Organic electroluminescent devices comprising host compounds

Abstract

The present invention relates to an organic electroluminescent device comprising a light-emitting layer B containing at least one host compound H of Formula (I) ##STR00001##
wherein each of X′.sub.1 and X′.sub.2 is independently from another selected from the group consisting of nitrogen and an optionally substituted carbon atom, and wherein at least one of R′.sub.1—R′.sub.10 is CN and at least one of R.sub.A—R.sub.E is a substituted silane residue.

Claims

1. An organic compound H of Formula (I): ##STR00049## wherein: each of X′.sub.1 and X′.sub.2 is independently from another selected from the group consisting of N and CR.sup.Tz; R.sup.Tz is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, CN, CF.sub.3, C.sub.1-C.sub.20-alkyl, C.sub.6-C.sub.18-aryl, and C.sub.7-C.sub.19-alkaryl and, wherein C.sub.6-C.sub.18-aryl or C.sub.7-C.sub.19-alkaryl can at each occurrence be optionally substituted by a residue selected from the group consisting of C.sub.1-C.sub.20-alkyl, C.sub.7-C.sub.19-alkaryl, and C.sub.6-C.sub.18-aryl; R′.sub.1, R′.sub.2, R′.sub.3, R′.sub.4, R′.sub.5, R′.sub.6, R′.sub.7, R′.sub.8, R′.sub.9, and R′.sub.10 is independently from another selected from the group consisting of hydrogen, deuterium, CN, CF.sub.3, C.sub.1-C.sub.20-alkyl, C.sub.6-C.sub.18-aryl, C.sub.7-C.sub.19-alkaryl, and —SiR.sub.FR.sub.GR.sub.H, wherein C.sub.6-C.sub.18-aryl or C.sub.7-C.sub.19-alkaryl can at each occurrence be optionally substituted by a residue selected from the group consisting of C.sub.1-C.sub.20-alkyl, C.sub.7-C.sub.19-alkaryl, and C.sub.6-C.sub.18-aryl; wherein at least one selected from the group consisting of R′.sub.1, R′.sub.2, R′.sub.3, R′.sub.4, R′.sub.5, R′.sub.6, R′.sub.7, R′.sub.8, R′.sub.9, and R′.sub.10 is CN; each of R.sub.F, R.sub.G and R.sub.H is selected from the group consisting of unsubstituted or substituted C.sub.6-C.sub.18-aryl, C.sub.1-C.sub.20-alkyl, C.sub.7-C.sub.19-alkaryl, C.sub.1-C.sub.20-heteroalkyl and C.sub.3-C.sub.17-heteroaryl; R.sub.A, R.sub.B, R.sub.C, R.sub.D, and R.sub.E, is independently from another selected from the group consisting of hydrogen, deuterium, CN, CF.sub.3, C.sub.1-C.sub.20-alkyl, C.sub.6-C.sub.18-aryl, C.sub.7-C.sub.19-alkaryl, and —SiR.sub.KR.sub.MR.sub.N, wherein C.sub.6-C.sub.18-aryl or C.sub.7-C.sub.19-alkaryl can at each occurrence be optionally substituted by a residue selected from the group consisting of C.sub.1-C.sub.20-alkyl, C.sub.7-C.sub.19-alkaryl, and C.sub.6-C.sub.18-aryl; each of R.sub.K, R.sub.M, and R.sub.N is selected from the group consisting of unsubstituted or substituted C.sub.6-C.sub.18-aryl, C.sub.1-C.sub.20-alkyl, C.sub.7-C.sub.19-alkaryl, C.sub.1-C.sub.20-heteroalkyl and C.sub.3-C.sub.17-heteroaryl; wherein at least one selected from the group consisting of R.sub.A, R.sub.B, R.sub.C, R.sub.D and R.sub.E is —SiR.sub.KR.sub.MR.sub.N.

2. The organic compound H according to claim 1, wherein at least one selected from the group consisting of X′.sub.1 and X′.sub.2 is N.

