CN109608503A - Metal complex, electroluminescent organic material, organic electroluminescence device - Google Patents
Metal complex, electroluminescent organic material, organic electroluminescence device Download PDFInfo
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- CN109608503A CN109608503A CN201811574254.9A CN201811574254A CN109608503A CN 109608503 A CN109608503 A CN 109608503A CN 201811574254 A CN201811574254 A CN 201811574254A CN 109608503 A CN109608503 A CN 109608503A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Abstract
A kind of organic electroluminescence device the invention discloses metal complex and comprising the metal complex, electroluminescent organic material.The molecular formula of metal complex of the invention is M (LA)x(LB)y(Lc)z；Metal complex electroluminescent device proposed by the present invention shines as peony, and external quantum efficiency is high, while the thermal stability of material is good, and material is easily prepared, is easily purified, and is the ideal chose as organic electroluminescence device luminescent material.
Description
Technical field
The present invention relates to technical field of organic electroluminescence.More particularly, to using having for organic red phosphor material
Organic electro luminescent technical field.
Background technique
Electroluminescent organic material is divided into two major classes: organic electroluminescent fluorescent materials and organic electromechanical phosphorescent material.Organic
In electromechanical phosphorescent material, organic electroluminescence green phosphorescent material is studied earliest, and a kind of material that development is most mature.
The mode of the spin coating such as Hino in 2004 has made phosphorescent devices, and external quantum efficiency is up to 29cd/A.Adachi etc. is by (ppy)
2Ir (acac) is doped in TAZ, and using HMTPD as hole transmission layer, obtaining maximum external quantum efficiency is 20%, can dose-effect
Rate is the green device of 65lm/W.
But feux rouges phosphor material still has the problem that luminous quantum efficiency is low, stability is poor at present.Cause this shape
The main reason for condition is that have between ligand very by force because there is the interaction of stronger pi-pi bond in the system of red light material
Charge transfer characteristic exacerbate being quenched for phosphor to make the presence of more radiationless relaxation channels in narrow band gap, reduce
The quantum yield of feux rouges system.Therefore the red phosphorescence material that design synthesis luminous quantum efficiency is high, has good stability, will be at
For the important topic of electroluminescent organic material research.
Summary of the invention
In order to solve the technical problems existing in the prior art, present inventor etc. is conducted in-depth research, knot
Fruit has found that the electroluminescent of metal complex of the invention is peony and the high phosphor material of external quantum efficiency, to complete
The present invention.
It is an advantage of the invention to provide a kind of metal complexs that electroluminescent external quantum efficiency is excellent.
Second object of the present invention is to provide a kind of organic electroluminescence material comprising metal complex of the invention
Material.
Yet another object of the invention is that providing a kind of organic luminous layer includes one in metal complex of the invention
Kind or a variety of organic electroluminescence devices.
In order to achieve the above objectives, the present invention adopts the following technical solutions:
The first aspect of the present invention provides a kind of metal complex, the molecular formula of the metal complex are as follows:
M(LA)x(LB)y(Lc)z
Wherein M indicates the metallic element that atomic weight is greater than 40；X indicates integer 1,2 or 3；Y indicates integer 0,1 or 2；Z is indicated
Integer 0,1 or 2；And the sum of x, y, z is equal to the oxidation state of metal M；
LAThe group of the structure composition shown in Formulas I, the Formula II:
R1、R2、R3、R4、R41、R42、R43、R44It is each independently selected from hydrogen atom, D-atom, halogen atom, alkyl group, cycloalkanes
Base, the miscellaneous alkyl containing nitrogen, oxygen, sulphur, silicon, germanium or phosphorus atoms, aralkyl, alkoxy, aryloxy group, amino, alkenyl, cyclenes
Base, miscellaneous thiazolinyl, alkynyl, aryl, heterocyclic aryl, acyl group, carbonyl, carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulfonyl, Asia
The group of sulfonyl, phosphino-, phosphine oxygroup composition；Adjacent substituents optionally engage or are fused into five-membered ring, hexatomic ring in Formulas I, Formula II
Or it is polycyclic；X1It is each independently selected from carbon or nitrogen；R in Formulas I, Formula II4Number be each independently 1~4；
LBAre as follows:
R5、R6Be each independently selected from hydrogen atom, D-atom, halogen atom, alkyl group, naphthenic base, containing nitrogen, oxygen, sulphur, silicon,
The miscellaneous alkyl of germanium or phosphorus atoms, aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl, miscellaneous thiazolinyl, alkynes
Base, aryl, heterocyclic aryl, acyl group, carbonyl, carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulfonyl, sulfinyl, phosphino-,
The group of phosphine oxygroup composition；Formula LBMiddle adjacent substituents optionally engage or are fused into five-membered ring, hexatomic ring or polycyclic；Ring C, ring D
It is each independently selected from five yuan of carbocyclic rings, six-membered carbon ring, five-ring heterocycles or hexa-member heterocycle；Substituent R on ring C, ring D5、R6It is one
It is a or two or more；X2For carbon or nitrogen；
LCAre as follows:
R7、R8、R9Be each independently selected from hydrogen atom, D-atom, halogen atom, alkyl group, naphthenic base, containing nitrogen, oxygen, sulphur,
Silicon, the miscellaneous alkyl of germanium or phosphorus atoms, aralkyl, alkoxy, aryloxy group, amino, alkenyl, cycloalkenyl, miscellaneous thiazolinyl, alkynyl, virtue
Base, heterocyclic aryl, acyl group, carbonyl, carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulfonyl, sulfinyl, phosphino-, phosphine oxygen
The group of base composition；R7、R8、R9Middle adjacent substituents optionally engage or are fused into five-membered ring, hexatomic ring or polycyclic.
