COMPOSITION FOR ORGANIC ELECTRONIC DEVICES

Abstract

The present invention relates to a composition comprising an electron-transporting host and a hole-transporting host, to the use thereof in electronic devices and electronic devices comprising said composition. The electron-transporting host is more preferably selected from the class of the triazine-dibenzofuran-carbazole systems or the class of the triazine-dibenzothiophene-carbazole systems. The hole-transporting host is preferably selected from the class of biscarbazoles.

Claims

1. Composition comprising at least one compound of the formula (1) and at least one compound of the formula (2) ##STR02027## where the symbols and indices used are as follows: X.sub.1 is the same or different at each instance and is CR.sup.0 or N, with the proviso that at least one X.sub.1 group is N; X is the same or different at each instance and is C or N, where two adjacent X may be bonded to a ring system of the formula A, ##STR02028## where * at each instance is the bonding site to an X, Y.sup.1 is selected from NAr.sub.1, C(R*).sub.2, O and S; Y is selected from O and S; L is the same or different at each instance and is a single bond or an aromatic ring system which has 6 to 30 aromatic ring atoms and may be substituted by one or more R.sup.5 radicals; n and m at each instance are independently 0, 1, 2 or 3, o, p and q at each instance are independently 0, 1, 2, 3 or 4; Ar.sub.1 at each instance is independently an aryl or heteroaryl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals; R.sub.A is H, -L.sub.3-Ar.sub.4 or -L.sub.1-N(Ar).sub.2; R.sub.B is Ar.sub.3 or -L.sub.2-N(Ar).sub.2; L.sub.1, L.sub.2 are the same or different at each instance and are a single bond or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals; L.sub.3 is a single bond or an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, where one substituent R.sup.3 may form a ring with a substituent R.sup.2 on the carbazole; Ar.sub.3 is an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 10 to 40 aromatic ring atoms, which may be substituted by one or more R.sup.3 radicals; Ar.sub.4 is the same or different at each instance and is an unsubstituted or substituted 9-arylcarbazolyl or unsubstituted or substituted carbazol-9-yl, which may be substituted by one or more R.sup.4 radicals, and where one or more instances each of two R.sup.4 radicals or one R.sup.4 radical together with one R.sup.2 radical may independently form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring, where aryl is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by R.sup.3; R* is the same or different at each instance and is a straight-chain alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 12 carbon atoms, where two substituents R* together may form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more substituents R.sup.5; R.sup.0, R, R.sup.1, R.sup.2 are the same or different at each instance and are selected from the group consisting of H, D, F, Cl, Br, I, CN, NO.sub.2, N(Ar).sub.2, N(R.sup.3).sub.2, C(═O)Ar, C(═O)R.sup.3, P(═O)(Ar).sub.2, P(Ar).sub.2, B(Ar).sub.2, Si(Ar).sub.3, Si(R.sup.3).sub.3, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 carbon atoms or an alkenyl group having 2 to 20 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by R.sup.3C═CR.sup.3, Si(R.sup.3).sub.2, C═O, C═S, C═NR.sup.3, P(═O)(R.sup.3), SO, SO.sub.2, NR.sup.3, O, S or CONR.sup.3 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms and may be substituted in each case by one or more R.sup.3 radicals, an aryloxy or heteroaryloxy group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or an aralkyl or heteroaralkyl group which has 5 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals; at the same time, it is optionally possible for two substituents R.sup.0 and/or R and/or R.sup.1 and/or R.sup.2 bonded to the same carbon atom or to adjacent carbon atoms to form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R.sup.3 radicals; R.sup.3 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, N(Ar).sub.2, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN and which may be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; at the same time, it is possible for two or more adjacent R.sup.3 substituents together to form a mono- or polycyclic, aliphatic ring system; R.sup.4 is the same or different at each instance and is selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbyl radical having 1 to 20 carbon atoms, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, a straight-chain or branched alkyl group having 1 to 4 carbon atoms or CN; at the same time, two or more adjacent R.sup.4 substituents together may form a mono- or polycyclic ring system; R.sup.5 is the same or different at each instance and is selected from the group consisting of D, F, CN and an aryl group having 6 to 18 carbon atoms; at the same time, two or more adjacent substituents R.sup.5 together may form a mono- or polycyclic, aliphatic ring system; Ar is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 5 to 30 aromatic ring atoms and may be substituted by one or more nonaromatic R.sup.3 radicals; at the same time, two Ar radicals bonded to the same nitrogen atom, phosphorus atom or boron atom may also be bridged to one another by a single bond or a bridge selected from N(R.sup.3), C(R.sup.3).sub.2, O and S, and r at each instance is independently 0, 1, 2 or 3; s at each instance is independently 0, 1, 2, 3 or 4.

