CN105765030B - Novel light-emitting compound and organic illuminating element comprising it - Google Patents
Novel light-emitting compound and organic illuminating element comprising it Download PDFInfo
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- CN105765030B CN105765030B CN201480063382.0A CN201480063382A CN105765030B CN 105765030 B CN105765030 B CN 105765030B CN 201480063382 A CN201480063382 A CN 201480063382A CN 105765030 B CN105765030 B CN 105765030B
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- PLAZTCDQAHEYBI-UHFFFAOYSA-N Cc1ccccc1[N+]([O-])=O Chemical compound Cc1ccccc1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- JXMZUNPWVXQADG-UHFFFAOYSA-N [O-][N+](c(cccc1)c1I)=O Chemical compound [O-][N+](c(cccc1)c1I)=O JXMZUNPWVXQADG-UHFFFAOYSA-N 0.000 description 1
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Abstract
The organic luminescent compounds of the present invention are due to charge transfer excellent and have high triplet energy and high Tg, to make it have low driving voltage, high efficiency, low power consumption, long-life when applied to organic illuminating element.
Description
Technical field
The present invention relates to novel light-emitting compound and include its organic illuminating element.
Background technology
Recently, emissive type can low voltage drive organic illuminating element with as flat panel displaying element mainstream liquid
Crystal display (LCD, liquid crystal display) is compared, and field angle, contrast etc. are excellent, do not need backlight, can be real
Existing light weight and slim, in terms of the power consumption on it is also advantageous, color reproduction range is wide, to be closed as next-generation display element
Note.
The material for being used as organic matter layer in organic illuminating element is broadly divided into luminescent material by function, material is injected in hole
Material, hole mobile material, electron transport material, electron injection material etc..Above-mentioned luminescent material can be divided into macromolecule by molecular weight
And low molecule, by luminescence mechanism can be divided into the fluorescent material of the singlet excited from electronics and from electronics it is triple swash
The phosphor material of state is sent out, luminescent material can be divided into blue, green, red illuminating material and in order to present more by luminescent color
Yellow needed for good natural colour and orange light emitting materials.In addition, in order to increase through the increase of excitation purity and energy transfer
Luminous efficiency can use main body/dopant system as luminescent substance.Its principle is as follows：If mixed in luminescent layer few
The dopant that band gap is small compared with the main body of main composition luminescent layer and luminous efficiency is excellent of amount, then generate in main body
Exciton transfer sends out efficient light to dopant.At this point, the wavelength of main body is moved to the wave band of dopant, therefore can root
According to the type of used dopant and main body, the light of desired wavelength is obtained.
So far, as the substance for such organic illuminating element, it is known that multiple compounds, but using in the past
In the case of the organic illuminating element of known substance, due to high driving voltage, poor efficiency and short life in functionization side
There are many difficulties in face.Therefore, in order to using the substance with excellent specific property come develop with low voltage drive, high brightness with
And the long-life organic illuminating element and be continually striving to.
Invention content
As described above in order to solve the problems, such as, the object of the present invention is to provide a kind of novel light-emitting compounds, this shines
Compound is due to charge transfer excellent and has high triplet energy and high Tg, to when applied to organic illuminating element
Low driving voltage, high efficiency, low power consumption, long-life can be made it have.
The present invention also aims to, provide by can be realized comprising above compound low driving voltage, high efficiency,
Low power consumption, the organic illuminating element of long-life.
To achieve the goals above, the present invention provides the luminophor represented by following chemical formula 1：
[chemical formula 1]
A-L-B
In above-mentioned formula,
A be following A 1 to the structure represented by A30 in one kind, wherein hydrogen included in A can each independently by
Deuterium, halogen, amino, itrile group, nitro substitution or unsubstituted,
L is by deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Alkenyl, C2-30Alkynyl, C1-30Alkane
Oxygroup, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl6-50Aryl；Or by deuterium, halogen
Element, amino, itrile group, nitro, C1-30Alkyl, C2-30Alkenyl, C2-30Alkynyl, C1-30Alkoxy, C6-30Aryloxy group,
C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl2-50Heteroaryl,
B be following B1 to B10 represented by structure in one kind, wherein hydrogen included in B can each independently by
Deuterium, halogen, amino, itrile group, nitro substitution or unsubstituted.
In above structure ,-* is binding site, Ar1And Ar2It is each independently hydrogen；Deuterium；By deuterium, halogen, amino, itrile group,
The substituted or unsubstituted C of nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkenyl；
By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；Replaced by deuterium, halogen, amino, itrile group, nitro
Or unsubstituted C1-30Alkoxy；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；Quilt
The substituted or unsubstituted C of deuterium, halogen, amino, itrile group, nitro6-30Aryl；Or it is taken by deuterium, halogen, amino, itrile group, nitro
Generation or unsubstituted C2-30Heteroaryl.
In addition, the present invention is provided in organic matter layer comprising the compound represented by above-mentioned chemical formula 1 as luminescent substance
Organic illuminating element.
The luminophor of the present invention is due to charge transfer excellent and has high triplet energy and high Tg, thus
Low driving voltage, high efficiency, low power consumption, long-life can be made it have when applied to organic illuminating element.
Description of the drawings
Fig. 1 schematically shows the section of OLED according to an embodiment of the invention.
