COMPOSITION FOR AN ORGANIC ELECTRONIC DEVICE AND ORGANIC ELECTRONIC DEVICE USING THE SAME

Abstract

Provided are a composition for an organic electronic device and an organic electronic device using the same. The composition includes a first host compound represented by the following Formula (I) and a second host compound represented by the following Formula (II).

##STR00001## wherein Y is a single bond, O or S; Z.sup.1 to Z.sup.3 are each CH or adjacent two of Z.sup.1 to Z.sup.3 are joined together to form an aryl ring or a heteroaryl ring; two of X.sup.1 to X.sup.3 are each a nitrogen atom, the other of X.sup.1 to X.sup.3 is CH or a nitrogen atom; Q.sup.1 and Q.sup.2 are each CH or Q.sup.1 and Q.sup.2 are joined together to form an aryl ring.

Claims

1. A composition for an organic electronic device, comprising: a first host compound represented by the following Formula (I); and ##STR00486## a second host compound represented by the following Formula (II); ##STR00487## wherein Y in Formula (I) is a single bond, an oxygen atom or a sulfur atom; Z.sup.1 to Z.sup.3 in Formula (I) are each independently CH, adjacent two of Z.sup.1 to Z.sup.3 in Formula (I) are joined together to form an aryl ring and a remaining one of Z.sup.1 to Z.sup.3 is CH, or adjacent two of Z.sup.1 to Z.sup.3 in Formula (I) are joined together to form a heteroaryl ring containing at least one furan group or at least one thiophene group and the remaining one of Z.sup.1 to Z.sup.3 is CH; two of X.sup.1 to X.sup.3 in Formula (I) are each independently a nitrogen atom, and the other of X.sup.1 to X.sup.3 in Formula (I) is CH or a nitrogen atom; L, L.sup.1 and L.sup.2 in Formula (I) are each independently an arylene group having 6 to 18 ring carbon atoms; n, n1 and n2 are each independently an integer from 0 to 2; G.sup.1 and G.sup.2 in Formula (I) are each independently an aryl group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, an arylthioxy group having 6 to 18 ring carbon atoms, or a heteroaryl group containing a N, O, or S atom and having 3 to 30 ring carbon atoms; L.sup.3 in Formula (II) is an arylene group having 6 to 18 ring carbon atoms; n3 is an integer from 0 to 2; G.sup.4 and G.sup.5 in Formula (II) are each independently an aryl group having 6 to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms, an arylthioxy group having 6 to 18 ring carbon atoms, or an heteroaryl group containing a N, O, or S atom and having 3 to 30 ring carbon atoms; and Q.sup.1 and Q.sup.2 in Formula (II) are each independently CH or Q.sup.1 and Q.sup.2 in Formula (II) are joined together to form an aryl ring.

2. The composition as claimed in claim 1, wherein the first host compound is represented by the following Formula (I): ##STR00488##

3. The composition as claimed in claim 2, wherein a weight ratio of the first and second host compounds ranges from 3:7 to 7:3.

4. The composition as claimed in claim 2, wherein the first host compound is represented by any one of the following Formulae (I-I) to (I-XVI): ##STR00489## ##STR00490## ##STR00491## ##STR00492##

5. The composition as claimed in claim 2, wherein the second host compound is represented by any one of the following Formulae (II-I) to (II-III): ##STR00493## wherein W.sup.1 and W.sup.2 are each independently a methyl group, an ethyl group, a propyl group, a butyl group or a phenyl group.

6. The composition as claimed in claim 2, wherein L.sup.1 and L.sup.2 are each independently a phenylene group.

7. The composition as claimed in claim 2, wherein n1 and n2 are each independently an integer 0 or 1.

8. The composition as claimed in claim 2, wherein G.sup.1 and G.sup.2 are each independently selected from the group consisting of: a phenyl group, a naphthyl group and a 3,5-diphenylphenyl group.

9. The composition as claimed in claim 2, wherein G.sup.1 and G.sup.2 are each independently selected from the group consisting of: ##STR00494## where X is O, S, or ##STR00495## wherein p is an integer from 1 to 5, m is an integer from 1 to 4, and n is an integer from 1 to 3; and A.sup.1 to A.sup.3 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, a halo group, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, and an alkynyl group having 2 to 6 carbon atoms.

10. The composition as claimed in claim 2, wherein L.sup.3 is a phenylene group.

11. The composition as claimed in claim 2, wherein n3 is an integer 0 or 1.

12. The composition as claimed in claim 2, wherein G.sup.4 and G.sup.5 are each independently selected from the group consisting of: a phenyl group, a biphenylyl group, and a naphthyl group.

13. The composition as claimed in claim 2, wherein G.sup.4 and G.sup.5 are each independently selected from the group consisting of: ##STR00496## where X is O, S, or ##STR00497## wherein p is an integer from 1 to 5, m is an integer from 1 to 4, and n is an integer from 1 to 3; and A.sup.4 to A.sup.6 are each independently selected from the group consisting of: a hydrogen atom, a deuterium atom, a halo group, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, and an alkynyl group having 2 to 6 carbon atoms.

14. The composition as claimed in claim 2, wherein a group of ##STR00498## of the first host compound represented by Formula (I) is selected from the group consisting of: ##STR00499## ##STR00500## ##STR00501## ##STR00502## ##STR00503## ##STR00504## ##STR00505##

15. The composition as claimed in claim 2, wherein G.sup.4 and G.sup.5 are each independently selected from the group consisting of: ##STR00506##

16. The composition as claimed in claim 1, wherein the first host compound is selected from the group consisting of: ##STR00507## ##STR00508## ##STR00509## ##STR00510## ##STR00511## ##STR00512## ##STR00513## ##STR00514##

17. The composition as claimed in claim 16, wherein the second host compound is selected from the group consisting of: ##STR00515## ##STR00516## ##STR00517##

18. An organic electronic device, comprising a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises the composition as claimed in claim 1.

19. The organic electronic device as claimed in claim 18, wherein the organic electronic device is an organic light emitting device.

