CN103865220A - Organic metal polymer composition, preparation method thereof, and organic light emitting diode manufactured from composition - Google Patents
Organic metal polymer composition, preparation method thereof, and organic light emitting diode manufactured from composition Download PDFInfo
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- CN103865220A CN103865220A CN201310575175.0A CN201310575175A CN103865220A CN 103865220 A CN103865220 A CN 103865220A CN 201310575175 A CN201310575175 A CN 201310575175A CN 103865220 A CN103865220 A CN 103865220A
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- FCWVXQUIVVLNRY-UHFFFAOYSA-N BC(C)(C)c(c(F)c(c(F)c1F)F)c1F Chemical compound BC(C)(C)c(c(F)c(c(F)c1F)F)c1F FCWVXQUIVVLNRY-UHFFFAOYSA-N 0.000 description 1
- ZVSIDEKMGNBEAW-UHFFFAOYSA-N BC(C)(COc1cc(C(c2ccccc2)c2ccccc2)ccc1)c(c(F)c(c(F)c1F)F)c1F Chemical compound BC(C)(COc1cc(C(c2ccccc2)c2ccccc2)ccc1)c(c(F)c(c(F)c1F)F)c1F ZVSIDEKMGNBEAW-UHFFFAOYSA-N 0.000 description 1
- NBOXZRBYWXQDLY-UHFFFAOYSA-N CCc(c(F)c(c(F)c1F)F)c1F Chemical compound CCc(c(F)c(c(F)c1F)F)c1F NBOXZRBYWXQDLY-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N c1ccc(C(c2ccccc2)c2ccccc2)cc1 Chemical compound c1ccc(C(c2ccccc2)c2ccccc2)cc1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention provides a composition comprising at least one dopant, and a polymer containing at least one unit selected from the structure I shown in the specification, wherein M is selected from Fe, Co, or Ni; R1, R2, R3 , R4 and R5 are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C16) alkyl, substituted or unsubstituted (C6-C16) aryl, substituted or unsubstituted (C3-C16) cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, substituted or unsubstituted (C6-C16) aryl condensed with one or more cycloalkyls; 5- to 7- membered heterocycloalkyl group condensed with one or more substituted or unsubstituted aromatic rings or (C3-C16) cycloalkyl condensed with one or more substituted or unsubstituted aromatic rings, substituted or unsubstituted (C1-C16) silyl, cyano, nitro or hydroxyl; n is greater than or equal to 1; x is 0-4; y is 0-5; the dopant is a P-type dopant. The polymers containing and free of dopants can be used to prepare films and electronic devices, such as an organic light emitting diode (OLED).
Description
Technical field
The present invention relates to organometallic polymer composition and method of making the same, and the Organic Light Emitting Diode of being manufactured by this organometallic polymer.
Background technology
OLED (Organic Light Emitting Diode) is photodiode (LED), wherein electroluminescence layer (emissive electroluminescent layer) is the film of organic compound, described organic compound response current and luminous.Many-layer structure that typical OLED has, and generally include tin indium oxide (ITO) anode, and metallic cathode.Several organic layers are clipped between described ito anode and metallic cathode, for example hole injection layer (HIL), hole transmission layer (HTL), luminous material layer (EML), electron transfer layer (ETL), and electron injecting layer (EIL).Inject for the ease of hole, and obtain smooth surface, the hole injection layer (HIL) between ito anode and hole transmission layer is usually desirable.The most normally used HIL material is poly-(3,4-ethylidene dioxy thiophene)/poly-(styrene sulfonic acid) complex compound (PEDOT/PSS).But in the life-span that the OLED being prepared by PEDOT/PSS is short because corrosion demonstrates, described corrosion is induced by the high acidity of PEDOT/PSS.In addition, described PEDOT/PSS solution is usually based on water.When by it during for OLED, in this film, the moisture resistates of trace may cause circuit corrosion, and causes equipment to rot.Therefore, need the HIL material for OLED application, especially non-aqueous HIL composition always.
JP2008/111941A has disclosed a kind of electrochromic device, it is characterized in that being formed at the pair of electrodes structure with transparency electrode on supporting substrate, this transparency electrode is faced with each other its placement by dielectric substrate.Porous electrode (wherein having adsorbed by being oxidized or reducing the electrochromism coloured material developing the color) is formed at least one transparency electrode of this electrode structure centering; Be formed in the transparency electrode that forms this comparative electrode structure with the porous electrode of the ferrocene macromolecular compound with thering is predetermined structure.
CN1786010A has disclosed a kind of photochromic ferrocene two arylene compounds.Described ferrocene two arylene compounds are carrier switching material (carrier switch material), can be as the organic luminous layer of OLED device.
Leung,
chem.Mater., 20,540-552 (2008) has described and has used the composition module of ferrocene as electrochemical polymerization monomer, and the polymkeric substance of being prepared by these monomers is as the purposes of the HIL in OLED.The active part of this HIL is triarylamine.
The reference that is taught in material useful in electron device comprises WO2010/082924 (crosslinkable copper phthalocyanine complex compound), WO2011/120709 (two secondary flat monokaryon transition metal complexes (quadratic planar mononuclear transition metal complexes)), WO2004/041962 (the crosslinkable matrix material of boric acid or boric acid derivatives and organic or organo-metallic part), there is the US2011/0198666 (p-doping agent (Al of matrix polymer, Be or Ir), US2008/073440 (the crosslinkable matrix material of Ir), WO2003/022008 (doped with the organic substrate of metal complex), US2005/0260444 (being engaged to the macrocyclic ligand of metal center), and US2009/0212280 (doped with organic semiconduction matrix of metal complex n-doping agent).
