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US 9,793,485 B2Granted
Benzocyclobutenes derived compositions, and electronic devices containing the same
AssigneesDow Global Technologies LLC, Rohm and Haas Electronic Materials LLC
InventorsMinrong Zhu, Jichang Feng, Shaoguang Feng, Chun Liu, Nolan T. McDougal, David D. Devore, Peter Trefonas, III, Liam P. Spencer
Life of this patent
Estimating the term…
Abstract
The invention provides compositions comprising crosslinkable BCB-functionalized materials for use in OLEDs applications. The inventive compositions can be used to form hole-transporting materials for use in electroluminescent devices. In particular, the invention provides a composition comprising at least one compound selected from Structure A, as described herein.
Claims15
A composition comprising at least one compound selected from Structure A:
- wherein groups R4 to R19 are each, independently, selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, a halogen, a cyano, a nitro, an alkoxy, or a hydroxyl;
- Ar1 is selected from a substituted aryl, an unsubstituted aryl, a substituted heteroaryl, or an unsubstituted heteroaryl;
- (R1)a is selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, a halogen, a cyano, a nitro, an alkoxy, or a hydroxyl;
- Ar2 is selected from a substituted aryl, an unsubstituted aryl, a substituted heteroaryl, or an unsubstituted heteroaryl;
- (R2)b is selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, a halogen, a cyano, a nitro, an alkoxy, or a hydroxyl;
- Ar3 is selected from a substituted aryl, an unsubstituted aryl, a substituted heteroaryl, or an unsubstituted heteroaryl;
- (R3)c is selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, a halogen, a cyano, a nitro, an alkoxy, or a hydroxyl;
- and
- with the proviso that at least one of groups (R1)a, (R2)b, (R3)c or R4 to R19 is independently selected from the benzocyclobutene structures of Structure B, Structure C, Structure D, or Structure E, as follows:
- wherein Structure B is connected to Structure A though -L-;
- wherein, for Structure B:
- 1b) one of Ra1, Ra2, Ra3 or Ra4 is -L-;
- and wherein -L- is selected from the following:
- —O—;
- -alkylene-;
- —O-alkylene-;
- —O-arylene-;
- —O-alkylene-arylene-;
- —O-alkylene-O—;
- —O-alkylene-O-alkylene-O—;
- —O-arylene-O—;
- —O-alkylene-arylene-O—;
- —O—(CH2CH2-O)n-, wherein n is from 2 to 20;
- —O-alkylene-O-alkylene-;
- —O-alkylene-O-arylene-;
- —O-arylene-O—;
- —O-arylene-O-alkyene-;
- —O-arylene-O-arylene-;
- or a covalent bond linking ‘Structure B” to “Structure A”;
- and
- 2b) the remaining Ra1, Ra2, Ra3 and Ra4 are each, independently, selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, a halogen, a cyano, a nitro, an alkoxy, or a hydroxyl;
- and
- 3b) Ra5, Ra6, Ra7 or Ra8 are each, independently, selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, a halogen, a cyano, a nitro, an alkoxy, or a hydroxyl;
- wherein Structure C is connected to Structure A though -L-;
- wherein, for Structure C:
- 1c) one of Ra5, Ra6, Ra7 or Ra8 is -L-;
- and wherein -L- is selected from the following:
- —O—;
- -alkylene-;
- -arylene-;
- —O-alkylene-;
- —O-arylene-;
- —O-alkylene-arylene-;
- —O-alkylene-O—;
- —O-alkylene-O-alkylene-O—;
- —O-arylene-O—;
- —O-alkylene-arylene-O—;
- —O—(CH2CH2-O)n-, wherein n is from 2 to 20;
- —O-alkylene-O-alkylene-;
- —O-alkylene-O-arylene-;
- —O-arylene-O-alkyene-;
- —O-arylene-O-arylene-;
- or a covalent bond linking ‘Structure C” to “Structure A”;
- 2c) the remaining Ra5, Ra6, Ra7 or Ra8 are each, independently, selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, a halogen, a cyano, a nitro, or a hydroxyl;
- 3c) Ra1, Ra2, Ra3 and Ra4 are each, independently, selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, a halogen, a cyano, a nitro, an alkoxy, or a hydroxyl;
- wherein Structure D is connected to Structure A though -L-;
- wherein, for Structure D:
- 1di) for one -L1-, one of Ra1, Ra2, Ra3 or Ra4 of the benzocyclobutene moiety directly bonded to this -L1-, is independently -L1-;
- and wherein -L1- is selected from the following:
- —O—;
- -alkylene-;
- —O-alkylene-;
- —O-arylene-;
- —O-alkylene-arylene-;
- —O-alkylene-O—;
- —O-alkylene-O-alkylene-O—;
- —O-arylene-O—;
- —O-alkylene-arylene-O—;
- —O—(CH2CH2-O)n-, wherein n is from 2 to 20;
- —O-alkylene-O-alkylene-;
- —O-alkylene-O-arylene-;
- —O-arylene-O—;
- —O-arylene-O-alkyene-;
- —O-arylene-O-arylene-;
- —O-alkylene-arylene-O—;
- or a covalent bond linking the 4 carbon ring to Ar;
- 1dii) for the other -L1-, one of Ra1, Ra2, Ra3 or Ra4 of the other benzocyclo-butene moiety directly bonded to this -L1-, is independently -L1-;
