Composition for organic electronic devices

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.

Claims

1. 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) ##STR00156## where the symbols and indices used are as follows: E is a single bond or NAr.sup.4; X is C when Ar.sup.1 is a 6-membered aryl or 6-membered heteroaryl group, or is C or N when Ar.sup.1 is a 5-membered heteroaryl group; Ar.sup.1 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; Ar.sup.2 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, Ar.sup.2 may also be joined to Ar.sup.3 by a single bond; Ar.sup.3 is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.5).sub.2, N(R.sup.6).sub.2, C(═O)Ar.sup.5, C(═O)R.sup.6, P(═O)(Ar.sup.5).sub.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 R.sup.6 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.6C═CR.sup.6, C≡C, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, C═O, C═S, C═Se, C═NR.sup.6, P(═O)(R.sup.6) SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.6 radicals, an aryloxy or heteroaryloxy group which has 5 to 30 aromatic ring atoms and may be substituted by one or more R.sup.6 radicals, or a combination of these systems; at the same time, Ar.sup.3 may also be joined to Ar.sup.2 by a single bond; Ar.sup.4 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, Ar.sup.4 may also be joined to Ar.sup.2 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 Ar.sup.1, Ar.sup.2, Ar.sup.3 or Ar.sup.4; R is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.5).sub.2, N(R.sup.6).sub.2, C(═O)Ar.sup.5, C(═O)R.sup.6, P(═O)(Ar.sup.5).sub.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 R.sup.6 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.6C═CR.sup.6, C≡C, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, SN(R.sup.6).sub.2, C═O, C═S, C═Se, C═NR.sup.6, P(═O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.6 radicals, an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.6 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 R.sup.6 radicals; R.sup.6 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.5).sub.2, N(R.sup.7).sub.2, C(═O)Ar.sup.5, C(═O)IC, P(═O)(Ar.sup.5).sub.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 R.sup.7 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.7C═CR.sup.7, C≡C, Si(R.sup.7).sub.2, Ge(R.sup.7).sub.2, Sn(R.sup.7).sub.2, C═O, C═S, C═Se, C═NR.sup.7, P(═O)(R.sup.7), SO, SO.sub.2, NR.sup.7, O, S or CONR.sup.7 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.7 radicals, an arvloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.7 radicals, or a combination of these systems; where it is optionally possible for two or more adjacent R.sup.6 substituents to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R.sup.7 radicals: Ar.sup.5 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 R.sup.7 radicals; at the same time, two Ar.sup.5 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(R.sup.7).sub.2 and O; R.sup.7 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 R.sup.7 substituents together may forma mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system.

2. The composition according to claim 1, wherein the bipolar host is selected from the group of the triazines, pyrimidines, pyrazines, pyridines, pyrazoles, pyridazines, quinolines, isoquinolines, quinoxalines, quinazolines, thiazoles, benzothiazoles, oxazoles, oxadiazoles, benzoxazoles, imidazoles, benzimidazoles, carbazoles, indenocarbazoles, indolocarbazoles, phosphine oxides, phenyl sulfonyl s, ketones, lactams, phenanthrolines and triarylamines.