20. The organic electronic device as claimed in claim 19, wherein the organic light emitting device comprises: a hole injection layer formed on the first electrode; a hole transport layer formed on the hole injection layer; an emission layer formed on the hole transport layer, wherein the emission layer comprises the composition as claimed in claim 1; an electron transport layer formed on the emission layer; and an electron injection layer formed between the electron transport layer and the second electrode.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0100] FIG. 1 illustrates a schematic cross-sectional view of an OLED.

[0101] FIG. 2 is a photoluminescence spectra of Compound I-4, Compound II-2 and Composition 16.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0102] Hereinafter, one skilled in the arts can easily realize the advantages and effects of a composition for an organic electronic device and an organic light emitting device using the same in accordance with the present invention from the following examples. It should be understood that the descriptions proposed herein are just preferable examples only for the purpose of illustrations, not intended to limit the scope of the invention. Various modifications and variations could be made in order to practice or apply the present invention without departing from the spirit and scope of the invention.

First Host Compound of a Composition for an Organic Electronic Device

[0103]

TABLE-US-00001 TABLE 1 chemical structures of the first host compounds [00357] Compound I-1 [00358] Compound I-2 [00359] Compound I-3 [00360] Compound I-4 [00361] Compound I-5 [00362] Compound I-6 [00363] Compound I-7 [00364] Compound I-8 [00365] Compound I-9 [00366] Compound I-10 [00367] Compound I-11 [00368] Compound I-12 [00369] Compound I-13 [00370] Compound I-14 [00371] Compound I-15 [00372] Compound I-16 [00373] Compound I-17 [00374] Compound I-18 [00375] Compound I-19 [00376] Compound I-20 [00377] Compound I-21 [00378] Compound I-22 [00379] Compound I-23 [00380] Compound I-24 [00381] Compound I-25 [00382] Compound I-26 [00383] Compound I-27 [00384] Compound I-28

[0104] Synthesis of Compounds I-1 to I-15 and I-28 for First Host Compound

[0105] Compounds I-1 and I-2 used as the first host compound were synthesized by the following steps. The synthesis pathway was summarized in Scheme R1.

##STR00385##

[0106] wherein Intermediate C1 was

##STR00386##

and Intermediate C2 was

[0107] ##STR00387##

[0108] Compounds I-1 and I-2 could be obtained through a reaction mechanism same as the synthetic method of Compounds VII and VI in U.S. Patent Application Publication No. 2017/0213978 A1 by respectively adopting Intermediate C2 and Intermediate C1 stated above.

[0109] Besides, Compound I-7 could be obtained through a reaction mechanism same as the synthetic method of Compound III in U.S. Patent Application Publication No. 2017/0213978 A1, and the synthetic method was similar to Scheme R1 using Intermediate C1 stated above but adopting 4-chloro-2, 6-diphenylpyrimidine (CAS No. 29509-91-9) to replace 2-chloro-4,6-diphenyl-1,3,5-triazine (CAS No. 3842-55-5).

[0110] For Compounds I-3 to I-6, I-8 to I-15 and I-28, they could be successfully synthesized through a reaction mechanism similar to Scheme R1 by respectively adopting Intermediate C1 or C2 and other reactants including a triazine or pyrimidine moiety to replace 2-chloro-4,6-diphenyl-1,3,5-triazine. The specific reactants including a triazine or pyrimidine moiety and Intermediate C1 or C2 used for synthesizing Compounds I-3 to I-6, I-8 to I-15 and I-28 were listed in Table 2; besides, Compounds I-3 to I-6, I-8 to I-15 and I-28 were identified by FD-MS, and the chemical structure, yield, formula and mass of each of Compounds I-3 to I-6, I-8 to I-15 and I-28 were also listed in Table 2-1. Compounds I-3 to I-6, I-8 to I-15 and I-28 were also identified by H.sup.1-NMR and the results thereof were listed in Table 2-2.

[0111] Preparation of Reactant for Compound I-10

##STR00388##

used to synthesize Compound I-10 was synthesized by the following steps. The synthesis pathway was summarized in Scheme R1-1.

##STR00389##

[0112] A mixture of dibenzo[b,d]furan-1-ylboronic acid (1.0 eq), 2,4-dichloro-6-(D.sub.5)phenyl-1,3,5-triazine (1.1 eq), tris(dibenzylideneacetone)dipalladium[Pd.sub.2(dba).sub.3] (0.015 eq), triphenylphosphine (PPh.sub.3) were stirred in a mixed solution of methoxymethane (DME) (0.5M) and Na.sub.2CO.sub.3 aqueous solution (2.0 M). The reaction mixture was heated to about 65 C. to 70 C. and stirred for 24 hours under nitrogen atmosphere. After completion of the reaction, water and toluene were added to the reaction mixture. Subsequently, the organic layer was recovered by solvent extraction operation and dried over sodium sulfate. The solvent was then removed from the organic layer under reduced pressure, and the resulting residue was washed with methanol, and dry to obtain a white solid product as

##STR00390##

in a yield of 80%. Its FD-MS analysis: C.sub.21H.sub.7D.sub.5ClN.sub.3O; and observed value of 362.82.

TABLE-US-00002 TABLE 2-1 Intermediate C1 or C2 and Reactant adopted to prepare Compounds I-3 to I-6, I-8 to I-15 and I-28 and their yields, formulae, and FD-MS data Intermediate First Host Compound C1/ Reactant/ Chemical Yield Formula/ Intermediate C2 CAS No. Structure (%) Mass (M.sup.+) [00391] [00392] [00393] 83 C.sub.52H.sub.33N.sub.3/ 699.84 [00394] [00395] [00396] 85 C.sub.58H.sub.37N.sub.3/ 775.93 [00397] [00398] [00399] 80 C.sub.58H.sub.37N.sub.3/ 775.93 [00400] [00401] [00402] 86 C.sub.52H.sub.33N.sub.3/ 699.84 [00403] [00404] [00405] 75 C.sub.53H.sub.34N.sub.2/ 698.85 [00406] [00407] [00408] 81 C.sub.52H.sub.31N.sub.3O/ 713.82 [00409] [00410] [00411] 82 C.sub.52H.sub.26D.sub.5N.sub.3O/ 718.85 [00412] [00413] [00414] 81 C.sub.58H.sub.35N.sub.3O/ 789.92 [00415] [00416] [00417] 75 C.sub.53H.sub.32N.sub.2O/ 712.83 [00418] [00419] [00420] 76 C.sub.53H.sub.32N.sub.2O/ 712.83 [00421] [00422] [00423] 70 C.sub.53H.sub.32N.sub.2O/ 712.83 [00424] [00425] [00426] 79 C.sub.53H.sub.32N.sub.2O/ 712.83 [00427] [00428] [00429] 85 C.sub.52H.sub.31N.sub.3O/ 713.82