Reference numeral
10：Substrate
11：Anode
12：Hole injection layer
13：Hole transmission layer
14：Luminescent layer
15：Electron transfer layer
16：Cathode
Specific implementation mode
The compound of the present invention is characterized in that being indicated by following chemical formula 1.
[chemical formula 1]
A-L-B
* in above-mentioned formula,
A be following A 1 to the structure represented by A30 in one kind, wherein hydrogen included in A can each independently by
Deuterium, halogen, amino, itrile group, nitro substitution or unsubstituted,
L is by deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Alkenyl, C2-30Alkynyl, C1-30Alkane
Oxygroup, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl6-50Aryl；Or by deuterium, halogen
Element, amino, itrile group, nitro, C1-30Alkyl, C2-30Alkenyl, C2-30Alkynyl, C1-30Alkoxy, C6-30Aryloxy group,
C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl2-50Heteroaryl, it is preferable that L be following structures in one kind,
B be following B1 to B10 represented by structure in one kind, wherein hydrogen included in B can each independently by
Deuterium, halogen, amino, itrile group, nitro substitution or unsubstituted.
In above structure ,-* is binding site,
Ar1And Ar2It is each independently hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30's
Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkenyl；By deuterium, halogen, amino, itrile group, nitre
The substituted or unsubstituted C of base2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxy；
By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；It is taken by deuterium, halogen, amino, itrile group, nitro
Generation or unsubstituted C6-30Aryl；Or by deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Heteroaryl.
Preferably, above-mentioned Ar1And Ar2The one kind being each independently in following structures.
In the present invention, one kind in the structure that the compound represented by above-mentioned chemical formula 1 is preferably as follows.
In above structure, X1And X2It is each independently S, O, Se, Te or N-Ar3, wherein Ar3For hydrogen；Deuterium；By deuterium, halogen
The substituted or unsubstituted C of element, amino, itrile group, nitro1-30Alkyl；Replaced or do not taken by deuterium, halogen, amino, itrile group, nitro
The C in generation2-30Alkenyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, ammonia
The substituted or unsubstituted C of base, itrile group, nitro1-30Alkoxy；It is substituted or unsubstituted by deuterium, halogen, amino, itrile group, nitro
C6-30Aryloxy group；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryl；Or by deuterium, halogen, ammonia
The substituted or unsubstituted C of base, itrile group, nitro2-30Heteroaryl,
Ar is by deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Alkenyl, C2-30Alkynyl, C1-30Alkane
Oxygroup, C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl6-50Aryl；Or by deuterium, halogen
Element, amino, itrile group, nitro, C1-30Alkyl, C2-30Alkenyl, C2-30Alkynyl, C1-30Alkoxy, C6-30Aryloxy group,
C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl6-50Heteroaryl.
In the present invention, the compound represented by above-mentioned chemical formula 1 is more preferably one kind in structure as follows.
In above structure, X1And X2It is each independently S, O, Se, Te or N-Ar4, wherein Ar4For hydrogen；Deuterium；By deuterium, halogen
The substituted or unsubstituted C of element, amino, itrile group, nitro1-30Alkyl；Replaced or do not taken by deuterium, halogen, amino, itrile group, nitro
The C in generation2-30Alkenyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, ammonia
The substituted or unsubstituted C of base, itrile group, nitro1-30Alkoxy；It is substituted or unsubstituted by deuterium, halogen, amino, itrile group, nitro
C6-30Aryloxy group；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryl；Or by deuterium, halogen, ammonia
The substituted or unsubstituted C of base, itrile group, nitro2-30Heteroaryl,
Y is CR1Or N, wherein R1For hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30's
Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkenyl；By deuterium, halogen, amino, itrile group, nitre
The substituted or unsubstituted C of base2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxy；
By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；It is taken by deuterium, halogen, amino, itrile group, nitro
Generation or unsubstituted C6-30Aryl；Or by deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Heteroaryl.
In the present invention, the preference of the compound represented by above-mentioned chemical formula 1 is as follows.
The compound of chemical formula 1 according to the present invention is due to charge transfer excellent and has high triplet energy and height
Tg, to which low driving voltage, high efficiency, low power consumption, long-life can be made it have when applied to organic illuminating element.
In addition, the compound of the present invention can be manufactured by process shown in following reaction equations 1.
[reaction equation 1]
It, can be with application response formula 1-1 as concrete example.
[reaction equation 1-1]
In above-mentioned reaction equation 1 and reaction equation 1-1, A, L, B, X1、X2It is identical as the definition in above-mentioned chemical formula 1.
In addition, the present invention is provided in organic matter layer comprising the compound represented by above-mentioned chemical formula 1 as luminescent substance
Organic illuminating element.At this point, the compound of the present invention can be used alone or together with well known organic luminescent compounds
It uses.
In addition, the organic illuminating element of the present invention includes 1 layer or more containing the compound represented by above-mentioned chemical formula 1
Organic matter layer, the manufacturing method of above-mentioned organic illuminating element as described below.
Above-mentioned organic illuminating element can include hole injection layer between anode (anode) and cathode (cathode)
(HIL), the organic matter layers one such as hole transmission layer (HTL), luminescent layer (EML), electron transfer layer (ETL), electron injecting layer (EIL)
Layer or more.