But, as mentioned above, still need the new HIL material for OLED application, especially non-aqueous HIL composition.
Summary of the invention
The invention provides a kind of composition, it comprises at least one doping agent, and contains at least one and be selected from the polymkeric substance of the unit of structure I:
Wherein M is selected from Fe, Co, or Ni;
R
1, R
2, R
3, R
4and R
5be selected from independently of one another hydrogen; Deuterium; Halogen; Replace or unsubstituted (C
1-C
16) alkyl; Replace or unsubstituted (C
6-C
16) aryl; Replace or unsubstituted (C
3-C
16) cycloalkyl; The first Heterocyclylalkyl of 5-to 7-that replace or unsubstituted; Condense replacement or the unsubstituted (C of one or more cycloalkyl
6-C
16) aryl; Condense 5-to 7-unit's Heterocyclylalkyl one or more replacements or unsubstituted aromatic ring or condense (C one or more replacements or unsubstituted aromatic ring
3-C
16) cycloalkyl; Replace or unsubstituted (C
1-C
16) silyl; Cyano group; Nitro; Or hydroxyl;
N is for being more than or equal to 1;
X is 0 to 4; With
Y is 0 to 5.
The present invention also provides a kind of film, and it comprises at least two layers, layer A and a layer B, and its middle level A is formed by composition A, and described composition A comprises the polymkeric substance that contains at least one and be selected from the unit of structure I:
Wherein M is selected from Fe, Co, or Ni;
R
1, R
2, R
3, R
4and R
5be selected from independently of one another hydrogen; Deuterium; Halogen; Replace or unsubstituted (C
1-C
16) alkyl; Replace or unsubstituted (C
6-C
16) aryl; Replace or unsubstituted (C
3-C
16) cycloalkyl; The first Heterocyclylalkyl of 5-to 7-that replace or unsubstituted; Condense replacement or the unsubstituted (C of one or more cycloalkyl
6-C
16) aryl; Condense 5-to 7-unit's Heterocyclylalkyl one or more replacements or unsubstituted aromatic ring or condense C one or more replacements or unsubstituted aromatic ring
3-C
16) cycloalkyl; Replace or unsubstituted (C
1-C
16) silyl; Cyano group; Nitro; Or hydroxyl;
N is for being more than or equal to 1;
X is 0 to 4; With
Y is 0 to 5.
The present invention also provides a kind of electron device, and it comprises the assembly that at least one is formed by composition A, and described composition A comprises the polymkeric substance that contains at least one and be selected from the unit of structure I:
Wherein M is selected from Fe, Co, or Ni;
R
1, R
2, R
3, R
4and R
5be selected from independently of one another hydrogen; Deuterium; Halogen; Replace or unsubstituted (C
1-C
16) alkyl; Replace or unsubstituted (C
6-C
16) aryl; Replace or unsubstituted (C
3-C
16) cycloalkyl; The first Heterocyclylalkyl of 5-to 7-that replace or unsubstituted; Condense replacement or the unsubstituted (C of one or more cycloalkyl
6-C
16) aryl; Condense 5-to 7-unit's Heterocyclylalkyl one or more replacements or unsubstituted aromatic ring or condense (C one or more replacements or unsubstituted aromatic ring
3-C
16) cycloalkyl; Replace or unsubstituted (C
1-C
16) silyl; Cyano group; Nitro; Or hydroxyl;
N is for being more than or equal to 1;
X is 0 to 4; With
Y is 0 to 5.
Brief description of the drawings
Fig. 1 is that polyethylene ferrocene (PVFC) is at CDCl
3in H
1nMR.
Fig. 2 is the cyclic voltammetry curve that is dissolved in the PVFC in dimethyl formamide (DMF), and wherein the hexafluorophosphate of 0.1 volumetric molar concentration (molar) is as supporting ionogen.
Fig. 3 is OLED embodiment 1 (PVFC), OLED embodiment 2 (PVFC+10% doping agent), and the current-voltage curve of comparative example (Polythiophene).
Fig. 4 is OLED embodiment 1 (PVFC), OLED embodiment 2 (PVFC+10% doping agent), and the luminous efficiency curve of comparative example (Polythiophene).
Fig. 5 is OLED embodiment 1 (PVFC), OLED embodiment 2 (PVFC+10% doping agent), and the decay of luminescence curve of comparative example (Polythiophene).
Embodiment
General introduction
The HIL material for OLED application of exploitation at present is roughly limited to organic materials.In order to widen the scope of HIL material, from this scope, can select material standed for to meet the needs of various types of OLED device architectures and application, develop the polymkeric substance in side chain with ferrocene, and as HIL material.Unexpectedly, have been found that these polymkeric substance can be used as HIL material, and combine these polymkeric substance and demonstrate good electroluminescent properties as the OLED of HIL material.
Embodiment
As mentioned above, first aspect, the invention provides a kind of composition, and it comprises at least one doping agent, and contains at least one and be selected from the polymkeric substance of the unit of structure I:
(structure I),
Wherein M is selected from Fe, Co, or Ni;
R
1, R
2, R
3, R
4and R
5be selected from independently of one another hydrogen; Deuterium; Halogen; Replace or unsubstituted (C
1-C
16) alkyl; Replace or unsubstituted (C
6-C
16) aryl; Replace or unsubstituted (C
3-C
16) cycloalkyl; The first Heterocyclylalkyl of 5-to 7-that replace or unsubstituted; Condense replacement or the unsubstituted (C of one or more cycloalkyl
6-C
16) aryl; Condense 5-to 7-unit's Heterocyclylalkyl one or more replacements or unsubstituted aromatic ring or condense (C one or more replacements or unsubstituted aromatic ring
3-C
16) cycloalkyl; Replace or unsubstituted (C
1-C
16) silyl; Cyano group; Nitro; Or hydroxyl;
N is for being more than or equal to 1;
X is 0 to 4; With
Y is 0 to 5.