2. The composition according to claim 1, characterized in that Y in formula (1) is O.

3. The composition according to claim 1, characterized in that the compound of the formula (2) conforms to one of the formulae (2a) to (2d) ##STR02029## where the symbols and indices L.sub.1, L.sub.2, L.sub.3, Ar, Ar.sub.3, Ar.sub.4, R.sup.2, r and s used are as defined in claim 1.

4. The composition according to claim 1, wherein the composition comprises at least one further compound selected from the group consisting of hole injection materials, hole transport materials, hole blocker materials, wide band gap materials, fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron blocker materials, electron transport materials and electron injection materials, n-dopants and p-dopants.

5. The composition according to the claim 1, wherein composition consists of a compound of the formula (1) and a compound of the formula (2).

6. A formulation comprising the composition according to claim 1 and at least one solvent.

7. Use of the composition according to claim 1 in an organic electronic device.

8. Use according to claim 7, characterized in that the organic electronic device is selected from the group of organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors and organic photoreceptors.

9. An organic electronic device comprising at least one composition according to claim 1 in at least one organic layer.

10. The device according to claim 9, wherein the device is selected from the group of organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors and organic photoreceptors.

11. The device according to claim 9, characterized in that the device is an electroluminescent device selected from the group consisting of organic light-emitting transistors (OLETs), organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O-lasers) and organic light-emitting diodes (OLEDs).

12. The device according to claim 9, wherein the device comprises the composition in an emission layer (EML), in an electron transport layer (ETL), in an electron injection layer (EIL) and/or in a hole blocker layer (HBL).

13. The device according to claim 11, comprising an anode, a cathode and at least one organic layer containing at least one light emitting layer, characterized in that it contains the composition in the at least one emission layer together with a phosphorescent emitter.

14. A process for producing the device according to claim 9, wherein at least one organic layer comprising composition is applied by gas phase deposition or from solution.

15. The process according to claim 14, characterized in that the at least one compound of the formula (1) and the at least one compound of the formula (2) are deposited from the gas phase successively or simultaneously from at least two material sources, optionally together with further materials, and form the organic layer.

16. The process according to claim 14, characterized in that the composition is utilized as material source for gas phase deposition of the host system and forms the organic layer optionally together with further materials.

17. The process according to claim 14, characterized in that a formulation comprising the composition and the solvent is used in order to apply the organic layer.

Description

EXAMPLE 1: PRODUCTION OF THE OLEDS

[0289] Examples I1 to I55 which follow (see Table 6) present the use of the material combinations of the invention in OLEDs by comparison with examples C1 to C11.

[0290] Pretreatment for Examples C1-I55: Glass plaques coated with structured ITO (indium tin oxide) of thickness 50 nm are treated prior to coating, first with an oxygen plasma, followed by an argon plasma. These plasma-treated glass plaques form the substrates to which the OLEDs are applied.

[0291] The OLEDs basically have the following layer structure: substrate/hole injection layer (HIL)/hole transport layer (HTL)/electron blocker layer (EBL)/emission layer (EML)/optional hole blocker layer (HBL)/electron transport layer (ETL)/optional electron injection layer (EIL) and finally a cathode. The cathode is formed by an aluminium layer of thickness 100 nm. The exact structure of the OLEDs can be found in table 6. The materials required for production of the OLEDs are shown in Table 8. The device data of the OLEDs are listed in Table 7. Examples C1, C2, C3, C10 and C11 are comparative examples with an electron-transporting host according to prior art CN107973786. Examples C4, C5, C6 and C7 are comparative examples with the host according to prior art WO 2015/014435. Examples C8 and C9 are comparative examples with the host according to prior art KR20160046077. Examples I1 to I55 show data for OLEDs of the invention.

