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US 11,778,907 B2Granted
Composition for organic electronic devices
AssigneeMerck Patent GmbH
InventorsAmir Parham, Jonas Kroeber, Christian Eickhoff, Tobias Grossmann, Aurélie Ludemann, Dominik Joosten
Life of this patent
Estimating the term…
Abstract
The present invention relates to a composition comprising a bipolar host and an electron-transporting host, especially for use as matrix material in electronic devices, especially organic electroluminescent devices, and especially in an organic light-emitting diode (OLED). The invention further relates to electronic devices comprising said composition.
Claims32
A composition comprising a bipolar host and an electron-transporting host and wherein the electron-transporting host is a compound of the general formula (2) or (2a)
- where the symbols and indices used are as follows:
- E is a single bond or NAr4;
- X is C when Ar1 is a 6-membered aryl or 6-membered heteroaryl group, or is C or N when Ar1 is a 5-membered heteroaryl group;
- Ar1 together with the X group and the carbon atom shown explicitly is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R radicals;
- Ar2 together with the carbon atoms shown explicitly is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R radicals;
- at the same time, Ar2 may also be joined to Ar3 by a single bond;
- Ar3 is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(Ar5)2, N(R6)2, C(═O)Ar5, C(═O)R6, P(═O)(Ar5)2, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R6 radicals, where one or more nonadjacent CH2 groups may be replaced by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6) SO, SO2, NR6, O, S or CONR6 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted in each case by one or more R6 radicals, an aryloxy or heteroaryloxy group which has 5 to 30 aromatic ring atoms and may be substituted by one or more R6 radicals, or a combination of these systems;
- at the same time, Ar3 may also be joined to Ar2 by a single bond;
- Ar4 is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R radicals;
- at the same time, Ar4 may also be joined to Ar2 or A′ by a single bond;
- m is 1, 3 or 4;
- J when m=2 is a single bond or a bivalent group, or when m=3 is a trivalent group, or when m=4 is a tetravalent group, each of which is bonded at any desired position to Ar1, Ar2, Ar3 or Ar4;
- R is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(Ar5)2, N(R6)2, C(═O)Ar5, C(═O)R6, P(═O)(Ar5)2, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R6 radicals, where one or more nonadjacent CH2 groups may be replaced by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, SN(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R6 radicals, an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R6 radicals, or a combination of these systems;
- where it is optionally possible for two or more adjacent R substituents to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R6 radicals;
- R6 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO2, N(Ar5)2, N(R7)2, C(═O)Ar5, C(═O)IC, P(═O)(Ar5)2 a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R7 radicals, where one or more nonadjacent CH2 groups may be replaced by R7C═CR7, C≡C, Si(R7)2, Ge(R7)2, Sn(R7)2, C═O, C═S, C═Se, C═NR7, P(═O)(R7), SO, SO2, NR7, O, S or CONR7 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R7 radicals, an arvloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R7 radicals, or a combination of these systems;
- where it is optionally possible for two or more adjacent R6 substituents to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R7 radicals:
- Ar5 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more nonaromatic R7 radicals;
- at the same time, two Ar5 radicals bonded to the same nitrogen atom or phosphorus atom may also be bridged to one another by a single bond or a bridge selected from N(R), C(R7)2 and O;
- R7 is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN, where two or more adjacent R7 substituents together may forma mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system.
