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SULFUROUS COMPOUNDS FOR ORGANIC ELECTROLUMINESCENT DEVICES

20230422610 ยท 2023-12-28

    Inventors

    Cpc classification

    International classification

    Abstract

    The present invention relates to sulfurous compounds which are suitable for use in electronic devices, and to electronic devices, in particular organic electroluminescent devices containing said compounds.

    Claims

    1.-20. (canceled)

    21. A compound comprising at least one structure of the formula (1): ##STR00512## where the symbols and indices used are as follows: T is a heteroaromatic 5-membered ring which has a sulfur atom and is fused to the azole ring via two adjacent and mutually bonded carbon atoms and which may be substituted by one or more R.sup.3 groups; L is a connecting group which is selected from a bond or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals; X is N, CR, or C if an L, Y.sup.1 or Y.sup.2 group binds thereto, with the proviso that not more than two of the X groups in one cycle are N; X.sup.1 is N, CR.sup.1, or C if the L group binds thereto, with the proviso that not more than two of the X groups in one cycle are N; Y is NAr, NL, O, S, C(R.sup.2).sub.2, C(L)(R.sup.2), where NL means that the L group binds to the nitrogen atom of the NL group, and C(L)(R.sup.2) means that the L group binds to the carbon atom of the C(L)(R.sup.2) group; Y.sup.1 is a bond, NL, NR.sup.2, NAr, O, S, C(R.sup.2).sub.2, where NL means that the L group binds to the nitrogen atom of the NL group; r is 0 or 1, where r=0 means that the Y.sup.1 group is absent; Y.sup.2 is a bond, NL, NR.sup.2, NAr, O, S, C(R.sup.2).sub.2, where NL means that the L group binds to the nitrogen atom of the NL group; s is 0 or 1, where s=0 means that the Y.sup.2 group is absent; Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals; R is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.4).sub.2, N(Ar).sub.2, CN, NO.sub.2, OR.sup.4, SR.sup.4, COOR.sup.4, C(O)N(R.sup.4).sub.2, Si(R.sup.4).sub.3, B(OR.sup.4).sub.2, C(O)R.sup.4, P(O)(R.sup.4).sub.2, S(O)R.sup.4, S(O).sub.2R.sup.4, OSO.sub.2R.sup.4, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.4 radicals and where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.4).sub.2, CO, NR.sup.4, O, S or CONR.sup.4, 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.4 radicals; at the same time, two R radicals together, or one R radical together with an R.sup.2, R.sup.3 radical, may also form an aliphatic or heteroaliphatic ring system; R.sup.1 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.4).sub.2, N(Ar).sub.2, CN, NO.sub.2, OR.sup.4, SR.sup.4, COOR.sup.4, C(O)N(R.sup.4).sub.2, Si(R.sup.4).sub.3, B(OR.sup.4).sub.2, C(O)R.sup.4, P(O)(R.sup.4).sub.2, S(O)R.sup.4, S(O).sub.2R.sup.4, OSO.sub.2R.sup.4, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.4 radicals and where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.4).sub.2, CO, NR.sup.4, O, S or CONR.sup.4, 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.4 radicals; at the same time, two R.sup.1 radicals together or one R.sup.1 radical together with one R.sup.2 radical may also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.4).sub.2, N(Ar).sub.2, CN, NO.sub.2, OR.sup.4, SR.sup.4, COOR.sup.4, C(O)N(R.sup.4).sub.2, Si(R.sup.4).sub.3, B(OR.sup.4).sub.2, C(O)R.sup.4, P(O)(R.sup.4).sub.2, S(O)R.sup.4, S(O).sub.2R.sup.4, OSO.sub.2R.sup.4, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.4 radicals and where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.4).sub.2, CO, NR.sup.4, O, S or CONR.sup.4, 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.4 radicals; at the same time, two R.sup.2 radicals together or one R.sup.2 radical together with one R, R.sup.1, R.sup.3 radical may also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; R.sup.3 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.4).sub.2, N(Ar).sub.2, CN, NO.sub.2, OR.sup.4, SR.sup.4, COOR.sup.4, C(O)N(R.sup.4).sub.2, Si(R.sup.4).sub.3, B(OR.sup.4).sub.2, C(O)R.sup.4, P(O)(R.sup.4).sub.2, S(O)R.sup.4, S(O).sub.2R.sup.4, OSO.sub.2R.sup.4, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.4 radicals and where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.4).sub.2, CO, NR.sup.4, O, S or CONR.sup.4, 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.4 radicals; at the same time, two R.sup.3 radicals together or one R.sup.3 radical together with one R, R.sup.2 radical may also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.4 radicals; R.sup.4 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.5).sub.2, CN, NO.sub.2, OR S, SR S, Si(R.sup.5).sub.3, B(OR.sup.5).sub.2, C(O)R.sup.5, P(O)(R.sup.5).sub.2, S(O)R.sup.5, S(O).sub.2R.sup.5, OSO.sub.2R.sup.5, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.5 radicals and where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.5).sub.2, CO, NR.sup.5, O, S or CONR.sup.5, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R.sup.2 radicals; at the same time, two or more R.sup.4 radicals together may form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; R.sup.5 is the same or different at each instance and is H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F; where the sum of r and s is 1 or 2.

