Interlayer for electronic devices
View Patent ↗Embodiments in accordance with the present invention provide for the use of polycycloolefins in electronic devices and more specifically to the use of such polycycloolefins as interlayers applied to fluoropolymer layers used in the fabrication of electronic devices, the electronic devices that encompass such polycycloolefin interlayers and processes for preparing such polycycloolefin interlayers and electronic devices.
1. An interlayer that is in direct contact with a dielectric layer in an organic electronic device, said interlayer consisting essentially of a polycycloolefinic polymer, or a polymer composition containing a polycycloolefinic polymer, said polycycloolefinic polymer comprising a first type of repeating unit in accordance with formula I:
wherein Z is selected from —CH 2 —, —CH 2 —CH 2 — or —O—, m is an integer from 0 to 5, each of R 1 , R 2 , R 3 and R 4 are independently selected from H, a C 1 to C 25 hydrocarbyl, a C 1 to C 25 halohydrocarbyl or a C 1 to C 25 perhalocarbyl group or one of R 1 , R 2 , R 3 and R 4 has a pendant crosslinkable group and the other R 1 , R 2 , R 3 and R 4 are defined above, and
the dielectric layer comprises a fluoropolymer.
2. The interlayer of claim 1 , wherein m is 0 or 1.
3. The interlayer of claim 1 , wherein one of R 1 , R 2 , R 3 and R 4 has a pendant crosslinkable group.
4. The interlayer of claim 3 , wherein the pendant crosslinkable group is a latent crosslinkable group.
5. The interlayer of claim 3 , wherein the pendant crosslinkable group is a maleimide, a 3-monoalkylmaleimide, a 3,4-dialkylmaleimide, an epoxy, a vinyl, an acetyl, an indenyl, a cinnamate or a coumarin group, or the pendant crosslinkable group comprises a substituted or unsubstituted maleimide portion, an epoxide portion, a vinyl portion, a cinnamate portion or a coumarin portion.
6. The interlayer of claim 3 , wherein the first type of repeating unit having a pendant crosslinkable group is derived from any one of the following monomers:
where n is an integer from 1 to 8, Q 1 and Q 2 are each independently of one another —H or —CH 3 , and R′ is —H or —OCH 3 .
7. The interlayer of claim 3 , wherein the polycycloolefinic polymer comprises a second type of repeating unit, such second type being distinct from the first type.
8. The interlayer of claim 1 , wherein the polycycloolefinic polymer further comprises one or more types of repeating units in accordance with formula II
wherein Z is selected from —CH 2 —, —CH 2 —CH 2 — or —O—, m is an integer from 0 to 5, each of R 5 , R 6 , R 7 and R 8 are independently selected from H, a C 1 to C 25 hydrocarbyl, a C 1 to C 25 halohydrocarbyl or a C 1 to C 25 perhalocarbyl group, and wherein the repeating units of formula II are distinct from the repeating units of formula I.
9. The interlayer of claim 1 , wherein the polycycloolefinic polymer comprises two, three or more than three different types of repeating units in accordance with formula I or II
wherein Z is selected from —CH 2 —, —CH 2 —CH 2 — or —O—, in is an integer from 0 to 5, each of R 1 , R 2 , R 3 and R 4 and R 5 , R 6 , R 7 and R 5 are independently selected from H, a C 1 to C 25 hydrocarbyl, a C 1 to C 25 halohydrocarbyl or a C 1 to C 25 perhalocarbyl group, and wherein the repeating units of formula I are distinct from the repeating units of formula II.
10. The interlayer of claim 1 , wherein the polymer composition comprises a blend of a first polycycloolefinic polymer and a second polycycloolefinic polymer.
11. The interlayer of claim 10 , wherein the polymer composition is a blend of a first polycycloolefinic polymer having one or more types of repeating units of formula I, and a second polycycloolefinic polymer having one or more types of repeating units of formula II
wherein Z is selected from —CH 2 —, —CH 2 —CH 2 — or —O—, m is an integer from 0 to 5, each of R 1 , R 2 , R 3 and R 4 and R 5 , R 6 , R 7 and R 8 are independently selected from H, a C 1 to C 25 hydrocarbyl, a C 1 to C 25 halohydrocarbyl or a C 1 to C 25 perhalocarbyl group, and wherein the repeating units of formula I are distinct from the repeating units of formula II.
12. The interlayer of claim 1 , wherein the polymer composition further comprises one or more of a solvent, a crosslinking agent, an optional reactive solvent, stabilizer, a UV sensitizer and a thermal sensitizer.