First, anode is formed in anode electrode substance of the substrate top vapor deposition with high work function.At this point, above-mentioned base
Plate can use the substrate used in common organic illuminating element, especially with mechanical strength, thermal stability, transparent
Property, surface smoothness, handling easiness and the excellent glass substrate or transparent plastic substrate of water proofing property are preferred.In addition, as sun
Pole electrode substance, tin indium oxide (ITO), indium zinc oxide (IZO), the tin oxide that transparent and electrically conductive can be used excellent
(SnO2), zinc oxide (ZnO) etc..Above-mentioned anode electrode can be deposited with substance by common anode forming method, specifically
It can be deposited by vapour deposition method or sputtering method.
Secondly, vacuum vapour deposition, spin-coating method, casting, LB (Langmuir-Blo dgett, Lang Gemiaoer can be passed through
Blodget) the methods of method, form hole injection layer substance on above-mentioned anode electrode top, but from being easy to get uniform film
Matter and it is not likely to produce pin holeDeng from the aspect of, preferably formed by vacuum vapour deposition.By upper
Vacuum vapour deposition is stated come in the case of forming hole injection layer, although evaporation condition is according to the material as hole injection layer
Compound, the structure of target hole injection layer and thermal characteristics etc. and it is different, but generally preferably 50-500 DEG C vapor deposition temperature,
10-8To 10-3Hold in the palm (torr) vacuum degree, 0.01 toThe evaporation rate of/sec,It is fitted in 5 μm of Layer thickness
Work as selection.
Above-mentioned hole injection layer substance is not particularly limited, and can use disclosed in U.S. Patent No. 4,356,429
Phthalocyanine compounds or the star-like amine such as CuPcDerivative species, i.e. TCTA (4,4', 4 "-
Three (N- carbazyls) triphenylamines), m-MTDATA (4,4', 4 "-three (3- MethYlphenylaminos) triphenylamine), m-MTDAPB
(4,4', 4 "-three (3- MethYlphenylaminos) phenoxy group benzene), HI-406 (N1,N1'-(biphenyl -4,4'- diyl) bis- (N1(naphthalene-
1- yls)-N4,N4Diphenyl benzene -1,4- diamines) etc. be used as hole injection layer substance.
It secondly, can be by the methods of vacuum vapour deposition, spin-coating method, casting, LB methods, on above-mentioned hole injection layer top
Hole transmission layer substance is formed, but from the aspect of being easy to get uniform film quality and being not likely to produce pin hole etc., it is preferably logical
Vacuum vapour deposition is crossed to be formed.By above-mentioned vacuum vapour deposition come in the case of forming hole transmission layer, though evaporation condition
It is so different according to used compound, but usually selected in the condition and range almost the same with the formation of hole injection layer
It is preferred.
In addition, above-mentioned hole transmission layer substance is not particularly limited, can be used in hole transmission layer it is common
Arbitrarily selection uses in known substance.Specifically, above-mentioned hole transmission layer substance can use N- phenyl carbazoles, polyethylene click
The carbazole derivates such as azoles, N, N'- bis- (3- aminomethyl phenyls)-N, N'- diphenyl-[1,1- xenyl] -4,4'- diamines (TPD), N,
(naphthalene -1- bases)-N,N' diphenyl benzidines of N'- bis- (α-NPD) etc. have the common amine derivative etc. of aromatic fused ring.
It later, can be by the methods of vacuum vapour deposition, spin-coating method, casting, LB methods, on above-mentioned hole transmission layer top
Luminescent layer substance is formed, but from the aspect of being easy to get uniform film quality and being not likely to produce pin hole etc., preferably by true
Empty vapour deposition method is formed.By above-mentioned vacuum vapour deposition come in the case of forming luminescent layer, although evaporation condition is according to institute
The compound that uses and it is different, but usually select to be preferred in the condition and range almost the same with the formation of hole injection layer.This
Outside, above-mentioned emitting layer material can use the compound represented by the chemical formula 1 of the present invention as main body or dopant.
It, can be by phosphorescence or fluorescence in the case of the compound represented by chemical formula 1 is stated in use as light emitting host
Dopant is used together to form luminescent layer.At this point, as fluorescent dopants, can use from light extraction Xing Chan companies
IDE102, IDE105 or BD142 (N that (Idemitsu companies) can buy6,N12Bis- (3,4- 3,5-dimethylphenyls)-N6,N12- twoBase- 6,12- diamines), as phosphorescent dopants, vacuum evaporation (doping) there can be green phosphorescent dopant Ir jointly
(ppy)3(three (2- phenylpyridines) close iridium), as blue phosphorescent dopant F2Irpic (it is bis- [4,6- difluorophenyl pyridinato-N,
C2 '] pyridinecarboxylic conjunction iridium (III), iridium III bis [4,6-di-fluorophenyl-pyridinato-N, C2 ']
Picolinate), the red phosphorescent dopant RD61 etc. of UDC companies.The doping concentration of dopant is not particularly limited, but opposite
In 100 parts by weight of main body, preferably with 0.01 to 15 parts by weight doped with dopant.If the content of dopant is less than 0.01 weight
Part, then there are problems that developing the color and being unable to complete successfully because dopant dose is insufficient, more than 15 parts by weight, exist
The problem of efficiency drastically reduces due to concentration quenching phenomena.
