CN1560052A - Derivant of electrophosphorescence 1,8-naphthimide and luminous ligand thereof - Google Patents

Derivant of electrophosphorescence 1,8-naphthimide and luminous ligand thereof Download PDF

Info

Publication number
CN1560052A
CN1560052A CNA2004100165674A CN200410016567A CN1560052A CN 1560052 A CN1560052 A CN 1560052A CN A2004100165674 A CNA2004100165674 A CN A2004100165674A CN 200410016567 A CN200410016567 A CN 200410016567A CN 1560052 A CN1560052 A CN 1560052A
Authority
CN
China
Prior art keywords
naphthalimide
acid anhydride
compound
preparation
phenyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CNA2004100165674A
Other languages
Chinese (zh)
Other versions
CN1259317C (en
Inventor
禾 田
田禾
丁国华
荆淑萍
朱为宏
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
East China University of Science and Technology
Original Assignee
East China University of Science and Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by East China University of Science and Technology filed Critical East China University of Science and Technology
Priority to CN 200410016567 priority Critical patent/CN1259317C/en
Publication of CN1560052A publication Critical patent/CN1560052A/en
Application granted granted Critical
Publication of CN1259317C publication Critical patent/CN1259317C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Landscapes

  • Electroluminescent Light Sources (AREA)
  • Luminescent Compositions (AREA)

Abstract

The invention designs and synthesizes an electrophosphorescent or electrofluorescent 1,8-naphthalimide derivative. The derivative contains a five-membered heterocyclic functional grou: 1, 8-naphthalimide, benzothiazole, etc, which ensures both the injection and compound of carriers and the generation of excitons happen in molecules and simultaneously avoids the defect of light chroma change caused by the change of conjugated delocalization degree; its maximum lighting wavelength is in 511-521 nm (emitting yellow-green light) or greater than 630 nm (emitting red light), and at driving voltage, the maximum light brightness is 4500-4800 cd/sq m.