3. The organic compound H according to claim 1, wherein exactly one of R.sub.A, R.sub.B, R.sub.C, R.sub.D and R.sub.E is —SiR.sub.KR.sub.MR.sub.N.

4. The organic compound H according to claim 1, wherein R.sub.B is —SiR.sub.KR.sub.MR.sub.N and R.sub.A, R.sub.C, R.sub.D and R.sub.E are each hydrogen.

5. The organic compound H according to claim 1, wherein the organic compound H has a structure of the following Formula (II): ##STR00050## wherein R′.sub.1, R′.sub.2, R′.sub.3, R′.sub.4, R′.sub.5, R′.sub.6, R′.sub.7, R′.sub.8, R′.sub.9, and R′.sup.10 are defined as in claim 1.

6. The organic compound H according to claim 1, wherein no more than two of R′.sub.1, R′.sub.2, R′.sub.3, R′.sub.4, R′.sub.5, R′.sub.6, R′.sub.7, R′.sub.8, R′.sub.9, and R′.sub.10 are CN.

7. The organic compound H according to claim 1, wherein exactly one of R′.sub.1, R′.sub.2, R′.sub.3, R′.sub.4, R′.sub.5, R′.sub.6, R′.sub.7, R′.sub.8, R′.sub.9, and R′.sub.10 is CN and the remaining residues selected from R′.sub.1, R′.sub.2, R′.sub.3, R′.sub.4, R′.sub.5, R′.sub.6, R′.sub.7, R′.sub.8, R′.sub.9, and R′.sub.10 are each hydrogen.

8. The organic compound H according to claim 1, wherein R′.sub.2 is CN and R′.sub.1, R′.sub.3, R′.sub.4, R′.sub.5, R′.sub.6, R′.sub.7, R′.sub.8, R′.sub.9, and R′.sub.10 are each hydrogen.

9. An organic electroluminescent device comprising a light-emitting layer B containing at least one organic compound H according to claim 1 as host.

10. The organic electroluminescent device according to claim 9, wherein said organic electroluminescent device is a device selected from the group consisting of an organic light emitting diode, a light emitting electrochemical cell, and a light-emitting transistor.

11. The organic electroluminescent device according to claim 9, wherein the light-emitting layer B comprises: (i) 5-99% by weightof at least one host compound H according to claim 1; (ii) 1-50% by weight of at least one emitter compound E; and optionally (iii) 0-94% by weight of at least one further host compound D not according to Formula (I); and optionally (iv) 0-10% by weight of at least one further emitter compound F not according to Formula (I); and optionally (v) 0-94% by weight of a solvent.

12. The organic electroluminescent device according to claim 11, wherein the at least one emitter compound E is a TADF compound E.sup.TADF.

13. The organic electroluminescent device according to claim 9, wherein the light-emitting layer B comprises: (i) 5-99% by weight of at least one host compound H according to claim 1; (ii) 0.1-10% by weight of at least one NRCT emitter compound E.sup.NRCT; and (iiia) 0.9-94.9% by weight of at least one further host compound D not according to Formula (I); or (iiib) 0.9-94.9% by weight of at least one TADF compound E.sup.TADF not according to Formula (I); and optionally (iv) 0-94% by weight of a solvent.

14. The organic electroluminescent device according to claim 9 further comprising at least one further host compound D, wherein the organic compound H has a lowest unoccupied molecule orbital LUMO(H) having an energy E.sup.LUMO(H) and the at least one further host compound D has a lowest unoccupied molecule orbital LUMO(D) having an energy E.sup.LUMO(D), wherein E.sup.LUMO(H)<E.sup.LUMO(D).