Composition of the present invention can comprise the combination of two or more embodiments described in the application.
In one embodiment, described doping agent is P-type doping agent.
In one embodiment, the M in structure I is Fe.
In one embodiment, the n of structure I is 1 to 1,000,000, or 1 to 10,000, or 1 to 1,000.
In one embodiment, the x of structure I and y are 0.
In one embodiment, the R of structure I
1, R
2, R
3, R
4and R
5in at least one halogen be that fluorine or at least two s' halogen is that fluorine or at least three s' halogen is fluorine, or all halogens are all fluorine.
In one embodiment, in said composition the amount of polymkeric substance be 1 % by weight (wt%) to 99wt%, or 50wt% to 99wt%, or 70wt% to 99wt%, based on the weight of composition.
In one embodiment, said composition is made up of polymkeric substance and the P-type doping agent of structure I substantially.
In one embodiment, the doping agent of said composition is organometallic compound or organic metal salt.
In one embodiment, described doping agent is the organic metal salt that contains at least one phenyl.In another embodiment, the anionic group of this salt comprises boron atom.
In one embodiment, described organic metal salt has and is selected from one of following structure:
Or its combination.
In one embodiment, described organic metal salt has following structure:
In one embodiment, in composition the amount of doping agent be 1 % by weight (wt%) to 99wt%, or 1wt% to 50wt%, or 1wt% to 30wt%, based on the weight of composition.
In one embodiment, in composition, the amount of polymkeric substance is 70 wt% to 99 wt%, and in composition, the amount of P-type doping agent is 1wt% to 30wt%, all weight based on said composition.
Composition of the present invention can comprise the combination of two or more embodiments described in the application.
The present invention also provides a kind of film, and it comprises the layer that at least one is formed by the present composition of one or more embodiments described in the application.
The present invention also provides a kind of electron device, and it comprises the assembly that at least one is formed by the present composition of one or more embodiments described in the application.
Second aspect, the present invention also provides a kind of film, and described film comprises at least two-layer, layer A and a layer B, its middle level A is formed by composition A, and described composition A comprises the polymkeric substance that contains at least one and be selected from the unit of structure I:
Wherein M is selected from Fe, Co, or Ni;
R
1, R
2, R
3, R
4and R
5be selected from independently of one another hydrogen; Deuterium; Halogen; Replace or unsubstituted (C
1-C
16) alkyl; Replace or unsubstituted (C
6-C
16) aryl; Replace or unsubstituted (C
3-C
16) cycloalkyl; The first Heterocyclylalkyl of 5-to 7-that replace or unsubstituted; Condense replacement or the unsubstituted (C of one or more cycloalkyl
6-C
16) aryl; Condense 5-to 7-unit's Heterocyclylalkyl one or more replacements or unsubstituted aromatic ring or condense (C one or more replacements or unsubstituted aromatic ring
3-C
16) cycloalkyl; Replace or unsubstituted (C
1-C
16) silyl; Cyano group; Nitro; Or hydroxyl;
N is for being more than or equal to 1;
X is 0 to 4; With
Y is 0 to 5.
Film of the present invention can comprise the combination of two or more embodiments described in the application.
In one embodiment, layer B is hole transmission layer.
In one embodiment, composition A comprise 1 to 99 % by weight (wt%) at least one contain at least one and be selected from the polymkeric substance of the unit of structure I, based on the weight of composition.In another embodiment, composition A comprises at least one polymkeric substance of 50 to 99wt%, and described polymkeric substance contains at least one and be selected from the unit of structure I, based on the weight of composition.In another embodiment, composition A comprise 70 to 99wt% at least one contain at least one and be selected from the polymkeric substance of the unit of structure I, based on the weight of composition.
In one embodiment, the M of the structure I of the polymkeric substance of composition A is Fe.
In one embodiment, the n of the structure I of the polymkeric substance of composition A is 1 to 1,000, and the x of the structure I of the polymkeric substance of composition A and y are 0.
In one embodiment, layer A contacts with layer B.
In one embodiment, this film also comprises luminescent layer.
In one embodiment, the thickness of layer A is 5nm to 500nm, or 5nm to 100nm, or 5nm to 50nm, and the thickness of layer B is 5nm to 500nm, or 5nm to 100nm, or 5nm to 50nm.
In one embodiment, composition A also comprises P-type doping agent.In another embodiment, this doping agent is organometallic compound or organic metal salt.
In one embodiment, described doping agent is the organic metal salt that contains at least one phenyl.In another embodiment, the anionic group of this salt comprises boron atom.In another embodiment, described organic metal salt has and is selected from one of following structure:
In one embodiment, described organic metal salt has following structure:
In one embodiment, in composition A the amount of doping agent be 1 % by weight (wt%) to 99wt%, or 1wt% to 50wt%, or 1wt% to 30wt%, based on the weight of composition.
Film of the present invention can comprise the combination of two or more embodiments described in the application.
The present invention also provides a kind of electron device, and it comprises the film formed layer of at least one the present invention by one or more embodiments described in the application.