3. The composition according to claim 1, wherein the bipolar host is a compound of the general formula (1)
ET-(L).sub.n-HT(R.sup.4).sub.q   Formula (1) where the symbols and indices used are as follows: ET is an organic electron-transporting group (ET) from the group of the electron-deficient heteroaromatic groups, where the ET group may be substituted by one or more independent R.sup.1 radicals; HT is an organic hole-transporting group (HT) from the group of the electron-rich heteroaromatic groups, where the HT group may be substituted by one or more independent R.sup.1′ radicals; L is C(═O), S(═O).sub.2, P(═O)(R.sup.1″) or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more independent R.sup.1″ radicals; n is 0, 1, 2, 3 or 4; q is an integer from 1 to 5; R.sup.1, R.sup.1′, R.sup.1″ is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.2).sub.2, CN, NO.sub.2, Si(R.sup.2).sub.3, B(OR.sup.2).sub.2, C(═O)R.sup.2, P(═O)(R.sup.2).sub.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, OSO.sub.2R.sup.2, 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 R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.2C═CR.sup.2, C≡C, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, P(═O)(R.sup.2), SO, SO.sub.2, NR.sup.2, O, S or CONR.sup.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.2 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 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 R.sup.2 radicals, or a combination of two or more of these groups; at the same time, two or more adjacent R.sup.1, R.sup.1′ or R.sup.1″ radicals together may form a mono- or polycyclic, aliphatic or aromatic ring system; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.3).sub.2, CN, NO.sub.2, Si(R.sup.3).sub.3, B(OR.sup.3).sub.2, C(═O)R.sup.3, P(═O)(R.sup.3).sub.2, S(═O)R.sup.3, S(═O).sub.2R.sup.3, OSO.sub.2R.sup.3, 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 R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.3C═CR.sup.3, C≡C, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═Se, C═NR.sup.3, P(═O)(R.sup.3), SO, SO.sub.2, NR.sup.3, O, S or CONR.sup.3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.3 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 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 R.sup.3 radicals, or a combination of two or more of these groups; at the same time, two or more adjacent R.sup.2 radicals together may form a mono- or polycyclic, aliphatic or aromatic ring system; R.sup.3 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 R.sup.3 substituents together may also form a mono- or polycyclic aliphatic or aromatic ring system; R.sup.4 is the same or different at each instance and is N(R.sup.2).sub.2, Si(R.sup.2).sub.3, B(OR.sup.2).sub.2, C(═O)R.sup.2, P(═O)(R.sup.2).sub.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, OSO.sub.2R.sup.2, 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 R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.2C═CR.sup.2, C≡C, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, P(═O)(R.sup.2), SO, SO.sub.2, NR.sup.2, O, S or CONR.sup.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.2 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 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 R.sup.2 radicals, or a combination of two or more of these groups; at the same time, two or more adjacent R.sup.4 radicals together may form a mono- or polycyclic, aliphatic or aromatic ring system.

4. The composition according to claim 3, wherein ET is selected from the group of the triazines, pyrimidines, pyrazines, pyrazoles, pyridines, pyridazines, quinolines, isoquinolines, quinoxalines, quinazolines, thiazoles, benzothiazoles, oxazoles, oxadiazoles, benzoxazoles, imidazoles and benzimidazoles, where the ET group may be substituted by one or more independent R.sup.1 radicals; HT is selected from the group of the carbazoles, indenocarbazoles, indolocarbazoles, phenanthrolines and triarylamines, where the HT group may be substituted by one or more independent R.sup.1′ radicals; n is 1; q is 1; R.sup.1, R.sup.1′, R.sup.1″ is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.2).sub.2, CN, NO.sub.2, Si(R.sup.2).sub.3, B(OR.sup.2).sub.2, C(═O)R.sup.2, P(═O)(R.sup.2).sub.2, S(═O)R.sup.2, S(═O)R.sup.2, OSO.sub.2R.sup.2 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 R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.2C═CR.sup.2, C≡C, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, P(═O)(R.sup.2), SO, SO.sub.2, NR.sup.2, O, S or CONR.sup.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.2 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 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 R.sup.2 radicals, or a combination of two or more of these groups; at the same time, two or more adjacent R.sup.1, R.sup.1′ or R.sup.1″ radicals together do not form a mono- or polycyclic, aliphatic or aromatic ring system.

5. The composition according to claim 3, wherein the ET group is selected from the following groups: ##STR00157## where the dotted bond marks the position of attachment to the bridging (L).sub.n group or the HT group (when n=0), R.sup.1 is as defined in claim 3 and Q′ is the same or different at each instance and is CR.sup.1 or N, and Q″ is NR.sup.1, O or S; and where at least one Q′ and N and/or at least one Q″ is NR.sup.1.

6. The composition according to claim 3, wherein the HT group has a structure of the formula (HT-1) ##STR00158## where: A, B are the same or different and are an aromatic or heteroaromatic ring which has 5 or 6 ring atoms and may be substituted by one or more R.sup.5 radicals; o, p are the same or different and are 0 or 1; U is the same or different at each instance and is CR.sup.5, N or O, where not more than two U per cycle, which are not adjacent to one another, are N or O, and where U is carbon if a bridging (L), group or an ET group (when n=0) is attached to this position; R.sup.5 is the same or different at each instance and is R.sup.1′ or R.sup.4, with the proviso that there are 1 to 5 R.sup.5 radicals corresponding to R.sup.4 in the structure of the formula (HT-1), where R.sup.1′ and R.sup.4 have the definitions given in claim 3.

