ELECTRONIC DEVICE

Abstract

The present application relates to an electronic device, to the use thereof, and to a process for production thereof.

Claims

1.-24. (canceled)

25. An electronic device comprising a first electrode, a second electrode and, arranged in between, an emitting layer E comprising a compound of a formula (E-1) ##STR01827## for which: T is B, P, P(═O) or SiR.sup.E1; X is the same or different at each instance and is selected from O, S, NR.sup.E2 and C(R.sup.E2).sub.2, where there must be at least one X present which is selected from O, S and NR.sup.E2; C.sup.1, C.sup.2 and C.sup.3 are the same or different and are selected from ring systems which have 5 to 40 ring atoms and are substituted by R.sup.E3 radicals; R.sup.E1 is selected from H, D, F, Cl, Br, I, C(═O)R.sup.E4, CN, Si(R.sup.E4).sub.3, N(R.sup.E4).sub.2, P(═O)(R.sup.E4).sub.2, OR.sup.E4, S(═O)R.sup.E4, S(═O).sub.2R.sup.E4, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are each substituted by R.sup.E4 radicals; and where one or more CH.sub.2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups optionally are replaced by —R.sup.E4C═CR.sup.E4—, —C≡C—, Si(R.sup.E4).sub.2, C═O, C═NR.sup.E4, —C(═O)O—, —C(═O)NR.sup.E4—, NR.sup.E4, P(═O)(R.sup.E4), —O—, —S—, SO or SO.sub.2; R.sup.E2 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(═O)R.sup.E4, CN, Si(R.sup.E4).sub.3, N(R.sup.E4).sub.2, P(═O)(R.sup.E4).sub.2, OR.sup.E4, S(═O)R.sup.E4, S(═O).sub.2R.sup.E4, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are each substituted by R.sup.E4 radicals; and where one or more CH.sub.2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups optionally are replaced by —R.sup.E4C═CR.sup.E4—, —C≡C—, Si(R.sup.E4).sub.2, C═O, C═NR.sup.E4, —C(═O)O—, —C(═O)NR.sup.E4—, NR.sup.E4, P(═O)(R.sup.E4), —O—, —S—, SO or SO.sub.2; where two or more R.sup.E2 radicals may be joined to one another and may form a ring, and where one or more R.sup.E2 radicals may be joined via their R.sup.E4 radicals to a ring selected from C.sup.1, C.sup.2 and C.sup.3 and may form a ring; R.sup.E3 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(═O)R.sup.E4, CN, Si(R.sup.E4).sub.3, N(R.sup.E4).sub.2, P(═O)(R.sup.E4).sub.2, OR.sup.E4, S(═O)R.sup.E4, S(═O).sub.2R.sup.E4, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R.sup.E3 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are each substituted by R.sup.E4 radicals; and where one or more CH.sub.2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups optionally are replaced by —R.sup.E4C═CR.sup.E4—, —C≡C—, Si(R.sup.E4).sub.2, C═O, C═NR.sup.E4, —C(═O)O—, —C(═O)NR.sup.E4—, NR.sup.E4, P(═O)(R.sup.E4), —O—, —S—, SO or SO.sub.2; R.sup.E4 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(═O)R.sup.E5CN, Si(R.sup.E5).sub.3, N(R.sup.E5).sub.2, P(═O)(R.sup.E5).sub.2, OR.sup.E5, S(═O)R.sup.E5, S(═O).sub.2R.sup.E5, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R.sup.E4 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are each substituted by R.sup.E5 radicals; and where one or more CH.sub.2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups optionally are replaced by —R.sup.E5C═CR.sup.E5—, —C≡C—, Si(R.sup.E5).sub.2, C═O, C═NR.sup.E5, —C(═O)O—, —C(═O)NR.sup.E5—, NR.sup.E5, P(═O)(R.sup.E5), —O—, —S—, SO or SO.sub.2; R.sup.E5 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R.sup.E5 radicals may be joined to one another and may form a ring; and where the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems optionally substituted by one or more radicals selected from F and CN; and p are the same or different and are 0 or 1, where p=0 and o=0 mean that the X group indicated by p or o together with its bonds to the rings C.sup.1, C.sup.2 and C.sup.3 is absent; a layer H1 which is disposed between the first electrode and the emitting layer and contains a