    22. The compound as claimed in claim 21, wherein the compound comprises at least one structure of the formulae (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), (1i), (1j), (1k), (1l), (1m), (1n), (1o), (1p), (1q), (1r), (1s), (1t), (1u), (1v), (1w), (1x), (1y), (1z) and (1za): ##STR00513## ##STR00514## ##STR00515## ##STR00516## ##STR00517## ##STR00518## where Y, Y.sup.1, Y.sup.2, X, X.sup.1, s, and R.sup.3 have the definitions given in claim 21, j is 0, 1 or 2, and k is 0 or 1, where s+k=0 or 1 and j+s=0, 1 or 2.

    23. The compound as claimed in claim 21, wherein the compound comprises at least one structure of the formulae (2a), (2b), (2c), (2d), (2e), (2f), (2g), (2h), (2i), (2j), (2k), (2l), (2m), (2n), (2o), (2p), (2q), (2r), (2s), (2t), (2u), (2v), (2w), (2x), (2y), (2z) and (2za): ##STR00519## ##STR00520## ##STR00521## ##STR00522## ##STR00523## ##STR00524## where L, Y, R, R.sup.1 and R.sup.3 have the definitions given in claim 21, the index k is 0 or 1, the index j is 0, 1 or 2, the index n is 0, 1, 2 or 3, and the index m is 0, 1, 2, 3 or 4.

    24. The compound as claimed in claim 21, wherein the compound comprises at least one structure of the formulae (3a), (3b), (3c), (3d), (3e), (3f), (3g), (3h), (3i), (3j), (3k), (3l), (3m), (3n), (3o), (3p), (3q) and (3r): ##STR00525## ##STR00526## ##STR00527## ##STR00528## ##STR00529## where L, Y, R, R.sup.1 and R.sup.3 have the definitions given in claim 21, the index k is 0 or 1, the index n is 0, 1, 2 or 3 and the index m is 0, 1, 2, 3 or 4.

    25. The compound as claimed in claim 21, wherein the compound comprises at least one structure of the formulae (4a), (4b), (4c), (4d), (4e), (4f), (4g), (4h), (4i), (4j), (4k), (4l), (4m), (4n), (4o), (4p), (4q) and (4r): ##STR00530## ##STR00531## ##STR00532## ##STR00533## where L, Y, R, R.sup.1 and R.sup.3 have the definitions given in claim 21, the index k is 0 or 1, the index j is 0, 1 or 2, the index n is 0, 1, 2 or 3, and the index m is 0, 1, 2, 3 or 4.

    26. The compound as claimed in claim 21, wherein the compound comprises at least one structure of the formulae (5a), (5b), (5c), (5d), (5e), (5f), (5g), (5h) and (5i): ##STR00534## ##STR00535## ##STR00536## where L, Y, R, R.sup.1 and R.sup.3 have the definitions given in claim 21, the index k is 0 or 1, the index j is 0, 1 or 2, the index n is 0, 1, 2 or 3, and the index m is 0, 1, 2, 3 or 4,

    27. The compound as claimed in claim 21, wherein the compound comprises at least one structure of the formulae (6a), (6b), (6c), (6d), (6e), (6f), (6g) and (6h): ##STR00537## ##STR00538## where L, Y, R, R.sup.1 and R.sup.3 have the definitions given in claim 21, the index k is 0 or 1; the index j is 0, 1 or 2; the index n is 0, 1, 2 or 3; and the index m is 0, 1, 2, 3 or 4.

    28. The compound as claimed in claim 21, wherein L is a bond or is a group selected from the formulae (L.sup.1-1) to (L.sup.1-16): ##STR00539## ##STR00540## ##STR00541## where the dotted bonds each mark the positions of attachment; Y.sup.3 is the same or different at each instance and is O, S, NAr, NR.sup.2; the index k is 0 or 1; the index l is 0, 1 or 2; the index j is independently at each instance 0, 1, 2 or 3; the index h is independently at each instance 0, 1, 2, 3 or 4; the index g is 0, 1, 2, 3, 4 or 5; and the symbol R.sup.2 has the definition given in claim 21, where L is a bond or is an aromatic ring system which has 5 to 40 aromatic ring atoms and does not comprise any heteroatoms.

