CN110041159A - New compound, electroluminescent organic material, organic electroluminescent device, electronic device - Google Patents

New compound, electroluminescent organic material, organic electroluminescent device, electronic device Download PDF

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CN110041159A
CN110041159A CN201910334369.9A CN201910334369A CN110041159A CN 110041159 A CN110041159 A CN 110041159A CN 201910334369 A CN201910334369 A CN 201910334369A CN 110041159 A CN110041159 A CN 110041159A
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optionally
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compound
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曹建华
温世文
董梁
王士波
唐永顺
纪秦思
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Beijing Chengzhi Yonghua Display Technology Co Ltd
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    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

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Abstract

Electroluminescent organic material, organic electroluminescent device, electronic equipment the invention discloses a kind of novel compound and comprising the compound.Shown in the structural formula of compound Formulas I described as follows.The compound of the present invention has excellent carrier transport ability as electroluminescent cell material, there is preferable filming performance using electroluminescent cell material prepared by the compound of the present invention, and materials synthesis and the method for purification are simply suitable for the features such as being mass produced.It can obviously reduce starting voltage using organic electroluminescent device prepared by the compound of the present invention, improve luminous efficiency and brightness.

Description

New compound, electroluminescent organic material, organic electroluminescent device, electronics Device
Technical field
The present invention relates to technical field of organic electroluminescence.In particular it relates to can be used as the novel of electroluminescent material Compound, the electroluminescent organic material comprising the new compound, organic electroluminescent device, electronic device.
Background technique
Organic electroluminescent (abbreviation OLED) and relevant studied early in pope in 1963 et al. first discovery organise Close the electro optical phenomenon of object monocrystalline anthracene.By development in twenties years, organic EL Material realized red, blue, green comprehensively Color shines, and application field also extends to the fields such as macromolecule and metal complex from small molecule.
Recent years ORGANIC ELECTROLUMINESCENCE DISPLAYS technology oneself tend to be mature, some products have entered market, but in industrialization In time-histories, still there are many problems demands to solve, and especially for making the various organic materials of element, carrier injection is passed Defeated performance, material electroluminescence performance, service life, excitation purity, between a variety of materials and the matching between each electrode etc., Shang You Many problems are also unresolved.Especially practical requirement is also not achieved in luminous efficiency and service life in light-emitting component, this is significantly Limit the development of OLED technology.And utilize the metal complex phosphor material of triplet emission that there is high luminous efficiency, Green light and red light material have reached requirement, but the Electronic Structure Characteristics that metal complex is special, lead to its blue light material Material is unable to reach requirement.
It is therefore desirable to the one side or more of these performances such as the brightness of electron mobility, driving voltage, element, efficiency The electroluminescent organic material that aspect is improved.
Summary of the invention
The present invention makes in view of the foregoing, and it is an object of the present invention to provide a kind of novel compound, as Organic Electricity The raw material of electroluminescent element material, thus, it is possible to provide the organic electroluminescence hair of starting voltage reduction, luminous efficiency, brightness raising Optical element material and organic electroluminescent device, and used the electronic equipment of the organic electroluminescent device.
In order to achieve the above objectives, the present invention adopts the following technical solutions:
A kind of compound, shown in structural formula Formulas I described as follows:
Wherein, R1、R2、R3、R4、R5Each independently represent hydrogen atom, D-atom, C1~C8Linear or branched alkyl group, C1 ~C8Linear chain or branched chain miscellaneous alkyl, optionally with substituent group C6~C60Aromatic radical, the C optionally with substituent group6~C60Virtue Fragrant race's vinyl, the C optionally with substituent group6~C60Polycyclic aromatic base, the C optionally with substituent group6~C60Aryl amine, optionally C with substituent group6~C60The fused ring aryl of nitrogen atom, the C optionally with substituent group6~C60The condensed ring of sulfur-bearing or oxygen atom Aryl, the C optionally with substituent group6~C60The fused ring aryl or the optional C with substituent group of phosphorous, silicon or boron atom3~C60 Heterocyclic aryl, any of them adjacent substituents optionally engage or are fused into five-membered ring, hexatomic ring or seven yuan or more Ring；
Wherein, A1、A2、A3、A4It is each independently selected from carbon or nitrogen.
Another aspect of the invention is a kind of material for organic electroluminescence device, and it includes the compound of the present invention.
Another aspect of the present invention is a kind of organic electroluminescent device, it includes first electrode, second electrode and is placed in One layer or more of organic layer between the first electrode, the second electrode；At least one layer of the organic layer includes this hair Bright compound.
Another aspect of the invention is a kind of electronic equipment, has organic electroluminescent device of the invention.
Novel compound carrier mobility with higher shown in Formulas I provided by the invention is suitable for as organic Electroluminescent cell materials'use, by material for organic electroluminescence device of the invention containing of the invention novel Compound, so as to provide starting voltage reductions, luminous efficiency, brightness raising material for organic electroluminescence device. In addition, new compound of the invention has good thermal stability and filming performance, applies and used in organic electroluminescent device Material, organic electroluminescent device in electronic equipment, are able to extend the service life of organic electroluminescent device, so as to reduce The manufacturing cost of material for organic electroluminescence device, organic electroluminescent device, electronic equipment.
Detailed description of the invention
Fig. 1 shows the structural schematic diagram of the organic electroluminescent device of an embodiment of the invention；
Fig. 2 shows the electron mobility figures of compound shown in formula P65 of the invention.
Specific embodiment
Embodiment is enumerated below to be illustrated.
[compound]
Shown in the compound of the present invention structural formula Formulas I described as follows:
Wherein, R1、R2、R3、R4、R5Each independently represent hydrogen atom, D-atom, C1~C8Linear or branched alkyl group, C1 ~C8Linear chain or branched chain miscellaneous alkyl, optionally with substituent group C6~C60Aromatic radical, the C optionally with substituent group6~C60Virtue Fragrant race's vinyl, the C optionally with substituent group6~C60Polycyclic aromatic base, the C optionally with substituent group6~C60Aryl amine, optionally C with substituent group6~C60The fused ring aryl of nitrogen atom, the C optionally with substituent group6~C60The condensed ring of sulfur-bearing or oxygen atom Aryl, the C optionally with substituent group6~C60The fused ring aryl or the optional C with substituent group of phosphorous, silicon or boron atom3~C60 Heterocyclic aryl, any of them adjacent substituents optionally engage or are fused into five-membered ring, hexatomic ring or seven yuan or more Ring；
Wherein, A1、A2、A3、A4It is each independently selected from carbon or nitrogen.
