COMPOSITIONS COMPRISING AT LEAST ONE POLYMER AND AT LEAST ONE METAL COMPLEX AND TO ELECTROLUMINESCENT DEVICES CONTAINING SAID COMPOSITIONS

Abstract

The present invention relates to compositions comprising at least one polymer which contains triarylamine repeating units, and at least one metal complex, to methods for the production thereof, and the use thereof in electronic devices, especially in organic electroluminescent devices, so-called OLEDs (OLED=Organic Light Emitting Diode). The present invention also relates to organic electroluminescent devices which contain said compositions

Claims

1-33. (canceled)

34. A composition comprising at least one polymer and at least one metal complex, wherein the polymer comprises at least one structural unit of formula (I): ##STR00129## wherein Ar.sup.1, Ar.sup.2 and Ar.sup.3 are the same or different in each instance and are a mono- or polycyclic, aromatic or heteroaromatic ring system optionally substituted by one or more R radicals; R is the same or different in each instance and is H, D, F, Cl, Br, I, N(R.sup.1).sub.2, CN, NO.sub.2, Si(R.sup.1).sub.3, B(OR.sup.1).sub.2, C(═O)R.sup.1, P(═O)(R.sup.1).sub.2, S(═O)R.sup.1, S(═O).sub.2R.sup.1, OSO.sub.2R.sup.1, a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 carbon atoms, each of which is optionally substituted by one or more R.sup.1 radicals, wherein one or more nonadjacent CH.sub.2 groups are optionally replaced by R.sup.1C═CR.sup.1, CRC, Si(R.sup.1).sub.2, C═O, C═S, C═NR.sup.1, P(═O)(R.sup.1), SO, SO.sub.2, NR.sup.1, O, S, or CONR.sup.1 and wherein one or more hydrogen atoms are optionally replaced by D, F, Cl, Br, I, or CN, an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and is optionally substituted in each case by one or more R.sup.1 radicals, an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and is optionally substituted by one or more R.sup.1 radicals, an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and is optionally substituted by one or more R.sup.1 radicals, or a diarylamino group, diheteroarylamino group, or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and is optionally substituted by one or more R.sup.1 radicals; an wherein two or more R radicals together optionally define a mono- or polycyclic, aliphatic, aromatic and/or benzofused ring system; R.sup.1 is the same or different in each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, wherein one or more hydrogen atoms are optionally replaced by F; and wherein two or more R.sup.1 substituents together optionally define a mono- or polycyclic, aliphatic or aromatic ring system; and the dotted lines denote bonds to adjacent structural units in the polymer; the metal complex comprises a metal atom of groups 13 to 15 and a ligand of structure (L-I): ##STR00130## wherein R.sup.11 and R.sup.12 may independently be oxygen, sulfur, selenium, NH, or NR.sup.14, wherein R.sup.14 is selected from the group comprising alkyl or aryl and may be bonded to R.sup.13; and R.sup.13 is a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which are optionally substituted by one or more R.sup.1 radicals, wherein one or more nonadjacent CH.sub.2 groups are optionally replaced by R.sup.1C═CR.sup.1, C≡C, Si(R.sup.1).sub.2, C═O, C═S, C═NR.sup.1, P(═O)(R.sup.1), SO, SO.sub.2, NR.sup.1, O, S, or CONR.sup.1 and wherein one or more hydrogen atoms are optionally replaced by D, F, Cl, Br, I, or CN, an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and are optionally substituted in each case by one or more R.sup.1 radicals, an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and is optionally substituted by one or more R.sup.1 radicals, an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and is optionally substituted by one or more R.sup.1 radicals, or a diarylamino group, diheteroarylamino group, or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and is optionally substituted by one or more R.sup.1 radicals; and wherein the R.sup.13 radical optionally defines a ring system with one or both of the R.sup.11 and R.sup.12 radicals.

35. The composition of claim 34, wherein the Ar.sup.3 radical of formula (I) is substituted by Ar.sup.4 in at least one ortho position based on the position of the nitrogen atom shown in formula (I), wherein Ar.sup.4 is a mono- or polycyclic, aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and is optionally substituted by one or more R radicals.

36. The composition of claim 35, wherein the polymer comprises at least one structural unit of formula (I) selected from the structural unit of formula (Ia): ##STR00131## wherein q is 0, 1, 2, 3, 4, 5, or 6; X is CR.sub.2, NR, SiR.sub.2, O, S, C═O or P═O; and r is 0 or 1.