The third aspect, the present invention also provides a kind of electron device, and it comprises the assembly that at least one is formed by composition A, and described composition A comprises the polymkeric substance that contains at least one and be selected from the unit of structure I:
Wherein M is selected from Fe, Co, or Ni;
R
1, R
2, R
3, R
4and R
5be selected from independently of one another hydrogen; Deuterium; Halogen; Replace or unsubstituted (C
1-C
16) alkyl; Replace or unsubstituted (C
6-C
16) aryl; Replace or unsubstituted (C
3-C
16) cycloalkyl; The first Heterocyclylalkyl of 5-to 7-that replace or unsubstituted; Condense replacement or the unsubstituted (C of one or more cycloalkyl
6-C
16) aryl; Condense 5-to 7-unit's Heterocyclylalkyl one or more replacements or unsubstituted aromatic ring or condense (C one or more replacements or unsubstituted aromatic ring
3-C
16) cycloalkyl; Replace or unsubstituted (C
1-C
16) silyl; Cyano group; Nitro; Or hydroxyl;
N is for being more than or equal to 1;
X is 0 to 4; With
Y is 0 to 5.
Electron device of the present invention can comprise the combination of two or more embodiments described in the application.
In one embodiment, composition A also comprises P-type doping agent.In another embodiment, described doping agent is organometallic compound or organic metal salt.
In one embodiment, described doping agent is the organic metal salt that comprises at least one phenyl.In another embodiment, the anionic group of described salt comprises boron atom.In another embodiment, described organic metal salt has and is selected from one of following structure:
Or its combination.
In one embodiment, described organic metal salt has following structure:
In one embodiment, the amount of the doping agent in composition A be 1 % by weight (wt%) to 99wt%, or 1wt% to 50wt%, or 1wt% to 30wt%, based on the weight of composition.
In one embodiment, the M of the structure I of the polymkeric substance of composition A is Fe.
In one embodiment, the n of the structure I of the polymkeric substance of composition A is 1 to 1,000, and the x of the structure I of the polymkeric substance of composition A and y are 0.
In one embodiment, described electron device also comprises the first electrode.
In one embodiment, described electron device also comprises the second electrode being placed on described the first electrode.
In one embodiment, described electron device also comprises the organic layer being placed between described the first and second electrodes.
In one embodiment, described at least one assembly being formed by composition A of described electron device is organic layer, and described organic layer is placed between described the first and second electrodes.
In one embodiment, described electron device also comprises second layer B.
In one embodiment, layer B is hole transmission layer.
In one embodiment, layer A contacts with layer B.
In one embodiment, described electron device also comprises luminescent layer.
In one embodiment, the thickness of layer A is 5nm to 50nm, and the thickness of layer B is 5nm to 50nm.
In one embodiment, described electron device is OLED (organic luminescent device, Organic Light Emitting Device).
In one embodiment, composition of the present invention can comprise the combination of two or more embodiments described in the application.
In one embodiment, film of the present invention can comprise the combination of two or more embodiments described in the application.
In one embodiment, electron device of the present invention can comprise the combination of two or more embodiments described in the application.
The polymkeric substance that contains structure I
Following embodiment is applicable to above-described all three aspects of the present invention.
This polymkeric substance comprises that at least one is selected from the unit of structure I:
(structure I),
Wherein M, R
1, R
2, R
3, R
4and R
5, n, x and y as above define (referring to summary of the invention).
This polymkeric substance can comprise two or more embodiments described in the application.
In one embodiment, the R of structure I
1one of following: hydrogen; Deuterium; Halogen; Replace or unsubstituted C
1-C
16alkyl; Replace or unsubstituted C
6-C
16aryl; Replace or unsubstituted C
3-C
16cycloalkyl; The first Heterocyclylalkyl of 5-to 7-that replace or unsubstituted; Or hydroxyl.In another embodiment, the R of structure I
1one of following: hydrogen; Halogen; Replace or unsubstituted C
1-C
16alkyl; Replace or unsubstituted C
6-C
16aryl.
In one embodiment, the R of structure I
2one of following: hydrogen; Deuterium; Halogen; Replace or unsubstituted C
1-C
16alkyl; Replace or unsubstituted C
6-C
16aryl; Replace or unsubstituted C
3-C
16cycloalkyl; The first Heterocyclylalkyl of 5-to 7-that replace or unsubstituted; Or hydroxyl.In another embodiment, the R of structure I
2one of following: hydrogen; Halogen; Replace or unsubstituted C
1-C
16alkyl; Replace or unsubstituted C
6-C
16aryl.
In one embodiment, the R of structure I
3one of following: hydrogen; Deuterium; Halogen; Replace or unsubstituted C
1-C
16alkyl; Replace or unsubstituted C
6-C
16aryl; Replace or unsubstituted C
3-C
16cycloalkyl; The first Heterocyclylalkyl of 5-to 7-that replace or unsubstituted; Or hydroxyl.In another embodiment, the R of structure I
3one of following: hydrogen; Halogen; Replace or unsubstituted C
1-C
16alkyl; Replace or unsubstituted C
6-C
16aryl.
In one embodiment, the R of structure I
4one of following: hydrogen; Deuterium; Halogen; Replace or unsubstituted C
1-C
16alkyl; Replace or unsubstituted C
6-C
16aryl; Replace or unsubstituted C
3-C
16cycloalkyl; The first Heterocyclylalkyl of 5-to 7-that replace or unsubstituted; Or hydroxyl.In another embodiment, the R of structure I
4one of following: hydrogen; Halogen; Replace or unsubstituted C
1-C
16alkyl; Replace or unsubstituted C
6-C
16aryl.
In one embodiment, the R of structure I
5one of following: hydrogen; Deuterium; Halogen; Replace or unsubstituted C
1-C
16alkyl; Replace or unsubstituted C
6-C
16aryl; Replace or unsubstituted C
3-C
16cycloalkyl; The first Heterocyclylalkyl of 5-to 7-that replace or unsubstituted; Or hydroxyl.In another embodiment, the R of structure I
5one of following: hydrogen; Halogen; Replace or unsubstituted C
1-C
16alkyl; Replace or unsubstituted C
6-C
16aryl.