TABLE-US-00003 TABLE 2-2 H.sup.1-NMR results of Compounds I-3 to I-6, I-8 to I-15 and I-28 First Host Compound H.sup.1-NMR [00430] .sup.1H NMR (500 MHz, CDCl.sub.3): 9.05 (s, 1H) m 8.79-8.73 (dd, 4H) m 8.43 (dd, 1H),7.91 (d 1H), 7.77-7.46 (m, 18H), 7.47 (t, 1H), 7.46-7.30 (m, 2H), 7.16 (t, 2H), 7.06 (t, 1H), 6.66 (t, 1H), 5.89 (d, 1H) ppm. [00431] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.81 (s, 2H), 8.69 (d, J = 2.0 Hz, 1H), 8.67 (d, 1H), 8.64 (d, 2H), 7.90-7.85 (m, 2H), 7.8 g-7.75 (m, 2H), 7.75-7.67 (m, 5H), 7.67-7.55 (m, 8H), 7.55-7.50 (m, 4H), 7.50-7.40 (m, 2H), 7.40-7.30 (m, 1H), 7.30-7.20 (m, 3H), 7.13 (t, 1H), 7.09 (t, 1H), 6.64 (t, 1H), 5.89 (d, 1H) ppm. [00432] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.82 (d, 2H), 8.75-8.65 (m, 2H), 8.61 (d, 2H), 8.00 (s, 1H), 8.60 (d, 2H), 7.80-7.70 (m, 4H), 7.70-7.61 (m, 6H), 7.61-7.51 (m, 7H), 7.51-7.40 (m, 3H), 7.30-7.20 (m, 3H), 7.16 (t, 1H), 7.10 (t, 1H), 6.69 (t, 1H), 5.94 (d, J = 10.5 Hz, 1H) ppm. [00433] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.94 (s, 1H), 8.75 (d, 4H), 8.73 (d, 1H), 8.01 (d, 1H), 7.91 (d, 1H), 7.79 (dd, 1H), 7.72 (dd, 1H), 7.71 (m, 1H), 7.63-7.52 (m, 14H), 7.40 (dd, 1H), 7.33 (t, 1H), 7.26 (d, 1H), 7.15-7.07 (m, 3H), 6.64 (t, 1H), 5.87 (d, 1H) ppm. [00434] .sup.1H NMR (500 MHz, CDCl.sub.3): 9.03 (d, 1H), 8.48-8.41 (m, 1H), 8.39 (dd, J = 13, 1H), 8.30-8.24 (m, 2H), 8.21 (d, 1H), 8.02 (s, 1H), 7.91 (d, 1H), 8.03-7.75 (m, 1H), 7.75-7.66 (m, 4H), 7.66-7.58 (m, 6H), 7.58-7.45 (m, 7H), 7.45-7.37 (m, 1H), 7.37-7.26 (m, 2H), 7.19-7.10 (m, 2H), 7.10-7.00 (m, 1H), 6.67 (t, 1H), 5.93 (d, 1H) ppm. [00435] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.74 (s, 1H), 8.63 (d, 1H), 8.58 (d, 2H), 8.43 (d, 1H), 8.24 (d, 1H), 7.92 (d, 1H), 7.84 (d, 1H), 7.78 (d, 1H), 7.75-7.52 (m, 14H), 7.46 (t, 1H), 7.34 (t, 1H), 7.26 (t, 1H), 7.20-7.05 (m, 3H), 6.65 (t, 1H), 5.90 (d, 1H) ppm. [00436] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.75 (d, 1H), 8.38 (dd, 1H), 8.46 (d, 1H), 8.25 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.78 (d, 1H), 7.75-7.60 (m, 10H), 7.60-7.53 (m, 1H), 7.52-7.44 (m, 1H), 7.35 (t, 3H), 7.29 (d, J = 10.5 Hz, 1H), 7.20-7.05 (m, 3H), 6.70 (t, 1H), 5.92 (d, 1H) ppm. [00437] .sup.1H NMR (500 MHz, CDCl.sub.3): 9.04 (s, 1H), 8.93 (s, 1H), 8.88 (s, 1H), 8.71 (d, 1H), 8.67 (d, 1H), 8.48 (d, 1H), 8.05-7.85 (m, 3H), 7.84-7.61 (m, 7H), 7.60-7.49 (m, 9H), 7.49-7.26 (m, 3H), 7.20-7.11 (m, 2H), 7.11-7.00 (m, 1H), 6.68 (t, 1H), 5.92 (d, 1H) ppm. [00438] .sup.1H NMR (500 MHz, CDCl.sub.3): 9.01 (d, 1H), 8.49 (d, 1H), 8.39 (dd, , 1H), 8.30-8.20 (m, 3H), 8.10-8.03 (m, 2H), 7.98 (d, 1H), 7.90 (d, 1H), 7.83-7.73 (m, 1H), 7.72-7.45 (m, 12H), 7.42-7.26 (m, 3H), 7.20-7.10 (m, 2H), 7.09-7.00 (m, 1H), 6.65 (td, 1H), 5.90 (d, 1H) ppm. [00439] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.66 (d, 2H), 8.39 (s, 1H), 8.20-8.12 (m, 2H), 8.09 (d, 1H), 8.05-7.95 (m, 4H), 7.89-7.80 (m, 2H), 7.80-7.69 (m, 3H), 7.69-7.58 (m, 6H), 7.57-7.50 (m, 4H), 7.39 (t,, 1H), 7.33 (t, 1H), 7.29 (d, 1H), 7.15-7.04 (m, 2H), 6.64 (t, 1H), 5.91 (d, 1H) ppm. [00440] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.70(dd, J = 10.0, 3.5 Hz, 2H), 8.58 (d, J = 2.5 Hz, 1H), 8.51 (d, 1H), 8.21 (dd, 1H), 8.05 (s, 1H), 8.03-8.01 (m, 1H), 8.00-7.93 (m, 2H), 7.92-7.88 (m, 1H), 7.76-7.70 (m, 2H), 7.70-7.56 (m, 7H), 7.55-7.45 (m, 5H), 7.4-7.26 (m, 3H), 7.20-7.10 (m, 2H), 7.10-7.02 (m, 1H), 6.66 (t, 1H), 5.89 (d, 1H) ppm. [00441] .sup.1H NMR (500 MHz, CDCl.sub.3): 8.62-8.52(m, 2H), 8.41 (d, 1H), 8.24 (d, J = 2.0 Hz, 1H), 8.20-8.10 (dd, H), 8.04-7.92 (m, 3H), 7.85-7.69 (m, 5H), 7.69-7.57 (m, 7H), 7.57-7.45 (m, 4H), 7.45-7.31 (m, 2H), 7.28 (dd, 1H), 7.19-7.05 (m, 2H), 6.66 (t, 1H), 5.91 (d, 1H) ppm. [00442] .sup.1H NMR (500 MHz, CDCl.sub.3): 9.17 (s, 1H), 8.73-8.68 (m, 2H), 8.65 (d, 1H), 8.60 (d, 2H), 8.11 (d, 1H), 8.02 (d, 1H), 7.83 (d, 1H), 7.79-7.69 (m, 4H), 7.69-7.61 (m, 6H), 7.61-7.51 (m, 4H), 7.48 (t, 1H), 7.43-7.31 (m, 2H), 7.26 (t, 1H), 7.20-7.05 (m, 2H), 6.67 (t, 1H), 5.90 (d, 1H) ppm.

