ORGANIC MOLECULES FOR OPTOELECTRONIC DEVICES

Abstract

The invention relates to an organic molecule, in particular for the application in optoelectronic devices. According to the invention, the organic molecule has a structure of formula I:

##STR00001##

wherein R.sup.I, R.sup.II, R.sup.III and R.sup.IV are independently from another selected from the group consisting of: hydrogen, deuterium, N(R.sup.5).sub.2, OR.sup.5, SR.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, C.sub.1-C.sub.40-alkoxy, C.sub.1-C.sub.40-thioalkoxy, C.sub.2-C.sub.40-alkenyl, C.sub.2-C.sub.40-alkynyl, C.sub.6-C.sub.60-aryl, and C.sub.3-C.sub.57-heteroaryl, and R.sup.V is selected from the group of C.sub.1-C.sub.5 alkyl, C.sub.6-C.sub.18 aryl, and C.sub.3-C.sub.15 heteroaryl.

Claims

1. An organic molecule, comprising a structure of Formula I: ##STR00091## wherein each of R.sup.I, R.sup.II, R.sup.III and R.sup.IV is independently selected from the group consisting of: hydrogen, deuterium, N(R.sup.5).sub.2, OR.sup.5, SR.sup.5, Si(R.sup.5).sub.3, B(OR.sup.5).sub.2, R.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 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 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 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 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 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 selected from the group consisting of: hydrogen, deuterium, OPh, SPh, CF.sub.3, CN, F, Si(C.sub.1-C.sub.5-alkyl).sub.3, Si(Ph).sub.3, 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); R.sup.V is at each occurrence independently selected from the group consisting of: C.sub.1-C.sub.5-alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium; R.sup.VI, R.sup.VII and R.sup.VIII are at each occurrence independently 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; C.sub.6-C.sub.18-aryl, wherein optionally one or more hydrogen atoms are independently from each other substituted by C.sub.1-C.sub.5-alkyl, C.sub.6-C.sub.18 aryl or C.sub.3-C.sub.17-heteroaryl; C.sub.3-C.sub.15-heteroaryl, wherein optionally one or more hydrogen atoms are independently from each other substituted by C.sub.1-C.sub.5-alkyl, C.sub.6-C.sub.18 aryl or C.sub.3-C.sub.17-heteroaryl.

2. The organic molecule according to claim 1, wherein R.sup.I, R.sup.II, R.sup.III and R.sup.IV are independently from each other selected from the group consisting of: hydrogen, deuterium, halogen, Me, .sup.iPr, .sup.tBu, CN, CF.sub.3, SiMe.sub.3, SiPh.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.

3. The organic molecule according to claim 1, wherein each of R.sup.I, R.sup.II, R.sup.III and R.sup.IV is independently selected from the group consisting of: hydrogen, deuterium, Me, .sup.iPr, .sup.tBu, SiMe.sub.3, SiPh.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, and Ph, and N(Ph).sub.2.

4. The organic molecule according to claim 1, wherein the organic molecule comprises a structure of Formula Ia: ##STR00092##

5. The organic molecule according to claim 1, wherein R.sup.II is equal to R.sup.III.

6. The organic molecule according to claim 1, wherein R.sup.V is methyl (Me), wherein one or more hydrogen atoms are optionally substituted by deuterium.

7. The organic molecule according to claim 1, wherein R.sup.VI, R.sup.VII and R.sup.VIII are at each occurrence independently from each other selected from the group consisting of hydrogen, C.sub.1-C.sub.5-alkyl, and C.sub.6-C.sub.18-aryl, wherein optionally one or more hydrogen atoms are independently from each other substituted by C.sub.1-C.sub.5-alkyl or C.sub.6-C.sub.18-aryl.

8. The organic molecule according to claim 1, wherein the organic molecule comprises a structure of Formula I-0: ##STR00093##

9. The organic molecule according to claim 1, wherein the organic molecule comprises a structure of Formula Ic: ##STR00094##

10. (canceled)

11. (canceled)

12. A composition, comprising: (a) an organic molecule according to claim 1 as an emitter and/or a host; (b) an emitter and/or a host material different from the organic molecule according to claim 1; and (c) optionally, a dye and/or a solvent.

13. (canceled)

14. (canceled)

15. (canceled)

16. An optoelectronic device comprising the organic molecule according to claim 1.

17. The optoelectronic device according to claim 16, wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

18. The optoelectronic device according to claim 16, comprising: a substrate; an anode; a cathode, wherein the anode or the cathode is disposed on the substrate; and at least one light-emitting layer disposed between the anode and the cathode and which comprises the organic molecule.