In addition, in the case of in luminescent layer and with phosphorescent dopants, triplet exciton or hole are diffused into order to prevent
Hole barrier materials (HBL) are further laminated preferably by vacuum vapour deposition or spin-coating method in the phenomenon that electron transfer layer.At this time
Workable hole barrier substance is not particularly limited, and can be selected from the well known material as hole barrier materials any
It plants to use.For example,Oxadiazole derivative, triazole derivative, phenanthroline derivative or Japanese Unexamined Patent Publication 11-
Recorded hole barrier materials etc., can typically use Balq (bis- (8- hydroxy-2-methyl quinolines in 329734 (A1)
Quinoline)-xenol aluminium), phenanthroline (phenanthrolines) based compound is (for example, the BCP of UDC companies
(Bathocuproine, bathocuproine)) etc..
On luminescent layer top as formed above, electron transfer layer is formed, at this point, above-mentioned electron transfer layer passes through vacuum evaporation
The methods of method, spin-coating method, casting are formed, and are particularly preferably formed by vacuum vapour deposition.
Above-mentioned electron transport layer materials play the effect that will steadily be transmitted from electron injection electrode injected electrons, kind
Class is not particularly limited, and quinoline, especially three (8-hydroxyquinoline) aluminium (Alq can be used for example3) or ET4 (6,
6'- (3,4- bis-Base -1,1- dimethyl -1H- thiophenes cough up -2,5- diyls) two -2,2'- bipyridyls (6,6'- (3,4--
1,1--1H--2,5- )-2,2'-)).In addition, portion on the electron transport layer, it can
Has the function of substance, the i.e. electron injecting layer (EIL) for being easy to make electronics to be injected from cathode with stacking, as electron injecting layer object
Matter can utilize LiF, NaCl, CsF, Li2O, the substances such as BaO.
In addition, the evaporation condition of above-mentioned electron transfer layer is different according to used compound, but usually with hole
The interior selection of condition and range that the formation of implanted layer is almost the same is preferred.
Later, on above-mentioned electron transfer layer top, electron injecting layer substance can be formed, at this point, being passed about above-mentioned electronics
Defeated layer can form common electron injecting layer substance by the methods of vacuum vapour deposition, spin-coating method, casting, especially excellent
Vacuum vapour deposition was gated to be formed.
Finally, by the methods of vacuum vapour deposition or sputtering method, cathode formation metal is formed on electron injecting layer top,
To be used as cathode.Here, as cathode formation metal, the metal, alloy, electric conductivity with low work function can be used
Close object and their mixture.As concrete example, have lithium (Li), magnesium (Mg), aluminium (Al), aluminium-lithium (Al-Li), calcium (Ca),
Magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) etc..In addition, top light emitting element in order to obtain
The transmission-type cathode using ITO, IZO may be used.
The organic illuminating element of the present invention can not only realize anode, hole injection layer, hole transmission layer, luminescent layer, electricity
The organic illuminating element of sub- transport layer, electron injecting layer, cathode construction, and can realize the organic illuminating element of various structures
Structure, the middle layer of one or two layers can also be further formed as needed.
As described above, the thickness of each organic matter layer formed according to the present invention can be adjusted according to required degree,
Preferably 10 to 1000nm, more preferably 20 to 150nm.
In addition, the organic matter layer comprising the compound represented by above-mentioned chemical formula 1 of the present invention is due to can be with molecule list
Position adjusts the thickness of organic matter layer, therefore haves the advantages that surface is uniform, morphological stability is excellent.
The organic illuminating element of the present invention is due to comprising charge transfer excellent and with high triplet energy and high Tg
Chemical formula 1 indicate compound, so as to show low driving voltage, high efficiency, low power consumption, long-life.
Hereinafter, in order to help to understand the present invention, open preferred embodiment, but following embodiments only illustrate this hair
Bright, the scope of the present invention is not limited to following embodiments.
[synthesis of intermediate A 1]
[synthesis of A1-1]
In round-bottomed flask, the iodo- 2- nitrobenzenes 100g of dibenzo [b, d] furans -4- ylboronic acids 102.2g, 1- is dissolved in
The K of 600ml is added in toluene 1500ml2CO3Pd (the PPh of (2M) and 13.9g3)4, then carry out return stirring.Confirmed by TLC
Reaction, and water is added, then terminate reaction.After organic layer is extracted and is filtered under diminished pressure with EA, upper prop is refined, obtains 98.7g's
Intermediate A 1-1 (yield 85%).
[synthesis of A1]
The above-mentioned A1-1 of 98g is dissolved in 1,2- dichloro-benzenes 500ml, then adds the P (OEt) of 330ml3, and returned
Stream stirring.After organic layer is extracted and is filtered under diminished pressure with MC, upper prop is refined, obtains the intermediate A 1 (yield 60%) of 52.3g.
[synthesis of intermediate A 2]
[synthesis of A2-1]
In round-bottomed flask, the iodo- 2- nitrobenzenes 100g of dibenzo [b, d] thiophene -4- ylboronic acids 109.9g, 1- is dissolved in
The K of 600ml is added in toluene 1500ml2CO3Pd (the PPh of (2M) and 13.9g3)4, then carry out return stirring.Confirmed by TLC
Reaction, and water is added, then terminate reaction.After organic layer is extracted and is filtered under diminished pressure with EA, upper prop is refined, obtains 99.3g's
Intermediate A 2-1 (yield 81%).
