light extraction so as to improve the luminous efficiency.
The invention provides a novel boron-based organic compound, which has a structure shown in a general formula (1):
Figure BDA0002238396890000021
in the general formula (1):
rings A, B, C, D, E each independently represent an aromatic or heteroaromatic ring, and adjacent rings may be fused to form a fused ring containing X1Or X2A five-membered ring or a six-membered ring of (a);
preferably, ring A is fused to ring C to form a ring containing X1A five-membered ring or a six-membered ring of (a); alternatively, ring B is fused to ring D to form a ring containing X2A five-membered ring or a six-membered ring of (a); alternatively, ring A is fused to ring C to form a ring containing X1With a five-or six-membered ring of (A) and ring B fused with ring D to form a ring containing X2A five-membered ring or a six-membered ring of (a);
X1and X2Each independently selected from O, S, N, C, Si;
m is 0, 1 or 2, when X1When selected from O or S, m is 0; n is 0, 1 or 2, when X2When selected from O or S, n is 0;
R1、R2、R3、R4、R5each independently represents a substituent selected from the group consisting of hydrogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, and halogenOne or the combination of at least two of element, cyano, nitro, hydroxyl, ester group, silane group, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, R1、R2、R3、R4And R5Is formula G;
in formula G: z1Selected from C or Si;
RA、RB、RCare respectively and independently selected from one of C1-C10 chain alkyl, C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, and R isA、RBAnd RCAt least one of the two is substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, and at least one is C1-C10 chain alkyl or C3-C10 cycloalkyl.
When the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, carbonyl, C1-C12 alkyl, C3-C12 cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic aryl or fused ring aryl, C3-C30 monocyclic heteroaryl or fused ring heteroaryl.
In the present invention, the maximum permissible substituent means that the number of the substituent is the maximum number of substitutions provided that the substituted group satisfies the chemical bond requirement.
In the present specification, the expression of Ca to Cb means that the group has carbon atoms of a to b, and the carbon atoms do not generally include the carbon atoms of the substituents unless otherwise specified.
In the present specification, the expression of the "-" underlined loop structure indicates that the linking site is located at an arbitrary position on the loop structure where the linking site can form a bond.
In the present specification, the substituted or unsubstituted C6-C30 aryl group is preferably a C6-C20 aryl group, and more preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, an indenyl group, a naphthyl group,Fluorenyl and its derivatives, fluoranthenyl, triphenylene, pyrenyl, perylenyl,
Figure BDA0002238396890000031
A group of the group consisting of a phenyl group and a tetracenyl group. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl, and 4-biphenyl; terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes a 1-naphthyl group and a 2-naphthyl group; the anthracene group is selected from 1-anthracene group, 2-anthracene group and 9-anthracene group; the fluorenyl is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from 9,9 '-dimethylfluorene, 9' -spirobifluorene and benzofluorene; the pyrenyl is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracenyl group is selected from the group consisting of 1-tetracenyl, 2-tetracenyl, and 9-tetracenyl.
The hetero atom in the present invention generally means an atom or a group of atoms selected from N, O, S, P, Si and Se, preferably N, O, S. The atomic names given in this disclosure, including their respective isotopes, for example, hydrogen (H) includes1H (protium or H),2H (deuterium or D), etc.; carbon (C) then comprises12C、13C and the like.
In the present specification, the substituted or unsubstituted heteroaryl group having C3 to C30 is preferably a heteroaryl group having C4 to C20, more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, and the like, and specific examples thereof include: furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolocarbazole.
In the present specification, the chain alkyl group having from C1 to C20 is preferably a chain alkyl group having from C1 to C10, more preferably a chain alkyl group having from C1 to C6, and examples thereof include: methyl, ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, isopropyl, isobutyl, tert-butyl and the like.
In the present specification, the cycloalkyl group of C3 to C12 includes monocycloalkyl and polycycloalkyl groups, preferably alkyl groups of C1 to C10 and cycloalkyl groups of C3 to C10.
Further, in the compounds of the general formula of the present invention, the rings A, B, C, D, E are independently selected from a 5-8 membered aryl ring or a 5-8 membered heteroaryl ring; preferably, rings A, B, C, D, E are each independently selected from a 6-membered aryl ring or a 5-membered heteroaryl ring.