19. An optoelectronic device comprising the organic molecule according to claim 1, wherein the organic molecule is one of a luminescent emitter, an electron transport material, a hole injection material or a hole blocking material in the optoelectronic device.

20. An optoelectronic device comprising the organic molecule according to claim 2, wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

21. The optoelectronic device according to claim 20, comprising: a substrate; an anode; a cathode, wherein the anode or the cathode is applied to the substrate; and at least one light-emitting layer disposed between the anode and the cathode and which comprises the organic molecule.

22. An optoelectronic device comprising the composition according to claim 12.

23. The optoelectronic device according to claim 22, wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

24. The optoelectronic device according to claim 22, comprising: a substrate; an anode; a cathode, wherein the anode or the cathode is disposed on the substrate; and at least one light-emitting layer disposed between the anode and the cathode and which comprises the composition.

25. A method for producing an optoelectronic device, comprising processing of the organic molecule according to claim 1 by a vacuum evaporation method or from a solution.

Description

EXAMPLES

[0629] ##STR00032## ##STR00033## ##STR00034##

[0630] General Procedure for Synthesis AAV1:

##STR00035##

[0631] 1,3-Dibromo-2,5-dichlorbenzene (CAS: 81067-41-6, 1.00 equivalents), E1 (2.20 equivalents), tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.02 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (P(.sup.tBu).sub.3, CAS: 13716-12-6, 0.08 equivalents) and sodium tert-butoxide (NaO.sup.tBu; 6.00 equivalents) are stirred under nitrogen atmosphere in toluene at 80° C. for 2 h. After cooling down to room temperature (rt) the reaction mixture is extracted with toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I1 is obtained as solid.

[0632] General Procedure for Synthesis AAV2:

##STR00036##

[0633] I1 (1.00 equivalents), E2 (2.20 equivalents, tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.02 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (0.08 equivalents, P(.sup.tBu).sub.3, CAS: 13716-12-6) and sodium tert-butoxide (NaO.sup.tBu; 5.00 equivalents) are stirred under nitrogen atmosphere in toluene at 100° C. for 5 h. After cooling down to room temperature (rt) the reaction mixture is extracted with toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I2 is obtained as solid.

[0634] General Procedure for Synthesis AAV3:

##STR00037##

[0635] After dissolving I2 (1 equivalent) under nitrogen atmosphere in THF and cooling to −20° C. or in tert-butylbenzene and cooling to −10° C., .sup.tBuLi (2 equivalents, CAS: 594-19-4) is added and the reaction mixture is stirred at 0° C. After complete lithiation, 1,3,2-dioxaborolane (2 equivalents, CAS: 61676-62-8) is added and the reaction mixture is stirred under reflux at 70° C. for 2 h. After cooling down to room temperature (rt), the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I3 is obtained as solid.

[0636] General Procedure for Synthesis AAV3-a:

##STR00038##

[0637] Under nitrogen atmosphere I2 (1 equivalent) is dissolved in tert-butylbenzene. At −10° C., .sup.tBuLi (2.2 equivalents, CAS: 594-19-4) is added and stirring continued at 0° C. After completion of the lithiation, at 0° C., trimethyl borate (6 equivalents, CAS: 121-43-7) is added and stirring continued at 20° C. for 2 h. After completion of the borylation, water is added and the resulting biphasic mixture vigorously stirred for 15 min. Subsequently, the phases are separated and the aqueous layer extracted with ethyl acetate. The combined organic layers are dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I3-a is obtained as solid.

[0638] General Procedure for Synthesis AAV4:

##STR00039##

[0639] I3 (1 equivalent), N,N-diisopropylethylamine (10 equivalents, CAS: 7087-68-5) and AlCl.sub.3 (10 equivalents, CAS: 7446-70-0) are stirred under nitrogen atmosphere in chlorobenzene at 120° C. for 16 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I4 is obtained as solid.

[0640] General Procedure for Synthesis AAV4-a:

##STR00040##

[0641] I3-a (1 equivalent), N,N-diisopropylethylamine (10 equivalents, CAS: 7087-68-5) and AlCl.sub.3 (10 equivalents, CAS: 7446-70-0) are stirred under nitrogen atmosphere in chlorobenzene at 120° C. for 2-4 h. After completion, the reaction is quenched by adding water at 0° C. Subsequently, the phases are separated and aqueous layer extracted with ethyl acetate. The combined organic layers are washed with water and brine, dried over MgSO.sub.4, filtered and subsequently concentrated under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I4 is obtained as solid.

