CN104650090B - A kind of fluorene kind derivative of the bases of -3- containing carbazole group and its application - Google Patents
A kind of fluorene kind derivative of the bases of -3- containing carbazole group and its application Download PDFInfo
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- GQDFUQVMWTWXIF-UHFFFAOYSA-N CC(C)(c1c2)c(cc(cc3)-c(cc4)cc(c5c6cccc5)c4[n]6-c4ccccc4)c3-c1cc(C(C)(C)c1c3)c2-c1ccc3-c1nc2ncc[n]2c(SC)c1 Chemical compound CC(C)(c1c2)c(cc(cc3)-c(cc4)cc(c5c6cccc5)c4[n]6-c4ccccc4)c3-c1cc(C(C)(C)c1c3)c2-c1ccc3-c1nc2ncc[n]2c(SC)c1 GQDFUQVMWTWXIF-UHFFFAOYSA-N 0.000 description 1
- LGVVHSHVTSQNIY-UHFFFAOYSA-N CC(C)(c1c2)c(cc(cc3)-c(cc4c5cc(-c6ccccc6)ccc55)ccc4[n]5-c4ccccc4)c3-c1ccc2-c(cc1)ccc1-c(cn1)c[n]2c1ncc2-c1ccccc1 Chemical compound CC(C)(c1c2)c(cc(cc3)-c(cc4c5cc(-c6ccccc6)ccc55)ccc4[n]5-c4ccccc4)c3-c1ccc2-c(cc1)ccc1-c(cn1)c[n]2c1ncc2-c1ccccc1 LGVVHSHVTSQNIY-UHFFFAOYSA-N 0.000 description 1
- NYRFFXGYEFFYAL-UHFFFAOYSA-N CC1(C)c2cc(-c3cnc4nc(C(F)(F)F)cc[n]34)ccc2-c(cc2C3(C)C)c1cc2-c(cc1)c3cc1-c(cc1)cc(c2c3cccc2)c1[n]3-c1ccccc1 Chemical compound CC1(C)c2cc(-c3cnc4nc(C(F)(F)F)cc[n]34)ccc2-c(cc2C3(C)C)c1cc2-c(cc1)c3cc1-c(cc1)cc(c2c3cccc2)c1[n]3-c1ccccc1 NYRFFXGYEFFYAL-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention provides one kind to have such as formula（1）、（2）Or（3）The fluorene kind derivative of the new 3 base group containing carbazole shown in structure：Wherein：One of A and B are N, and another H in CH groups or CH groups is by the alkyl of C1 12, the aryl of C6 30, the heterocyclic aryl of C6 30, CF3、‑SCH3In a kind of substituted group；Ar is selected from fluorenylidene or sub- indeno fluorenyl；R1And R2Separately selected from H, the aliphatic alkyl of substituted or unsubstituted C1 12, the aliphatic cycloalkyl of C1 12, the aryl of C6 30, methyl mercapto, methoxyl group, ethyoxyl or trifluoromethyl；R3And R4The aliphatic cycloalkyl of aliphatic alkyl, C1 12 or the aryl of C6 30 selected from substituted or unsubstituted C1 12；R4 can also select H.Such compound property is stablized, and preparation process is simple, and phosphorescent light body material can be used as in organic electroluminescence device, obtains higher luminous efficiency and relatively low opens bright voltage.
Description
Technical field
The present invention relates to a kind of novel organic compound and its applications in ORGANIC ELECTROLUMINESCENCE DISPLAYS technical field.
Background technology
Electroluminescent material and device have had reached practical level by years of researches and development, a variety of materials,
Such as hole material, electronic material, luminescent material, display device technology of preparing have been achieved for considerable progress.With research
Going deep into for work is increasingly obvious with the practical requirement to material, the advantage by the use of phosphorescence as luminescent material in the process.Phosphorescence material
The luminous efficiency of material is higher than 3 to 4 times of fluorescent material, for many display products for requiring brightness higher, is with phosphor material
Primary selection.Phosphorescence luminescent layer in device is steamed altogether by two class materials to be formed, and one kind is material of main part, accounts for the 90% of common steaming component
Left and right, another kind of is phosphorescent coloring, accounts for 10% or so of common steaming component.What tradition used is 4 in phosphorescent light body material, 4 '-N,
- two carbazole biphenyls of N '.The material has higher triplet, can be well matched with phosphorescent coloring, but due to the material point
Son amount is smaller（Molecular weight 484）So that glass transition temperature is relatively low（Tg about 1100C or once）, process is being used easily to crystallize, shape
Into island, cause not bright spot, device lifetime shortens.The R and D of new phosphorescent light body material are operated in continuous progress,
In have pyrimidine（Pyrazine）Base is introduced into the research patent in material structure（Application number 200680047266.5, publication number
CN101331626A）, also have research patent pyrimidine radicals being introduced into material structure（Application number 200580014777.2, it is open
Number CN1951155A）, preferable improvement effect is all obtained in various degree.
Therefore, the phosphorescent light body material based on existing research, further exploitation stability and high efficiency, so as to reduce bright electricity
Pressure improves device efficiency, has critically important actual application value.
The content of the invention
The purpose of the present invention is to propose to a kind of new organic compound, such compound can be used for organic electroluminescent
Display field particularly, is used as phosphorescent light body material, and then obtains in the organic luminescence function layer in organic electroluminescence device
Organic electroluminescence device low to driving voltage, that current efficiency is high, half-life period is longer.