15. The organic electroluminescent device according to claim 12, wherein the TADF emitter compound E.sup.TADF consists of a structure according to Formula (Is): ##STR00051## wherein n is at each occurrence independently from another 1 or 2; X.sup.s is SiPh.sub.3, CN or CF.sub.3; Ar.sup.EWG is at each occurrence independently from another a structure according to one of Formulas IIsa to IIsm ##STR00052## ##STR00053## Formula IIsm wherein #.sup.s represents the binding site of the single bond linking Ar.sup.EWG to the substituted central phenyl ring of Formula 1s; R.sup.t is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, C.sub.1-C.sub.5-alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium, and C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more substituents R.sup.6s; R.sup.s is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, N(R.sup.5s).sub.2, OR.sup.5s, SR.sup.5s, Si(R.sup.5s).sub.3, CF.sub.3, CN, F, C.sub.1-C.sub.40-alkyl which is optionally substituted with one or more substituents R.sup.5s and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5sC═CR.sup.5s, C≡C, Si(R.sup.5s).sub.2, Ge(R.sup.5s).sub.2, Sn(R.sup.5s).sub.2, C═O, C═S, C═Se, C═NR.sup.5s, P(═O)(R.sup.5s), SO, SO.sub.2, NR.sup.5s, O, S or CONR.sup.5s; C.sub.1-C.sub.40-thioalkoxy which is optionally substituted with one or more substituents RSS and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5sC═CR.sup.5s, C≡C, Si(R.sup.5s).sub.2, Ge(R.sup.5s).sub.2, Sn(R.sup.5s).sub.2, C═O, C═S, C═Se, C═NR.sup.5s, P(═O)(R.sup.5s), SO, SO.sub.2, NR.sup.5s, O, S or CONR.sup.5s; and C.sub.6-C.sub.60-aryl which is optionally substituted with one or more substituents R.sup.5s; C.sub.3-C.sub.57-heteroaryl which is optionally substituted with one or more substituents R.sup.5s; R.sup.5s is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, N(R.sup.6s).sub.2, OR.sup.6s, SR.sup.6s, Si(R.sup.6s).sub.3, CF.sub.3, CN, F, C.sub.1-C.sub.40-alkyl which is optionally substituted with one or more substituents R.sup.6s and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.6sC═CR.sup.6s, C≡C, Si(R.sup.6s).sub.2, Ge(R.sup.6s).sub.2, Sn(R.sup.6S).sub.2, C═O, C═S, C═Se, C═NR.sup.6s, P(═O)(R.sup.6s), SO, SO.sub.2, NR.sup.6s, O, S or CONR.sup.6s, C.sub.6-C.sub.60-aryl which is optionally substituted with one or more substituents R.sup.6s; and C.sub.3-C.sub.57-heteroaryl which is optionally substituted with one or more substituents R.sup.6s; R.sup.6s is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, OPh, CF.sub.3, CN, F, C.sub.1-C.sub.5-alkyl, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-alkoxy, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-thioalkoxy, wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.6-C.sub.18-aryl which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents; C.sub.3-C.sub.17-heteroaryl which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents; N(C.sub.6-C.sub.18-aryl).sub.2, N(C.sub.3-C.sub.17-heteroaryl).sub.2, and N(C.sub.3-C.sub.17-heteroaryl)(C.sub.6-C.sub.18-aryl); R.sup.d is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, N(R.sup.5s).sub.2, OR.sup.5s, SR.sup.5s, Si(R.sup.5s).sub.3, CF.sub.3, CN, F, C.sub.1-C.sub.40-alkyl which is optionally substituted with one or more substituents R.sup.5s and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5sC═CR.sup.5s, C≡C, Si(R.sup.5s).sub.2, Ge(R.sup.5s).sub.2, Sn(R.sup.5s).sub.2, C═O, C═S, C═Se, C═NR.sup.5s, P(═O)(R.sup.5s), SO, SO.sub.2, NR.sup.5s, O, S or CONR.sup.5s; C.sub.1-C.sub.40-thioalkoxy which is optionally substituted with one or more substituents R.sup.5s and wherein one or more non-adjacent CH.sub.2-groups are optionally substituted by R.sup.5sC═CR.sup.5s, C≡C, Si(R.sup.5s).sub.2, Ge(R.sup.5s).sub.2, Sn(R.sup.5s).sub.2, C═O, C═S, C═Se, C=NR.sup.5s, P(═O)(R.sup.5s), SO, SO.sub.2, NR.sup.5s, O, S or CONR.sup.5s; and C.sub.6-C.sub.60-aryl which is optionally substituted with one or more substituents R.sup.5s; C.sub.3-C.sub.57-heteroaryl which is optionally substituted with one or more substituents R.sup.5s; wherein the substituents R.sup.s, or R.sup.5s independently from each other optionally may form a mono- or polycyclic, (hetero)aliphatic, (hetero)aromatic and/or benzo-fused ring system with one or more substituents R.sup.s or R.sup.5s and wherein the one or more substituents R.sup.d independently from each other optionally may form a mono- or polycyclic, (hetero)aliphatic, (hetero)aromatic and/or benzo-fused ring system with one or more substituents R.sup.d.