Further, in the compound of the general formula of the present invention, the rings A, B, C, D, E are each independently selected from one of substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; preferably, each of the rings A, B, C, D, E is independently selected from the group consisting of substituted or unsubstituted: a benzene ring, a furan ring, a thiophene ring, a naphthalene ring, a phenanthrene ring, or a carbazole ring.
Further, the compound of the general formula of the present invention is selected from the following formula (2):
Figure BDA0002238396890000041
still further, the compounds of the general formula of the present invention are selected from the following formula (3):
Figure BDA0002238396890000042
in formula (3), ring C, D, R1、R2、R3、R4、R5M, n are as defined in the general formula (1), and X is1And X2Each independently selected from O, S or N, and X1And X2At least one of which is N.
Furthermore, the compound of the general formula of the present invention is selected from one of the following formulas (I), (II), (III), (IV), (V), (VI), (VII) or (VIII):
Figure BDA0002238396890000051
most preferably, the compounds of the general formula of the present invention are selected from the following formulae (I), (II) or (III):
Figure BDA0002238396890000052
more preferably, formula G is the following formula G1:
Figure BDA0002238396890000053
in formula G1:
RAand RBAt least one of which is C1-C10 chain alkyl or C3-C10 cycloalkyl, RC1One selected from hydrogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
further preferably, RAAnd RBAt least one of which is selected from the group consisting of 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 or cyclooctyl, RC1Selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, phenyl, naphthyl, anthracenyl, thienyl, pyrrolyl, indolyl, carbazolyl or pyridyl.
Still more preferably, formula G is one of the following formulae a, b, c or d:
Figure BDA0002238396890000061
wherein R is6、R7Respectively and independently selected from one or at least two of hydrogen, deuterium, halogen, C1-C10 chain alkyl and C3-C10 cycloalkylCombining; most preferably, formula G is selected from formula a or formula c.
Further preferably, R is as defined above6、R7Each independently selected from hydrogen, or each independently selected from one of the following groups:
Figure BDA0002238396890000062
most preferably, said R6、R7Each independently selected from hydrogen.
Further preferably, in the compound of the general formula (VI) of the present invention, R is1、R2、R3、R4、R5Each independently selected from hydrogen, or each independently selected from one of the following groups:
Figure BDA0002238396890000063
preferred structures of the compounds of the present invention include the following specific compounds M1-M140, but are not limited to these compounds:
Figure BDA0002238396890000071
Figure BDA0002238396890000081
Figure BDA0002238396890000091
Figure BDA0002238396890000101
Figure BDA0002238396890000111
Figure BDA0002238396890000121
as another aspect of the present invention, there is also provided a use of the compound as described above in an organic electroluminescent device. In particular, the organic electroluminescent element is preferably used as a material for a light-emitting layer, more preferably as a material for a light-emitting layer in an organic electroluminescent element, and particularly as a light-emitting dye.
As still another aspect of the present invention, there is also provided an organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer contains a compound of the general formula (1), (2) or (3) as described above or a compound having a structure represented by M1-M140 as described above.
Specifically, one embodiment of the present invention provides an organic electroluminescent device including a substrate, and a first electrode, a plurality of light-emitting functional layers, and a second electrode sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is arranged between the hole transport layer and the electron transport layer; wherein the light-emitting layer contains a compound represented by the general formula (1), (2) or (3) or a compound represented by the formula M1-M140.
The invention also discloses a display screen or a display panel, wherein the display screen or the display panel adopts the organic electroluminescent device; preferably, the display screen or the display panel is an OLED display.
The invention also discloses electronic equipment, wherein the electronic equipment is provided with a display screen or a display panel, and the display screen or the display panel adopts the organic electroluminescent device.
The OLED device prepared by the compound has low starting voltage, high luminous efficiency and better service life, and can meet the requirements of current panel manufacturing enterprises on high-performance materials.
The specific reason why the above-mentioned compound of the present invention is excellent as a material for a light-emitting dye and/or a sensitizer in a light-emitting layer in an organic electroluminescent device is not clearly understood, and it is presumed that the following reasons are possible:
1. the boron atom contained in the compound has resonance effect with the nitrogen atom in the same ring, so that the series of materials have the characteristics of narrow spectrum and thermal activation delayed fluorescence emission.