Description

Electroluminescent phosphorescence 1,8-naphthalimide derivative and luminous part thereof
Technical field
The present invention relates to a kind of electroluminescent organic compound, specifically, relate to 1 of a kind of electroluminescent phosphorescence or fluorescence, the 8-naphthalimide derivative.
Background technology
Compare with liquid-crystal display, organic electroluminescence device (OLED) is the state-of-the-art technique of display of generally acknowledging.It has overcome the shortcoming of liquid-crystal display fully, low voltage direct drive, active illuminating, visual angle are big, flexible, the fast big area of response speed shows, luminous color is complete and low cost and other advantages but have, thereby nearly all in the world associated major company all drops into a large amount of man power and materials, joins in this competition that becomes a flash point day by day.
Naphthalimide derivative is the very important functional materials of a class.Remove at present and be widely used as fluorescence dye and white dyes, also can be used for high-technology fields such as metal fluorescent inspection, solar collector, liquid crystal, laser, organic light-guide material.Discovering in recent years, naphthalimide derivative are the good electron-transporting type electroluminescent materials of a class luminous efficiency, and purification easily, vacuum evaporation easily have good advantages such as light stability.Common jaundice green glow, emission wavelength can be tuning by changing molecular structure.In addition, the molecular structure of this compounds also has such several characteristics: coplanarity; Has bigger conjugated system; An end has strong electron-donating group in the molecular structure, and the other end has strong electron-withdrawing group, so exists big " inhaling-power sub-conjugated system " in its molecular structure.Therefore, to the research of naphthalimide derivative deepen continuously carry out among.
At present, contain 1, the luminescent material of 8-naphthalimide someone in succession reports, relevant patent has also the time open.For example application number is 00116212.8 Chinese patent, discloses a class and has contained 1, and the molecular distortion type electroluminescent material of 8-naphthalimide has been obtained effect preferably in actual applications, but the leeway of further raising is still arranged.
Summary of the invention
Design of the present invention is such:
The contriver is on the basis of big quantity research, and based on 1, the 8-naphthalimide is a kind of luminescent material of high performance electronic mode transmission, and with five circle heterogeneous ring compounds and 1 such as benzothiazoles, the 8-naphthalimide connects by the covalent linkage key.Since exist 1 between the functional group, the repulsion drag effect of the carbonyl of 8-naphthalimide, five circle heterocycle functional groups and 1 such as benzothiazole, 8-naphthalimide functional group is not on the plane, and molecular distortion has taken place.This luminescent material can guarantee that the injection of current carrier, the generation that is compound to exciton all occur in intramolecularly, simplify the manufacture craft of device.Can avoid simultaneously conjugated polymer luminescent material often owing to the variation of conjugation delocalization degree causes the defective that luminescent chromaticity changes.
Technical scheme:
1 of said electroluminescent phosphorescence of the present invention or fluorescence, the 8-naphthalimide derivative, its structure is shown below:
Or
In the formula: X is S, O or N; M is metal iridium (Ir) or europium (Eu);
R is a kind of in the following groups:
