CN1362464A - Organic electroluminescent material - Google Patents

Organic electroluminescent material Download PDF

Info

Publication number
CN1362464A
CN1362464A CN 02100371 CN02100371A CN1362464A CN 1362464 A CN1362464 A CN 1362464A CN 02100371 CN02100371 CN 02100371 CN 02100371 A CN02100371 A CN 02100371A CN 1362464 A CN1362464 A CN 1362464A
Authority
CN
China
Prior art keywords
methyl
following structure
hydrogen atom
electroluminescent organic
naphthyl
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
CN 02100371
Other languages
Chinese (zh)
Other versions
CN1239447C (en
Inventor
邱勇
厉斌
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.)
Tsinghua University
Original Assignee
Tsinghua University
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 Tsinghua University filed Critical Tsinghua University
Priority to CN 02100371 priority Critical patent/CN1239447C/en
Publication of CN1362464A publication Critical patent/CN1362464A/en
Application granted granted Critical
Publication of CN1239447C publication Critical patent/CN1239447C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Images

Landscapes

  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

本发明涉及一种有机电致发光材料,属于电子材料技术领域。该材料为多取代蒽的衍生物,其特征在于,该材料具有右式结构,其中取代基R1－R10可以是氢原子、烷基、异烷基、羟基、烷氧基、硝基、氰基、氨基、巯基、卤素原子、三氟甲基、芳香基或杂环取代基(呋喃、噻吩、吡咯、吡啶、吡喃、喹啉、吲哚、咔唑)中的一种。本发明中的材料可作为有机电致发光器件的有机发光层中的发光材料,包括单独成为发光层和作为掺杂的染料而发光,同时还具有较好的载流子传输能力,克服了现有材料中存在的发光效率低、成膜性能不好等缺点,在液体和固体膜中都有较强的荧光,发光颜色可调谐,热稳定性好,具有较好的载流子传输性能,可以形成良好的无定形薄膜。

Figure 02100371

The invention relates to an organic electroluminescent material, which belongs to the technical field of electronic materials. The material is a derivative of multi-substituted anthracene, which is characterized in that the material has a structure of the right formula, wherein the substituents R 1 -R 10 can be hydrogen atoms, alkyl groups, isoalkyl groups, hydroxyl groups, alkoxy groups, nitro groups, One of cyano, amino, mercapto, halogen atom, trifluoromethyl, aryl or heterocyclic substituent (furan, thiophene, pyrrole, pyridine, pyran, quinoline, indole, carbazole). The material in the present invention can be used as a light-emitting material in the organic light-emitting layer of an organic electroluminescent device, including being a light-emitting layer alone or as a doped dye to emit light, and also has a good carrier transport ability, which overcomes the existing There are disadvantages such as low luminous efficiency and poor film-forming performance in the material, strong fluorescence in both liquid and solid films, tunable luminous color, good thermal stability, and good carrier transport performance. Good amorphous films can be formed.