7. The composition according to claim 3, wherein the HT group is selected from the following groups: ##STR00159## where R.sup.5 is the same or different at each instance and is either Rh or R.sup.4, with the proviso that the (HT-2), (HT-3), (HT-4) and (HT-5) groups each have, rather than one of the R.sup.5 radicals, a bond to the bridging (L).sub.n group or the ET group (when n=0), and that, in each of the (HT-2), (HT-3), (HT-4) and (HT-5) groups, there are 1 to 5 R.sup.5 radicals corresponding to R.sup.4, and where R.sup.1′ and R.sup.4 have the definitions given in claim 3.

8. The composition according to claim 1, wherein the bipolar host contains at least one of the (ET-12) to (ET-16) and (ET-20) groups ##STR00160## 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) ##STR00161## where L, n, R.sup.1 and R.sup.5 have the definitions given above and the dotted bond marks the position of attachment to (L).sub.n or the HT group (when n=0).

9. The composition according to claim 1, wherein the bipolar host is selected from the compounds of the formulae (1a-1) to (1a-6) and (1b-1) to (1b-6) ##STR00162## ##STR00163## where L, n, R.sup.1, and R.sup.5 have the definitions given above.

10. The composition according to claim 3, wherein the bipolar host is selected from the compounds of the formulae (1a-7) to (1a-12) and formulae (1b-7) to (1b-12) ##STR00164## ##STR00165## ##STR00166## where Y is O or S, and R.sup.1 and R.sup.5 have the definitions given above, and where, in the formulae (1a-7) to (1a-12) and (1b-7) to (1b-12), exactly one of the R.sup.5 radicals in each case corresponds to an R.sup.4 radical.

11. 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 ##STR00167## where: TABLE-US-00015 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: ##STR00168## TABLE-US-00016 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 ##STR00169## where: TABLE-US-00017 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 ##STR00170## where: TABLE-US-00018 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 R.sup.2 have the definitions given above ##STR00171## bonded via a bridging (L).sub.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) ##STR00172## where L, n, le and R.sup.5 have the definitions given above and the dotted bond marks the position of attachment to (L).sub.n or the HT group (when n=0), R.sup.1, R.sup.1′ is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.2).sub.2, CN, NO.sub.2, Si(R.sup.2).sub.3, B(OR.sup.2).sub.2, C(═O)R.sup.2, P(═O)(R.sup.2).sub.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, OSO.sub.2R.sup.2, 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 R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.2C═CR.sup.2, C≡C, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, P(═O)(R.sup.2), SO, SO.sub.2, NR.sup.2, O, S or CONR.sup.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.2 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 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 R.sup.2 radicals, or a combination of two or more of these groups; at the same time, two or more adjacent R.sup.1, R.sup.1′ or R.sup.1″ radicals together may form a mono- or polycyclic, aliphatic or aromatic ring system; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.3).sub.2, CN, NO.sub.2, Si(R.sup.3).sub.3, B(OR.sup.3).sub.2, C(═O)R.sup.3, P(═O)(R.sup.3).sub.2, S(═O)R.sup.3, S(═O).sub.2R.sup.3, OSO.sub.2R.sup.3, 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 R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.3C═CR.sup.3, C≡C, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═Se, C═NR.sup.3, P(═O)(R.sup.3), SO, SO.sub.2, NR.sup.3, O, S or CONR.sup.3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.3 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 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 R.sup.3 radicals, or a combination of two or more of these groups; at the same time, two or more adjacent R.sup.2 radicals together may form a mono- or polycyclic, aliphatic or aromatic ring system, R.sup.3 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 R.sup.3 substituents together may also form a mono- or polycyclic aliphatic or aromatic ring system, R.sup.4 is the same or different at each instance and is N(R.sup.2).sub.2, Si(R.sup.2).sub.3, B(OR.sup.2).sub.2, C(═O)R.sup.2, P(═O)(R.sup.2).sub.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, OSO.sub.2R.sup.2, 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 R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced R.sup.2C═CR.sup.2, C≡C, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, P(═O)(R.sup.2), SO, SO.sub.2, NR.sup.2, O, S or CONR.sup.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.2 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 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 R.sup.2 radicals, or a combination of two or more of these groups; at the same time, two or more adjacent R.sup.4 radicals together may form a mono- or polycyclic, aliphatic or aromatic ring system and R.sup.5 is the same or different at each instance and is either R.sup.1′ or R.sup.4.