Wherein: R 1, R 2Be a kind of in methyl, the ethyl.
Above-claimed cpd is synthetic like this:
At first with 4-bromo-1,8-naphthalene acid anhydride is a starting raw material, and itself and piperidines, morpholine or the reaction of replacement amine are made 1 of 4 replacements, 8-naphthalene acid anhydride; With 1 of 4 replacements, 8-naphthalene acid anhydride and 4-(2-benzo five circle heterocyclic radicals) aniline reaction promptly gets target compound (1), will get target compound (2) behind compound (1) and the metal complex then.Wherein: the synthetic method of 4-(2-benzo five circle heterocyclic radicals) aniline is referring to document J.Am.Chem.Soc.1957,427-429 and J.Heterocylic Chem.1998,35:1301-1304.
The route map of said synthetic method is as follows:
In the formula: X is S, O or N; M is metal iridium (Ir) or europium (Eu);
R is a kind of in the following groups:
Wherein: R 1, R 2Be a kind of in methyl, the ethyl.
Said compound of the present invention (1) and compound (2) all can adopt prior art to make electroluminescent device, wherein make its maximum emission wavelength of electroluminescent device between 511-521nm by compound (1), the jaundice green glow, maximum luminance is 4500-4800cd/m under driving voltage 20V 2And make its maximum emission wavelength of electroluminescent device greater than 630nm by compound (2), and glowing, maximum luminance is 4800cd/m under driving voltage 20V 2The present invention designs synthetic compound great advantage and is, it can guarantee that the injection of current carrier, the generation that is compound to exciton all occur in intramolecularly, avoids simultaneously causing the defective that luminescent chromaticity changes owing to the variation of conjugation delocalization degree.
Embodiment
The invention will be further described below by embodiment, its objective is to be better understanding content of the present invention.Therefore, the cited case does not influence protection scope of the present invention:
Embodiment 1
4-piperidyl-N-[4-(2-[4-morpholinodithio base) phenyl]-1, the 8-naphthalimide is synthetic:
(1) 4-piperidyl-1, the preparation of 8-naphthalene acid anhydride
In round-bottomed flask, add 2.76g 4-bromo-1,8-naphthalene acid anhydride, 1.5mL piperidines and 40mL ethylene glycol monomethyl ether stir reflux 3h.Standing over night is separated out precipitation.Suction filtration gets orange solids.With ethanol and ethylene glycol monomethyl ether recrystallization, get orange red needle-like crystal 2.04g, yield 73.6%.172～173 ℃ of fusing points.
(2) preparation of 4-(2-[4-morpholinodithio base) aniline
In round-bottomed flask, add 2.74g para-amino benzoic acid, 2.2mL near amino thiophenols and 30mL polyphosphoric acid (PPA).Argon shield is heated to 250 ℃ of reaction 4h.After the cooling, be diluted to water and separate out solid.Filter filter cake impouring 10%Na 2CO 3In the aqueous solution, leave standstill 30min after the stirring, suction filtration gets thick product.Drying, ethyl alcohol recrystallization gets pure product 1.98g, yield 43.8%.Fusing point＞270 ℃
(3) 4-piperidyl-N-[4-(2-[4-morpholinodithio base) phenyl]-1, the preparation of 8-naphthalimide
In there-necked flask, add 1.74g4-piperidyl-1,8-naphthalene acid anhydride, 0.75g4-(2-[4-morpholinodithio base) aniline, 1mL piperidines, 15mL ethylene glycol monomethyl ether.Reflux 12h under the argon shield.Finish reaction, standing over night.Separate out precipitation.Suction filtration gets crude product.With the dehydrated alcohol recrystallization, get the yellow-green colour solid.Productive rate 31.7%.Fusing point＞280 ℃.
1H-NMR(CDCl 3)：1.76(m，2H，-CH 2)，1.92(m，4H，-CH 2)，3.30(t，4H，-CH 2)，7.23(d，J＝8.06Hz，1H，-CH)，7.42(t，1H)，7.47(d×d，J＝2.59Hz，J＝2.23Hz，2H)，7.52(t，1H)，7.73(t，1H)，7.94(d，J＝7.94Hz，1H)，8.11(d，J＝8.05，1H)，8.28(d×d，J＝1.67Hz，J＝1.62Hz，2H)，8.47(d，J＝8.22Hz，1H)，8.56(d，J＝8.16Hz，1H)，8.64(d，J＝7.28Hz，1H)。
