CN108129332B - Fluorene substituted derivative and application thereof - Google Patents
Fluorene substituted derivative and application thereof Download PDFInfo
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Abstract
The invention provides a compound with a general formula as shown in the following formula I:
ar is selected from C6～C50Substituted or unsubstituted aryl, C6～C50Substituted or unsubstituted fused ring aromatic hydrocarbon group of (A), C4～C50Substituted or unsubstituted heteroaryl, C4～C50Substituted or unsubstituted fused heterocyclic aromatic hydrocarbon group of (a); the above heteroaryl and fused heterocyclic aromatic hydrocarbon groups are monocyclic or fused ring aryl groups containing one or more heteroatoms selected from B, N, O, S, P (═ O), Si and P and having 4 to 50 ring carbon atoms; n is 1 or 2; when n is 2, L is selected from the structures represented by formula A, B, C or D below:
when n ═ 1, L is selected from the structures represented by the following formulae E or F:
Description
Technical Field
The present invention relates to a novel organic compound, and more particularly, to an aromatic amine derivative that can be used in an organic electroluminescent device, and also to an organic electroluminescent device using the aromatic amine derivative.
Background
The organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages of self-luminescence, low-voltage direct current drive, full curing, wide viewing angle, light weight, simple composition and process and the like, and compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, has large viewing angle, low power, 1000 times of response speed of the liquid crystal display, and lower manufacturing cost than the liquid crystal display with the same resolution, so the organic electroluminescent device has wide application prospect.
An organic electroluminescent device (OLED) using an organic electroluminescent material can be used in the fields of solid-state light-emitting full-color display, solid-state white light illumination, and the like, and is known as a next-generation novel display and illumination technology. Typically, an OLED device comprises a light-emitting layer and a pair of opposing electrodes sandwiching the layer. When an electric field is applied between the electrodes, electrons are injected from the cathode side and holes are injected from the anode side, the electrons are recombined with the holes in the light-emitting layer to form an excited state, and energy is released as light when the excited state returns to the ground state.
For OLED display and illumination, the blue light material has been a bottleneck for the development of OLED, on one hand, blue light is an indispensable component in display and illumination technology, on the other hand, the efficiency of the traditional fluorescent material is not high, and the blue phosphorescent material has high efficiency but poor stability and is also lack of a deep blue light material system. The fluorescent blue-light material has good stability and a large number, and a series of blue-light dyes taking pyrene as a parent structure are protected by virtue of photosynthesis, such as the blue-light material shown in the following formula (a), and the CIE coordinates of a device serving as the blue-light material are (0.14,0.25), so that the blue-light material is a sky blue-light dye with good performance. However, the deep blue light material plays an important role in reducing the energy consumption of display and illumination devices and enhancing the overall effect of the devices, and the efficient deep blue light material is relatively less. Therefore, the development of such materials is of great significance.
As an example of a blue fluorescent material used in a light-emitting layer, patent document CN201080003398.4, US2014326985(a1) discloses a blue light-emitting material having a dibenzofuran substituent group, which can obtain blue light emission of a short wavelength, but has low emission efficiency, and further improvement is still required.
Although improvement in light-emitting characteristics can be confirmed with any material and any combination, it is not sufficient, and development of a light-emitting material exhibiting high light-emitting efficiency and realizing light emission at a shorter wavelength is urgently required.
Disclosure of Invention
The invention aims to provide a deep blue light emitting material with high color purity and high luminous efficiency, and an OLED device with long service life, high luminous efficiency and high color purity using the material.
According to the present invention, the following novel aromatic amine derivatives, organic electroluminescent devices, are provided.
The compound with the general formula of the invention is designed by adopting a compound taking 4-substituted 9, 9-dimethylfluorene as a structural unit, and has the outstanding advantages that: because the 4-position substitution of the dimethyl fluorene has great steric hindrance, the aromatic amine obtained by the dimethyl fluorene and proper fused ring aromatic hydrocarbon can obtain blue light emitted by short wavelength on one hand, and can remarkably improve the fluorescence luminous efficiency of the material on the other hand.
The general structural formula of the aromatic amine derivative provided by the invention is shown as the following formula (I).
Wherein Ar is selected from C6～C50Substituted or unsubstituted aryl, C6～C50Substituted or unsubstituted fused ring aromatic hydrocarbon group of (A), C4～C50Substituted or unsubstituted heteroaryl, C4～C50Substituted or unsubstituted fused heterocyclic aromatic hydrocarbon group.