The second aspect of the present invention provides a kind of electroluminescent organic material, contains metal combination of the invention above-mentioned
Object.
The third aspect of the present invention provides a kind of organic electroluminescence device, with organic luminous layer, organic hair
Photosphere includes one of metal complex of the invention above-mentioned or a variety of.
Formula M (the L of metal complex of the inventionA)x(LB)y(Lc)zShown in structure be acenaphthene or acenaphthene with condensed cyclic structure
The metal complex of alkenyl quinoline is electroluminescent phosphorescence luminescent material, and electroluminescent is peony, and external quantum efficiency is high.Separately
Outside, the thermal stability of metallic compound of the invention is good, and material easily prepared, easy sublimation purification, before having boundless market
Scape.
Electroluminescent organic material of the invention can obtain external quantum efficiency by containing metal complex of the invention
High red phosphorescence material.In addition, the thermal stability of electroluminescent organic material of the invention is good.
Organic electroluminescence device of the invention, can by containing metal complex of the invention in organic luminous layer
Obtain the organic electroluminescence device that electroluminescent is red phosphorescent and external quantum efficiency improves.In addition, Organic Electricity of the invention
The thermal stability of electroluminescence device is good.
Detailed description of the invention
Fig. 1 shows the structural schematic diagram of the electroluminescent device of one embodiment of the present of invention.
Description of symbols
In Fig. 1,1- substrate, 2- anode layer, 3- hole injection layer, 4- hole transmission layer, 5 organic luminous layers, 6- electronics are passed
Defeated layer, 7- cathode layer.
Specific embodiment
The existing various exemplary embodiment that the present invention will be described in detail, the detailed description are not considered as to limit of the invention
System, and it is understood as the more detailed description to certain aspects of the invention, characteristic and embodiment.
It should be understood that it is to describe special embodiment that heretofore described term, which is only, it is not intended to limit this hair
It is bright.In addition, for the numberical range in the present invention, it is thus understood that specifically disclose the range upper and lower bound and they it
Between each median.Median and any other statement value in any statement value or stated ranges or in the range
Lesser range is also included in the present invention each of between interior median.These small range of upper and lower bounds can be independent
Ground includes or excludes in range.
Unless otherwise stated, all technical and scientific terms used herein has the routine in field of the present invention
The normally understood identical meanings of technical staff.Although the present invention only describes preferred method and material, of the invention
Implement or also can be used and similar or equivalent any method and material described herein in testing.The institute mentioned in this specification
There is document to be incorporated by reference into, to disclosure and description method relevant to the document and/or material.It is incorporated to any
When document conflicts, it is subject to the content of this specification.Unless otherwise stated, " % " is the percentage based on weight.
" external quantum efficiency " in the present invention refers to, metal complex or electroluminescent material emit in electroluminescent
The ratio between number of photons out and injected electrons number.
