MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES

Abstract

The present invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescent devices, and to organic electroluminescent devices which comprise these compounds.

Claims

1.-21. (canceled)

22. A compound of formula (1), ##STR00103## where the following applies to the symbols and indices used: G is a group of formula (G-1), ##STR00104## where the dashed bond indicates the bonding to Ar.sup.S or, if Ar.sup.S is absent, to the central benzene of the anthracene as depicted in formula (1); R.sup.1, R.sup.2 stand, on each occurrence, identically or differently, for an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may in each case also be substituted by one or more radicals R; R.sup.3, R.sup.4, R.sup.5 stand, on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, N(Ar).sub.2, C(═O)Ar, P(═O)(Ar).sub.2, S(═O)Ar, S(═O).sub.2Ar, NO.sub.2, Si(R).sub.3, B(OR).sub.2, OSO.sub.2R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non-adjacent CH.sub.2 groups may be replaced by RC═CR, C≡C, Si(R).sub.2, Ge(R).sub.2, Sn(R).sub.2, C═O, C═S, C═Se, P(═O)(R), SO, SO.sub.2, O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms, which may be substituted by one or more R radicals; where two adjacent radicals selected from R.sup.3, R.sup.4, R.sup.5 may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R; R.sup.A stands, on each occurrence, identically or differently, for F, CN, N(Ar.sup.N).sub.2, C(═O)Ar, P(═O)(Ar).sub.2, S(═O)Ar, S(═O).sub.2Ar, Si(R).sub.3, B(OR).sub.2, OSO.sub.2R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non-adjacent CH.sub.2 groups may be replaced by RC═CR, C≡C, Si(R).sub.2, Ge(R).sub.2, Sn(R).sub.2, C═O, C═S, C═Se, P(═O)(R), SO, SO.sub.2, O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms, which may be substituted by one or more R radicals; Ar.sup.N stands, on each occurrence, identically or differently, for an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case also be substituted by one or more radicals R, and wherein two groups Ar.sup.N may be connected with one another by a single bond or by a divalent bridge selected from N(R), O, S, C(R).sub.2, C(R).sub.2—C(R).sub.2, Si(R).sub.2 or B(R); Ar.sup.S stands, on each occurrence, identically or differently, for a single bond or for an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case also be substituted by one or more radicals R; R stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, N(Ar).sub.2, C(═O)Ar, P(═O)(Ar).sub.2, S(═O)Ar, S(═O).sub.2Ar, NO.sub.2, Si(R′).sub.3, B(OR′).sub.2, OSO.sub.2R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R′, where in each case one or more non-adjacent CH.sub.2 groups may be replaced by R′C═CR′, C≡C, Si(R′).sub.2, Ge(R′).sub.2, Sn(R′).sub.2, C═O, C═S, C═Se, P(═O)(R′), SO, SO.sub.2, O, S or CONR′ and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R′, or an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R′, where two adjacent radicals R may form a mono- or polycyclic, aliphatic ring system or aromatic ring system, which may be substituted by one or more radicals R′; Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may in each case also be substituted by one or more radicals R′; R′ stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, where in each case one or more non-adjacent CH.sub.2 groups may be replaced by SO, SO.sub.2, O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 24 C atoms; and n, m, p, q are, identically or differently, 0,1 or 2.

23. The compound according to claim 22, wherein R.sup.3, R.sup.4, R.sup.5 stand, on each occurrence, identically or differently, for a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non-adjacent CH.sub.2 groups may be replaced by RC═CR, C≡C, Si(R).sub.2, Ge(R).sub.2, Sn(R).sub.2, C═O, C═S, C═Se, P(═O)(R), SO, SO.sub.2, O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R, an aryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms, which may be substituted by one or more R radicals.

24. The compound according to claim 22, wherein R.sup.3, R.sup.4, R.sup.5 stand, on each occurrence, identically or differently, for a straight-chain alkyl or alkoxy group having 1 to 10 C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non-adjacent CH.sub.2 groups may be replaced by RC═CR, C≡C, Si(R).sub.2, Ge(R).sub.2, Sn(R).sub.2, C═O, C═S, C═Se, P(═O)(R), SO, SO.sub.2, O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R, an aryloxy group having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms, which may be substituted by one or more R radicals.

