SILICON-CONTAINING ELECTRON TRANSPORTING MATERIAL AND ITS APPLICATION

Abstract

A silicon-containing electron transporting material and its application are disclosed. The silicon-containing electron transporting material employs a silicon-containing compound with a novel structure containing one or more silicon atoms and a specific group. The compound can be used as an electron transporting layer of an electroluminescent device, which can effectively improve the lifetime of the device and improve device performance. An electroluminescent device and compound formulation are also disclosed.

Claims

1. A compound having Formula 1:
AL-B).sub.n Formula 1 wherein n is 1, 2, 3 or 4; when n is greater than or equal to 2, each group of L and B can be the same or different; A is the structure represented by Formula 2: ##STR00076## wherein ring X and Y each independently represents a substituted or unsubstituted aryl or heteroaryl group having 5 to 50 ring atoms; wherein at least one of X and Y is a fused ring system; wherein R.sub.1 and R.sub.2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; wherein R.sub.1 and R.sub.2 can be optionally joined to form a ring; wherein L is a single bond, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; wherein B is a substituted or unsubstituted electron-deficient heteroaryl group having 2 to 60 carbon atoms.

2. The compound of claim 1, wherein at least one of X and Y in Formula 2 is a fused ring system, wherein the fused ring system is formed by fusing at least two aryl and/or heteroaryl rings together to form a fused ring system containing at least 10 carbon atoms, or a fused ring system containing at least 10 carbon atoms and nitrogen atoms in total; or, wherein at least one of X and Y in Formula 2 is a fused ring system, wherein the fused ring system is formed by fusing at least three aryl and/or heteroaryl rings together to form a fused ring system containing at least 14 carbon atoms, or a fused ring system containing at least 14 carbon atoms and nitrogen atoms in total.

3. The compound of claim 1, wherein A is selected from the group consisting of Formula 3 to Formula 33: ##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083## wherein T.sub.1 to T.sub.22 are each independently selected from CR.sub.T, C or N; wherein each of the R.sub.T is independently selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; adjacent substituents can be optionally joined to form a ring.

4. The compound of claim 1, when R.sub.1 and R.sub.2 are joined to form a ring, the substituents R.sub.1 and R.sub.2 in the compound are each independently selected from an electron neutral group or an electron deficient group.

5. The compound of claim 1, wherein R.sub.1 and R.sub.2 in Formula 2 are not joined to form a ring; preferably, in the structures represented by the Formula 3 to the Formula 33, T.sub.5 and T.sub.6 are not joined to form a ring.

6. The compound of claim 4, wherein R.sub.1 and R.sub.2 in Formula 2 are not joined to form a ring; preferably, in the structures represented by the Formula 3 to the Formula 33, T.sub.5 and T.sub.6 are not joined to form a ring.

7. The compound of claim 1, wherein the structure of L is selected from the group consisting of a single bond and the Formula 34 to Formula 58: ##STR00084## ##STR00085## ##STR00086## wherein R.sub.3, R.sub.4, R.sub.5 and R.sub.6 each independently represent a mono-substitution, multiple substitutions or no substitution; when they represent multiple substitutions, adjacent substituents can be optionally joined to form a ring; wherein R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each independently selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

8. The compound of claim 1, wherein B is selected from the group consisting of Formula 59 to Formula 63: ##STR00087## wherein X.sub.1 to X.sub.6 are each independently selected from CR.sub.x, C, O, S, N or NR.sub.x; wherein at least one of X.sub.1 to X.sub.i is N, or wherein at least two of X.sub.1 to X.sub.i are N, or at least three of X.sub.1 to X.sub.i are N; wherein X.sub.i represents one with the largest sequence number among X.sub.1 to X.sub.6 existing in Formula 59 to Formula 63; wherein R.sub.7 each independently represents a mono-substitution, multiple substitutions or no substitution; when they represent multiple substitutions, adjacent substituents can be optionally joined to form a ring; wherein R.sub.7, R.sub.x, and R.sub.x are each independently selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

9. The compound of claim 1, wherein B is independently selected from the group consisting of B.sub.1 to B.sub.105: ##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095## ##STR00096## ##STR00097## ##STR00098## ##STR00099## ##STR00100## ##STR00101## ##STR00102## ##STR00103## ##STR00104## ##STR00105## ##STR00106## ##STR00107## ##STR00108##