Specifically, in the general formula (I), Ar is selected from C6～C50The substituted or unsubstituted aryl group of (a) means an aromatic ring system having 6 to 50 ring skeleton carbon atoms, including monocyclic structural substituentsGroups such as phenyl and the like, and also aromatic ring substituent groups such as biphenyl, terphenyl and the like which are covalently linked in structure.
Specifically, in the general formula (I), Ar is selected from C6～C50The substituted or unsubstituted fused ring aromatic hydrocarbon of (a) means an aromatic ring system having 10 to 50 ring skeleton carbon atoms, and includes fused ring structure substituent groups such as naphthyl, anthryl and the like, and also includes structural groups in which the fused ring structure substituent groups are linked to monocyclic structure aryl groups such as phenylbinaphthyl, naphthalene biphenyl, biphenyl-bianthryl and the like, and also includes fused aromatic ring substituent groups of a covalent linking structure such as binaphthyl and the like.
Specifically, in the above general formula (I), the heteroaryl group and the fused heterocyclic aromatic hydrocarbon group selected from Ar mean a monocyclic or fused ring aromatic group containing one or more heteroatoms selected from B, N, O, S, P (═ O), Si and P and having 4 to 50 ring carbon atoms.
Specifically, when Ar is selected from substituted aryl, substituted fused ring aromatic hydrocarbon group, substituted heteroaryl or substituted fused heterocyclic aromatic hydrocarbon group, the substituent is selected from C1～C12Linear, branched or cyclic alkyl groups of (a).
In the general formula of the invention, n is selected from 1 or 2:
when n ═ 2, L in the general formula (I) is selected from the structures represented by the following formulae A, B, C or D:
when n ═ 1, L in formula (I) is selected from the structures represented by the following formulae E or F:
further, in the general formula (I), Ar is preferably selected from C6～C24Substituted or unsubstituted aryl, C6～C24Substituted or unsubstituted condensed ring aromatic hydrocarbon group, C4～C30Substituted or unsubstituted heteroaryl of、C4～C30Substituted or unsubstituted fused ring heteroaromatic hydrocarbon group.
Further, when Ar is selected from a heteroaryl or fused ring heteroaryl hydrocarbon group, the heteroatom is preferably O, S or N.
In the general formula (I), Ar is more preferably selected from C6～C24Substituted or unsubstituted aryl, C6～C24Substituted or unsubstituted condensed aromatic hydrocarbon group
Further, in the general formula (I), Ar is preferably a phenyl group, a methylphenyl group, a phenanthryl group, a biphenyl group, a dibenzothienyl group, a naphthyl group, a phenanthryl group, a quinolyl group, a pyridyl group, and is preferably an anthracyl group, a terphenyl group, a fluorenyl group, a furyl group, a thienyl group, a pyrrolyl group, a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an indolyl group, a dibenzothienyl group, a 9-phenylcarbazole, a 9-naphthylcarbazole, a benzocarbazole, a dibenzocarbazole, an indolocarbazole, a benzodioxolyl group, or the like.
Still further, in the general formula (I) of the present invention, compounds represented by compounds having the following specific structures can be preferably selected: A1-A15, B1-B4, C1-C4, D1-D2, E1-E4, F1-F10, these compounds are merely representative.
The invention also provides the application of the compound selected from the general formula (I) in preparing an organic electroluminescent device.
The invention also provides an organic electroluminescent device, which comprises an anode, a cathode and one or more organic functional layers containing at least a luminescent layer between the two electrodes, wherein at least one layer of the organic functional layers contains the compound shown in the general formula (I) of the invention singly or as a mixed component.
In particular, the compound in the general formula (I) can be used as a host material of a light emitting layer in an organic electroluminescent device and a fluorescent light emitting material, but is not limited thereto.
The compound has a special 4-substituted 9, 9-dimethyl fluorene structural unit, and the arylamine compound formed by the unit and some optimized condensed ring aromatic hydrocarbons has the advantages of emitting deep blue light and high fluorescence quantum efficiency, can be applied to blue light OLED devices, can ensure that the CIE coordinate y value of the devices is less than 0.15, and can effectively reduce power consumption in display and illumination applications.