C above-mentioned1~C8Linear or branched alkyl group refer to, the alkyl of straight chain or branch with 1~8 carbon atom. The example of alkyl includes but is not limited to, methyl, ethyl, propyl, isopropyl, normal-butyl, tert-butyl, isobutyl group, amyl, hexyl, Isohesyl, heptyl, 4,4- dimethyl amyl group, octyl.
C above-mentioned1~C8Linear chain or branched chain miscellaneous alkyl refer to, one or more carbon quilts in the alkyl of linear chain or branched chain O, obtained miscellaneous alkyl after the hetero atoms such as N, P, Si, S replace, the carbon atom number in the miscellaneous alkyl is 1~8.As such The example of miscellaneous alkyl includes but is not limited to, methoxyl group, methoxy ethyl, ethoxyethyl group, dimethylamino, diethylin, two different Propyl amido, trimethyl silicon substrate.
The C optionally with substituent group above-mentioned6~C60Aromatic radical refers to, replaces or unsubstituted aryl, total carbon are former Subnumber is 6~60.As such aromatic radical, including but not limited to, phenyl, aminomethyl phenyl, ethylphenyl, isopropyl phenyl, Xenyl, naphthalene, quinolyl, isoquinolyl.
The C optionally with substituent group above-mentioned6~C60Aromatic ethenyl refers to, is connected with the vinyl of aryl, aryl On can also be unsubstituted with substituted base, the carbon atom number of entire group is 6~60, as such group, Ke Yilie It enumerates but is not limited to, such as styryl, methyl phenyl vinyl, diphenylethyllene, triphenylethylene base, N, N- hexichol amido benzene Vinyl, distyrene base etc..
The C optionally with substituent group above-mentioned6~C60Polycyclic aromatic base refers to, in substitution or unsubstituted condensed-nuclei aromatics Group after removing a hydrogen on aromatic rings, the total carbon atom number of entire group are 6~60, can be with as such group Enumerate but be not limited to, for example, naphthalene, anthryl, phenanthryl, pyrenyl, base, benzo phenanthryl,Base, pentacene etc..
The C optionally with substituent group above-mentioned6~C60Aryl amine refers to, replace or unsubstituted carbon atom number be 6~ The group that 60 aryl connection imino group is formed can be enumerated but be not limited to as such group, for example, anilino-, first Base phenyl amido, hexichol amido, benzidion, N- phenyl-naphthalenyl amido, N- phenyl-benzidion, N- phenyl-(9,9- diformazan Base fluorenes) -2- base amido, N- xenyl-(9,9- dimethyl fluorene) -2- base amido, N- pyridyl-phenyl amido, N- pyridyl group-connection Phenyl amido etc..
The C optionally with substituent group above-mentioned6~C60The fused ring aryl of nitrogen atom refers to, optionally thick with substituent group The group that carbon atom in cyclophane base on aromatic rings is replaced by more than one nitrogen-atoms, the carbon atom number of the group are 6~60, as such group, it can enumerate but be not limited to, for example, carbazyl, azepine carbazyl, benzo carbazole base, benzene And furans [2,3-b] carbazyl, 1,10- ferrosin base, benzofuran [3,2-b] pyridyl group, benzofuran [2,3-b] pyridyl group Deng.
The C optionally with substituent group above-mentioned6~C60The fused ring aryl of sulfur-bearing or oxygen atom refers to optionally there is substituent group Fused ring aryl in the group that is replaced by more than one sulphur atom or oxygen atom of carbon atom on aromatic rings, the group Carbon atom number be 6~60, as such group, can enumerate but be not limited to, for example, dibenzo [b, d] furyl, two Benzo [b, d] thienyl, naphtho- [2,1-b] benzofuranyl, naphtho- [1,2-b] benzofuranyl, spiral shell [fluorenes -9,9 '-oxa- Anthracene] base, spiral shell [fluorenes -9,9 '-thioxanthene] base, 9,9- xanthphos base, phenoxazine base etc..
The C optionally with substituent group above-mentioned6~C60The fused ring aryl of phosphorous, silicon or boron atom refers to optionally have and take The group that carbon atom in the fused ring aryl of Dai Ji on aromatic rings is replaced by more than one phosphorus, silicon or boron, the group Carbon atom number be 6~60, as such group, can enumerate but be not limited to, for example, triphenyl borine alkyl, triphenyl Phosphorus base, diyl base phosphorus oxygen base, trimethyl silicon substrate, phenyl-dimethyl silicon substrate, dibenzofurans -2- base diphenylphosphoryl group, dinaphtho [2,1-b:1', 2'-d] boryl etc..
The C optionally with substituent group above-mentioned3~C60Heterocyclic aryl refer to, optionally with substituent group aromatic rings on Obtained group after the one or more of carbon atom is replaced by hetero atoms such as N, P, S, O, the carbon atom number of the group for 2~ 60, as such group, it can enumerate but be not limited to, for example, phenyl, xenyl, naphthalene, quinolyl, indyl, hexichol And furyl, fluorenyl, two fluorenyl of spiral shell, dibenzothiophene, anthryl etc..
Preferably, the group of structure composition described in structural formula I Formula II~Formula IX selected from the following:
Wherein, R1、R2、R3、R4、R5It is each independently selected from hydrogen atom, D-atom, C1~C8Linear or branched alkyl group, C1 ~C8Linear chain or branched chain miscellaneous alkyl, optionally with substituent group C6~C60Aromatic radical, the C optionally with substituent group6~C60Virtue Fragrant race's vinyl, the C optionally with substituent group6~C60Polycyclic aromatic base, the C optionally with substituent group6~C60Aryl amine, optionally C with substituent group6~C60The fused ring aryl of nitrogen atom, the C optionally with substituent group6~C60The condensed ring of sulfur-bearing or oxygen atom Aryl, the C optionally with substituent group6~C60Phosphorous, silicon or boron atom fused ring aryl or optionally with the C of substituent group3~ C60Heterocyclic aryl；Any of them adjacent substituents optionally engage or are fused into five-membered ring, hexatomic ring or seven yuan or more Ring.