16. The organic electroluminescent device according to claim 15, wherein n=2 and X.sup.s is CN.

17. The organic electroluminescent device according to claim 15, wherein R.sup.s is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3 and Ph; pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3 and Ph; pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3 and Ph; carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3 and Ph; triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, .sup.iPr, .sup.tBu, CN, CF.sub.3 and Ph; and N(Ph).sub.2.

18. The organic electroluminescent device according to claim 13, wherein the NRCT emitter compound E.sup.NRCT consists of a structure according to Formula (In): ##STR00054## wherein n.sup.n is 0 or 1; m=1−n.sup.n; X.sup.1 is N or B; X.sup.2 is N or B; X.sup.3 is N or B; W is selected from the group consisting of Si(R.sup.3).sub.2, C(R.sup.3).sub.2 and BR.sup.3; each of R.sup.1, R.sup.2 and R.sup.3 is independently from each other selected from the group consisting of: C.sub.1-C.sub.5-alkyl, which is optionally substituted with one or more substituents R.sup.6; C.sub.6-C60-aryl, which is optionally substituted with one or more substituents R.sup.6; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.6; each of R.sup.I, R.sup.II, R.sup.III, R.sup.IV, R.sup.V, R.sup.VI, R.sup.VII, R.sup.VIII, R.sup.IX, R.sup.X, and R.sup.XI independently from another selected from the group consisting of: hydrogen, deuterium, N(R.sup.5).sub.2, OR.sup.5, Si(R.sup.5).sub.3, B(OR.sup.5).sub.2, OSO.sub.2R.sup.5, CF.sub.3, CN, halogen, C.sub.1-C.sub.40-alkyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are each optionally substituted by R.sup.5C═CR.sup.5, C≡C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5, C.sub.1-C.sub.40-alkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are each optionally substituted by R.sup.5C═CR.sup.5, C≡C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.1-C.sub.40-thioalkoxy, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are each optionally substituted by R.sup.5C═CR.sup.5, C≡C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkenyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are each optionally substituted by R.sup.5C═CR.sup.5, C≡C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.2-C.sub.40-alkynyl, which is optionally substituted with one or more substituents R.sup.5 and wherein one or more non-adjacent CH.sub.2-groups are each optionally substituted by R.sup.5C═CR.sup.5, C≡C, Si(R.sup.5).sub.2, Ge(R.sup.5).sub.2, Sn(R.sup.5).sub.2, C═O, C═S, C═Se, C═NR.sup.5, P(═O)(R.sup.5), SO, SO.sub.2, NR.sup.5, O, S or CONR.sup.5; C.sub.6-C.sub.60-aryl, which is optionally substituted with one or more substituents R.sup.5; and C.sub.3-C.sub.57-heteroaryl, which is optionally substituted with one or more substituents R.sup.5; R.sup.5 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, OPh, CF.sub.3, CN, F, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-alkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-thioalkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkenyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkynyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents; C.sub.3-C.sub.17-heteroaryl, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents; N(C.sub.6-C.sub.18-aryl).sub.2, N(C.sub.3-C.sub.17-heteroaryl).sub.2; and N(C.sub.3-C.sub.17-heteroaryl)(C.sub.6-C.sub.18-aryl); R.sup.6 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, OPh, CF.sub.3, CN, F, C.sub.1-C.sub.5-alkyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-alkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.1-C.sub.5-thioalkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkenyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.2-C.sub.5-alkynyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF.sub.3, or F; C.sub.6-C.sub.18-aryl, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents; C.sub.3-C.sub.17-heteroaryl, which is optionally substituted with one or more C.sub.1-C.sub.5-alkyl substituents; N(C.sub.6-C.sub.18-aryl).sub.2, N(C.sub.3-C.sub.17-heteroaryl).sub.2; and N(C.sub.3-C.sub.17-heteroaryl)(C.sub.6-C.sub.18-aryl); wherein two or more of the substituents selected from the group consisting of R.sup.I, R.sup.II, R.sup.III, R.sup.IV, R.sup.V, R.sup.VI, R.sup.VII, R.sup.VIII, R.sup.IX, R.sup.X, and R.sup.XI that are positioned adjacent to another may each optionally form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with another; and wherein at least one selected from the group consisting of X.sup.1, X.sup.2 and X.sup.3 is B and at least one selected from the group consisting of X.sup.1, X.sup.2 and X.sup.3 is N.