12. 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) ##STR00173## where R.sup.1, R.sup.1′ is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.2).sub.2, CN, NO.sub.2, Si(R.sup.2).sub.3, B(OR.sup.2).sub.2, C(═O)R.sup.2, P(═O)(R.sup.2).sub.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, OSO.sub.2R.sup.2, 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 R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.2C═CR.sup.2, C≡C, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, P(═O)(R.sup.2), SO, SO.sub.2, NR.sup.2, O, S or CONR.sup.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.2 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 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 R.sup.2 radicals, or a combination of two or more of these groups; at the same time, two or more adjacent R.sup.1, R.sup.1′ or R.sup.1″ radicals together may form a mono- or polycyclic, aliphatic or aromatic ring system: R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.3).sub.2, CN, NO.sub.2, Si(R.sup.3).sub.3, B(OR.sup.3).sub.2, C(═O)R.sup.3, P(═O)(R.sup.3).sub.2, S(═O)R.sup.3, S(═O).sub.2R.sup.3, OSO.sub.2R.sup.3, 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 R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.3C═CR.sup.3, C≡C, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═Se, C═NR.sup.3, P(═O)(R.sup.3), SO, SO.sub.2, NR.sup.3, O, S or CONR.sup.3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.3 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 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 R.sup.3 radicals, or a combination of two or more of these groups; at the same time, two or more adjacent R.sup.2 radicals together may form a mono- or polycyclic, aliphatic or aromatic ring system; R.sup.3 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 R.sup.3 substituents together may also form a mono- or polycyclic aliphatic or aromatic ring system.

13. The composition according to claim 11, wherein the electron-transporting host is a compound of the general formula (2) or (2a) ##STR00174## where the symbols and indices used are as follows: E is a single bond or NAr.sup.4; X is C when Ar.sup.1 is a 6-membered aryl or 6-membered heteroaryl group, or is C or N when Ar.sup.1 is a 5-membered heteroaryl group; Ar.sup.1 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; Ar.sup.2 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, Ar.sup.2 may also be joined to Ar.sup.3 by a single bond; Ar.sup.3 is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.5).sub.2, N(R.sup.6).sub.2, C(═O)Ar.sup.5, C(═O)R.sup.6, P(═O)(Ar.sup.5).sub.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 R.sup.6 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.6C═CR.sup.6, C≡C, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, C═O, C═S, C═Se, C═NR.sup.6, P(═O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.6 radicals, an aryloxy or heteroaryloxy group which has 5 to 30 aromatic ring atoms and may be substituted by one or more R.sup.6 radicals, or a combination of these systems; at the same time, Ar.sup.3 may also be joined to Ar.sup.2 by a single bond; Ar.sup.4 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, Ar.sup.4 may also be joined to Ar.sup.2 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 Ar.sup.1, Ar.sup.2, Ar.sup.3 or Ar.sup.4; R is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.5).sub.2, N(R.sup.6).sub.2, C(═O)Ar.sup.5, C(═O)R.sup.6, P(═O)(Ar.sup.5).sub.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 R.sup.6 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.6C═CR.sup.6, C≡C, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, C═O, C═S, C═Se, C═NR.sup.6, P(═O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.6 radicals, an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.6 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 R.sup.6 radicals; R.sup.6 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.5).sub.2, N(R.sup.7).sub.2, C(═O)Ar.sup.5, C(═O)R.sup.7, P(═O)(Ar.sup.5).sub.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 R.sup.7 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.7C═CR.sup.7, C≡C, Si(R.sup.7).sub.2, Ge(R.sup.7).sub.2, Sn(R.sup.7).sub.2, C═O, C═S, C═Se, C═NR.sup.7, P(═O)(R.sup.7), SO, SO.sub.2, NR.sup.7, O, S or CONR.sup.7 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.7 radicals, an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.7 radicals, or a combination of these systems; where it is optionally possible for two or more adjacent R.sup.6 substituents to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R.sup.7 radicals; Ar.sup.5 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 R.sup.7 radicals; at the same time, two Ar.sup.5 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(R.sup.7).sub.2 and O; R.sup.7 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 R.sup.7 substituents together may forma mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system.