In order to solve the above technical problems, the technical solution adopted in the present invention is as follows：
Organic compound provided by the invention, i.e., the phosphorescence master containing imidazo ［ 1,2-a ］ pyrimidine group and carbazole group
Body material or the phosphorescent light body material containing imidazo ［ 1,2-a ］ pyrazine group and carbazole group have higher molecular weight,
Be conducive to the raising of compound glass transition temperature, meanwhile, imidazo [1,2, a] pyridine groups or imidazo ［ 1,2-a ］ pyrazinyl
Group and carbazole group can be directly connected to form compound, can also pass through the fused ring aryls groups such as fluorenylidene, Ya Yin And fluorenyls
It is connected, each group in the compound is in on-plane surface state so that entire molecule is formed to a certain degree on space multistory
On distortion, the stereoeffect of molecule is irregular, advantageously forms unformed film, is particularly having existing for carbazole group
On the basis of, present invention introduces imidazo ［ 1,2-a ］ pyrimidine group or imidazo ［ 1,2-a ］ pyrazine groups, effectively have adjusted material
The triplet of material（T1）.When the material of the present invention is used for electroluminescent device as phosphorescence host, electroluminescent hair
Light improves significantly opening the everyways such as bright voltage, brightness, service life.
The present invention provides one kind to have such as formula（1）、（2）Or（3）The fluorenes class of the base groups of -3- containing carbazole of shown structure is spread out
Biology：
Wherein：
One of A and B be N, it is another be the H in CH groups or CH groups be 1-12 by carbon number alkyl, carbon original
The heterocyclic aryl ,-CF that aryl that subnumber is 6-30, carbon number are 6-303、-SCH3In a kind of substituted group；
Ar is selected from fluorenylidene or sub- indeno fluorenyl；
R1And R2Separately selected from H, substituted or unsubstituted aliphatic alkyl, the carbon atom that carbon number is 1-12
Substituted or unsubstituted aryl that substituted or unsubstituted aliphatic cycloalkyl that number is 1-12, carbon number are 6-30, first sulphur
Base, methoxyl group, ethyoxyl or trifluoromethyl；
R3Selected from carbon number be 1-12 substituted or unsubstituted aliphatic alkyl, carbon number be 1-12 substitution or
Unsubstituted aliphatic cycloalkyl or the substituted or unsubstituted aryl that carbon number is 6-30；
R4Selected from H, carbon number be 1-12 substituted or unsubstituted aliphatic alkyl, carbon number be 1-12 substitution
Or the substituted or unsubstituted aryl that unsubstituted aliphatic cycloalkyl or carbon number are 6-30；
L1And L2It is respectively and independently selected from singly-bound, the substitution that the alkylidene that carbon number is 1-20, carbon number are 6-30 or not
Substituted arlydene or the substituted or unsubstituted heteroarylidene that carbon number is 6-30.
Further, general formula（4）Shown structure can directly and imidazo ［ 1,2-a ］ pyrimidine group or imidazo ［ 1,2-a ］
Pyrazine group connects, alternatively, working as R1Or R2For H when, general formula（4）Shown structure passes through R1Or R2With imidazo ［ 1,2-a ］ pyrimidine radicals
Group or imidazo ［ 1,2-a ］ pyrazine group are connected and just succeed in reaching an agreement formula（4）Shown structure is connected directly between R1Or R2Position on；
Further, the R1And R2Separately selected from H, methyl, ethyl, propyl, normal-butyl, n-pentyl, just oneself
Base, phenyl, tolyl, ethylbenzene, xenyl,（Carbazole -9- bases）Phenyl, naphthalene, carbazyl, N- phenyl carbazoles base, fluorenyl, N-
Fluorenyl carbazyl, methyl mercapto, methoxyl group, ethyoxyl, trifluoromethyl, dibenzothiophene or dibenzofuran group.
Further, the R3Selected from methyl, ethyl, propyl, normal-butyl, n-pentyl, n-hexyl, phenyl, tolyl, second
Phenyl, xenyl or naphthalene.
Further, the R4Selected from H, methyl, ethyl, propyl, normal-butyl, n-pentyl, n-hexyl, phenyl, tolyl,
Ethylbenzene, xenyl or naphthalene.
Further, when Ar is not H, the skeleton structure of the Ar preferably is selected from following any structures：
Further, the bridge linkage group L1And L2It is respectively and independently selected from singly-bound, phenylene, biphenylene, naphthylene, Asia
One of pyridyl group.
Bridge linkage group L in general formula1And L2Hetero atom can also be independently selected from, in such as oxygen atom, nitrogen-atoms or sulphur atom
It is a kind of.
Further, formula（1）、（2）Or（3）One of middle A and B is N, and another is the H quilts in CH groups or CH groups
Methyl, ethyl, propyl, normal-butyl, n-pentyl ,-CF3、-SCH3, phenyl, tolyl, ethylbenzene, xenyl, naphthalene, carbazyl,
The monobasic CH groups of N- phenyl carbazole bases.
Work as R1Or R2When not being H, the R1Or R2Selected from following any structures：
In order to become apparent from illustrating present invention, lower mask body narration the present invention relates to compound preferred structure：
Compound 1
Compound 2
Compound 3
Compound 4
Compound 5
Compound 6
Compound 7
Compound 8
Compound 9
Compound 10
Compound 11
Compound 12
Compound 13
Compound 14
Compound 15
Compound 16
Compound 17
Compound 18.
The present invention provides a kind of fluorenes class derivatives of the base groups of -3- containing carbazole that can be applied in organic electroluminescence device
Object.
Further, the fluorene kind derivative of the bases of -3- containing the carbazole group can be used as in organic electroluminescence device
Phosphorescent light body material.
The present invention also provides a kind of organic electroluminescence devices, including substrate and sequentially form on the substrate
Anode layer, organic luminescence function layer and cathode layer；The organic luminescence function layer includes hole transmission layer, organic luminous layer
And electron transfer layer, the material of main part of the organic luminous layer are the fluorenes of the base groups of -3- containing carbazole described in one or more
Analog derivative.
Further, in organic electroluminescence device, the luminescent layer is made of material of main part and luminescent dye, described
Luminescent dye is phosphorescent coloring.