[synthesis of A2]
The above-mentioned A2-1 of 99g is dissolved in 1,2- dichloro-benzenes 490ml, then adds the P (OEt) of 320ml3, and returned
Stream stirring.After organic layer is extracted and is filtered under diminished pressure with MC, upper prop is refined, obtains the intermediate A 2 (yield 61%) of 54.0g.
[synthesis of intermediate A 3]
[synthesis of A3-1]
In round-bottomed flask, the iodo- 2- nitrobenzenes 90g of (9- phenyl -9H- carbazole -1- bases) boric acid 124.53g, 1- are dissolved
In toluene 1500ml, the K of 540ml is added2CO3Pd (the PPh of (2M) and 12.5g3)4, then carry out return stirring.It is true by TLC
Recognize reaction, and add water, then terminates reaction.After organic layer is extracted and is filtered under diminished pressure with EA, upper prop is refined, obtains 105.4g
Intermediate A 3-1 (yield 80%).
[synthesis of A3]
The above-mentioned A3-1 of 105g is dissolved in 1,2- dichloro-benzenes 530ml, then adds the P (OEt) of 290ml3, and returned
Stream stirring.After organic layer is extracted and is filtered under diminished pressure with MC, upper prop is refined, obtains the intermediate A 3 (yield 41%) of 39.2g.
[synthesis of intermediate B 1]
[synthesis of B1-1]
In round-bottomed flask, the iodo- 2- nitrobenzenes 100g of benzofuran -3- ylboronic acids 78.5g, 1- is dissolved in toluene
The K of 600ml is added in 1000ml2CO3Pd (the PPh of (2M) and 13.9g3)4, then carry out return stirring.Confirmed by TLC anti-
It answers, and adds water, then terminate reaction.After organic layer is extracted and is filtered under diminished pressure with EA, upper prop is refined, obtains in 78.7g
Mesosome B1-1 (yield 82%).
[synthesis of B1]
The above-mentioned B1-1 of 78g is dissolved in 1,2- dichloro-benzenes 400ml, then adds the P (OEt) of 260ml3, and returned
Stream stirring.After organic layer is extracted and is filtered under diminished pressure with MC, upper prop is refined, obtains the intermediate B 1 (yield 54%) of 36.4g.
[synthesis of intermediate B 2]
[synthesis of B2-1]
In round-bottomed flask, the iodo- 2- nitrobenzenes 100g of benzo [b] thiene-3-yl boric acid 87.7g, 1- is dissolved in toluene
The K of 600ml is added in 1000ml2CO3Pd (the PPh of (2M) and 13.9g3)4, then carry out return stirring.Confirmed by TLC anti-
It answers, and adds water, then terminate reaction.After organic layer is extracted and is filtered under diminished pressure with EA, upper prop is refined, obtains the centre of 82g
Body B2-1 (yield 80%).
[synthesis of B2]
The above-mentioned B2-1 of 80g is dissolved in 1,2- dichloro-benzenes 400ml, then adds the P (OEt) of 310ml3, and returned
Stream stirring.After organic layer is extracted and is filtered under diminished pressure with MC, upper prop is refined, obtains the intermediate B 2 (yield 57%) of 39.8g.
[synthesis of intermediate B 3]
[synthesis of B3-1]
In round-bottomed flask, (1- phenyl -1H- indol-3-yls) iodo- 2- nitrobenzenes 90g of boric acid 102.8g, 1- is dissolved in
The K of 540ml is added in toluene 1000ml2CO3Pd (the PPh of (2M) and 12.5g3)4, then carry out return stirring.Confirmed by TLC
Reaction, and water is added, then terminate reaction.After organic layer is extracted and is filtered under diminished pressure with EA, upper prop is refined, obtains 93.1g's
Intermediate B 3-1 (yield 82%).
[synthesis of B3]
The above-mentioned B3-1 of 93g is dissolved in 1,2- dichloro-benzenes 460ml, then adds the P (OEt) of 290ml3, and returned
Stream stirring.After organic layer is extracted and is filtered under diminished pressure with MC, upper prop is refined, obtains the intermediate B 3 (yield 49%) of 40.9g.
[synthesis of intermediate B 6]
[synthesis of B6-1]
In round-bottomed flask, the iodo- 2- nitrobenzenes 100g of benzofuran -2- ylboronic acids 78.5g, 1- is dissolved in toluene
The K of 600ml is added in 1000ml2CO3Pd (the PPh of (2M) and 13.9g3)4, then carry out return stirring.Confirmed by TLC anti-
It answers, and adds water, then terminate reaction.After organic layer is extracted and is filtered under diminished pressure with EA, upper prop is refined, obtains in 81.6g
Mesosome B6-1 (yield 85%).
[synthesis of B6]
The above-mentioned B6-1 of 78g is dissolved in 1,2- dichloro-benzenes 410ml, then adds the P (OEt) of 330ml3, and returned
Stream stirring.After organic layer is extracted and is filtered under diminished pressure with MC, upper prop is refined, obtains intermediate 42.1g (yield 60%).
[synthesis of intermediate B 7]
[synthesis of B7-1]
In round-bottomed flask, the iodo- 2- nitrobenzenes 100g of benzo [b] thiophene -2- ylboronic acids 85.7g, 1- is dissolved in toluene
The K of 600ml is added in 1000ml2CO3Pd (the PPh of (2M) and 13.9g3)4, then carry out return stirring.Confirmed by TLC anti-
It answers, and adds water, then terminate reaction.After organic layer is extracted and is filtered under diminished pressure with EA, upper prop is refined, obtains in 80.9g
Mesosome B7-1 (yield 79%).