The C optionally with substituent group6~C60Aromatic radical, the C optionally with substituent group6~C60Aromatic ethenyl, Optionally with the C of substituent group6~C60Polycyclic aromatic base, the C optionally with substituent group6~C60Aryl amine optionally has substituent group C6~C60The fused ring aryl of nitrogen atom, the C optionally with substituent group6~C60The fused ring aryl of sulfur-bearing or oxygen atom, optionally C with substituent group6~C60Phosphorous, silicon or boron atom fused ring aryl or optionally with the C of substituent group3~C60Heterocycle Aryl contained in aryl is each independently selected from phenyl, xenyl, terphenyl, indenyl, naphthalene, camomile ring group, indacene Base, acenaphthylene base, fluorenyl ,-two fluorenyl of spiral shell, spiro-benzene and fluorenes-fluorenyl, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthracene Base, fluoranthene base, benzo phenanthryl, pyrenyl,Base, base, pentacene, pyrrole radicals, thienyl, pyranose, thiophene cough up base, isothiazole Base, oxazolyl, isoxazolyl, pyridyl group, pyrazinyl, pyrimidine radicals, pyridazinyl, indyl, isoindolyl, indazolyl, purine radicals, Quinolyl, isoquinolyl, benzoquinoline base, benzisoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, Benzoquinoxalines base, Quinazolyl, Benzoquinazole base, cinnoline base, phenanthridinyl, acridinyl, coffee sieve quinoline base, phenazinyl, benzimidazolyl, benzo furan Mutter base, benzothienyl, benzo thiophene coughs up base, benzothiazolyl, benzisothia oxazolyl, benzoxazolyl, benzo isoxazolyl, three Nitrogen oxazolyl, tetrazole radical, oxadiazoles base, triazine radical, carbazyl, dibenzofuran base, dibenzothiophen base, silicon fluorene base, benzo carbazole base, benzodiphenylene oxide Base, benzimidazole thiophanate fluorenyl, benzo silicon fluorene base, dibenzo-carbazole base, dibenzo dibenzofuran base, dibenzo dibenzothiophen base, dibenzo silicon fluorene base, Thiadiazolyl group, imidazopyridyl, imidazopyrimidine base, oxazole and pyridyl group, thiazolopyridinyl, benzo naphthyridines base, azepine Fluorenyl, two fluorenyl of azaspiro, azepine carbazyl, azepine dibenzofuran base, azepine dibenzothiophen base, aza-silicon fluorenyl, indeno-pyrrole base, indoles And the group of pyrrole radicals, indeno carbazyl, indolocarbazole base composition.
In Formulas I compound represented of the invention, it is preferable that above-mentioned optionally with the C of substituent group3~C60Heterocycle virtue Base is each independently selected from the group of structure composition shown in -1~II-13 of Formula II below.
Wherein, Z1、Z2Each independently represent hydrogen atom, D-atom, halogen atom, hydroxyl, itrile group, nitro, amino, amidino groups, Diazanyl, hydrazone group, carboxyl, carboxylate group, sulfonic group, sulfonate group, phosphate, phosphate base, C1~C60Alkyl group, C2~C60Chain Alkenyl, C2~C60Alkynyl, C1~C60Alkoxy, C3~C60Cycloalkyl group, C3~C60Cycloalkenyl group, C6~C60Aryl contains extremely Few-F ,-a CN or C1~C10The C of alkyl6~C60Aryl, the C optionally with substituent group6~C60Aryloxy group, optionally have take The C of Dai Ji6~C60Aromatic sulfide base or the C optionally with substituent group3~C60Heterocyclic aryl；
X1 indicates 1~4 integer；X2 indicates 1~3 integer；X3 indicates 1 or 2；X4 indicates 1~6 integer；X5 indicates 1 ~5 integer；
T1Selected from-B (R ')-,-N (R ')-,-P (R ')-,-O- ,-S- ,-Se- ,-S (=O)-,-S (O2)-、-C(R’ R ")-,-Si (R ' R ")-or-Ge (R ' R ")-；And R ', R " are each independently selected from C1~C60Alkyl group, C2~C60Alkenyl, C2~C60Alkynyl, C1~C60Alkoxy, C3~C60Cycloalkyl group, C3~C60Cycloalkenyl group, C6~C60Aryl contains C1~C10Alkane The C of base6~C60Aryl, the C optionally with substituent group6~C60Aryloxy group, the C optionally with substituent group6~C60Arylthio；R', R " is optionally condensed or engages and forms ring；
Indicate the connecting key of substituent group and main structure.
In Formulas I compound represented of the invention, it may be preferable that Formulas I compound represented above-mentioned be selected from following Formula II, Formula III, formula IV, Formula V, Formula IV, Formula VII, Formula VIII, the group of Formula IX compound represented composition:
Wherein, R1、R2、R3、R4、R5It is each independently selected from hydrogen atom, D-atom, C1~C8Linear or branched alkyl group, C1 ~C8Linear chain or branched chain miscellaneous alkyl, optionally with substituent group C6~C60Aromatic radical, the C optionally with substituent group6~C60Virtue Fragrant race's vinyl, the C optionally with substituent group6~C60Polycyclic aromatic base, the C optionally with substituent group6~C60Aryl amine, optionally C with substituent group6~C60The fused ring aryl of nitrogen atom, the C optionally with substituent group6~C60The condensed ring of sulfur-bearing or oxygen atom Aryl, the C optionally with substituent group6~C60Phosphorous, silicon or boron atom fused ring aryl or optionally with the C of substituent group3~ C60Heterocyclic aryl composition group；Any of them adjacent substituents optionally engage or are fused into five-membered ring, hexatomic ring or seven Ring more than member.