37. The composition of claim 35, wherein Ar.sup.3 is substituted by Ar.sup.4 in one of the two ortho positions, and Ar.sup.3 is additionally joined to Ar.sup.4 in the meta position adjacent to the substituted ortho position.

38. The composition of claim 35, wherein the polymer comprises at least one structural unit of formula (I) selected from the structural unit of formula (Ib): ##STR00132## wherein X is CR.sub.2, NR, SiR.sub.2, O, S, C═O, or P═O; m is 0, 1, 2, 3 or 4; n is 0, 1, 2, or 3; and s and t are each 0 or 1, wherein the sum of (s+t)=1 or 2.

39. The composition of claim 35, wherein the at least one structural unit of formula (I) is selected from structural units of formulae (II), (III), and (IV): ##STR00133## wherein X is CR.sub.2, NR, SiR.sub.2, O, S, C═O, or P═O; m is 0, 1, 2, 3 or 4; n is 0, 1, 2, or 3.

40. The composition of claim 39, wherein the at least one structural unit of formula (II) is selected from the structural unit of formula (V): ##STR00134## wherein p is 0, 1, 2, 3, 4, or 5.

41. The composition of claim 39, wherein the at least one structural unit of formula (III) is selected from the structural unit of the following formula (VI): ##STR00135##

42. The composition of claim 39, wherein the at least one structural unit of formula (IV) is selected from the structural unit of formula (VII): ##STR00136##

43. The composition of claim 34, wherein the polymer comprises at least one structural unit of formula (I) selected from the structural unit of formula (VIIIa): ##STR00137## or the structural unit of formula (VIIIb): ##STR00138## wherein w is 1, 2, or 3; Ar.sup.5 to Ar.sup.9 are each the same or different at each instance and are a mono- or polycyclic, aromatic or heteroaromatic ring system optionally substituted by one or more R radicals; and the dotted lines denote bonds to adjacent structural units in the polymer.

44. The composition of claim 43, wherein at least one of the Ar.sup.5 and/or Ar.sup.8 radicals of formulae (VIIIa) and/or (VIIIb) is substituted by Ar.sup.4 in at least one ortho position, based on the position of the nitrogen atom shown in formula (VIIIa) and/or (VIIIb), where Ar.sup.4 is a mono- or polycyclic, aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and is optionally substituted by one or more R radicals.

45. The composition of claim 43, wherein the at least one structural unit of formula (VIIIa) is selected from the structural units of formulae (VIIIa-1a), (VIIIa-1b), (VIIIa-1c), and (VIIIa-1d): ##STR00139## wherein Ar.sup.4 is a mono- or polycyclic, aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and is optionally substituted by one or more R radicals; X is CR.sub.2, NR, SiR.sub.2, O, S, C═O, or P═O; m is 0, 1, 2, 3 or 4; n is 0, 1, 2, or 3; r is 0 or 1; and s and t are each 0 or 1, wherein the sum of (s+t)=1 or 2.

46. The composition of claim 43, wherein the at least one structural unit of formula (VIIIa) is selected from structural units of formulae (IX), (X), (XI), (XII), (XIII), (XIV), (XV), and (XVI): ##STR00140## wherein Ar.sup.4 is a mono- or polycyclic, aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and is optionally substituted by one or more R radicals; X is CR.sub.2, NR, SiR.sub.2, O, S, C═O, or P═O; m is 0, 1, 2, 3 or 4; n is 0, 1, 2, or 3; and p is 0, 1, 2, 3, 4, or 5.

47. The composition of claim 34, wherein at least one of the structural units of formulae (I) comprises at least one crosslinkable Q group.

48. The composition of claim 34, wherein the mono- or polycyclic, aromatic or heteroaromatic Ar.sup.a groups are selected from: ##STR00141## ##STR00142## wherein X is CR.sub.2, NR, SiR.sub.2, O, S, C═O, or P═O; the dotted lines denote bonds to adjacent structural units in the polymer; m is 0, 1, 2, 3, or 4; n is 0, 1, 2, or 3; o is 0, 1, or 2; and p is 0, 1, 2, 3, 4, or 5.