[metal complex]
The molecular formula of metal complex of the invention are as follows:
M(LA)x(LB)y(Lc)z
Wherein, M indicates the metallic element that atomic weight is greater than 40；
X indicates integer 1,2 or 3；Y indicates integer 0,1 or 2；Z indicates integer 0,1 or 2；And x, y, z and be equal to metal
The oxidation state of M；
LAThe group of the structure composition shown in Formulas I, the Formula II:
R1、R2、R3、R4、R41、R42、R43、R44It is each independently selected from hydrogen atom, D-atom, halogen atom, alkyl group, cycloalkanes
Base, the miscellaneous alkyl containing nitrogen, oxygen, sulphur, silicon, germanium or phosphorus atoms, aralkyl, alkoxy, aryloxy group, amino, alkenyl, cyclenes
Base, miscellaneous thiazolinyl, alkynyl, aryl, heterocyclic aryl, acyl group, carbonyl, carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulfonyl, Asia
The group of sulfonyl, phosphino-, phosphine oxygroup composition；R1、R2、R3、R4、R41、R42、R43、R44Middle adjacent substituents are optionally engaged or are condensed
At five-membered ring, hexatomic ring or polycyclic；X1For carbon or nitrogen；R in Formulas I, Formula II4Number be each independently 1~4；
LBAre as follows:
R5、R6Be each independently selected from hydrogen atom, D-atom, halogen atom, alkyl group, naphthenic base, containing nitrogen, oxygen, sulphur, silicon,
The miscellaneous alkyl of germanium or phosphorus atoms, aralkyl, alkoxy, aryloxy group, amino, alkenyl, cycloalkenyl, miscellaneous thiazolinyl, alkynyl, aryl,
Heterocyclic aryl, acyl group, carbonyl, carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulfonyl, sulfinyl, phosphino-, phosphine oxygroup group
At group；Formula LBMiddle adjacent substituents optionally engage or are fused into five-membered ring, hexatomic ring or polycyclic；Ring C, ring D are respectively independent
Ground is selected from five yuan of carbocyclic rings, six-membered carbon ring, five-ring heterocycles or hexa-member heterocycle；Substituent R on ring C, ring D5、R6For one or two
More than a；X2For carbon or nitrogen；
LCAre as follows:
R7、R8、R9Be each independently selected from hydrogen atom, D-atom, halogen atom, alkyl group, naphthenic base, containing nitrogen, oxygen, sulphur,
Silicon, the miscellaneous alkyl of germanium or phosphorus atoms, aralkyl, alkoxy, aryloxy group, amino, silylation, alkenyl, cycloalkenyl, miscellaneous thiazolinyl,
Alkynyl, aryl, heterocyclic aryl, acyl group, carbonyl, carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulfonyl, sulfinyl, phosphine
The group of base, phosphine oxygroup composition；R7、R8、R9Middle adjacent substituents optionally engage or are fused into five-membered ring, hexatomic ring or polycyclic.
As metal M, such as Ir, Pt can be enumerated.About the oxidation state of metal M, when M is Ir, the oxidation of Ir
Valence state can be 3, and when M is Pt, the oxidation state of Pt can be 2,4,6.
Metal complex of the invention is preferably with Ir (LA)(LB)(Lc)、Ir(LA)2(LB)、Ir(LA)2(Lc)、Ir
(LA)3、Pt(LA)(LB)、Pt(LA)(LC) indicate compound, wherein LA、LB、LcDefinition as hereinbefore.
In metal complex of the invention, chemical formula M (LA)x(LB)y(Lc)zMiddle LAStructure be preferably selected from following formula
The group of structure composition shown in III, formula IV:
In formula III, formula IV, R1、R2、R3、R4、R41、R42、R43、R44It is former to be each independently selected from hydrogen atom, D-atom, halogen
Son, alkyl, naphthenic base, the miscellaneous alkyl containing nitrogen, oxygen, sulphur, silicon, germanium or phosphorus atoms, aralkyl, alkoxy, aryloxy group, amino,
Alkenyl, cycloalkenyl, miscellaneous thiazolinyl, alkynyl, aryl, heterocyclic aryl, nitrogenous, germanium, oxygen or the aliphatic group of sulphur, phosphino-, phosphine oxygroup
The group of composition；Wherein R1、R2、R3、R4、R41、R42、R43、R44In optionally engage or be fused between adjacent group five-membered ring,
Hexatomic ring is polycyclic.
Preferably, the chemical formula M (L of metal complex of the inventionA)x(LB)y(Lc)zMiddle LAStructural formula it is chosen from the followings
The group of formula III, formula IV compound represented composition:
In formula III, formula IV, R1、R2、R3、R41、R42、R43、R44、R4It is each independently selected from RA1~RA56And RB1~RB45
Composed group,
RA1~RA56Shown structural formula is as follows:
RB1~RB45Shown structural formula is as follows:
The group of the composition of structural formula shown in LA1~LA1912 of the formula III above-mentioned further preferably in following table:
Formula IV above-mentioned is further preferably selected from the group of the composition of structural formula shown in LA1913~LA3482 of following table:
RA3、RA27、RA34Shown structural formula is as follows:
RB1To RB45Shown structural formula is as follows:
In metal complex of the invention, it is further preferred that chemical formula M (LA)x(LB)y(Lc)zMiddle LBStructural formula choosing
The group formed from following structural formula:
Wherein Ra、Rb、Rc、RdIt is each independently selected from the group being made of following group: hydrogen, deuterium hydrogen, halogen, alkyl group, ring
Alkyl, the miscellaneous alkyl containing nitrogen, oxygen, sulphur, silicon, germanium or phosphorus atoms, aralkyl, alkoxy, aryloxy group, amido, alkenyl, cyclenes
Base, miscellaneous thiazolinyl, alkynyl, aryl, heteroaryl, acyl group, carbonyl, carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulfinyl, sulphur
Acyl group, phosphorus base；Wherein Ra、Rb、Rc、RdMiddle any two adjacent substituents are optionally condensed or engage and form ring or formed more
Tooth ligand.