The C optionally with substituent group6~C60Aromatic radical, the C optionally with substituent group6~C60Aromatic ethenyl, Optionally with the C of substituent group6~C60Polycyclic aromatic base, the C optionally with substituent group6~C60Aryl amine optionally has substituent group C6~C60The fused ring aryl of nitrogen atom, the C optionally with substituent group6~C60The fused ring aryl of sulfur-bearing or oxygen atom, optionally C with substituent group6~C60Phosphorous, silicon or boron atom fused ring aryl or optionally with the C of substituent group3~C60Heterocycle Aryl contained in aryl is each independently selected from phenyl, xenyl, terphenyl, indenyl, naphthalene, camomile ring group, indacene Base, acenaphthylene base, fluorenyl ,-two fluorenyl of spiral shell, spiro-benzene and fluorenes-fluorenyl, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthracene Base, fluoranthene base, benzo phenanthryl, pyrenyl,Base, base, pentacene, pyrrole radicals, thienyl, pyranose, thiophene cough up base, different thiophene Oxazolyl, oxazolyl, isoxazolyl, pyridyl group, pyrazinyl, pyrimidine radicals, pyridazinyl, indyl, isoindolyl, indazolyl, purine Base, quinolyl, isoquinolyl, benzoquinoline base, benzisoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, Benzoquinoxalines Base, quinazolyl, Benzoquinazole base, cinnoline base, phenanthridinyl, acridinyl, coffee sieve quinoline base, phenazinyl, benzimidazolyl, benzo Furyl, benzothienyl, benzo thiophene cough up base, benzothiazolyl, benzisothia oxazolyl, benzoxazolyl, benzo isoxazolyl, Triazol radical, tetrazole radical, oxadiazoles base, triazine radical, carbazyl, dibenzofuran base, dibenzothiophen base, silicon fluorene base, benzo carbazole base, benzo oxygen Fluorenyl, benzimidazole thiophanate fluorenyl, benzo silicon fluorene base, dibenzo-carbazole base, dibenzo dibenzofuran base, dibenzo dibenzothiophen base, dibenzo silicon fluorene Base, thiadiazolyl group, imidazopyridyl, imidazopyrimidine base, oxazole and pyridyl group, thiazolopyridinyl, benzo naphthyridines base, nitrogen Miscellaneous fluorenyl, two fluorenyl of azaspiro, azepine carbazyl, azepine dibenzofuran base, azepine dibenzothiophen base, aza-silicon fluorenyl, indeno-pyrrole base, Yin Diindyl and pyrrole radicals, indeno carbazyl, any one or more in indolocarbazole base.
In Formulas I compound represented of the invention, it is preferably selected from what following formula P01 was formed to P258 compound represented Group, wherein X is-O- ,-S- or-C (CH3)2-。
The material of the compound of the present invention has the ability of carrier transport.
[material for organic electroluminescence device]
Material for organic electroluminescence device of the invention contains the compound of the present invention.Organic illuminating element material can It is constituted so that the compound of the present invention is used alone, other compounds can also be contained simultaneously.
The compound of the present invention contained in material for organic electroluminescence device of the invention may be used as doping material Material.At this point, the compound of the present invention as dopant material can be contained in material for organic electroluminescence device of the invention, And other compounds as material of main part.It is of the invention contained in material for organic electroluminescence device of the invention Compound is also used as material of main part.At this point, can be containing as master in material for organic electroluminescence device of the invention The compound of the present invention of body material, and other compounds as dopant material.
[organic electroluminescent device]
Organic electroluminescent device of the invention includes first electrode, second electrode and is placed in the first electrode, described One or more organic layers between second electrode, the organic layer can further contain inorganic compound.Of the invention has In electro-luminescence element, at least one layer in aforementioned organic layer is luminescent layer.The organic layer can be hole injection layer, sky Cave transport layer, electron injecting layer, electron transfer layer, hole barrier layer, electronic wall barrier layer etc., organic electroluminescent member of the invention In part, at least one layer in aforementioned organic layer includes one of the compound of the present invention or a variety of.
Formulas I compound represented of the invention may be used as in organic electroluminescent device for example, red phosphorescence material, Red fluorescence material, hole-injecting material, hole mobile material or encapsulation layer material.
Organic electroluminescent device of the invention can be bottom emitting optical element either top emitting optical element.This The structure and preparation method of the organic electroluminescent device of invention do not limit.Using Organic Electricity made from the compound of the present invention Electroluminescent element can drop low start voltage, improve luminous efficiency and brightness.
Typical case as organic electroluminescent device of the invention is constituted, and can be enumerated but structure not limited to the following:
(a) anode/luminescent layer/cathode
(b) anode/hole injection-transport layer/luminescent layer/cathode
(c) anode/luminescent layer/electron injection-transport layer/cathode
(d) anode/hole injection-transport layer/luminescent layer/electron injection-transport layer/cathode
(e) anode/hole injection-transport layer/the first luminescent layer/second luminescent layer/electron injection-transport layer/cathode
(f) anode/hole injection-transport layer/luminescent layer/electronic barrier layer/electron injection-transport layer/cathode
(g) anode/hole injection-transport layer/hole blocking layer/luminescent layer/electron injection-transport layer/cathode
Deng.
The signal composition figure of one example of organic electroluminescent device of the invention is shown in Fig. 1.As of the invention One specific example of organic electroluminescence device, is illustrated referring to Fig.1.In Fig. 1, successively there is anode layer on substrate 1 2, hole injection layer 3, hole transport/electronic barrier layer 4, organic luminous layer 5, hole barrier/electron transfer layer 6, electron injection Layer 7, cathode layer 8.In organic electroluminescent device of the invention, above-mentioned the compound of the present invention preferably is contained in organic light emission In layer.
Embodiment
Hereinafter, being illustrated to the embodiment of the present invention, however, the present invention is not limited to these examples.
In addition, unless otherwise specified, it is raw materials used in the present invention can be by commercially available commercially available, documented by the present invention Any range includes that any numerical value between end value and end value and any number between end value or end value are constituted Any subrange.
In order to illustrate more clearly of the present invention, the present invention is done further below with reference to preferred embodiments and drawings It is bright.Similar component is indicated in attached drawing with identical appended drawing reference.It will be appreciated by those skilled in the art that institute is specific below The content of description is illustrative and be not restrictive, and should not be limited the scope of the invention with this.
In the description of the present invention, unless otherwise indicated, the meaning of " plurality " is two or more；Term " on ", The orientation or positional relationship of the instructions such as "lower" is to be based on the orientation or positional relationship shown in the drawings, and is merely for convenience of describing this hair Bright and simplified description, rather than the device or element of indication or suggestion meaning must have a particular orientation, with specific orientation Construction and operation, therefore be not considered as limiting the invention.