25. The compound according to claim 22, wherein R.sup.3, R.sup.4, R.sup.5 stand, on each occurrence, identically or differently, for an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may in each case also be substituted by one or more radicals R

26. The compound according to claim 22, wherein the group G stands for a group of formula (G-2), (G-3) or (G-4), ##STR00105## where R.sup.1 and R.sup.2 have the same definition as in claim 22; and R.sup.3, R.sup.4, R.sup.5 stand on each occurrence, identically or differently for a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non-adjacent CH.sup.2 groups may be replaced by RC═CR, C≡C, Si(R).sup.2, Ge(R).sup.2, Sn(R).sup.2, C═O, C═S, C═Se, P(═O)(R), SO, SO.sub.2, O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms, which may be substituted by one or more R radicals.

27. The compound according to claim 22, wherein R.sup.A stands, on each occurrence, identically or differently, for F, CN, N(Ar.sup.N).sub.2, C(═O)Ar, P(═O)(Ar).sub.2, S(═O)Ar, S(═O).sub.2Ar, Si(R).sub.3, B(OR).sub.2, OSO.sub.2R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non-adjacent CH.sub.2 groups may be replaced by RC═CR, C≡C, Si(R).sub.2, Ge(R).sub.2, Sn(R).sub.2, C═O, C═S, C═Se, P(═O)(R), SO, SO.sub.2, O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms, which may be substituted by one or more R radicals.

28. The compound according to claim 22, wherein R.sup.A is selected on each occurrence, identically or differently, from N(Ar.sup.N).sub.2; where Ar.sup.N has the same definition as in claim 22; from branched or cyclic alkyl groups represented by the general following formula (RS-a) ##STR00106## wherein R.sup.22, R.sup.23, R.sup.24 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R.sup.25, and where two of radicals R.sup.22, R.sup.23, R.sup.24 or all radicals R.sup.22, R.sup.23, R.sup.24 may be joined to form a (poly)cyclic alkyl group, which may be substituted by one or more radicals R.sup.25; R.sup.25 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms; with the proviso that at each occurrence at least one of radicals R.sup.22, R.sup.23 and R.sup.24 is other than H, with the proviso that at each occurrence all of radicals R.sup.22, R.sup.23 and R.sup.24 together have at least 4 carbon atoms and with the proviso that at each occurrence, if two of radicals R.sup.22, R.sup.23, R.sup.24 are H, the remaining radical is not a straight-chain; or from branched or cyclic alkoxy groups represented by the general following formula (RS-b) ##STR00107## wherein R.sup.26, R.sup.27, R.sup.28 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R.sup.25 as defined above, and where two of radicals R.sup.26, R.sup.27, R.sup.28 or all radicals R.sup.26, R.sup.27, R.sup.28 may be joined to form a (poly)cyclic alkyl group, which may be substituted by one or more radicals R.sup.25 as defined above; with the proviso that at each occurrence only one of radicals R.sup.26, R.sup.27 and R.sup.28 may be H; or from aralkyl groups represented by the general following formula (RS-c) ##STR00108## wherein R.sup.29, R.sup.30, R.sup.31 are at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R.sup.32, or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.32, and where two or all of radicals R.sup.29, R.sup.30, R.sup.31 may be joined to form a (poly)cyclic alkyl group or an aromatic ring system, each of which may be substituted by one or more radicals R.sup.32; R.sup.32 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms; with the proviso that at each occurrence at least one of radicals R.sup.29, R.sup.30 and R.sup.31 is other than H and that at each occurrence at least one of radicals R.sup.29, R.sup.30 and R.sup.31 is or contains an aromatic ring system having at least 6 aromatic ring atoms; or from aromatic ring systems represented by the general following formula (RS-d) ##STR00109## wherein R.sup.40 to R.sup.44 is at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R.sup.32, or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.32, and where two or more of radicals R.sup.40 to R.sup.44 may be joined to form a (poly)cyclic alkyl group or an aromatic ring system, each of which may be substituted by one or more radicals R.sup.32 as defined above.