    29. The compound as claimed in claim 21, wherein L is a bond and Y is NAr, O or S.

    30. The compound as claimed in claim 21, wherein R, R.sup.1, R.sup.2 and/or R.sup.3 are the same or different at each instance and are selected from the group consisting of H, D or an aromatic or heteroaromatic ring system selected from the groups of the following formulae Ar-1 to Ar-75, and/or the Ar group is the same or different at each instance and is selected from the groups of the following formulae Ar-1 to Ar-75: ##STR00542## ##STR00543## ##STR00544## ##STR00545## ##STR00546## ##STR00547## ##STR00548## ##STR00549## ##STR00550## ##STR00551## ##STR00552## ##STR00553## ##STR00554## ##STR00555## ##STR00556## ##STR00557## where R.sup.4 has the definitions given above, the dotted bond represents the bond of the corresponding group and in addition: Ar.sup.1 is the same or different at each instance and is a bivalent aromatic or heteroaromatic ring system which has 6 to 18 aromatic ring atoms and may be substituted in each case by one or more R.sup.4 radicals; A is the same or different at each instance and is C(R.sup.4).sub.2, NR.sup.4, O or S; p is 0 or 1, where p=0 means that the Ar.sup.1 group is absent and that the corresponding aromatic or heteroaromatic group is bonded directly to the corresponding radical; q is 0 or 1, where q=0 means that no A group is bonded at this position and R.sup.4 radicals are bonded to the corresponding carbon atoms instead.

    31. A process for preparing the compound as claimed in claim 21, which comprises reacting a thiofuran compound with an aromatic or heteroaromatic nitrogen compound by a coupling reaction.

    32. A composition comprising at least one compound as claimed in claim 21 and at least one further matrix material, wherein the further matrix material is selected from compounds of one of the formulae (7), (8), (9) and (10): ##STR00558## where the symbols and indices used are as follows: R.sup.6 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.7).sub.2, N(Ar).sub.2, CN, NO.sub.2, OR.sup.7, SR.sup.7, COOR.sup.7, C(O)N(R.sup.7).sub.2, Si(R.sup.7).sub.3, B(OR.sup.7).sub.2, C(O)R.sup.7, P(O)(R.sup.7).sub.2, S(O)R.sup.7, S(O).sub.2R.sup.7, OSO.sub.2R.sup.7, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.7 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.7).sub.2, CO, NR.sup.7, O, S or CONIC, 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.7 radicals; at the same time, two R.sup.6 radicals together may also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.7 radicals; A.sup.1 is C(R.sup.7).sub.2, NR.sup.7, O or S; Ar.sup.5 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.7 radicals; R.sup.7 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.8).sub.2, CN, NO.sub.2, OR.sup.8, SR.sup.8, Si(R.sup.8).sub.3, B(OR.sup.8).sub.2, C(O)R.sup.8, P(O)(R.sup.8).sub.2, S(O)R.sup.8, S(O).sub.2R.sup.8, OSO.sub.2R.sup.8, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.8 radicals and where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.8).sub.2, CO, NR.sup.8, O, S or CONR.sup.8, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R.sup.8 radicals; at the same time, two or more R.sup.7 radicals together may form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; R.sup.8 is the same or different at each instance and is H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F; s is the same or different at each instance and is 0, 1, 2, 3 or 4; t is the same or different at each instance and is 0, 1, 2 or 3; and u is the same or different at each instance and is 0, 1 or 2.

    33. A composition comprising at least one compound as claimed in claim 21 and at least one further matrix material, wherein the further matrix material is selected from compounds of one of the formulae (11), (12), (13), (14), (15), (16), (17) and (18): ##STR00559## ##STR00560## where the symbols and indices used are as follows: X.sup.2 is N or CR.sup.9, with the proviso that not more than two of the X.sup.2 groups in one cycle are N; L.sup.2 is a connecting group which is selected from a bond or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.9 radicals; Ar.sup.6 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.10 radicals; R.sup.9 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.10).sub.2, N(Ar).sub.2, CN, NO.sub.2, OR.sup.10, SR.sup.10, COOR.sup.10, C(O)N(R.sup.10).sub.2, Si(R.sup.10).sub.3, B(OR.sup.10).sub.2, C(O)R.sup.10, P(O)(R.sup.10).sub.2, S(O)R.sup.10, S(O).sub.2R.sup.10, OSO.sub.2R.sup.10, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.4 radicals and where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.10).sub.2, CO, NR.sup.10, O, S or CONR.sup.10, 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.10 radicals; at the same time, two R.sup.9 radicals together may also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.10 radicals; A.sup.2 is C(R.sup.10).sub.2, NR.sup.10, O or S; R.sup.10 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.11).sub.2, CN, NO.sub.2, OR.sup.11, SR.sup.11, Si(R.sup.11).sub.3, B(OR.sup.11).sub.2, C(O)R.sup.11, P(O)(R.sup.11).sub.2, S(O)R.sup.11, S(O).sub.2R.sup.11, OSO.sub.2R.sup.11, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.11 radicals and where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.11).sub.2, CO, NR.sup.11, O, S or CONR.sup.11, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R.sup.11 radicals; at the same time, two or more R.sup.10 radicals together may form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; R.sup.11 is the same or different at each instance and is H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F; v is the same or different at each instance and is 0, 1, 2, 3 or 4 t is the same or different at each instance and is 0, 1, 2 or 3; x is the same or different at each instance and is 0, 1, 2, 3 or 4; z is the same or different at each instance and is 0, 1 or 2, where the sum total of x and 2z is not more than 4.