MS-EI?m/e：489(100％)[M +]，490(21.40％)[M ++1]，488(42.60％)[M +-1].
Standardized solution (1 * 10 at tetrahydrofuran (THF) -5M) in, the ultraviolet-visible maximum absorption band is respectively 302nm and 414nm, and its fluorescent emission maximum peak is at 521nm.
Embodiment 2
4-piperidyl-N-[4-(2-Bing oxazolyl) phenyl]-1,8-naphthalimide synthetic:
Figure A20041001656700061
(1) preparation of 4-(2-benzoxazolyl) aniline
Except that a kind of raw material near amino thiophenols is wherein replaced with the Ortho-Aminophenol, the preparation method is with (2) among the embodiment 1.Get pure product 3.99g, productive rate 63%.172～175 ℃ of fusing points.
(2) 4-piperidyl-N-[4-(2-Bing oxazolyl) phenyl]-1, the preparation of 8-naphthalimide
With 4-(2-benzoxazolyl) aniline and 4-piperidyl-1,8-naphthalene acid anhydride (preparation is referring to embodiment 1 step (1)) makes target product (yellow-green colour solid) by the method for (3) among the embodiment 1.Productive rate 45.8%.Fusing point＞270 ℃.
1H-NMR(CDCl 3)：1.76(m，2H)，1.92(m，4H)，3.28(m，4H)，7.22(d，J＝8.08Hz，1H)，7.39(t，2H)，7.50(d，J＝8.43Hz，2H)，7.62(d×d，J＝3.36Hz，J＝2.29Hz，1H)，7.73(t，1H)，7.82(d×d，J＝2.33Hz，J＝3.3Hz，1H)，8.44(d，J＝8.43Hz，2H)，8.46(t，1H)，8.56(d，J＝8.06Hz，1H)，8.64(d×d，J＝0.79Hz，J＝0.81Hz，1H)。MS-EI?m/e：473(100％)[M +]，474(21.34％)[M ++1]，472(47.84％)[M +-1].
Standardized solution (1 * 10 at tetrahydrofuran (THF) -5M) in, the ultraviolet-visible maximum absorption band is respectively 303nm and 411nm, and its fluorescent emission maximum peak is at 518nm.
Embodiment 3
4-piperidyl-N-[4-(2-benzimidazolyl-) phenyl]-1,8-naphthalimide synthetic:
(1) preparation of 4-(2-benzimidazolyl-) aniline
Except that a kind of raw material near amino thiophenols is wherein replaced with the O-Phenylene Diamine, the preparation method is with (2) among the embodiment 1.Get the pure product 1.80g of 4-(2-benzimidazolyl-) aniline, productive rate 28.7%.174～175 ℃ of fusing points.
(2) 4-piperidyl-N-[4-(2-benzimidazolyl-) phenyl]-1, the preparation of 8-naphthalimide
With 4-(2-benzimidazolyl-) aniline and 4-piperidyl-1,8-naphthalene acid anhydride (preparation is referring to embodiment 1 step (1)) makes target product (yellow-green colour solid) by the method for (3) among the embodiment 1.Productive rate 55.1%.Fusing point＞270 ℃.
1H-NMR(CDCl 3)：1.76(m，2H)，1.92(d，J＝4.59Hz，4H)，3.30(m，4H)，7.25(t，1H)，7.27(d，2H)，7.44(d，J＝8.21Hz，2H)，7.47(t，1H)，7.74(t，1H)，7.84(d，J＝6.31Hz，1H)，8.13(d，J＝8.2Hz，2H)，8.48(d，J＝8.4Hz，1H)，8.58(d，J＝8.07Hz，1H)，8.66(d，J＝7.17Hz，1H)。MS-EI?m/e：472(100％)[M +]，473(20.61％)[M ++1]，471(42.88％)[M +-1].
Standardized solution (1 * 10 at tetrahydrofuran (THF) -5M) in, the ultraviolet-visible maximum absorption band is respectively 307nm and 414nm, and its fluorescent emission maximum peak is at 521nm.
Embodiment 4
4-morpholinyl-N-[4-(2-benzimidazolyl-) phenyl]-1,8-naphthalimide synthetic:
(1) 4-morpholinyl-1, the preparation of 8-naphthalene acid anhydride
Except that a kind of raw material piperidines is wherein replaced with the morpholine, the preparation method is with (1) among the embodiment 1.Get the 4-morpholinyl-1 of orange red needle-like crystal, 8-naphthalene acid anhydride 3.81g.Productive rate 85.3%.173～175 ℃ of fusing points.
(2) 4-morpholinyl-N-[4-(2-benzimidazolyl-) phenyl]-1, the preparation of 8-naphthalimide
With 4-(2-benzimidazolyl-) aniline (preparation method is referring to the step (1) of example 3) and 4-morpholinyl-1,8-naphthalene acid anhydride makes target product (glassy yellow solid) by the method for (3) among the embodiment 1.Productive rate 18.4%.Fusing point＞300 ℃.