14. The composition according to claim 1 wherein in compounds of the formula (2) or (2a), the Ar.sup.1 group is a group of the formula (3), (4), (5), (6) or (7) ##STR00175## where the dotted bond indicates the linkage to the carbonyl group, * indicates the position of the linkage to E and in addition: W is the same or different at each instance and is CR or N; or two adjacent W groups are a group of the following formula (8) or (9) ##STR00176## where G is CR.sup.2, NR, O or S, Z is the same or different at each instance and is CR or N and {circumflex over ( )} indicates the corresponding adjacent W groups in the formula (3) to (7); V is NR, O or S; and in that the Ar.sup.2 group is a group of one of the formulae (10), (11) and (12) ##STR00177## where the dotted bond indicates the linkage to N, # indicates the position of a possible linkage to Ar.sup.3, * indicates the linkage to E, and W and V have the definitions given above; and in that the Ar.sup.3 group is a group of one of the formulae (13), (14), (15) and (16) ##STR00178## where the dotted bond indicates the linkage to N, * indicates a possible linkage to Ar.sup.2, and W and V have the definitions given in claim 1.

15. The composition according to claim 1 wherein the compound of the formula (2) is selected from the compounds of the formulae (17) to (32) ##STR00179## ##STR00180## ##STR00181## where the symbols used have the definitions given in claim 1.

16. The composition according to claim 1, wherein the compound of the formula (2) is selected from the compounds of the formulae (17a) to (32a) ##STR00182## ##STR00183## ##STR00184## n claim 1.

17. The composition according to claim 1, wherein the compound of the formula (2) is selected from the compounds of the formulae (17b) to (32b) ##STR00185## ##STR00186## ##STR00187## ##STR00188## where the symbols used have the definitions given in claim 1.

18. The composition according to claim 1, wherein the composition further comprises at least one compound selected from the group consisting of hole injection materials, hole transport materials, hole blocker materials, wide band gap materials, fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron blocker materials, electron transport materials and electron injection materials, n-dopants and p-dopants.

19. A formulation comprising a composition according to claim 1 and at least one solvent.

20. An organic electronic device comprising at least one composition according to claim 1.

21. The organic electronic device according to claim 20, wherein the device is selected from organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors and organic photoreceptors.

22. The organic electronic device according to claim 21, wherein the organic electroluminescent device selected from the group consisting of organic light-emitting transistors (OLETs), organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O-lasers) and organic light-emitting diodes (OLEDs).

23. An organic electroluminescent device comprising the composition according to claim 1 in the emission layer together with a phosphorescent emitter.

24. The composition according to claim 11, wherein the composition further comprises at least one compound selected from the group consisting of hole injection materials, hole transport materials, hole blocker materials, wide band gap materials, fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron blocker materials, electron transport materials and electron injection materials, n-dopants and p-dopants.

25. A formulation comprising a composition according to claim 11 and at least one solvent.

26. An organic electronic device comprising at least one composition according to claim 11.

27. An organic electroluminescent device comprising the composition according to claim 11 in the emission layer together with a phosphorescent emitter.