Drawings
FIG. 1: an emission spectrum of the blue light emitting material represented by the formula (a).
Detailed Description
In order to make those skilled in the art better understand the present invention, the organic electroluminescent compounds of the present invention and the preparation method thereof, and the preparation method and light emitting properties of a light emitting device comprising the same are described in detail below with reference to the following examples, and the present invention is further explained in detail.
Compounds of synthetic methods not mentioned in the examples are all commercially available starting products
Examples of Synthesis of the Main Compounds
Synthesis example 1.
Synthesis of A1
Under argon flow, 1, 6-dibromopyrene (3.6g,0.01mol), N- [4- (9, 9-dimethylfluorene) ] -aniline (5.5g,0.02mol), tris (dibenzylideneacetone) dipalladium (0) [ Pd2(dba)3 ] 0.08g, tri-tert-butylphosphine 50% toluene solution 0.5mL, sodium tert-butoxide (2.9g,0.03mol), and 100mL of dehydrated toluene were put into a 250mL eggplant-type flask, and the mixture was refluxed for 3 hours. After cooling, the reaction solution was filtered through celite, and the resulting crude product was recrystallized from toluene to give 5.6g of an off-white solid with a yield of 73%.
Synthesis example 2
Synthesis of A2
Compound A2 was prepared in the same manner as in example 1, except that N- [4- (9, 9-dimethylfluorene) ] -aniline was replaced with an equivalent amount of N- [4- (9, 9-dimethylfluorene) ] -2-methylaniline, and after the completion of the reaction, 7.6g of a white solid was isolated in a yield of 75%.
1H NMR(500MHz,Chloroform)δ7.92(t,J＝12.5Hz,6H),7.70(s,2H),7.59–7.47(m,6H),7.36(d,J＝21.9Hz,4H),7.28–7.09(m,10H),6.90(s,2H),2.13(s,6H),1.69(s,12H).
Synthesis example 3
Synthesis of A3
Compound A3 was prepared in the same manner as in example 1, except that N- [4- (9, 9-dimethylfluorene) ] -aniline was replaced with an equivalent amount of N- [4- (9, 9-dimethylfluorene) ] -3-methylaniline, and after the completion of the reaction, 7.6g of a white solid was isolated in a yield of 75%.
Synthesis example 4
Synthesis of A4
Compound A4 was prepared in the same manner as in example 1, except that N- [4- (9, 9-dimethylfluorene) ] -aniline was replaced with an equivalent amount of N- [4- (9, 9-dimethylfluorene) ] -4-methylaniline, and after the completion of the reaction, 7.6g of a white solid was isolated in a yield of 75%.
Synthesis example 5
Synthesis of A5
Compound A5 was prepared in the same manner as in example 1, except that N- [4- (9, 9-dimethylfluorene) ] -aniline was replaced with an equivalent amount of N- [4- (9, 9-dimethylfluorene) ] -4-cyclohexylaniline, and after the completion of the reaction, 6.3g of a white solid was isolated in a yield of 68%.
Synthesis example 6
Synthesis of A6
Compound A6 was prepared in the same manner as in example 1, except that N- [4- (9, 9-dimethylfluorene) ] -aniline was replaced with an equivalent amount of N- [4- (9, 9-dimethylfluorene) ] -4-tert-butylaniline, and after the completion of the reaction, 5.5g of a white solid was isolated in a yield of 63%.
Synthesis example 7
Synthesis of A7
Compound A7 was prepared in the same manner as in example 1, except that N- [4- (9, 9-dimethylfluorene) ] -aniline was replaced with an equivalent amount of N- [4- (9, 9-dimethylfluorene) ] -2-benzidine, and after completion of the reaction, 6.0g of a white solid was isolated in a yield of 65%.
1H NMR(500MHz,Chloroform)δ8.13–8.05(m,2H),7.98–7.85(m,6H),7.69(d,J＝15.0Hz,2H),7.48–7.03(m,28H),6.95(d,J＝15.0Hz,2H),1.69(s,12H).
Synthesis example 8
Synthesis of A8
Compound A8 was prepared in the same manner as in example 1, except that N- [4- (9, 9-dimethylfluorene) ] -aniline was replaced with an equivalent amount of N- [4- (9, 9-dimethylfluorene) ] -3-benzidine, and after completion of the reaction, 5.98g of a white solid was isolated in a yield of 65%.