    34. The composition as claimed in claim 32, wherein the compound has a proportion by mass in the composition in the range from 10% by weight to 95% by weight, based on the total mass of the composition.

    35. The composition as claimed in claim 33, wherein the compounds of one of the formulae (7), (8), (9), (10), (11), (12), (13), (14), (15), (16), (17) and (18) have a proportion by mass in the composition in the range from 5% by weight to 90% by weight, based on the overall composition ##STR00561## where the symbols and indices used are as follows: R.sup.6 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.7).sub.2, N(Ar).sub.2, CN, NO.sub.2, OR.sup.7, SR.sup.7, COOR.sup.7, C(O)N(R.sup.7).sub.2, Si(R.sup.7).sub.3, B(OR.sup.7).sub.2, C(O)R.sup.7, P(O)(R.sup.7).sub.2, S(O)R.sup.7, S(O).sub.2R.sup.7, OSO.sub.2R.sup.7, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.7 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.7).sub.2, CO, NR.sup.7, O, S or CONR.sup.7, 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.7 radicals; at the same time, two R.sup.6 radicals together may also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.7 radicals; A.sup.1 is C(R.sup.7).sub.2, NR.sup.7, O or S; Ar.sup.5 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.7 radicals; R.sup.7 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.8).sub.2, CN, NO.sub.2, OR.sup.8, Si(R.sup.8).sub.3, B(OR.sup.8).sub.2, C(O)R.sup.8, P(O)(R.sup.8).sub.2, S(O)R.sup.8, S(O).sub.2R.sup.8, OSO.sub.2R.sup.8, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.8 radicals and where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.8).sub.2, CO, NR.sup.8, O, S or CONR.sup.8, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R.sup.8 radicals; at the same time, two or more R.sup.7 radicals together may form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; R.sup.8 is the same or different at each instance and is H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F; s is the same or different at each instance and is 0, 1, 2, 3 or 4; t is the same or different at each instance and is 0, 1, 2 or 3; and u is the same or different at each instance and is 0, 1 or 2.

    36. A formulation comprising at least one compound as claimed in claim 21 and at least one further compound.

    37. A formulation comprising at least one composition as claimed in claim 32 and at least one further compound.

    38. The formulation as claimed in claim 36, wherein the at least one further compound is a solvent.

    39. An electronic device comprising at least one compound as claimed in claim 21.

    40. An electronic device comprising the composition as claimed in claim 32.

    41. The electronic device as claimed in claim 39, wherein the electronic device is an electroluminescent device.

    42. An organic electroluminescent device, which comprises the compound as claimed in claim 21 is used as matrix material in an emitting layer and/or in an electron transport layer and/or in a hole blocker layer and/or in a hole transport layer and/or in an electron blocker layer.

