ELECTRONIC DEVICE

Abstract

The invention relates to an electronic device, to the use thereof, and to a method for the production thereof.

Claims

1.-20. (canceled)

21. An electronic device comprising a first electrode, a second electrode and, arranged inbetween, an emitting layer comprising a compound of a formula (EM-1) ##STR01886## 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 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 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 optionally joined to one another and may form a ring, and where one or more R.sup.E2 radicals optionally 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 optionally 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 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.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.E4 radicals optionally 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 is optionally 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 optionally 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; o 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 E which is disposed between the emitting layer and the second electrode and comprises a compound of a formula (E-1) ##STR01887## where A is ##STR01888## O or S, where the dotted bonds indicate the bonds of A to the rest of the formula; Z, when no ##STR01889## group is bonded thereto, is the same or different at each instance and is N and CR.sup.1, and, when a ##STR01890## group is bonded thereto, is C; V is the same or different at each instance and is selected from N and CR.sup.4, where at least two V groups in the ring must be N; Ar.sup.1 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 substituted by R.sup.3 radicals, and heteroaromatic ring systems which have 5 to 40 aromatic ring atoms and are 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.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.1 radicals optionally 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 is optionally 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.2 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.2 radicals optionally 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 is optionally 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.3 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.3 radicals optionally 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 is optionally 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.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 optionally 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 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, C(═O)R.sup.6, CN, Si(R.sup.6).sub.3, N(R.sup.6).sub.2, P(═O)(R.sup.6).sub.2, OR.sup.6, S(═O)R.sup.6, S(═O).sub.2R.sup.6, 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.5 radicals optionally 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.6 radicals; and where one or more CH.sub.2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups is optionally replaced by —R.sup.6C═CR.sup.6—, —C≡C—, Si(R.sup.6).sub.2, C═O, C═NR.sup.6, —C(═O)O—, —C(═O)NR.sup.6—, NR.sup.6, P(═O)(R.sup.6), —O—, —S—, SO or SO.sub.2; R.sup.6 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.6 radicals optionally 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 is optionally substituted by one or more radicals selected from F and CN; n is 0, 1, 2, 3 or 4.

22. The electronic device as claimed in claim 21, wherein T is B.

23. The electronic device as claimed in claim 21, wherein X is selected to be the same at each instance and is NR.sup.E2.

24. The electronic device as claimed in claim 21, 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 optionally joined to one another and may form a ring and where one or more R.sup.E2 radicals optionally 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; and 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 R.sup.E4 radicals; and where one or more CH.sub.2 groups in the alkyl or alkoxy groups optionally 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—; and 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 R.sup.E5 radicals; and where one or more CH.sub.2 groups in the alkyl or alkoxy groups optionally 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.

25. The electronic device as claimed in claim 21, wherein at least one R.sup.E3 radical in formula (EM-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.

26. The electronic device as claimed in claim 21, wherein one of the indices o and p is 1, and the other of the indices o and p is 0.

27. The electronic device as claimed in claim 21, wherein the compound of the formula (EM-1) conforms to a formula selected from the formulae (EM-1-1-1-1-1) and (EM-1-1-1-1-2) ##STR01891## 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.

28. The electronic device as claimed in claim 21, wherein Z is CR.sup.1 when no ##STR01892## group is bonded thereto.

29. The electronic device as claimed in claim 21, wherein ##STR01893## groups are selected from the following groups: ##STR01894## where the dotted line represents the bond to the rest of the formula.

30. The electronic device as claimed in claim 21, wherein Ar.sup.1 is the same or different at each instance and is 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.

31. The electronic device as claimed in claim 21, wherein R.sup.1 is the same or different at each instance and is selected from H, F, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where the aromatic ring systems and the heteroaromatic ring systems are each substituted by R.sup.5 radicals; and R.sup.2 is the same or different at each instance and is selected from straight-chain alkyl groups having 1 to 20 carbon atoms, branched alkyl 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 said alkyl groups, said aromatic ring systems and said heteroaromatic ring systems are each substituted by R.sup.5 radicals; and R.sup.3 is the same or different at each instance and is selected from H, D, F, CN, Si(R.sup.5).sub.3, 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 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—; and R.sup.4 is the same or different at each instance and is selected from H and aromatic ring systems which have 6 to 40 aromatic ring atoms and are substituted by R.sup.5 radicals; and R.sup.5 is the same or different at each instance and is selected from H, D, F, CN, Si(R.sup.6).sub.3, 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.6 radicals; and where one or more CH.sub.2 groups in the alkyl or alkoxy groups optionally replaced by —C≡C—, —R.sup.6C═CR.sup.6—, Si(R.sup.6).sub.2, C═O, C═NR.sup.6, —NR.sup.6—, —O—, —S—, —C(═O)O— or —C(═O)NR.sup.6—.