- and wherein -L1- is selected from the following:
- —O—;
- -alkylene-;
- —O-alkylene-;
- —O-arylene-;
- —O-alkylene-arylene-;
- —O-alkylene-O—;
- —O-alkylene-O-alkylene-O—;
- —O-arylene-O—;
- —O— alkylene-arylene-O—;
- —O—(CH2CH2-O)n-, wherein n is from 2 to 20;
- —O-alkylene-O-alkylene-;
- —O-alkylene-O-arylene-;
- —O-arylene-O—;
- —O-arylene-O-alkyene-;
- —O-arylene-O-arylene-;
- —O-alkylene-arylene-O—;
- or a covalent bond linking the 4 carbon ring to Ar;
- 2d) Ar is a substituted or unsubstituted C5-C60 aryl group;
- 3d) -L- is selected from the following:
- —O—;
- -alkylene-;
- -arylene-;
- —O-alkylene-;
- —O-arylene-;
- —O-alkylene-arylene-;
- —O-alkylene-O—;
- —O-alkylene-O-alkylene-O—;
- —O-arylene-O—;
- —O-alkylene-arylene-O—;
- —O—(CH2CH2-O)n-, wherein n is from 2 to 20;
- —O-alkylene-O-alkylene-;
- —O-alkylene-O-arylene-;
- —O-arylene-O—;
- —O-arylene-O-alkyene-;
- —O-arylene-O-arylene-;
- or a covalent bond linking “Structure D” to “Structure A”;
- 4di) the remaining Ra1, Ra2, Ra3 and Ra4 of one benzocyclobutene moiety are each, independently, selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, a halogen, a cyano, a nitro, or a hydroxyl;
- 4dii) the remaining Ra1, Ra2, Ra3 and Ra4 of the other benzocyclobutene moiety are each, independently, selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, a halogen, a cyano, a nitro, or a hydroxyl;
- 5di) Ra5, Ra6, Ra7 or Ra8 of one benzocyclobutene moiety are each, independently, selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, a halogen, a cyano, a nitro, or a hydroxyl;
- 5dii) Ra5, Ra6, Ra7 or Ra8 of the other benzocyclobutene moiety are each, independently, selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, a halogen, a cyano, a nitro, or a hydroxyl;
- wherein
- Structure E is connected to Structure A though -L-;
- wherein, for Structure E:
- 1ei) for one -L1-, one of Ra5, Ra6, Ra7 or Ra8 of the benzocyclobutene moiety directly bonded to this -L1-, is independently -L1-;
- and wherein -L1- is selected from the following:
- —O—;
- -alkylene-;
- -arylene-;
- —O-alkylene-;
- —O-arylene-;
- —O-alkylene-arylene-;
- —O-alkylene-O—;
- —O-alkylene-O-alkylene-O—;
- —O-arylene-O—;
- —O-alkylene-arylene-O—;
- —O—(CH2CH2-O)n-, wherein n is from 2 to 20;
- —O-alkylene-O-alkylene-;
- —O-alkylene-O-arylene-;
- —O-arylene-O—;
- —O-arylene-O-alkyene-;
- —O-arylene-O-arylene-;
- or a covalent bond linking the 6-carbon ring to Ar;
- 1eii) for the other -L1-, one of Ra5, Ra6, Ra7 or Ra8 of the other benzocyclo-butene moiety directly bonded to this -L1-, is independently -L1-;
- and wherein -L1- is selected from the following:
- —O—;
- -alkylene-;
- -arylene-;
- —O-alkylene-;
- —O-arylene-;
- —O-alkylene-arylene-;
- —O-alkylene-O—;
- —O-alkylene-O-alkylene-O—;
- —O-arylene-O—;
- —O— alkylene-arylene-O—;
- —O—(CH2CH2-O)n-, wherein n is from 2 to 20;
- —O-alkylene-O-alkylene-;
- —O-alkylene-O-arylene-;
- —O-arylene-O—;
- —O-arylene-O-alkyene-;
- —O-arylene-O-arylene-;
- or a covalent bond linking the 6-carbon ring to Ar;
- 2e) Ar is a substituted or unsubstituted C5-C60 aryl group;
- and
- 3e) -L- is selected from the following:
- —O—;
- -alkylene-;
- -arylene-;
- —O-alkylene-;
- —O-arylene-;
- —O-alkylene-arylene-;
- —O-alkylene-O—;
- —O-alkylene-O-alkylene-O—;
- —O-arylene-O—;
- —O-alkylene-arylene-O—;
- —O—(CH2CH2-O)n-, wherein n is from 2 to 20;
- —O-alkylene-O-alkylene-;
- —O-alkylene-O-arylene-;
- —O-arylene-O—;
- —O-arylene-O-alkyene-;
- —O-arylene-O-arylene-;
- or a covalent bond linking “Structure E” to “Structure A”;
- 4ei) the remaining Ra5, Ra6, Ra7 or Ra8 of one benzocyclobutene moiety are each, independently, selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, a halogen, a cyano, a nitro, or a hydroxyl;
- 4eii) the remaining Ra5, Ra6, Ra7 or Ra8 of the other benzocyclobutene moiety are each, independently, selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, a halogen, a cyano, a nitro, or a hydroxyl;
- 5ei) Ra1, Ra2, Ra3 and Ra4 of one benzocyclobutene moiety are each, independently, selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, a halogen, a cyano, a nitro, an alkoxy, or a hydroxyl;
- 5eii) Ra1, Ra2, Ra3 and Ra4 of the other benzocyclobutene moiety are each, independently, selected from hydrogen, a hydrocarbon, a substituted hydrocarbon, a halogen, a cyano, a nitro, an alkoxy, or a hydroxyl;
- and
- wherein for Structure A, two or more R groups may optionally form one or more ring structures;
- and
- wherein for Structure A, one or more hydrogen atoms may be optionally substituted with deuterium.
184 more elements
Dependencies are inferred from the claim text.