[0113] Synthesis of Compounds I-16 to I-19 and I-27 for First Host Compound Compounds I-16 to I-19 and I-27 used as the first host compound were synthesized by the following steps. The synthesis pathway was summarized in Scheme R2.

##STR00443##

[0114] wherein Intermediate C1 was

##STR00444##

and Intermediate C2 was

[0115] ##STR00445##

[0116] Intermediates C1 and C2 could be obtained through a Suzuki-Miyaura reaction from Intermediates D1 and D2 in U.S. Patent Application Publication No. 2017/0213970 A1.

[0117] Intermediate C1 or C2 (1.0 eq), Reactant Bn (1.2 eq), Pd(OAc).sub.2 (0.01 eq), and 2-(dicyclohexylphosphino)biphenyl[P(Cy).sub.2(2-biPh)](0.04 eq) were stirred in a mixed solution of toluene/ethanol (0.5M, v/v=10/1) and 3.0 M of K.sub.2CO.sub.3 aqueous solution. The reaction mixture was heated to about 100 C. and stirred for 12 hours under nitrogen atmosphere. After completion of the reaction, water and toluene were added to the reaction mixture. Subsequently, the organic layer was recovered by solvent extraction operation and dried over sodium sulfate. The solvent was then removed under reduced pressure, and the resulting residue was purified by silica gel column chromatography. The obtained residue was recrystallized with toluene to obtain a white solid product as Compounds I-16 to I-19 and I-27.

[0118] For Compounds I-16 to I-19 and I-27, they could be successfully synthesized through a reaction mechanism same as Scheme R2 by respectively adopting Intermediate C1 or C2 and other Reactants Bn including a triazine or pyrimidine moiety. Intermediate C1 or C2 and the specific Reactants Bn including a triazine or pyrimidine moiety used for synthesizing Compounds I-16 to I-19 and I-27 were listed in Table 3; besides, Compounds I-16 to I-19 and I-27 were identified by FD-MS, and the chemical structure, yield, formula and mass of each of Compounds I-16 to I-19 and I-27 were also listed in Table 3-1. Compounds I-16 to I-19 and I-27 were also identified by I-1.sup.1-NMR (500 MHz, CDCl.sub.3) and the results thereof were listed in Table 3-2.

TABLE-US-00004 TABLE 3-1 Intermediate C1 or C2 and Reactant Bn adopted to prepare Compounds I-16 to I-19 and I-27 and their yields, formulae, and FD-MS data First Host Compound Intermediate C1/ Reactant Bn/ Chemical Yield Formula/ Intermediate C2 CAS No. Structure (%) Mass (M.sup.+) [00446] [00447] [00448] 85 C.sub.46H.sub.29N.sub.3/ 623.74 [00449] [00450] [00451] 65 C.sub.58H.sub.37N.sub.3/ 775.93 [00452] [00453] [00454] 77 C.sub.58H.sub.37N.sub.3/ 775.93 [00455] [00456] [00457] 82 C.sub.58H.sub.37N.sub.3/ 775.93 [00458] [00459] [00460] 76 C.sub.58H.sub.37N.sub.3/ 775.93