[0292] All materials are applied by thermal vapour deposition in a vacuum chamber. In this case, the emission layer always consists of at least two matrix materials and an emitting dopant (emitter) which is added to the matrix material(s) in a particular proportion by volume by co-evaporation. Details given in such a form as SoA1:40:TEG3 (32%:60%:8%) mean here that the material SoA1 is present in the layer in a proportion by volume of 32%, compound 40 as a co-host in a proportion of 60%, and TEG3 in a proportion of 8%. Analogously, the electron transport layer may also consist of a mixture of two materials.

[0293] The OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectra and the current efficiency (SE, measured in cd/A) as a function of luminance, calculated from current-voltage-luminance characteristics (IUL characteristics) assuming Lambertian radiation characteristics, and the lifetime are measured. The electroluminescence spectra are determined at a luminance of 1000 cd/m.sup.2, and the CIE 1931 x and y colour coordinates are calculated therefrom. The parameter U10 in Table 7 refers to the voltage which is required for a current density of 10 mA/cm.sup.2. PE10 refers to the power efficiency attained at 10 mA/cm.sup.2. The lifetime LT is defined as the time after which the luminance drops to a certain proportion L1 in the course of operation with the same starting brightness L0. A figure of L1=80% in Table 7 means that the lifetime in hours (h) reported in the LT column corresponds to the time after which the luminance falls to 80% of its starting value.

[0294] In other words, for example, given an L0 of 20 000 cd/m.sup.2, this would be the time taken for the sample to have only a luminance of

L1=0.8×L0=16 000 cd/m.sup.2.

[0295] Use of Mixtures of the Invention in OLEDs

[0296] The material combinations of the invention can be used in the emission layer in phosphorescent green OLEDs. The inventive combinations of the compounds 2, 3, 4, 5, 6, 9, 11, 13, 14, 17, 18, 22, 28, 30, 31, 32, 33, 34, 67, 69, 70, 72, 75, 76, 77 and 79 with compound 37, 38, 40, 41, 42, 43, 44, 47, 48, 49, 52, 56, 58, 60, 61, 62, 63, 64, 65, 66 or 66a are used in examples 11 to 155 as matrix material in the emission layer, as described in Table 6. The results from Table 7 are directly comparable when the same emitter has been used, for example C1 with I1 or I1 with I4 or C2 with I2.

[0297] For instance, on comparison of the inventive examples with the corresponding comparative examples, such as I1 versus C1, I2 versus C2, I3 versus C3, I27 versus C4, I28, versus C5, I29 versus C6, I30 versus C7, I31 versus C8, I32 versus C9, I33 versus I10 and I34 versus C11, it is clearly apparent that the inventive examples each show a distinct advantage in lifetime.