19. The organic electroluminescent device according to claim 18, wherein X.sup.1, and X.sup.3 each are N and X.sup.2 is B and n.sup.n=0.

20. The organic compound H according to claim 1, wherein both of X′.sub.1 and X′.sub.2 are each N.

21. The organic compound H according to claim 1, wherein exactly one of R.sub.A, R.sub.B, R.sub.C, R.sub.D and R.sub.E is —SiR.sub.KR.sub.MR.sub.N and the remaining residues selected from R.sub.A, R.sub.B, R.sub.C, R.sub.D and R.sub.E are each hydrogen.

Description

EXAMPLES

(1) Cyclic Voltammetry

(2) Cyclic voltammograms of solutions having concentration of 10.sup.−3 mol/l of the organic molecules in dichloromethane or a suitable solvent and a suitable supporting electrolyte (e.g. 0.1 mol/l of tetrabutylammonium hexafluorophosphate) are measured. The measurements are conducted at room temperature and under nitrogen atmosphere with a three-electrode assembly (Working and counter electrodes: Pt wire, reference electrode: Pt wire) and calibrated using FeCp.sub.2/FeCp.sub.2.sup.+ as internal standard. HOMO data was corrected using ferrocene as internal standard against SCE.

(3) Density Functional Theory Calculation

(4) Molecular structures are optimized employing the BP86 functional and the resolution of identity approach (RI). Excitation energies are calculated using the (BP86) optimized structures employing Time-Dependent DFT (TD-DFT) methods. Orbital and excited state energies are calculated with the B3LYP functional. Def2-SVP basis sets and a m4-grid for numerical integration were used. The Turbomole program package was used for all calculations.

(5) Photophysical Measurements

(6) Sample Pretreatment: Spin-Coating

(7) Apparatus: Spin150, SPS euro.

(8) The sample concentration is 10 mg/ml, dissolved in a suitable solvent.

(9) Program: 1) 3 s at 400 U/min, 20 s at 1000 U/min at 1000 Upm/s. 3) 10 s at 4000 U/min at 1000 Upm/s. After coating, the films are tried at 70° C. for 1 min.

(10) Photoluminescence Spectroscopy and TCSPC (Time-Correlated Single-Photon Counting)

(11) Steady-state emission spectroscopy is recorded using a Horiba Scientific, Modell FluoroMax-4 equipped with a 150 W Xenon-Arc lamp, excitation- and emissions monochromators and a Hamamatsu R928 photomultiplier and a time-correlated single-photon counting option. Emissions and excitation spectra are corrected using standard correction fits.