For L above-mentionedB, it is further preferred that, the LBGroup selected from following LB1~LB36 composition:
In metal complex of the invention, it is preferable that structural formula LCSelected from the composition of structural formula shown in following LC1~LC46
Group:
In metal complex of the invention, it is preferable that the molecular formula of the metal complex is Ir (LAi) (LBj)
(LCw)、Ir(LAi)2(LBj)、Ir(LAi)3、Ir(LAi)2(LCw), Pt (LAi) (LBj) or Pt (LAi) (LCw)；
The wherein integer that i is 1~3482, the integer that j is 1~36, and the integer that w is 1~46.
[electroluminescent organic material]
It include one of metal complex of the invention or a variety of in electroluminescent organic material of the invention.The present invention
Electroluminescent organic material can also contain the present invention only by one or more formation of metal complex of the invention
Metal complex except other materials.
By containing metal complex of the invention above-mentioned in electroluminescent organic material of the invention, can obtain
Electroluminescent is peony, the high electroluminescent organic material of external quantum efficiency.In addition, electroluminescent organic material of the invention
For the good electroluminescent organic material of thermal stability.
[organic electroluminescence device]
Organic electroluminescence device of the invention has organic luminous layer, and the organic luminous layer includes the above-mentioned present invention
One of metal complex or a variety of.
In organic electroluminescence device of the invention, the metal complex of the invention for including in aforementioned organic luminous layer can
To be to be doped in the material to shine in material of main part, it is also possible to undoped luminous material.It specifically, can in organic luminous layer
Using small molecule material as the further doping fluorescent material of material of main part or phosphorescent coloring.The material of organic luminous layer above-mentioned
In to may include metal complex of the invention shine in corresponding material of main part as phosphorescence dopant material.As above-mentioned
The material of main part that may include in organic luminous layer, such as can enumerate selected from one of following compound or a variety of.
[electroluminescent organic material]
It include one of metal complex of the invention or a variety of in electroluminescent organic material of the invention.The present invention
Electroluminescent organic material can also contain the present invention only by one or more formation of metal complex of the invention
Metal complex except other materials.
By containing metal complex of the invention above-mentioned in electroluminescent organic material of the invention, can obtain
Electroluminescent is peony, the high electroluminescent organic material of external quantum efficiency.In addition, electroluminescent organic material of the invention
For the good electroluminescent organic material of thermal stability.
[organic electroluminescence device]
Organic electroluminescence device of the invention has organic luminous layer, and the organic luminous layer includes the above-mentioned present invention
One of metal complex or a variety of.
In organic electroluminescence device of the invention, the metal complex of the invention for including in aforementioned organic luminous layer can
To be to be doped in the material to shine in material of main part, it is also possible to undoped luminous material.It specifically, can in organic luminous layer
Using small molecule material as the further doping fluorescent material of material of main part or phosphorescent coloring.The material of organic luminous layer above-mentioned
In to may include metal complex of the invention shine in corresponding material of main part as phosphorescence dopant material.As above-mentioned
The material of main part that may include in organic luminous layer, such as can enumerate selected from one of following compound or a variety of.
Embodiment
In the following embodiment of the present invention, it is then all made of conventional preparation method unless otherwise specified.Raw material used is such as
It can be obtained from disclosed commercial sources without illustrating, the percentage is mass percent unless otherwise specified.
A series of new metal complex provided by the invention, preparation method are all under the conditions of well-known be suitble to
Carry out, some be related to simple organic preparation, such as the preparation of phenyl boronic acid derivative etc. be those skilled in the art according to
What the operative skill of its this field was synthesized, it is not described in the present invention.
Following abbreviation has been used in embodiments of the present invention:
Table 1: abbreviation and full name
| Abbreviation | Full name |
| THF | Tetrahydrofuran |
| n-BuLi | Positive group lithium |
| NBS | N-bromosuccinimide |
| (PinB)2 | Connection boric acid pinacol ester |
| Pd(PPh3)4 | Tetrakis triphenylphosphine palladium |
| dppf | Bis- (diphenylphosphine) ferrocene of 1,1'- |
(preparation of precursor)
Embodiment 1
The preparation of the ligand of structure shown in formula LA314:
The preparation method of ligand L A314, includes the following steps:
Step 1: the preparation of compound Int-1
5.1g (30.5mmol) chloraldurate is dispersed in 100mL water, 35.1g (247.1mmol) anhydrous slufuric acid is added
Sodium, oil bath heating to 35 DEG C, stirring and dissolving are added at one time 4.7g (27.7mmol) 1- aminoidan hydrochloride, 6.1g
The hydroxylamine hydrochloride of (88.1mmol) and the mixed solution of 30mL water, are warming up to 90 DEG C, after being stirred to react 8 hours, are cooled to room temperature,
Filtering, filter cake are washed with water, dry, obtain 4.7g yellow solid.