[0642] General Procedure for Synthesis AAV5:

##STR00041##

[0643] I4 (1 equivalent), E3 (1.1 equivalents), palladium(II) acetate (CAS: 3375-31-3, 0.1 equivalents), S-Phos (CAS: 657408-07-6, 0.24 equivalents) and potassium phosphate tribasic (5 equivalents) are stirred under nitrogen atmosphere in dioxane/water 5:1 at 100° C. for 16 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and P1 is obtained as solid.

[0644] General Procedure for Synthesis AAV6:

##STR00042##

[0645] I4 (1 equivalent), bis(pinacolato)diboron (CAS: 73183-34-3, 1.5 equivalents), palladium(II) acetate (CAS: 3375-31-3, 0.1 equivalents), S-Phos (CAS: 657408-07-6, 0.2 equivalents,) and potassium phosphate tribasic (K.sub.3PO.sub.4; 5 equivalents) are stirred under nitrogen atmosphere in dioxane at 100° C. for 3 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I5 is obtained as solid.

[0646] General Procedure for Synthesis AAV7:

##STR00043##

[0647] I5 (1 equivalent), E4 (1.2 equivalents), palladium(II) acetate (CAS: 3375-31-3, 0.1 equivalents), S-Phos (CAS: 657408-07-6, 0.24 equivalents) and potassium phosphate tribasic (K.sub.3PO.sub.4; 5 equivalents) are stirred under nitrogen atmosphere in dioxane/water 10:1 at 100° C. for 16 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and P1 is obtained as solid.

##STR00044## ##STR00045## ##STR00046##

[0648] General Procedure for Synthesis AAV8:

##STR00047##

[0649] 1,3-Dibromo-2,5-dichlorbenzene (CAS: 81067-41-6, 1.00 equivalents), E5 (2.10 equivalents), tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.01 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (P(.sup.tBu).sub.3, CAS: 13716-12-6, 0.02 equivalents) and sodium tert-butoxide (NaO.sup.tBu; 3.00 equivalents) are stirred under nitrogen atmosphere in toluene at 80° C. for 8 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I2 is obtained as solid.

[0650] General Procedure for Synthesis AAV9:

##STR00048##

[0651] I2 (1 equivalent), bis(pinacolato)diboron (CAS: 73183-34-3, 1.5 equivalents), tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.1 equivalents; CAS: 51364-51-3), X-Phos (CAS: 564483-18-7, 0.2 equivalents,) and potassium acetate (4.00 equivalents) are stirred under nitrogen atmosphere in toluene at 95° C. for 16 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I6 is obtained as solid.

[0652] General Procedure for Synthesis AAV10:

##STR00049##

[0653] I6 (1.00 equivalents), E4 (1.50 equivalents), tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.04 equivalents; CAS: 51364-51-3), S-Phos (CAS: 657408-07-6, 0.08 equivalents) and potassium phosphate tribasic (K.sub.3PO.sub.4; 4.00 equivalents) are stirred under nitrogen atmosphere in DMSO at 110° C. for 16 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I7 is obtained as solid.

[0654] General Procedure for Synthesis AAV10-a:

##STR00050##

[0655] Under nitrogen atmosphere, I2 (1 equivalent), the boronic acid E3 (1.5 equivalents), tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.01 equivalents; CAS: 51364-51-3), X-Phos (CAS: 564483-18-7, 0.04 equivalents,) and tribasic potassium phosphate (3.00 equivalents) are stirred in toluene at 100° C. for 16 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I7 is obtained as solid.

[0656] General Procedure for the Synthesis AAV11:

##STR00051##

[0657] After dissolving I7 (1 equivalent) under nitrogen atmosphere in THF and cooling to −20° C. or in tert-butylbenzene and cooling to −10° C., .sup.tBuLi (2 equivalents, CAS: 594-19-4) is added and the reaction mixture is stirred at 0° C. After complete lithiation, 1,3,2-dioxaborolane (2 equivalents, CAS: 61676-62-8) is added and the reaction mixture is stirred under reflux at 70° C. for 2 h. After cooling down to room temperature (rt), the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I8 is obtained as solid.