Synthesis example 9
Synthesis of A9
Compound A9 was prepared in the same manner as in example 1, except that N- [4- (9, 9-dimethylfluorene) ] -aniline was replaced with an equivalent amount of N- [4- (9, 9-dimethylfluorene) ] -1-naphthylamine, and after the completion of the reaction, 7.2g of a white solid was isolated in a yield of 83%.
1H NMR(500MHz,Chloroform)δ8.19(dd,J＝14.4,3.7Hz,2H),7.96–7.77 (m,8H),7.71–7.12(m,24H),7.00(d,J＝15.0Hz,2H),1.68(s,12H).
Synthesis example 10
Synthesis of A10
Compound A10 was prepared in the same manner as in example 1, except that N- [4- (9, 9-dimethylfluorene) ] -aniline was replaced with an equivalent amount of N- [4- (9, 9-dimethylfluorene) ] -2-naphthylamine, and after the completion of the reaction, 7.2g of a white solid was isolated in a yield of 83%.
Synthesis example 11
Synthesis of A11
Compound A11 was prepared in the same manner as in example 1, except that N- [4- (9, 9-dimethylfluorene) ] -aniline was replaced with an equivalent amount of N- [4- (9, 9-dimethylfluorene) ] -1-phenanthrylamine, and after completion of the reaction, 6.4g of a white solid was isolated in a yield of 66%.
Synthesis example 12
Synthesis of A12
Compound A12 was prepared in the same manner as in example 1, except that N- [4- (9, 9-dimethylfluorene) ] -aniline was replaced with an equivalent amount of N- [4- (9, 9-dimethylfluorene) ] -3-phenanthrylamine, and after the reaction was completed, 6.4g of a white solid was isolated in a yield of 66%.
Synthesis example 13
Synthesis of A13
Compound A13 was prepared in the same manner as in example 1, except that N- [4- (9, 9-dimethylfluorene) ] -aniline was replaced with an equivalent amount of N- [4- (9, 9-dimethylfluorene) ] -2-phenylpyridin-4-amine, and after the reaction was completed, 5.7g of a white solid was isolated in 62% yield.
1H NMR(500MHz,Chloroform)δ8.41–8.24(m,6H),8.01–7.86(m,6H),7.81(d,J＝14.9Hz,2H),7.74–7.42(m,16H),7.41–7.10(m,6H),6.29(dd,J＝15.0,2.9Hz,2H),1.69(s,12H).
Synthesis example 14
Synthesis of A14
Compound A14 was prepared in the same manner as in example 1, except that N- [4- (9, 9-dimethylfluorene) ] -aniline was replaced with an equivalent amount of N- [4- (9, 9-dimethylfluorene) ] -quinolin-2-amine, and after completion of the reaction, 5.7g of a white solid was isolated in a yield of 65%.
Synthesis example 15
Synthesis of A15
Compound A15 was prepared in the same manner as in example 1, except that N- [4- (9, 9-dimethylfluorene) ] -aniline was replaced with an equivalent amount of N- [4- (9, 9-dimethylfluorene) ] yl-fluoren-2-amine, and after the completion of the reaction, 6.8g of a white solid was isolated in a yield of 68%.
Synthesis example 16
Synthesis of B1
6, 12-dibromo-compound was put into a 250mL round bottom flask under argon flow
(3.9g,0.01mol), N- [4- (9, 9-dimethylfluorene)]-2, 4-dimethylaniline (3.1g,0.02mol), tris (dibenzylideneacetone) dipalladium (0) [ Pd2(dba)3 ] 0.08g, tri-tert-butylphosphine 50% toluene solution 0.2mL, sodium tert-butoxide (2.9g,0.03mol), 100mL of dehydrated toluene, and refluxing for 3 hours. After cooling, the reaction solution was filtered through celite, and the resulting crude product was recrystallized from toluene to give 6.3g of an off-white solid with a yield of 74%.
1H NMR(500MHz,Chloroform)δ8.98(dd,J＝14.2,3.7Hz,2H),8.50(s,2H),8.11(dd,J＝14.3,3.7Hz,2H),7.90(dd,J＝14.7,3.2Hz,2H),7.74–7.50(m,8H),7.42–7.14(m,8H),7.13–6.98(m,4H),6.86(d,J＝2.5Hz,2H),2.24(s,6H),2.13(s,6H),1.69(s,12H).