49. The composition of claim 34, wherein the mono- or polycyclic, aromatic or heteroaromatic Ar.sup.1 and Ar.sup.2 groups are selected from: ##STR00143## ##STR00144## ##STR00145## wherein X is CR.sub.2, NR, SiR.sub.2, O, S, C═O, or P═O; Y is CR.sub.2, SiR.sub.2, O, S, or a straight-chain or branched alkyl group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms, each of which is optionally substituted by one or more R.sup.1 radicals, and wherein one or more nonadjacent CH.sub.2 groups, CH groups, or carbon atoms in the alkyl, alkenyl, or alkynyl groups is optionally replaced by Si(R.sup.1).sub.2, C═O, C═S, C═NR.sup.1, P(═O)(R.sup.1), SO, SO.sub.2, NR.sup.1, O, S, CONR.sup.1, an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and is optionally substituted in each case by one or more R.sup.1 radicals, an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and is optionally substituted by one or more R.sup.1 radicals, an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and is optionally substituted by one or more R.sup.1 radicals, or a diarylamino group, diheteroarylamino group, or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and is optionally substituted by one or more R.sup.1 radicals; the dotted lines represent bonds to adjacent structural units in the polymer; k is 0 or 1; m is 0, 1, 2, 3 or 4; n is 0, 1, 2 or 3; o is 0, 1 or 2; and q is 0, 1, 2, 3, 4, 5 or 6.

50. The composition of claim 47, wherein the crosslinkable Q group is selected from the group consisting of (1) terminal or cyclic alkenyl or terminal dienyl and alkynyl groups, (2) alkenyloxy, dienyloxy, or alkynyloxy groups, (3) acrylic acid groups, (4) oxetane and oxirane groups, (5) silane groups, and (6) cyclobutane groups.

51. The composition of claim 50, wherein the crosslinkable Q group is selected from: ##STR00146## ##STR00147## wherein the R.sup.110, R.sup.120 and R.sup.130 radicals in the formulae Q1 to Q8, Q11, Q13 to Q20 and Q23 are the same or different at each instance and are H or a straight-chain or branched alkyl group having 1 to 6 carbon atoms; Ar.sup.10 in the formulae Q13 to Q 24 is a mono- or polycyclic, aromatic or heteroaromatic ring system which is optionally substituted by one or more R radicals; g is an integer from 0 to 8; h is an integer from 1 to 8; and the dotted bond in the formulae Q1 to Q11 and Q13 to Q23 and the dotted bonds in the formulae Q12 and Q24 denote the linkage of the crosslinkable group to one of the mono- or polycyclic, aromatic or heteroaromatic ring systems Ar.sup.1 to Ar.sup.3.

52. The composition of claim 34, wherein the proportion of structural units of formulae (I) in the polymer is in the range from 1 to 100 mol %, based on 100 mol % of all copolymerized monomers present as structural units in the polymer.

53. The composition of claim 34, wherein the polymer, as well as structural units of the formulae (I), comprises at least one further structural unit of formula (XIX) other than the structural units of formulae (I):
—Ar.sup.11—  (XII) wherein Ar.sup.11 is a mono- or polycyclic, aromatic or heteroaromatic ring system optionally substituted by one or more R radicals.

54. The composition of claim 47, wherein the proportion of structural units of the formula (I) having a crosslinkable Q group in the polymer is in the range from 0.1 to 50 mol %, based on 100 mol % of all copolymerized monomers present as structural units in the polymer.

55. The composition of claim 34, wherein the R.sup.13 radical in formula (L-I) is selected from the group comprising alkyl, long-chain alkyl, alkoxy, long-chain alkoxy, cycloalkyl, haloalkyl, aryl, arylene, halogenaryl, heteroaryl, heteroarylene, heterocycloalkylene, heterocycloalkyl, haloheteroaryl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, ketoaryl, haloketoaryl, ketoheteroaryl, ketoalkyl, haloketoalkyl, ketoalkenyl, haloketoalkenyl, wherein, in the case of suitable radicals, one or more nonadjacent CH.sub.2 groups independently are optionally replaced by —O—, —S—, —NH—, —NR—, —SiR.sub.2—, —CO—, —COO—, —OCO—, —OCO—O—, —SO.sub.2—, —S—CO—, —CO—S—, —CR═CR— or —C≡C—, in such a way that oxygen and/or sulfur atoms are not bonded directly to one another, and are likewise optionally replaced by aryl or heteroaryl, wherein terminal CH.sub.3 groups are regarded as CH.sub.2 groups in the sense of CH.sub.2—H.