Figure 02100371

Description

A kind of electroluminescent organic material
Technical field:
The present invention relates to a kind of electroluminescent organic material, belong to technical field of electronic materials.
Background technology:
Now, along with the arriving of Development of Multimedia Technology and information society, more and more higher to the flat-panel monitor performance demands.In recent years emerging three kinds of technique of display: plasma display, Field Emission Display and display of organic electroluminescence (OLED) have all remedied the deficiency of cathode tube and liquid-crystal display to a certain extent.Wherein, a series of advantages such as the organic film El element has from main light emission, low voltage direct drive, solidifies entirely, the visual angle is wide, color is abundant, compare with liquid-crystal display, OLED does not need backlight, and the visual angle is big, and power is low, its response speed can reach 1000 times of liquid-crystal display, its manufacturing cost but is lower than equal resolving power and reaches liquid-crystal display, and therefore, display of organic electroluminescence certainly will have broad application prospects.
Adopting well behaved luminescent material is the important foundation of this type of OLED device of preparation.The patent No. is to have mentioned the employing small organic molecule as luminescent material in 4,539,507 the United States Patent (USP), but small molecule material has a lot of shortcomings, and is bad as film forming properties, and easily crystallization etc.Begin one's study in recent years and use polymkeric substance, but the luminous efficiency of general polymerization thing is lower than small molecule material as luminous organic material.So, seek and a kind ofly have higher luminous efficiency, and in film process, be difficult for the key issue that the crystalline material becomes OLED material technology field.
The typical structure of OLED comprises cathode layer, anode layer, and the organic luminous layer between this is two-layer, can comprise one or more functional layers in electron transfer layer, hole transmission layer and the luminescent layer in the organic luminous layer.Generally include main body luminescent material and adulterate body material in the luminescent layer, the main body luminescent material as in the luminescent layer should possess fluorescent effect preferably, and its wavelength of fluorescence should be near blue light or ultraviolet light wavelength.In blue fluorescent material, anthracene derivative particularly 9,10-dibenzanthracene, in solution, still all have fluorescent effect preferably under the solid conditions, still, as main body luminescent material 9, the film forming characteristics of 10-dibenzanthracene is bad, easily crystallization and cause the device short circuit.So, a lot of patents and document being arranged to 9, this material of 10-dibenzanthracene has proposed improvement, and the patent No. is to have proposed 9 of a kind of dimeric structure in the patent of EP0681019,10-dibenzanthracene, promptly 9, the derivative of the ammonia of 10-dibenzanthracene.The patent US5 of Kodak company, 935,721 propose a class 9, the derivative of 10-two-(2-naphthalene) anthracene, the patent US5 in Kodak company, 972, one class 9 is also proposed in 247, the derivative of 10-two (3 ', 5 '-two aromatic base substituted benzenes) anthracene, this two classes material have higher second-order transition temperature and good fluorescent effect.In the patent EP1009044 of Kodak company, propose to can be used as hole transmission layer in addition and prepare high performance electroluminescent device with four derivatives that replace anthracene.
The anthracene derivative that proposes in the above-mentioned patent has good luminous property, but because the restriction of substituting group number and kind makes that its luminous efficiency, film-forming properties, glow color, carrier transport ability etc. are limited to.For further improving the luminous efficiency of anthracene derivative, improve film-forming properties, tuning glow color strengthens carrier transport ability, and we propose with polysubstituted anthracene derivant as twinkler or carrier transmission material.
Summary of the invention: the technical problem that solve:
The objective of the invention is to propose the novel fluorescent material of a class, can be used as luminescent material in the organic luminous layer, can be thereby expanded for the kind of the organic compound for preparing the organic luminescent device use.Material among the present invention can be used as twinkler, and comprising becomes luminescent layer separately and as adulterated dyestuff and luminous, also have carrier transport ability preferably simultaneously.The compounds of this invention all has stronger fluorescence in liquid and solid film, have goodish heat, light equistability simultaneously again.Technical scheme:
The present invention proposes a kind of electroluminescent organic material, and this material is the derivative of anthracene, it is characterized in that this luminescent material has following structure shown in Figure 1:
Figure A0210037100141
Fig. 1
In the said structure formula, substituent R 1-R 10Can be a kind of in hydrogen atom, alkyl, iso-alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, trifluoromethyl, aromatic base or the heterocyclic substituent (furans, thiophene, pyrroles, pyridine, pyrans, quinoline, indoles, carbazole).
In the structure shown in Figure 1, preferred typical compound is I-XV totally 15 types with structure shown in Figure 2:
In the structure shown in Figure 2, substituent R 1-R 10Can be identical or different, can be the group that a hydrogen or 1-24 carbon atom and other heteroatomss are formed, for example alkyl (methyl, ethyl etc.), iso-alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfenyl, halogen atom, trifluoromethyl, aromatic base (phenyl, naphthyl etc.), heterocyclic substituent (furans, thiophene, pyrroles, pyridine, pyrans, quinoline, indoles, carbazole etc.) etc.
Preferred typical substituted radical is listed in the table one.
Figure A0210037100151
Fig. 2 table one: substituted radical table
Figure A0210037100161
The I compounds, preferred substituted R 1-R 4Can be among the group A1-A36 in the identical or different top table one, also can be other groups of being made up of 1-24 carbon atom and heteroatoms.Particularly preferred compound is that I-1 is to I-16 in the I class formation.
Figure A0210037100171
The II compounds, preferred substituted R 1-R 4Can be among the group A1-A36 in the identical or different top table one, also can be other groups of being made up of 1-24 carbon atom and heteroatoms.Particularly preferred compound is that II-1 is to II-16 in the II class formation.
The III compounds, preferred substituted R 1-R 4Can be among the group A1-A36 in the identical or different top table one, also can be other groups of being made up of 1-24 carbon atom and heteroatoms.Particularly preferred compound is that III-1 is to III-16 in the III class formation.
Figure A0210037100191
The IV compounds, preferred substituted R 1-R 4Can be among the group A1-A36 in the identical or different top table one, also can be other groups of being made up of 1-24 carbon atom and heteroatoms.Particularly preferred compound is that IV-1 is to IV-16 in the IV class formation.
Figure A0210037100201
The V compounds, preferred substituted R 1-R 5Can be among the group A1-A36 in the identical or different top table one, also can be other groups of being made up of 1-24 carbon atom and heteroatoms.Particularly preferred compound is that V-1 is to V-16 in the V class formation.
Figure A0210037100211
The VI compounds, preferred substituted R 1-R 4Can be among the group A1-A36 in the identical or different top table one, also can be other groups of being made up of 1-24 carbon atom and heteroatoms.Particularly preferred compound is that VI-1 is to VI-16 in the VI class formation.
Figure A0210037100221
The VII compounds, preferred substituted R 1-R 6Can be among the group A1-A36 in the identical or different top table one, also can be other groups of being made up of 1-24 carbon atom and heteroatoms.Particularly preferred compound is that VII-1 is to VII-16 in the VII class formation.
Figure A0210037100231
The VIII compounds, preferred substituted R 1-R 6Can be among the group A1-A36 in the identical or different top table one, also can be other groups of being made up of 1-24 carbon atom and heteroatoms.Particularly preferred compound is that VIII-1 is to VIII-16 in the VIII class formation.
Figure A0210037100241
The IX compounds, preferred substituted R 1-R 6Can be among the group A1-A36 in the identical or different top table one, also can be other groups of being made up of 1-24 carbon atom and heteroatoms.Particularly preferred compound is that IX-1 is to IX-16 in the IX class formation.