The fluorene kind derivative for the new bases of -3- containing the carbazole group that the present invention develops, preparation process is simple, the easy and material
Material has good thermal stability, there is the molecular orbit to match with phosphorescent coloring and triplet（T1）, in organic electroluminescence
It is good phosphorescent light body material in luminescent device.
Specific embodiment：
Example 1 below-embodiment 19 is the synthetic example of the application：
Various imidazos [1,2-a] pyrimidine halo derivatives and imidazo [1,2-A] pyrazine used are halogenated in the present invention
Derivative, for example, 5,7- dichloro-imidazoles simultaneously [1,2-a] pyrimidine, 6- bromines imidazo [1,2-a] pyrimidine, 3- bromines imidazo [1,2-a]
Pyrimidine, 7- chloro- 5- (methyl mercapto) imidazo [1,2-c] pyrimidine, bromo- 6- chlorine imidazo [1, the 2-a] pyrimidines of 3-, 2- (3- bromophenyls)
Imidazoles [1,2-a] and pyrimidine, the chloro- 2-p- tolylimidazols [1,2-a] of 6- and pyrimidine, 2- (4- bromophenyls)-imidazo [1,2-
A] -7- methylpyrimidines, 2- (3- bromophenyls)-imidazo [1,2-a] pyrimidine, 2- (3- bromophenyls)-imidazo [1,2-a] -7- first
Yl pyrimidines, 2- (4- bromophenyls)-imidazo [1,2-a] pyrimidine, 3- bromo- 7- (trifluoromethyl) imidazo [1,2-a] pyrimidine, 6- bromines
Imidazo [1,2-a] pyrazine, bromo- 8- chlorine imidazo [1, the 2-a] pyrazines of 3-, 6,8- bis- bromo- imidazoles [1,2-a] pyrazines, the chloro- miaows of 5-
Azoles simultaneously [1,2-a] pyrazine, 8- chlorine imidazo [1,2-a] pyrazine, 3- bromines imidazo [1,2-a] pyrazine, 2- bromines imidazo [1,2-a]
Pyrazine, can chemical industry at home etc., commercially available at home, chemical raw materials such as various aryl boric acids and its Knit-the-brows alcohol esters
It conveniently buys in product market；Some special aryl boric acid derivatives and intermediate can use common organic procedures to synthesize.
Embodiment 1
The synthesis of following structural compounds,
The first step,
In one 500 milliliters of there-necked flasks, with electric stirring, Ar gas shieldeds add in the carbazole of 16.7g（Molecular weight 167,
0.10mol）, iodo- 9, the 9- dimethyl fluorenes 44g of the bromo- 7- of 2-（Molecular weight 398,0.11mol）, cuprous iodide 1.9g（Molecular weight 190,
0.01mol）, potassium carbonate 28g（Molecular weight 138,0.203mol）, 18- crown-s 6 use 1.2g（Molecular weight 264,0.00455mol）, add
Enter the common 250ml of solvent DMPU.When return stirring 4 is small, is monitored and reacted with TLC.After the reaction was complete, naturally stirring be cooled to 80 DEG C with
Under, that is, 500ml water is added in, stirring has the precipitation of faint yellow solid product, filters out, dry.It is separated, obtained micro- with silica gel column chromatography
Yellow product 35.7g, molecular weight 437, purity 98.0%, yield 80.2%.
Second step,
In one 500 milliliters of there-necked flasks, with magnetic agitation, Ar gas shieldeds add in 7-（Carbazole -9- bases）The bromo- 9,9- diformazans of -2-
Base fluorenes 19.7g（Molecular weight 437,0.045mol）With the THF of 120ml, it is cooled to -78 DEG C, the nBuLi of 25ml2M is added dropwise
（0.05mol）, temperature maintains -78 DEG C always, stirs the B (OiPr) that 30ml is added dropwise after 10min at -78 DEG C3
（0.153mol）, dilute acid hydrolysis is added in after stirring to room temperature, upper strata is white solid.Filtering, separates solid product, water layer is neutralized to
Neutrality is extracted with ethyl acetate, and extracting solution is evaporated, and adds in diluted alkaline, withdraws the not molten impurity in alkali with ethyl acetate, water layer neutralizes
To neutrality, there is white solid precipitation, filter, obtain product.It there are 15.2g solid products, molecular weight 403, yield 83.6%.
3rd step,
In the there-necked flask of a 1000ml, with mechanical agitation, Ar gas shieldeds add in bromo- 6- chlorine imidazo [1, the 2-a] pyrimidines of 3-
7.86g（Molecular weight 231,0.034mol）, phenyl boric acid Knit-the-brows alcohol esters 7.14g（Molecular weight 204,0.035mol）, catalyst Pd
(PPh3)4Dosage 1.8g（Molecular weight 1154,0.001556mol）, aqueous sodium carbonate 120ml（2M）, toluene 300ml, ethyl alcohol
150ml.It is stirred at reflux, is monitored and reacted with TLC, the reaction was complete after reaction 1.5hs.Cooling, separates, is evaporated, use column chromatography methods
Separation product, eluent is with 1：4 ethyl acetate：Petroleum ether obtains 7.46g faint yellow solid compounds, purity 96.0%, production
Rate：92.0%.
4th step,
In the there-necked flask of a 1000ml, with mechanical agitation, it is phonetic to add in 3- phenyl -6- chlorine imidazos [1,2-a] for Ar gas shieldeds
Pyridine 7.16g（Molecular weight 229,0.030mol）, to bromobenzeneboronic acid Knit-the-brows alcohol esters 9.1g（Molecular weight 282,0.032mol）, catalyst
Pd(PPh3)4Dosage 1.8g（Molecular weight 1154,0.001556mol）, aqueous sodium carbonate 120ml（2M）, toluene 300ml, ethyl alcohol
150ml.It is stirred at reflux, is monitored and reacted with TLC, the reaction was complete after reaction 3.5hs.Cooling, separates, is evaporated, use column chromatography methods
Separation product, eluent is with 1：3 ethyl acetate：Petroleum ether obtains 9.0g faint yellow solid compounds, purity 97.0%, production
Rate：83.2%.