28. The composition according to claim 12, wherein the electron-transporting host is a compound of the general formula (2) or (2a) ##STR00189## where the symbols and indices used are as follows: E is a single bond or NAr.sup.4; X is C when Ar.sup.1 is a 6-membered aryl or 6-membered heteroaryl group, or is C or N when Ar.sup.1 is a 5-membered heteroaryl group; Ar.sup.1 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; Ar.sup.2 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, Ar.sup.2 may also be joined to Ar.sup.3 by a single bond; Ara is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar.sup.5).sub.2, N(R.sup.6).sub.2, C(═O)Ar.sup.5, C(═O)R.sup.6, P(═O)(Ar.sup.5).sub.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 R.sup.6 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.6C═CR.sup.6, C≡C, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, C═O, C═S, C═Se, C═NR.sup.6, P(═O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.6 radicals, an aryloxy or heteroaryloxy group which has 5 to 30 aromatic ring atoms and may be substituted by one or more R.sup.6 radicals, or a combination of these systems; at the same time, Ar.sup.3 may also be joined to Ar.sup.2 by a single bond; Ar.sup.4 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, Ar.sup.4 may also be joined to Ar.sup.2 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 Ar.sup.1, Ar.sup.2, Ar.sup.3 or Ar.sup.4; R is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar).sub.2, N(R.sup.6).sub.2, C(═O)Ar.sup.5, C(═O)R.sup.6, P(═O)(Ar.sup.5).sub.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 R.sup.6 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.6C═CR.sup.6, C≡C, Si(R.sup.6).sub.2, Ge(R.sup.6).sub.2, Sn(R.sup.6).sub.2, C═O, C═S, C═Se, C═NR.sup.6, P(═O)(R.sup.6), SO, SO.sub.2, NR.sup.6, O, S or CONR.sup.6 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.6 radicals, an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.6 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 R.sup.6 radicals; R.sup.6 is the same or different at each instance and is selected from the group consisting of H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar).sub.2, N(R.sup.7).sub.2, C(═O)Ar.sup.5, C(═O)R.sup.7, P(═O)(Ar.sup.5).sub.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 R.sup.7 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.7C═CR.sup.7, C≡C, Si(R.sup.7).sub.2, Ge(R.sup.7).sub.2, Sn(R.sup.7).sub.2, C═O, C═S, C═Se, C═NR.sup.7, P(═O)(R.sup.7), SO, SO.sub.2, NR.sup.7, O, S or CONR.sup.7 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, 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 R.sup.7 radicals, an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.7 radicals, or a combination of these systems; where it is optionally possible for two or more adjacent R.sup.6 substituents to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R.sup.7 radicals; Ar.sup.5 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 R.sup.7 radicals; at the same time, two Ar.sup.5 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(R.sup.7).sub.2 and O; R.sup.7 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 R.sup.7 substituents together may forma mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system.

29. The composition according to claim 12, wherein the composition further comprises at least one compound selected from the group consisting of hole injection materials, hole transport materials, hole blocker materials, wide band gap materials, fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron blocker materials, electron transport materials and electron injection materials, n-dopants and p-dopants.

30. A formulation comprising a composition according to claim 12 and at least one solvent.

31. An organic electronic device comprising at least one composition according to claim 12.

32. An organic electroluminescent device comprising the composition according to claim 12 in the emission layer together with a phosphorescent emitter.

Description

EXAMPLES

(1) Determination of Orbital Energies and Electronic States

(2) The HOMO and LUMO energies and the triplet level and the singlet levels of the materials are determined via quantum-chemical calculations. For this purpose, in the present case, the “Gaussian09, Revision D.01” software package (Gaussian Inc.) is used. For calculation of organic substances without metals (referred to as the “org.” method), a geometry optimization is first conducted by the semi-empirical method AM1 (Gaussian input line “#AM1 opt”) with charge 0 and multiplicity 1. Subsequently, on the basis of the optimized geometry, a (single-point) energy calculation is effected for the electronic ground state and the triplet level. This is done using the TDDFT (time dependent density functional theory) method B3PW91 with the 6-31G(d) basis set (Gaussian input line “#B3PW91/6-31G(d) td=(50-50,nstates=4)”) (charge 0, multiplicity 1). For organometallic compounds (referred to as the “M-org.” method), the geometry is optimized by the Hartree-Fock method and the LanL2 MB basis set (Gaussian input line “#HF/LanL2 MB opt”) (charge 0, multiplicity 1). The energy calculation is effected, as described above, analogously to that for the organic substances, except that the “LanL2DZ” basis set is used for the metal atom and the “6-31G(d)” basis set for the ligands (Gaussian input line “#B3PW91/gen pseudo=lanl2 td=(50-50,nstates=4)”). From the energy calculation, the HOMO is obtained as the last orbital occupied by two electrons (alpha occ. eigenvalues) and LUMO as the first unoccupied orbital (alpha virt. eigenvalues) in Hartree units, where HEh and LEh represent the HOMO energy in Hartree units and the LUMO energy in Hartree units respectively. This is used to determine the HOMO and LUMO value in electron volts, calibrated by cyclic voltammetry measurements, as follows:
HOMO (eV)=(HEh*27.212)*0.8308−1.118
LUMO (eV)=(LEh*27.212)*1.0658−0.5049

(3) These values are to be regarded as HOMO and as LUMO of the materials in the context of this application.