    43. An electronic device which comprises the compound as claimed in claim 21 is used as matrix material for phosphorescent emitters in combination with a further matrix material, where the further matrix material is selected from compounds of one of the formulae (7), (8), (9) and (10): ##STR00562## wherein R.sup.6 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.7).sub.2, N(Ar).sub.2, CN, NO.sub.2, OR.sup.7, SR.sup.7, COOR.sup.7, C(O)N(R.sup.7).sub.2, Si(R.sup.7).sub.3, B(OR.sup.7).sub.2, C(O)R.sup.7, P(O)(R.sup.7).sub.2, S(O)R.sup.7, S(O).sub.2R.sup.7, OSO.sub.2R.sup.7, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.7 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.7).sub.2, CO, NR.sup.7, O, S or CONIC, 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.7 radicals; at the same time, two R.sup.6 radicals together may also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.7 radicals; A.sup.1 is C(R.sup.7).sub.2, NR.sup.7, O or S; Ar.sup.5 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.7 radicals; R.sup.7 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.8).sub.2, CN, NO.sub.2, OR.sup.8, SR.sup.8, Si(R.sup.8).sub.3, B(OR.sup.8).sub.2, C(O)R.sup.8, P(O)(R.sup.8).sub.2, S(O)R.sup.8, S(O).sub.2R.sup.8, OSO.sub.2R.sup.8, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.8 radicals and where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.8).sub.2, CO, NR.sup.8, O, S or CONR.sup.8, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R.sup.8 radicals; at the same time, two or more R.sup.7 radicals together may form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; R.sup.8 is the same or different at each instance and is H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F; s is the same or different at each instance and is 0, 1, 2, 3 or 4; t is the same or different at each instance and is 0, 1, 2 or 3; u is the same or different at each instance and is 0, 1 or 2; and/or the further matrix material is selected from compounds of one of the formulae (11), (12), (13), (14), (15), (16), (17) and (18), ##STR00563## ##STR00564## wherein X.sup.2 is N or CR.sup.9, with the proviso that not more than two of the X.sup.2 groups in one cycle are N; L.sup.2 is a connecting group which is selected from a bond or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.9 radicals; Ar.sup.6 is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.10 radicals; R.sup.9 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.10).sub.2, N(Ar).sub.2, CN, NO.sub.2, OR.sup.10, SR.sup.10, COOR.sup.10, C(O)N(R.sup.10).sub.2, Si(R.sup.10).sub.3, B(OR.sup.10).sup.2, C(O)R.sup.10, P(O)(R.sup.10).sub.2, S(O)R.sup.10, S(O).sub.2R.sup.10, OSO.sub.2R.sup.10, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.4 radicals and where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.10).sub.2, CO, NR.sup.10, O, S or CONR.sup.10, 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.10 radicals; at the same time, two R.sup.9 radicals together may also form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.10 radicals; A.sup.2 is C(R.sup.10).sub.2, NR.sup.10, O or S; R.sup.10 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R.sup.11).sub.2, CN, NO.sub.2, OR.sup.11, SR.sup.11, Si(R.sup.11).sub.3, B(OR.sup.11).sub.2, C(O)R.sup.11, P(O)(R.sup.11).sub.2, S(O)R.sup.11, S(O).sub.2R.sup.11, OSO.sub.2R.sup.11, a straight-chain alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, where the alkyl, alkenyl or alkynyl group may in each case be substituted by one or more R.sup.11 radicals and where one or more nonadjacent CH.sub.2 groups may be replaced by Si(R.sup.11).sub.2, CO, NR.sup.11, O, S or CONR.sup.11, or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R.sup.11 radicals; at the same time, two or more R.sup.10 radicals together may form an aromatic, heteroaromatic, aliphatic or heteroaliphatic ring system; R.sup.11 is the same or different at each instance and is H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, especially a hydrocarbyl radical, having 1 to 20 carbon atoms, in which one or more hydrogen atoms may also be replaced by F; v is the same or different at each instance and is 0, 1, 2, 3 or 4 t is the same or different at each instance and is 0, 1, 2 or 3; x is the same or different at each instance and is 0, 1, 2, 3 or 4; z is the same or different at each instance and is 0, 1 or 2, where the sum total of x and 2z is not more than 4.

    Description

    EXAMPLES

    [0229] The syntheses which follow, unless stated otherwise, are conducted under a protective gas atmosphere in dried solvents. The solvents and reagents can be purchased, for example, from Sigma-ALDRICH or ABCR. For the compounds known from the literature, the corresponding CAS numbers are also reported in each case.

    Synthesis Examples

    [0230] a) Bromination

    ##STR00360##

    [0231] To a solution of 37 g (150 mmol) of thieno[2,3:4,5]pyrrolo[3,2,1-jk]carbazole in chloroform (900 ml) is added N-bromosuccinimide (26.6 g, 150 mmol) in portions at 10 C. with exclusion of light, and the mixture is stirred at this temperature for 2 h. The reaction is ended by addition of sodium sulfite solution and the mixture is stirred at room temperature for a further 30 min. After phase separation, the organic phase is washed with water and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried over sodium sulfate and concentrated under reduced pressure. The residue is dissolved in toluene and filtered through silica gel. Subsequently, the crude product is recrystallized from toluene/heptane.

    [0232] Yield: 34 g (106 mmol), 70% of theory, colorless solid.

    [0233] The following compounds are prepared in an analogous manner:

    TABLE-US-00003 Reactant 1 Product Yield 1a [00361]embedded image [00362]embedded image 75% [2201847-06-3] 2a [00363]embedded image [00364]embedded image 48% [2335876-25-8] 3a [00365]embedded image [00366]embedded image 72%

    [0234] b) Suzuki Reaction

    ##STR00367##

    [0235] 51.4 g (150 mmol) of compound a, 50 g (160 mmol) of N-phenylcarbazole-3-boronic acid and 36 g (340 mmol) of sodium carbonate are suspended in 1000 ml of ethylene glycol dimethyl ether and 280 ml of water. 1.8 g (1.5 mmol) of tetrakis(triphenylphosphine)palladium(0) are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is removed, filtered through silica gel, washed three times with 200 ml of water and then concentrated to dryness. The residue is subjected to hot extraction with toluene and recrystallized from toluene/n-heptane and finally sublimed under high vacuum.