(12) Excited state lifetimes are determined employing the same system using the TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.

(13) Excitation Sources:

(14) NanoLED 370 (wavelength: 371 nm, puls duration: 1,1 ns)

(15) NanoLED 290 (wavelength: 294 nm, puls duration: <1 ns)

(16) SpectraLED 310 (wavelength: 314 nm)

(17) SpectraLED 355 (wavelength: 355 nm).

(18) Data analysis (exponential fit) was done using the software suite DataStation and DAS6 analysis software. The fit is specified using the chi-squared-test.

(19) Photoluminescence Quantum Yield Measurements

(20) For photoluminescence quantum yield (PLQY) measurements an Absolute PL Quantum Yield Measurement C9920-03G system (Hamamatsu Photonics) is used. Quantum yields and CIE coordinates were determined using the software U6039-05 version 3.6.0.

(21) Emission maxima are given in nm, quantum yields Φ in % and CIE coordinates as x,y values.

(22) PLQY was determined using the following protocol: 1) Quality assurance: Anthracene in ethanol (known concentration) is used as reference 2) Excitation wavelength: the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength 3) Measurement Quantum yields are measured for sample of solutions or films under nitrogen atmosphere. The yield is calculated using the equation:

(23) ${\Phi }_{\mathrm{PL}}=\frac{n_{\mathrm{photon}},\mathrm{emited}}{n_{\mathrm{photon}},\mathrm{absorbed}}=\frac{\int \frac{\lambda }{\mathrm{hc}}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{sample}}\left(\lambda \right)-{\mathrm{Int}}_{\mathrm{absorbed}}^{\mathrm{sample}}\left(\lambda \right)\right]d\lambda }{\int \frac{\lambda }{\mathrm{hc}}\left[{\mathrm{Int}}_{\mathrm{emitted}}^{\mathrm{reference}}\left(\lambda \right)-{\mathrm{Int}}_{\mathrm{absorbed}}^{\mathrm{reference}}\left(\lambda \right)\right]d\lambda }$ wherein n.sub.photon denotes the photon count and Int. is the intensity.

(24) Production and Characterization of Organic Electroluminescence Devices

(25) Via vacuum-deposition methods OLED devices comprising organic molecules according to the invention can be produced. If a layer contains more than one compound, the weight-percentage of one or more compounds is given in %. The total weight-percentage values amount to 100%, thus if a value is not given, the fraction of this compound equals to the difference between the given values and 100%.

(26) The not fully optimized OLEDs are characterized using standard methods and measuring electroluminescence spectra, the external quantum efficiency (in %) in dependency on the intensity, calculated using the light detected by the photodiode, and the current. The OLED device lifetime is extracted from the change of the luminance during operation at constant current density. The LT50 value corresponds to the time, where the measured luminance decreased to 50% of the initial luminance, analogously LT80 corresponds to the time point, at which the measured luminance decreased to 80% of the initial luminance, LT97 to the time point, at which the measured luminance decreased to 97% of the initial luminance etc.

(27) Accelerated lifetime measurements are performed (e.g. applying increased current densities). Exemplarily LT80 values at 500 cd/m.sup.2 are determined using the following equation:

(28) $\mathrm{LT}80\left(500\frac{{\mathrm{cd}}^2}{m^2}\right)=\mathrm{LT}80\left(L_0\right){\left(\frac{L_0}{500\frac{{\mathrm{cd}}^2}{m^2}}\right)}^{1.6}$
wherein L.sub.0 denotes the initial luminance at the applied current density.

(29) The values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels is given. Figures show the data series for one OLED pixel.