56. The composition of claim 34, wherein the metal atom of the metal complex is selected from the group comprising bismuth, tin, and mixtures thereof.

57. The composition of claim 34, wherein the metal complex has the structure ML.sub.m where M is a metal atom, L is a ligand, and m is an integer from 1 to 10 and, if m is greater than 1, all L are independent of one another.

58. The composition of claim 34, wherein the R.sup.13 radical has at least one substituent selected from halogen, pseudohalogen, —CN, and —NO.sub.2.

59. The composition of claim 34, wherein the R.sup.13 radical corresponds to one of the formulae (R.sup.13-I), (R.sup.13-II), and (R.sup.13-III): ##STR00148## wherein the Y.sup.1 to Y.sup.7 groups are each independently selected from the group comprising C—F, C—CF.sub.3, C—CN, C-halogen, C-pseudohalogen, and N.

60. The composition of claim 34, wherein the metal complex comprises a ligand L selected from the group of the unsubstituted, partly fluorinated, and perfluorinated organic carboxylic acids.

61. The composition of claim 34, wherein the weight ratio of polymer to metal complex is in the range from 1000:1 to 1:2.

62. A process for producing a composition according claim 34, wherein a polymer having structural units of formula (I) is contacted with a metal complex comprising a metal atom of groups 13 to 15 and a ligand of the structure (L-I).

63. A solution or formulation comprising at least one composition according to claim 34 in one or more solvents.

64. An electronic or optoelectronic component comprising one or more active layers, wherein at least one of the one or more active layers comprises one or more compositions according to claim 34.

65. The electronic or optoelectronic component of claim 64, wherein the electronic or optoelectronic component is selected from the group consisting of organic electroluminescent devices, organic light-emitting electrochemical cells, organic field-effect transistors, organic integrated circuits, organic thin-film transistors, organic solar cells, organic laser diodes, organic photovoltaic elements, organic photovoltaic devices, and organic photoreceptors.

66. The electronic or optoelectronic component of claim 65, wherein the active layer comprising one or more compositions.

Description

WORKING EXAMPLES

Part A: Synthesis of the Monomers

[0257] The monomers for production of the polymers of the inventive compositions are already described in the prior art, are commercially available or are prepared according to a literature method, and are summarized in the following table:

TABLE-US-00011 Monomer Structure Synthesis according to M1 [00111] WO 2010/097155 A1 M2 [00112] WO 99/048160 A1 M3 [00113] Macromolecules 2000, 33, 2016-2020 M4 [00114] WO 2013/156130 M5 [00115] WO 2013/156130 M6 [00116] WO 2013/156130 M7 [00117] WO 2013/156130 (analogously to Mo14) M8 [00118] J. Mater. Chem., 2012, 22, 7945-7953 M9 [00119] Chem. Eur. J. 2006, 12, 4351-4361

Part B: Synthesis of the Polymers

[0258] The comparative polymer V1 and the inventive polymers P1 to P8 are prepared by SUZUKI coupling by the process described in WO 2010/097155 from the monomers disclosed in Part A.

[0259] The polymers V1 and P1 to P8 prepared in this way contain the structural units, after elimination of the leaving groups, in the percentages reported in Table B1 (percentages=mol %). In the case of the polymers which are prepared from monomers having aldehyde groups, the latter are converted to crosslinkable vinyl groups after the polymerization by WITTIG reaction by the process described in WO 2010/097155. The polymers listed correspondingly in Table B1 and used in Part C thus have crosslinkable vinyl groups rather than the aldehyde groups originally present.

[0260] The palladium and bromine contents of the polymers are determined by ICP-MS. The values determined are below 10 ppm.

[0261] The molecular weights Mw and the polydispersities D are determined by means of gel permeation chromatography (GPC) (model: Agilent HPLC System Series 1100, column: PL-RapidH from Polymer Laboratories; solvent: THF with 0.12% by volume of o-dichlorobenzene; detection: UV and refractive index; temperature: 40° C.). Calibration is effected with polystyrene standards.

[0262] The results are collated in Table B1.