In one embodiment, n is 1 to 1,000,000, further, and 1 to 100,000, further, 1 to 10,000, and further, 1 to 1,000.
In one embodiment, x is 0, or 1, or 2, or 3, or 4.
In one embodiment, x is 0.
In one embodiment, y is 0, or 1, or 2, or 3, or 4, or 5.
In one embodiment, y is 0.
In one embodiment, this polymkeric substance contains at least one unit that is selected from following structure:
Or its combination, and wherein Me is methyl, and M, R
1, R
2, R
3, R
4, R
5, x, y and n are as previously mentioned.
In one embodiment, this polymkeric substance contains at least one and is selected from the unit of following structure:
Or its combination, and wherein Me is methyl, and M, R
1, R
2, R
3, R
4, R
5, x, y and n are as previously mentioned.
In one embodiment, this polymkeric substance comprises at least one unit that is selected from following structure:
Or its combination, and wherein Me is methyl, and n is for being more than or equal to 1, or 1 to 1,000,000, or 1 to 100,000, or 1 to 10,000, or 1 to 1,000.
In one embodiment, this polymkeric substance contains at least one unit that is selected from following structure:
or its combination, and
Wherein Me is methyl, and n is for being more than or equal to 1, further, and 1 to 1,000,000, further, 1 to 100,000, further, 1 to 10,000, and further, 1 to 1,000.
In one embodiment, this polymkeric substance contains at least one unit that is selected from following structure
Wherein Me is methyl, and n is for being more than or equal to 1, further, and 1 to 1,000,000, further, 1 to 100,000, further, 1 to 10,000, and further, 1 to 1,000.
" Heterocyclylalkyl " and similar terms refer to a kind of cycloalkyl, and it contains at least one heteroatoms for cycloalkyl skeletal atom, and carbon atom is for remaining cycloalkyl skeletal atom.Heteroatoms comprises for example B, N, O, S, P (=O), Si and P.
" heteroaryl " and similar terms refer to a kind of aryl, and it contains at least one heteroatoms for aryl skeletal atom, and carbon atom is for remaining aryl skeletal atom.Heteroatoms comprises for example B, N, O, S, P (=O), Si and P.
Some examples of the group replacing comprise following deuterium, halogen, tool is with or without halogenic substituent (Cl-C30) alkyl, (C6-C30) aryl, tool is with or without (C3-C30) heteroaryl of (C6-C30) aryl substituent, contain one or more for example B that are selected from, N, O, S, P (=O), the first Heterocyclylalkyl of heteroatomic 5-to 7-of Si and P, condense 5-to the 7-unit Heterocyclylalkyl of one or more aromatic rings, (C3-C30) cycloalkyl, condense (C6-C30) cycloalkyl of one or more aromatic rings, three (Cl-C30) alkyl silyl, two (Cl-C30) alkyl (C6-C30) aryl silyl, three (C6-C30) aryl silyl, adamantyl, (C7-C30) bicyclic alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, cyano group, carbazyl, NR
21r
22, BR
23r
24, PR
25r
26, P (=O) R
27r
28(wherein R
21to R
28represent independently (Cl-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl), (Cl-C30) alkyl (C6-C30) aryl, (Cl-C30) alkoxyl group, (Cl-C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) carbalkoxy, (C1-C30) alkyl-carbonyl, (C6-C30) aryl carbonyl, (C6-C30) aryloxy carbonyl, (C1-C30) alkoxycarbonyloxy, (C1-C30) alkyl-carbonyl oxygen base, (C6-C30) aryl carbonyl oxygen base, (C6-C30) aryloxy carbonyl oxygen base, carboxyl, nitro and hydroxyl, or adjacent substituting group is joined together to form ring.
Definition
Point out unless had on the contrary, context hint, or the convention of this area, otherwise all umbers and percentage ratio are all based on weight.For the object of patent practice, the content of any patent of mentioning, patent application or publication is all by reference to by their whole the application of being incorporated to (or by reference to being incorporated to its United States version of equal value), especially disclosing for synthetic technology, definition (reach with the disclosure in any definition of specifically providing there is no inconsistent degree), and the knowledge of this area.
" polymkeric substance " and similar terms refer to the compound by prepared by monomer (no matter being identical or different types) polymerization.Thus, general term polymer has contained term homopolymer and (has been used to refer to for the polymkeric substance by only prepared by the monomer of a type, the impurity that it will be appreciated that trace can be attached in this polymer architecture and in this mass polymer), and the term interpretation defining below.Polymkeric substance can contain the remainder catalyst resistates of trace.
" interpretation " and similar terms refer to the polymkeric substance by prepared by least two kinds of dissimilar monomer polymerizations.Therefore, general term interpretation comprises multipolymer (being used in reference to the polymkeric substance of being prepared by two kinds of dissimilar monomers), and by more than 2 kinds of polymkeric substance prepared by dissimilar monomer.
" comprise ", " containing ", " having " and their derivative words be not intended to get rid of and have any other component, step or method, and no matter whether concrete disclosure it.For fear of any query, by using term " to comprise " that all compositions that require all can contain any other additive, assistant agent or compound, be no matter polymerization or other, otherwise can point out on the contrary.On the contrary, term " substantially by ... composition " has been got rid of any other component from the scope of any follow-up record, step or method, and do not get rid of for operability unessential those.Term " by ... composition " get rid of any component, step or the method not describing or enumerate.