The X compounds, preferred substituted R 1-R 6Can be among the group A1-A36 in the identical or different top table one, also can be other groups of being made up of 1-24 carbon atom and heteroatoms.Particularly preferred compound is that X-1 is to X-16 in the X class formation.
Figure A0210037100261
The XI compounds, preferred substituted R 1-R 6Can be among the group A1-A36 in the identical or different top table one, also can be other groups of being made up of 1-24 carbon atom and heteroatoms.Particularly preferred compound is that XI-1 is to XI-16 in the XI class formation.
The XII compounds, preferred substituted R 1-R 6Can be among the group A1-A36 in the identical or different top table one, also can be other groups of being made up of 1-24 carbon atom and heteroatoms.Particularly preferred compound is that XII-1 is to XII-16 in the XII class formation.
Figure A0210037100281
The XIII compounds, preferred substituted R 1-R 6Can be among the group A1-A36 in the identical or different top table one, also can be other groups of being made up of 1-24 carbon atom and heteroatoms.Particularly preferred compound is that XIII-1 is to XIII-16 in the XIII class formation.
Figure A0210037100291
The XIV compounds, preferred substituted R 1-R 6Can be among the group A1-A36 in the identical or different top table one, also can be other groups of being made up of 1-24 carbon atom and heteroatoms.Particularly preferred compound is that XIV-1 is to XIV-16 in the XIV class formation.
Figure A0210037100301
The XV compounds, preferred substituted R 1-R 10Can be among the group A1-A36 in the identical or different top table one, also can be other groups of being made up of 1-24 carbon atom and heteroatoms.Particularly preferred compound is that XV-1 is to XV-16 in the XV class formation.
Figure A0210037100311
Luminous organic material of the present invention mainly adopts the organometallic reagent (lithium reagent, Grignard reagent etc.) and the method for substituted anthraquinone addition to prepare, and the step of employing comprises the preparation of (1) substituted anthraquinone; (2) preparation of organometallic reagent (lithium reagent, Grignard reagent etc.); (3) organometallic reagent (lithium reagent, Grignard reagent etc.) prepares the anthrol intermediate with the substituted anthraquinone addition; (4) anthrol intermediate dehydration reduction obtains target product.Beneficial effect:
Luminous organic material of the present invention has following characteristics: fluorescence is strong, and glow color is tunable, and Heat stability is good has carrier transmission performance preferably, can form good amorphous thin film.
Description of drawings:
The nuclear magnetic resonance spectrum of the Compound I-4 of Fig. 1 the present invention preparation.
Fig. 2 N, N '-phenylbenzene-N, N '-two (1-naphthyl)-1,1 '-biphenyl-4,4 '-diamines (NPB), oxine aluminium (AlQ 3) structural formula.
Fig. 3 is the electroluminescent spectrum figure with the prepared device one of Compound I-4 of the present invention's preparation.
Fig. 4 be with the prepared device one of Compound I-4 of the present invention preparation current-voltage curve.
Fig. 5 be with the prepared device one of Compound I-4 of the present invention preparation brightness-voltage curve.
Embodiment:
Below introduce embodiments of the invention.
The embodiment of compound sample preparation:
Benzene is invented the synthetic of used part substituted anthraquinone intermediate
2,3-dimethyl anthraquinone is synthetic according to document (Org.Synth., 1942,22,37) method.1,2-dimethyl anthraquinone is synthetic according to document (J.Chem.Soc., 1940,16) method.1,3-dimethyl anthraquinone is synthetic according to document (J.Am.Chem.Soc., 1954,76,6150) method.1,4-dimethyl anthraquinone is synthetic according to document (J.Chem.Soc., 1952,2415) method.1,2,3,4-tetramethyl-anthraquinone is synthetic according to document (Aust.J.Chem., 1971,24,2137) method.1,2,5,6-tetramethyl-anthraquinone is synthetic according to document (J.Am.Chem.Soc., 1947,69,2256) method.1,3,5,7-tetramethyl-anthraquinone, 1,3,6,8-tetramethyl-anthraquinone, 1,4,5,8-tetramethyl-anthraquinone is synthetic according to document (J.Chem.Soc (C), 1967,2607) method.1,3,6,7-tetramethyl-anthraquinone, 1,4,6,7-tetramethyl-anthraquinone is synthetic according to document (J.Chem.Soc, 1938,1847) method.2,3,6,7-tetramethyl-anthraquinone is synthetic according to document (Org.Prep.Proced.Int., 1972,4,211) method.1,4-phenylbenzene anthraquinone and 1,4,5,8-tetraphenyl anthraquinone is synthetic according to document (J.Org.Chem., 1942,7,305) method.1,2,3,4,5,6,7,8-prestox anthraquinone is synthetic according to document (Recl.Trav.Chim.Pays-Bas, 1939,38,761) method.
Embodiment 1,3-dimethyl-9, and 10-diphenylanthrancene (Compound I-1):
(1) .2,3-dimethyl-9,10-diphenylanthrancene diphenol
In 250 milliliters of three-necked bottles being furnished with constant pressure funnel, reflux condensing tube and nitrogen protection device, add 0.3 gram metal magnesium chips and 10 milliliters of anhydrous diethyl ethers; add a granule iodine as initiator; 1.9 gram bromobenzenes are dissolved in 25 milliliters of solution in the anhydrous diethyl ether to splash in the three-necked bottle from constant pressure funnel; rate of addition is advisable to keep slight backflow of reaction system; dropwise; refluxed 2 hours, and obtained the diethyl ether solution of bromobenzene Grignard reagent.
Add 1.2 grams 2 in the Grignard reagent of making, 3-dimethyl anthraquinone adds 50 milliliters of dry toluenes more in batches, steam and remove ether, reflux to stir and spend the night, the cooling back adds 100 milliliters of frozen water, 50 milliliters of dilute hydrochloric acid, 100 milliliters of ethyl acetate, branch vibration layer, the organic layer evaporated under reduced pressure gets white solid 2,3-dimethyl-9,10-diphenylanthrancene diphenol 1.2 grams.Yield 60%.
(2) .2,3-dimethyl-9,10-diphenylanthrancene
The oxanthranol 1.2 gram addings that the last step obtains are furnished with in 100 milliliters of round-bottomed flasks of reflux condensing tube, add 30 milliliters of Glacial acetic acid and 3 gram tin protochlorides, reflux, there is yellow solid to separate out, is cooled to 60 degree, filter, be washed to neutrality, drying is used silica gel chromatography, obtains yellow solid 0.8 gram.Yield 70%.
MS(m/z)：359。Ultimate analysis (C 28H 22): theoretical value C:93.85%, H:6.15%; Measured value C:94.01%, H:5.99%.
Embodiment 22,3-dimethyl-9, and 10-two (1-naphthyl) anthracene (Compound I-2):
With 1-naphthalene bromide and 2,3-dimethyl anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：459。Ultimate analysis (C 36H 26): theoretical value C:94.12%, H:5.88%; Measured value C:94.28%, H:5.72%.
Embodiment 32,3-dimethyl-9, and 10-two (1-naphthyl) anthracene (Compound I-3):
With 2-naphthalene bromide and 2,3-dimethyl anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：459。Ultimate analysis (C 36H 26): theoretical value C:94.12%, H:5.88%; Measured value C:94.32%, H:5.69%.
Embodiment 42,3-dimethyl-9, and 10-two (2-methyl isophthalic acid-naphthyl) anthracene (Compound I-4):
With 2-methyl isophthalic acid-naphthalene bromide and 2,3-dimethyl anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：487。Ultimate analysis (C 38H 30): theoretical value C:93.83%, H:6.17%; Measured value C:93.98%, H:6.02%.
Embodiment 52,3-dimethyl-9, and 10-two (3 ' .5 '-phenylbenzene-phenyl) anthracene (Compound I-5):
(1) 2,3-dimethyl-9,10-two (3 ' .5 '-dibromo phenyl) anthracene
(12 milliliters of diethyl ether solutions that in 250 milliliters of three-necked bottles being furnished with constant pressure funnel, reflux condensing tube and nitrogen protection device, add n-Butyl Lithium; 0.02mol; 1.7mol/L), be cooled to-20 ° with the dry ice-propanone bath, splash into 1; 3; (3.15 restrain the 5-tribromo-benzene, 0.01mol) are dissolved in the solution of 25 milliliters of ether, dropwise and stir 1 hour; obtain 3, the diethyl ether solution of 5-dibromo phenyl lithium.To this 3, add 2 in the diethyl ether solution of 5-dibromo phenyl lithium, 3-dimethyl anthraquinone (1.1 the gram, 0.005mol) 50 milliliters of toluene solutions, steam to remove ether, backflow is spent the night, after the cooling, add 100 milliliters of frozen water, 50 milliliters of dilute hydrochloric acid, 100 milliliters of ethyl acetate, branch vibration layer, the organic layer evaporated under reduced pressure gets solid 2,3-dimethyl-9,10-two (3 ' .5 '-dibromo phenyl) oxanthranol.
The oxanthranol adding that the last step obtains is furnished with in 100 milliliters of round-bottomed flasks of reflux condensing tube, adds 30 milliliters of Glacial acetic acid and 3 gram tin protochlorides, reflux, there is yellow solid to separate out, be cooled to 60 degree, filter, be washed to neutrality, dry, use silica gel chromatography, obtain 1.7 gram yellow solids 2,3-dimethyl-9,10-two (3 ' .5 '-dibromo phenyl) anthracene, yield 50%.