In the present invention, preparation method is then conventional method unless otherwise specified.Raw material used is equal unless otherwise instructed It can be obtained from disclosed commercial sources, the percentage is mass percent unless otherwise specified.
The test equipment and method that following embodiments are tested for the property OLED material and element are as follows:
OLED element performance detection condition:
Brightness and chromaticity coordinate: it is tested using spectrum scanner PhotoResearch PR-715；
Current density and bright voltage: it is tested using digital sourcemeter Keithley 2420；
Power efficiency: it is tested using NEWPORT 1931-C；
Life test: LTS-1004AC endurance testing device is used.
Embodiment 1
The preparation method of compound P01, includes the following steps:
Step 1: the preparation of compound Int-1
The 2- iodine benzyltriphenylphosphonium salt of 61.5g (0.11mol) is dispersed in the anhydrous THF of 350mL, under nitrogen protection, It is cooled to 0 DEG C with ice salt bath, the potassium tert-butoxide of 14.8g (0.13mmol) is added portionwise, after being stirred to react 30 minutes, is added dropwise to The 2- bromobenzaldehyde of 18.5g (0.1mol), after adding, insulated and stirred is reacted 1 hour, is raised to and reaction 24 hours is stirred at room temperature, add Enter 150mL saturated aqueous ammonium chloride, be extracted with ethyl acetate, organic phase is dried, filtered with anhydrous sodium sulfate, is concentrated under reduced pressure It is dry, with silica gel column separating purification, the yellow oil of 35.8g is obtained, is cis/trans mixture, yield: 93%.
Step 2: the preparation of compound Int-2
The intermediate compound I nt-1 for taking 35.0g (90.9mmol) first step to prepare is dissolved in the deuterated ethyl alcohol of 200mL, then plus The sodium ethoxide for entering 31.0g (0.45mol) is warming up to 60 DEG C and is stirred to react 48 hours, is cooled to room temperature, is concentrated under reduced pressure and does, uses silicon Rubber column gel column isolates and purifies, and obtains the compound Int-2 of 32.5g, yellow oil.
Step 3: the preparation of compound Int-3
The intermediate compound I nt-2 for taking 35.0g (90.9mmol) second step to prepare is dissolved in the toluene of 250mL, and 32.7g is added The three normal-butyl hydrogen tin of (0.11mol), add the azodiisobutyronitrile of 3.0g (18.2mmol), under nitrogen protection, heating Return stirring reacts 12 hours, adds the three normal-butyl hydrogen tin of 5.3g (18.2mmol) and the azo two of 0.6g (3.6mmol) Isobutyronitrile continues return stirring and reacts 12 hours, be cooled to room temperature, is concentrated under reduced pressure and does, dissolved and be washed with water with methylene chloride, satisfied It is washed with salt, organic phase dries, filters, and filtrate decompression concentration is dry, with silica gel column separating purification, obtains the white solid of 19.6g, receives Rate: 84%.
Step 4: the preparation of compound Int-4
The intermediate compound I nt-3 for taking 20.0g (77.2mmol) third step to prepare is dissolved in the dry THF of 150mL, in nitrogen Under protection, with liquid nitrogen cooling to -78 DEG C, it is added dropwise to the 2.5M n-BuLi hexane solution of 37.0mL, is stirred to react 30 minutes, The trimethylborate for being added dropwise to 11.5g (0.11mol) is dissolved in the solution of dry THF, is raised to and reaction 1 hour is stirred at room temperature, and is added The 3N dilute hydrochloric acid of 50mL is stirred to react 30 minutes, is extracted with ethyl acetate, and organic phase dries, filters, and filtrate decompression concentration is dry, is added Enter petroleum ether dispersion, filtering obtains the Int-3 of 14.2g, white solid, yield: 82%.
Step 5: the preparation of compound P01
Under nitrogen protection, the 9- (7- of Int-4,20.5g (40.4mmol) of the preparation of the 4th step of 10.0g (44.6mmol) Bromonaphthalene -2- base) -10- (1- naphthalene) anthracene, 18.0g (0.17mol) natrium carbonicum calcinatum mixing, add the Pd of 15.0mg (PPh3)4The toluene of catalyst and 100mL, the ethyl alcohol of 50mL and the water of 50mL, are heated to flowing back, and are stirred to react 12 hours, cooling To room temperature, the water dilution of 50mL is added, is extracted with toluene, collects organic phase, dry, filter, filtrate decompression concentration is dry, uses silica gel Column separating purification obtains the Formula P01 of 20.2g, white solid.
Embodiment 2
Compound P02~P38, P40~P51, P112, P247, P253~P256 preparation, referring to the preparation of embodiment 1 Method, by 9- (7- bromonaphthalene -2- base) -10- (1- naphthalene) anthracene of the 5th step in different halides alternative embodiments 1, preparation formula I In P02~P38, P40~P51, P112, P247, P253~P256.
Embodiment 3
The preparation method of compound P65, includes the following steps:
Step 1: the preparation of compound Int-5
Benzo [h] quinoline of 10.0g (55.8mmol) and the NBS of 20.0g (0.11mol) are dispersed in the N, N- bis- of 100mL In methylacetamide, dichloro (p -Methylisopropylbenzene base) ruthenium (II) dimerization body catalyst of 1.7g (2.7mmol) is added, is risen Temperature is stirred to react 48 hours to 100 DEG C, is cooled to room temperature, and the water dilution of 200mL is added, is extracted with ethyl acetate, collects organic Phase dries, filters, and filtrate decompression concentration is dry, with silica gel column separating purification, obtains the intermediate compound I nt-4 of 10.9g, yellow oil.
Step 2: the preparation of compound Int-6
Referring to the preparation method of the 4th step of embodiment 1, by the Int-3 of the 4th step in intermediate compound I nt-5 alternative embodiment 1, Prepare intermediate compound I nt-6, yellow powdery solid.