1H-NMR(CDCl 3)：3.32(t，4H)，4.05(t，4H)，7.28(d，J＝8.4Hz，1H)，7.30(t，2H)，7.43(d，J＝8.30Hz，2H)，7.67(d，2H)，7.77(t，1H)，8.19(d，J＝8.32Hz，2H)，8.50(d，J＝8.45Hz，1H)，8.59(d，J＝8.45Hz，1H)，8.65(d，J＝7.15Hz，1H).
MS-EI?m/e：474(100％)[M +]，475(31.44％)[M ++1]，416(61.90％)，207(31.25％).
Standardized solution (1 * 10 at tetrahydrofuran (THF) -5M) in, the ultraviolet-visible maximum absorption band is respectively 309nm and 390nm, and its fluorescent emission maximum peak is at 511nm.
Embodiment 5
4-morpholinyl-N-[4-(2-[4-morpholinodithio base) phenyl]-1,8-naphthalimide synthetic:
With 4-morpholinyl-1,8-naphthalene acid anhydride and 4-(2-[4-morpholinodithio base) aniline makes target product (glassy yellow solid) by the synthetic method of (3) among the embodiment 1.Productive rate 33.3%.Fusing point＞300 ℃.
1H-NMR(CDCl 3)：3.32(t，4H)，4.05(t，4H)，7.29(d，J＝8.1Hz，1H)，7.42(t，1H)，7.47(d，J＝8.4Hz，2H)，7.53(t，1H)，7.77(t，1H)，7.94(d，J＝8.0Hz，1H)，8.10(d×d，J＝8.1Hz，J＝4.8Hz，1H)，8.26(d×d，J＝8.3Hz，J＝3.9Hz，2H)，8.51(d，J＝8.3Hz，1H)，8.61(d，J＝8.1Hz，1H)，8.67(d，J＝7.1Hz，1H).MS-EI?m/e：491(100％)[M +]，492(24.83％)[M ++1]，433(32.74％)，207(16.73％).Anal.Calcd?for?C 30H 24N 3O 3S：C，70.93％H，4.31％.N，8.55％.Found：C，69.95％H，4.20％N，8.33.
Standardized solution (1 * 10 at tetrahydrofuran (THF) -5M) in, the ultraviolet-visible maximum absorption band is respectively 302nm and 392nm, and its fluorescent emission maximum peak is at 513nm.
Embodiment 6
4-morpholinyl-N-[4-(2-benzoxazolyl) phenyl]-1,8-naphthalimide synthetic:
With 4-morpholinyl-1,8-naphthalene acid anhydride and 4-(2-benzoxazolyl) aniline makes target product (glassy yellow solid) by (3) synthetic method among the embodiment 1.Productive rate 35.4%.Fusing point＞300 ℃.
1H-NMR(CDCl 3)：3.32(t，4H)，4.05(t，4H)，7.29(d，J＝8.16Hz，1H)，7.39(t，3H)，7.51(d×d，J＝1.93Hz，J＝1.81Hz，2H)，7.77(t，1H)，7.82(d×d，J＝2.27Hz，J＝3.40Hz，1H)，8.42(d，2H)，8.51(d×d，J＝0.84Hz，J＝0.90Hz，1H)，8.60(d，J＝7.99Hz，1H)，8.66(d×d，J＝0.95Hz，J＝0.94Hz，1H).MS-EI?m/e：475(100％)[M +]，476(20.71％)[M ++1]，417(31.80％)，207(13.84％).
Standardized solution (1 * 10 at tetrahydrofuran (THF) -5M) in, the ultraviolet-visible maximum absorption band is respectively 303nm and 392nm, and its fluorescent emission maximum peak is at 513nm.
Embodiment 7
4-dimethylin-N-[4-(2-benzoxazolyl) phenyl]-1,8-naphthalimide synthetic:
1) 4-dimethylin-1, the preparation of 8-naphthalene acid anhydride
In there-necked flask, add 4.47g4-bromo-1,8-naphthalene acid anhydride, 2.1g dimethylamine, 80mL DMF, the anhydrous CuSO of 0.4g 4Reflux, reaction 7h.Reacting liquor while hot is poured in the 400ml mixture of ice and water, had orange precipitation to separate out.Suction filtration gets crude product.60 ℃ dry down.With the mixed solution 40mL recrystallization of chlorobenzene/dehydrated alcohol of 1: 1, get orange solids.Column chromatography separates, and obtains orange red pulverulent solids 3.71g, productive rate 52.4%.Fusing point 203-205 ℃.
(2) 4-dimethylin-N-[4-(2-benzoxazolyl) phenyl]-1, the preparation of 8-naphthalimide
With 4-dimethylin-1,8-naphthalene acid anhydride and 4-(2-benzoxazolyl) aniline makes target product (glassy yellow solid) by the synthetic method of (3) among the embodiment 1.Productive rate 35.9%.Fusing point＞300 ℃.
1H-NMR(CDCl 3)：3.18(s，6H)，7.20(d，J＝8.29Hz，1H)，7.40(t，2H)，7.51(d×d，J＝1.71Hz，J＝1.52Hz，2H)，7.62(d×d，J＝3.4Hz，J＝3.3Hz，1H)，7.73(t，1H)，7.82(d×d，J＝3.12Hz，J＝3.39Hz，1H)，8.45(d×d，J＝1.74Hz，J＝1.82Hz，2H)，8.55(d，J＝8.06Hz，1H)，8.57(d，J＝8.19Hz，1H)，8.65(d，J＝7.31Hz，1H).
MS-EI?m/e：433(100％)[M +]，434(25.66％)[M ++1]，223(16.36％).
Standardized solution (1 * 10 at tetrahydrofuran (THF) -5M) in, the ultraviolet-visible maximum absorption band is respectively 302nm and 412nm, and its fluorescent emission maximum peak is at 513nm.
Embodiment 8
4-dimethylin-N-[4-(2-[4-morpholinodithio base) phenyl]-1,8-naphthalimide synthetic:
Figure A20041001656700101