" hole transmission layer (HTL) " and similar terms refer to the layer that the material of transporting holes is made.High hole mobility is recommended.HTL is for helping to block the passage (block passage) of the electronics transmitting by luminescent layer.Conventionally need little electron affinity to block electronics.HTL should have ideally larger triplet state and block exciton from adjacent EML layer migration.The example of HTL compound includes but not limited to two (p-tolyl) aminophenyl] hexanaphthene (TPAC), N, N-phenylbenzene-N, N-bis-(3-aminomethyl phenyl)-1,1-phenylbenzene-4,4-diamines (TPD), and N, N '-phenylbenzene-N, N '-bis-(1-naphthyl)-(1,1 '-phenylbenzene)-4,4 '-diamines (NPB).
" luminescent layer " and similar terms refer to the layer being made up of main body (host) and doping agent.This material of main part can be ambipolar (bipolar) or unipolar (unipolar), and can use separately or use by combining two or more material of main parts.The photoelectric property of material of main part can be different from the type of the doping agent (phosphorescence or fluorescence) using.For fluorescent dopants, auxiliary material of main part should have good spectra overlapping between the absorption of doping agent and main body luminous, thereby induces good Foester to be transferred to doping agent.For phosphorescent dopants, auxiliary material of main part should have high triplet energy state, thereby limits the triplet state of this doping agent.
" doping agent " and similar terms refer to a kind of electron acceptor(EA) or to body, it can increase the electroconductibility of the organic layer of organic electronic devices in the time being added into organic layer as additive.Aspect organic semi-conductor electroconductibility, by doping, can affect equally organic semiconductor.This organic semiconduction substrate material can be made up of the compound with electron donor(ED) character, or is made up of the compound with electron acceptor(EA) character.
" P-type doping agent " and similar terms refer to a kind of electron acceptor(EA), and it can increase the electroconductibility of the organic layer of organic electronic devices in the time being added into organic layer as additive.Aspect organic semi-conductor electroconductibility, by doping, equally can strong effect organic semiconductor.This organic semiconduction substrate material can be made up of the compound with good electron donor(ED) character, or is made up of the compound with good electron acceptor(EA) character.For the electron donor(ED) material that adulterates, strong electron acceptor(EA) as four cyano quinone bismethane (tetracyanoquinonedimethane, TCNQ) or 2,3,5,6-tetrafluoro four cyano-Isosorbide-5-Nitrae-benzoquinones bismethane (F4TCNQ) be known.By electronic transmission process, these produce so-called hole in electron donor(ED) shape base mateiral.
Experiment
I. material
In table 1, provide the material using in following examples.
Table 1: material used in embodiment
*SCRC=Sinopharm?Chemical?Reagent?Co.，Ltd。
II. polymkeric substance is synthetic
Prepare ferrocenyl methyl ketone
At 0 DEG C, to AlCl
3in (35g, 0.26mol) solution in 300mL methylene dichloride, dropwise add the solution of Acetyl Chloride 98Min. (18.5g, 0.236mol) in 200mL methylene dichloride, and make this solution be warming up to room temperature, and stirring is until AlCl
3dissolve.Then dropwise add this solution to ferrocene (40g, 0.215mol) in the solution of 200mL methylene dichloride at 0 DEG C.After adding, by this solution stirring at room temperature 3 hours.After reaction, this solution is slowly added in frozen water.By this mixture (organic solution) water, 5wt%NaHCO
3(100mL) washing, through anhydrous MgSO
4dry, and filter.Concentrated filtrate, then obtains corresponding product by silicon-dioxide column chromatography.
1H?NMR(CDCl
3，ppm):δ=4.775(2H，H-Cp)，4.506(2H，H-Cp)，4.208(5H，H-Cp)，2.400(3H，CH
3-)。
Preparation 1-(ferrocenyl) ethanol
In the solution of 100mL ethanol, slowly add sodium borohydride (0.8g, 2.1mmol) to ferrocenyl methyl ketone (1g, 4.4mmol), and then this solution is refluxed 30 minutes.Then, add 20mL6N sodium hydroxide, and this mixture is continued to reflux 15 minutes.This solution is concentrated by remove desolventizing under rotary evaporation.Then use ether extracted residues, then use anhydrous magnesium sulfate drying.By this solution filter, and then remove desolventizing by rotary evaporation.Product is further purified by silicon-dioxide column chromatography.
1H?NMR(CDCl
3，ppm):δ=4.548(1H，CH
3-CH-OH)，4.195(9H，H-Cp)，1.848(1H，CH
3-CH-OH)，1.431(3H，CH
3-)。
Prepare ethene ferrocene
By this 1-(ferrocenyl) ethanol (0.92g, 4mmol, 230), anhydrous cupric sulfate (4.788g, 30mmol, 159.6), and 10mg quinhydrones is dissolved in 100ml toluene.Mixture is refluxed 45 minutes, be then cooled to room temperature.After filtering, under vacuum, remove desolventizing.Use ether extracted residues, and use anhydrous magnesium sulfate drying.Filter this solution, and then remove desolventizing by rotary evaporation.Be further purified product by silicon-dioxide column chromatography.
1H?NMR(CDCl
3，ppm):δ=6.453(1H，-CH=CH
2)，5.354(1H，-CH=CH
2)，5.030(1H，-CH=CH
2)，4.347(2H，H-Cp)，4.199(2H，H-Cp)，4.097(5H，H-Cp)。
The polyreaction of ethene ferrocene
Ethene ferrocene (1.00g, 4.7mmol) and 10mg Diisopropyl azodicarboxylate (AIBN) are heated 3 hours at 80 DEG C in Pyrex pipe that find time, sealing.After initial melted, observing immediately viscosity increases, and after one hour, the content of this pipe is motionless.By polymer product be dissolved in tetrahydrofuran (THF) (THF) (10mL) in.Then this polymers soln is dropwise added in the methyl alcohol (200mL) stirring, and by filtering the polymkeric substance of collecting precipitation, then be dissolved in (30mL) in THF, and in methyl alcohol (200mL), precipitate again.Then extract and use methyl alcohol that the polymkeric substance of this precipitation is further purified to 48 hours by Soxhlet.Then by the fibrous product (PVFC) of this yellow dry 0.90g (90%) final product that obtains in a vacuum.Molecular weight uses GPC to characterize, Mw=6.91*10
4, Mn=1.38*10
4, PDI=5.01.