Synthesis example 17
Synthesis of B2
Compound B2 was prepared in the same manner as in example 17, except that N- [4- (9, 9-dimethylfluorene) ] -2, 4-dimethylaniline was replaced with an equivalent of N- [4- (9, 9-dimethylfluorene) ] -2-methylaniline, and after the completion of the reaction, 5.8g of a white solid was isolated in a yield of 71%.
Synthesis example 18
Synthesis of B3
Compound B3 was prepared in the same manner as in example 17 except that N- [4- (9, 9-dimethylfluorene) ] -2, 4-dimethylaniline was replaced with an equivalent of N- [4- (9, 9-dimethylfluorene) ] -2-benzidine, and after the completion of the reaction, 6.9g of a white solid was isolated in a yield of 73%.
Synthesis example 19
Synthesis of B4
Compound B4 was prepared in the same manner as in example 17, except that N- [4- (9, 9-dimethylfluorene) ] -2, 4-dimethylaniline was replaced with an equivalent of N- [4- (9, 9-dimethylfluorene) ] -1-naphthylamine, and after the completion of the reaction, 6.1g of a white solid was isolated in a yield of 68%.
Synthesis example 20
Synthesis of C1
2, 8-dibromo-6, 6,12, 12-tetramethyl-6, 12-dihydroindeno [1,2-B ] fluorene (4.7g, 0.01mol) was reacted with N- [4- (9, 9-dimethylfluorene) ] -2, 4-dimethylaniline (6.3, 0.02mol), tris (dibenzylideneacetone) dipalladium (0) [ Pd2(dba)3 ] 0.08g, tri-tert-butylphosphine 50% toluene solution 0.2mL, sodium tert-butoxide (2.9g,0.03mol), dehydrated toluene 100mL, and refluxed for 3 hours. After cooling, the reaction solution was filtered through celite, and the obtained crude product was recrystallized from toluene to obtain 6.9g of a pale yellow solid with a yield of 74%.
Synthesis example 21
Synthesis of C2
Compound C2 was prepared in the same manner as in Synthesis example 21, except that N- [4- (9, 9-dimethylfluorene) ] -2, 4-dimethylaniline was replaced with an equivalent of N- [4- (9, 9-dimethylfluorene) ] -aniline, and after the reaction was completed, 6.2g of a pale yellow solid was isolated in a yield of 71%.
1H NMR(500MHz,Chloroform)δ8.07–7.85(m,6H),7.65–7.49(m,6H),7.43–7.15(m,14H),7.11–6.93(m,6H),1.69(s,24H).
Synthesis example 22
Synthesis of C3
Compound C3 was prepared in the same manner as in Synthesis example 21, except that N- [4- (9, 9-dimethylfluorene) ] -2, 4-dimethylaniline was replaced with N- [4- (9, 9-dimethylfluorene) ] -3-benzidine in an equivalent amount, and after the reaction was completed, 6.9g of a pale yellow solid was isolated in a yield of 67%.
Synthesis example 23
Synthesis of C4
Compound C4 was prepared in the same manner as in Synthesis example 21, except that N- [4- (9, 9-dimethylfluorene) ] -2, 4-dimethylaniline was replaced with N- [4- (9, 9-dimethylfluorene) ] -1-naphthylamine in an equivalent amount, and after the reaction was completed, 6.7g of a pale yellow solid was isolated in a yield of 68%.
Synthesis example 24
Synthesis of D1
5, 11-dibromo 7,7,13, 13-tetramethyl 7, 13-dihydrobenzo [ g ]]Indeno [1,2-B]Fluorene (10mmol, 5.18g) and N- [4- (9, 9-dimethylfluorene)]-3-benzidine (22mmol, 7.9g), sodium tert-butoxide 5.7g, toluene 200mL, nitrogen gas below the solution surface for 30min, and then 0.4g Pd2(dba)310ml of 10% tri-tert-butylphosphine was injected into the flask by a syringe, the mixture was stirred, heated to 120 ℃ and reacted for 4 hours, and then the reaction mixture was washed with water, the organic phase was concentrated and recrystallized from toluene to give 6.9g of a pale yellow solid with a yield of 64%.
Synthesis example 25
Synthesis of D2
Compound D2 was prepared in the same manner as in Synthesis example 25, except that N- [4- (9, 9-dimethylfluorene) ] -3-benzidine was replaced with an equivalent of N- [4- (9, 9-dimethylfluorene) ] -aniline, and after the completion of the reaction, 6.7g of a pale yellow solid was isolated in a yield of 72%.