    [0236] The yield is 51 g (104 mmol), corresponding to 67% of theory.

    [0237] The following compounds are prepared in an analogous manner:

    TABLE-US-00004 Reactant 1 Reactant 2 Product Yield 1b [00368]embedded image [00369]embedded image [00370]embedded image 67% 2b [00371]embedded image [00372]embedded image [00373]embedded image 63% 3b [00374]embedded image [00375]embedded image [00376]embedded image 63% 4b [00377]embedded image [00378]embedded image [00379]embedded image 67% 5b [00380]embedded image [00381]embedded image [00382]embedded image 69% 6b [00383]embedded image [00384]embedded image [00385]embedded image 66% 7b [00386]embedded image [00387]embedded image [00388]embedded image 64% 8b [00389]embedded image [00390]embedded image [00391]embedded image 70% 9b [00392]embedded image [00393]embedded image [00394]embedded image 73% 10b [00395]embedded image [00396]embedded image [00397]embedded image 61% 11b [00398]embedded image [00399]embedded image [00400]embedded image 64% 12b [00401]embedded image [00402]embedded image [00403]embedded image 66% 13b [00404]embedded image [00405]embedded image [00406]embedded image 68% 14b [00407]embedded image [00408]embedded image [00409]embedded image 70% 15b [00410]embedded image [00411]embedded image [00412]embedded image 78% 16b [00413]embedded image [00414]embedded image [00415]embedded image 66% 17b [00416]embedded image [00417]embedded image [00418]embedded image 69% 18b [00419]embedded image [00420]embedded image [00421]embedded image 62% 19b [00422]embedded image [00423]embedded image [00424]embedded image 71% 20b [00425]embedded image [00426]embedded image [00427]embedded image 70% 21b [00428]embedded image [00429]embedded image [00430]embedded image 68% 22b [00431]embedded image [00432]embedded image [00433]embedded image 73% 23b [00434]embedded image [00435]embedded image [00436]embedded image 65% 24b [00437]embedded image [00438]embedded image [00439]embedded image 71% 25b [00440]embedded image [00441]embedded image [00442]embedded image 66% 26b [00443]embedded image [00444]embedded image [00445]embedded image 70% 27b [00446]embedded image [00447]embedded image [00448]embedded image 75% 28b [00449]embedded image [00450]embedded image [00451]embedded image 72%

    [0238] c) Copper-Catalyzed Condensation

    ##STR00452##

    [0239] Under protective gas and without solvent, 10.6 g (44 mmol) of 3,4-dibromothiophene, 18 g (40 mmol) of 9-phenyl-3,3-bi-9H-carbazole, 6 g (44 mmol) of K.sub.2CO.sub.3 and 500 mg (2 mmol) of CuSO.sub.4-5H.sub.2O are stirred in a reaction vessel equipped with a stirrer bar and purged three times with argon. The reaction mixture is stirred under reflux (250 C.) for 24 h. After cooling, the mixture is admixed with 100 ml of dichloromethane and 100 ml of water, the organic phase is separated, dried over MgSO4 and filtered, and the solvent is removed under reduced pressure. The residue is purified by column chromatography using silica gel (eluent: DCM/heptane (1:3)).

    [0240] The yield is 7 g (12.5 mmol), corresponding to 48% of theory.

    [0241] The following compounds can be prepared analogously:

    TABLE-US-00005 Reactant 1 Reactant 2 Product Yield 1c [00453]embedded image [00454]embedded image [00455]embedded image 38% [1345202-03-0] 2c [00456]embedded image [00457]embedded image [00458]embedded image 34% [1345202-03-0] [859490-18-9] 3c [00459]embedded image [00460]embedded image [00461]embedded image 38% [1345202-03-0] [874511-95-2] 4c [00462]embedded image [00463]embedded image [00464]embedded image 41% [1345202-03-0] [2226857-79-4] 5c [00465]embedded image [00466]embedded image [00467]embedded image 37% [1345202-03-0] [140898-76-6] [00468]embedded image 37% 6c [00469]embedded image [00470]embedded image [00471]embedded image 31% [1346669-47-3] [2226857-79-4]

    [0242] d) CH-Activated Cyclization

    ##STR00472##

    [0243] A round-bottom flask is charged with 20.8 g (63.7 mmol) of compound b, 17.3 g (126 mmol) of K.sub.2CO.sub.3, 1.8 g (3.21 mmol) of (NHC)Pd(allyl)Cl, and then degassed and filled with argon. Under an argon atmosphere, 200 ml of degassed dimethylacetamide with a water content of less than 1000 ppm is added. The mixture is heated to 130 C. for 24 hours under an argon counterflow and stirred until completion. After cooling, 100 ml of dichloromethane and 100 ml of water are added to the mixture, the organic phase is separated, dried over MgSO4 and filtered, and the solvent is removed under reduced pressure. The residue is purified by column chromatography using silica gel (eluent: DCM/heptane (1:3)). The residue is subjected to hot extraction with toluene and recrystallized from toluene/n-heptane and finally sublimed under high vacuum. The yield is 10.5 (21.9 mmol) of the mixture of A+B, corresponding to 60% of theory. After column chromatography separation and subsequent workup, 22% A and 38% B are obtained.