(2) in 250 milliliters of three-necked bottles being furnished with constant pressure funnel, reflux condensing tube and nitrogen protection device, add 0.3 gram metal magnesium chips and 10 milliliters of anhydrous tetrahydro furans; add a granule iodine as initiator; 1.9 gram bromobenzenes are dissolved in 25 milliliters of solution in the anhydrous tetrahydro furan to splash in the three-necked bottle from constant pressure funnel; rate of addition is advisable to keep slight backflow of reaction system; dropwise; refluxed 2 hours, and obtained the tetrahydrofuran solution of bromobenzene Grignard reagent.
With 1.7 grams 2; 3-dimethyl-9; 10-two (3 ' .5 '-dibromo phenyl) anthracene (2.5mmol) and two (triphenylphosphine) Palladous chlorides of 0.1 gram are dissolved in 50 milliliters of anhydrous tetrahydro furans, the tetrahydrofuran solution of the bromobenzene Grignard reagent that the step makes in the dropping, and nitrogen protection refluxes down and stirred 5 hours.Cooling carefully adds 50 milliliters of tetrahydrofuran (THF)s and 25 milliliter of 15% hydrochloric acid, and rotary evaporation in vacuo is removed solvents tetrahydrofurane, filters residuum, is washed with water to neutrality.Refluxed one hour in 500 milliliters of methylene dichloride of thick product adding, cooling is filtered, and with the small amount of acetone washing, gets 1.0 grams 2,3-dimethyl-9,10-two (3 ' .5 '-phenylbenzene-phenyl) anthracene, yield 60%.
MS(m/z)：662。Ultimate analysis (C 52H 38): theoretical value C:94.26%, H:5.74%; Measured value C:94.48%, H:5.52%.
Embodiment 62,3-dimethyl-9, and 10-two (3 ' .5 '-two (o-tolyl)-phenyl) anthracene (Compound I-6):
With o-bromotoluene and 2,3-dimethyl-9,10-two (3 ' .5 '-dibromo phenyl) anthracene is the synthetic method preparation of starting raw material by Compound I-5 among the embodiment five.
MS(m/z)：718。Ultimate analysis (C 56H 46): theoretical value C:93.59%, H:6.41%; Measured value C:93.46%, H:6.54%.
Embodiment 72,3-dimethyl-9, and 10-two (3 ' .5 '-two (tolyl)-phenyl) anthracene (Compound I-7):
With m-bromotoluene and 2,3-dimethyl-9,10-two (3 ' .5 '-dibromo phenyl) anthracene is the synthetic method preparation of starting raw material by Compound I-5 among the embodiment five.
MS(m/z)：718。Ultimate analysis (C 56H 46): theoretical value C:93.59%, H:6.41%; Measured value C:93.37%, H:6.63%.
Embodiment 82,3-dimethyl-9, and 10-two (3 ' .5 '-two (p-methylphenyl)-phenyl) anthracene (Compound I-8):
With para-bromo toluene and 2,3-dimethyl-9,10-two (3 ' .5 '-dibromo phenyl) anthracene is the synthetic method preparation of starting raw material by Compound I-5 among the embodiment five.
MS(m/z)：718。Ultimate analysis (C 56H 46): theoretical value C:93.59%, H:6.41%; Measured value C:93.66%, H:6.34%.
Embodiment 92,3-dimethyl-9, and 10-two (3 ' .5 '-two (1-naphthyl)-phenyl) anthracene (Compound I-9):
With 1-naphthalene bromide and 2,3-dimethyl-9,10-two (3 ' .5 '-dibromo phenyl) anthracene is the synthetic method preparation of starting raw material by Compound I-5 among the embodiment five.
MS(m/z)：862。Ultimate analysis (C 68H 46): theoretical value C:94.66%, H:5.34%; Measured value C:94.56%, H:5.44%.
Embodiment 10,3-dimethyl-9, and 10-two (3 ' .5 '-two (2-naphthyl)-phenyl) anthracene (Compound I-10):
With 2-naphthalene bromide and 2,3-dimethyl-9,10-two (3 ' .5 '-dibromo phenyl) anthracene is the synthetic method preparation of starting raw material by Compound I-5 among the embodiment five.
MS(m/z)：862。Ultimate analysis (C 68H 46): theoretical value C:94.66%, H:5.34%; Measured value C:94.48%, H:5.52%.
Embodiment 11,3-dimethyl-9, and 10-two (3 ' .5 '-two (2-methyl isophthalic acid-naphthyl)-phenyl) anthracene (Compound I-11):
With 2-methyl isophthalic acid-naphthalene bromide and 2,3-dimethyl-9,10-two (3 ' .5 '-dibromo phenyl) anthracene is the synthetic method preparation of starting raw material by Compound I-5 among the embodiment five.
MS(m/z)：918。Ultimate analysis (C 72H 54): theoretical value C:94.12%, H:5.88%; Measured value C:94.26%, H:5.74%.
Embodiment 12,3-dimethyl-9, and 10-two (3 ' .5 '-difluorophenyl) anthracene (Compound I-12):
With 3.5-difluoro bromobenzene and 2,3-dimethyl anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one.
MS(m/z)：430。Ultimate analysis (C 28H 18F 4): theoretical value C:78.14%, H:4.19%; Measured value C:78.32%, H:4.34%.
Embodiment 13,3-dimethyl-9,10-two (4 '-trifluoromethyl-phenyl) anthracene (I-13)
With 4-trifluoromethyl-bromobenzene and 2,3-dimethyl anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：494。Ultimate analysis (C 30H 20F 6): theoretical value C:72.87%, H:4.05%; Measured value C:73.05%, H:4.12%.
Embodiment 14,4-dimethyl-9, and 10-two (1-naphthyl) anthracene (Compound I I-2):
With 1-naphthalene bromide and 1,4-dimethyl anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：459。Ultimate analysis (C 36H 26): theoretical value C:94.12%, H:5.88%; Measured value C:94.38%, H:5.62%.
Embodiment 15,4-dimethyl-9, and 10-two (2-methyl isophthalic acid-naphthyl) anthracene (Compound I I-4):
With 2-methyl isophthalic acid-naphthalene bromide and 1,4-dimethyl anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：487。Ultimate analysis (C 38H 30): theoretical value C:93.83%, H:6.17%; Measured value C:93.68%, H:6.32%.
Embodiment 16, and 4,9,10-tetraphenyl anthracene (Compound I I-14):
1,4,9,10-tetraphenyl anthraquinone is synthetic according to document (J.Org.Chem., 1965,30,198) method.
MS(m/z)：482。Ultimate analysis (C 38H 26): theoretical value C:94.61%, H:5.39%; Measured value C:94.72%, H:5.28%.
Embodiment 17,4-phenylbenzene-9, and 10-two (1-naphthyl) anthracene (Compound I I-15):
With 1-naphthalene bromide and 1,4-phenylbenzene anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：582。Ultimate analysis (C 46H 30): theoretical value C:94.85%, H:5.15%; Measured value C:94.66%, H:5.34%.
Embodiment 18,4-phenylbenzene-9, and 10-two (2-methyl isophthalic acid-naphthyl) anthracene (Compound I I-16):
With 2-methyl isophthalic acid-naphthalene bromide and 1,4-phenylbenzene anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：610。Ultimate analysis (C 48H 34): theoretical value C:94.43%, H:5.57%; Measured value C:94.59%, H:5.41%.
Embodiment 19,3-dimethyl-9, and 10-two (1-naphthyl) anthracene (compound III-2):
With 1-naphthalene bromide and 1,3-dimethyl anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：459。Ultimate analysis (C 36H 26): theoretical value C:94.12%, H:5.88%; Measured value C:94.25%, H:5.75%.
Embodiment 20,3-dimethyl-9, and 10-two (2-methyl isophthalic acid-naphthyl) anthracene (compound III-4):
With 2-methyl isophthalic acid-naphthalene bromide and 1,3-dimethyl anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：487。Ultimate analysis (C 38H 30): theoretical value C:93.83%, H:6.17%; Measured value C:93.65%, H:6.35%.
Embodiment 21,2-dimethyl-9, and 10-two (1-naphthyl) anthracene (compound IV-2):
With 1-naphthalene bromide and 1,2-dimethyl anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：459。Ultimate analysis (C 36H 26): theoretical value C:94.12%, H:5.88%; Measured value C:94.18%, H:5.82%.
Embodiment 22,2-dimethyl-9, and 10-two (2-methyl isophthalic acid-naphthyl) anthracene (compound IV-4):
With 2-methyl isophthalic acid-naphthalene bromide and 1,2-dimethyl anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：487。Ultimate analysis (C 38H 30): theoretical value C:93.83%, H:6.17%; Measured value C:93.59%, H:6.41%.
Embodiment 23, and 2,3,4-tetramethyl--9,10-two (1-naphthyl) anthracene (compound VI I-2):
With 1-naphthalene bromide and 1,2,3,4-tetramethyl-anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：486。Ultimate analysis (C 38H 30): theoretical value C:93.83%, H:6.17%; Measured value C:94.02%, H:5.98%.
Embodiment 24, and 2,3,4-tetramethyl--9,10-two (2-methyl isophthalic acid-naphthyl) anthracene (compound VI I-4):
With 2-methyl isophthalic acid-naphthalene bromide and 1,2,3,4-tetramethyl-anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：515。Ultimate analysis (C 40H 34): theoretical value C:93.39%, H:6.61%; Measured value C:93.56%, H:6.44%.
Embodiment 25, and 2,3,4-tetraphenyl anthracene (compound VI I-16):
Synthetic according to document (J.Org.Chem., 1998,63,8579) method.
MS(m/z)：482。Ultimate analysis (C 38H 26): theoretical value C:94.61%, H:5.39%; Measured value C:94.54%, H:5.46%.
Embodiment 26, and 2,5,6-tetramethyl--9,10-two (1-naphthyl) anthracene (compound VIII-2):
With 1-naphthalene bromide and 1,2,5,6-tetramethyl-anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：486。Ultimate analysis (C 38H 30): theoretical value C:93.83%, H:6.17%; Measured value C:94.06%, H:5.94%.
Embodiment 27, and 2,5,6-tetramethyl--9,10-two (2-methyl isophthalic acid-naphthyl) anthracene (compound VIII-4):
With 2-methyl isophthalic acid-naphthalene bromide and 1,2,5,6-tetramethyl-anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：515。Ultimate analysis (C 40H 34): theoretical value C:93.39%, H:6.61%; Measured value C:93.54%, H:6.56%.
Embodiment 28, and 3,5,7-tetramethyl--9,10-two (1-naphthyl) anthracene (Compound I X-2):