compound of a formula (L-1), (L-2) or (L-3) ##STR01828## for which: Z, when a —[Ar.sup.1].sub.n—N(Ar.sup.2).sub.2 group is bonded thereto, is C, and Z, when no —[Ar.sup.1].sub.n—N(Ar.sup.2).sub.2 group is bonded thereto, is the same or different at each instance and is N or CR.sup.1; Ar.sup.1 is the same or different at each instance and is an aromatic ring system which has 6 to 40 aromatic ring atoms and is substituted by R.sup.3 radicals, or a heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is substituted by R.sup.3 radicals; Ar.sup.2 is the same or different at each instance and is an aromatic ring system which has 6 to 40 aromatic ring atoms and is substituted by R.sup.3 radicals, or a heteroaromatic ring system which has 5 to 40 aromatic ring atoms and is substituted by R.sup.3 radicals; R.sup.1 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(═O)R.sup.4, CN, Si(R.sup.4).sub.3, N(R.sup.4).sub.2, P(═O)(R.sup.4).sub.2, OR.sup.4, S(═O)R.sup.4, S(═O).sub.2R.sup.4, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R.sup.1 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are each substituted by R.sup.4 radicals; and where one or more CH.sub.2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups optionally are replaced by —R.sup.4C═CR.sup.4—, —C≡C—, Si(R.sup.4).sub.2, C═O, C═NR.sup.4, —C(═O)O—, —C(═O)NR.sup.4—, NR.sup.4, P(═O)(R.sup.4), —O—, —S—, SO or SO.sub.2; R.sup.2 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(═O)R.sup.4, CN, Si(R.sup.4).sub.3, N(R.sup.4).sub.2, P(═O)(R.sup.4).sub.2, OR.sup.4, S(═O)R.sup.4, S(═O).sub.2R.sup.4, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R.sup.2 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are each substituted by R.sup.4 radicals; and where one or more CH.sub.2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups optionally are replaced by —R.sup.4C═CR.sup.4—, —C≡C—, Si(R.sup.4).sub.2, C═O, C═NR.sup.4, —C(═O)O—, —C(═O)NR.sup.4—, NR.sup.4, P(═O)(R.sup.4), —O—, —S—, SO or SO.sub.2; R.sup.3 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(═O)R.sup.4, CN, Si(R.sup.4).sub.3, N(R.sup.4).sub.2, P(═O)(R.sup.4).sub.2, OR.sup.4, S(═O)R.sup.4, S(═O).sub.2R.sup.4, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R.sup.3 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are each substituted by R.sup.4 radicals; and where one or more CH.sub.2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups optionally are replaced by —R.sup.4C═CR.sup.4—, —C≡C—, Si(R.sup.4).sub.2, C═O, C═NR.sup.4, —C(═O)O—, —C(═O)NR.sup.4—, NR.sup.4, P(═O)(R.sup.4), —O—, —S—, SO or SO.sub.2; R.sup.4 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, C(═O)R.sup.5, CN, Si(R.sup.5).sub.3, N(R.sup.5).sub.2, P(═O)(R.sup.5).sub.2, OR.sup.5, S(═O)R.sup.5, S(═O).sub.2R.sup.5, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R.sup.4 radicals may be joined to one another and may form a ring; where the alkyl, alkoxy, alkenyl and alkynyl groups and the aromatic ring systems and heteroaromatic ring systems are each substituted by R.sup.5 radicals; and where one or more CH.sub.2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups optionally are replaced by —R.sup.5C═CR.sup.5—, —C≡C—, Si(R.sup.5).sub.2, C═O, C═NR.sup.5, —C(═O)O—, —C(═O)NR.sup.5—, NR.sup.5, P(═O)(R.sup.5), —O—, —S—, SO or SO.sub.2; R.sup.5 is the same or different at each instance and is selected from H, D, F, Cl, Br, I, CN, alkyl or alkoxy groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more R.sup.5 radicals may be joined to one another and may form a ring; and where the alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems optionally substituted by one or more radicals selected from F and CN; n is the same or different at each instance and is 0, 1, 2, 3 or 4; k is 0 or 1; and a layer H2 disposed between layer H1 and the emitting layer.