Step 3: the preparation of compound P65
Under nitrogen protection, the 2- of Int-6,19.0g (37.3mmol) of the preparation of 10.0g (44.8mmol) second step are bromo- The natrium carbonicum calcinatum mixing of 9,10- bis- (2- naphthalene) anthracenes, 18.0g (0.17mol), adds the Pd (PPh of 15.0mg3)4Catalyst It with the water of the toluene of 100mL, the ethyl alcohol of 50mL and 50mL, is heated to flowing back, is stirred to react 12 hours, is cooled to room temperature, be added The water of 50mL dilutes, and is extracted with toluene, collects organic phase, dries, filters, and filtrate decompression concentration is dry, with silica gel column separating purification, Obtain the Formula P65 of 20.0g, white solid.It is attached that Fig. 2 shows the electron mobility figures of compound P65.
Embodiment 4
The system of compound P52~P64, P66~P93, P97~P103, P109~P111, P113, P203, P248, P250 It is standby, referring to the preparation method of embodiment 3, by bis- (the 2- naphthalenes of bromo- 9, the 10- of 2- of third step in different halides alternative embodiments 3 Base) anthracene, P52~P64, P66~P93, P97~P103, P109~P111, P113, P203, P248, P250 in preparation formula I.
Embodiment 5
The preparation of compound P106:
9- (the 4- dibenzo of the intermediate compound I nt-5 and 17.6mmol of the preparation of 3 first step of 5.0g (19.3mmol) embodiment [b, d] furans) -9H, 9'H-3,3'- joins carbazole or 9- (4- dibenzo [b, d] thiophene) -9H, 9'H-3,3'- join carbazole, 2.8g The sodium tert-butoxide of (29.0mmol) adds the Pd of 0.2g (0.19mmol)2(dba)3CHCl3The toluene of catalyst and 80mL, It under nitrogen protection, is warming up to 100 DEG C and is stirred to react 24 hours, be cooled to room temperature, the water dilution of 100mL, filtering is added, filter cake is used Washing, ethyl alcohol are washed, and with silica gel column separating purification, obtaining compound P106, (X is that the compound of oxygen obtains 9.9g, light yellow solid； X is that the compound of sulphur obtains 10.2g, yellow solid).
Embodiment 6
The preparation of compound P94~P96, P104, P105, P107, P108, P178, P183, referring to the preparation of embodiment 5 9- (4- dibenzo [b, d] furans) -9H in different substituted carbazole alternative embodiments 5,9'H-3,3'- are joined carbazole by method, P94~P96, P104, P105, P107, P108, P178, P183 in preparation formula I.
Embodiment 7
The preparation method of compound P116, including following reaction step:
Step 1: the preparation of intermediate compound I nt.-6
Under nitrogen protection, the 3- bromine-2-methylpyridine of 10.0g (58.1mmol), the 3- of 11.8g (63.9mmol) are chloro- The natrium carbonicum calcinatum mixing of 2- carboxaldehyde radicals phenyl boric acid, 12.3g (0.11mol), adds the Pd (PPh of 3.4g3)4Catalyst and The water of the toluene of 60mL, the methanol of 30mL and 30mL is heated to 90 DEG C, is stirred to react 15 hours, is cooled to room temperature, and 50mL is added Water dilution, be extracted with ethyl acetate, collect organic phase, dry, filter, filtrate decompression concentration is dry, with silica gel column separating purification, Obtain the intermediate compound I nt-6 of 10.2g, yellow solid.
Step 2: the preparation of compound Int-7
Under nitrogen protection, the intermediate compound I nt-6 for taking 10.0g (43.1mmol) first step to prepare is dissolved in the DMF of 80mL In, the potassium tert-butoxide of 9.7g (86.3mmol) is added portionwise, reaction 12 hours is stirred at room temperature, reaction solution is poured into the water of 250mL In, it is extracted with dichloromethane, organic phase is dried, filtered with anhydrous sodium sulfate, is concentrated under reduced pressure and is done, with silica gel column separating purification, obtains The compound Int-7 of 7.4g, white solid.
Step 3: the preparation of compound Int-8
Referring to the preparation method of the 4th step of embodiment 1, by the Int-3 of the 4th step in intermediate compound I nt-7 alternative embodiment 1, Prepare intermediate compound I nt-8, yellow solid.
Step 4: the preparation of compound P116
Under nitrogen protection, the 3- (9- of Int-8,22.3g (37.3mmol) of the preparation of 10.0g (44.8mmol) third step (4- chloro-6-phenyl -1,3,5- triazine -2- base) dibenzo [b, d] furans -2- base) -9- phenyl -9H- carbazole, 18.0g The natrium carbonicum calcinatum of (0.17mol) mixes, and adds the Pd (PPh of 15.0mg3)4The second of the toluene of catalyst and 100mL, 50mL The water of pure and mild 50mL is heated to flowing back, and is stirred to react 12 hours, is cooled to room temperature, and the water dilution of 50mL is added, is extracted with toluene It takes, collects organic phase, dry, filter, filtrate decompression concentration is dry, recrystallizes, obtains with silica gel column separating purification, then with tetrahydrofuran 18.3g Formula P116, white solid.
Embodiment 8
The preparation of compound P118~P159, P163~P169, P175~P177, P249, referring to the preparation side of embodiment 7 Method, the compound by the bromo- 10- of 9- (1- naphthalene) anthracene of the 4th step in different halides alternative embodiments 7, in preparation formula I P118~P159, P163~P169, P175~P177, P249.
Embodiment 9
The preparation of compound P160~P162, P170~P174, P181, P246 will referring to the preparation method of embodiment 5 The intermediate compound I nt-5 in intermediate compound I nt-7 alternative embodiment 5 that in embodiment 7 prepared by second step, different substituted carbazoles are replaced Changing 9- (4- dibenzo [b, d] furans) -9H in embodiment 5,9'H-3,3'- join carbazole, P160~P162 in preparation formula I, P170~P174, P181, P246.
Embodiment 10
The preparation method of compound P203, including following reaction step:
Step 1: the preparation of intermediate compound I nt.-9
Under nitrogen protection, the bromo- 4- picoline of the 3- of 10.0g (58.1mmol), the 3- of 11.8g (63.9mmol) are chloro- The natrium carbonicum calcinatum mixing of 2- carboxaldehyde radicals phenyl boric acid, 12.3g (0.11mol), adds the Pd (PPh of 3.4g3)4Catalyst and The water of the toluene of 60mL, the methanol of 30mL and 30mL is heated to 90 DEG C, is stirred to react 15 hours, is cooled to room temperature, and 50mL is added Water dilution, be extracted with ethyl acetate, collect organic phase, dry, filter, filtrate decompression concentration is dry, with silica gel column separating purification, Obtain the intermediate compound I nt-9 of 11.8g, yellow solid.