TABLE-US-00006 TABLE 6 Structure of the OLEDs HIL HTL EBL EML HBL ETL EIL Ex thickness thickness thickness thickness thickness thickness thickness C1 HTCN SpMA1 SpMA2 SoA1:40:TEG3 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (32%:60%:8%) 30 nm 10 nm (50%:50%) 1 nm 30 nm C 2 HTCN SpMA1 SpMA2 SoA1:48:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (59%:29%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm C 3 HTCN SpMA1 SpMA2 SoA1:44:TEG2 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (31%:62%:7%) 40 nm 10 nm (50%:50%) 1 nm 30 nm I1 HTCN SpMA1 SpMA2 4:40:TEG3 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (32%:60%:8%) 30 nm 10 nm (50%:50%) 1 nm 30 nm I2 HTCN SpMA1 SpMA2 4:48:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (59%:29%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm I3 HTCN SpMA1 SpMA2 4:44:TEG2 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (31%:62%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I4 HTCN SpMA1 SpMA2 4:40:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (31%:62%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I5 HTCN SpMA1 SpMA2 4:40:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (31%:62%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I6 HTCN SpMA1 SpMA2 3:40:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (31%:62%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I7 HTCN SpMA1 SpMA2 3:40:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (33%:60%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I8 HTCN SpMA1 SpMA2 3:38:TEG3 ST2 ST2:LiQ LiQ 5 nm 215nm 20 nm (31%:62%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I9 HTCN SpMA1 SpMA2 3:38:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (33%:60%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I10 HTCN SpMA1 SpMA2 3:48:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (59%:29%:7%) 30 nm 10 nm (50%:50%) 1 nm 30 nm I11 HTCN SpMA1 SpMA2 5:48:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (59%:29%:7%) 30 nm 10 nm (50%:50%) 1 nm 30 nm I12 HTCN SpMA1 SpMA2 4:37:TEG3 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (32%:60%:8%) 30 nm 10 nm (50%:50%) 1 nm 30 nm I13 HTCN SpMA1 SpMA2 6:38:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (31%:62%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I14 HTCN SpMA1 SpMA2 6:58:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (31%:62%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I15 HTCN SpMA1 SpMA2 9:37:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (33%:60%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I16 HTCN SpMA1 SpMA2 9:47:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (71%:22%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I17 HTCN SpMA1 SpMA2 11:44:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (33%:60%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I18 HTCN SpMA1 SpMA2 11:52:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (33%:60%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I19 HTCN SpMA1 SpMA2 13:48:TEG1 ST2 ST2:LiQ LiQ 5 nm 230 nm 20 nm (59%:29%:12%) 10 nm (50%:50%) 1 nm 30 nm 30 nm I20 HTCN SpMA1 SpMA2 14:40:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (33%:60%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I21 HTCN SpMA1 SpMA2 17:38:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (33%:60%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I22 HTCN SpMA1 SpMA2 17:52:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (33%:60%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I23 HTCN SpMA1 SpMA2 18:47:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (71%:22%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I24 HTCN SpMA1 SpMA2 22:56:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (31%:62%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I25 HTCN SpMA1 SpMA2 31:44:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (33%:60%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I26 HTCN SpMA1 SpMA2 33:56:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (31%:62%:7%) 40 nm 5 nm (50%:50%) 1 nm 30 nm C4 HTCN SpMA1 SpMA2 SoA2:62:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I27 HTCN SpMA1 SpMA2 4:62:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm C5 HTCN SpMA1 SpMA2 SoA2:62:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I28 HTCN SpMA1 SpMA2 4:62:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm C6 HTCN SpMA1 SpMA2 SoA3:62:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I29 HTCN SpMA1 SpMA2 3:62:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm C7 HTCN SpMA1 SpMA2 SoA3:62:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I30 HTCN SpMA1 SpMA2 3:62:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm C8 HTCN SpMA1 SpMA2 SoA4:60:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I31 HTCN SpMA1 SpMA2 3:60:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm C9 HTCN SpMA1 SpMA2 SoA4:60:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I32 HTCN SpMA1 SpMA2 3:60:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm C10 HTCN SpMA1 SpMA2 SoA5:38:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I33 HTCN SpMA1 SpMA2 67:38:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm C11 HTCN SpMA1 SpMA2 SoA5:38:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I34 HTCN SpMA1 SpMA2 67:38:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I35 HTCN SpMA1 SpMA2 70:37:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I36 HTCN SpMA1 SpMA2 69:37:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I37 HTCN SpMA1 SpMA2 70:63:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I38 HTCN SpMA1 SpMA2 34:66:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I39 HTCN SpMA1 SpMA2 30:65:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I40 HTCN SpMA1 SpMA2 72:41:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I41 HTCN SpMA1 SpMA2 72:41:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I42 HTCN SpMA1 SpMA2 72:63:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I43 HTCN SpMA1 SpMA2 75:42:TEG1 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I44 HTCN SpMA1 SpMA2 75:60:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I45 HTCN SpMA1 SpMA2 76:37:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I46 HTCN SpMA1 SpMA2 77:43:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I47 HTCN SpMA1 SpMA2 77:44:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I48 HTCN SpMA1 SpMA2 77:61:TEG1 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I49 HTCN SpMA1 SpMA2 79:40:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I50 HTCN SpMA1 SpMA2 79:49:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I51 HTCN SpMA1 SpMA2 79:47:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I52 HTCN SpMA1 SpMA2 28:66:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I53 HTCN SpMA1 SpMA2 2:64:TEG1 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I54 HTCN SpMA1 SpMA2 32:62:TEG2 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm I55 HTCN SpMA1 SpMA2 3:66a:TEG3 ST2 ST2:LiQ LiQ 5 nm 215 nm 20 nm (32%:60%:8%) 40 nm 5 nm (50%:50%) 1 nm 30 nm