26. The electronic device according to claim 25, wherein the T group is B.

27. The electronic device according to claim 25, wherein the X group is the same at each instance and is NR.sup.E2.

28. The electronic device according to claim 25, wherein R.sup.E2 is the same or different at each instance and is selected from aromatic ring systems which have 6 to 40 aromatic ring atoms and are each substituted by R.sup.E4 radicals, where two or more R.sup.E2 radicals may be joined to one another and may form a ring and where one or more R.sup.E2 radicals may be joined via their R.sup.E4 radicals to a ring selected from C.sup.1, C.sup.2 and C.sup.3 and may form a ring.

29. The electronic device according to claim 25, wherein R.sup.E3 is the same or different at each instance and is selected from H, D, F, CN, Si(R.sup.E4).sub.3, N(R.sup.E4).sub.2, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the alkyl and alkoxy groups, the aromatic ring systems and the heteroaromatic ring systems are each substituted by one or more R.sup.E4 radicals; and where one or more CH.sub.2 groups in the alkyl or alkoxy groups optionally are replaced by —C≡C—, —R.sup.E4C═CR.sup.E4—, Si(R.sup.E4).sub.2, C═O, C═NR.sup.E4, —NR.sup.E4—, —O—, —S—, —C(═O)O— or —C(═O)NR.sup.E4—.

30. The electronic device according to claim 25, wherein at least one R.sup.E3 radical in formula (E-1) is selected from alkyl groups which have 1 to 10 carbon atoms and are substituted by R.sup.E4 radicals, and N(R.sup.E4).sub.2.

31. The electronic device according to claim 25, wherein R.sup.E4 is the same or different at each instance and is selected from H, D, F, CN, Si(R.sup.E5).sub.3, N(R.sup.E5).sub.2, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the alkyl and alkoxy groups, the aromatic ring systems and the heteroaromatic ring systems are each substituted by one or more R.sup.E5 radicals; and where one or more CH.sub.2 groups in the alkyl or alkoxy groups optionally are replaced by —C≡C—, —R.sup.E5C═CR.sup.E5—, Si(R.sup.E5).sub.2, C═O, C═NR.sup.E5, —NR.sup.E5—, —O—, —S—, —C(═O)O— or —C(═O)NR.sup.E5—.

32. The electronic device according to claim 25, wherein one of the indices o and p is 1, and the other of the indices o and p is 0.

33. The electronic device according to claim 25, wherein the compound of the formula (E-1) conforms to one of the formulae (E-1-1-1-1-1) and (E-1-1-1-1-2) ##STR01829## where R.sup.E3-1 is as defined for R.sup.E3; and R.sup.E3-2 is selected from alkyl groups which have 1 to 10 carbon atoms and are substituted by R.sup.E4 radicals, preferably methyl, ethyl, isopropyl and tert-butyl, more preferably methyl; and R.sup.E4-1 is as defined for R.sup.E4.

34. The electronic device according to claim 25, wherein layer H comprises a compound of the formula (L-1).

35. The electronic device according to claim 25, wherein the compound of the formula (L-1) conforms to a formula selected from the formulae (L-1-1-1) to (L-1-1-3) ##STR01830## where R.sup.1-1 is the same or different at each instance and is selected from alkyl groups having 1 to 10 carbon atoms, and aromatic ring systems which have 6 to 40 aromatic ring atoms and are each substituted by R.sup.4 radicals, and where Z is CR.sup.1, and where Z is CH, and where the other variables are as defined in claim 25.

36. The electronic device according to claim 25, wherein R.sup.1 and R.sup.3 are the same or different at each instance and are selected from H, D, F, CN, Si(R.sup.4).sub.3, N(R.sup.4).sub.2, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms, where the alkyl and alkoxy groups, the aromatic ring systems and the heteroaromatic ring systems are each substituted by one or more R.sup.4 radicals; and where one or more CH.sub.2 groups in the alkyl or alkoxy groups optionally are replaced by —C≡C—, —R.sup.4C═CR.sup.4—, Si(R.sup.4).sub.2, C═O, C═NR.sup.4, —NR.sup.4—, —O—, —S—, —C(═O)O— or —C(═O)NR.sup.4—; and further wherein R.sup.2 is the same or different at each instance and is selected from alkyl groups having 1 to 10 carbon atoms, aromatic ring systems which have 6 to 40 aromatic ring atoms and are substituted by R.sup.4 radicals, and heteroaromatic ring systems substituted by R.sup.4 radicals; and further wherein R.sup.4 is the same or different at each instance and is selected from H, D, F, CN, Si(R.sup.5).sub.3, N(R.sup.5).sub.2, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the alkyl and alkoxy groups, the aromatic ring systems and the heteroaromatic ring systems are each substituted by R.sup.5 radicals; and where one or more CH.sub.2 groups in the alkyl or alkoxy groups optionally are replaced by —C≡C—, —R.sup.5C═CR.sup.5—, Si(R.sup.5).sub.2, C═O, C═NR.sup.5, —NR.sup.5—, —O—, —S—, —C(═O)O— or —C(═O)NR.sup.5—.