1h NMR (CDCl
3, ppm): δ=4.179 (2H, H-Cp), 3.512 (7H, H-Cp), 1.066 (3H ,-CH-CH
2-), referring to Fig. 1.
III. characterize and measure
Gpc analysis
Sample is dissolved in tetrahydrofuran (THF)/FA (0.5wt%), and concentration is 2mg/mL.It is transparent that sample demonstrates.Detailed experiment condition is as follows: instrument: Agilent1200; Post: the B post (7.8x300mm) of two mixing of series connection; Column temperature: 40 DEG C; Moving phase: tetrahydrofuran (THF)/FA (0.5%); Flow velocity: 1.0mL/min; Volume injected: 100 μ L; Detector: Agilent specific refractory power detector, 40 DEG C; Software: Agilent GPC software, and from double injection, collect data; Working curve: the narrow standard specimen of PL polystyrene (Part No.:2010-0101), its molecular weight is that Isosorbide-5-Nitrae 80 is to 3,787,000g/mol.
NMR measures
In room temperature, the sample of about 20mg is dissolved in 0.6mL deuterate solvent, thereby obtains uniform solution.In room temperature, on Bruker AVANCE III400MHz spectrophotometer, obtain NMR data.Use by " 5mm BBI probe ".Chemical shift provides with the part every 1,000,000 parts (ppm) with respect to tetramethylsilane (TMS).
Cyclic voltammetry is measured
Cyclic voltammetry is carried out in room temperature on CHI760D electrochemistry worktable, wherein use three conventional electrode configurations, by Pt plate (diameter: 2mm) working electrode, Pt line counter electrode (wire counter electrode), and Hg/Hg2+ reference electrode composition.DMF is as solvent, and support ionogen is 0.1M hexafluorophosphate.
Polymeric film (no dopant)
Atomic force microscope (AFM)
Apply the surfaceness that AFM makes the HIL film of the visual and definite spin coating of this configuration of surface.This AFM measures on the Dimension V instrument of producing at Veeco by the pattern of rapping (tapping mode) and carries out.In AFM measures, the deflection of cantilever also produces depth curve (depth profile) (or altitude curve) and shows the vertical missing in nanometer range along this surface.The amplitude (A) of vertical missing is used for the roughness of gauging surface.Ra and Rq are that the amplitude parameter of the most often use carrys out description surface roughness.Ra is the mathematic(al) mean of absolute amplitude value, and Rq is the rootmean-square of amplitude, and it is described as:
Wherein Ai is the amplitude (height or the degree of depth) of pixel i in afm image (referring to lip-deep point), and n is the sum of pixel in this image.
In order to determine the thickness of film of spin coating, take off a part of this film from this ITO base material with sharp blade, then scan by this cantilever.Disclose the thickness of this film by the gap between two parts.
The surfaceness of the PVFC of the upper spin coating of ITO characterizes by AFM.
Mean roughness provides in table 2.On ITO, after spin coating PVFC, roughness is improved to the Rq of 1.02nm from 5.3 nanometers (nm).
Table 2: the mean roughness of the PVFC of spin coating
This HOMO (highest occupied molecular orbital) level is used cyclic voltammetry test.The CV-curve of PVFC in DMF solution is shown in Fig. 5.Can estimate that from oxidation peak this HOMO is-5.1～-5.2 electron-volts (eV).
IV. composition
PVFC by (23 DEG C, normal atmosphere) blend 1 gram (g) under envrionment conditions and 0.1g trityl group four-(pentafluorophenyl group)-borate (P-doping agent) and prepare composition.
V.OLED manufactures and test
Manufacture
Clean and there is the long-pending glass baseplate (20mm × 20mm) of " 3mm × 3mm " ito surface with solvent (ethanol, acetone, Virahol order) and oxygen plasma.This ITO layer is that 150nm is thick.In the glove box of filling at nitrogen, by HIL methyl-phenoxide/toluene with the solution spin coating (speed: 2000rpm) in the volume ratio of 9:1 (15mg/mL, with 0.5 micro-tetrafluoroethylene (PTFE) injection filter filter) on ito glass base material.The film of spin coating is annealed 20 minutes at 150 DEG C.The thickness of the film of this annealing is 10-100nm.Then at about 1*10
-7under the vacuum of holder, these base materials are transferred in hot vaporizer.Sequential aggradation is with lower floor: HTL1, HTL2, and Fl Blue EML, ETL and quinoline lithium (Lithium quinolate, Liq), its thickness is respectively 5nm, 25nm, 20nm, 30nm and 1nm.The sedimentation rate of organic layer remains on 0.05 to 0.1nm/s.Aluminium negative electrode deposits with 0.5nm/s.The active region of OLED is " 3mm × 3mm ", limits by the shadow mask board for cathodic deposition.This glass substrate (20mm × 20mm) can derive from Samsung Corning, wherein ITO layer thickness be 1,500 dust (
).Finally, these OLED (providing in table 3) were isolated sealings before test.This OLED has following general structure:
HIL(
)/HTL1(
)/HTL2(
)/Fl?Blue?EML(
)/Alq3(
)/Liq(
)。
Table 3: sample OLED
| Embodiment | HIL |
| OLED embodiment | |
| 1 | |
| OLED embodiment | |
| 2 | PVFC+10% doping agent |
| OLED comparative example 1 | Polythiophene |
VI. test
Current-voltage-brightness (J-V-L) of this OLED characterizes use source measuring unit (KEITHLY238) luminometer (Luminescence meter) (MINOLTA CS-100A) and carries out.The EL spectrum of OLED device is collected by the CCD spectrograph of calibration.OLED embodiment 1 and 2 and the current-voltage curve of OLED comparative example 1, luminous efficiency curve, and decay of luminescence curve is shown in Fig. 3, in 4 and 5.Performance data is summarized in table 4.As can be seen from Table 4: the turn-on voltage (at the voltage of 1000nit) of PVFC is close to the comparative example based on Polythiophene; After with the doping of P-doping agent, the life-span of PVFC is longer than the comparative example based on Polythiophene; The current efficiency of PVFC is identical with the comparative example based on Polythiophene.In a word, the OLED performance based on PVFC compared with comparative example based on Polythiophene quite or even better.