TABLE-US-00007 TABLE 7 Data of the OLEDs PE10 CIE x/y at L0 L1 LT Ex. U10 (cd/A) 1000 cd/cm.sup.2 (Cd/m.sup.2) (%) (h) C1 4.4 58 0.36/0.60 20000 80 790 C2 4.5 52 0.35/0.61 20000 80 245 C3 4.8 74 0.34/0.63 20000 80 1790 I1 4.4 69 0.36/0.60 20000 80 890 I2 4.3 68 0.36/0.61 20000 80 270 I3 5.0 92 0.34/0.63 20000 80 1950 I4 4.9 75 0.33/0.62 20000 80 1170 I5 4.6 88 0.34/0.63 20000 80 2100 I6 5.0 73 0.33/0.62 20000 80 1220 I7 4.6 90 0.34/0.63 20000 80 2700 I8 4.9 72 0.33/0.62 20000 80 1250 I9 4.5 89 0.34/0.63 20000 80 2750 I10 4.4 71 0.35/0.61 20000 80 360 I11 4.1 66 0.35/0.61 20000 80 490 I12 4.4 68 0.36/0.60 20000 80 910 I13 4.6 87 0.34/0.63 20000 80 2150 I14 4.6 86 0.34/0.63 20000 80 2000 I15 4.5 88 0.34/0.63 20000 80 2600 I16 4.4 78 0.34/0.63 20000 80 1510 I17 4.9 95 0.34/0.63 20000 80 2510 I18 4.2 87 0.34/0.63 20000 80 1890 I19 4.3 67 0.36/0.61 20000 80 255 I20 4.6 89 0.34/0.63 20000 80 2600 I21 4.6 90 0.34/0.63 20000 80 2500 I22 4.2 88 0.34/0.63 20000 80 1910 I23 4.4 77 0.34/0.63 20000 80 1530 I24 5.1 78 0.34/0.63 20000 80 1310 I25 4.9 95 0.34/0.63 20000 80 2520 I26 5.1 76 0.34/0.63 20000 80 1290 C4 5.2 71 0.33/0.62 20000 80 1090 I27 5.2 73 0.33/0.62 20000 80 1560 C5 5.0 85 0.34/0.63 20000 80 1640 I28 4.9 86 0.34/0.63 20000 80 2250 C6 5.3 70 0.33/0.62 20000 80 980 I29 5.4 74 0.33/0.62 20000 80 1770 C7 5.1 83 0.34/0.63 20000 80 1960 I30 4.9 88 0.34/0.63 20000 80 2930 C8 5.2 75 0.33/0.62 20000 80 780 I31 5.4 74 0.33/0.62 20000 80 1120 C9 4.8 89 0.34/0.63 20000 80 860 I32 4.8 90 0.34/0.63 20000 80 1570 C10 4.9 67 0.33/0.62 20000 80 800 I33 5.0 75 0.33/0.62 20000 80 1240 C11 4.9 79 0.34/0.63 20000 80 1640 I34 4.8 84 0.34/0.63 20000 80 1990 I35 4.5 92 0.34/0.63 20000 80 2550 I36 4.6 91 0.34/0.63 20000 80 2130 I37 4.8 89 0.34/0.63 20000 80 2880 I38 5.2 73 0.33/0.62 20000 80 1950 I39 4.9 85 0.34/0.63 20000 80 1640 I40 4.6 88 0.34/0.63 20000 80 2530 I41 4.7 73 0.33/0.62 20000 80 1400 I42 4.8 85 0.34/0.63 20000 80 2970 I43 4.5 70 0.36/0.61 20000 80 330 I44 4.9 93 0.34/0.63 20000 80 1780 I45 4.6 74 0.33/0.62 20000 80 1220 I46 4.8 90 0.34/0.63 20000 80 1710 I47 4.9 88 0.34/0.63 20000 80 1950 I48 5.3 71 0.36/0.61 20000 80 470 I49 5.0 72 0.33/0.62 20000 80 1290 I50 4.6 76 0.33/0.62 20000 80 960 I51 4.7 65 0.33/0.62 20000 80 1140 I52 5.1 87 0.34/0.63 20000 80 2640 I53 4.7 73 0.36/0.61 20000 80 460 I54 4.9 94 0.34/0.63 20000 80 2020 I55 5.2 71 0.33/0.62 20000 80 1850