29. The compound according to claim 22, wherein Ar.sup.S stands for benzene, biphenyl, terphenyl, naphthalene, fluorene, indenofluorene, spirobifluorene, triazine, benzoquinoline, benzoquinazoline, dibenzofuran, dibenzothiophene, or carbazole, each each optionally substituted by one or more radicals R.

30. The compound according to claim 22, wherein m=n=0.

31. The compound according to claim 22, wherein p=q=0.

32. The compound according to claim 22, wherein the compound is selected from compounds of formula (2), (3) or (4), ##STR00110## where R.sup.3, R.sup.4, R.sup.5 stand on each occurrence, identically or differently for a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non-adjacent CH.sup.2 groups may be replaced by RC═CR, C≡C, Si(R).sup.2, Ge(R).sup.2, Sn(R).sup.2, C═O, C═S, C═Se, P(═O)(R), SO, SO.sub.2, O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms, which may be substituted by one or more R radicals; and where the other symbols and indices have the same meaning as in claim 22.

33. The compound according to claim 22, wherein the compound is selected from compounds of formulae (2-1a) to (2-4a), (4-1a) to (4-3a), ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## where R.sup.3, R.sup.4, R.sup.5 stand on each occurrence, identically or differently for a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non-adjacent CH.sup.2 groups may be replaced by RC═CR, C≡C, Si(R).sup.2, Ge(R).sup.2, Sn(R).sup.2, C═O, C═S, C═Se, P(═O)(R), SO, SO.sub.2, O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms, which may be substituted by one or more R radicals; R.sup.40 to R.sup.44 are on each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R.sup.32, or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.32; R.sup.32 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms; with the proviso that at each occurrence at least one of radicals R.sup.29, R.sup.30 and R.sup.31 is other than H and that at each occurrence at least one of radicals R.sup.29, R.sup.30 and R.sup.31 is or contains an aromatic ring system having at least 6 aromatic ring atoms; or from aromatic ring systems represented by the general following formula (RS-d) ##STR00119## wherein R.sup.40 to R.sup.44 is at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R.sup.32, or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.32, and where two or more of radicals R.sup.40 to R.sup.44 may be joined to form a (poly)cyclic alkyl group or an aromatic ring system, each of which may be substituted by one or more radicals R.sup.32 as defined above, and where R.sup.1, R.sup.2, R, m, n, p and q have the same definition than in claim 22.

34. The compound according to claim 32, wherein R.sup.40 to R.sup.44 are at each occurrence, identically or differently, selected from an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.32; wherein R.sup.32 is at each occurrence, identically or differently, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms; with the proviso that at each occurrence at least one of radicals R.sup.29, R.sup.30 and R.sup.31 is other than H and that at each occurrence at least one of radicals R.sup.29, R.sup.30 and R.sup.31 is or contains an aromatic ring system having at least 6 aromatic ring atoms; or from aromatic ring systems represented by the general following formula (RS-d) ##STR00120## wherein R.sup.40 to R.sup.44 is at each occurrence, identically or differently, selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more radicals R.sup.32, or an aromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R.sup.32, and where two or more of radicals R.sup.40 to R.sup.44 may be joined to form a (poly)cyclic alkyl group or an aromatic ring system, each of which may be substituted by one or more radicals R.sup.32 as defined above.

35. The compound according to claim 32, wherein the compound is selected from compounds of formulae (2-1-a′) to (4-5-a′), ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127## ##STR00128## where the symbols and indices have the same meaning as in claim 32.

36. The compound according to claim 22, wherein the compound is selected from compounds of formulae (2-b) to (4-b), ##STR00129## where the symbols and indices have the same meaning as in claim 22.

37. A polymer, oligomer or dendrimer containing one or more compounds according to claim 22, where the bond(s) to the polymer, oligomer or dendrimer may be localised at any positions in formula (1) which is substituted by R.sup.1 to R.sup.5 or R.sup.A.