5th step,
1000 milliliters of there-necked flasks with magnetic agitation, add in 3- phenyl -6- p-bromophenyls imidazo ［ 1,2, a ］ pyrimidine 9.8g
（Molecular weight 349,0.028mol）, 7-（Carbazole -9- bases）- 9,9- dimethyl fluorene -2- boric acid 12.1g（Molecular weight 403,
0.03mol）, 4 usage amount 1.8g of Pd (PPh3)（Molecular weight 1154,0.00155mol）, sodium carbonate 175ml（2M）, toluene
175ml, ethyl alcohol 175ml.Argon gas displacement after, reflux, with TLC monitor react, 4 it is small when after the reaction was complete, cooling, separated base
Layer, is evaporated, carries out post separation with 1/10 ethyl acetate/petroleum ether, obtain the compound 1 of 14.46g, purity 99.1%, yield
81.5%。
Product MS（m/e）：628, elemental analysis（C45H32N4）：Theoretical value C：85.96%, H：5.13%, N：8.91%；It is real
Measured value C：85.92%, H：5.11%, N：8.97%.
Embodiment 2
The synthesis of compound 1
Building-up process is allocated as three steps, and the first step is same as the 5th step reaction in embodiment 1, simply by 3- phenyl therein-
6- p-bromophenyls imidazo ［ 1,2, a ］ pyrimidine is replaced with iodo- 9, the 9- dimethyl fluorenes of the bromo- 7- of 2-, by 7-（Carbazole -9- bases）-9,9-
Dimethyl fluorene -2- boric acid is replaced making raw material with 6,9- diphenyl carbazole -3- boric acid, and other raw materials and process are constant, is obtained corresponding
Monobromo intermediate；Second step is same as the second step in embodiment 1, simply by the bromo- 7- of 2-（- 9 base of carbazole）- 9,9- dimethyl fluorenes
The monobromo intermediate synthesized with the first step here replaces making raw material, and other raw materials and process are constant, obtains corresponding boric acid and derives
Object；3rd step is same as the 5th step reaction in embodiment 1, simply by 7- therein（Carbazole -9- bases）- 9,9- dimethyl fluorenes -2-
Boric acid is replaced making raw material with the boronic acid derivatives that second step here synthesizes, and other raw materials and process are constant, obtain compound 1.
Product MS（m/e）：780, elemental analysis（C57H40N4）：Theoretical value C：87.66%, H：5.16%, N：7.18%；It is real
Measured value C：87.62%, H：5.13%, N：7.25%.
Embodiment 3
The synthesis of compound 2
Building-up process is allocated as three steps, and the first step is same as the 5th step reaction in embodiment 1, simply by 3- phenyl therein-
6- p-bromophenyls imidazo ［ 1,2, a ］ pyrimidine is replaced with iodo- 9, the 9- dimethyl fluorenes of the bromo- 7- of 2-, by 7-（Carbazole -9- bases）-9,9-
Dimethyl fluorene -2- boric acid is replaced making raw material with 6,9- diphenyl carbazole -3- boric acid, and other raw materials and process are constant, is obtained corresponding
Monobromo intermediate；
Second step,
In the there-necked flask of a 2000ml, with mechanical agitation, Ar gas shieldeds.Add in the bromo- 7- of 2-（6,9- diphenyl carbazoles -3-
Base）- 9,9- dimethyl fluorenes 11.8g（Molecular weight 589,0.02mol）, connection pinacol borate 5.6g（Molecular weight 254.2,
0.022mol）, Pd (dppf) Cl23.2g（0.0044mol）, potassium acetate 36g（Molecular weight 138,0.26mol）, Isosorbide-5-Nitrae dioxane
500ml.Mechanical agitation is started, Ar gas shieldeds is kept after taking a breath 3 times at reduced pressure conditions, uses TLC（Thin-layer chromatography）Monitoring reaction,
Until raw material completely disappears, when back flow reaction 3 is small altogether.It lets cool, reaction system is allocated as two layers, separates organic layer, is evaporated, and use is general
Circulation method processing, obtains 11.2g products, yield 87.5%.
3rd step is same as the four-step reaction in embodiment 1, and simply bromobenzeneboronic acid pinacol ester is used here by therein
The pinacol borate derivative of second step synthesis replaces making raw material, and other raw materials and process are constant, obtain compound 2.
Product MS（m/e）：704, elemental analysis（C51H36N4）：Theoretical value C：86.90%, H：5.15%, N：7.95%；It is real
Measured value C：86.92%, H：5.10%, N：7.98%.
Embodiment 4
The synthesis of compound 3
Building-up process is allocated as two steps, and the first step is same as the second step in embodiment 2, simply by the bromo- 7- of 2-（6,9- diphenyl
Carbazole -3- bases）- 9,9- dimethyl fluorenes bromo- the 8- of 2-（9- phenyl carbazole -3- bases）- 6,6,12,12- tetramethyl -6,12- dihydros
Indeno ［ 1,2-b ］ fluorenes replaces making raw material, and other raw materials and process are constant, obtain corresponding pinacol borate derivative；Second
Step is same as the four-step reaction in embodiment 1, and simply bromobenzeneboronic acid pinacol ester second step here is synthesized by therein
Pinacol borate derivative replaces, and other raw materials and process are constant, obtain compound 3.
Product MS（m/e）：744, elemental analysis（C54H40N4）：Theoretical value C：87.07%, H：5.41%, N：7.52%；It is real
Measured value C：87.03%, H：5.42%, N：7.55%.