Aforementioned obtained yellow solid is added in 60 DEG C of 86% sulfuric acid of 50mL, temperature control is at 60~65 DEG C, stirring
Reaction 30 minutes, is warming up to 80 DEG C, is stirred to react 30 minutes, is cooled to room temperature, reaction solution is poured into the ice water of 500mL, mistake
Filter, filter cake are washed with water, dry, obtain the compound Int.-1 that 2.3g is in yellow solid.
Step 2: the preparation of compound Int-2
Under nitrogen protection, titanium tetrachloride 7mL (60.0mmol) is slowly dropped to 150mL dry THF and 7.8g
In (120.0mmol) zinc powder mixture, heating reflux reaction 2 hours, it is cooled to room temperature, it is aforementioned to be added dropwise to 3.7g (20.0mmol)
The intermediate compound I nt.-1 that the first step is prepared is dissolved in the solution of 20mL dry THF, and reaction 1 hour is stirred at room temperature, is added dropwise to 3N
Dilute hydrochloric acid quenching reaction, be stirred to react 30 minutes, water phase is extracted with dichloromethane, and dries, filters, and filtrate decompression concentration is dry,
With silica gel column separating purification, the intermediate compound I nt.-2 that 3.1g is in yellow solid is obtained.
Step 3: the preparation of compound Int-3
Into 250mL reaction flask, investment 3.0g (17.3mmol) intermediate compound I nt.-2,50mL dimethyl sulfoxide above-mentioned and
2.2g (8.6mmol) iodine adds 30% hydrogen peroxide of 2.0g (17.3mmol), is warming up to 60 DEG C, is stirred to react 1 hour, directly
It connects and pours into ice water, filter, obtain yellow solid, after being dried under reduced pressure, 20mL phosphorus oxychloride is added, it is back flow reaction 2 hours, cooling
It to room temperature, is concentrated under reduced pressure and does, trash ice is added and stirs 30 minutes, is extracted with dichloromethane, collects organic phase, filters, drying, filtrate
It is concentrated under reduced pressure and does, obtain 2.5g intermediate compound I nt.-3, dark brown grease obtains 1.8g intermediate with silica gel column separating purification
Int.-3, yellow oil.
Step 4: the preparation of compound L A314
Intermediate compound I nt.-3 and the 50mL toluene being prepared will be walked on 1.5g (7.9mmol) is added to 1.4g
(9.5mmol) 3,5- dimethylphenyl boronic acid, 3.4g (31.6mmol) natrium carbonicum calcinatum and 0.4mg catalyst Pd (PPh3)4In, then
20mL ethyl alcohol and 10mL water is added, temperature rising reflux reacts 8 hours, is cooled to room temperature, is extracted with ethyl acetate, organic phase is collected,
It dries, filters, filtrate concentration is dry, with silica gel column separating purification, obtains the ligand compound of structure shown in 1.2g formula LA314, yellow
Color grease.
Embodiment 2
The preparation of compound L A1~LA313, LA315~LA563, LA787~LA1912, referring to the preparation side of embodiment 1
Method will by the 1- aminoidan hydrochloride of the first step in the 1- aminoidan hydrochloride alternative embodiment 1 with different substituents
3, the 5- dimethylphenyl boronic acid of 4th step in phenyl boric acid alternative embodiment 1 with different substituents prepares the LA1 in ligand L A
~LA313, LA315~LA563 and LA787~LA1912.
Embodiment 3
The preparation of the ligand of structure shown in formula LA697:
Into stand up reaction bottle, 5.0g (19.3mmol) LA314 is put into, the deuterated ethyl alcohol of 20mL is added, adds 5g
(73.5mmol) sodium ethoxide, temperature rising reflux react 12 hours, are cooled to room temperature, are concentrated under reduced pressure and do, with silica gel column separating purification, obtain
To ligand compound shown in 4.8g formula LA697, white solid.
Embodiment 4
The preparation of compound L A564~LA696, LA698~LA786, will corresponding non-deuteriums referring to the preparation method of embodiment 3
It is prepared by the LA314 in the raw material alternative embodiment 3 in generation.
Embodiment 5
The preparation of the ligand of structure shown in formula LA2226:
The preparation method of ligand L A2226, includes the following steps:
Into reaction flask, 3.0g (17.3mmol) LA314,100mL dimethylbenzene and 3.0g5% palladium/carbon, temperature rising reflux are put into
It is stirred to react 24 hours, is cooled to room temperature, filter, filtrate decompression concentration is dry, with silica gel column separating purification, obtains 2.6g formula
Compound shown in LA2226, yellow oil.
Embodiment 6
LA1913~LA2225, LA2227~LA2475, structure shown in LA2698~LA3260 ligand preparation method
Referring to embodiment 5, by the bromo- 1- indane of 7- of the first step in the bromo- 1- indone alternative embodiment 5 of 7- with different substituents
Ketone is prepared 3, the 5- dimethyl bromobenzene of the 4th step in bromobenzene or bromobenzene alternative embodiment 5 with different substituents.