13. The interlayer of claim 1 , wherein the polymer or polymer composition contains one or more repeating units having a crosslinkable group, and the interlayer further comprises an adhesion promoter which is a compound comprising a surface-active functional group and a crosslinkable functional group that is capable of reacting with the said crosslinkable group of the repeating unit of the polymer or polymer composition.
14. The interlayer of claim 13 , wherein the adhesion promoter is a compound of formula III
G-A′-P III
wherein G is a surface-active group, A′ is a spacer group or a single bond, and P is a crosslinkable group.
15. The interlayer of claim 14 , wherein the surface active group of the adhesion promoter is of formula —SiR 12 R 13 R 14 , or of formula —NH—SiR 12 R 13 R 14 , wherein R 12 , R 13 and R 14 are selected from halogen, silazane, C 1 -C 12 -alkoxy, C 1 -C 12 -alkylamino, optionally substituted C 5 -C 20 -aryloxy and optionally substituted C 2 -C 20 -heteroaryloxy, and wherein one or two of R 12 , R 13 and R 14 may also denote C 1 -C 12 -alkyl, optionally substituted C 5 -C 20 -aryl and optionally substituted C 2 -C 20 -heteroaryl.
16. The interlayer of claim 14 , wherein the crosslinkable group of the adhesion promoter is selected from a maleimide, a 3-monoalkyl-maleimide, a 3,4-dialkylmaleimide, an epoxy, a vinyl, an acetyl, an indenyl a, cinnamate or a coumarin group, or the crosslinkable group comprises a substituted or unsubstituted maleimide portion, an epoxide portion, a vinyl portion, a cinnamate portion or a coumarin portion.
17. The interlayer of claim 13 , wherein the adhesion promoter is a compound having the following structure
where SiR 12 R 13 R 14 is as defined in claim 15 , A′ is as defined in claim 16 , and R 10 and R 11 are each independently H or a C 1 -C 6 alkyl group.
18. The interlayer of claim 1 , wherein the polymer or polymer composition contains one or more repeating units having a crosslinkable group, and the interlayer further comprises a crosslinker which is a compound comprising two or more crosslinkable functional groups that are capable of reacting with the crosslinkable group of the said repeating unit of the polymer or polymer composition.
19. The interlayer of claim 18 , wherein the crosslinker is a compound of formula IV1 or IV2
P—X—P IV1
H 4-m C(A″p-P) m IV2
where X is A″-X′-A″, X′ is, O, S, NH, or a single bond, A″ is a single covalent bond or a connecting, spacer or bridging group, P is a crosslinkable group, and m is 2, 3 or 4.
20. The interlayer of claim 19 , wherein the crosslinkable group of the crosslinker is selected from a maleimide, a 3-monoalkyl-maleimide, a 3,4-dialkylmaleimide, an epoxy, a vinyl, an acetyl, an indenyl, a cinnamate or a coumarin group, or the crosslinkable group comprises a substituted or unsubstituted maleimide portion, an epoxide portion, a vinyl portion, a cinnamate portion or a coumarin portion.
21. The interlayer of claim 19 , wherein the crosslinker is a compound of the following formula
where R 10 and R 11 are independently of each other H or a C 1 -C 6 alkyl group, and A″ is a single bond or a connecting, spacer or bridging group as defined in claim 19 and additionally selected from (CZ 2 ) n , (CH 2 ) n —(CH═CH) p —(CH 2 ) n , (CH 2 ) n —O, (CH 2 ) n —O—(CH 2 ) n , (CH 2 ) n —C 6 Q 10 -(CH 2 ) n , and C(O)—O, where
each n is independently an integer from 0 to 12,
p is an integer from 1-6,
Z is independently H or F, C 6 Q 10 is cyclohexyl that is substituted with Q, and
Q is independently H, F, CH 3 , CF 3 or OCH 3 .
22. An electronic device which comprises the interlayer of claim 1 which is in contact with a dielectric layer, wherein the dielectric layer is part of a gate dielectric layer.
23. An electronic device which comprises the interlayer of claim 1 which is in contact with a dielectric layer, wherein the dielectric layer is a passivation layer.
24. The interlayer of claim 1 that is in contact with a dielectric layer in an organic electronic device, wherein the organic electronic device further comprises an organic semiconductor material, and the polymer composition further comprises a solvent having orthogonal solubility properties with respect to the organic semiconductor material.