[0658] General Procedure for Synthesis AAV11-a:

##STR00052##

[0659] Under nitrogen atmosphere I7 (1 equivalent) is dissolved in tert-butylbenzene. At −10° C., .sup.tBuLi (2.2 equivalents, CAS: 594-19-4) is added and stirring continued at 0° C. After completion of the lithiation, at 0° C., trimethyl borate (6 equivalents, CAS: 121-43-7) is added and stirring continued at 20° C. for 2 h. After completion of the borylation, water is added and the resulting biphasic mixture vigorously stirred for 15 min. Subsequently, the phases are separated and the aqueous layer extracted with ethyl acetate. The combined organic layers are dried over MgSO.sub.4, filtered and concentrated under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I8-a is obtained as solid.

[0660] General Procedure for the Synthesis AAV12:

##STR00053##

[0661] I8 (1 equivalent), N,N-diisopropylethylamine (10 equivalents, CAS: 7087-68-5) and AlCl.sub.3 (10 equivalents, CAS: 7446-70-0) are stirred under nitrogen atmosphere in chlorobenzene at 120° C. for 16 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and P1 is obtained as solid.

##STR00054##

[0662] General Procedure for Synthesis AAV13

##STR00055##

[0663] 1-Bromo-3,5-diphenylbenzene (1 equivalents, CAS: 103068-20-8), E1 (2.20 equivalents), tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.01 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (P(.sup.tBu).sub.3, CAS: 13716-12-6, 0.02 equivalents) and sodium tert-butoxide (NaO.sup.tBu; 3.00 equivalents) are stirred under nitrogen atmosphere in toluene at 80° C. for 5 h.

[0664] After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I4.1 is obtained as solid.

[0665] General Procedure for Synthesis AAV14:

##STR00056##

[0666] 1-Bromo-3,5-diphenylbenzene (1 equivalents, CAS: 103068-20-8), E1.1 (2.20 equivalents), tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.02 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine (P(.sup.tBu).sub.3, CAS: 13716-12-6, 0.02 equivalents) and sodium tert-butoxide (NaO.sup.tBu; 3.00 equivalents) are stirred under nitrogen atmosphere in toluene at 80° C. for 5 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I4.2 is obtained as solid.

[0667] General Procedure for Synthesis AAV15:

##STR00057##

[0668] E6 (1.00 equivalent), 14.1 (1.10 equivalents), tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.01 equivalents, CAS: 51364-51-3), tri-tert-butyl-phosphine P(.sup.tBu).sub.3 (0.02 equivalents, CAS: 13716-12-6) and sodium tert-butoxide NaO.sup.tBu (3.00 equivalents, CAS: 865-48-5) are stirred under nitrogen atmosphere in toluene at 80° C. for 5 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I9 is obtained as solid.

[0669] General Procedure for Synthesis AAV16:

##STR00058##

[0670] I4.2 (1.00 equivalent), 19 (1.10 equivalents), tris(dibenzylideneacetone)dipalladium Pd.sub.2(dba).sub.3 (0.01 equivalents; CAS: 51364-51-3), tri-tert-butyl-phosphine P(.sup.tBu).sub.3 (0.02 equivalents, CAS: 13716-12-6) and sodium tert-butoxide NaO.sup.tBu (3.00 equivalents, CAS: 865-48-5) are stirred under nitrogen atmosphere in toluene at 110° C. for 16 h. After cooling down to room temperature (rt) the reaction mixture is extracted between toluene and brine and the phases are separated. The combined organic layers are dried over MgSO.sub.4 and then the solvent is removed under reduced pressure. The crude product obtained is purified by recrystallization or column chromatography and I10 is obtained as solid.

[0671] The last synthesis steps of the general scheme III from 110 to P1 is carried out under similar conditions as described in AAV11 and AAV12 or AAV17.

[0672] General Procedure for Synthesis AAV17:

##STR00059##

[0673] I10 (1.00 equivalents) is dissolved in tert-butylbenzene under nitrogen atmosphere and the solution was cooled to −30° C. A solution of tert-butyllithium (.sup.tBuLi) (2.20 equivalents) was added dropwise and the reaction mixture was allowed to warm up to 0° C. After stirring for 120 minutes at 60° C., the solvent of the .sup.tBuLi-solution and byproducts are removed under reduced pressure and the reaction mixture was cooled again to −30° C. A solution of boron tribromide (BBr.sub.3, CAS: 10294-33-4, 2.00 equivalents) was added dropwise, the bath was removed and the reaction mixture was allowed to warm to room temperature (rt). After stirring for 30 minutes at rt, the reaction mixture was cooled to 0° C. and N,N-diisopropylethylamine (DIPEA, CAS: 7087-68-5, 3.00 equivalents) was added. The reaction mixture was allowed to warm to rt and then heated at reflux at 120° C. for 3 h. Subsequently, the reaction mixture was poured into water and the resulting precipitate was filtered and washed with a minimum amount of ethyl acetate to obtain P1 as a solid product. P1 can be further purified by recrystallization or by flash chromatography.