With 4-dimethylin-1,8-naphthalene acid anhydride and 4-(2-[4-morpholinodithio base) aniline makes target product (glassy yellow solid) by the synthetic method of (3) among the embodiment 1.Productive rate 30.3%.Fusing point＞300 ℃.
1H-NMR(CDCl 3)：3.16(s，6H)，7.17(d，J＝8.30Hz，1H)，7.42(t，1H)，7.48(d×d，J＝1.49Hz，J＝1.72Hz，2H)，7.52(t，1H)，7.72(t，1H)，7.94(d，J＝7.9Hz，1H)，8.12(d，J＝8.1Hz，1H)，8.28(d×d，J＝3.93Hz，J＝3.98Hz，2H)，8.52(d×d，J＝0.85Hz，J＝0.85Hz，1H)，8.55(d，J＝8.18Hz，1H)，8.64(d×d，J＝0.88J＝0.89Hz.1H).MS-EI?m/e：449(100％)[M +]，450(20.36％)[M ++1]，223(12.12％).
Standardized solution (1 * 10 at tetrahydrofuran (THF) -5M) in, the ultraviolet-visible maximum absorption band is respectively 302nm and 411nm, and its fluorescent emission maximum peak is at 512nm.
Embodiment 9
4-dimethylin-N-[4-(2-benzimidazolyl-) phenyl]-1,8-naphthalimide synthetic:
Figure A20041001656700111
With 4-dimethylin-1,8-naphthalene acid anhydride and 4-(2-benzimidazolyl-) aniline makes target product (glassy yellow solid) by the synthetic method of (3) among the embodiment 1.Productive rate 26.7%.Fusing point＞300 ℃.
1H-NMR(CDCl 3)：3.18(s，6H)，7.17(d，J＝8.29Hz，1H)，7.33(t，2H)，7.41(d，J＝8.15Hz，2H)，7.64(d，2H)，7.72(t，1H)，8.09(d，J＝8.15Hz，2H)，8.53(d，J＝8.48Hz，1H)，8.57(d，J＝8.27Hz，1H)，8.66(d，J＝7.22Hz，1H).MS-EI?m/e：432(100％)[M +]，433(19.42％)[M ++1]，223(13.52％).
Standardized solution (1 * 10 at tetrahydrofuran (THF) -5M) in, the ultraviolet-visible maximum absorption band is respectively 307nm and 411nm, and its fluorescent emission maximum peak is at 512nm.
Embodiment 10
Figure A20041001656700112
In flask, add the 50mg tri acetylacetonato and close iridium [Ir (acac) 3], 190mg 4-piperidyl-N-[4-(2-benzimidazolyl-) phenyl]-1,8-naphthalimide, 25mL glycerine.About 120 ℃ of 2h that bleed, argon shield, stirring, backflow 24h.Naturally be chilled to room temperature, a small amount of salmon precipitation is separated out.There is precipitation to separate out after adding entry.Suction filtration gets crude product.Column chromatography for separation gets orange red crystal.
Embodiment 11
As electroluminescent material, prepare electroluminescent device with the compound among the embodiment 3, the material and the structural parameter of each layer are as follows:
Glass substrate //ITO//CuPc (10nm)/TPD (10nm)/luminescent material (30nm) //LiF (7nm)/AlLi;
The element manufacturing program is as follows: matrix adopts the ito glass of ultrasonic cleansing, and its resistance is 20 Ω/, the negative electrode (0.28cm of device 2) and organic thin film layer be to adopt vacuum vapour deposition coating (vacuum tightness is 1 * 10 -7Torr), wherein TPD is N, N '-triphenyl diamines, and CuPc is a copper phthalocyanine, plays the hole transport effect.The thickness of device is measured with step instrument (Tenco Alpha-step 500), and the electroluminescent spectrogram is to measure with PTI QM1 luminoscope.When driving voltage was 20V, the maximum emission wavelength in its electroluminescent peak was 521nm, shinny gold-tinted, and maximum luminance is 4600cd/m 2, current density is 400mA/cm 2Device through 48 hours continuously luminous after, luminosity still can maintain 100cd/m 2More than.
Embodiment 12
As electroluminescent material, prepare electroluminescent device with the compound among the embodiment 10, the material and the structural parameter of each layer are as follows:
Glass substrate //ITO//luminescent material (83nm) //LiF (7nm)/AlLi;
Element manufacturing program and test similar embodiment 11.When driving voltage was 20V, the maximum emission wavelength in its electroluminescent peak was 650nm, glows, and maximum luminance is 4800cd/m 2, current density is 350mA/cm 2Device through 48 hours continuously luminous after, luminosity still can maintain 100cd/m 2More than.