Step 2: the preparation of compound Int-10
Under nitrogen protection, the intermediate compound I nt-9 for taking 11.0g (47.4mmol) first step to prepare is dissolved in the DMF of 150mL In, the potassium tert-butoxide of 10.6g (95.0mmol) is added portionwise, reaction 12 hours is stirred at room temperature, reaction solution is poured into the water of 550mL In, it is extracted with dichloromethane, organic phase is dried, filtered with anhydrous sodium sulfate, is concentrated under reduced pressure and is done, with silica gel column separating purification, obtains The compound Int-10 of 8.3g, white solid.
Step 3: the preparation of compound Int-11
Referring to the preparation method of the 4th step of embodiment 1, by the Int-3 of the 4th step in intermediate compound I nt-10 alternative embodiment 1, Prepare intermediate compound I nt-11, yellow solid.
Step 4: the preparation of compound P203
Referring to the preparation method of 3 third step of embodiment, by the Int-6 of third step in intermediate compound I nt-11 alternative embodiment 3, The 2- of third step in intermediate 3,3'- ((2- bromine anthracene -9,10- diyl) bis- (4,1- phenyl)) two pyridine alternative embodiments 3 is bromo- 9,10- bis- (2- naphthalene) anthracenes, prepare compound P203, yellow solid.
Embodiment 11
Compound P114, P115, P184~P202, P204~P243, P251 preparation, synthetic operation is referring to embodiment 10, by 3, the 3'- ((2- bromine anthracene -9,10- diyl) bis- (4,1- phenyl)) in different the 4th steps of halides alternative embodiment 10 Two pyridines obtain P114, P115, P184~P202, P204~P243, P251 in Formula I.
Embodiment 12
The preparation of compound P39, P117, P179, P180, P182, P244, P245, P252, P257, P258, referring to implementation The preparation method of example 5, the intermediate compound I nt-5 in intermediate compound I nt-10 alternative embodiment 5 prepared by second step in embodiment 10, 9- (4- dibenzo [b, d] furans) -9H in different substituted carbazole alternative embodiments 5,9'H-3,3'- are joined into carbazole, preparation P39, P117, P179, P180, P182, P244, P245, P252, P257, P258 in Formulas I.
The comparative example of organic electroluminescent device
Using compound shown in following formula A as a comparison sample as Blue-light emitting host material, using shown in following formula B As compound shown in blue light dopant material, formula C as hole-injecting material, compound shown in formula D passes compound as hole Defeated material, the electron-transport dopant material as a comparison sample of compound shown in formula E, as described below prepares organic electroluminescent Element.
By chemical formula C (80nm)/D (30nm)/A+B (5%) (30nm)/LiQ+E (50%) (2nm)/LiF (1nm)/Al Having as a comparison case is made successively using the EL evaporator vapor deposition of DOV company manufacture to element is made on ito glass in (60nm) Electro-luminescence element.
The embodiment of organic electroluminescent device
In the comparative example of organic electroluminescent device above-mentioned, compound A above-mentioned is replaced with into chemical combination of the invention Object P01~P258, in addition to this, using same method production organic electroluminescent device: ITO/C (80nm)/D (30nm)/ [the compound of the present invention P01~P258]+B (5%) (30nm)/LiQ+E (50%) (2nm)/LiF (1nm)/Al (60nm)
The performance test results of gained element are listed in Table 1 below.
Table 1: element function testing result
From the foregoing, it will be observed that the element drive voltage that organic material of the invention is prepared into is low, external quantum efficiency is higher, excitation purity Preferably, and under conditions of element light emission luminance is initially on the basis of 1000 nits, use the compound of the present invention as indigo plant The component life of light material of main part is well very much.
In the comparative example of organic electroluminescent device above-mentioned, compound E above-mentioned is replaced with into chemical combination of the invention In addition to this object P01~P258 makes organic electroluminescent device: ITO/C (80nm)/D (30nm)/A using same method + B (5%) (30nm)/LiQ+ [the compound of the present invention P01~P258] (50%) (2nm)/LiF (1nm)/Al (60nm)
The performance test results of gained element are listed in Table 2 below.
Table 2: element function testing result
From the foregoing, it will be observed that the element drive voltage that organic material of the invention is prepared into is low, external quantum efficiency is high, and shine colour purity Degree preferably, and under conditions of element light emission luminance is initially on the basis of 1000 nits, uses the compound of the present invention electronics The component life decaying of transmission material is many slowly.
Obviously, the citing that application of the invention is not limited to the above embodiments, carrys out those of ordinary skill in the art It says, other different forms of changes or modifications may be made based on the above description, here can not be to all implementation Mode is exhaustive, all to belong to obvious changes or variations that technical solution of the present invention is extended out still in this hair The column of the protection scope of bright appended claims.

Claims (9)

1. a kind of compound, which is characterized in that the structural formula of the compound is shown in formula I:
Wherein, R1、R2、R3、R4、R5Each independently represent hydrogen atom, D-atom, C1~C8Linear or branched alkyl group, C1~C8 Linear chain or branched chain miscellaneous alkyl, optionally with substituent group C6~C60Aromatic radical, the C optionally with substituent group6~C60Aromatic series Vinyl, the C optionally with substituent group6~C60Polycyclic aromatic base, the C optionally with substituent group6~C60Aryl amine optionally has The C of substituent group6~C60The fused ring aryl of nitrogen atom, the C optionally with substituent group6~C60The condensed ring of sulfur-bearing or oxygen atom virtue Base, the C optionally with substituent group6~C60Phosphorous, silicon or boron atom fused ring aryl or optionally with the C of substituent group3~C60 Heterocyclic aryl, any of them adjacent substituents optionally engage or are fused into five-membered ring, hexatomic ring or seven yuan or more Ring；
A1、A2、A3、A4It is each independently selected from carbon or nitrogen.