Embodiment 5
The synthesis of compound 4
Building-up process is allocated as two steps, and the first step is same as the second step in embodiment 1, simply by the bromo- 7- of 2-（6,9- diphenyl
Carbazole -3- bases）- 9,9- dimethyl fluorenes bromo- the 8- of 2-（6,9- diphenyl carbazole -3- bases）- 6,6,12,12- tetramethyls -6,12-
Dihydro indeno ［ 1,2-b ］ fluorenes replaces making raw material, and other raw materials and process are constant, obtain corresponding pinacol borate derivative；
Second step is same as the four-step reaction in embodiment 1, and simply bromobenzeneboronic acid pinacol ester second step here is closed by therein
Into pinacol borate derivative replace, other raw materials and process are constant, obtain compound 4.
Product MS（m/e）：820, elemental analysis（C60H44N4）：Theoretical value C：87.77%, H：5.40%, N：6.82%；It is real
Measured value C：87.75%, H：5.46%, N：6.79%.
Embodiment 6
The synthesis of compound 5
Building-up process is allocated as two steps, and the first step is same as the 5th step reaction in embodiment 1, simply by 7- therein（Carbazole-
9- bases）- 9,9- dimethyl fluorene -2- boric acid 7-（6,9- diphenyl carbazole -3- bases）- 9,9- dimethyl fluorene -2- boric acid replace, will
4-（3- phenylimidazoles simultaneously [1,2-a] pyrimidine -6- bases）Bromobenzene replaces making raw material with bromo- 6- chlorine imidazo [1, the 2-a] pyrimidines of 3-,
Its raw material and process are constant, obtain a corresponding chloromethylated intermediate；Second step is same as the 3rd step in embodiment 1, simply that 3- is bromo-
6- chlorine imidazo [1,2-a] pyrimidine is replaced making raw material with the chloromethylated intermediate that the first step here synthesizes, and other raw materials and process are not
Become, obtain compound 5.
Product MS（m/e）：704, elemental analysis（C51H36N4）：Theoretical value C：86.90%, H：5.15%, N：7.95%；It is real
Measured value C：86.93%, H：5.16%, N：7.91%.
Embodiment 7
The synthesis of compound 6
Synthesis step is same as the four-step reaction in embodiment 1, simply by therein to bromobenzeneboronic acid pinacol ester 8-
（N- phenyl carbazole -3- bases）- 6,6,12,12- tetramethyl -6,12- dihydro indeno ［ 1,2-b ］ fluorenes -2- pinacol borates derive
Object replaces, and by 3- phenyl -6- chlorine imidazo [1,2-a] pyrimidine, with the bromo- 7- trifluoromethyl imidazoles of 3-, simultaneously [1,2-a] pyrimidine makees original
Material, other raw materials and process are constant, obtain compound 6.
Product MS（m/e）：736, elemental analysis（C49H35F3N4）：Theoretical value C：79.87%, H：4.79%, F：7.74%,
N：7.60%；Measured value C:79.85%, H：4.76%, F：7.76%, N：7.63%.
Embodiment 8
The synthesis of compound 7
Synthesis step is same as the four-step reaction in embodiment 1, simply by therein to bromobenzeneboronic acid pinacol ester 8-
（N- phenyl carbazole -3- bases）- 6,6,12,12- tetramethyl -6,12- dihydro indeno ［ 1,2-b ］ fluorenes -2- pinacol borates derive
Object replaces, and 3- phenyl -6- chlorine imidazo [1,2-a] pyrimidine 5- methyl mercaptos -7- chlorine imidazo [1,2-a] pyrimidine is made raw material,
Other raw materials and process are constant, obtain compound 7.
Product MS（m/e）：714, elemental analysis（C49H38N4S）：Theoretical value C：82.32%, H：5.36%, N：7.84%,
S：4.48%；Measured value C：82.36%, H：5.34%, N：7.86%, S：4.44%.
Embodiment 9
The synthesis of compound 8
Synthesis step is allocated as two steps, and the first step is same as the four-step reaction in embodiment 1, simply by therein to bromobenzene boron
Sour pinacol ester 8-（9- phenyl carbazole -3- bases）- 6,6,12,12- tetramethyl -6,12- dihydro indeno ［ 1,2-b ］ fluorenes -2- boron
Sour pinacol ester derivative replaces, and 3- phenyl -6- chlorine imidazo [1,2-a] pyrimidine is phonetic with the bromo- 6- chlorine imidazos [1,2-a] of 3-
Pyridine replaces making raw material, and other raw materials and process are constant, obtain a chloromethylated intermediate；The 3rd step that second step is same as in embodiment 1 is anti-
Should, simply bromo- 6- chlorine imidazo [1, the 2-a] pyrimidines of 3- are replaced making raw material with the chloromethylated intermediate that second step here synthesizes,
Its raw material and process are constant, obtain compound 8.
Product MS（m/e）：744, elemental analysis（C54H40N4）：Theoretical value C：87.07%, H：5.41%, N：7.52%；It is real
Measured value C：87.03%, H：5.43%, N：7.54%.