Claims (1)

1,1 of a kind of electroluminescent phosphorescence or fluorescence, the 8-naphthalimide derivative, its structure is shown below:
Figure A2004100165670002C1
Or
In the formula: X is S, O or N; M is metal iridium or europium; R is a kind of in the following groups:
Figure A2004100165670002C3
Wherein: R 1, R 2Be a kind of in methyl, the ethyl.
CN 200410016567 2004-02-26 2004-02-26 Derivant of electrophosphorescence 1,8-naphthimide and luminous ligand thereof Expired - Fee Related CN1259317C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN 200410016567 CN1259317C (en) 2004-02-26 2004-02-26 Derivant of electrophosphorescence 1,8-naphthimide and luminous ligand thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN 200410016567 CN1259317C (en) 2004-02-26 2004-02-26 Derivant of electrophosphorescence 1,8-naphthimide and luminous ligand thereof

Publications (2)

Publication Number Publication Date
CN1560052A true CN1560052A (en) 2005-01-05
CN1259317C CN1259317C (en) 2006-06-14

Family

ID=34440539

Family Applications (1)

Application Number Title Priority Date Filing Date
CN 200410016567 Expired - Fee Related CN1259317C (en) 2004-02-26 2004-02-26 Derivant of electrophosphorescence 1,8-naphthimide and luminous ligand thereof

Country Status (1)

Country Link
CN (1) CN1259317C (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102226083A (en) * 2011-04-22 2011-10-26 南京邮电大学 Iridium complex phosphorescent materials with wavelengths from infrared to near-infrared range and preparation method thereof
CN102391309A (en) * 2011-09-09 2012-03-28 福州大学 Ruthenium coordination compound based on unit containing naphthalimide and synthesis method thereof
CN103450176A (en) * 2013-08-15 2013-12-18 大连理工大学 Naphthalimide compound containing 2-(4-aminophenyl) benzothiazole and application thereof
CN103992787A (en) * 2014-04-29 2014-08-20 贵州大学 Tris [4-(4-morpholine)-1, 8-naphthalimide ethyl] amine fluorescent reagent and preparation and application thereof
CN104059062A (en) * 2014-06-05 2014-09-24 大连理工大学 Benzothiazole and triazolediheterocycle-containing fused ring compound and application thereof
CN104650067A (en) * 2014-08-05 2015-05-27 吉林奥来德光电材料股份有限公司 Green material, preparation method and application thereof
CN105294772A (en) * 2015-11-10 2016-02-03 南京邮电大学 Electrophosphorescent discoloration neutral iridium complex and preparation method thereof