16 more elements
A composition comprising a bipolar host and an electron-transporting host and wherein the bipolar host is selected from:
- the compounds of the formulae (1a-13) to (1a-18) having the general formula
- where:
- ET group
- Bipolar host
- (ET-12)
- Formula (1a-13)
- (ET-13)
- Formula (1a-14)
- (ET-14)
- Formula (1a-15)
- (ET-15)
- Formula (1a-16)
- (ET-16)
- Formula (1a-17)
- (ET-20)
- Formula (1a-18);
- the compounds of the formulae (1a-19) to (1a-24) having the general formula where:
- ET group
- Bipolar host
- (ET-12)
- Formula (1a-19)
- (ET-13)
- Formula (1a-20)
- (ET-14)
- Formula (1a-21)
- (ET-15)
- Formula (1a-22)
- (ET-16)
- Formula (1a-23)
- (ET-20)
- Formula (1a-24);
- the compounds of the formulae (1b-13) to (1b-18) having the general formula
- where:
- ET group
- Bipolar host
- (ET-12)
- Formula (1b-13)
- (ET-13)
- Formula (1b-14)
- (ET-14)
- Formula (1b-15)
- (ET-15)
- Formula (1b-16)
- (ET-16)
- Formula (1b-17)
- (ET-20)
- Formula (1b-18);
- and
- the compounds of the formulae (1b-19) to (1b-24) having the general formula
- where:
- ET group
- Bipolar host
- (ET-12)
- Formula (1b-19)
- (ET-13)
- Formula (1b-20)
- (ET-14)
- Formula (1b-21)
- (ET-15)
- Formula (1b-22)
- (ET-16)
- Formula (1b-23)
- (ET-20)
- Formula (1b-24);
- where Y, Rh and R2 have the definitions given above
- bonded via a bridging (L)n group or directly to an HT group (when n=0) selected from the structures of the formulae (HT-6), (HT-7), (HT-8) and (HT-9)
- where L, n, le and R5 have the definitions given above and the dotted bond marks the position of attachment to (L)n or the HT group (when n=0),
- R1, R1′ is the same or different at each instance and is H, D, F, Cl, Br, I, N(R2)2, CN, NO2, Si(R2)3, B(OR2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, S(═O)2R2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R2 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or a combination of two or more of these groups;
- at the same time, two or more adjacent R1, R1′ or R1″ radicals together may form a mono- or polycyclic, aliphatic or aromatic ring system;
- R2 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R3)2, CN, NO2, Si(R3)3, B(OR3)2, C(═O)R3, P(═O)(R3)2, S(═O)R3, S(═O)2R3, OSO2R3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R3 radicals, where one or more nonadjacent CH2 groups may be replaced by R3C═CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, P(═O)(R3), SO, SO2, NR3, O, S or CONR3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R3 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R3 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R3 radicals, or a combination of two or more of these groups;
- at the same time, two or more adjacent R2 radicals together may form a mono- or polycyclic, aliphatic or aromatic ring system,
- R3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F;
- at the same time, two or more R3 substituents together may also form a mono- or polycyclic aliphatic or aromatic ring system,
- R4 is the same or different at each instance and is N(R2)2, Si(R2)3, B(OR2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, S(═O)2R2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R2 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or a combination of two or more of these groups;
- at the same time, two or more adjacent R4 radicals together may form a mono- or polycyclic, aliphatic or aromatic ring system and
- R5 is the same or different at each instance and is either R1′ or R4.
73 more elements
A composition comprising a bipolar host and an electron-transporting host and wherein the bipolar host is selected from the compounds of the formulae (1a-37), (1a-38), (1b-37) and (1b-38)
- where
- R1, R1′ is the same or different at each instance and is H, D, F, Cl, Br, I, N(R2)2, CN, NO2, Si(R2)3, B(OR2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, S(═O)2R2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups may be replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R2 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R2 radicals, or a combination of two or more of these groups;
- at the same time, two or more adjacent R1, R1′ or R1″ radicals together may form a mono- or polycyclic, aliphatic or aromatic ring system:
- R2 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R3)2, CN, NO2, Si(R3)3, B(OR3)2, C(═O)R3, P(═O)(R3)2, S(═O)R3, S(═O)2R3, OSO2R3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R3 radicals, where one or more nonadjacent CH2 groups may be replaced by R3C═CR3, C≡C, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, P(═O)(R3), SO, SO2, NR3, O, S or CONR3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R3 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R3 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R3 radicals, or a combination of two or more of these groups;
- at the same time, two or more adjacent R2 radicals together may form a mono- or polycyclic, aliphatic or aromatic ring system;
- R3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F;
- at the same time, two or more R3 substituents together may also form a mono- or polycyclic aliphatic or aromatic ring system.
4 more elements
Dependencies are inferred from the claim text.