32. The electronic device as claimed in claim 21, wherein the compound of the formula (E-1) conforms to a formula selected from the following formulae: ##STR01895## ##STR01896##

33. The electronic device as claimed in claim 21, wherein it is an organic electroluminescent device, in that the first electrode is an anode, in that the second electrode is a cathode, and in that layer E is an electron transport layer.

34. The electronic device as claimed in claim 21, wherein layer E comprises a mixture of an alkali metal salt and a further compound.

35. The electronic device as claimed in claim 21, wherein it comprises the following layers between anode and cathode: at least one hole-transporting layer between anode and emitting layer; the emitting layer between hole-transporting layer and cathode; and layer E as electron transport layer between emitting layer and cathode.

36. The electronic device as claimed in claim 21, wherein the emitting layer of the device, as well as the compound of the formula (EM-1), comprises one or more further compounds selected from anthracene derivatives and benzanthracene derivatives.

37. The electronic device as claimed in claim 21, wherein the 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 comprising a compound of the formula (EM-1), and a layer E, preferably as electron transport layer.

38. The electronic device as claimed in claim 21, wherein the device emits light through the cathode.

39. A process for producing an electronic device as claimed in claim 21, comprising the following steps: first providing a substrate with anode, in a later step applying the emitting layer comprising the compound of the formula (EM-1), in a subsequent step applying layer E, and in a subsequent step applying the anode.

40. A method comprising incorporating the electronic device as claimed in claim 21 in displays, as a light source in lighting applications, or as a light source in medical and/or cosmetic applications.

Description

EXAMPLES

[0203] A) General Production Process for the OLEDs and Characterization of the OLEDs

[0204] Glass plates which have been coated with structured ITO (indium tin oxide) in a thickness of 50 nm form the substrates to which the OLEDs are applied.

[0205] The OLEDs 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)/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 the tables which follow. The materials present in the individual layers of the OLED are shown in a table below.

[0206] All materials are applied by thermal vapor 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%. In an analogous manner, the electron transport layer and the hole injection layer also consist of a mixture of two materials.

[0207] 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 emission 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.

[0208] B) Performance Data of OLEDs of the Invention with Bottom Emission Structure and Compound of the Formula (E-1) in the ETL

[0209] OLEDs comprising a compound selected from compounds ETM1-ETM17 in the electron transport layer are produced:

TABLE-US-00006 HIL HTL EBL EML ETL EIL Ex. Thickness/nm Thickness/nm Thickness/nm Thickness/nm Thickness/nm Thickness/nm E1 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM1:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E2 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM2:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E3 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM3:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E4 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM4:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E5 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM5:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E6 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM6:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E7 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM7:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E8 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM8:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E9 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM9:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E10 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM10:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E11 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM11:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E12 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM12:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E13 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM13:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E14 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM14:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E15 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM15:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E16 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM16:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E17 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM17:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm

[0210] These OLEDs can be used to obtain the following performance data:

TABLE-US-00007 Ex. U @ 10 mA/cm.sup.2 (V) EQE @ 10 mA/cm.sup.2 (%) E1 4.0 8.9 E2 3.9 9.3 E3 3.8 9.7 E4 3.8 9.3 E5 3.9 9.9 E6 3.8 9.8 E7 4.0 8.5 E8 3.8 9.7 E9 4.1 9.1 E10 3.9 8.9 E11 3.9 9.5 E12 4.1 9.7 E13 4.1 8.9 E14 4.2 8.8 E15 3.8 9.4 E16 3.8 9.2 E17 3.9 9.4

[0211] All OLEDs E1 to E17 show very high values for efficiency at low operating voltage.

[0212] B) Comparison of the Performance Data Between OLEDs of the Invention and OLEDs Containing the Compound PA in the Emitting Layer

[0213] In addition to the OLEDs E1 and E9 detailed above, OLEDs containing the emitter PA rather than the emitter SEB in the emitting layer are produced:

TABLE-US-00008 HIL HTL EBL EML ETL EIL Ex. Thickness/nm Thickness/nm Thickness/nm Thickness/nm Thickness/nm Thickness/nm V1 HTM:p-dopant (5%) HTM EBM H:PA(5%) ETM1:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E1 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM1:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm V2 HTM:p-dopant (5%) HTM EBM H:PA(5%) ETM9:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm E9 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM9:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 30 nm 1 nm

[0214] The following results are obtained:

TABLE-US-00009 Ex. U @ 10 mA/cm.sup.2 (V) EQE @ 10 mA/cm.sup.2 (%) V1 4.3 7.2 E1 4.0 8.9 V2 4.4 7.6 E9 4.1 9.1

[0215] The results show that, in both cases, i.e. with the electron-transporting compound ETM1 and the electron-transporting compound ETM9 in the ETM, much better results for EQE and operating voltage are obtained for the OLEDs of the invention than for the OLEDs comprising the compound PA in the emitting layer.