2. The series of materials contain aryl substituted quaternary carbon and the like, so that the molecular distance can be further increased while the transmission capability is ensured, quenching caused by accumulation is inhibited, the efficiency roll-off is further reduced, and the service life of the device is prolonged.
In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
The specific production method of the above-mentioned novel compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the production method of the present invention is not limited to these synthesis examples.
It should be noted that the method and materials for obtaining the compound are not limited to the synthetic methods and materials used in the present invention, and those skilled in the art may select other methods or routes to obtain the compound proposed in the present invention. The compounds of the synthetic methods not mentioned in the present invention are all starting products obtained commercially or are self-made by these starting products according to known methods.
The solvents and reagents used in the present invention, such as methylene chloride, petroleum ether, ethanol, tert-butyl-ben, boron tribromide, carbazole, diphenylamine and other chemical reagents, can be purchased from domestic chemical product markets, such as reagents from national drug group, TCI, shanghai Bide medical company, Bailingwei reagent company, and the like.
The synthesis of the compounds of the present invention is briefly described below.
Synthetic examples
Representative synthetic route:
Figure BDA0002238396890000141
analytical testing of intermediates and compounds in the present invention uses an abciex mass spectrometer (4000 QTRAP).
Synthesis example 1: synthesis of M1
Figure BDA0002238396890000142
Synthesis of intermediate M1-1:
1, 3-dibromo-5- (2-phenylprop-2-yl) benzene (35.2g, 100mmol), diphenylamine (41.7g, 250mmol), Pd were added at room temperature2(dba)3(0.92g, 1mmol), s-Phos (0.82g, 2mmol), sodium t-butoxide (24g, 250mmol), xylene (500ml) were added to a 1L single-necked flask, replaced with nitrogen three times, and heated to 130 ℃ for reaction overnight. The reaction solution was cooled to room temperature, the reaction system was concentrated and extracted with dichloromethane, washed with a large amount of water, the organic phase was dried and concentrated to conduct column chromatography (PE: DCM ═ 20:1) to obtain 42.4g of crude product, and n-hexane was boiled with heating to obtain 33.1g of white solid with a yield of 62.4%.
Mass spectrometric analysis determined molecular ion mass: 530.29 (theoretical value: 530.27).
Synthesis of compound M1:
m1-1(5.3g, 10mmol) was added to a 250ml three-necked flask, p-tert-butylbenzene (80ml) was added, the reaction system was cooled to-20 ℃ after stirring for 20 minutes, 15mmol of tert-butyllithium was added, and stirring was continued for 30 minutes while maintaining the low temperature. Then gradually heating to 90 ℃ and continuously heating for 3 h. Finally, the temperature of the reaction system is reduced to-20 ℃ again, boron tribromide (5.1g, 20mmol) is added under the protection of nitrogen, and diisopropylethylamine (13g, 80mmol) is added after stirring for 30 minutes. Finally, the reaction system is heated to 110 ℃ and reacted for 12 h. After the reaction was cooled to room temperature, the organic phase was spin-dried under reduced pressure. Ethyl acetate (200ml) was extracted three times, and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase is concentrated with silica gel and chromatographed (PE: DCM 100:1) to give 2.1g of crude product, which is recrystallized from toluene/n-hexane to give 0.95g of yellow solid, 17.6% yield.
Mass spectrometric analysis determined molecular ion mass: 538.22 (theoretical value: 538.26).
Synthesis example 2: synthesis of M6
The synthesis method was similar to that of M1, except that diphenylamine was replaced with an equal amount of bis (4-tert-butylphenyl) amine to give compound M6 in a yield of 15.1%, molecular ion mass determined by molecular mass spectrometry: 762.49 (theoretical value: 762.51).