TABLE-US-00005 TABLE 3-2 H.sup.1-NMR results of Compounds I-16 to I-19 and I-27 First Host Compound H.sup.1-NMR [00461] 9.01 ppm (d, 1H), 8.99 ppm (s, 1H), 8.75 ppm (d, 4H), 8.65 ppm (d, 1H), 8.05 ppm (d, 1H), 7.7 ppm (t, 2H), 7.60-7.58 ppm (m, 8H), 7.35-7.31 ppm (m, 4H), 7.29-7.05 ppm (m, 5H), 6.70 ppm (t, 1H), 5.85 ppm (d, 1H). [00462] 9.01 ppm (s, 2H), 8.89 ppm (s, 1H), 8.74 ppm (d, 2H), 8.07 ppm (d, 1H), 7.84 ppm (dd, 2H), 7.76-7.68 ppm (m, 6H), 7.66-7.57 ppm (m, 6H),, 7.52-7.46 ppm (m, 5H) 7.44-7.39 ppm (m, 3H), 7.36-7.30 ppm (m, 4H), 7.16 ppm (t, 1H), 7.11-7.06 ppm (m, 2H), 6.70 ppm (t, 1H), 5.89 ppm (d, 1H). [00463] 9.23 ppm (s, 1H), 9.08 ppm (s, 2H), 8.96 ppm (d, 1H), 8.92 ppm (s, 2H), 8.85 ppm (d, 2H), 8.69 ppm (d, 2H), 8.10 ppm (d, 1H), 8.02 ppm (d, 1H), 7.85-7.76 ppm (m, 11H), 7.73-7.67 ppm (m, 10H), 7.64-7.58 ppm (m, 12H), 7.53 ppm (dd, 8H), 7.44 ppm (t, 4H), 7.34 ppm (t, 4H), 7.19-7.12 ppm (m, 6H), 7.05 ppm (t, 4H), 6.69 ppm (t, 1H), 6.05 ppm (d, 1H), 5.85 ppm (d, 1H). [00464] 9.23 ppm (s, 1H), 9.04 ppm (s, 2H), 8.94 ppm (d, IH), 8.92 ppm (s, 1H), 8.88 ppm (s, 2H), 8.86 ppm (d, 2H), 8.73 ppm (d, 2H) 8.10 ppm (d, 1H), 8.19 ppm (s, 1H), 8.02 ppm (d, 1H), 8.00ppm (s, 1H)7.83 ppm (d, 6H), 7.78 ppm (d, 4H), 7.70 ppm (dd, 4H), 7.70-7.51 ppm (m, 25H), 7.46 ppm (t, 4H), 7.34 ppm (t, 4H), 7.20-7.13 ppm (m, 5H), 7.08-7.04 ppm (m, 4H), 6.68 ppm (t, 1H), 6.05 ppm (dd 1H), 5.88 ppm (dd, 1H). [00465] 8.97 ppm (s, 3H), 8.84 ppm (s, 1H), 8.81 ppm (d, 1H), 8.77 ppm (d, 1H), 8.06 ppm (m, 2H), 7.80-7.76 ppm (m, 6H), 7.62-7.49 ppm (m, 12H), 7.47-7.41 ppm (m, 4H), 7.34-7.24 ppm (m, 3H), 7.09-7.05 ppm (m, 2H), 6.68 ppm (t, 1H), 5.87 ppm (d, 1H).

[0119] Synthesis of Compounds 1-20 to 1-23 for First Host Compound

[0120] Compounds I-20 to I-23 used as the first host compound were synthesized by the following steps. The synthesis pathway was summarized in Scheme R3.

##STR00466##

[0121] wherein Intermediate Cn-B was

##STR00467##

(Intermediate C1-B),

[0122] ##STR00468##

(Intermediate C2-B),

[0123] ##STR00469##

(Intermediate C7-B), or

[0124] ##STR00470##

(Intermediate C3-B).

[0125] Compounds I-20 to I-23 could be obtained through a reaction mechanism same as the synthetic method of Compounds V, IX, XIX and VII in U.S. Patent Application Publication No. 2018/0159044 A1 by respectively adopting Intermediate C1-B, Intermediate C2-B, Intermediate C7-B and Intermediate C3-B stated above.

[0126] Synthesis of Compounds I-24 to I-26 for First Host Compound

[0127] Compounds I-24 and I-25 used as the first host compound were synthesized by the following steps. The synthesis pathway was summarized in Scheme R4.

##STR00471##

[0128] wherein Intermediate Dn-B was

##STR00472##

(Intermediate D1-B) or

[0129] ##STR00473##

(Intermediate D4-B).

[0130] Compounds I-24 and I-25 could be obtained through a reaction mechanism same as the synthetic method of Compounds VI and VII in U.S. Patent Application Publication No. 2018/0155312 A1 by respectively adopting Intermediate D1-B and Intermediate D4-B stated above.

[0131] Besides, Compound I-26 could be obtained through a reaction mechanism same as the synthetic method of Compound III in U.S. Patent Application Publication No. 2018/0155312 A1, and the synthetic method was similar to Scheme R4 using Intermediate D1-B stated above but adopting 4-chloro-2,6-diphenylpyrimidine to replace 2-chloro-4,6-diphenyl-1,3,5-triazine.

Second Host Compound of a Composition for an Organic Electronic Device

[0132]

TABLE-US-00006 TABLE 4 chemical structures and CAS No. of the second host compounds Chemical structure [00474] [00475] CAS No. [57102-51-9] [1643479-47-3] Chemical structure [00476] [00477] CAS No. [1357150-54-9] [1541194-36-8]

[0133] Preparation of a Composition for an Organic Electronic Device

[0134] Compositions 1 to 51 were each obtained by adopting an appropriate amount of aforesaid first host compound listed in Table 1 and second host compound listed in Table 4, and the species of aforesaid first host compound and second host compound used in Compositions 1 to 51 were listed in Table 5. The weight ratio of the first host compound and second host compound in each of Compositions 1 to 47 was 1:1; the weight ratio of the first host compound and second host compound in Compositions 48 to 50 was 6:4; the weight ratio of the first host compound and second host compound in Composition 51 was 4:6.

[0135] Compositions 52 and 53 were respectively obtained by adopting a composition of TPBi and Compound II-2 or a composition of TPBi and Compound II-1 at a weight ratio of 1:1 as listed in Table 5.