[synthesis of B7]
The above-mentioned B7-1 of 80g is dissolved in 1,2- dichloro-benzenes 400ml, then adds the P (OEt) of 310ml3, and returned
Stream stirring.After organic layer is extracted and is filtered under diminished pressure with MC, upper prop is refined, obtains the intermediate B 7 (yield 55%) of 38.5g.
[synthesis of intermediate B 8]
[synthesis of B8-1]
In round-bottomed flask, (1- phenyl -1H- indoles -2- bases) iodo- 2- nitrobenzenes 90g of boric acid 102.8g, 1- is dissolved in
The K of 540ml is added in toluene 1000ml2CO3Pd (the PPh of (2M) and 12.5g3)4, then carry out return stirring.Confirmed by TLC
Reaction, and water is added, then terminate reaction.After organic layer is extracted and is filtered under diminished pressure with EA, upper prop is refined, obtains 87.5g's
Intermediate B 8-1 (yield 77%).
[synthesis of B8]
The above-mentioned B8-1 of 87g is dissolved in 1,2- dichloro-benzenes 430ml, then adds the P (OEt) of 270ml3, and returned
Stream stirring.After organic layer is extracted and is filtered under diminished pressure with MC, upper prop is refined, obtains the intermediate B 8 (yield 33%) of 25.7g.
Using above-mentioned intermediate synthetic method, changes initial substance, synthesize following intermediates.
Embodiment 1：The synthesis of compound 1
By the bromo- 3- iodobenzenes of 1- of above-mentioned intermediate A3,4.1g of 4.0g, the Pd of t-BuONa, 0.45g of 1.7g2(dba)3、
(t-Bu) of 0.6ml3P is dissolved in toluene 60ml, then carries out return stirring.After confirming reaction terminating by TLC, by organic layer
It is extracted and is filtered under diminished pressure with MC, then upper prop is refined, obtains the intermediate 1-1 (yield 35%) of 2.05g.
By the intermediate B 1 of above-mentioned intermediate 1-1,2.05g of 2.05g, the Pd of t-BuONa, 0.15g of 0.61g2
(dba)3, 0.2ml (t-Bu)3P is dissolved in toluene 30ml, then carries out return stirring.It, will after confirming reaction terminating by TLC
Organic layer is extracted and is filtered under diminished pressure with MC, and then upper prop is refined, obtains the compound 1 (yield 52%) of 1.34g.
m/z：613.22 (100.0%), 614.22 (47.9%), 615.22 (11.8%), 616.23 (1.7%),
614.21 (1.1%)
Embodiment 2：The synthesis of compound 2
Intermediate A 3 is replaced using intermediate A 1, in addition to this, chemical combination is synthesized by method identical with compound 1
Object 2.
m/z：538.17 (100.0%), 539.17 (42.2%), 540.17 (8.9%), 541.18 (1.3%)
Embodiment 3：The synthesis of compound 3
Replace intermediate A 3 using intermediate A 2, intermediate B 1 replaced using intermediate B 2, in addition to this, by with
Compound 1 identical method synthesizes compound 3.
m/z：570.12 (100.0%), 571.13 (41.4%), 572.12 (9.4%), 572.13 (9.0%), 573.12
(3.9%), 571.12 (2.3%), 573.13 (1.3%)
Embodiment 4：The synthesis of compound 4
Intermediate B 1 is replaced using intermediate B 8, in addition to this, chemical combination is synthesized by method identical with compound 1
Object 4.
m/z：688.26 (100.0%), 689.27 (54.4%), 690.27 (14.5%), 691.27 (2.7%),
689.26 (1.5%)
Embodiment 5：The synthesis of compound 5
Intermediate B 1 is replaced using intermediate B 6, in addition to this, chemical combination is synthesized by method identical with compound 1
Object 5.
m/z：613.22 (100.0%), 614.22 (47.9%), 615.22 (11.8%), 616.23 (1.7%),
614.21 (1.1%)
Embodiment 6：The synthesis of compound 6
Intermediate B 1 is replaced using intermediate B 7, in addition to this, chemical combination is synthesized by method identical with compound 1
Object 6.
m/z：629.19 (100.0%), 630.20 (47.9%), 631.20 (11.6%), 631.19 (5.1%),
632.19 (2.2%), 630.19 (1.9%), 632.20 (1.9%)
Embodiment 7：The synthesis of compound 7
The NaH of above-mentioned intermediate A3,0.35g of 4.0g are put into DMF and the stirring of 40ml.It is slowly added dropwise thereto by 2,
Bis- chloro-6-phenyl -1,3,5- triazines 3.26g of 4- are dissolved in the solution after the DMF of 35ml.After stirring at normal temperature, confirmed by TLC
Reaction terminating carries out silica filtration, then recrystallizes, obtain the intermediate 7-1 (yield 43%) of 2.70g.