TABLE-US-00008 TABLE 8 Structural formulae of the materials in the OLEDs [01809] HTCN [01810] SpA1 [01811] SpMA2 [01812] ST2 [01813] TEG1 [01814] TEG2 [01815] TEG3 [01816] LiQ [01817] SoA1 [CAS-2226338-95-8] [01818] SoA2 [CAS-1651195-45-7] [01819] SoA3 [CAS-1651195-58-2] [01820] SoA4 [CAS-1829595-17-6] [01821] SoA5 [CAS-2226339-15-5] [01822] 3 [01823] 4 [01824] 5 [01825] 6 [01826] 9 [01827] 11 [01828] 13 [01829] 14 [01830] 17 [01831] 18 [01832] 22 [01833] 28 [01834] 30 [01835] 31 [01836] 32 [01837] 33 [01838] 34 [01839] 37 [01840] 38 [01841] 40 [01842] 41 [01843] 42 [01844] 43 [01845] 44 [01846] 47 [01847] 48 [01848] 49 [01849] 52 [01850] 56 [01851] 58 [01852] 60 [01853] 66a [01854] 61 [01855] 63 [01856] 62 [01857] 65 [01858] 64 [01859] 66 [01860] 67 [01861] 69 [01862] 70 [01863] 72 [01864] 75 [01865] 76 [01866] 77 [01867] 79

EXAMPLE 2: SYNTHESIS OF COMPOUNDS

a) 2-{12-chloro-8-oxatricyclo[7.4.0.0.SUP.2,7.]trideca-1(13),2(7),3,5,9,11-hexaen-3-yl}-4-{8-oxatricyclo[7.4.0.0.SUP.2,7.]trideca-1(9),2,4,6,10,12-hexaen-3-yl}-6-phenyl-1,3,5-triazine

[0298] ##STR01868##

[0299] 58 g (210 mmol; 1.00 eq.) of 1-boronyl-8-chlorodibenzofuran [CAS 162667-19-4], 90.2 g (252 mmol; 1.20 eq.) of 2-chloro-4-{8-oxatricyclo[7.4.0.0.sup.2,7]trideca-1 (9),2(7),3,5,10,12-hexaen-3-yl}-6-phenyl-1,3,5-triazine [CAS 1883265-32-4] and 44.5 g (420 mmol, 2.00 eq.) of sodium carbonate [CAS 497-19-8] are suspended in a mixture of 1000 ml of dioxane [CAS 123-91-1], 1000 ml of toluene [CAS 108-88-3] and 400 ml of water. To this suspension is added 4.85 g (4.20 mmol/0.02 eq.) of tetrakis(triphenylphosphine)palladium(0) [CAS 14221-01-3], and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is removed, filtered through silica gel, washed three times with 200 ml of water and then concentrated to dryness. The yield is 79.1 g (151 mmol; 72% of theory).

[0300] Rather than 1-boronyl-8-chlorodibenzofuran [CAS 162667-19-4], it is also possible to use 8-chloro-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzothiophene [CAS-2140848-96-8].