TABLE-US-00007 TABLE 5 materials of first and second host compounds and weight ratio therebetween in Compositions 1 to 53 Weight ratio of first Composition First Host Second Host and second host No. Compound Compound compounds 1 Compound I-1 Compound II-1 1:1 2 Compound I-2 Compound II-1 1:1 3 Compound I-4 Compound II-1 1:1 4 Compound I-5 Compound II-1 1:1 5 Compound I-9 Compound II-1 1:1 6 Compound I-18 Compound II-1 1:1 7 Compound I-19 Compound II-1 1:1 8 Compound I-20 Compound II-1 1:1 9 Compound I-22 Compound II-1 1:1 10 Compound I-24 Compound II-1 1:1 11 Compound I-26 Compound II-1 1:1 12 Compound I-28 Compound II-1 1:1 13 Compound I-1 Compound II-2 1:1 14 Compound I-2 Compound II-2 1:1 15 Compound I-3 Compound II-2 1:1 16 Compound I-4 Compound II-2 1:1 17 Compound I-5 Compound II-2 1:1 18 Compound I-6 Compound II-2 1:1 19 Compound I-7 Compound II-2 1:1 20 Compound I-8 Compound II-2 1:1 21 Compound I-9 Compound II-2 1:1 22 Compound I-10 Compound II-2 1:1 23 Compound I-11 Compound II-2 1:1 24 Compound I-12 Compound II-2 1:1 25 Compound I-13 Compound II-2 1:1 26 Compound I-14 Compound II-2 1:1 27 Compound I-15 Compound II-2 1:1 28 Compound I-16 Compound II-2 1:1 29 Compound I-17 Compound II-2 1:1 30 Compound I-18 Compound II-2 1:1 31 Compound I-19 Compound II-2 1:1 32 Compound I-20 Compound II-2 1:1 33 Compound I-21 Compound II-2 1:1 34 Compound I-22 Compound II-2 1:1 35 Compound I-23 Compound II-2 1:1 36 Compound I-24 Compound II-2 1:1 37 Compound I-25 Compound II-2 1:1 38 Compound I-26 Compound II-2 1:1 39 Compound I-27 Compound II-2 1:1 40 Compound I-2 Compound II-3 1:1 41 Compound I-7 Compound II-3 1:1 42 Compound I-2 Compound II-4 1:1 43 Compound I-5 Compound II-4 1:1 44 Compound I-12 Compound II-4 1:1 45 Compound I-20 Compound II-4 1:1 46 Compound I-22 Compound II-4 1:1 47 Compound I-18 Compound II-4 1:1 48 Compound I-2 Compound II-1 6:4 49 Compound I-26 Compound II-1 6:4 50 Compound I-5 Compound II-4 6:4 51 Compound I-12 Compound II-4 4:6 52 TPBi Compound II-2 1:1 53 TPBi Compound II-1 1:1

[0136] Analysis of Photoluminescence (PL) Spectra

[0137] Glass substrates in a thickness of 500 cleaned by acetone and isopropyl alcohol were prepared. Compounds I-1 to I-28 listed in Table 1, Compounds II-1 to II-4 listed in Table 4 and Compositions 1 to 53 listed in Table 5 were deposited on each glass substrate under vacuum degree of 10.sup.6 torr to prepare each PL test film of Compounds I-1 to I-28, Compounds II-1 to II-4 and Compositions 1 to 53.

[0138] PL test films of Compositions 2, 8, 9, 13, 14, 16, 17, 19, 28 to 39, 42, 43, 45 to 47, 52 and the first and second host compounds concerned were respectively measured by a fluorescence spectrophotometer (Hitachi Fl-7000) to obtain each set of PL spectra, and then the wavelengths at emission maximum ( max) thereof in each set of PL spectra were summarized in Table 6.

[0139] The PL spectra of Composition 16 and its components of Compound I-4 and Compound II-2 were measured and recorded as shown in FIG. 2.

TABLE-US-00008 TABLE 6 max of Compositions 2, 8, 9, 13, 14, 16, 17, 19, 28 to 39, 42, 43, 45 to 47 and 52 and max of the first and second host compounds concerned max of max of Second max of Compo- Second First Host Host Compo- sition First Host Host Compound Compound sition No. Compound Compound (nm) (nm) (nm) 2 I-2 II-1 393 413 498 8 I-20 II-1 445 413 493 9 I-22 II-1 417 413 500 13 I-1 II-2 394 414 488 14 I-2 II-2 393 414 478 16 I-4 II-2 407 414 500 17 I-5 II-2 419 414 500 19 I-7 II-2 387 414 462 28 I-16 II-2 402 414 478 29 I-17 II-2 404 414 493 30 I-18 II-2 398 414 494 31 I-19 II-2 392 414 499 32 I-20 II-2 445 414 466 33 I-21 II-2 401 414 488 34 I-22 II-2 417 414 505 35 I-23 II-2 397 414 508 36 I-24 II-2 395 414 494 37 I-25 II-2 410 414 483 38 I-26 II-2 389 414 463 39 I-27 II-2 403 414 498 42 I-2 II-4 393 388 469 43 I-5 II-4 419 388 469 45 I-20 II-4 445 388 472 46 I-22 II-4 417 388 477 47 I-18 II-4 398 388 463 52 TPBi Compound 382 414 418 II-2

[0140] As shown in Table 6 and FIG. 2, in each set of PL spectra, the max of Compositions 2, 8, 9, 13, 14, 16, 17, 19, 28 to 39, 42, 43, and 45 to 47 were obviously found to red shift to longer wavelength range as compared with the max of the first host and second host compounds concerned. However, the degree of red shift for max of Composition 52 was obviously smaller than those of Compositions 2, 8, 9, 13, 14, 16, 17, 19, 28 to 39, 42, 43, and 45 to 47. Accordingly, it demonstrated that the first and second host compounds concerned of Compositions 2, 8, 9, 13, 14, 16, 17, 19, 28 to 39, 42, 43 and 45 to 47 respectively formed an exciplex.

[0141] Preparation of OLED Devices

[0142] A glass substrate coated with an ITO layer (abbreviated as ITO substrate) in a thickness of 1500 was placed in distilled water containing a detergent dissolved therein, and was ultrasonically washed. The detergent was a product manufactured by Fischer Co., and the distilled water was distilled water filtered twice through a filter (Millipore Co.). After the ITO layer had been washed for 30 minutes, it was ultrasonically washed twice with distilled water for 10 minutes. After the completion of washing, the glass substrate was ultrasonically washed with isopropyl alcohol, acetone and methanol solvents and then dried, after which it was transported to a plasma cleaner. Then the substrate was cleaned with oxygen plasma for 5 minutes, and then transferred to a vacuum evaporator.