[0674] Cyclic Voltammetry

[0675] Cyclic voltammograms are measured from 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). The measurements are conducted at room temperature 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. The HOMO data was corrected using ferrocene as internal standard against a saturated calomel electrode (SCE).

[0676] Density Functional Theory Calculation

[0677] 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 are used. The Turbomole program package is used for all calculations.

[0678] Photophysical Measurements

[0679] Sample pretreatment: Spin-coating

[0680] Apparatus: Spin150, SPS euro.

[0681] The sample concentration is 10 mg/ml, dissolved in a suitable solvent.

[0682] 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 dried at 70° C. for 1 min.

[0683] Photoluminescence spectroscopy and Time-Correlated Single-Photon Counting (TCSPC) Steady-state emission spectroscopy is measured by 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.

[0684] Excited state lifetimes are determined employing the same system using the TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.

[0685] Excitation Sources:

[0686] NanoLED 370 (wavelength: 371 nm, puls duration: 1.1 ns)

[0687] NanoLED 290 (wavelength: 294 nm, puls duration: <1 ns)

[0688] SpectraLED 310 (wavelength: 314 nm)

[0689] SpectraLED 355 (wavelength: 355 nm).

[0690] Data analysis (exponential fit) is done using the software suite DataStation and DAS6 analysis software. The fit is specified using the chi-squared-test.

[0691] Photoluminescence Quantum Yield Measurements

[0692] For photoluminescence quantum yield (PLQY) measurements an Absolute PL Quantum Yield Measurement C9920-03G system (Hamamatsu Photonics) is used. Quantum yields and CIE coordinates are determined using the software U6039-05 version 3.6.0.

[0693] Emission maxima are given in nm, quantum yields ϕ in % and CIE coordinates as x,y values. PLQY is determined using the following protocol: [0694] 1) Quality assurance: Anthracene in ethanol (known concentration) is used as reference [0695] 2) Excitation wavelength: the absorption maximum of the organic molecule is determined and the molecule is excited using this wavelength [0696] 3) Measurement [0697] Quantum yields are measured, for sample, of solutions or films under nitrogen atmosphere. The yield is calculated using the equation:

[00001] $Φ_{PL} = \frac{n_{photon}, emited}{n_{photon}, absorbed} = \frac{\int \frac{λ}{hc} [{Int}_{emitted}^{sample} (λ) - {Int}_{absorbed}^{sample} (λ)] d λ}{\int \frac{λ}{hc} [{Int}_{emitted}^{reference} (λ) - {Int}_{absorbed}^{reference} (λ)] d λ}$ [0698] wherein n.sub.photon denotes the photon count and Int. the intensity.

[0699] Production and Characterization of Optoelectronic Devices

[0700] Optoelectronic devices, in particular OLED devices, comprising organic molecules according to the invention can be produced via vacuum-deposition methods. 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%.

[0701] 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, LT 95 to the time point, at which the measured luminance decreased to 95% of the initial luminance, etc. Accelerated lifetime measurements are performed (e.g. applying increased current densities). For example, LT80 values at 500 cd/m.sup.2 are determined using the following equation:

[00002] $LT 80 (500 \frac{{cd}^{2}}{m^{2}}) = LT 80 (L_{0}) {(\frac{L_{0}}{500 \frac{{cd}^{2}}{m^{2}}})}^{1.6}$

wherein L.sub.0 denotes the initial luminance at the applied current density.

[0702] The values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels is given.

[0703] HPLC-MS

[0704] HPLC-MS analysis is performed on an HPLC by Agilent (1100 series) with MS-detector (Thermo LTQ XL).