The NaH of above-mentioned intermediate B1,0.13g of 0.90g are put into DMF and the stirring of 10ml.Be slowly added dropwise thereto by
The intermediate 7-1 of 2.72g is dissolved in the solution after the DMF of 30ml.After stirring at normal temperature, reaction terminating is confirmed by TLC, is carried out
Then silica filtration recrystallizes, obtain the compound 7 (yield 52%) of 1.56g.
m/z：692.23 (100.0%), 693.24 (51.2%), 694.24 (13.0%), 695.24 (2.4%),
693.23 (2.2%), 694.23 (1.1%)
Embodiment 8：The synthesis of compound 8
Intermediate B 1 is replaced using intermediate B 2, in addition to this, chemical combination is synthesized by method identical with compound 7
Object 8.
m/z：708.21 (100.0%), 709.21 (53.9%), 710.22 (12.8%), 710.21 (6.1%),
711.21 (2.6%), 711.22 (2.2%)
Embodiment 9：The synthesis of compound 9
Intermediate A 3 is replaced using intermediate A 1, in addition to this, chemical combination is synthesized by method identical with compound 7
Object 9.
m/z：617.19 (100.0%), 618.19 (44.7%), 619.19 (11.0%), 618.18 (1.8%),
620.20 (1.4%)
Embodiment 10：The synthesis of compound 10
Replace intermediate A 3 using intermediate A 2, intermediate B 1 replaced using intermediate B 2, in addition to this, by with
Compound 7 identical method synthesizes compound 10.
m/z：649.14 (100.0%), 650.14 (47.8%), 651.14 (10.6%), 651.15 (9.7%),
652.14 (4.2%), 652.15 (1.5%)
*
Embodiment 11：The synthesis of compound 11
Intermediate A 3 is replaced using intermediate A 18, in addition to this, by method identical with compound 7 come synthesis
Close object 11.
m/z：692.23 (100.0%), 693.24 (51.2%), 694.24 (13.0%), 695.24 (2.4%),
693.23 (2.2%), 694.23 (1.1%)
Embodiment 12：The synthesis of compound 12
Intermediate A 3 is replaced using intermediate A 18, replaces intermediate B 1, in addition to this, pass through using intermediate B 2
Identical with compound 7 method synthesizes compound 12.
m/z：708.21 (100.0%), 709.21 (53.9%), 710.22 (12.8%), 710.21 (6.1%),
711.21 (2.6%), 711.22 (2.2%)
The manufacture of organic illuminating element
According to structure recorded in Fig. 1, organic illuminating element is manufactured.About organic illuminating element, stacked gradually from down
Anode12/ hole transmission layer of (hole injecting electrode 11)/hole injection layer, 13/ luminescent layer, 14/ electron transfer layer 15/
Cathode(electron injection electrode 16).
The hole injection layer 12 of embodiment and comparative example, hole transmission layer 13, luminescent layer 14, electron transfer layer 15 use
Following substance.
Embodiment 13
It will be withThickness thin film is coated with the glass substrate distilled water of tin indium oxide (ITO), ultrasonic cleaning.
After distilled water cleans, ultrasonic cleaning and drying are carried out with isopropanol, acetone, methanol equal solvent, be then transferred to etc. from
After sub- cleaning machine, after five minutes by aforesaid substrate cleaning thermal vacuum coating machine (thermal is utilized using oxygen plasma
Evaporator), portion on an ito substrate, manufacture hole injection layer HT01NPB as hole transmission layer
Film.Then, as luminescent layer, with 10% doping Ir (ppy) in above compound 13, manufactureFilm.Then, as
Electron transfer layer, with ET01：Liq(1：1) it manufactures Film after, manufacture LiFFilm, aluminium (Al)'s
The element is sealed (Encapsulation) by film in glove box, to make green organic illuminating element.
Embodiment 14 is to embodiment 24
By method identical with embodiment 13, make respectively using compound 2 to 12 as luminous layer main body system
The green organic illuminating element of film.
Comparative example 1
In addition to this compound 1 in luminous layer main body using CBP to replace above-described embodiment 1 passes through identical side
Method makes green organic illuminating element.
Comparative example 2
In addition to this passed through using the compound 1 in the luminous layer main body for comparing compound 1 to replace above-described embodiment 1
Identical method makes green organic illuminating element.
Comparative example 3
In addition to this passed through using the compound 1 in the luminous layer main body for comparing compound 2 to replace above-described embodiment 1
Identical method makes green organic illuminating element.
The performance evaluation of organic illuminating element
Apply voltage by 2400 digital sourcemeter of Keithley (Kiethley 2400source measurement unit),
Electrons and holes are injected, using Konica Minolta (Konica Minolta) spectroradiometer (CS-2000), measurement sends out light
When brightness, to being measured under atmospheric conditions for alive current density and brightness is applied, evaluating embodiment and being compared
The performance of the organic illuminating element of example, the results are shown in table 1.
Table 1
[table 1]
It confirms as shown in Table 1 above, the embodiment of the present invention is compared with comparative example 1 to 3, the object of organic illuminating element
Property in all respects on it is excellent.
INDUSTRIAL APPLICABILITY
The luminophor of the present invention is due to charge transfer excellent and has high triplet energy and high Tg, thus
Low driving voltage, high efficiency, low power consumption, long-life can be made it have when applied to organic illuminating element.