Synthesis example 26
Synthesis of E1
1-bromopyrene (10mmol, 2.8g) and N- [4- (9, 9-dimethylfluorene)]Aniline (22mmol, 5.7g), sodium tert-butoxide 5.7g, toluene 100mL, nitrogen gas was introduced below the solution surface30min, then adding 0.2g Pd2(dba)3Injecting 2ml of 10 percent tri-tert-butylphosphine by using a syringe, starting stirring, heating to 120 ℃, washing reaction liquid after 4 hours of reaction, concentrating an organic phase, and recrystallizing toluene to obtain 3.6g of light yellow solid with the yield of 75 percent.
1H NMR(500MHz,Chloroform)δ8.31(s,1H),8.12–8.00(m,5H),7.98–7.87(m,3H),7.70(s,1H),7.66–7.55(m,3H),7.34(s,1H),7.23(t,J＝10.0Hz,4H),7.08(s,2H),7.00(s,1H),1.69(s,6H).
Synthesis example 27
Synthesis of E2
Compound E2 was prepared in the same manner as in Synthesis example 27, except that N- [4- (9, 9-dimethylfluorene) ] aniline was replaced with N- [4- (9, 9-dimethylfluorene) ] 2-naphthylamine in an equivalent amount, and after the reaction was completed, 3.9g of a pale yellow solid was isolated in a yield of 72%.
Synthesis example 28
Synthesis of E3
Compound E3 was prepared in the same manner as in Synthesis example 27, except that N- [4- (9, 9-dimethylfluorene) ] aniline was replaced with N- [4- (9, 9-dimethylfluorene) ] 2-dibenzothiophene in an equivalent amount, and after the reaction was completed, 3.8g of a pale yellow solid was isolated in a yield of 65%.
Synthesis example 29
Synthesis of E4
Compound E4 was prepared in the same manner as in Synthesis example 27, except that N- [4- (9, 9-dimethylfluorene) ] aniline was replaced with N- [4- (9, 9-dimethylfluorene) ] -9, 9-dimethylfluoren-2-amine of equivalent weight, and after the reaction was completed, 3.8g of a pale yellow solid was isolated in a yield of 63%.
Synthesis example 30
Synthesis of F1
5-bromo-7, 7,13, 13-tetramethyl-7, 13-dihydrobenzo [ g ]]Indeno [1,2-B]Fluorene (10mmol, 4.4g) (10mmol, 2.8g) and N- [4- (9, 9-dimethylfluorene)]2-methylaniline (22mmol, 6.6g), tert5.7g of sodium butoxide and 100mL of toluene, nitrogen is introduced below the solution surface for 30min, and then 0.2g of Pd is added2(dba)3Injecting 2ml of 10 percent tri-tert-butylphosphine by using a syringe, starting stirring, heating to 120 ℃, washing reaction liquid after 4 hours of reaction, concentrating an organic phase, and recrystallizing toluene to obtain 5.2g of light yellow solid with the yield of 79 percent.
1H NMR(500MHz,Chloroform)δ8.91–8.80(m,1H),8.58(s,1H),8.23(dt,J＝16.8,8.4Hz,1H),8.19–8.11(m,1H),8.09(s,1H),7.90(dd,J＝14.7,3.2Hz,1H),7.62–7.46(m,5H),7.41–7.07(m,10H),6.90(ddd,J＝15.1,9.1,3.4Hz,1H),2.13(s,3H),1.75(s,6H),1.69(s,12H).
Synthesis example 31
Synthesis of F2
Compound F2 was prepared in the same manner as in Synthesis example 27, except that N- [4- (9, 9-dimethylfluorene) ] -2-methylaniline was replaced with an equivalent of N- [4- (9, 9-dimethylfluorene) ] -2, 4-dimethylaniline, and after the completion of the reaction, 5.0g of a pale yellow solid was isolated in a yield of 75%.
Synthesis example 32
Synthesis of F3
Compound F3 was prepared in the same manner as in Synthesis example 27, except that N- [4- (9, 9-dimethylfluorene) ] -2-methylaniline was replaced with an equivalent of N- [4- (9, 9-dimethylfluorene) ] -4-cyclohexylaniline, and after the completion of the reaction, 5.9g of a pale yellow solid was isolated in a yield of 81%.