With 1-naphthalene bromide and 1,3,5,7-tetramethyl-anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：486。Ultimate analysis (C 38H 30): theoretical value C:93.83%, H:6.17%; Measured value C:93.99%, H:6.01%.
Embodiment 29, and 3,5,7-tetramethyl--9,10-two (2-methyl isophthalic acid-naphthyl) anthracene (Compound I X-4):
With 2-methyl isophthalic acid-naphthalene bromide and 1,3,5,7-tetramethyl-anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：515。Ultimate analysis (C 40H 34): theoretical value C:93.39%, H:6.61%; Measured value C:93.21%, H:6.78%.
Embodiment 30, and 3,5,7-tetraphenyl anthracene (Compound I X-14):
1,3,5,7-tetraphenyl anthracene is synthetic according to document (Chem.Ber., 1966,99,934) method.
MS(m/z)：482。Ultimate analysis (C 38H 26): theoretical value C:94.61%, H:5.39%; Measured value C:94.68%, H:5.32%.
Embodiment hentriaconta-1,3,6,7-tetramethyl--9,10-two (1-naphthyl) anthracene (compounds X-2):
With 1-naphthalene bromide and 1,3,6,7-tetramethyl-anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：486。Ultimate analysis (C 38H 30): theoretical value C:93.83%, H:6.17%; Measured value C:93.89%, H:6.11%.
Embodiment 32, and 3,6,7-tetramethyl--9,10-two (2-methyl isophthalic acid-naphthyl) anthracene (compounds X-4):
With 2-methyl isophthalic acid-naphthalene bromide and 1,3,6,7-tetramethyl-anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：515。Ultimate analysis (C 40H 34): theoretical value C:93.39%, H:6.61%; Measured value C:93.29%, H:6.71%.
Embodiment 33, and 3,5,7-tetramethyl--9,10-two (1-naphthyl) anthracene (compounds X I-2):
With 1-naphthalene bromide and 1,3,5,7-tetramethyl-anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：486。Ultimate analysis (C 38H 30): theoretical value C:93.83%, H:6.17%; Measured value C:93.99%, H:6.01%.
Embodiment 34, and 3,6,8-tetramethyl--9,10-two (2-methyl isophthalic acid-naphthyl) anthracene (compounds X I-4):
With 2-methyl isophthalic acid-naphthalene bromide and 1,3,6,8-tetramethyl-anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：515。Ultimate analysis (C 40H 34): theoretical value C:93.39%, H:6.61%; Measured value C:93.57%, H:6.43%.
Embodiment 35, and 3,6,8-tetraphenyl anthracene (compounds X I-14):
1,3,6,8-tetraphenyl anthracene is synthetic according to document (Chem.Ber., 1966,99,934) method.
MS(m/z)：482。Ultimate analysis (C 38H 26): theoretical value C:94.61%, H:5.39%; Measured value C:94.70%, H:5.30%.
Embodiment 36, and 4,5,8-tetramethyl--9,10-two (1-naphthyl) anthracene (compounds X II-2):
With 1-naphthalene bromide and 1,4,5,8-tetramethyl-anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：486。Ultimate analysis (C 38H 30): theoretical value C:93.83%, H:6.17%; Measured value C:93.95%, H:6.05%.
Embodiment 37, and 4,5,8-tetramethyl--9,10-two (2-methyl isophthalic acid-naphthyl) anthracene (compounds X II-4):
With 2-methyl isophthalic acid-naphthalene bromide and 1,4,5,8-tetramethyl-anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：515。Ultimate analysis (C 40H 34): theoretical value C:93.39%, H:6.61%; Measured value C:93.25%, H:6.75%.
Embodiment 38, and 4,5,8-tetraphenyl anthracene (compounds X II-15):
1,4,5,8-tetraphenyl anthracene is synthetic according to document (Bull.Soc.Chim.Fr., 1963,2019) method.
MS(m/z)：482。Ultimate analysis (C 38H 26): theoretical value C:94.61%, H:5.39%; Measured value C:94.49%, H:5.51%.
Embodiment 39, and 4,5,8-tetraphenyl-9,10-dimethylanthracene (compounds X II-15):
With methyl iodide and 1,4,5,8-tetraphenyl anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：510。Ultimate analysis (C 40H 30): theoretical value C:94.12%, H:5.88%; Measured value C:94.24%, H:5.76%.
Embodiment 40, and 4,6,7-tetramethyl--9,10-two (1-naphthyl) anthracene (compounds X III-2):
With 1-naphthalene bromide and 1,4,6,7-tetramethyl-anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：486。Ultimate analysis (C 38H 30): theoretical value C:93.83%, H:6.17%; Measured value C:93.88%, H:6.12%.
Embodiment 41, and 4,6,7-tetramethyl--9,10-two (2-methyl isophthalic acid-naphthyl) anthracene (compounds X III-4):
With 2-methyl isophthalic acid-naphthalene bromide and 1,4,6,7-tetramethyl-anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：515。Ultimate analysis (C 40H 34): theoretical value C:93.39%, H:6.61%; Measured value C:93.52%, H:6.48%.
Embodiment 42, and 3,6,7-tetramethyl--9,10-two (1-naphthyl) anthracene (compounds X IV-2):
With 1-naphthalene bromide and 2,3,6,7-tetramethyl-anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：486。Ultimate analysis (C 38H 30): theoretical value C:93.83%, H:6.17%; Measured value C:93.75%, H:6.25%.
Embodiment 43, and 3,6,7-tetramethyl--9,10-two (2-methyl isophthalic acid-naphthyl) anthracene (compounds X IV-4):
With 2-methyl isophthalic acid-naphthalene bromide and 2,3,6,7-tetramethyl-anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：515。Ultimate analysis (C 40H 34): theoretical value C:93.39%, H:6.61%; Measured value C:93.68%, H:6.32%.
Embodiment 44, and 2,3,4,5,6,7,8-prestox-9,10-diphenylanthrancene (compounds X V-1)
With bromobenzene and 1,2,3,4,5,6,7,8-prestox anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：442。Ultimate analysis (C 34H 34): theoretical value C:92.31%, H:7.69%; Measured value C:92.55%, H:7.45%.
Embodiment 45, and 2,3,4,5,6,7,8-prestox-9,10-two (1-naphthyl) anthracene (compounds X V-2)
With 1-naphthalene bromide and 1,2,3,4,5,6,7,8-prestox anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：542。Ultimate analysis (C 42H 38): theoretical value C:92.99%, H:7.01%; Measured value C:92.85%, H:7.15%.
Embodiment 46, and 2,3,4,5,6,7,8-prestox-9,10-two (2-naphthyl) anthracene (compounds X V-3)
With 2-naphthalene bromide and 1,2,3,4,5,6,7,8-prestox anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：542。Ultimate analysis (C 42H 38): theoretical value C:92.99%, H:7.01%; Measured value C:92.90%, H:7.10%.
Embodiment 47, and 2,3,4,5,6,7,8-prestox-9,10-two (2-methyl isophthalic acid-naphthyl) anthracene (compounds X V-4)
With 2-methyl isophthalic acid-naphthalene bromide and 1,2,3,4,5,6,7,8-prestox anthraquinone is the synthetic method preparation of starting raw material by Compound I-1 among the embodiment one, uses silica gel chromatography at last.
MS(m/z)：570。Ultimate analysis (C 44H 42): theoretical value C:92.63%, H:7.37%; Measured value C:92.74%, H:7.26%.
Electroluminescent device embodiment
Device embodiment one
Deposition one deck is as the Indium sesquioxide tin protoxide (ITO) of transparent anode on a glass substrate, the hole mobile material that then prepares one deck 50 nanometer thickness: N by the method for vacuum-evaporation, N '-phenylbenzene-N, N '-two (1-naphthyl)-1,1 '-biphenyl-4,4 '-diamines (NPB), on this hole transmission layer, continue then by the material among the present invention of vacuum evaporation coating last layer 50 nanometer thickness, 2,3-dimethyl-9,10-two (2-methyl isophthalic acid-naphthyl) anthracene (Compound I-4) continues the hole mobile material oxine aluminium (AlQ by vacuum evaporation coating last layer 10 nanometer thickness again on this luminescent layer 3), at last again the alloy of vacuum evaporation one deck Mg: Ag (10: 1) as the negative electrode of device, about 200 nanometers.Galvanic positive pole is added on the ITO layer, negative pole is added on Mg: the Ag alloy layer, can launch bright uniform blue light from the ITO layer, CIE coordinate (0.16,0.13) opens bright voltage V, and when voltage was 20V, high-high brightness was at 1200cd/m 2About, radiative main peak is about 444nm.
Device embodiment two
Deposition one deck is as the Indium sesquioxide-stannic oxide (ITO) of transparent anode on a glass substrate, the hole mobile material that then prepares one deck 50 nanometer thickness: N by the method for vacuum-evaporation, N '-phenylbenzene-N, N '-two (1-naphthyl)-1,1 '-biphenyl-4,4 '-diamines (NPB), on this hole transmission layer, continue then by the material among the present invention of vacuum evaporation coating last layer 50 nanometer thickness, 2,3-dimethyl-9,10-two (2-methyl isophthalic acid-naphthyl) anthracene (Compound I-4), at last again the alloy of vacuum evaporation one deck Mg: Ag (10: 1) as the negative electrode of device, about 200 nanometers.Galvanic positive pole is added on the ITO layer, negative pole is added on Mg: the Ag alloy layer, can launch bright uniform blue light from the ITO layer, CIE coordinate (0.17,0.11) opens bright voltage V, and when voltage was V, high-high brightness was at 450cd/m 2About, radiative main peak is about 436nm.
Although describe the present invention in conjunction with the preferred embodiments, but the present invention is not limited to the foregoing description, be to be understood that, claims have been summarized scope of the present invention, under the guiding of the present invention's design, it should be appreciated by one skilled in the art that the certain change to the various embodiments of the present invention scheme is carried out all will be covered by the spirit and scope of claims of the present invention.