Synthesis example 3: synthesis of M37
Figure BDA0002238396890000151
Synthesis of intermediate M37-1:
(1- (3, 5-dibromophenyl) ethane-1, 1-diphenyl) diphenyl (41.4g, 100mmol), bis (4-tert-butylphenyl) amine (90.0g, 320mmol), Pd were reacted at room temperature2(dba)3(2.8g, 3mmol), s-Phos (1.2g, 3mmol), sodium t-butoxide (33.6g, 350mmol), xylene (1200ml) were added to a 2L single neck flask, replaced with nitrogen three times, and heated to 130 ℃ for reaction overnight. The reaction was cooled to room temperature, extracted with ethyl acetate, washed with copious amounts of water, the organic phase dried and concentrated for column chromatography (PE: DCM ═ 20:1) to afford 66.4g of a white solid in 81.4% yield.
Mass spectrometric analysis determined molecular ion mass: 816.58 (theoretical value: 816.54).
Synthesis of compound M37:
m53-1(8.2g, 10mmol) was added to a 500ml three-necked flask, p-tert-butylbenzene (150ml) was added, the reaction system was cooled to-20 ℃ after stirring for 20 minutes, 15mmol of tert-butyllithium was added, and stirring was continued for 30 minutes while maintaining the low temperature. Then gradually heating to 90 ℃ and continuously heating for 3 h. Finally, the temperature of the reaction system is reduced to-20 ℃ again, boron tribromide (5.1g, 20mmol) is added under the protection of nitrogen, and diisopropylethylamine (13g, 80mmol) is added after stirring for 30 minutes. Finally, the reaction system is heated to 110 ℃ and reacted for 12 h. After the reaction was cooled to room temperature, the organic phase was spin-dried under reduced pressure. Ethyl acetate (200ml) was extracted three times, and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase is concentrated with silica gel and subjected to column chromatography (PE: DCM ═ 40:1) to give 1.9g of crude product, which is recrystallized from toluene/n-hexane to give 1.1g of yellow solid with a yield of 13.3%. Mass spectrometric analysis determined molecular ion mass: 824.54 (theoretical value: 824.52).
Synthesis example 4: synthesis of M49
The synthesis method was similar to that of M37, except that diphenylamine was replaced with an equal amount of bis (3-tert-butylphenyl) amine to give compound M49 in a yield of 15.5%, molecular ion mass determined by molecular mass spectrometry: 816.57 (theoretical value: 816.54).
Synthesis example 5: synthesis of M55
Figure BDA0002238396890000161
Synthesis of intermediate M55-1:
1-bromo-2, 3-dichlorobenzene (22.4g, 100mmol), bis (4- (2-phenylprop-2-yl) phenyl) amine (129.7g, 320mmol), Pd2(dba)3(2.8g, 3mmol), s-Phos (1.2g, 3mmol), sodium t-butoxide (33.6g, 350mmol), xylene (1200ml) were added to a 2L single neck flask, replaced with nitrogen three times, and heated to 130 ℃ for reaction overnight. The reaction was cooled to room temperature, extracted with ethyl acetate, washed with copious amounts of water, the organic phase dried and concentrated for column chromatography (PE: DCM 15:1) to give 60.8g of a white solid in 66.2% yield.
Mass spectrometric analysis determined molecular ion mass: 918.48 (theoretical value: 918.47).
Synthesis of compound M55:
m55-1(9.2g, 10mmol) was added to a 500ml three-necked flask, p-tert-butylbenzene (150ml) was added, the reaction system was cooled to-20 ℃ after stirring for 20 minutes, 15mmol of tert-butyllithium was added, and stirring was continued for 30 minutes while maintaining the low temperature. Then gradually heating to 90 ℃ and continuously heating for 3 h. Finally, the temperature of the reaction system is reduced to-20 ℃ again, boron tribromide (5.1g, 20mmol) is added under the protection of nitrogen, and diisopropylethylamine (13g, 80mmol) is added after stirring for 30 minutes. Finally, the reaction system is heated to 110 ℃ and reacted for 12 h. After the reaction was cooled to room temperature, the organic phase was spin-dried under reduced pressure. Ethyl acetate (200ml) was extracted three times, and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase is concentrated with silica gel and subjected to column chromatography (PE: DCM 40:1) to give 3.2g of crude product, which is recrystallized from toluene/n-hexane to give 2.3g of yellow solid, with a yield of 26.3%. Mass spectrometric analysis determined molecular ion mass: 892.45 (theoretical value: 892.49).