TABLE-US-00012 TABLE B1 Molecular weight Polymers Monomers M.sub.w (g/mol) Polydispersity V1 M8 50% M9 50% 315 000 2.8 P1 M4 50% M3 50% 339 000 3.1 P2 M4 40% M3 50% M1 10% 328 000 2.9 P3 M4 50% M6 50% 275 000 3.2 P4 M4 40% M6 50% M1 10% 123 000 3.3 P5 M4 40% M3 50% M5 10% 300 000 2.7 P6 M4 40% M7 50% M1 10% 100 000 4.5 P7 M2 50% M3 50% 438 000 3.3 P8 M2 40% M1 10% M3 50% 417 000 3.1

Part C: Dopants

[0263] The dopant for production of the inventive compositions is already described in the prior art and is prepared according to a literature method.

TABLE-US-00013 Dopant Structure Synthesis according to D1 [00120] WO 2013/182389

Part D: Device Examples

[0264] The inventive composition, composed of polymer and metal complex, can be processed from solution and leads, compared to vacuum-processed OLEDs, to much more easily producible OLEDs having properties that are nevertheless good.

[0265] Whether the crosslinkable variants of the inventive compositions (comprising crosslinkable polymers) after crosslinking give rise to a completely insoluble layer is tested analogously to WO 2010/097155.

[0266] Table D1 lists the remaining layer thickness of the original 20 nm after the washing operation described in WO 2010/097155. If there is no decrease in the layer thickness, the composition of polymer and metal complex is insoluble and hence the crosslinking is sufficient.

TABLE-US-00014 TABLE D1 Check of the residual layer thickness of the original 20 nm after the wash test Mass ratio of Residual layer thickness after wash Metal polymer:metal test (in nm) Polymer complex complex Crosslinking at 220° C. V1 D1 85:15 3.5 P2 D1 85:15 20 P4 D1 85:15 20 P6 D1 85:15 20 P8 D1 85:15 20

[0267] As can be inferred from Table D1, the composition comprising comparative polymer V1 which does not bear any crosslinking group hardly crosslinks at all at 220° C. The mixtures with the inventive polymers P2, P4, P6 and P8 crosslink completely at 220° C.

[0268] There are already many descriptions of the production of such solution-based OLEDs in the literature, for example in WO 2004/037887 and WO 2010/097155. The process is matched to the circumstances described hereinafter (variation in layer thickness, materials).

[0269] The inventive polymers are used in three different layer sequences:

[0270] Structure A is as follows: [0271] substrate, [0272] ITO (50 nm), [0273] hole injection layer (HIL) (200 nm), [0274] cathode.

[0275] Structure B is as follows: [0276] substrate, [0277] ITO (50 nm), [0278] HIL (20 nm), [0279] hole transport layer (HTL) (40 nm), [0280] emission layer (EML) (30 nm), [0281] electron transport layer (ETL) (20 nm), [0282] cathode.

[0283] Structure C is as follows: [0284] substrate, [0285] ITO (50 nm), [0286] HIL (20 nm), [0287] HTL (20 nm), [0288] EML (60 nm), [0289] hole blocker layer (HBL) (10 nm), [0290] ETL (40 nm), [0291] cathode.

[0292] Substrates used are glass plates coated with structured ITO (indium tin oxide) of thickness 50 nm. The hole injection, hole transport and emission layers are applied to these coated glass plates.

[0293] The hole injection layers used are the inventive compositions, composed of polymer and metal complex, and comparative mixtures, each dissolved in the solvent mixture anisole:xylene (2:1). The typical solids content of such solutions is about 8 to 35 g/l when layer thicknesses between 20 nm and 200 nm are to be achieved by means of spin-coating. The layers are spun on in an inert gas atmosphere, argon in the present case, and baked at 180° C. or 220° C. for 60 minutes.

[0294] The hole transport layers in structure C are processed from toluene. The typical solids content of such solutions is about 5 g/l when layer thicknesses of 20 nm are to be achieved by means of spin-coating. The layers are spun on in an inert gas atmosphere, argon in the present case, and baked at 180° C. or 220° C. for 60 minutes.

[0295] In structure B, the hole transport layer is formed by thermal evaporation in a vacuum chamber. The materials used in the present case are shown in Table D2.