Embodiment 10
The synthesis of compound 9
Synthesis step is allocated as three steps, and the first step is same as the four-step reaction in embodiment 1, simply by 3- phenyl -6- chlorine miaows
Simultaneously ［ 1,2, a ］ pyrimidine is replaced azoles with bromo- 8- chlorine imidazo [1, the 2-A] pyrazines of 3-, and other raw materials and process are constant, obtain 3- to bromine
Phenyl -8- chlorine imidazo [1,2-a] pyrimidine；Second step is same as the 5th step reaction in embodiment 1, simply by -6- pairs of 3- phenyl
3- p-bromophenyl -8- chlorine imidazo [1,2-a] the pyrimidine generations that bromophenyl imidazo ［ 1,2, a ］ pyrimidine is synthesized with the first step here
It replaces, 7-（Carbazole -9- bases）- 9,9- dimethyl fluorene -2- boric acid 7-（9- phenyl carbazole -3- bases）- 9,9- dimethyl fluorene -2- boric acid
Instead of making raw material, other raw materials and process are constant, obtain a chloromethylated intermediate；3rd step is same as the three-step reaction in embodiment 1,
Simply bromo- 6- chlorine imidazo ［ 1,2, a ］ pyrimidines of 3- are replaced with the chloromethylated intermediate that second step here synthesizes, other raw materials and mistake
Journey is constant, obtains compound 9.
Product MS（m/e）：704, elemental analysis（C51H36N4）：Theoretical value C：86.90%, H：5.15%, N：7.95%；It is real
Measured value C：86.88%, H：5.14%, N：7.98%.
Embodiment 11
The synthesis of compound 10
Synthesis step is allocated as three steps, and the first step is same as the four-step reaction in embodiment 1, simply by 3- phenyl -6- chlorine miaows
Simultaneously ［ 1,2, a ］ pyrimidine is replaced azoles with bromo- 8- chlorine imidazo [1, the 2-A] pyrazines of 3-, and other raw materials and process are constant, obtain 3- to bromine
Phenyl -8- chlorine imidazo [1,2-a] pyrimidine；Second step is same as the 5th step reaction in embodiment 1, simply by -6- pairs of 3- phenyl
3- p-bromophenyl -8- chlorine imidazo [1,2-a] the pyrimidine generations that bromophenyl imidazo ［ 1,2, a ］ pyrimidine is synthesized with the first step here
It replaces, 7-（Carbazole -9- bases）- 9,9- dimethyl fluorene -2- boric acid 7-（9- phenyl carbazole -3- bases）- 9,9- dimethyl fluorene -2- boric acid
Instead of making raw material, other raw materials and process are constant, obtain a chloromethylated intermediate；3rd step is same as the three-step reaction in embodiment 1,
Simply bromo- 6- chlorine imidazo ［ 1,2, a ］ pyrimidines of 3- are replaced with the chloromethylated intermediate that second step here synthesizes, phenyl boric acid pinacol
Ester 4-（Carbazole -9- bases）Phenyl boric acid pinacol ester replaces making raw material, and other raw materials and process are constant, obtain compound 10.
Product MS（m/e）：793, elemental analysis（C57H39N5）：Theoretical value C：86.23%, H：4.95%, N：8.82%；It is real
Measured value C：86.26%, H：4.94%, N：8.80%.
Embodiment 12
The synthesis of compound 11
Building-up process is allocated as two steps, and the first step is same as the 3rd step in embodiment 2, simply by the bromo- 6- chlorine imidazos of 3- [1,
2-a] pyrimidine replaces with bromo- 8- chlorine imidazo [1,2-a] pyrazines of 3-, phenyl boric acid Knit-the-brows alcohol ester N- phenyl carbazole -3- boric acid Knit-the-brows
Which alcohol ester replaces making raw material, and other raw materials and process are constant, obtain chloro midbody product；Second step is same as in embodiment 1
Four-step reaction, simply by therein to bromobenzeneboronic acid pinacol ester 7-（N- phenyl carbazole -3- bases）- 9,9- dimethyl fluorenes-
The chloro intermediate that 2- boric acid Knit-the-brows alcohol esters replace, 3- phenyl -6- chlorine imidazo [1,2-a] pyrimidine is synthesized with the first step here produces
Object replaces, and other raw materials and process are constant, obtain compound 11.
Product MS（m/e）：793, elemental analysis（C57H39N5）：Theoretical value C：86.23%, H：4.95%, N：8.82%；It is real
Measured value C：86.25%, H：4.91%, N：8.84%.
Embodiment 13
The synthesis of compound 12
Building-up process is allocated as two steps, and the first step is same as the 3rd step in embodiment 2, simply by the bromo- 6- chlorine imidazos of 3- [1,
2-a] pyrimidine replaces with bromo- 8- chlorine imidazo [1,2-a] pyrazines of 3-, phenyl boric acid Knit-the-brows alcohol ester dibenzofurans -3- boric acid Knit-the-brows
Which alcohol ester replaces making raw material, and other raw materials and process are constant, obtain chloro midbody product；Second step is same as in embodiment 1
Four-step reaction, simply by therein to bromobenzeneboronic acid pinacol ester 7-（N- phenyl carbazole -3- bases）- 9,9- dimethyl fluorenes-
The chloro intermediate that 2- boric acid Knit-the-brows alcohol esters replace, 3- phenyl -6- chlorine imidazo [1,2-a] pyrimidine is synthesized with the first step here produces
Object replaces, and other raw materials and process are constant, obtain compound 12.
Product MS（m/e）：718, elemental analysis（C51H34N4O）：Theoretical value C：85.21%, H：4.77%, N：7.79%,
O：2.23%；Measured value C：85.25%, H：4.74%, N：7.75%, O：2.26%.
Embodiment 14
The synthesis of compound 13
Building-up process is allocated as two steps, and the first step is same as the 3rd step in embodiment 2, simply by the bromo- 6- chlorine imidazos of 3- [1,
2-a] pyrimidine replaces with bromo- 8- chlorine imidazo [1,2-a] pyrazines of 3-, phenyl boric acid Knit-the-brows alcohol ester dibenzothiophenes -3- boric acid Knit-the-brows
Which alcohol ester replaces making raw material, and other raw materials and process are constant, obtain chloro midbody product；Second step is same as in embodiment 1
Four-step reaction, simply by therein to bromobenzeneboronic acid pinacol ester 7-（N- phenyl carbazole -3- bases）- 9,9- dimethyl fluorenes-
The chloro intermediate that 2- boric acid Knit-the-brows alcohol esters replace, 3- phenyl -6- chlorine imidazo [1,2-a] pyrimidine is synthesized with the first step here produces
Object replaces, and other raw materials and process are constant, obtain compound 13.