37. The electronic device according to claim 25, wherein Ar.sup.1 groups are the same or different and are selected from divalent groups derived from benzene, biphenyl, terphenyl, naphthalene, fluorene, indenofluorene, indenocarbazole, spirobifluorene, dibenzofuran, dibenzothiophene, and carbazole, each of which optionally substituted by one or more R.sup.3 radicals.

38. The electronic device according to claim 25, wherein Ar.sup.2 is the same or different at each instance and is selected from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, especially 9,9′-dimethylfluorenyl and 9,9′-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, indenocarbazolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, benzofused dibenzofuranyl, benzofused dibenzothiophenyl, naphthyl-substituted phenyl, fluorenyl-substituted phenyl, spirobifluorenyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzothiophenyl-substituted phenyl, carbazolyl-substituted phenyl, pyridyl-substituted phenyl, pyrimidyl-substituted phenyl, and triazinyl-substituted phenyl, where the groups may each be substituted by one or more R.sup.3 radicals.

39. The electronic device according to claim 25, wherein layer H2 adjoins the emitting layer directly on the anode side.

40. The electronic device according to claim 25, wherein layer H2 comprises a compound that conforms to a formula selected from the formulae (L-1-2), (L-2-2), (L-3-1), (L-3-2), (L-4) and (L-5) ##STR01831## where Z is CR.sup.1, and Y is O, S or NR.sup.3; and m is 0, 1, 2 or 3; and the substituted positions on the benzene rings in formula (L-4) may each be substituted by an R.sup.3 radical, and the other variables are as defined in claim 25.

41. The electronic device according to claim 25, wherein the electronic device comprises, between anode and cathode: directly adjoining the anode, a hole injection layer (HIL), and directly adjoining the cathode side of the HIL, layer H1, and directly adjoining the cathode side of layer H1, layer H2, and directly adjoining the cathode side of layer H2, the emitting layer, and on the cathode side of the emitting layer, one or more electron-transporting layers.

42. The electronic device according to claim 25, wherein the emitting layer, in addition to the compound of the formula (E-1), comprises a matrix compound which is an anthracene compound.

43. The electronic device according to claim 25, wherein the electronic device is an organic electroluminescent device.

44. The electronic device according to claim 25, wherein the electronic device emits blue light.

45. The electronic device according to claim 25, wherein the electronic device is an organic electroluminescent device that emits light through the cathode.

46. The electronic device according to claim 25, wherein the electronic device comprises two or three identical or different layer sequences stacked one on top of another, where each of the layer sequences comprises the following layers: hole injection layer, hole transport layer, electron blocker layer, emitting layer, and electron transport layer, and wherein at least one of the layer sequences comprises an emitting layer E comprising a compound of the formula (E-1) a layer H1 which is disposed between the first electrode and the emitting layer and contains a compound of the formula (L-1), (L-2) or (L-3), and a layer H2 disposed between layer H1 and the emitting layer.

47. A process for producing a device according to claim 25, comprising first the providing of a substrate with an anode, the applying of layer H1 in a step that follows later, the applying of layer H2 in a step that follows later, the applying of the emitting layer in a step that follows later, and the applying of the anode in a step that follows later.

48. A Process comprising including the electronic device according to claim 25 in displays, as a light source in lighting applications or as a light source in medical and/or cosmetic applications.

Description

EXAMPLES

[0189] A) General Production Process for the OLEDs and Characterization of the OLEDs

[0190] Glass plaques which have been coated with structured ITO (indium tin oxide) in a thickness of 50 nm are the substrates to which the OLEDs are applied.

[0191] The OLEDs have the following layer structure: substrate/hole injection layer (HIL)/hole transport layer (HTL)/electron blocker layer (EBL)/emission layer (EML)/electron transport layer (ETL)/electron injection layer (EIL) and finally a cathode. The cathode is formed by an aluminium layer of thickness 100 nm. The exact structure of the OLEDs can be found in the tables which follow. The materials present in the individual layers of the OLED are shown in a table below.