Embodiment 7
The preparation of the ligand compound of structure shown in formula LA2608:
Into stand up reaction bottle, 5.0g (19.4mmol) LA2226 is put into, the deuterated ethyl alcohol of 20mL is added, adds 5g
(73.5mmol) sodium ethoxide, temperature rising reflux react 12 hours, are cooled to room temperature, are concentrated under reduced pressure and do, with silica gel column separating purification, obtain
The ligand of structure shown in 4.4g formula LA2608, yellow solid.
Embodiment 8
The preparation of compound L A2476~LA2607, LA2609~LA2697, LA3261~LA3482, referring to embodiment 7
Preparation method, by the LA2226 in corresponding non-deuterated raw material alternative embodiment 7, prepare LA2476 in ligand L A~
LA2607, LA2609~LA2697, LA3261~LA3482.
Embodiment 9
Compound Ir (LA314)2(LC5) preparation:
Metal complex Ir (LA314)2(LC5) preparation method, includes the following steps:
Step 1: the preparation of compound Int-4
By 2.1g compound L A314 and 1.4gIrCl3·3H2O is dispersed in 48ml ethylene glycol ethyl ether and 16ml water, in nitrogen
Under gas shielded, temperature rising reflux reacts 24 hours, is cooled to room temperature, filters, and filter cake is washed with water, and is dried in vacuo, obtains 1.8g chemical combination
Object Int-4, red solid.
Step 2: compound Ir (LA314)2(LC5) preparation
By compound Int-4 and 715mg3,7- the diethyl nonane -4,6- diketone of 2.0g aforementioned first step preparation and
1.42g natrium carbonicum calcinatum is dispersed in 40ml acetonitrile and 40ml chloroform, and under nitrogen protection, temperature rising reflux reacts 24 hours, cold
But room temperature is arrived, reaction solution is poured into water, is extracted with dichloromethane, organic phase dries, filters, and filtrate decompression concentration is dry, remaining
Object obtains 1.3g compound Ir (LA314) through silica gel column separating purification2(LC5), red solid.
Embodiment 10
Compound Ir (LA2226)2(LC11) preparation:
Metal complex Ir (LA2226)2(LC11) preparation method, includes the following steps:
Step 1: the preparation of compound Int-5
By 2.0g compound L A2226 and 1.4gIrCl3·3H2O is dispersed in 48ml ethylene glycol ethyl ether and 16ml water, in nitrogen
Under gas shielded, temperature rising reflux reacts 24 hours, is cooled to room temperature, filters, and filter cake is washed with water, and is dried in vacuo, obtains 2.2g chemical combination
Object Int-5, red solid.
Step 2: compound Ir (LA2226)2(LC11) preparation
By compound Int-5 and 622mg2,8- dimethylnonane -4,6- diketone made from the aforementioned first step of 2.0g and
1.43g natrium carbonicum calcinatum is dispersed in the chloroform of 40ml acetonitrile and 40ml, and under nitrogen protection, temperature rising reflux reacts 24 hours,
It is cooled to room temperature, reaction solution is poured into water, is extracted with dichloromethane, organic phase dries, filters, and filtrate decompression concentration is dry, residual
Excess obtains 1.6g compound Ir (LA2226) through silica gel column separating purification2(LC11), red solid.
Embodiment 11
Referring to embodiment 9 and embodiment 10, prepare compound: Ir (LAq)2(LCw), the integer that q is 1~3482, w 1
~46 integer.
Embodiment 12
The preparation of compound Ir (LA314) (LB69) (LC5):
The preparation method of metal complex Ir (LA314) (LB69) (LC5), includes the following steps:
Step 1: the preparation of compound Int-6
340.8mg1- phenyl -1H- imidazoles iodomethane salt and 139.5mg silver oxide are dispersed in 20mL methylene chloride, added
Enter 400mg4A molecular sieve, reaction 2 hours is stirred at room temperature, is added 1.4g [IrCl (COD)]2, it is stirred to react 2 hours, filters,
Filter cake is washed with methylene chloride, and dry, addition 50mL n-hexane, filtering is concentrated under reduced pressure, and vacuum drying obtains 0.5g compound Int-6,
Yellow solid.
Step 2: the preparation of compound Ir (LA314) (LB69) (LC5)
Compound Int-6 and 262mg (1.01mmol) LA314 the and 50mL methanol of the aforementioned first step preparation of 0.5g is mixed
It closes, under nitrogen protection, temperature rising reflux reacts 5 days, is cooled to room temperature, filters, and filter cake is washed with methanol, obtains red solid.
Obtained red solid and 214mg3,7- diethyl nonane -4,6- diketone and 97mg sodium tert-butoxide are dispersed in
In the anhydrous THF of 40ml, under nitrogen protection, temperature rising reflux reacts 1 hour, is cooled to room temperature, is concentrated under reduced pressure and does, residue is through silicon
Rubber column gel column isolates and purifies, and obtains 340mg compound Ir (LA314) (LB69) (LC5), red solid.