Synthesis example 6: synthesis of M66
The synthesis method was similar to that of M55, except that 1-bromo-2, 3-dichlorobenzene was replaced with an equal amount of 1-bromo-2, 3-dichloro-5-methylbenzene to give compound M66 in 23.5% yield, molecular ion mass determined by molecular mass spectrometry: 906.48 (theoretical value: 906.51).
Synthesis example 7: synthesis of M89
Figure BDA0002238396890000171
Synthesis of intermediate M89-1:
to a 500mL single-necked flask, 3, 6-bis (2-phenylprop-2-yl) carbazole (34.3g, 85mmol), 2-bromo-1, 3-difluorobenzene (7.7g, 40mmol), cesium carbonate (32.6g, 100mmol), N, N-dimethylformamide (350mL) were added at room temperature, and after 3 times of nitrogen substitution, the mixture was heated at 130 ℃ for reaction overnight. After the reaction is stopped, after the reaction product is cooled to room temperature, 500ml of water is added and stirred for 10min, a large amount of white solid is separated out, the filtration is carried out, the filter cake is boiled and washed by ethanol for 2h, the temperature is reduced, the filtration is carried out, and a white solid product 37.4g is obtained, and the yield is 97.6%. Mass spectrometric analysis determined molecular ion mass: 958.42 (theoretical value: 958.39).
Synthesis of compound M89:
m89-1(9.6g, 10mmol) was added to a 500ml three-necked flask, p-tert-butylbenzene (100ml) was added, the reaction system was cooled to-20 ℃ after stirring for 20 minutes, 15mmol of tert-butyllithium was added, and stirring was continued for 30 minutes while maintaining the low temperature. Then gradually heating to 90 ℃ and continuously heating for 3 h. Finally, the temperature of the reaction system is reduced to-20 ℃ again, boron tribromide (5.1g, 20mmol) is added under the protection of nitrogen, and diisopropylethylamine (13g, 80mmol) is added after stirring for 30 minutes. Finally, the reaction system is heated to 110 ℃ and reacted for 12 h. After the reaction was cooled to room temperature, the organic phase was spin-dried under reduced pressure. Ethyl acetate (200ml) was extracted three times, and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase is concentrated with silica gel and subjected to column chromatography (PE: DCM ═ 40:1) to give 1.9g of crude product, which is recrystallized from toluene/n-hexane to give 1.2g of yellow solid with a yield of 20.3%. Mass spectrometric analysis determined molecular ion mass: 888.47 (theoretical value: 888.46).
Synthesis example 8: synthesis of M90
The synthesis procedure was similar to that of M89, except that 2-bromo-1, 3-difluorobenzene was replaced with an equal amount of 2-bromo-1, 3-difluoro-5-methylbenzene to give compound M90 in 19.6% yield, molecular ion mass determined by molecular mass spectrometry: 902.51 (theoretical value: 902.48).
Based on the same inventive concept, the embodiments of the present invention also provide an organic electronic light emitting device including the compound of the above embodiment. An example of an OLED as an organic electroluminescent device is illustrated below, but it is to be understood that the following detailed description is not a limitation of the present invention, and those skilled in the art can expand the following detailed description to be applied to other organic electroluminescent devices.
In an embodiment, the OLED comprises a first electrode and a second electrode, and several layers of organic material between the electrodes. The organic material layer may be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) may be used2) And transparent conductive oxide materials such as zinc oxide (ZnO), and any combination thereof. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as compounds shown below in HT-1 to HT-34; or any combination thereof.
Figure BDA0002238396890000181
Figure BDA0002238396890000191
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-34 described above, or one or more compounds of HI1-HI3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI1-HI3 described below.
Figure BDA0002238396890000201
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent host material may be selected from, but not limited to, the combination of one or more of BFH-1 through BFH-13 listed below.
Figure BDA0002238396890000202
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may have a multilayer structure including at least one of an electron injection layer ((EIL)), an electron transport layer ((ETL)), and a hole blocking layer ((HBL)).
In a specific example, the electron transport layer material may be selected from, but is not limited to, a combination of one or more of ET-1 through ET-57 listed below.