Product MS（m/e）：734, elemental analysis（C51H34N4S）：Theoretical value C：83.35%, H：4.66%, N：7.62%,
S：4.36%；Measured value C：83.38%, H：4.62%, N：7.62%, S：4.38%.
Embodiment 15
The synthesis of compound 14
Building-up process is allocated as two steps, and the first step is same as the 3rd step in embodiment 2, simply by the bromo- 6- chlorine imidazos of 3- [1,
2-a] pyrimidine is replaced with bromo- 8- chlorine imidazo [1,2-a] pyrazines of 3-, phenyl boric acid Knit-the-brows alcohol esters are with to phenyl phenyl boric acid Knit-the-brows alcohol esters
Instead of making raw material, other raw materials and process are constant, obtain chloro midbody product；Second step is same as the 4th step in embodiment 1
Reaction, simply by therein to bromobenzeneboronic acid pinacol ester 7-（N- phenyl carbazole -3- bases）- 9,9- dimethyl fluorene -2- boric acid
The chloro midbody product generation that Knit-the-brows alcohol esters replace, 3- phenyl -6- chlorine imidazo [1,2-a] pyrimidine is synthesized with the first step here
It replaces, other raw materials and process are constant, obtain compound 14.
Product MS（m/e）：704, elemental analysis（C51H36N4）：Theoretical value C：86.90%, H：5.15%, N：7.95%；It is real
Measured value C：86.93%, H：5.17%, N：7.90%.
Embodiment 16
The synthesis of compound 15
Building-up process is allocated as two steps, and the first step is same as the 3rd step in embodiment 2, simply by phenyl boric acid Knit-the-brows alcohol esters N-
Phenyl carbazole -3- boric acid Knit-the-brows alcohol esters replace making raw material, and other raw materials and process are constant, obtain chloro midbody product；Second
Step is same as the four-step reaction in embodiment 1, simply by therein to bromobenzeneboronic acid pinacol ester 7-（N- phenyl carbazoles -3-
Base）- 9,9- dimethyl fluorene -2- boric acid Knit-the-brows alcohol esters replace, 3- phenyl -6- chlorine imidazo [1,2-a] pyrimidine first step here
The chloro midbody product of synthesis replaces, and other raw materials and process are constant, obtain compound 15.
Product MS（m/e）：793, elemental analysis（C57H39N5）：Theoretical value C：86.23%, H：4.95%, N：8.82%；It is real
Measured value C：86.21%, H：4.93%, N：8.86%.
Embodiment 17
The synthesis of compound 16
Building-up process is allocated as two steps, and the first step is same as the 3rd step in embodiment 2, simply by phenyl boric acid Knit-the-brows alcohol esters with two
Which alcohol ester of benzofuran -3- boric acid Knit-the-brows replaces making raw material, and other raw materials and process are constant, obtain chloro midbody product；Second
Step is same as the four-step reaction in embodiment 1, simply by therein to bromobenzeneboronic acid pinacol ester 7-（N- phenyl carbazoles -3-
Base）- 9,9- dimethyl fluorene -2- boric acid Knit-the-brows alcohol esters replace, 3- phenyl -6- chlorine imidazo [1,2-a] pyrimidine first step here
The chloro midbody product of synthesis replaces, and other raw materials and process are constant, obtain compound 16.
Product MS（m/e）：718, elemental analysis（C51H34N4O）：Theoretical value C：85.21%, H：4.77%, N：7.79%,
O：2.23%；Measured value C：85.24%, H：4.73%, N：7.76%, O：2.27%.
Embodiment 18
The synthesis of compound 17
Building-up process is allocated as two steps, and the first step is same as the 3rd step in embodiment 2, simply by phenyl boric acid Knit-the-brows alcohol esters with two
Which alcohol ester of benzothiophene -3- boric acid Knit-the-brows replaces making raw material, and other raw materials and process are constant, obtain chloro midbody product；Second
Step is same as the four-step reaction in embodiment 1, simply by therein to bromobenzeneboronic acid pinacol ester 7-（N- phenyl carbazoles -3-
Base）- 9,9- dimethyl fluorene -2- boric acid Knit-the-brows alcohol esters replace, 3- phenyl -6- chlorine imidazo [1,2-a] pyrimidine first step here
The chloro midbody product of synthesis replaces, and other raw materials and process are constant, obtain compound 17.
Product MS（m/e）：734, elemental analysis（C51H34N4S）：Theoretical value C：83.35%, H：4.66%, N：7.62%,
S：4.36%；Measured value C：83.32%, H：4.64%, N：7.65%, S：4.39%.
Embodiment 19
The synthesis of compound 18
Compound 18
Building-up process is allocated as two steps, and the first step is same as the 3rd step in embodiment 2, simply by phenyl boric acid Knit-the-brows alcohol esters use pair
Phenyl phenyl boric acid Knit-the-brows alcohol esters replace making raw material, and other raw materials and process are constant, obtain chloro midbody product；Second step is same as
Four-step reaction in embodiment 1, simply by therein to bromobenzeneboronic acid pinacol ester 7-（N- phenyl carbazole -3- bases）-9,
9- dimethyl fluorene -2- boric acid Knit-the-brows alcohol esters replace, 3- phenyl -6- chlorine imidazo [1,2-a] pyrimidine is synthesized with the first step here
Chloro midbody product replaces, and other raw materials and process are constant, obtain compound 18.
Product MS（m/e）：704, elemental analysis（C51H36N4）：Theoretical value C：86.90%, H：5.15%, N：7.95%；It is real
Measured value C：86.92%, H：5.12%, N：7.96%.