Claims (49)

1. electroluminescent organic material, this material is the derivative of anthracene, it is characterized in that this luminescent material has following structure:
In the said structure formula, substituent R 1-R 10Can be a kind of in hydrogen atom, alkyl, iso-alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, trifluoromethyl, aromatic base or the heterocyclic substituent (furans, thiophene, pyrroles, pyridine, pyrans, quinoline, indoles, carbazole).
2. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3Be methyl, R 9, R 10Be phenyl, R 1, R 4-R 8Be hydrogen atom, this luminescent material has following structure:
3. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3Be methyl, R 9, R 10Be 1-naphthyl, R 1, R 4-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100023
4. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3Be methyl, R 9, R 10Be 1-naphthyl, R 1, R 4-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100024
5. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3Be methyl, R 9, R 10Be 2-methyl isophthalic acid-naphthyl, R 1, R 4-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100031
6. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3Be methyl, R 9, R 10Be 3,5-phenylbenzene phenyl, R 1, R 4-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100032
7. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3Be methyl, R 9, R 10Be 3,5-two (o-tolyl) phenyl, R 1, R 4-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100033
8. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3Be methyl, R 9, R 10Be 3,5-two (tolyl) phenyl, R 1, R 4-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100034
9. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3Be methyl, R 9, R 10Be 3,5-two (p-methylphenyl) phenyl, R 1, R 4-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100041
10. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3Be methyl, R 9, R 10Be 3,5-two (1-naphthyl) phenyl, R 1, R 4-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100042
11. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3Be methyl, R 9, R 10Be 3,5-two (2-naphthyl) phenyl, R 1, R 4-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100043
12. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3Be methyl, R 9, R 10Be 3,5-two (2-methyl isophthalic acid-naphthyl) phenyl, R 1, R 4-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100044
13. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3Be methyl, R 9, R 10Be 3,5-difluorophenyl, R 1, R 4-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100045
14. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3Be methyl, R 9, R 10Be 4-trifluoromethyl-phenyl, R 1, R 4-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100051
15. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3Be methyl, R 9, R 10Be 1-naphthyl, R 2, R 3, R 5-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100052
16. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3Be methyl, R 9, R 10Be 2-methyl isophthalic acid-naphthyl, R 2, R 3, R 5-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100053
17. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 4, R 9, R 10Be phenyl, R 2, R 3, R 5-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100054
18. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 4Be phenyl, R 9, R 10Be 1-naphthyl, R 2, R 3, R 5-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100055
19. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 4Be phenyl, R 9, R 10Be 2-methyl isophthalic acid-naphthyl, R 2, R 3, R 5-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100061
20. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 3Be methyl, R 9, R 10Be 1-naphthyl, R 2, R 4, R 5-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100062
21. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 3Be methyl, R 9, R 10Be 2-methyl isophthalic acid-naphthyl, R 2, R 4, R 5-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100063
22. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 2Be methyl, R 9, R 10Be 1-naphthyl, R 3-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100064
23. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 2Be methyl, R 9, R 10Be 2-methyl isophthalic acid-naphthyl, R 3-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100065
24. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 2, R 3, R 4Be methyl, R 9, R 10Be 1-naphthyl, R 5-R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100071
25. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 2, R 3, R 4Be methyl, R 9, R 10Be 2-methyl isophthalic acid-naphthyl, R 5-R 9Be hydrogen atom, this luminescent material has following structure:
26. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 2, R 3, R 4Be phenyl, R 5-R 10Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100073
27. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 2, R 5, R 6Be methyl, R 9, R 10Be 1-naphthyl, R 3, R 4, R 7, R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100074
28. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 2, R 5, R 6Be methyl, R 9, R 10Be 2-methyl isophthalic acid-naphthyl, R 3, R 4, R 7, R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100075
29. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 3, R 5, R 7Be methyl, R 9, R 10Be 1-naphthyl, R 2, R 4, R 6, R 8Be hydrogen atom, this luminescent material has following structure:
30. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 3, R 5, R 7Be methyl, R 9, R 10Be 2-methyl isophthalic acid-naphthyl, R 2, R 4, R 6, R 8Be hydrogen atom, this luminescent material has following structure:
31. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 3, R 5, R 7Be phenyl, R 2, R 4, R 6, R 8, R 9, R 10Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100083
32. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 3, R 6, R 7Be methyl, R 9, R 10Be 1-naphthyl, R 2, R 4, R 5, R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100084
33. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 3, R 6, R 7Be methyl, R 9, R 10Be 2-methyl isophthalic acid-naphthyl, R 2, R 4, R 5, R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100091
34. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 3, R 6, R 8Be methyl, R 9, R 10Be 1-naphthyl, R 2, R 4, R 5, R 7Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100092
35. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 3, R 6, R 8Be methyl, R 9, R 10Be 2-methyl isophthalic acid-naphthyl, R 2, R 4, R 5, R 7Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100093
36. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 3, R 6, R 8Be phenyl, R 2, R 4, R 5, R 7, R 9, R 10Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100094
37. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 4, R 5, R 8Be methyl, R 9, R 10Be 1-naphthyl, R 2, R 3, R 6, R 7Be hydrogen atom, this luminescent material has following structure:
38. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 4, R 5, R 8Be methyl, R 9, R 10Be 2-methyl isophthalic acid-naphthyl, R 2, R 3, R 6, R 7Be hydrogen atom, this luminescent material has following structure:
39 a kind of electroluminescent organic materials according to claim 1 is characterized in that wherein said R 1, R 4, R 5, R 8Be phenyl, R 2, R 3, R 6, R 7, R 9, R 10Be hydrogen atom, this luminescent material has following structure:
40. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 4, R 5, R 8Be phenyl, R 9, R 10Be methyl, R 2, R 3, R 6, R 7Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100103
41. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 4, R 6, R 7Be methyl, R 9, R 10Be 1-naphthyl, R 2, R 3, R 5, R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100104
42. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 4, R 6, R 7Be methyl, R 9, R 10Be 2-methyl isophthalic acid-naphthyl, R 2, R 3, R 5, R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100111
43. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3, R 6, R 7Be methyl, R 9, R 10Be 1-naphthyl, R 1, R 4, R 5, R 8Be hydrogen atom, this luminescent material has following structure:
Figure A0210037100112
44. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 2, R 3, R 6, R 7Be methyl, R 9, R 10Be 2-methyl isophthalic acid-naphthyl, R 1, R 4, R 5, R 8Be hydrogen atom, this luminescent material has following structure:
45. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8Be methyl, R 9, R 10Be phenyl, this luminescent material has following structure:
46. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8Be methyl, R 9, R 10Be the 1-naphthyl, this luminescent material has following structure:
47. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8Be methyl, R 9, R 10Be the 2-naphthyl, this luminescent material has following structure:
48. a kind of electroluminescent organic material according to claim 1 is characterized in that, wherein said R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8Be methyl, R 9, R 10Be 2-methyl isophthalic acid-naphthyl, this luminescent material has following structure:
49. a kind of electroluminescent organic material according to claim 1 is characterized in that, this class material can be used on carrier blocking layers or the luminescent layer in the organic electroluminescence device of being made up of the multilayer organic materials.
CN 02100371 2002-01-15 2002-01-15 Organic electroluminescent material Expired - Fee Related CN1239447C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN 02100371 CN1239447C (en) 2002-01-15 2002-01-15 Organic electroluminescent material