The performance of table 4.OLED device is summed up
Be intended that particularly and the invention is not restricted to the contained embodiment of the application and explanation, but comprise the improved form of those embodiments within the scope of the appended claims, comprise the combination of the various piece of embodiment and the element of different embodiments.
Claims (15)
1. a composition, it comprises at least one doping agent, and contains at least one and be selected from the polymkeric substance of the unit of structure I:
Wherein M is selected from Fe, Co, or Ni;
R
1, R
2, R
3, R
4and R
5be selected from independently of one another hydrogen; Deuterium; Halogen; Replace or unsubstituted (C
1-C
16) alkyl; Replace or unsubstituted (C
6-C
16) aryl; Replace or unsubstituted (C
3-C
16) cycloalkyl; The first Heterocyclylalkyl of 5-to 7-that replace or unsubstituted; Condense replacement or the unsubstituted (C of one or more cycloalkyl
6-C
16) aryl; Condense 5-to 7-unit's Heterocyclylalkyl one or more replacements or unsubstituted aromatic ring or condense (C one or more replacements or unsubstituted aromatic ring
3-C
16) cycloalkyl; Replace or unsubstituted (C
1-C
16) silyl; Cyano group; Nitro; Or hydroxyl;
N is for being more than or equal to 1;
X is 0 to 4; With
Y is 0 to 5.
2. the composition of claim 1, wherein said doping agent is P-type doping agent.
3. the composition of claim 1, wherein M is Fe.
4. the composition of any one in aforementioned claim, wherein n is 1 to 1,000, and x and y are 0.
5. the composition of any one in claims 1 to 3, wherein said polymkeric substance comprises at least one unit that is selected from following structure:
6. the composition of any one in claim 1-3, wherein the polymkeric substance of said composition comprises at least one unit that is selected from following structure:
7. the composition of any one in claim 1-3, wherein said P-type doping agent is organometallic compound or organic metal salt.
8. the composition of claim 7, wherein said P-type doping agent has and is selected from one of following structure:
9. the composition of any one in claim 1-3, in wherein said composition, the amount of polymkeric substance is 70wt% to 99wt%, and in described composition, the amount of P-type doping agent is 1wt% to 30wt%, all weight based on said composition.
10. a film, it comprises at least two-layer, layer A and a layer B, its middle level A is formed by composition A, and described composition A comprises the polymkeric substance that contains at least one and be selected from the unit of structure I:
Wherein M is selected from Fe, Co, or Ni;
R
1, R
2, R
3, R
4and R
5be selected from independently of one another hydrogen; Deuterium; Halogen; Replace or unsubstituted (C
1-C
16) alkyl; Replace or unsubstituted (C
6-C
16) aryl; Replace or unsubstituted (C
3-C
16) cycloalkyl; The first Heterocyclylalkyl of 5-to 7-that replace or unsubstituted; Condense replacement or the unsubstituted (C of one or more cycloalkyl
6-C
16) aryl; Condense 5-to 7-unit's Heterocyclylalkyl one or more replacements or unsubstituted aromatic ring or condense (C one or more replacements or unsubstituted aromatic ring
3-C
16) cycloalkyl; Replace or unsubstituted (C
1-C
16) silyl; Cyano group; Nitro; Or hydroxyl;
N is for being more than or equal to 1;
X is 0 to 4; With
Y is 0 to 5.
The film of 11. claims 10, its middle level B is hole transmission layer.
12. 1 kinds of electron devices, it comprises the assembly that at least one is formed by composition A, described composition A comprises the polymkeric substance that contains at least one and be selected from the unit of structure I:
(structure I),
Wherein M is selected from Fe, Co, or Ni;
R
1, R
2, R
3, R
4and R
5be selected from independently of one another hydrogen; Deuterium; Halogen; Replace or unsubstituted (C
1-C
16) alkyl; Replace or unsubstituted (C
6-C
16) aryl; Replace or unsubstituted (C
3-C
16) cycloalkyl; The first Heterocyclylalkyl of 5-to 7-that replace or unsubstituted; Condense replacement or the unsubstituted (C of one or more cycloalkyl
6-C
16) aryl; Condense 5-to 7-unit's Heterocyclylalkyl one or more replacements or unsubstituted aromatic ring or condense (C one or more replacements or unsubstituted aromatic ring
3-C
16) cycloalkyl; Replace or unsubstituted (C
1-C
16) silyl; Cyano group; Nitro; Or hydroxyl;
N is for being more than or equal to 1;
X is 0 to 4; With
Y is 0 to 5.
The electron device of 13. claims 12, also comprises the first electrode.
The electron device of 14. claims 13, also comprises the second electrode being placed on described the first electrode.
The electron device of 15. claims 14, wherein said at least one assembly being formed by composition A is organic layer, it is placed between described the first and second electrodes.
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