[0192] All materials are applied by thermal vapour deposition in a vacuum chamber. In this case, the emission layer consists of at least one matrix material (host material) and an emitting dopant (emitter) which is added to the matrix material(s) in a particular proportion by volume by co-evaporation. Details given in such a form as H:SEB(95%:5%) mean here that the material H is present in the layer in a proportion by volume of 95% and the material SEB in a proportion by volume of 5%.

[0193] In an analogous manner, the electron transport layer and the hole injection layer consist of a mixture of two materials.

[0194] The OLEDs are characterized in a standard manner. For this purpose, the operating voltage and the external quantum efficiency (EQE, measured in %) as a function of the luminance, calculated from current-voltage-luminance characteristics assuming Lambertian radiation characteristics, are determined. The parameter EQE@10 mA/cm.sup.2 refers to the external quantum efficiency which is attained at 10 mA/cm.sup.2. The parameter U@10 mA/cm.sup.2 refers to the operating voltage at 10 mA/cm.sup.2.

[0195] B) Production and Characterization of Inventive OLEDs with a Bottom Emission Structure

[0196] OLEDs are produced with the following structure:

TABLE-US-00006 HIL HTL EBL EML ETL EIL Ex. Thickness/nm Thickness/nm Thickness/nm Thickness/nm Thickness/nm Thickness/nm C1 HTM-1: PDM (5%) HTM-1 EBM-1 H: PA(5%) ETM: LiQ(50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm I1 HTM-1: PDM (5%) HTM-1 EBM-1 H: SEB(5%) ETM: LiQ(50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm I2 HTM-2: PDM (5%) HTM-2 EBM-1 H: SEB(5%) ETM: LiQ(50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm I3 HTM-3: PDM (5%) HTM-3 EBM-1 H: SEB(5%) ETM: LiQ(50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm I4 HTM-4: PDM (5%) HTM-4 EBM-1 H: SEB(5%) ETM: LiQ(50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm

[0197] In OLEDs 11 to 14, there is variation in each case in the compound used in the HTL and HIL. Compounds HTM-1 to HTM-4 are used that are spirobifluorenylamines or fluorenylamines. In all cases, the spirobifluorenylamine EBM-1 is used in the EBL.

[0198] Comparative OLED C1 is of identical structure to OLED I1, with the sole difference that the compound PA rather than the compound SEB is present as emitter in the emitting layer.

[0199] The OLEDs can achieve the following device data:

TABLE-US-00007 U @ 10 mA/cm.sup.2 (V) EQE @ 10 mA/cm.sup.2 (%) C1 4.3 7.2 I1 4.0 8.9 I2 4.0 9.2 I3 4.1 8.7 I4 4.0 9.1

[0200] For all inventive OLEDs I1 to I4, a good operating voltage and high efficiency are achieved. The half-height width of the emission in all cases is about 26 nm.

[0201] The comparative OLED C1 shows distinctly poorer efficiency and a higher operating voltage than the corresponding inventive OLED I1.

[0202] In addition, OLEDs with the following structures are produced:

TABLE-US-00008 HIL HTL EBL EML ETL EIL Ex. Thickness/nm Thickness/nm Thickness/nm Thickness/nm Thickness/nm Thickness/nm I5 HTM-3: PDM (5%) HTM-3 EBM-2 H: SEB(5%) ETM: LiQ(50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm I6 HTM-3: PDM (5%) HTM-3 EBM-3 H: SEB(5%) ETM: LiQ(50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm I7 HTM-3: PDM (5%) HTM-3 EBM-4 H: SEB(5%) ETM: LiQ(50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm I8 HTM-3: PDM (5%) HTM-3 EBM-5 H: SEB(5%) ETM: LiQ(50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm I9 HTM-3: PDM (5%) HTM-3 EBM-6 H: SEB(5%) ETM: LiQ(50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm I10 HTM-3: PDM (5%) HTM-3 EBM-7 H: SEB(5%) ETM: LiQ(50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm

[0203] In OLEDs 15 to 110, the compound HTML-3 is always used in the HIL and the HTL. Compound HTL-3 is a 2-spirobifluorenylamine that bears a phenyl group as substituent on the spiro ring. In OLEDs 15 to 110, there is variation in the compound used in the EBL. Compounds EBM-2 to EBM-7 having different structures are used. Compounds EBM-2 to EBM-7 are selected from spirobifluorenylamines, indenofluorenylamines, fluorenylamines and amines having phenylenedibenzofuran groups on the amine.