Embodiment 13
Referring to embodiment 12, the compound of the present invention: Ir (LAi) (LBj) (LCw) is prepared；Wherein i be 1~3482 it is whole
Number, the integer that j is 1~36, and the integer that w is 1~46；
(preparation of organic electroluminescence device)
Embodiment 14
The glass substrate for being coated with ITO conductive layer is ultrasonically treated 30 minutes in cleaning agent, is rinsed in deionized water,
At acetone/ethanol in the mixed solvent ultrasound 30 minutes, it is baked to is completely dried under a clean environment, shone with ultraviolet rays cleaning machine
It penetrates 10 minutes, and with low energy cation beam bombarded surface.
The above-mentioned ito glass substrate handled well is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, upper
It states and continues to be deposited compound DNTPD on anode tunic respectively as hole injection layer, film thickness is deposited in evaporation rate 0.1nm/s
For 40nm；Continue that NPD is deposited on above-mentioned hole injection layer film to be hole transmission layer, film thickness is deposited in evaporation rate 0.1nm/s
For 10nm；
Evaporation metal complex (" metal complex " arranges in aftermentioned table 2) and TDC make in foregoing hole transport layer
For the organic luminous layer of device, wherein material based on TDC, metal complex of the invention be dopant material, dopant material with
The evaporation rate ratio of TDC is 1:100, and doping concentration is the value recorded in the bracket of " metal complex " column in aftermentioned table 2, is steamed
Plating total rate is 0.1nm/s, and vapor deposition film thickness is 50nm；
Electron transfer layer of the one layer of LiQ material of vapor deposition as device is further continued on above-mentioned organic luminous layer, plating rate is
0.1nm/s, vapor deposition film thickness are 20nm；Finally, magnesium/ag alloy layer is successively deposited on above-mentioned electron transfer layer as device
Cathode layer, wherein magnesium/ag alloy layer evaporation rate is 2.0~3.0nm/s, and vapor deposition film thickness is 100nm.
Comparative example 1
Using Ir (piq)2(acac) compound represented replaces the metal complex in embodiment 14, other steps and reality
It is identical to apply example 14, makes comparative example 1.
TDC, DNTPD, NPD, LiQ, Ir (piq) above-mentioned2(acac) structural formula is as follows:
According to step same as described above, use metal complex of the invention as the dopant material system of organic luminous layer
Make organic electroluminescence device, structure and performance data are summarized in following table:
Table 2: the structure and performance data of the organic electroluminescence device of embodiment and ratio example
Conclusion: it is analyzed from the performance test results, metal complex of the invention, excitation purity is preferable, and chromaticity coordinate is pure red
Region or deep red region, performance is considerably beyond existing known red light material, and the luminescent lifetime of device is also very
Ideal.
Obviously, the above embodiment of the present invention be only to clearly illustrate example of the present invention, and not be pair
The restriction of embodiments of the present invention may be used also on the basis of the above description for those of ordinary skill in the art
To make other variations or changes in different ways, all embodiments can not be exhaustive here, it is all to belong to this hair
The obvious changes or variations that bright technical solution is extended out are still in the scope of protection of the present invention.
Claims (12)
1. a kind of metal complex, which is characterized in that the chemical molecular formula of the metal complex are as follows:
M(LA)x(LB)y(Lc)z
Wherein M indicates the metallic element that atomic weight is greater than 40；X indicates integer 1,2 or 3；Y indicates integer 0,1 or 2；Z indicates integer
0,1 or 2；And the sum of x, y, z is equal to the oxidation state of metal M；
LAThe group of the structure composition shown in Formulas I, the Formula II:
R1、R2、R3、R4、R41、R42、R43、R44Be each independently selected from hydrogen atom, D-atom, halogen atom, alkyl group, naphthenic base,
It is miscellaneous alkyl, aralkyl, alkoxy, aryloxy group, amino, alkenyl, cycloalkenyl containing nitrogen, oxygen, sulphur, silicon, germanium or phosphorus atoms, miscellaneous
Alkenyl, alkynyl, aryl, heterocyclic aryl, acyl group, carbonyl, carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulfonyl, sulfenyl
The group of base, phosphino-, phosphine oxygroup composition；Adjacent substituents optionally engage or are fused into five-membered ring, hexatomic ring or more in Formulas I, Formula II
Ring；X1It is each independently selected from carbon or nitrogen；The number of R4 is each independently 1~4 in Formulas I, Formula II；
LBAre as follows:
R5、R6Be each independently selected from hydrogen atom, D-atom, halogen atom, alkyl group, naphthenic base, containing nitrogen, oxygen, sulphur, silicon, germanium or
The miscellaneous alkyl of phosphorus atoms, aralkyl, alkoxy, aryloxy group, amino, alkenyl, cycloalkenyl, miscellaneous thiazolinyl, alkynyl, aryl, heterocycle
Aryl, acyl group, carbonyl, carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulfonyl, sulfinyl, phosphino-, phosphine oxygroup form
Group；Formula LBMiddle adjacent substituents optionally engage or are fused into five-membered ring, hexatomic ring or polycyclic；Ring C, ring D are selected each independently
From five yuan of carbocyclic rings, six-membered carbon ring, five-ring heterocycles or hexa-member heterocycle；Substituent R on ring C, ring D5、R6It is each independently one
Or two or more；X2For carbon or nitrogen；
LCAre as follows:
R7、R8、R9Be each independently selected from hydrogen atom, D-atom, halogen atom, alkyl group, naphthenic base, containing nitrogen, oxygen, sulphur, silicon,
The miscellaneous alkyl of germanium or phosphorus atoms, aralkyl, alkoxy, aryloxy group, amino, alkenyl, cycloalkenyl, miscellaneous thiazolinyl, alkynyl, aryl,
Heterocyclic aryl, acyl group, carbonyl, carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulfonyl, sulfinyl, phosphino-, phosphine oxygroup group
At group；R7、R8、R9Middle adjacent substituents optionally engage or are fused into five-membered ring, hexatomic ring or polycyclic.