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN 02100371 CN1239447C (en) 2002-01-15 2002-01-15 Organic electroluminescent material

Publications (2)

Publication Number Publication Date
CN1362464A true CN1362464A (en) 2002-08-07
CN1239447C CN1239447C (en) 2006-02-01

Family

ID=4739334

Family Applications (1)

Application Number Title Priority Date Filing Date
CN 02100371 Expired - Fee Related CN1239447C (en) 2002-01-15 2002-01-15 Organic electroluminescent material

Country Status (1)

Country Link
CN (1) CN1239447C (en)

Cited By (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006206503A (en) * 2005-01-28 2006-08-10 Tokyo Institute Of Technology PI electron compound and n-type organic field effect transistor using the same
CN100335462C (en) * 2003-09-05 2007-09-05 清华大学 Carbazole derivative and its application in electroluminescent device
CN100335591C (en) * 2005-12-07 2007-09-05 清华大学 Organic electroluminescence liquid crystal compound, and its preparing method and use
WO2007110129A1 (en) 2006-03-24 2007-10-04 Merck Patent Gmbh New materials for organic electroluminescent devices
CN100361980C (en) * 2005-12-29 2008-01-16 中国科学院上海有机化学研究所 A New Blue Light Material--Anthracene Derivatives Containing Triazine Ring
CN100425599C (en) * 2005-12-31 2008-10-15 清华大学 Organic electroluminescent material and its application
DE102007024850A1 (en) 2007-05-29 2008-12-04 Merck Patent Gmbh New materials for organic electroluminescent devices
DE102008008953A1 (en) 2008-02-13 2009-08-20 Merck Patent Gmbh New materials for organic electroluminescent devices
CN100572495C (en) * 2002-03-09 2009-12-23 Cdt牛津有限公司 Polymerisable compound and the organic luminescent device that contains it
WO2010083869A2 (en) 2009-01-23 2010-07-29 Merck Patent Gmbh Materials for organic electroluminescence devices
CN1914293B (en) * 2003-12-19 2010-12-01 出光兴产株式会社 Luminescent material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device
DE102009034625A1 (en) 2009-07-27 2011-02-03 Merck Patent Gmbh New materials for organic electroluminescent devices
DE102009051172A1 (en) 2009-10-29 2011-05-05 Merck Patent Gmbh Materials for electronic devices
WO2011054442A2 (en) 2009-11-06 2011-05-12 Merck Patent Gmbh Materials for electronic devices
DE102009052428A1 (en) 2009-11-10 2011-05-12 Merck Patent Gmbh Connection for electronic devices
WO2011088877A1 (en) 2010-01-25 2011-07-28 Merck Patent Gmbh Compounds for electronic devices
CN102163697A (en) * 2005-07-25 2011-08-24 株式会社半导体能源研究所 Light-emitting element, light-emitting device, and electronic appliance
WO2012045384A1 (en) 2010-10-09 2012-04-12 Merck Patent Gmbh Materials for electronic devices
DE102010054316A1 (en) 2010-12-13 2012-06-14 Merck Patent Gmbh Substituted tetraarylbenzenes
DE102011011104A1 (en) 2011-02-12 2012-08-16 Merck Patent Gmbh Substituted dibenzonaphthacenes
CN102652462A (en) * 2009-12-15 2012-08-29 三菱化学株式会社 Method for manufacturing organic electroluminescent element, organic electroluminescent element, display device and illuminating device
CN102898271A (en) * 2012-05-25 2013-01-30 杭州师范大学 Synthesis method and use of polycyclic aromatic hydrocarbon and its derivatives
CN101891673B (en) * 2009-11-13 2013-03-20 昆山维信诺显示技术有限公司 Organic material and application thereof in organic electroluminescence devices
US8405070B2 (en) 2005-03-23 2013-03-26 Semiconductor Energy Laboratory Co., Ltd. Composite material, and light emitting element and light emitting device using the composite material
US20130240869A1 (en) * 2010-12-17 2013-09-19 Kerwin D. Dobbs Anthracene derivative compounds for electronic applications
US8795847B2 (en) 2005-12-08 2014-08-05 Merck Patent Gmbh Materials for organic electroluminescent devices
US8836337B2 (en) 2009-06-05 2014-09-16 Beijing Visionox Technology Co., Ltd. Organic electroluminescence device and testing method thereof
CN102007194B (en) * 2008-04-14 2015-01-14 默克专利有限公司 Novel materials for organic electroluminescence devices
US8940407B2 (en) * 2004-11-06 2015-01-27 Merck Patent Gmbh Organic electroluminescent device
WO2015165563A1 (en) 2014-04-30 2015-11-05 Merck Patent Gmbh Materials for electronic devices
CN105102408A (en) * 2013-03-26 2015-11-25 株式会社东进世美肯 Novel triphenylene derivative compound and organic light-emitting element using same
WO2015192941A1 (en) 2014-06-18 2015-12-23 Merck Patent Gmbh Compositions for electronic devices
US9412951B2 (en) 2009-11-13 2016-08-09 Beijing Visionox Technology Co., Ltd. Organic materials and organic electroluminescent apparatuses using the same
US9466800B2 (en) 2009-04-24 2016-10-11 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element comprising the same
US9512137B2 (en) 2010-08-05 2016-12-06 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
US9660195B2 (en) 2008-03-19 2017-05-23 Idemitsu Kosan Co., Ltd. Anthracene derivative having a phenanthryl group
EP3211058A1 (en) 2005-08-26 2017-08-30 Merck Patent GmbH New materials for organic electroluminescent devices
WO2018189134A1 (en) 2017-04-13 2018-10-18 Merck Patent Gmbh Composition for organic electronic devices
CN109279999A (en) * 2017-07-21 2019-01-29 三星显示有限公司 Condensed ring compound and organic light-emitting device including the condensed ring compound
EP3647393A1 (en) 2013-07-30 2020-05-06 Merck Patent GmbH Materials for electronic devices
EP3712229A1 (en) 2013-07-30 2020-09-23 Merck Patent GmbH Materials for electronic devices
CN112552137A (en) * 2020-12-09 2021-03-26 黑龙江省科学院石油化学研究院 Organic electroluminescent intermediate material and synthetic method thereof
WO2022173022A1 (en) * 2021-02-15 2022-08-18 保土谷化学工業株式会社 Compound and organic electroluminescent element using said compound