[0705] Exemplarily a typical HPLC method is as follows: a reverse phase column 4.6 mm×150 mm, particle size 3.5 μm from Agilent (ZORBAX Eclipse Plus 95A C18, 4.6×150 mm, 3.5 μm HPLC column) is used in the HPLC. The HPLC-MS measurements are performed at room temperature (rt) following gradients

TABLE-US-00001 Flow rate Time A B C [ml/min] [min] [%] [%] [%] 2.5 0 40 50 10 2.5 5 40 50 10 2.5 25 10 20 70 2.5 35 10 20 70 2.5 35.01 40 50 10 2.5 40.01 40 50 10 2.5 41.01 40 50 10
using the following solvent mixtures:

TABLE-US-00002 Solvent A: H.sub.2O (90%) MeCN (10%) Solvent B: H.sub.2O (10%) MeCN (90%) Solvent C: THF (50%) MeCN (50%)

[0706] An injection volume of 5 μL from a solution with a concentration of 0.5 mg/mL of the analyte is taken for the measurements.

[0707] Ionization of the probe is performed using an atmospheric pressure chemical ionization (APCI) source either in positive (APCI+) or negative (APCI−) ionization mode.

[0708] Concentration Dependent Spectral Purity

[0709] The organic molecules described herein in particular comprise severely decreased tendency to form intermolecular aggregates which are known to cause broadening of the photo luminescence (PL) spectra in doped films with increasing concentration. A measure of this spectral broadening in doped films (e.g. spin coated thin films containing 1 wt % or more of the organic molecule in PMMA matrix) with increasing concentration is the Concentration Dependent Spectral Purity (CDSP) value.

[0710] The CDSP is represented by the following relation:

CDSP=(λ.sub.max*CIEy)/c

wherein λ.sub.max is the maximum of the PL spectrum of a given organic molecule in nm, CIEy is the CIEy coordinate (Comission Internationale de l'Eclairage) derived from the PL spectrum of the organic molecule and c is the concentration of the organic molecule by weight in % in doped film.

[0711] The CDSP can be interpreted as follows:

[0712] If two different organic molecules have a comparable λ.sub.max in doped films of the same concentration, the one with a lower CDSP is preferred in terms of spectral purity. Especially the difference |ΔCDSP| between two concentrations provides an indication whether a material shows a high tendency to aggregate or not: the smaller the ΔCDSP value, the lower the aggregation tendency of a material.

[0713] Comparable values are especially obtained for concentrations c≥2 wt %.

Example 1

[0714] ##STR00060##

[0715] Example 1 was synthesized according to

[0716] AAV8 (82% yield), wherein 1,3-Dibromo-2,5-dichlorbenzene was replaced by 4-Chloro-3,5-dibromotoluene (CAS: 202925-05-1) and Bis(4-biphenylyl)amine (CAS: 102113-98-4) was used as reactant E5;

[0717] AAV17 (5% yield).

[0718] MS (HPLC-MS), m/z (retention time): 739.6 (4.93 min).

[0719] The emission maximum of example 1 (5% by weight in PMMA) is at 470 nm, the full width at half maximum (FWHM) is 0.19 eV, the CIEy coordinate is 0.22. The photoluminescence quantum yield (PLQY) is 52%.

Example 2

[0720] ##STR00061##

[0721] Example 2 was synthesized according to

[0722] AAV (75% yield), wherein p-toluidine (CAS: 106-49-0, 2.1 equivalents) was used as reactant E1;

[0723] AAV2 (69% yield), wherein 1-bromo-3,5-ditert-butylbenzene (2.05 equivalents, CAS: 22385-77-9) was used as reactant E2;

[0724] AAV3 (67% yield);

[0725] AAV4 (75% yield);

[0726] AAV5 (81% yield) using methane boronic acid (CAS: 13061-96-6, 10 equivalents) as E3.

[0727] MS (HPLC-MS), m/z (retention time): 687.7 (8.02 min) The emission maximum of example 2 (1% by weight in PMMA) is at 461 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIEy coordinate is 0.11. The photoluminescence quantum yield (PLQY) is 76%.

Example 3

[0728] ##STR00062##

[0729] Example 3 was synthesized according to

[0730] AAV1, wherein 4-Chloro-3,5-dibromtoluene (CAS: 202925-05-1) was used as E1 and 3-(2,4,6-trimethylphenyl)aniline (CAS: 851534-18-4) was used instead of 3,5-di-tert-butylanilin (76% yield);

[0731] AAV2, wherein 3,5-di-tert-butylanilin (CAS: 2380-36-1) was used instead of E2 (91% yield); and AAV5 (6% yield).

[0732] MS (HPLC-MS), m/z (retention time): 896.0 (9.102 min).