38. A formulation comprising at least one compound according to claim 22 and at least one solvent.

39. An organic electroluminescent device comprising an anode, a cathode and at least one organic layer comprising at least one compound according to claim 22, wherein the compound is employed as an emitter in an emitting layer.

40. The organic electroluminescent device according to claim 39, wherein the compound is employed as a fluorescent emitter in an emitting layer, wherein the emitting layer comprises at least one further component selected from matrix materials.

41. The organic electroluminescent device according to claim 39, wherein the compound is employed as a fluorescent emitter in an emitting layer, wherein the emitting layer comprises at least one sensitizer compound selected from compounds that exhibit delayed fluorescence and from phosphorescent compounds.

42. The organic electroluminescent device according to claim 41, wherein the emitting layer further comprises at least one organic functional material selected from matrix materials.

Description

A) SYNTHESIS EXAMPLES

Example A-1: 2,6,9,10-tetrakis(2,3,4,5,6-pentakis-phenylphenyl)-anthracene (1)

a) 2,6-Dibromo-9,10-bis(2-phenylethinyl)anthracene (2)

[0190] ##STR00089##

[0191] A solution of phenylacetylene (4.2 g, 4.5 mL, 41.0 mmol, 3.0 equiv.) in THF (200 mL) is placed in a three-necked flask equipped with a magnetic stirring bar under argon atmosphere. The reaction mixture is degassed with argon for 20 min before it is cooled down to −78° C. The reaction mixture is then stirred for 10 min, before n-BuLi (2.5 M in hexane, 16.4 mL, 40.0 mmol, 2.9 equiv.) is slowly added to it. The reaction mixture is further stirred for 2 hours before 2,6-dibromo-9,10-anthracenedione (5.0 g, 13.7 mmol, 1.0 equiv.) is added to the mixture as a solid. The reaction mixture is then heated overnight at room temperature. Then, tin(II)chloride dihydrate (12.6 g, 50.0 mmol, 3.7 equiv.) is dissolved in hydrochloric acid (12%, 20 mL) and added to the mixture. The reaction mixture is heated for 1 h under reflux. The product (2) precipitates as a red solid, which is then filtered, washed with heptane and dried in vacuo (4.7 g, 8.8 mmol, 62%).

b) 2,6,9,10-Tetrakis(2-phenylethinyl)anthracene (3)

[0192] ##STR00090##

[0193] 5.00 g of 2,6-Dibromo-9,10-bis(2-phenylethinyl)anthracene (2) (9.3 mmol, 1.0 equiv.) in TEA (1000 mL) are introduced in a four-necked flask equipped with a magnetic stirring bar under argon. The reaction mixture is degassed under argon for 20 min before CuI (0.05 g, 0.3 mmol, 0.03 equiv.), Pd(PPh.sub.3).sub.2Cl.sub.2 (0.13 g, 0.2 mmol, 0.02 equiv.) and phenylacetylene (5.71 g, 6.1 mL, 55.9 mmol, 6.0 equiv.) are added. The reaction mixture is then stirred for 3 h under reflux. The reaction is cooled down to room temperature. The solvent is removed. The black residue is recovered with toluene and filtered over aluminum oxide. The solvent is removed. A red solid remains, which is recrystallized from toluene (120 mL). The desired product (3) is isolated as a red solid (2.2 g, 5.9 mmol, 41%).

c) 2,6,9,10-Tetrakis(2,3,4,5,6-pentakis-phenylphenyl)-anthracene (1)

[0194] ##STR00091##

[0195] 2,6,9,10-Tetrakis(2-phenylethinyl)anthracene (3) (24.5 g, 42.2 mmol, 1.0 equiv.) and tetraphenylcyclopenta-2,4-dienone (74.0 g, 192.5 mmol, 4.6 equiv.) are placed in a two-necked flask equipped with a magnetic stirring bar under argon. Diphenyl ether (1000 mL) is added to the reaction mixture, which is heated for 14 h under reflux. After the reaction mixture has cooled down, MeOH (5000 mL) is added. A black solid precipitates, which is filtered off. The solid is then purified by hot extraction using toluene over aluminium oxide. The solid is then recrystallized from toluene three times. The resulting solid (6.0 g, 3.0 mmol, 7%, HPLC: 99.6%) is recrystallized from THF. The product (1) is then isolated as a light yellow solid (2.0 g, 1.0 mmol, 2%, HPLC: 99.9%) and dried at 400° C. in a high vacuum.