    [0244] The following compounds can be prepared analogously:

    TABLE-US-00006 Reactant 1 Product A Product B Yield 1d [00473]embedded image [00474]embedded image [00475]embedded image 35% A 21% B 2d [00476]embedded image [00477]embedded image [00478]embedded image 32% A 18% B 3d [00479]embedded image [00480]embedded image [00481]embedded image 32% A 16% B 4d [00482]embedded image [00483]embedded image [00484]embedded image 30% A 15% B

    [0245] Production of the Electroluminescent Devices

    [0246] Examples E1 to E20 which follow (see table 1) present the use of the materials of the invention in electroluminescent devices.

    [0247] Pretreatment for examples E1-E20: Glass plates 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 plates form the substrates to which the OLEDs are applied.

    [0248] The electroluminescent devices 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 aluminum layer of thickness 100 nm. The exact structure of the OLEDs can be found in table 1. The materials required for production of the electroluminescent devices are shown in table 2. The data of the electroluminescent devices are listed in table 3.

    [0249] All materials are applied by thermal vapor deposition in a vacuum chamber. In this case, the emission layer always consists of at least one matrix material (host material), for the purposes of the invention at least two matrix materials, 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 2b:BisC1:TEG1 (45%:45%:10%) mean here that the material 2b is present in the layer in a proportion by volume of 45%, BisC1 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.

    [0250] The electroluminescent devices 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. Electroluminescence spectra are determined at a luminance of 1000 cd/m.sup.2, and these are used to calculate the CIE 1931 x and y color coordinates. The parameter U1000 in table 18 refers to the voltage which is required for a luminance of 1000 cd/m.sup.2. CE1000 and EQE1000 respectively denote the current efficiency and external quantum efficiency that are attained at 1000 cd/m.sup.2.

    [0251] Use of Mixtures of the Invention in Electroluminescent Devices

    [0252] The material combinations of the invention can be used in the emission layer in phosphorescent OLEDs. The inventive compounds 2b and 9b are used in examples E1 to E2 as green matrix material in the emission layer, and 10b and 18b are used in examples E16 to E17 as red matrix material in the emission layer.

    [0253] The inventive combination of compound BisC1 with corresponding compounds b, 2b and 9b are used in examples E3 to E5 as matrix material in the emission layer. Further inventive combinations of compounds 24a and 2 dB with compounds Tz1 to Tz8 are used in examples E6 to E15 as matrix material in the emission layer.

    [0254] A further inventive combination of compounds 18b with compound BisC2 is used in example E18 as red matrix material in the emission layer.

    [0255] In example E19, inventive compound 9b is used as electron blocker material in the EBL.

    [0256] In example E20, inventive compound 28b is used as hole transport material.