Here is the Application Example of the compounds of this invention：
Embodiment 20
The preparation of electroluminescent device and result
Prepare the preferred embodiment of device：
（1）Device designs
Compare the performance of these materials for convenience, the present invention devises a simple electroluminescence device（Substrate/anode/sky
Cave implanted layer（HIL）/ hole transmission layer（HTL）/ phosphorescence host（HOST）:Phosphorescent coloring (Dopant)/electron transfer layer
(ETL)/electron injecting layer（EIL）/ cathode）, using only compound 1,3,4,7,9,10,11,13,16,18 as phosphorescence host
Material illustration, CBP compare material, Ir as phosphorescence host（ppy）3As phosphorescent coloring.The structure of CBP and phosphorescent coloring is：
Substrate can use the substrate in conventional organic luminescence device, such as：Glass or plastics.In the device system of the present invention
Glass substrate is selected in work, ITO makees anode material.
Hole injection layer selects 2-TNATA.
Various tri-arylamine group materials may be employed in hole transmission layer.Selected hole passes in the element manufacturing of the present invention
Defeated material is NPB.
Selected electron transport material is Bphen in the element manufacturing of the present invention.
The structural formula of wherein 2-TNATA, NPB, Bphen is respectively：
Metal and its mixture structure, such as Mg may be employed in cathode：Ag、Ca：Ag etc. or electron injecting layer/gold
Belong to layer structure, such as LiF/Al, Li2The common cathodes structure such as O.The selected electron injection material in the element manufacturing of the present invention
It is LiF, cathode material is Al.
（2）Element manufacturing
The glass plate for being coated with transparent conductive layer in commercial detergent is ultrasonically treated, is rinsed in deionized water,
In acetone：Ultrasonic oil removing in alcohol mixed solvent, is baked under clean environment and removes moisture content completely, clear with ultraviolet light and ozone
It washes, and with low energy cation beam bombarded surface;
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-4Pa, above-mentioned
Vacuum evaporation 2-TNATA is as hole injection layer on anode tunic, and evaporation rate 0.1nm/s, vapor deposition film thickness is 20nm；In sky
Vacuum evaporation NPB is as hole transmission layer on the implanted layer of cave, and evaporation rate 0.1nm/s, vapor deposition film thickness is 40nm；
On hole transmission layer using the double source vacuum evaporation present invention phosphorescent light body material 1,3,4,7,9,10,11,
13rd, 16,18 phosphorescent coloring Ir is deposited altogether simultaneously（ppy）3, phosphorescent light body material can also replace with CBP.Phosphorescence host and dyestuff are total to
The luminescent layer as device is deposited, evaporation rate 0.1nm/s, the rate of phosphorescent coloring is 0.015nm/S, and vapor deposition total film thickness is
30nm；
Electron transfer layers of the one layer of compound Bphen of vacuum evaporation as device, evaporation rate are on luminescent layer
0.1nm/s, vapor deposition total film thickness are 20nm；
In electron transfer layer（ETL）Upper vacuum evaporation LiF is as electron injecting layer, thickness 0.5nm.It is steamed on LiF layers
Plate the Al layers of cathode as device, thickness 150nm.
Device performance see the table below（Device architecture：ITO/2-TNATA(20nm)/NPB（40nm）/ phosphorescence host:15%Ir
（ppy）3(30nm)/Bphen（20nm）/LiF（0.5nm）/Al（150nm））
The above result shows that new organic materials of the invention are used for organic electroluminescence device, can effectively reduce
Landing voltage improves current efficiency, is phosphorescent light body material of good performance.
Although the present invention is described in conjunction with the embodiments, the invention is not limited in above-described embodiments, should manage
Solution, under the guiding of present inventive concept, those skilled in the art can carry out various modifications and improve, and appended claims summarise
The scope of the present invention.
Claims (6)
1. a kind of fluorene kind derivative of the bases of -3- containing carbazole group, it is characterised in that：With the structure as shown in formula (2) or (3),
Or it is compound 7：
Wherein：
One of A and B are N, and another is CH groups；
Ar is selected from
R1And R2Separately selected from H, phenyl, xenyl, carbazyl, N- phenyl carbazoles base, trifluoromethyl, dibenzothiophenes
Base or dibenzofuran group；
R3Selected from phenyl；
R4Selected from H, phenyl；
The bridge linkage group L1And L2It is independently selected from one of singly-bound, phenylene；
Compound 7.
2. a kind of fluorene kind derivative of the bases of -3- containing carbazole group, which is characterized in that the fluorenes class of the bases of -3- containing the carbazole group is spread out
Biology is selected from the compound of following structural formula：
Compound 1
Compound 2
Compound 3
Compound 4
Compound 5
Compound 6
Compound 8
Compound 9
Compound 10
Compound 11
Compound 12
Compound 13
Compound 14
Compound 15
Compound 16
Compound 17
Compound 18
3. a kind of fluorene kind derivative of the claim 1~2 any one of them base groups of -3- containing carbazole is in organic electroluminescence
Application in part.
It 4. applies according to claim 3, which is characterized in that the fluorene kind derivative of the bases of -3- containing the carbazole group is used as phosphorus
Light material of main part.
5. a kind of organic electroluminescence device, including substrate and anode layer, organic light emission on the substrate are sequentially formed
Functional layer and cathode layer；The organic luminescence function layer includes hole transmission layer, organic luminous layer and electron transfer layer,
It is characterized in that：The material of main part of the organic luminous layer contains click to be one or more as according to any one of claims 1 to 2
The fluorene kind derivative of azoles -3- base groups.
6. a kind of organic electroluminescence device according to claim 5, which is characterized in that the organic luminous layer is by main body
Material and luminescent dye composition, the luminescent dye are phosphorescent coloring.
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