[0204] The OLEDs can achieve the following device data:

TABLE-US-00009 U @ 10 mA/cm.sup.2 (V) EQE @ 10 mA/cm.sup.2 (%) I5 4.0 8.9 I6 4.0 8.9 I7 3.9 8.6 i8 3.9 8.5 I9 4.0 9.3 I10 4.0 9.1

[0205] A good operating voltage and high efficiency are achieved in all cases. The half-height width of the emission in all cases is about 28 nm.

[0206] C) Production and Characterization of Inventive OLEDs with a Top Emission Structure

[0207] OLEDs are produced with the following structure:

[0208] substrate /HIL/HTL/EBL/EML/ETL/EIL/cathode/outcoupling layer.

[0209] The substrate used here is a glass plaque coated with structured ITO (indium tin oxide) of thickness 50 nm. The cathode consists of a 15 nm-thick layer of a mixture of 91% Ag and 9% Mg. The outcoupling layer consists of a 70 nm-thick layer of the compound HTM-1. The structure of the layers HIL, HTL, EBL, EML, ETL and EIL is shown in the following table:

TABLE-US-00010 HIL HTL EBL EML ETL EIL Ex. Thickness/nm Thickness/nm Thickness/nm Thickness/nm Thickness/nm Thickness/nm I11 HTM-1: PDM (5%) HTM-1 EBM-1 H: SEB(4%) ETM: LiQ(50%) Yb: LiF(50%) 10 nm 118 nm 15 nm 20 nm 30 nm 2 nm

[0210] The OLED I11 has colour coordinates CIE x,y=0.14, 0.05. It attains a very high EQE at 10 mA/cm.sup.2 of 16%-19%. The emission band of the OLEDs is very narrow and has a half-height width between 17 and 18 nm.

[0211] In addition, it is possible to produce the following OLEDs with top emission structure in which, by comparison with OLED I11, HTM-1 has been respectively exchanged for HTM-2, HTM-3 or HTM-4, or EBM-1 for one of materials EBM-2 to EBM-7.

TABLE-US-00011 Ex. HIL HTL EBL EML ETL EIL I12 HTM-1: PDM (5%) HTM-1 EBM-2 H: SEB(4%) ETM: LiQ(50%) Yb: LiF(50%) I13 ″ ″ EBM-3 ″ ″ ″ I14 ″ ″ EBM-4 ″ ″ ″ I15 ″ ″ EBM-5 ″ ″ ″ I16 ″ ″ EBM-6 ″ ″ ″ I17 ″ ″ EBM-7 ″ ″ ″ I18 HTM-2: PDM (5%) HTM-2 EBM-1 ″ ″ ″ I19 ″ ″ EBM-2 ″ ″ ″ I20 ″ ″ EBM-3 ″ ″ ″ I21 ″ ″ EBM-4 ″ ″ ″ I22 ″ ″ EBM-5 ″ ″ ″ I23 ″ ″ EBM-6 ″ ″ ″ I24 ″ ″ EBM-7 ″ ″ ″ I25 HTM-3: PDM (5%) HTM-3 EBM-1 ″ ″ ″ I26 ″ ″ EBM-2 ″ ″ ″ I27 ″ ″ EBM-3 ″ ″ ″ I28 ″ ″ EBM-4 ″ ″ ″ I29 ″ ″ EBM-5 ″ ″ ″ I30 ″ ″ EBM-6 ″ ″ ″ I31 ″ ″ EBM-7 ″ ″ ″ I32 HTM-4: PDM (5%) HTM-4 EBM-1 ″ ″ ″ I33 ″ ″ EBM-2 ″ ″ ″ I34 ″ ″ EBM-3 ″ ″ ″ I35 ″ ″ EBM-4 ″ ″ ″ I36 ″ ″ EBM-5 ″ ″ ″ I37 ″ ″ EBM-6 ″ ″ ″ I38 ″ ″ EBM-7 ″ ″ ″

[0212] It is possible here to obtain OLEDs having the colour coordinates CIE x,y=0.14, 0.05. After adjustment of the layer thicknesses to the material combination used in order to optimize the resonance effect, it is possible using these OLEDs to attain very high EQE values at 10 mA/cm.sup.2 of 16-19%, and very small half-height widths of the emission band of 17 to 18 nm.

TABLE-US-00012 Compounds used [01810] [01811] [01812] [01813] [01814] [01815] [01816] [01817] [01818] [01819] [01820] [01821] [01822] [01823] [01824] [01825] [01826]