2. metal complex according to claim 1, which is characterized in that the metal M is selected from Ir or Pt.
3. metal complex according to claim 2, which is characterized in that the molecular formula of the metal complex is Ir (LA)
(LB)(LC)、Ir(LA)2(LB)、Ir(LA)3、Ir(LA)2(LC)、Pt(LA)(LB) or Pt (LA)(LC)。
4. described in any item metal complexs according to claim 1~3, which is characterized in that the structural formula LASelected from following
The group of structure composition shown in formula III, formula IV:
In formula III, formula IV, R1、R2、R3、R4、R41、R42、R43、R44It is each independently selected from hydrogen atom, D-atom, halogen atom, chain
Alkyl, naphthenic base, the miscellaneous alkyl containing nitrogen, oxygen, sulphur, silicon, germanium or phosphorus atoms, aralkyl, alkoxy, aryloxy group, amino, alkene
Base, cycloalkenyl, miscellaneous thiazolinyl, alkynyl, aryl, heterocyclic aryl, acyl group, carbonyl, carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulphur
The group of acyl group, sulfinyl, phosphino-, phosphine oxygroup composition；R1、R2、R3、R4、R41、R42、R43、R44In between adjacent group optionally
Ground engages or is fused into five-membered ring, hexatomic ring or polycyclic.
5. metal complex according to claim 4, which is characterized in that in the formula III, formula IV, R1、R2、R3、R41、
R42、R43、R44、R4It is each independently selected from RA1~RA56And RB1~RB45The group of composition；
RA1~RA56Shown structural formula is as follows:
RB1~RB45Shown structural formula is as follows:
6. metal complex according to claim 5, which is characterized in that the formula III is selected from following LA1~LA1912
The group of composition:
The structural formula of LA1~LA1912 is as shown in the table:
The formula IV is selected from the group of the composition of LA1913~LA3482 shown in following table:
RA3、RA27、RA34Shown structural formula is as follows:
RB1To RB45Shown structural formula is as follows:
7. described in any item metal complexs according to claim 1~6, which is characterized in that the LBSelected from following structural formula
The group of composition:
Wherein Ra、Rb、Rc、RdIt is each independently selected from hydrogen, deuterium hydrogen, halogen, alkyl group, naphthenic base, contains nitrogen, oxygen, sulphur, silicon, germanium
Or it is the miscellaneous alkyls of phosphorus atoms, aralkyl, alkoxy, aryloxy group, amido, alkenyl, cycloalkenyl, miscellaneous thiazolinyl, alkynyl, aryl, miscellaneous
The group that aryl, acyl group, carbonyl, carboxylic acid group, ester group, itrile group, isonitrile base, sulfenyl, sulfinyl, sulfonyl, phosphorus base form；Wherein
Ra、Rb、Rc、RdMiddle any two adjacent substituents are optionally condensed or engage and form ring or form multidentate ligand.
8. metal complex according to claim 7, which is characterized in that the LBSelected from following LB1~LB36 structural formula:
9. metal complex according to any one of claims 1 to 8, which is characterized in that the structural formula LCSelected from following
Structural formula:
10. a kind of electroluminescent organic material, which is characterized in that its described in any item metal for containing claim 1~9 is matched
Close one of object or a variety of.
11. a kind of organic electroluminescence device, with organic luminous layer, which is characterized in that the organic luminous layer includes power
Benefit requires one of 1~9 described in any item metal complexs or a variety of.
12. organic electroluminescence device according to claim 11, which is characterized in that in the organic electroluminescence device
Organic luminous layer be in material of main part having doped with described in any item metal complexs of the claim 1~9
Machine luminescent layer,
The material of main part is selected from one of following compound or a variety of:
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