25. The interlayer of claim 1 , wherein the polycycloolefinic polymer comprises one or more repeat units derived from a monomer selected from NBCH 2 C 6 F 5 , NBC 6 F 5 , NBCH 2 C 6 F 2 , NBCH 2 C 6 H 4 CF 3 MeOAcNB and NBalkylC 6 F 5 , wherein Me is methyl and OAc is acetate, and repeating units derived from a norbornene-type monomer selected from the group consisting of
26. The interlayer of claim 1 , wherein the polycycloolefinic polymer comprises two or more repeat units derived from a monomer selected from NBCH 2 C 6 F 5 , NBC 6 F 5 , NBCH 2 C 6 F 2 , NBCH 2 C 6 H 4 CF 3 MeOAcNB and NBalkylC 6 F 5 , wherein Me is methyl and OAc is acetate, and repeating units derived from a norbornene-type monomer selected from the group consisting of
27. The interlayer of claim 1 , wherein the polycycloolefinic polymer comprises one or more repeat units derived from a monomer selected from NBCH 2 C 6 F 5 , NBC 6 F 5 , NBCH 2 C 6 F 2 and MeOAcNB, wherein Me is methyl and OAc is acetate, and repeating units derived from a norbornene-type monomer selected from the group consisting of
28. The interlayer of claim 1 , wherein the polycycloolefinic polymer comprises two or more repeat units derived from a monomer selected from NBCH 2 C 6 F 5 , NBC 6 F 5 and MeOAcNB, wherein Me is methyl and OAc is acetate, and repeating units derived from a norbornene-type monomer selected from the group consisting of
29. An interlayer that is in direct contact with a dielectric layer in an organic electronic device, said interlayer consisting essentially of a norbornene-type polymer formed by one or more norbornene-type monomers selected from subformulae 1-54:
NB
1
MeNB
2
BuNB
3
HexNB
4
OctNB
5
DecNB
6
PENB
7
TD
8
MeOAcNB
9
NBXOH
10
NBCH2GlyOAc
11
NBCH2GlyOH
12
NBTON
13
NBTODD
14
NBC4F9
15
NBCH2C6F5
16
NBC6F5
17
NBCH2C6F2
18
NBCH2C6H4CF3
19
NBalkylC6F5
20
FPCNB
21
FHCNB
22
FOCHNB
23
FPCHNB
24
C8PFAcNB
25
PPVENB
26
DCPD
27
EONB
28
MGENB
29
AkSiNB
30
ArSiNB
31
MCHMNB
32
NPCHMNB
33
DMMIMeNB
34
DMMIEtNB
35
DMMIPrNB
36
DMMIBuNB
37
DMMIHxNB
38
EtPhDMMINB
39
MMIMeNB
40
MINB
41
MIENB
42
DHNMINB
43
MeOCinnNB
44
CinnNB
45
EtMeOCinnNB
46
MeCoumNB
47
EtCoumNB
48
EtPhIndNB
49
PhIndNB
50
DiOxoTCNB
51
PFBTCNB
52
TESNB
53
PMNB
54
where “Me” means methyl, “Et” means ethyl, “OMe-p” means para-methoxy, “Ph” and “C 6 H 5 ” mean phenyl, “C 6 H 4 ” means phenylene, “C 6 F 5 ” means pentafluorophenyl, “OAc” means acetate, “PFAc” means —OC(O)—C 7 F 15 , and for each of the above subformulae having a methylene bridging group, such methylene bridging group is inclusive of a covalent bond or —(CH 2 ) p — where p is an integer from 1 to 6 wherein the dielectric layer comprises a fluoropolymer.
30. An organic electronic device comprising an interlayer that is in direct contact with a dielectric layer, said interlayer consisting essentially of a polycycloolefinic polymer or a polymer composition consisting essentially of a polycycloolefinic polymer, said polymer having a first type of repeating unit in accordance with formula I:
wherein Z is selected from —CH 2 —, —CH 2 —CH 2 — or —O—, m is an integer from 0 to 5, each of R 1 , R 2 , R 3 and R 4 are independently selected from H, a C 1 to C 25 hydrocarbyl, a C 1 to C 25 halohydrocarbyl or a C 1 to C 25 perhalocarbyl group and wherein the dielectric layer comprises a fluoropolymer.
31. The electronic device of claim 30 , which is a field effect transistor (FET), thin film transistor (TFT), integrated circuit (IC) or Radio Frequency Identification (RFID) tag.
32. The electronic device of claim 30 , which is a top gate or bottom gate field effect transistor (FET).