[0216] D) Performance Data of OLEDs of the Invention with Bottom Emission Structure and Compound of the Formula (E-1) in the HBL

[0217] OLEDs comprising a compound selected from compounds ETM18 and ETM19 in the hole blocker layer (HBL), and compound ETM1 in the ETL, are produced. In addition, a comparative OLED (V3) is produced, which is identical in structure to OLED E18, with the sole difference that it contains the compound PA as emitter in the emitting layer, and not the compound SEB:

TABLE-US-00010 HIL HTL EBL EML HBL ETL EIL Ex. Thickness/nm Thickness/nm Thickness/nm Thickness/nm Thickness/nm Thickness/nm Thickness/nm V3 HTM:p-dopant (5%) HTM EBM H:PA(5%) ETM18 ETM1:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 10 nm 20 nm 1 nm E18 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM18 ETM1:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 10 nm 20 nm 1 nm E19 HTM:p-dopant (5%) HTM EBM H:SEB(5%) ETM19 ETM1:LiQ (50%) LiQ 20 nm 180 nm 10 nm 20 nm 10 nm 20 nm 1 nm

[0218] These OLEDs can be used to obtain the following performance data:

TABLE-US-00011 Ex. U @ 10 mA/cm.sup.2 (V) 10 mA/cm.sup.2 V3 4.2 6.7 E18 3.9 8.3 E19 4.0 8.5

[0219] The OLEDs of the invention containing the compound ETM18 or ETM19 in the HBL have very high values for efficiency at low operating voltage.

[0220] In the case of the comparative OLED V3 containing compound PA as emitter in the emitting layer rather than the compound SEB, the corresponding performance data are much worse.

[0221] E) Use of the compounds of the invention in the ETL of blue-fluorescing devices having top emission structure

[0222] OLEDs are produced with the following structure:

[0223] substrate/HIL/HTL/EBL/EML/ETL/EIL/cathode/outcoupling layer.

[0224] The substrate used here is a glass plate 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. The structure of the layers HIL, HTL, EBL, EML, ETL and EIL is shown in the following table:

TABLE-US-00012 HIL HTL EBL EML ETL EIL Ex. Thickness/nm Thickness/nm Thickness/nm Thickness/nm Thickness/nm Thickness/nm E20 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM1 LiQ(50%) Yb:LiF(50%) 10 nm 118 nm 15 nm 20 nm 30 nm 2 nm

[0225] The OLED E20 containing the compound ETM1 in the ETL has color 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.

[0226] In addition, it is possible to produce the following OLEDs with top emission structure in which, by comparison with OLED E20, the material ETM-1 has been exchanged for one of materials ETM-2 to ETM-17:

TABLE-US-00013 Ex. HIL HTL EBL EML ETL EIL E21 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM-2 LiQ (50%) Yb:LiF(50%) E22 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM-3 LiQ (50%) Yb:LiF(50%) E23 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM-4 LiQ (50%) Yb:LiF(50%) E24 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM-5 LiQ (50%) Yb:LiF(50%) E25 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM-6 LiQ (50%) Yb:LiF(50%) E26 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM-7 LiQ (50%) Yb:LiF(50%) E27 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM-8 LiQ (50%) Yb:LiF(50%) E28 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM-9:LiQ (50%) Yb:LiF(50%) E29 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM-10:LiQ (50%) Yb:LiF(50%) E30 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM-11:LiQ (50%) Yb:LiF(50%) E31 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM-12:LiQ (50%) Yb:LiF(50%) E32 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM-13 LiQ (50%) Yb:LiF(50%) E33 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM-14:LiQ (50%) Yb:LiF(50%) E34 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM-15:LiQ (50%) Yb:LiF(50%) E35 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM-16:LiQ (50%) Yb:LiF(50%) E36 HTM:p-dopant (5%) HTM EBM H:SEB(4%) ETM-17 LiQ (50%) Yb:LiF(50%)

[0227] It is possible here to obtain OLEDs having the color 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 for 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-00014 Compounds used [01860] p-Dopant [01861] SEB [01862] PA [01863] H [01864] HTM [01865] EBM [01866] ETM1 [01867] ETM2 [01868] ETM3 [01869] ETM4 [01870] ETM5 [01871] ETM6 [01872] ETM7 [01873] ETM8 [01874] ETM9 [01875] ETM10 [01876] ETM11 [01877] ETM12 [01878] ETM13 [01879] ETM14 [01880] ETM15 [01881] ETM16 [01882] ETM17 [01883] ETM18 [01884] ETM19 [01885] LiQ