    TABLE-US-00007 TABLE 1 Structure of the electroluminescent devices HIL HTL EBL EML HBL ETL EIL Ex. thickness thickness thickness thickness thickness thickness thickness E1 HATCN SpMA1 SpMA2 2b: TEG1 ST2 ST2:LiQ LiQ 5 nm 125 nm 10 nm (97%:3%) 10 nm (50%:50%) 1 nm 35 nm 30 nm E2 HATCN SpMA1 SpMA2 9b: TEG1 ST2 ST2:LiQ LiQ 5 nm 125 nm 10 nm (97%:3%) 10 nm (50%:50%) 1 nm 35 nm 30 nm E3 HATCN SpMA1 SpMA2 2b:BisC1: ST2 ST2:LiQ LiQ 5 nm 125 nm 10 nm TEG1 10 nm (50%:50%) 1 nm ((46%:47%: 30 nm 7%) 30 nm E4 HATCN SpMA1 SpMA2 9b:BisC1: ST2 ST2:LiQ LiQ 5 nm 125 nm 10 nm TEG1 10 nm (50%:50%) 1 nm ((46%:47%: 30 nm 7%) 30 nm E5 HATCN SpMA1 SpMA2 b:BisC1: ST2 ST2:LiQ LiQ 5 nm 125 nm 10 nm TEG1 10 nm (50%:50%) 1 nm ((46%:47%: 30 nm 7%) 30 nm E6 HATCN SpMA1 SpMA2 24b:TZ1: ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm TEG1 10 nm (50%:50%) 1 nm (46%:47%: 30 nm 7%) 30 nm E7 HATCN SpMA1 SpMA2 24b:TZ2: ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm TEG1 10 nm (50%:50%) 1 nm (46%:47%: 30 nm 7%) 30 nm E8 HATCN SpMA1 SpMA2 24b:Tz3: ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm TEG1 10 nm (50%:50%) 1 nm (46%:47%: 30 nm 7%) 30 nm E9 HATCN SpMA1 SpMA2 24b:TZ4. ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm TEG1 10 nm (50%:50%) 1 nm (46%:47%: 30 nm 7%) 30 nm E10 HATCN SpMA1 SpMA2 24b:Tz5: ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm TEG1 10 nm (50%:50%) 1 nm (46%:47%: 30 nm 7%) 30 nm E11 HATCN SpMA1 SpMA2 24b:Tz6: ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm TEG1 10 nm (50%:50%) 1 nm (46%:47%: 30 nm 7%) 30 nm E12 HATCN SpMA1 SpMA2 24bTz7: ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm TEG1 10 nm (50%:50%) 1 nm (46%:47%: 30 nm 7%) 30 nm E13 HATCN SpMA1 SpMA2 24b:Tz8: ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm TEG1 10 nm (50%:50%) 1 nm (46%:47%: 30 nm 7%) 30 nm E14 HATCN SpMA1 SpMA2 2dB:Tz8: ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm TEG1 10 nm (50%:50%) 1 nm (46%:47%: 30 nm 7%) 30 nm E15 HATCN SpMA1 SpMA2 4dB:Tz8: ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm TEG1 10nm (50%:50%) 1 nm (46%:47%: 30 nm 7%) 30 nm E16 HATCN SpMA1 SpMA3 10b:-TER1 50 n ST2:LiQ LiQ 5 nm 125 nm 10 nm (97%:3%) 10 nm (50%:50%) 1 nm 35 nm 30 nm E17 HATCN SpMA1 SpMA3 18b:TER1 50 n ST2:n:LiQ LiQ 5 nm 125 nm 10 nm (97%:3%) 10 nm (50%:50%) 1 nm 35 nm 30 nm E18 HATCN SpMA1 SpMA3 18b: BisC2: 50 n ST2 :: LiQ LiQ 5 nm 125 nm 10 nm TER1 10 nm (50%:50%) 1 nm (57%:40%: 30 nm 3%) 35 nm E19 HATCN SpMA1 9b Tz4:BisC1: ST2 ST2:LiQ LiQ 5 nm 125 nm 10 nm TEG1 10 nm (50%:50%) 1 nm (46%:47%: 30 nm 7%) 30 nm E20 HATCN 28b SpMA3 TZ5: BisC1: 50 n ST2::LiQ LiQ 5 nm 125 nm 10 nm TEG1 10 nm (50%:50%) 1 nm (57%:40%: 30 nm 3%) 35 nm

    TABLE-US-00008 TABLE 2 Structural formulae of the materials for the electroluminescent devices [00485]embedded image [00486]embedded image [00487]embedded image [00488]embedded image [00489]embedded image [00490]embedded image [00491]embedded image [00492]embedded image [00493]embedded image [00494]embedded image [00495]embedded image [00496]embedded image [00497]embedded image [00498]embedded image [00499]embedded image [00500]embedded image [00501]embedded image [00502]embedded image [00503]embedded image [00504]embedded image [00505]embedded image [00506]embedded image [00507]embedded image [00508]embedded image [00509]embedded image [00510]embedded image [00511]embedded image

    TABLE-US-00009 TABLE 3 Performance date of the electroluminescent devices U1000 CE1000 EQE 1000 CIE x/y at Ex. (V) (cd/A) (%) 1000 cd/m.sup.2 E1 4.2 67 15.2 0.33/0.64 E2 4.0 69 16.0 0.32/0.63 E3 3.3 65 17.5 0.33/0.63 E4 3.2 71 17.9 0.31/0.64 E5 3.4 67 18 0.32/0.63 E6 3.5 74 18.0 0.33/0.63 E7 3.2 76 18.3 0.33/0.63 E8 3.3 69 18.5 0.31/0.64 E9 3.2 73 19.0 0.31/0.64 E10 3.4 75 17.4 0.32/0.64 E11 3.2 74 18.9 0.32/0.64 E12 3.2 78 18.0 0.31/0.63 E13 3.4 72 19.1 0.31/0.64 E14 3.5 66 17.3 0.32/0.64 E15 3.6 62 15.5 0.32/0.64 E16 3.9 28 20.6 0.67/0.34 E17 3.8 27 22.0 0.66/0.33 E18 3.4 29 22.9 0.67/0.33 E19 3.2 62 18 0.33/0.64 E20 3.2 72 19 0.33/0.63