TABLE-US-00015 TABLE D2 Structural formulae of the in the hole-transporting materials processed from vacuum [00121] HT1

[0296] The emission layer is always composed of at least one matrix material (host material) and an emitting dopant (emitter). In addition, compositions composed of a plurality of matrix materials and co-dopants may occur. Details given in such a form as H1 (92%):dopant (8%) mean here that the material H1 is present in the emission layer in a proportion by weight of 92% and the dopant in a proportion by weight of 8%. The mixture for the emission layer is dissolved in toluene for structure C. The typical solids content of such solutions is about 18 g/l when, as here, the layer thickness of 60 nm which is typical of a device is to be achieved by means of spin-coating. The layers are spun on in an inert gas atmosphere, argon in the present case, and baked at 180° C. for 10 minutes. In structure B, the emission layer is formed by thermal evaporation in a vacuum chamber. This layer may consist of more than one material, the materials being added to one another by co-evaporation in a particular proportion by volume. Details given in such a form as H3:dopant (95%:5%) mean here that the H3 and dopant materials are present in the layer in a proportion by volume of 95%:5%.

[0297] The materials used in the present case are shown in Table D3.

TABLE-US-00016 TABLE D3 Structural formulae of the materials used in the emission layer [00122] M1 [00123] M2 [00124] M3 [00125] TEG [00126] SEB

[0298] The materials for the hole blocker layer and electron transport layer are likewise applied by thermal vapour deposition in a vacuum chamber and are shown in Table D4. The hole blocker layer consists of ETM1. The electron transport layer consists of the two materials ETM1 and ETM2, which are added to one another by co-evaporation in a proportion by volume of 50% each.

TABLE-US-00017 TABLE D4 HBL and ETL materials used [00127] ETM1 [00128] ETM2

[0299] The cathode is formed by the thermal evaporation of an aluminium layer of thickness 100 nm.

[0300] The exact structure of the OLEDs can be found in Table D5. The HTL column lists the polymer used, and the temperature at which the layer is baked and optionally crosslinked.

TABLE-US-00018 TABLE D5 Structure of the OLEDs HIL Mass ratio of HTL Metal polymer:metal T T EML Example Structure Polymer complex complex [° C.] Polymer [° C.] Composition D1 B P7 D1 85:15 180 — — M3 95%; SEB 5% D2 C P8 D1 85:15 180 P2 180 M1 30%; M2 55%; TEG 15% D3 A P1 — — 180 — — — D4 A P1 D1 85:15 180 — — — D5 A P3 — — 180 — — — D6 A P3 D1 85:15 180 — — — D7 B P3 D1 85:15 180 — — M3 95%; SEB 5% D8 B P1 D1 85:15 180 — — M3 95%; SEB 5% D9 C P2 D1 85:15 180 P2 180 M1 30%; M2 55%; TEG 15% D10 C P4 D1 85:15 220 P2 180 M1 30%; M2 55%; TEG 15% D11 B V1 D1 85:15 180 — — M3 95%; SEB 5%

[0301] The OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectra, current-voltage-luminance characteristics (IUL characteristics) assuming Lambertian radiation characteristics and, in the case of structures B and C, the (operating) lifetime are determined. The IUL characteristics are used to determine parameters such as the operating voltage (in V) and the external quantum efficiency (in %) at a particular brightness. LD80 @ 1000 cd/m.sup.2 is the lifetime until the OLED, given a starting brightness of 1000 cd/m.sup.2, has dropped to 80% of the starting intensity, i.e. to 800 cd/m.sup.2.

[0302] The properties of the different OLEDs are summarized in Tables D6 a and b. Examples D11 and D12 are comparative examples; all the other examples show properties of inventive OLEDs.

Tables D6a and D6b:

Properties of the OLEDs

[0303]

TABLE-US-00019 TABLE D6a Voltage at 1 mA/cm.sup.2 Example [V] D3 6 D4 1.2 D5 3.2 D6 0.4

TABLE-US-00020 TABLE D6b Efficiency at Voltage at LD80 at 1000 cd/m.sup.2 1000 cd/m.sup.2 1000 cd/m.sup.2 Example % EQE [V] [h] D1 8.1 4.4 205 D2 16.5 4.9 195 D7 7.9 4.5 266 D8 8.2 4.3 305 D9 16.5 4.9 215 D10 16.3 4.5 240 D11 8.1 4.4 108

[0304] Table D6 a shows that the voltages of components made from inventive mixtures (polymer and metal complex) are significantly lower than their equivalents without metal complex. The inventive mixtures are thus suitable as hole injection materials which lower the operating voltage of the OLED.

[0305] Table D6 b shows that the use of the inventive mixtures leads to an improvement in lifetime over the prior art.