Example A-2: 9,10-Bis(2,3,4,5,6-Pentakis-phenylphenyl)-N2,N2,N6,N6-tetraphenyl-anthracene-2,6-diamine (4)

a) N2,N2,N6,N6-Tetraphenyl-9,10-bis(2-phenylethynyl)anthracene-2,6-diamine (5)

[0196] ##STR00092##

[0197] 2,6-Dibromo-9,10-bis(2-phenylethinyl)anthracene (2) (1.35 g, 2.52 mmol, 1.0 equiv.) and of N-phenylaniline (purchased product, CAS:122-39-4) (0.94 g, 5.54 mmol, 2.2 equiv.) in dried toluene (50 mL) are placed in a four-necked flask equipped with a magnetic stirring bar under argon. The reaction mixture is degassed with argon for 20 minutes. Subsequently, sodium tert-pentoxide (0.83 g, 7.55 mmol, 3.0 equiv.), tri-tert-butylphosphine tetrafluoroborate (110 mg, 378 μmol, 0.15 equiv.) and palladium acetate (17 mg, 76 μmol, 0.03 equiv.) are added to the mixture. The reaction mixture is then gradually heated to 100° C. and stirred for 17 h at this temperature. After the reaction mixture has cooled down, an aqueous acetylcysteine solution is added and stirred for 0.5 hour, followed by the extraction with toluene. The resulting red solid is recrystallized from toluene and heptane, followed by column chromatography with DCM/heptane 1:2. The product (5) is then isolated as a red solid (1.4 g, 2.5 mmol, 78%).

b) 9,10-bis(2,3,4,5,6-Pentakis-phenylphenyl)-N2, N2, N6,N6-tetraphenyl-anthracene-2,6-diamine (4)

[0198] ##STR00093##

[0199] N2,N2,N6,N6-Tetraphenyl-9,10-bis(2-phenylethynyl)anthracene-2,6-diamine (5) (16.0 g, 22 mmol, 1.0 equiv.) and tetraphenyl-cyclopentadienone (purchased, CAS: 479-33-4) (19.37 g, 49 mmol, 2.2 equiv.) are suspended in diphenyl ether (350 mL). The suspension is degassed with argon for 20 minutes and then slowly heated to 240° C. for 100 h. The suspension is then degassed with argon. After the reaction has cooled down, methanol is added and the precipitated yellow solid is filtered off. This solid is recrystallized from toluene and anisole. The desired product (4) (13.90 g, 9.75 mmol, 43%) is then sublimed.

B) Device Examples

Example B-1: Photophysical measurements

[0200] Peak Emission Wavelength λ.sub.max

[0201] To measure the peak emission wavelength the material is dissolved in toluene at a concentration of 1 mg/100 ml. The solution is excited in a Hitachi F-4500 fluorescence spectrometer at room temperature.

[0202] The peak emission wavelength λ.sub.max is the wavelength at which the spectrum shows the first maximum starting at low wavelengths. Typically, the first maximum is also the global maximum. If the first maximum is not the global maximum, then all maxima having an intensity of at least 0.5 or higher are considered.

[0203] Photoluminescence Quantum Yield PLQY

[0204] The PLQY is determined using a Hamamatsu C9920-02 measurement system. The principle is based on the excitation of the sample with light of a defined wavelength and the measurement of the radiation absorbed and emitted. During the measurement, the sample is within an Ulbricht sphere (“integrating sphere”). The spectrum of the excitation light is approximately Gaussian with a half-height width of <10 nm. The PLQY is determined by the evaluation method customary for said measurement system. The measurement is carried out at room temperature.