(4) The triplet level T1 of a material is defined as the relative excitation energy (in eV) of the triplet state having the lowest energy which is found by the quantum-chemical energy calculation.

(5) The singlet level S1 of a material is defined as the relative excitation energy (in eV) of the singlet state having the second-lowest energy which is found by the quantum-chemical energy calculation.

(6) The energetically lowest singlet state is referred to as S0.

(7) The method described herein is independent of the software package used and always gives the same results. Examples of frequently utilized programs for this purpose are “Gaussian09” (Gaussian Inc.) and Q-Chem 4.1 (Q-Chem, Inc.). In the present case, the energies are calculated using the software package “Gaussian09, Revision D.01”.

(8) Production of the OLEDs

(9) Examples I1 to I3 which follow (see Table 1) present the use of the composition of the invention in OLEDs.

(10) Pretreatment for Examples I1-I3:

(11) Glass plaques coated with structured ITO (indium tin oxide) of thickness 50 nm are treated prior to coating, first with an oxygen plasma, followed by an argon plasma. These plasma-treated glass plaques form the substrates to which the OLEDs are applied.

(12) The OLEDs basically have the following layer structure: substrate/hole injection layer (HIL)/hole transport layer (HTL)/electron blocker layer (EBL)/emission layer (EML)/optional hole blocker layer (HBL)/electron transport layer (ETL)/optional electron injection layer (EIL) and finally a cathode. The cathode is formed by an aluminium layer of thickness 100 nm. The exact structure of the OLEDs can be found in Table 1. The materials required for production of the OLEDs are shown in Table 2. The data of the OLEDs are listed in Table 3. Examples C1 to C4 are comparative examples according to the prior art; examples I1 to I3 show data of OLEDs of the invention. The HOMO and LUMO values of the compounds are collated in Table 4.

(13) All materials are applied by thermal vapour deposition in a vacuum chamber. In this case, the emission layer always consists of at least one matrix material (host material) and an emitting dopant (emitter) which is added to the matrix material(s) in a particular proportion by volume by co-evaporation. Details given in such a form as L1:CbzT1:TEG1 (45%:45%:10%) mean here that the material L1 is present in the layer in a proportion by volume of 45%, CbzT1 in a proportion of 45% and TEG1 in a proportion of 10%. Analogously, the electron transport layer may also consist of a mixture of two materials.

(14) The OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectra, the current efficiency (CE, measured in cd/A) and the external quantum efficiency (EQE, measured in %) are determined as a function of luminance, calculated from current-voltage-luminance characteristics assuming Lambertian emission characteristics, as is the lifetime. The electroluminescence spectra are determined at a luminance of 1000 cd/m2, and the CIE 1931 x and y colour coordinates are calculated therefrom. The parameter U1000 in Table 3 refers to the voltage which is required for a luminance of 1000 cd/m2. CE1000 and EQE1000 respectively denote the current efficiency and external quantum efficiency that are attained at 1000 cd/m.sup.2.

(15) The lifetime LT is defined as the time after which the luminance drops from the starting luminance to a certain proportion L1 in the course of operation with constant current density j.sub.0. A figure of L1=80% in Table 3 means that the lifetime reported in the LT column corresponds to the time after which the luminance falls to 80% of its starting value.

(16) Use of Compositions of the Invention in OLEDs

(17) The materials of the invention can be used in the emission layer in phosphorescent green OLEDs. The inventive compounds CbBzT4 and L2 are used in Examples I1 to 13 as matrix material in the emission layer. In addition, the materials of the invention can be used in the electron transport layer (ETL), electron injection layer (EIL), hole blocker layer (HBL) or electron blocker layer (EBL).

(18) The examples are elucidated in detail hereinafter, in order to illustrate the advantages of the OLEDs of the invention.

(19) Use of Compositions of the Invention in the Emission Layer of Phosphorescent OLEDs

(20) Through the use of compounds according to prior art, i.e. the combination of two electron-transporting hosts (e.g. a lactam derivative and a triazine-carbazole derivative) with a hole-transporting emitter, it is possible to achieve good voltages, efficiencies and lifetimes with moderate emitter concentrations in the EML of 10% (C1 to C3). As expected, the use of smaller emitter concentrations of <10% according to Example C3 leads to a distinct reduction in lifetime, since the balance of electron current and hole current has been lost. The combination of an electron-transporting host and a bipolar host, where both are from the class of the triazine-carbazole derivatives, by contrast, leads to an improvement in lifetime (C4) even at low emitter concentrations (7%).