Cited By (74)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100572495C (en) * 2002-03-09 2009-12-23 Cdt牛津有限公司 Polymerisable compound and the organic luminescent device that contains it
CN100335462C (en) * 2003-09-05 2007-09-05 清华大学 Carbazole derivative and its application in electroluminescent device
US10069074B2 (en) 2003-12-19 2018-09-04 Idemitsu Kosan Co., Ltd. Light-emitting material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device
CN1914293B (en) * 2003-12-19 2010-12-01 出光兴产株式会社 Luminescent material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device
US9219234B2 (en) 2003-12-19 2015-12-22 Idemitsu Kosan Co., Ltd. Light-emitting material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device
US9786846B2 (en) 2003-12-19 2017-10-10 Idemitsu Kosan Co., Ltd. Light-emitting material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device
US10205101B2 (en) 2003-12-19 2019-02-12 Idemitsu Kosan Co., Ltd. Light-emitting material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device
US8853675B2 (en) 2003-12-19 2014-10-07 Idemitsu Kosan Co., Ltd. Light-emitting material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device
CN101980395B (en) * 2003-12-19 2014-05-07 出光兴产株式会社 Organic electroluminescent device
US8940407B2 (en) * 2004-11-06 2015-01-27 Merck Patent Gmbh Organic electroluminescent device
JP2006206503A (en) * 2005-01-28 2006-08-10 Tokyo Institute Of Technology PI electron compound and n-type organic field effect transistor using the same
US8405070B2 (en) 2005-03-23 2013-03-26 Semiconductor Energy Laboratory Co., Ltd. Composite material, and light emitting element and light emitting device using the composite material
US9224968B2 (en) 2005-07-25 2015-12-29 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, and electronic appliance
CN102163697A (en) * 2005-07-25 2011-08-24 株式会社半导体能源研究所 Light-emitting element, light-emitting device, and electronic appliance
EP3211058A1 (en) 2005-08-26 2017-08-30 Merck Patent GmbH New materials for organic electroluminescent devices
CN100335591C (en) * 2005-12-07 2007-09-05 清华大学 Organic electroluminescence liquid crystal compound, and its preparing method and use
US8795847B2 (en) 2005-12-08 2014-08-05 Merck Patent Gmbh Materials for organic electroluminescent devices
CN100361980C (en) * 2005-12-29 2008-01-16 中国科学院上海有机化学研究所 A New Blue Light Material--Anthracene Derivatives Containing Triazine Ring
CN100425599C (en) * 2005-12-31 2008-10-15 清华大学 Organic electroluminescent material and its application
WO2007110129A1 (en) 2006-03-24 2007-10-04 Merck Patent Gmbh New materials for organic electroluminescent devices
US8999521B2 (en) 2006-03-24 2015-04-07 Merck Patent Gmbh Materials for organic electroluminescent devices
DE102007024850A1 (en) 2007-05-29 2008-12-04 Merck Patent Gmbh New materials for organic electroluminescent devices
DE102008008953A1 (en) 2008-02-13 2009-08-20 Merck Patent Gmbh New materials for organic electroluminescent devices
DE102008008953B4 (en) 2008-02-13 2019-05-09 Merck Patent Gmbh New materials for organic electroluminescent devices
US8993123B2 (en) 2008-02-13 2015-03-31 Merck Patent Gmbh Materials for organic electroluminescent devices
US9660195B2 (en) 2008-03-19 2017-05-23 Idemitsu Kosan Co., Ltd. Anthracene derivative having a phenanthryl group
US11456421B2 (en) 2008-03-19 2022-09-27 Idemitsu Kosan Co., Ltd. Anthracene derivatives, luminescent materials and organic electroluminescent devices
US10461257B2 (en) 2008-03-19 2019-10-29 Idemitsu Kosan Co., Ltd. Anthracene derivatives, luminescent materials and organic electroluminescent devices
CN102007194B (en) * 2008-04-14 2015-01-14 默克专利有限公司 Novel materials for organic electroluminescence devices
DE102009005746A1 (en) 2009-01-23 2010-07-29 Merck Patent Gmbh Materials for organic electroluminescent devices
US9006503B2 (en) 2009-01-23 2015-04-14 Merck Patent Gmbh Organic electroluminescence devices containing substituted benzo[C]phenanthrenes
US8710284B2 (en) 2009-01-23 2014-04-29 Merck Patent Gmbh Materials for organic electroluminescent devices containing substituted 10-benzo[c]phenanthrenes
WO2010083869A2 (en) 2009-01-23 2010-07-29 Merck Patent Gmbh Materials for organic electroluminescence devices
US9741938B2 (en) 2009-04-24 2017-08-22 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element comprising the same
US9466800B2 (en) 2009-04-24 2016-10-11 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element comprising the same
US10263191B2 (en) 2009-04-24 2019-04-16 Idemitsu Kosan Co., Ltd. Aromatic amine derivative, and organic electroluminescent element comprising the same
US8836337B2 (en) 2009-06-05 2014-09-16 Beijing Visionox Technology Co., Ltd. Organic electroluminescence device and testing method thereof
WO2011012212A1 (en) 2009-07-27 2011-02-03 Merck Patent Gmbh Novel materials for organic electroluminescent devices
DE102009034625A1 (en) 2009-07-27 2011-02-03 Merck Patent Gmbh New materials for organic electroluminescent devices
DE102009051172A1 (en) 2009-10-29 2011-05-05 Merck Patent Gmbh Materials for electronic devices
WO2011050888A1 (en) 2009-10-29 2011-05-05 Merck Patent Gmbh Materials for electronic devices
WO2011054442A2 (en) 2009-11-06 2011-05-12 Merck Patent Gmbh Materials for electronic devices
DE102009053191A1 (en) 2009-11-06 2011-05-12 Merck Patent Gmbh Materials for electronic devices
DE102009052428A1 (en) 2009-11-10 2011-05-12 Merck Patent Gmbh Connection for electronic devices
WO2011057701A1 (en) 2009-11-10 2011-05-19 Merck Patent Gmbh Organic compounds for electroluminescent devices
CN101891673B (en) * 2009-11-13 2013-03-20 昆山维信诺显示技术有限公司 Organic material and application thereof in organic electroluminescence devices
US9412951B2 (en) 2009-11-13 2016-08-09 Beijing Visionox Technology Co., Ltd. Organic materials and organic electroluminescent apparatuses using the same
CN102652462B (en) * 2009-12-15 2016-01-20 三菱化学株式会社 The manufacture method of organic electroluminescence device, organic electroluminescence device, display unit and lighting device
CN102652462A (en) * 2009-12-15 2012-08-29 三菱化学株式会社 Method for manufacturing organic electroluminescent element, organic electroluminescent element, display device and illuminating device
WO2011088877A1 (en) 2010-01-25 2011-07-28 Merck Patent Gmbh Compounds for electronic devices
DE102010005697A1 (en) 2010-01-25 2011-07-28 Merck Patent GmbH, 64293 Connections for electronic devices
US9512137B2 (en) 2010-08-05 2016-12-06 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
WO2012045384A1 (en) 2010-10-09 2012-04-12 Merck Patent Gmbh Materials for electronic devices
DE102010048074A1 (en) 2010-10-09 2012-04-12 Merck Patent Gmbh Materials for electronic devices
DE102010054316A1 (en) 2010-12-13 2012-06-14 Merck Patent Gmbh Substituted tetraarylbenzenes
WO2012079678A1 (en) 2010-12-13 2012-06-21 Merck Patent Gmbh Substituted tetraarylbenzenes
US20130240869A1 (en) * 2010-12-17 2013-09-19 Kerwin D. Dobbs Anthracene derivative compounds for electronic applications
WO2012107163A1 (en) 2011-02-12 2012-08-16 Merck Patent Gmbh Substituted dibenzonaphthacene
DE102011011104A1 (en) 2011-02-12 2012-08-16 Merck Patent Gmbh Substituted dibenzonaphthacenes
CN102898271A (en) * 2012-05-25 2013-01-30 杭州师范大学 Synthesis method and use of polycyclic aromatic hydrocarbon and its derivatives
CN105102408A (en) * 2013-03-26 2015-11-25 株式会社东进世美肯 Novel triphenylene derivative compound and organic light-emitting element using same
CN105102408B (en) * 2013-03-26 2018-07-10 株式会社东进世美肯 Novel triphenylene derivative compound and organic light-emitting element using same
EP3647393A1 (en) 2013-07-30 2020-05-06 Merck Patent GmbH Materials for electronic devices
EP3712229A1 (en) 2013-07-30 2020-09-23 Merck Patent GmbH Materials for electronic devices
WO2015165563A1 (en) 2014-04-30 2015-11-05 Merck Patent Gmbh Materials for electronic devices
EP3533794A2 (en) 2014-04-30 2019-09-04 Merck Patent GmbH Materials for electronic devices
WO2015192941A1 (en) 2014-06-18 2015-12-23 Merck Patent Gmbh Compositions for electronic devices
DE102014008722A1 (en) 2014-06-18 2015-12-24 Merck Patent Gmbh Compositions for electronic devices
DE102014008722B4 (en) 2014-06-18 2024-08-22 Merck Patent Gmbh Compositions for electronic devices, formulation containing them, use of the composition, use of the formulation and organic electronic device containing the composition
WO2018189134A1 (en) 2017-04-13 2018-10-18 Merck Patent Gmbh Composition for organic electronic devices
US11778907B2 (en) 2017-04-13 2023-10-03 Merck Patent Gmbh Composition for organic electronic devices
CN109279999A (en) * 2017-07-21 2019-01-29 三星显示有限公司 Condensed ring compound and organic light-emitting device including the condensed ring compound
CN112552137A (en) * 2020-12-09 2021-03-26 黑龙江省科学院石油化学研究院 Organic electroluminescent intermediate material and synthetic method thereof
WO2022173022A1 (en) * 2021-02-15 2022-08-18 保土谷化学工業株式会社 Compound and organic electroluminescent element using said compound

Also Published As

Publication number Publication date
CN1239447C (en) 2006-02-01

Similar Documents

Publication Publication Date Title
CN1362464A (en) Organic electroluminescent material
CN1255365C (en) Fluorene compound and organic lumnescent device using the same
CN1291969C (en) Oligofluorenylene compounds
CN1918946A (en) organic electroluminescent element
CN1157461C (en) Double spiro derivatives and their applications as electroluminescent materials
CN1861618A (en) Organic metal compounds, organic electroluminesence display devices using the compounds and method for preparation of the devices
CN1365347A (en) Anthracene derivative and electroluminescent device using the same
CN1625552A (en) New material for transporting electrons and organic electroluminescent display using the same
CN1898355A (en) Anthracene derivatives and organic light emitting device using the same as a light emitting material
CN1881649A (en) Organic electroluminescence device and manufacturing method thereof
CN101035878A (en) New compound and organic light emitting device using the same(10)
CN1168132A (en) organic electroluminescent device, organic thin film and triamine compound
CN101074245A (en) Phosphorescent heteronuclear copper(I)-iridium(III) complex and organic electroluminescence device using the same
CN1527871A (en) Light-emitting device and aromatic compound
CN1911898A (en) Triarylamine-based compound, method of preparing the same, and organic light emitting device using the triarylamine-based compound
CN1807396A (en) Anthracene derivative, organic electroluminescent device, and display device
CN1760324A (en) Cyclometalated transition metal complex and organic electroluminescent display device using the same
CN1394835A (en) Perylene derivative synthesis method, perylene derivative and organic EL element
CN1902295A (en) Polymeric, phosphorescent, organically semi-conductive emitter materials based on perarylated boranes, method for their production and use thereof
CN1637000A (en) Imidazole ring-containing compound and organic electroluminescence display device
CN1840525A (en) A kind of organic electroluminescent material and its application
CN1219778C (en) Quinacridone derivant and application in organic electroluminescent device thereof
CN1861740A (en) Red light emitting fluorescent dye and its synthesis and use
CN1246417C (en) Electroluminescent organic material and its application
CN1900092A (en) Organic electroluminescence material and its use

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
CF01 Termination of patent right due to non-payment of annual fee
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20060201

Termination date: 20180115