Figure BDA0002238396890000211
Figure BDA0002238396890000221
Figure BDA0002238396890000231
In one example, an electron injection layer may be further included in the device between the electron transport layer and the cathode, and the electron injection layer may be made of materials including, but not limited to, one or more of the following: LiQ, LiF, NaCl, CsF, Li2O、Cs2CO3BaO, Na, Li and/or Ca.
Device example 1
In example 1, the device structure is as follows:
ITO(150nm)/HI-2(10nm)/HT-2(40nm)/BFH-4:M1(30nm，5wt％)/ET-59(30nm)/LiF(1nm)/Al(150nm)。
the preparation process of the organic electroluminescent device is as follows: glass plates coated with ITO (thickness 150nm) transparent conductive layers were sonicated in commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～1×10-4Pa, performing vacuum evaporation on the anode layer film to obtain HI-2 and HT-2 which are respectively used as a hole injection layer and a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10nm and 40nm respectively;
and vacuum evaporating BFH-4 on the hole transport layer: m1(30nm, 5% wt)' as the luminescent layer of the organic electroluminescent device, the evaporation rate is 0.1nm/s, and the total film thickness is 30 nm; wherein "5% wt" means that the doping ratio of the dye, i.e., the mass part ratio of the host material to M1, is 95: 5.
Vacuum evaporating ET-59 on the luminescent layer to be used as an electron transport layer of the organic electroluminescent device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 30 nm;
and (3) evaporating LiF with the thickness of 0.5nm as an electron injection layer and Al with the thickness of 150nm as a cathode on the electron transport layer in vacuum.
Device examples 2-12 and comparative examples 1-2 were made in the same manner as in device example 1 except that the dye M1 was replaced with the compounds M3, M6, M14, M31, M44, M49, M55, M76, M81, M106 and M108 of the present invention, or M1 was replaced with the compounds DABAN-1 and R1 of the prior art.
Figure BDA0002238396890000241
The organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the driving voltage, current efficiency and lifetime of the organic electroluminescent devices prepared in examples 1 to 12 and comparative examples 1 to 2 were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 1000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the efficiency roll-off is the ratio of (efficiency at maximum brightness minus efficiency at specified brightness) to the maximum efficiency; the life test of LT95 is as follows: using a luminance meter at 1000cd/m2The luminance drop of the organic electroluminescent device was measured to 950cd/m by maintaining a constant current at luminance2Time in hours. Specific performance data are detailed in table 1 below.
TABLE 1
Figure BDA0002238396890000242
Figure BDA0002238396890000251
As can be seen from table 1 above, when the compound of the present invention is used as a dye, compared to the comparative examples using the prior art compounds DABAN-1 and R1, the device using the compound of the present invention has a significantly improved lifetime, relatively higher luminous efficiency, reduced roll-off efficiency, and excellent device performance. This is because DABAN-1 in the prior art is too planar and densely packed, which causes severe quenching, and thus lower efficiency and severe roll-off of the device. And the steric hindrance of three benzene rings at the B para position in the R1 is too high, so that the carrier transmission performance is poor, and the device efficiency is reduced.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.

Claims (14)

1. A compound of the formula (1):
Figure FDA0002238396880000011
in formula (1):
rings A, B, C, D, E each independently represent an aromatic or heteroaromatic ring, and adjacent rings may be fused to form a fused ring containing X1Or X2A five-membered ring or a six-membered ring of (a);
preferably, ring A is fused to ring C to form a ring containing X1A five-membered ring or a six-membered ring of (a);alternatively, ring B is fused to ring D to form a ring containing X2A five-membered ring or a six-membered ring of (a); alternatively, ring A is fused to ring C to form a ring containing X1With a five-or six-membered ring of (A) and ring B fused with ring D to form a ring containing X2A five-membered ring or a six-membered ring of (a);
X1and X2Each independently selected from O, S, N, C, Si;
m is 0, 1 or 2, when X1When selected from O or S, m is 0; n is 0, 1 or 2, when X2When selected from O or S, n is 0;
R1、R2、R3、R4、R5each independently represents a single substituent to the maximum allowable substituent, and is independently selected from one or the combination of at least two of hydrogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, ester group, silane group, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, R1、R2、R3、R4And R5Is formula G;
in formula G:
Z1selected from C or Si;
RA、RB、RCare respectively and independently selected from one of C1-C10 chain alkyl, C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, and R isA、RBAnd RCAt least one of the two is substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, and at least one is C1-C10 chain alkyl or C3-C10 cycloalkyl;
when the above groups have substituents, the substituents are selected from one or a combination of at least two of halogen, cyano, carbonyl, C1-C12 alkyl, C3-C12 cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic aryl or fused ring aryl, C3-C30 monocyclic heteroaryl or fused ring heteroaryl.