(21) An excellent improvement in lifetime with simultaneously low emitter concentration (7%) in the EML is obtained via the specific combination of an electron-transporting host from the class of the lactams and a bipolar host from the class of the triazine-carbazole derivatives (11 to 12). Even with very low emitter concentrations of 3%, it is possible to achieve an improvement in lifetime by about a factor of 2 (13) compared to the prior art (C1 to C3).

(22) At the same time, the low operating voltage of the OLEDs in 11 to 13 is maintained. Compared to the prior art, it is also possible to achieve excellent efficiencies.

(23) According to the model of examples 11 to 13, through the combination of further bipolar triazine-carbazole compounds (left-hand column of Table 5) with electron-conducting lactams (right-hand column of Table 5) and phosphorescent emitters, OLEDs having excellent performance data are obtained, which demonstrates the broad applicability of the material combination of the invention.

(24) TABLE-US-00010 TABLE 1 Structure of the OLEDs HIL/HTL HTL/HIL EML ETL EIL Ex thickness thickness EBL thickness thickness HBL thickness thickness thickness C1 SpA1 HATCN SpMA1 L1:CbzT1:TEG1 — ST2:LiQ — 70 nm  5 nm 90 nm (45%:45%:10%) (50%:50%) 40 nm 30 nm C2 SpA1 HATCN SpMA1 L1:CbzT3:TEG1 IC1 ST2:LiQ — 70 nm  5 nm 90 nm (45%:45%:10%)  5 nm (50%:50%) 40 nm 25 nm C3 SpA1 HATCN SpMA1 L2:CbzT1:TEG1 — ST2 LiQ 1 nm 70 nm  5 nm 90 nm (45%:45%:10%) 30 nm 40 nm C4 HATCN SpMA1 SpMA2 CbzT2:CbzT4:TEG2 ST2 ST2:LiQ LiQ 1 nm  5 nm 215 nm 20 nm (475%:46%:07%) 10 nm (50%:50%) 30 nm 30 nm I1 HATCN SpMA1 SpMA2 L2:CbzT4:TEG2 ST2 ST2:LiQ LiQ 1 nm  5 nm 215 nm 20 nm (47%:46%:07%) 10 nm (50%:50%) 30 nm 30 nm I2 HATCN SpMA1 SpMA2 L2:CbzT4:TEG3 ST2 ST2:LiQ LiQ 1 nm  5 nm 215 nm 20 nm (47%:46%:07%) 10 nm (50%:50%) 30 nm 30 nm I3 HATCN SpMA1 SpMA2 L2:CbzT4:TEG3 ST2 ST2:LiQ LiQ 1 nm  5 nm 215 nm 20 nm (48%:49%:03%) 10 nm (50%:50%) 30 nm 30 nm

(25) TABLE-US-00011 TABLE 2 Structural formulae of the materials for the OLEDs 0 0

(26) TABLE-US-00012 TABLE 3 Data of the OLEDs U1000 CE1000 EQE 1000 CIE x/y at j.sub.0 L1 LT Ex (V) (cd/A) (%) 1000 cd/m.sup.2 (mA/cm.sup.2) (%) (h) C1 2.9 62 17.2 0.33/0.62 20 80 260 C2 3.4 55 15.4 0.33/0.63 20 80 215 C3 2.6 59 16.4 0.33/0.62 20 80 165 C4 3.1 66 17.9 0.35/0.62 20 60 620 I1 3.2 70 18.9 0.32/0.64 20 80 750 I2 3.1 72 19.0 0.37/0.61 20 80 1110  I3 3.1 70 18.4 0.37/0.61 20 80 500

(27) TABLE-US-00013 TABLE 4 HOMO and LUMO values of the compounds Compound HOMO (eV) LUMO (eV) L1 −5.97 −2.49 L2 −5.97 −2.50 CbzT1 −5.60 −2.55 CbzT2 −5.53 −2.64 CbzT3 −5.43 −2.37 CbzT4 −5.31 −2.59

(28) TABLE-US-00014 TABLE 5 Structural formulae for further material combinations Carbazole-triazines (CbzT) Lactams (L) 0