[0733] The emission maximum of example 3 (5% by weight in PMMA) is at 461 nm, the full width at half maximum (FWHM) is 0.20 eV, the CIEy coordinate is 0.14 and the onset of the emission spectrum is determined at 2.82 eV.

Example 4

[0734] ##STR00063##

[0735] Example 4 was synthesized according to

[0736] AAV1 (77% yield), wherein 3,5-di-tert-butylaniline (CAS: 2380-36-1, 2.1 equivalents) was used as reactant E1;

[0737] AAV2 (69% yield), wherein 1-bromo-4-cyclohexylbenzene (2.2 equivalents, CAS: 25109-28-8) was used as reactant E2;

[0738] AAV3 (29% yield);

[0739] AAV4 (99% yield);

[0740] AAV5 (32% yield) using methane boronic acid (CAS: 13061-96-6, 10 equivalents) as E3.

[0741] MS (HPLC-MS), m/z (retention time): 823.9 (9.67 min)

[0742] The emission maximum of example 4 (1% by weight in PMMA) is at 458 nm, the full width at half maximum (FWHM) is 0.16 eV, the CIEy coordinate is 0.08. The photoluminescence quantum yield (PLQY) is 84%.

Example 5

[0743] ##STR00064##

[0744] Example 5 was synthesized according to

[0745] AAV1 (62%), wherein 1,3-dibromo-2,5-dichlorbenzene was replaced by 4-chloro-3,5-dibromotoluene (CAS: 202925-05-1);

[0746] AAV2 (87% yield);

[0747] AAV17 (24% yield).

[0748] MS (HPLC-MS), m/z (retention time): 763.7 (9.29 min)

[0749] The emission maximum of example 5 (2% by weight in PMMA) is at 459 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIEy coordinate is 0.09. The photoluminescence quantum yield (PLQY) is 74%.

Example 6

[0750] ##STR00065##

[0751] Example 6 was synthesized according to

[0752] AAV13 (99% yield);

[0753] AAV8 (59% yield);

[0754] AAV3-a (79% yield);

[0755] AAV4-a (5% yield);

[0756] AAV5 (85% yield);

[0757] MS (HPLC-MS), m/z (retention time): 547.5 (6.15 min).

[0758] The emission maximum of example 6 (2% by weight in PMMA) is at 463 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIEy coordinate is 0.14. The photoluminescence quantum yield (PLQY) is 88%.

Example 7

[0759] ##STR00066##

[0760] Example 7 was synthesized according to

[0761] AAV1, wherein 4-chloro-3,5-dibromtoluene (CAS: 202925-05-1) was used as E1 (65% yield);

[0762] AAV2, wherein bromobenzene (CAS: 108-86-1) was used as E2 (68% yield);

[0763] AAV3 (62% yield);

[0764] and AAV4 (13% yield).

[0765] MS (HPLC-MS), m/z (retention time): 658.70 (15.00 min).

[0766] The emission maximum of example 7 (5% by weight in PMMA) is at 456 nm, the full width at half maximum (FWHM) is 0.19 eV, the CIEy coordinate is 0.10 and the PLQY is 60%. The onset of the emission spectrum is determined at 2.84 eV.

Example 8

[0767] ##STR00067##

[0768] Example 8 was synthesized according to

[0769] AAV1, wherein 4-chloro-3,5-dibromtoluene (CAS: 202925-05-1) was used as E1 (65% yield);

[0770] AAV2, wherein 1-bromo-4-tert-butylbenzene (CAS: 3972-65-4) was used as E2 (98% yield); AAV3 (81% yield);

[0771] and AAV4 (50% yield).

[0772] MS (HPLC-MS), m/z (retention time): 771.80 (22.79 min).

[0773] The emission maximum of example 8 (5% by weight in PMMA) is at 458 nm, the full width at half maximum (FWHM) is 0.17 eV, the CIEy coordinate is 0.12 and the PLQY is 62%. The onset of the emission spectrum is determined at 2.82 eV.

Example 9

[0774] ##STR00068##

[0775] The emission maximum of example 9 (5% by weight in PMMA) is at 461 nm, the full width at half maximum (FWHM) is 0.18 eV, the CIEy coordinate is 0.13 and the PLQY is 55%. The onset of the emission spectrum is determined at 2.81 eV.