2. The compound of formula (la) according to claim 1, wherein the rings A, B, C, D, E are each independently selected from a 5-8 membered aryl ring or from a 5-8 membered heteroaryl ring;
preferably, rings A, B, C, D, E are each independently selected from a 6-membered aryl ring or a 5-membered heteroaryl ring.
3. The compound of formula (la) according to claim 1, wherein the rings A, B, C, D, E are each independently selected from one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
preferably, each of the rings A, B, C, D, E is independently selected from the group consisting of substituted or unsubstituted: a benzene ring, a furan ring, a thiophene ring, a naphthalene ring, a phenanthrene ring, or a carbazole ring.
4. A compound of formula (la) according to claim 1, represented by the following formula (2):
Figure FDA0002238396880000021
in formula (2), ring C, D, X1、X2、R1、R2、R3、R4、R5M and n are as defined in the general formula (1).
5. The compound of the general formula (la) according to claim 1 or 4, represented by the following formula (3):
Figure FDA0002238396880000031
in formula (3), ring C, D, R1、R2、R3、R4、R5M, n are as defined in the general formula (1), and X is1And X2Each independently selected from O, S or N, and X1And X2At least one of which is N.
6. A compound of general formula (I), (II), (III), (IV), (V), (VI), (VII) or (VIII) according to claim 1 or 5:
Figure FDA0002238396880000032
wherein R is1、R2、R3、R4、R5Is the same as defined in the general formula (1).
7. A compound of formula (I) or (II) or (III) according to claim 1 or 5:
Figure FDA0002238396880000033
wherein R is1、R2、R3、R4、R5Is the same as defined in the general formula (1).
8. A compound of formula i according to any one of claims 1 to 7 wherein the formula G is formula G1:
Figure FDA0002238396880000041
in formula G1:
RAand RBAt least one of which is C1-C10 chain alkyl or C3-C10 cycloalkyl,
RC1selected from hydrogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3COne of C30 heteroaryl;
preferably, RAAnd RBAt least one of which is selected from the group consisting of 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 or cyclooctyl, RC1Selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, phenyl, naphthyl, anthracenyl, thienyl, pyrrolyl, indolyl, carbazolyl or pyridyl.
9. A compound of formula (la) according to any one of claims 1 to 8, wherein G is one of the following formulae a, b, c or d:
Figure FDA0002238396880000042
wherein R is6、R7Independently selected from one or the combination of at least two of hydrogen, deuterium, halogen, C1-C10 chain alkyl and C3-C10 naphthenic base;
preferably, formula G is selected from formula a or formula c.
10. A compound of formula (la) according to claim 9, wherein R is6、R7Each independently selected from hydrogen, or each independently selected from one of the following groups:
Figure FDA0002238396880000051
preferably, R is6、R7Each independently selected from hydrogen.
11. A compound of formula (la) according to any one of claims 1 to 9, wherein R is1、R2、R3、R4、R5Each independently selected from hydrogen, or each independently selected from one of the following groups:
Figure FDA0002238396880000052
12. a compound of formula (la) according to claim 1, selected from the compounds of the following specific structures:
Figure FDA0002238396880000053
Figure FDA0002238396880000061
Figure FDA0002238396880000071
Figure FDA0002238396880000081
Figure FDA0002238396880000091
Figure FDA0002238396880000101
13. use of a compound as claimed in any one of claims 1 to 12 as a light-emitting layer material in an organic electroluminescent device.
14. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between said first and second electrodes, characterized in that said organic layers comprise at least one compound according to any one of claims 1 to 12;
preferably, the organic functional layer comprises a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light emitting layer is disposed between the hole transport layer and the electron transport layer, wherein the light emitting layer contains the compound according to any one of claims 1 to 12.
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