Claims (7)
1. the luminophor represented by a kind of following chemical formula 1：
Chemical formula 1
A-L-B
In above-mentioned formula,
A be following A 1 to the structure represented by A30 in one kind, wherein hydrogen included in A can each independently by deuterium,
Halogen, amino, itrile group, nitro substitution or unsubstituted,
L is by deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Alkenyl, C2-30Alkynyl, C1-30Alkoxy,
C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl6-50Aryl；Or by deuterium, halogen, ammonia
Base, itrile group, nitro, C1-30Alkyl, C2-30Alkenyl, C2-30Alkynyl, C1-30Alkoxy, C6-30Aryloxy group, C6-30's
Aryl or C2-30The substituted or unsubstituted C of heteroaryl2-50Heteroaryl,
B be following B1 to B10 represented by structure in one kind, wherein hydrogen included in B can each independently by deuterium,
Halogen, amino, itrile group, nitro substitution or unsubstituted,
In above structure ,-* is binding site, Ar1And Ar2It is each independently hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, nitro
Substituted or unsubstituted C1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkenyl；Quilt
The substituted or unsubstituted C of deuterium, halogen, amino, itrile group, nitro2-30Alkynyl；Replaced by deuterium, halogen, amino, itrile group, nitro or
Unsubstituted C1-30Alkoxy；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryloxy group；By deuterium,
The substituted or unsubstituted C of halogen, amino, itrile group, nitro6-30Aryl；Or replaced by deuterium, halogen, amino, itrile group, nitro
Or unsubstituted C2-30Heteroaryl.
2. the luminophor indicated by any of following chemical formula：
In above-mentioned formula, X1And X2It is each independently S, O, Se, Te or N-Ar3, wherein Ar3For hydrogen；Deuterium；By deuterium, halogen, amino,
The substituted or unsubstituted C of itrile group, nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30's
Alkenyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, nitre
The substituted or unsubstituted C of base1-30Alkoxy；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Fragrant oxygen
Base；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryl；Or by deuterium, halogen, amino, itrile group,
The substituted or unsubstituted C of nitro2-30Heteroaryl,
Ar is by deuterium, halogen, amino, itrile group, nitro, C1-30Alkyl, C2-30Alkenyl, C2-30Alkynyl, C1-30Alkoxy,
C6-30Aryloxy group, C6-30Aryl or C2-30The substituted or unsubstituted C of heteroaryl6-50Aryl；Or by deuterium, halogen, ammonia
Base, itrile group, nitro, C1-30Alkyl, C2-30Alkenyl, C2-30Alkynyl, C1-30Alkoxy, C6-30Aryloxy group, C6-30's
Aryl or C2-30The substituted or unsubstituted C of heteroaryl6-50Heteroaryl.
3. the luminophor indicated by any of following chemical formula：
In above-mentioned formula, X1And X2It is each independently S, O, Se, Te or N-Ar4, wherein Ar4For hydrogen；Deuterium；By deuterium, halogen, amino,
The substituted or unsubstituted C of itrile group, nitro1-30Alkyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30's
Alkenyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkynyl；By deuterium, halogen, amino, itrile group, nitre
The substituted or unsubstituted C of base1-30Alkoxy；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Fragrant oxygen
Base；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro6-30Aryl；Or by deuterium, halogen, amino, itrile group,
The substituted or unsubstituted C of nitro2-30Heteroaryl,
Y is CR1Or N, wherein R1For hydrogen；Deuterium；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkyl；
By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Alkenyl；Replaced by deuterium, halogen, amino, itrile group, nitro
Or unsubstituted C2-30Alkynyl；By deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro1-30Alkoxy；By deuterium,
The substituted or unsubstituted C of halogen, amino, itrile group, nitro6-30Aryloxy group；Replaced by deuterium, halogen, amino, itrile group, nitro or
Unsubstituted C6-30Aryl；Or by deuterium, halogen, amino, itrile group, the substituted or unsubstituted C of nitro2-30Heteroaryl.
4. luminophor according to claim 1, which is characterized in that the L is indicated by any one of following structures：
5. luminophor according to claim 1, which is characterized in that indicated by any of following chemical formula：
6. a kind of organic illuminating element, it includes anode, cathode and between two electrodes containing described in claim 1
One layer or more of organic matter layer of compound.
7. organic illuminating element according to claim 6, which is characterized in that the organic matter layer contains claim 1 institute
The compound stated is as light emitting host or dopant.
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| WO2012016630A1 (en) * | 2010-08-05 | 2012-02-09 | Merck Patent Gmbh | Materials for electronic devices |
| JP2013058560A (en) * | 2011-09-07 | 2013-03-28 | Konica Minolta Holdings Inc | Organic electroluminescent element material, organic electroluminescent element, display apparatus, illuminating apparatus and compound |
| CN103154005A (en) * | 2010-10-13 | 2013-06-12 | 新日铁住金化学株式会社 | Nitrogenated aromatic compound, organic semiconductor material, and organic electronic device |
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| WO2012016630A1 (en) * | 2010-08-05 | 2012-02-09 | Merck Patent Gmbh | Materials for electronic devices |
| CN103154005A (en) * | 2010-10-13 | 2013-06-12 | 新日铁住金化学株式会社 | Nitrogenated aromatic compound, organic semiconductor material, and organic electronic device |
| JP2013058560A (en) * | 2011-09-07 | 2013-03-28 | Konica Minolta Holdings Inc | Organic electroluminescent element material, organic electroluminescent element, display apparatus, illuminating apparatus and compound |
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