[0143] After that, various organic materials and metal materials were sequentially deposited on the ITO substrate to obtain the OLED device of Examples 1 to 43 and Comparative Examples 1 and 2. The vacuum degree during the deposition was maintained at 110.sup.6 to 310.sup.7 torr. Herein, the ITO substrate was deposited with a first hole injection layer (HIL-1), a second hole injection layer (HIL-2), a hole transporting layer (HTL), a green/red emission layer (GEL/REL), an electron transporting layer (ETL), an electron injection layer (EIL), and a cathode (Cthd).

[0144] Herein, HI was a material for forming HIL-1 and HIL-2; HI-D was a material for forming HIL-1. HT was material for forming HTL; ET was material for forming ETL. Liq was a material for forming ETL and EIL. Compositions 1 to 53 were respectively a material of GHRH for forming GEL/REL, and GD/RD were respectively a dopant for forming GEL/REL. The main difference of the OLEDs between the Examples and Comparative Example was that the GEL/REL of the OLED in the following comparative example was made of the Compositions 52 and 53 containing TPBi but the GEL/REL of OLED in the following examples was made of Compositions 1 to 51 of the present invention listed in Table 5. The detailed chemical structure of foresaid commercial material was listed in Table 7.

TABLE-US-00009 TABLE 7 chemical structures of commercial materials for OLED devices [00478] [00479] [00480] [00481] [00482] [00483] [00484] [00485]

[0145] Preparation of Green OLED Devices

[0146] To prepare the green OLED device, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 8, and the materials and the thicknesses of the organic layers in green OLED devices were also listed in Table 8.

TABLE-US-00010 TABLE 8 coating sequence, materials and thickness of the organic layers in green OLED device Coating Sequence Layer Material Thickness 1 HIL-1 HI doped with 3.0 wt % of HI-D 100 2 HIL-2 HI 1400 3 HTL HT 100 4 GEL Composition for GH doped with 10.0 400 wt % of GD 5 ETL ET doped with 35.0 wt % of Liq 350 6 EIL Liq 15 7 Cthd Al 1500

[0147] Preparation of Red OLED Devices

[0148] To prepare the red OLED device, multiple organic layers were respectively deposited on the ITO substrate according to the sequence as listed in Table 9, and the materials and the thicknesses of the organic layers in red OLED devices were also listed in Table 9.

TABLE-US-00011 TABLE 9 coating sequence, materials and thickness of the organic layers in red OLED device Coating Sequence Layer Material Thickness 1 HIL-1 HI doped with 3.0 wt % of HI-D 100 2 HIL-2 HI 2200 3 HTL HT 100 4 REL Composition for RH doped with 3.5 300 wt % of RD 5 ETL ET doped with 35.0 wt % of Liq 350 6 EIL Liq 15 7 Cthd Al 1500

[0149] Performance of OLED Devices

[0150] 1. Color Coordinates (x,y), Driving Voltage and Current Efficiency

[0151] To evaluate the performance of OLED devices, the green or red OLED devices were measured by PR650 as photometer and Keithley 2400 as power supply. Color coordinates (x,y) were determined according to the CIE chromaticity scale (Commission Internationale de L'Eclairage, 1931). The results were shown in Tables 10 and 11. For the green OLED devices, the data were collected with a specific luminance at 9000 nits. For the red OLED devices, the data were collected with a specific luminance at 3000 nits.

[0152] Characteristics of manufactured OLED devices of Examples 1 to 43 and Comparative Examples 1 and 2 were measured by the following method.

[0153] (1). Measurement of the Current Density Change Depending on Voltage Change

[0154] Current values flowing in the devices of the OLEDs were measured, while increasing the voltage from 0V to 6.2V by using the power supply, and the current value of each voltage was measured.

[0155] (2). Measurement of the Luminance Change Depending on Voltage Change

[0156] Luminance of the manufactured OLEDs was measured by the photometer, while increasing the voltage from 0V to 6.2V by using the power supply. [0157] (3). Measurement of Current Efficiency

[0158] Current efficiency (cd/A) was calculated by using the luminance and current density obtained in aforesaid items (1) and (2). [0159] (4). Measurement of Color Coordinates (x,y)

[0160] Color coordinates (x,y) were determined according to the CIE chromaticity scale. CIE (x,y) changes depended on voltage from 0V to 6.2V, which were recorded by the photometer.

[0161] Compositions 1 to 4, 6, 8, 9, 11, 15, 18, 20 to 29, 31, 33, 35 to 38, 40 to 43, 45 to 51 were respectively used for GH in the GEL of green OLEDs of Examples 1 to 37. Composition 53 was used for GH in the GEL of the green OLED of Comparative Example 1. The composition for GH, and data of CIE, driving voltage and current efficiency of Examples 1 to 37 and Comparative Example 1 were listed in Table 10.