[0301] In an analogous manner, it is possible to obtain the following compounds:

TABLE-US-00009 No. Reactant 1 Product Yield 1a [01869] [01870] 80% 2a [01871] [01872] 65% 3a [01873] [01874] 67% 4a [01875] [01876] 75% 5a [01877] [01878] 72% 6a [01879] [01880] 74% 7a [01881] [01882] 67% 8a [01883] [01884] 65% 9a [01885] [01886] 62% 10a  [01887] [01888] 58% 11a  [01889] [01890] 75%

b) 3-Biphenyl-3-yl-9-[9-(4,6-diphenyl-[1,3,5]triazin-2-yl)-dibenzofuran-2-yl]-9H-carbazole

[0302] ##STR01891##

[0303] 21.4 g (42.7 mmol; 1.00 eq.) of 2-{12-bromo-8-oxatricyclo[7.4.0.0.sup.27]trideca-1(9),2(7),3,5,12-hexaen-3-yl}-4,6-diphenyl-1,3,5-triazine [CAS 1822310-63-3], 13.0 g (40.7 mmol; 1.10 eq.) of 3-biphenyl-3-yl-9H-carbazole [CAS 1643526-99-1] and 7.82 g (81.4 mmol; 2.00 eq.) of sodium tert-butoxide [CAS 865-47-4] are suspended in 500 ml of ortho-xylene [CAS 95-47-6]. To this suspension are added 1.50 g (3.66 mmol; 9 mol %) of dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (SPhos) [CAS 657408-07-6] and 1.12 g (1.22 mmol; 3 mol %) of tris(dibenzylideneacetone)dipalladium [CAS 51364-51-3], and the reaction mixture is heated under reflux for 16 h. The reaction mixture is cooled down to room temperature and the solvent is removed under reduced pressure. The solids obtained are washed with 300 ml of ethanol and the recrystallized repeatedly for a mixture of heptane and xylene. After a hot filtration through Alox followed by sublimation under high vacuum, the purified product is obtained as a colourless solid, 21.1 g (29.5 mmol; 69%).

[0304] In an analogous manner, it is possible to obtain the following compounds:

TABLE-US-00010 No. Reactant 1 Reactant 2 1b [01892] [01893] SoA [01894] [01895] 2b [01896] [01897] 3b [01898] [01899] 4b [01900] [01901] 5b [01902] [01903] 6b [01904] [01905] 7b [01906] [01907] 8b [01908] [01909] 9b [01910] [01911] 10b [01912] [01913] 11b [01914] [01915] 12b [01916] [01917] 13b [01918] [01919] 14b [01920] [01921] 15b [01922] [01923] 16b [01924] [01925] 17b [01926] [01927] 18b [01928] [01929] 19b [01930] [01931] 20b [01932] [01933] 21b [01934] [01935] 22b [01936] [01937] 23b [01938] [01939] 24b [01940] [01941] 25b [01942] [01943] 26b [01944] [01945] 27b [01946] [01947] 28b [01948] [01949] 29b [01950] [01951] 30b [01952] [01953] 31b [01954] [01955] 32b [01956] [01957] 33b [01958] [01959] 34b [01960] [01961] 35b [01962] [01963] 36b [01964] [01965] 37b [01966] [01967] 38b [01968] [01969] 39b [01970] [01971] 40b [01972] [01973] 41b [01974] [01975] 42b [01976] [01977] 43b [01978] [01979] 44b [01980] [01981] No. Product Yield 1b [01982] 83% SoA [01983] 73% 2b [01984] 81% 3b [01985] 77% 4b [01986] 80% 5b [01987] 47% 6b [01988] 70% 7b [01989] 61% 8b [01990] 65% 9b [01991] 84% 10b [01992] 81% 11b [01993] 72% 12b [01994] 88% 13b [01995] 62% 14b [01996] 68% 15b [01997] 58% 16b [01998] 61% 17b [01999] 70% 18b [02000] 67% 19b [02001] 72% 20b [02002] 71% 21b [02003] 72% 22b [02004] 65% 23b [02005] 66% 24b [02006] 83% 25b [02007] 80% 26b [02008] 52% 27b [02009] 71% 28b [02010] 68% 29b [02011] 65% 30b [02012] 63% 31b [02013] 72% 32b [02014] 59% 33b [02015] 56% 34b [02016] 60% 35b [02017] 69% 36b [02018] 63% 37b [02019] 66% 38b [02020] 70% 39b [02021] 61% 40b [02022] 77% 41b [02023] 70% 42b [02024] 52% 43b [02025] 46% 44b [02026] 55%