Synthesis example 33
Synthesis of F4
Compound F4 was prepared in the same manner as in Synthesis example 27, except that N- [4- (9, 9-dimethylfluorene) ] -2-methylaniline was replaced with an equivalent of N- [4- (9, 9-dimethylfluorene) ] -2-benzidine, and after the completion of the reaction, 5.7g of a pale yellow solid was isolated in a yield of 79%.
Synthesis example 34
Synthesis of F5
Compound F5 was prepared in the same manner as in Synthesis example 27, except that N- [4- (9, 9-dimethylfluorene) ] -2-methylaniline was replaced with an equivalent of N- [4- (9, 9-dimethylfluorene) ] -1-naphthylamine, and after the completion of the reaction, 5.1g of a pale yellow solid was isolated in a yield of 73%.
Synthesis example 35
Synthesis of F6
Compound F6 was prepared in the same manner as in Synthesis example 27, except that N- [4- (9, 9-dimethylfluorene) ] -2-methylaniline was replaced with an equivalent of N- [4- (9, 9-dimethylfluorene) ] -1-phenanthrylamine, and after the completion of the reaction, 4.6g of a pale yellow solid was isolated in 62% yield.
Synthesis example 36
Synthesis of F7
Compound F7 was prepared in the same manner as in Synthesis example 27, except that N- [4- (9, 9-dimethylfluorene) ] -2-methylaniline was replaced with an equivalent of N- [4- (9, 9-dimethylfluorene) ] -3-benzidine, and after the completion of the reaction, 5.3g of a pale yellow solid was isolated in a yield of 74%.
Synthesis example 37
Synthesis of F8
Compound F8 was prepared in the same manner as in Synthesis example 27, except that N- [4- (9, 9-dimethylfluorene) ] -2-methylaniline was replaced with an equivalent of N- [4- (9, 9-dimethylfluorene) ] -4-phenylpyridin-2-amine, and after the reaction was completed, 5.1g of a pale yellow solid was isolated in a yield of 71%.
Synthesis example 38
Synthesis of F9
Compound F9 was prepared in the same manner as in Synthesis example 27, except that N- [4- (9, 9-dimethylfluorene) ] -2-methylaniline was replaced with an equivalent amount of N- [4- (9, 9-dimethylfluorene) ] -quinolin-2-amine, and after the completion of the reaction, 4.4g of a pale yellow solid was isolated in a yield of 64%.
Synthesis example 39
Synthesis of F10
Compound F10 was prepared in the same manner as in Synthesis example 27, except that N- [4- (9, 9-dimethylfluorene) ] -2-methylaniline was replaced with an equivalent of N- [4- (9, 9-dimethylfluorene) ] -9, 9-dimethylfluoren-2-amine, and after the completion of the reaction, 5.2g of a pale yellow solid was isolated in a yield of 68%.
1H NMR(500MHz,Chloroform)δ8.91–8.78(m,1H),8.63(s,1H),8.24(dd,J＝14.9,3.1Hz,1H),8.20–8.10(m,1H),8.08(s,1H),7.95–7.80(m,3H),7.72(s,1H),7.68–7.41(m,7H),7.39–7.12(m,9H),1.75(s,6H),1.69(s,18H).
The characterization was performed by mass spectrometry and elemental analysis of compounds a1 to a15, B1 to B4, C1 to C4, D1 to D2, E1 to E4, F1 to F10, and the data are shown in table 1 below.
Table 1: characterization data for the Compounds of the synthetic examples
Device examples of the Compounds of the invention
The technical effects of the compounds of the present invention are explained in more detail below by means of device examples.
Device example 1
Carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent (the volume ratio is 1: 1), baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate 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 × 10-5～9×10-3Pa, performing vacuum evaporation on the anode layer film to form 2-TNATA serving as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
NPB is evaporated on the hole injection layer in vacuum to serve as a hole transport layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 80 nm;
a luminescent layer of the device is evaporated in vacuum on the hole transport layer, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material ADN is adjusted to be 0.1nm/s, the evaporation rate of the dye DSA-Ph is set in a proportion of 3%, and the total evaporation film thickness is 30nm by using a multi-source co-evaporation method;
vacuum evaporating an electron transport layer material Bphen of the device on the luminescent layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30 nm;
LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a cathode of the device.