Example D1

[0776] Example 1 was tested in the OLED D1, which was fabricated with the following layer structure:

TABLE-US-00003 Layer # Thickness D1 10 100 nm Al 9 2 nm Liq 8 20 nm NBPhen 7 10 nm MAT1 6 50 nm PYD2 (84%): MAT1 (15%): Example 1 (1%) 5 10 nm PYD2 4 10 nm TCTA 3 40 nm NPB 2 5 nm HAT-CN 1 50 nm ITO Subtrate glass MAT1 [00069] embedded image PYD2 [00070]

[0777] Device D1 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 18.9%. The emission maximum is at 472 nm with a FWHM of 32 nm at 7.3 V. The corresponding CIEx value is 0.12 and the CIEy value is 0.19. A LT95-value at 1200 cd/m.sup.2 of 1.5 h was determined.

Example D2

[0778] Example 5 was tested in the OLED D2, which was fabricated with the following layer structure:

TABLE-US-00004 Layer # Thickness D2 9 100 nm Al 8 2 nm Liq 7 11 nm NBPhen 6 20 nm MAT2 5 20 nm MAT3 (98%): Example 5 (2%) 4 10 nm MAT4 3 50 nm MAT5 2 7 nm HAT-CN 1 50 nm ITO Substrate Glass MAT2 [00071] embedded image MAT3 [00072]MAT4 [00073]MAT5 [00074]

[0779] Device D2 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 12.3%. The emission maximum is at 464 nm with a FWHM of 26 nm at 3.6 V. The corresponding CIEx value is 0.13 and the CIEy value is 0.10. A LT95-value at 1200 cd/m.sup.2 of 14.3 h was determined.

Example D3

[0780] Example 6 was tested in the OLED D, which was fabricated with the following layer structure:

TABLE-US-00005 Layer # Thickness D3 9 100 nm Al 8 2 nm Liq 7 11 nm NBPhen 6 20 nm MAT2 5 20 nm MAT3 (98%):: Example 6 (2%) 4 10 nm MAT4 3 50 nm MAT5 2 7 nm HAT-CN 1 50 nm ITO Substrate Glass

[0781] Device D3 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 10.0%. The emission maximum is at 468 nm with a FWHM of 26 nm at 3.5 V. The corresponding CIEx value is 0.12 and the CIEy value is 0.12. A LT95-value at 1200 cd/m.sup.2 of 243.7 h was determined.

Example D4

[0782] Example 7 was tested in the OLED D4, which was fabricated with the following layer structure:

TABLE-US-00006 Layer # Thickness D4 9 100 nm Al 8 2 nm Liq 7 11 nm NBPhen 6 20 nm MAT2 5 20 nm MAT3 (99%): Example 7 (1%) 4 10 nm MAT4 3 50 nm MAT5 2 7 nm HAT-CN 1 50 nm ITO Substrate glass

[0783] Device D4 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 9.6%. The emission maximum is at 458 nm with a FWHM of 26 nm at 3.37 V. The corresponding CIEy value is 0.07.

Example D5

[0784] Example 8 was tested in the OLED D5, which was fabricated with the following layer structure:

TABLE-US-00007 Layer # Thickness D5 9 100 nm Al 8 2 nm Liq 7 11 nm NBPhen 6 20 nm MAT2 5 20 nm MAT3 (99%): Example 8 (1%) 4 10 nm MAT4 3 50 nm MAT5 2 7 nm HAT-CN 1 50 nm ITO Substrate glass

[0785] Device D5 yielded an external quantum efficiency (EQE) at 1000 cd/m.sup.2 of 9.4%. The emission maximum is at 462 nm with a FWHM of 28 nm at 3.55 V. The corresponding CIEy value is 0.09.

[0786] Additional Examples of Organic Molecules of the Invention

##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083## ##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090##

FIGURES

[0787] FIG. 1 Emission spectrum of example 1 (5% by weight) in PMMA.

[0788] FIG. 2 Emission spectrum of example 2 (1% by weight) in PMMA.

[0789] FIG. 3 Emission spectrum of example 3 (5% by weight) in PMMA.

[0790] FIG. 4 Emission spectrum of example 4 (1% by weight) in PMMA.

[0791] FIG. 5 Emission spectrum of example 5 (2% by weight) in PMMA.

[0792] FIG. 6 Emission spectrum of example 6 (2% by weight) in PMMA.

[0793] FIG. 7 Emission spectrum of example 7 (5% by weight) in PMMA.

[0794] FIG. 8 Emission spectrum of example 8 (5% by weight) in PMMA.

ORGANIC MOLECULES FOR OPTOELECTRONIC DEVICES

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