[0205] To determine the PLQY of a compound, the material is dissolved in toluene. A concentration of 1 mg/100 mL is used. The solution is filled into a suitable quartz cuvette. It is insured that the solution does not come into contact with air by handling the solution and cuvette in a glove box. Measurements at excitation wavelengths of 370, 380, 390, 400, 410 and 420 nm are done. The PLQY is the mean value of the values obtained at the different wavelengths.

TABLE-US-00001 TABLE 1 Peak emission wavelength (λ.sub.max) and photoluminescence quantum yield (PLQY) λ.sub.max Compound [nm] PLQY V-01 416 0.95 A-1 435 0.98

[0206] The inventive compound A-1 shows a peak emission wavelength in the blue spectral region which is more suitable for display applications compared to the state of the art compound V-01, which is emitting in the UV region (see FIG. 1). Furthermore, A-1 shows a higher photoluminescence quantum yield of 0.98 compared to V-01 (0.95). Thus, it is better in terms of use in OLED display applications showing blue emission.

Example B-2: Organic Electroluminescent Devices

[0207] Glass substrates coated with structured ITO (50 nm, indium tin oxide) are wet-cleaned (dishwasher, Merck Extran cleaner) and then treated with UV/ozone for 15 minutes. A 20 nm thick PEDOT:PSS (HC-Starck Baytron PVPA14084) layer is then spin-coated onto the substrates. The substrates are then annealed for 10 minutes on a hot plate at 180° C. in air. Different layers as given in the examples are then coated on these substrates to form the OLEDs. The materials in these layers are thermally evaporated in a vacuum chamber.

[0208] After the production, the OLEDs are encapsulated under a nitrogen atmosphere in a glovebox for protection against oxygen and water vapor. The exact layer structure of the OLEDs can be found in the examples. The materials required for the production of the OLEDs are shown in Table 3. The emission layer(s) always consist(s) of at least one host material and an emitting material. An indication such as DPEPO(59%):TADF-01(40%):A-1(1%) means that the material DPEPO is present in a volume fraction of 59%, TADF-01 is present in a volume fraction of 40% and A-1 is present in a volume fraction of 1% in the layer. Similarly, the electron transport layer and hole injection layer consist of a mixture of two materials.

[0209] The OLEDs are characterised by standard methods. For this purpose, the electroluminescence spectra and luminance (measured in cd/m.sup.2) are recorded using a calibrated CAS140-CT spectrometer together with a TOP200 telescopic optical probe from Instrument Systems in dependence of current density and voltage (measured with a Keithley 2635B source measure unit). The external quantum efficiency (EQE, measured in percent) is calculated assuming a lambertian emission characteristics from the current/voltage/luminance characteristic. The indication U1000 indicates the voltage required for a luminance of 1000 cd/m.sup.2. EQE1000 refers to the external quantum efficiency at an operating luminance of 1000 cd/m.sup.2.

Device Examples

[0210] The following layers are thermally evaporated on top of the PEDOT:PSS layer to form the OLEDs:

[0211] HTM(95%):p-D(5%) 5 nm/HTM 30 nm/H-02 10 nm/Emission layer/H-1 10 nm/ETM(50%):LiQ(50%) 20 nm/Aluminum 100 nm.

[0212] The results for different emission layers are given in Table 2. The OLEDs show deep blue emission with CIE x/y coordinates of 0.15/0.15 (Exp 1) and 0.15/0.14 (Exp 2)

TABLE-US-00002 TABLE 2 Device Results EQE1000 U1000 Ex. Emission Layer [%] [V] 1 DPEPO(59%):TADF-01 7.2 7.6 (40%):A-1(1%) 45 nm 2 DPEPO(58%):TADF-01 7.5 7.2 (40%):A-1(2%) 45 nm

TABLE-US-00003 TABLE 3 Structures of the OLED materials [00094] HTM [00095] p-D [US2010102709A1; WO2015007729A1] [00096] ETM [00097] LiQ [00098] H-01 [00099] H-02 [00100] DPEPO [00101] TADF-01 [00102] A-1