2. compound according to claim 1, which is characterized in that the structural formula I Formula II selected from the following~Formula IX institute Show the group of structural formula composition:
Wherein, R1、R2、R3、R4、R5Each independently represent hydrogen atom, D-atom, C1~C8Linear or branched alkyl group, C1~C8 Linear chain or branched chain miscellaneous alkyl, optionally with substituent group C6~C60Aromatic radical, the C optionally with substituent group6~C60Aromatic series Vinyl, the C optionally with substituent group6~C60Polycyclic aromatic base, the C optionally with substituent group6~C60Aryl amine optionally has The C of substituent group6~C60The fused ring aryl of nitrogen atom, the C optionally with substituent group6~C60The condensed ring of sulfur-bearing or oxygen atom virtue Base, the C optionally with substituent group6~C60Phosphorous, silicon or boron atom fused ring aryl or optionally with the C of substituent group3~C60 Heterocyclic aryl, any of them adjacent substituents optionally engage or are fused into five-membered ring, hexatomic ring or seven yuan or more Ring；
The C optionally with substituent group6~C60Aromatic radical, the C optionally with substituent group6~C60Aromatic ethenyl, optionally C with substituent group6~C60Polycyclic aromatic base, the C optionally with substituent group6~C60Aryl amine, the C optionally with substituent group6 ~C60The fused ring aryl of nitrogen atom, the C optionally with substituent group6~C60Contained in the fused ring aryl of sulfur-bearing or oxygen atom Aryl is each independently selected from phenyl, xenyl, terphenyl, indenyl, naphthalene, camomile ring group, indacene base, acenaphthylene base, fluorenes Base ,-two fluorenyl of spiral shell, spiro-benzene and fluorenes-fluorenyl, benzo fluorenyl, dibenzo fluorenyl, that non-alkenyl, phenanthryl, anthryl, fluoranthene base, benzene And phenanthryl, pyrenyl,Base, base, pentacene, pyrrole radicals, thienyl, pyranose, thiophene cough up base, isothiazolyl, oxazolyl, It is isoxazolyl, pyridyl group, pyrazinyl, pyrimidine radicals, pyridazinyl, indyl, isoindolyl, indazolyl, purine radicals, quinolyl, different Quinolyl, benzoquinoline base, benzisoquinoline base, phthalazinyl, naphthyridines base, quinoxalinyl, Benzoquinoxalines base, quinazolyl, Benzoquinazole base, cinnoline base, phenanthridinyl, acridinyl, coffee sieve quinoline base, phenazinyl, benzimidazolyl, benzofuranyl, benzo Thienyl, benzo thiophene cough up base, benzothiazolyl, benzisothia oxazolyl, benzoxazolyl, benzo isoxazolyl, triazol radical, four Oxazolyl, oxadiazoles base, triazine radical, carbazyl, dibenzofuran base, dibenzothiophen base, silicon fluorene base, benzo carbazole base, benzodiphenylene oxide base, benzimidazole thiophanate Fluorenyl, benzo silicon fluorene base, dibenzo-carbazole base, dibenzo dibenzofuran base, dibenzo dibenzothiophen base, dibenzo silicon fluorene base, thiadiazolyl group, Imidazopyridyl, imidazopyrimidine base, oxazole and pyridyl group, thiazolopyridinyl, benzo naphthyridines base, azepine fluorenyl, azepine Two fluorenyl of spiral shell, azepine carbazyl, azepine dibenzofuran base, azepine dibenzothiophen base, aza-silicon fluorenyl, indeno-pyrrole base, indoles and pyrrole radicals, The group of indeno carbazyl, indolocarbazole base composition.
3. compound according to claim 1, which is characterized in that described optionally with the C of substituent group3~C60Heterocycle virtue Base is selected from the group of structure composition shown in following X-1~X-13:
Wherein, Z1、Z2Each independently represent hydrogen atom, D-atom, halogen atom, hydroxyl, itrile group, nitro, amino, amidino groups, hydrazine Base, hydrazone group, carboxyl, carboxylate group, sulfonic group, sulfonate group, phosphate, phosphate base, C1~C60Alkyl group, C2~C60Alkene Base, C2~C60Alkynyl, C1~C60Alkoxy, C3~C60Cycloalkyl group, C3~C60Cycloalkenyl group, C6~C60Aryl contains at least One-F ,-CN or C1~C10The C of alkyl6~C60Aryl, the C optionally with substituent group6~C60Aryloxy group optionally has substitution The C of base6~C60Aromatic sulfide base or the C optionally with substituent group3~C60Heterocyclic aryl；
X1 indicates 1~4 integer；X2 indicates 1~3 integer；X3 indicates 1 or 2；X4 indicates 1~6 integer；X5 indicates 1~5 Integer；
T1Selected from-B (R ')-,-N (R ')-,-P (R ')-,-O- ,-S- ,-Se- ,-S (=O)-,-S (O2)-、-C(R’R”)-、-Si (R ' R ")-or-Ge (R ' R ")-；And R ', R " are each independently selected from C1~C60Alkyl group, C2~C60Alkenyl, C2~C60Alkynes Base, C1~C60Alkoxy, C3~C60Cycloalkyl group, C3~C60Cycloalkenyl group, C6~C60Aryl contains C1~C10The C of alkyl6~ C60Aryl, the C optionally with substituent group6~C60Aryloxy group, the C optionally with substituent group6~C60Any one in arylthio； R ', R " are optionally condensed or engagement forms ring；
Indicate the connecting key of substituent group and main structure.
4. according to claim 1 or 2 described in any item compounds, which is characterized in that the compound be selected from following P01~ The group of the composition of compound shown in P258, the X in formula P01~P258 are-O- ,-S- or-C (CH3)2):
5. a kind of electroluminescent organic material, described in any item compounds containing Claims 1 to 4.
6. a kind of organic electroluminescent device it includes first electrode, second electrode and is placed in the first electrode, described second One layer or more of organic layer between electrode；
At least one layer of the organic layer includes described in any item compounds of Claims 1 to 4.
7. organic electroluminescent device according to claim 6, which is characterized in that the compound is in the organic electroluminescence It is used as material of main part, electron transport materials, hole transporting material, dopant material or encapsulation layer material in light-emitting component.
8. a kind of electronic equipment contains organic electroluminescent device described in claim 6 or 7.
9. application of the described in any item compounds of Claims 1 to 4 in organic electroluminescent device.
CN201910334369.9A 2019-04-24 2019-04-24 New compound, electroluminescent organic material, organic electroluminescent device, electronic device Withdrawn CN110041159A (en)

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