(30) Generalized Synthetic Route:

(31) ##STR00039## ##STR00040##

(32) Generalized Synthesis AAV0:

(33) ##STR00041##

(34) E0 (1.00 equivalents), in which Hal preferably represents Cl, E1 (1.00 equivalents), Tetrakis(triphenylphosphine)palladium(0) (0.05 equivalents), and potassium carbonate (1.50 equivalents) are stirred under nitrogen atmosphere in a tetrahydrofuran (THF)/water mixture (ratio of 4:1) at 65° C. for 16 h. After cooling down to room temperature (rt), the mixture is extracted between toluene and water and washed with brine. The combined organic layers are dried over MgSO4, filtered and the solvent is removed under reduced pressure. The solid crude product E2 is purified by chromatography.

(35) Generalized Synthesis AAV1:

(36) ##STR00042##

(37) E2 (1.00 equivalents), in which Hal preferably represents Cl, E3 (1.20 equivalents), Tetrakis(triphenylphosphine)palladium(0) (0.05 equivalents), and potassium carbonate (1.50 equivalents) are stirred under nitrogen atmosphere in a tetrahydrofuran (THF)/water mixture (ratio of 10:1) at 80° C. for 16 h. After cooling down to room temperature (rt), the solvent is removed under reduced pressure. The mixture is extracted between dichloromethane (DCM) and water and washed with brine. The combined organic layers are dried over MgSO4, filtered and the solvent is removed under reduced pressure. The solid product is purified by chromatography.

(38) In synthesis AAV0: and AAV1, a boronic acid ester, such as boronic acid pinacol ester, can be employed instead of the respective boronic acid group. In addition, different palladium catalysts may be employed. The skilled artesian is able to adapt solvents mixtures and reaction conditions to the used reactants and catalysts.

(39) Synthesis of Compound 1

(40) 2,4-Dichloro-6-phenyl-1,3,5-triazine (CAS: 1700-02-3) was used as E1, and 3-cyanophenylboronic acid (CAS: 150255-96-2) is used as E2 to yield the intermediate Z1 (yield: 5%) according to AAVO. Z1 was then reacted with 3-(triphenylsilyl)phenylboronic acid (CAS: 1253912-58-1) according to AAV1 to yield Compound 1 (yield: 46%).

(41) LC-MS: calculatedd for C40H28N4Si 592.77, found 593.33 (10.91 min)

(42) ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047##

Device Examples

(43) Compound 1 was tested in OLED devices (Devices D1, D2, and D3) and compared to Comparison Compound CC1 (Device C1) with the layer structure given in the following Table 1.

(44) TABLE-US-00001 TABLE 1 Design of Devices D1, D2 and C1 Layer thickness D1 D2 C1 10 100 nm  Al Al Al 9  2 nm Liq Liq Liq 8 20 nm NBPhen NBPhen NBPhen 7 10 nm NBPhen 1 NBPhen 6 50 nm mCBP mCBP mCBP (70%) (70%) (70%) 1 (20%) 1 (20%) CC1 (20%) El (10%) El (10%) El (10%) 5 10 nm mCBP mCBP mCBP 4 10 nm TCTA TCTA TCTA 3 40 nm NPB NPB NPB 2  5 nm HAT-CN HAT-CN HAT-CN 1 50 nm ITO ITO ITO substrate glass glass glass D1: The emission maximum is determined at 475 nm at 6 V. The turn on voltage is 2.05 V. The EQE at 1000 cd/m.sup.2 is 13.8%. D2: The emission maximum is determined at 474 nm at 6 V. The turn on voltage is 2.05 V. The EQE at 1000 cd/m.sup.2 is 16.8%. C1: The emission maximum is determined at 474 nm at 6 V. The turn on voltage is 2.35 V. The EQE at 1000 cd/m.sup.2 is 12.3%. As can be seen from the experiments, by using at least one organic compound H in an emitting layer B of an organic electroluminescent device the turn on voltage can be beneficially decreased and the EQE is beneficially increased in comparison to using Comparison Compound CC1 in an emitting layer B of an organic electroluminescent device.

(45) ##STR00048##