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102226083B (en) * 2011-04-22 2014-05-07 南京邮电大学 Iridium complex phosphorescent materials with wavelengths from infrared to near-infrared range and preparation method thereof
CN102226083A (en) * 2011-04-22 2011-10-26 南京邮电大学 Iridium complex phosphorescent materials with wavelengths from infrared to near-infrared range and preparation method thereof
CN102391309A (en) * 2011-09-09 2012-03-28 福州大学 Ruthenium coordination compound based on unit containing naphthalimide and synthesis method thereof
CN102391309B (en) * 2011-09-09 2013-12-04 福州大学 Ruthenium coordination compound based on unit containing naphthalimide and synthesis method thereof
CN103450176B (en) * 2013-08-15 2016-07-06 大连理工大学 One class is containing 2-(4-aminophenyl) benzothiazole naphthalimide compound and application thereof
CN103450176A (en) * 2013-08-15 2013-12-18 大连理工大学 Naphthalimide compound containing 2-(4-aminophenyl) benzothiazole and application thereof
CN103992787A (en) * 2014-04-29 2014-08-20 贵州大学 Tris [4-(4-morpholine)-1, 8-naphthalimide ethyl] amine fluorescent reagent and preparation and application thereof
CN103992787B (en) * 2014-04-29 2016-09-28 贵州大学 A kind of three [4-(4-morpholine base)-1,8-naphthalimide ethyl] amine fluorometric reagents and preparation thereof and application
CN104059062A (en) * 2014-06-05 2014-09-24 大连理工大学 Benzothiazole and triazolediheterocycle-containing fused ring compound and application thereof
CN104059062B (en) * 2014-06-05 2017-06-27 大连理工大学 Fused ring compound and its application containing benzothiazole and the double heterocycles of triazole
CN104650067A (en) * 2014-08-05 2015-05-27 吉林奥来德光电材料股份有限公司 Green material, preparation method and application thereof
CN104650067B (en) * 2014-08-05 2017-11-21 吉林奥来德光电材料股份有限公司 A kind of green light material and its preparation method and application
CN105294772A (en) * 2015-11-10 2016-02-03 南京邮电大学 Electrophosphorescent discoloration neutral iridium complex and preparation method thereof
CN105294772B (en) * 2015-11-10 2018-11-09 南京邮电大学 A kind of neutral complex of iridium of electroluminescent phosphorescence discoloration and its preparation

Also Published As

Publication number Publication date
CN1259317C (en) 2006-06-14

Similar Documents

Publication Publication Date Title
CN1173980C (en) Organometallic complex molecule and organic electroluminescent device using the same
CN1157461C (en) Bispirocyclo derivative and its application in electroluminescent material
RU2427058C1 (en) Organic light-emitting device and display apparatus
CN1649886A (en) Electroluminescent materials
CN1711334A (en) Material for organic electroluminescent device and organic electroluminescent device using the same
CN100383151C (en) Iridium complex of beta-diketone ligand and its electroluminescent device
CN1259317C (en) Derivant of electrophosphorescence 1,8-naphthimide and luminous ligand thereof
TWI520967B (en) Organic metal compounds and organic electroluminescence devices employing the same
KR20110014752A (en) Organic electroluminescence device for a red phosphorescence and method for manufacturing of the same
KR20110070180A (en) Blue fluorescence compound and organic electroluminescence device using the same
TWI728594B (en) Organic metal compound and organic light-emitting device
CN1910260A (en) Materials for electroluminescent devices
CN1246417C (en) Electroluminescent organic material and its application
CN1395454A (en) organic electroluminescent device
CN1259312C (en) Compound of substituted benzo heterocyclic by electrophosphorescence and luminous ligand thereof
CN1803970A (en) Organic metal complex and organic electro photoluminescence device comprising the same
KR101693613B1 (en) Compound, organic optoelectric device and display device
CN1240808C (en) Organic electroluminescent material of dendritic macromolecular naphthalene imide
TWI662043B (en) Organic metal compound and organic light-emitting device
CN1139649C (en) Organic electroluminescent material
CN1219018C (en) Red fluorescent dye possessing star project type structure and its synthesis method and use
CN1303083C (en) Red organic electroluminescent material
CN108365127A (en) A kind of organic semiconductive material and its organic luminescent device
CN1673312A (en) Light-emitting material and organic electroluminescent device therewith
CN1239672C (en) Electroluminescent phosphorescence material and its application

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
C17 Cessation of patent right
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20060614

Termination date: 20100226