The structure of the organic electroluminescent device in embodiment 1 of the device of the present invention is:
ITO/2-TNATA(10nm)/NPB(80nm)/ADN﹕DSA-Ph(30nm)/Bphen(30nm)/LiF(1nm)/Al。
the molecular structure of each functional layer material is as follows:
device example 2
The method is the same as device example 1, except that DSA-Ph is replaced with an equal amount of a1
Device example 3
The method is the same as device example 1, except that DSA-Ph is replaced with an equal amount of a5
Device example 4
The method is the same as the device embodiment, except that the DSA-Ph is replaced with an equal amount of A10
Device example 5
The method is the same as the device embodiment, except that the DSA-Ph is replaced with an equal amount of B2
Device example 6
The method is the same as the device embodiment, except that the DSA-Ph is replaced with an equal amount of C1
Device example 7
The method is the same as the device embodiment, except that the DSA-Ph is replaced with an equal amount of D2
Device example 8
The method is the same as the device embodiment, except that the DSA-Ph is replaced with an equal amount of E1
Device example 9
The method is the same as the device embodiment, except that the DSA-Ph is replaced with an equal amount of F1
Device example 10
The method is the same as the device embodiment, except that the DSA-Ph is replaced with an equal amount of F5
Device example 11
The method is the same as the device embodiment, except that the DSA-Ph is replaced with an equal amount of F9
At the same luminance 1000cd/m2Next, the driving voltage and current efficiency and the CIE coordinate value of the organic electroluminescent device prepared in device example 1 were measured, and the corresponding performance indexes are detailed in table 2 below.
Table 2:
as can be seen from the table above, compared with the blue dye DSA-Ph, the compound can realize deep blue light, the color coordinate y value is between 0.1 and 0.18, and the requirements of various blue light periods can be met; comparative device example 1 and device example 2, in agreement with the above-mentioned spectral data, using the sky blue dye DSA-Ph of the comparative compound as a light-emitting material and having color coordinates of (0.14, 0.35), while the blue device using the compound a1 of the present invention achieved color coordinates of (0.13, 0.14), which is a deeper blue material having better performance. The results show that the novel organic material is used for the organic electroluminescent device, can effectively reduce the take-off and landing voltage and improve the current efficiency, and is a blue dye material with good performance.
While the preferred embodiments of the present invention have been described in detail, the present invention is not limited to the details of the above embodiments, and various simple modifications may be made to the technical solution of the present invention within the technical idea of the present invention, which fall within the scope of the present invention, and the present invention is not separately described for various possible simple modifications in order to avoid unnecessary repetition. In addition, any combination of the various embodiments of the present invention is also possible, and the same should be considered as the disclosure of the present invention as long as it does not depart from the spirit of the present invention.
Claims (6)
1. A compound of the general formula (I):
wherein:
ar is selected from the following substituted or unsubstituted groups: phenyl, methylphenyl, phenanthryl, biphenyl, naphthyl, quinolyl, pyridyl, anthracyl, terphenyl, fluorenyl, dibenzothienyl, wherein the substituents are selected from C1～C12A linear alkyl group or a cyclohexyl group of (1);
n is 1 or 2;
when n is 2, L is selected from the structures represented by the following formulas C or D:
when n ═ 1, L is selected from the structures represented by formula F below:
2. a compound having the following specific structural formula:
3. use of a compound of formula (la) according to claim 1 in an organic electroluminescent device.
4. Use of the structural compound according to claim 2 in an organic electroluminescent device.
5. An organic electroluminescent device comprising an anode, a cathode and one or more organic functional layers containing at least a light-emitting layer between the two electrodes, wherein at least one of the organic functional layers contains the compound according to any one of claims 1 or 2 alone or as a mixed component.
6. The organic electroluminescent device according to claim 5, wherein the at least one organic functional layer is a light emitting layer.
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| CN103304428A (en) * | 2012-03-06 | 2013-09-18 | 三星显示有限公司 | Amine-based compound, organic light-emitting diode including the same, and organic light-emitting apparatus including the amine-based compound |
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| CN104628510A (en) * | 2015-02-04 | 2015-05-20 | 北京鼎材科技有限公司 | 2,6,6,8-tetra-substituted-6H-benzo[cd]pyrene compound and organic electroluminescence device containing same |
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