TABLE-US-00012 TABLE 10 Compositions for GH, CIEs, driving voltages, and current efficiencies of green OLED devices of Examples 1 to 37 and Comparative Example 1 Composition Driving Current Example No. CIE voltage efficiency No. for GH (x, y) (V) (cd/A) Example 1 1 (0.316, 0.632) 5.24 67.3 Example 2 2 (0.319,0.630) 4.18 68.6 Example 3 3 (0.319, 0.629) 4.45 66.6 Example 4 4 (0.322, 0.629) 4.72 68.8 Example 5 6 (0.314, 0.632) 5.18 61.8 Example 6 8 (0.318, 0.628) 4.60 64.1 Example 7 9 (0.322, 0.628) 4.22 62.3 Example 8 11 (0.328, 0.627) 4.74 73.2 Example 9 15 (0.317, 0.634) 4.29 71.8 Example 10 18 (0.356, 0.598) 5.41 58.6 Example 11 20 (0.314, 0.635) 4.58 63.9 Example 12 21 (0.323, 0.629) 4.14 69.2 Example 13 22 (0.330, 0.625) 4.22 70.2 Example 14 23 (0.317, 0.632) 4.62 66.8 Example 15 24 (0.314, 0.635) 4.59 70.4 Example 16 25 (0.324, 0.630) 4.63 70.7 Example 17 26 (0.313, 0.635) 4.55 70.0 Example 18 27 (0.316, 0.634) 4.40 72.3 Example 19 28 (0.318, 0.629) 4.45 65.2 Example 20 29 (0.320, 0.627) 4.53 61.5 Example 21 31 (0.317,0.631) 4.55 65.2 Example 22 33 (0.315, 0.631) 4.34 62.3 Example 23 35 (0.321, 0.625) 5.75 58.9 Example 24 36 (0.318, 0.629) 4.35 66.7 Example 25 37 (0.318, 0.628) 4.14 62.7 Example 26 38 (0.312, 0.633) 4.53 65.5 Example 27 40 (0.317, 0.630) 5.24 61.0 Example 28 41 (0.317, 0.629) 4.70 59.9 Example 29 42 (0.320, 0.627) 4.62 63.0 Example 30 43 (0.322, 0.631) 4.37 72.4 Example 31 45 (0.319, 0.627) 4.46 62.9 Example 32 46 (0.322, 0.627) 4.34 63.7 Example 33 47 (0.316, 0.630) 5.39 61.8 Example 34 48 (0.323, 0.629) 4.23 68.2 Example 35 49 (0.317, 0.633) 4.37 76.1 Example 36 50 (0.331, 0.626) 4.28 73.7 Example 37 51 (0.319, 0.633) 4.91 68.1 Comparative 53 (0.313, 0.634) 6.30 47.2 Example 1

[0162] Compositions 5, 7, 10, 12, 19 and 44 were respectively used for RH in the REL of red OLEDs of Examples 38 to 43. Composition 53 was used for RH in the REL of the red OLED of Comparative Example 2. The composition for RH, and data of CIE, driving voltage and current efficiency of Examples 38 to 43 and Comparative Example 2 were listed in Table 11.

TABLE-US-00013 TABLE 11 Compositions for RH, CIEs, driving voltages, and current efficiencies of red OLED devices of Examples 38 to 43 and Comparative Example 2 Driving Current Example Composition CIE voltage efficiency No. No. for RH (x, y) (V) (cd/A) Example 38 5 (0.660, 0.338) 4.05 27.3 Example 39 7 (0.665, 0.333) 4.31 27.0 Example 40 10 (0.660, 0.338) 4.31 28.7 Example 41 12 (0.661, 0.337) 4.40 26.0 Example 42 19 (0.661, 0.336) 4.74 28.7 Example 43 44 (0.661, 0.336) 4.53 28.2 Comparative 53 (0.658, 0.339) 5.80 17.5 Example 2

[0163] 2. Measurement of Lifespan (T95)

[0164] Lifespan (T95) was measured by OLED life time test system (Chroma model 58131). T95 represents lifespan data evaluating a period taken for luminance to reach 95% with respect to the initial luminance (at 7,000 nits for green OLEDs and at 6000 nits for red OEDs).

[0165] The composition for GH and the lifespan of Examples 1 to 7, 12, 13, 18, 29 to 34, 36 and 37 and Comparative Example 1 were listed in Table 12.

TABLE-US-00014 TABLE 12 Compositions for GH and lifespan of green OLED devices of Examples 1 to 7, 12, 13, 18, 29 to 34, 36 and 37 and Comparative Example 1 Example Composition Lifespan (T95) No. No. (hrs) Example 1 1 90 Example 2 2 104 Example 3 3 47 Example 4 4 81 Example 5 6 65 Example 6 8 61 Example 7 9 112 Example 12 21 40 Example 13 22 20 Example 18 27 44 Example 29 42 112 Example 30 43 30 Example 31 45 87 Example 32 46 98 Example 33 47 56 Example 34 48 52 Example 36 50 68 Example 37 51 20 Comparative Example 1 53 1

[0166] The composition for RH and the lifespan of Examples 38, 39, 41 and 43 and Comparative Example 1 were listed in Table 13.

TABLE-US-00015 TABLE 13 Compositions for RH and lifespan of red OLED devices of Examples 38, 39, 41 and 43 and Comparative Example 2 Example Composition Lifespan (T95) No. No. (hrs) Example 38 5 32 Example 39 7 17 Example 41 12 16 Example 43 44 14 Comparative Example 2 53 0.5

[0167] Based on the results, in comparison with the Composition 53 containing the commercial host material for the green emission layer, adopting Compositions 1 to 4, 6, 8, 9, 11, 15, 18, 20 to 29, 31, 33, 35 to 38, 40 to 43, 45 to 51 of the present invention as the host material for the green emission layer can reduced the driving voltage and improve the current efficiency of the green OLEDs. Similarly, in comparison with the Composition 53 containing the commercial host material for the red emission layer, adopting Compositions 5, 7, 10, 12, 19 and 44 of the present invention as the host material for the red emission layer also can reduce the driving voltage and improve the current efficiency of the red OLEDs.

[0168] Even more, adopting Compositions 1 to 4, 6, 8, 9, 21, 22, 27, 42, 43, 45 to 48, 50 and 51 of the present invention as the host material for the green emission layer can prolong the lifespan of the green OLEDs. Similarly, adopting Compositions 5, 7, 12 and 44 of the present invention as the host material for the red emission layer can prolong the lifespan of the red OLEDs.

[0169] The reason is that the specific first host compounds had a suitable lowest unoccupied molecular orbital (LUMO) level for the better electron injection to the EL compared to TPBi of Comparative example, leading to the lower driving voltage. In addition, the cooperation of the specific first and second host compounds would respectively form an exciplex as shown in Table 6, and such emission mechanism can effectively use the exciton to lead the high efficiency devices.

[0170] It demonstrated that the composition of the present invention is suitable as a host material for any green or red OLEDs, and allows the OLEDs using the same to have low driving voltage and improved current efficiency, and even prolonged lifespan.

[0171] Even though numerous characteristics and advantages of the present invention have been set forth in the foregoing description, together with details of the structure and features of the invention, the disclosure is illustrative only. Changes may be made in the details, especially in matters of shape, size, and arrangement of parts within the principles of the invention to the full extent indicated by the broad general meaning of the terms in which the appended claims are expressed.