10. The compound of claim 1, wherein A is independently selected from the group consisting of A.sub.1 to A.sub.298: ##STR00109## ##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162## ##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167## ##STR00168## ##STR00169## ##STR00170## ##STR00171##

11. The compound of claim 9, wherein A is independently selected from the group consisting of A.sub.1 to A.sub.298: ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192## ##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197## ##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202## ##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207## ##STR00208## ##STR00209## ##STR00210## ##STR00211## ##STR00212## ##STR00213## ##STR00214## ##STR00215## ##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220## ##STR00221## ##STR00222## ##STR00223## ##STR00224## ##STR00225## ##STR00226## ##STR00227## ##STR00228## ##STR00229## ##STR00230## ##STR00231## ##STR00232## ##STR00233## ##STR00234##

12. The compound of claim 1, wherein L is independently selected from the group consisting of a single bond L.sub.0 and L.sub.1 to L.sub.58: ##STR00235## ##STR00236## ##STR00237## ##STR00238## ##STR00239## ##STR00240##

13. The compound of claim 11, wherein L is independently selected from the group consisting of a single bond L.sub.0 and L.sub.1 to L.sub.58: ##STR00241## ##STR00242## ##STR00243## ##STR00244## ##STR00245## ##STR00246##

14. The compound of claim 13, wherein the compound has a structure represented by Formula 1, wherein each A is independently selected from the group consisting of A.sub.1 to A.sub.298, each B is independently selected from the group consisting of B.sub.1 to B.sub.105, each L is independently selected from the group consisting of L.sub.0 to L.sub.58.

15. The compound of claim 14, wherein the compound has a structure represented by Formula 1, wherein A, L, B, n are independently correspond to the substituents and numbers shown in the table below: TABLE-US-00007 Compound No. A L B n 1 A26 L0 B18 1 2 A26 L0 B19 1 3 A26 L0 B20 1 4 A26 L0 B21 1 5 A26 L0 B22 1 6 A26 L0 B23 1 7 A26 L0 B24 1 8 A26 L0 B27 1 9 A26 L0 B28 1 10 A26 L0 B29 1 11 A26 L0 B30 1 12 A26 L0 B31 1 13 A26 L0 B32 1 14 A26 L0 B33 1 15 A26 L0 B34 1 16 A26 L0 B51 1 17 A26 L0 B52 1 18 A26 L0 B53 1 19 A26 L0 B54 1 20 A26 L0 B55 1 21 A26 L0 B56 1 22 A26 L0 B59 1 23 A26 L0 B60 1 24 A26 L0 B61 1 25 A26 L0 B62 1 26 A26 L0 B63 1 27 A26 L0 B64 1 28 A26 L0 B65 1 29 A26 L0 B66 1 30 A26 L0 B92 1 31 A26 L1 B18 1 32 A26 L1 B19 1 33 A26 L1 B20 1 34 A26 L1 B21 1 35 A26 L1 B22 1 36 A26 L1 B23 1 37 A26 L1 B24 1 38 A26 L1 B27 1 39 A26 L1 B28 1 40 A26 L1 B29 1 41 A26 L1 B30 1 42 A26 L1 B31 1 43 A26 L1 B32 1 44 A26 L1 B33 1 45 A26 L1 B34 1 46 A26 L1 B51 1 47 A26 L1 B52 1 48 A26 L1 B53 1 49 A26 L1 B54 1 50 A26 L1 B55 1 51 A26 L1 B56 1 52 A26 L1 B59 1 53 A26 L1 B60 1 54 A26 L1 B61 1 55 A26 L1 B62 1 56 A26 L1 B63 1 57 A26 L1 B64 1 58 A26 L1 B65 1 59 A26 L1 B66 1 60 A26 L1 B92 1 61 A26 L2 B18 1 62 A26 L2 B19 1 63 A26 L2 B20 1 64 A26 L2 B21 1 65 A26 L2 B22 1 66 A26 L2 B23 1 67 A26 L2 B24 1 68 A26 L2 B27 1 69 A26 L2 B28 1 70 A26 L2 B29 1 71 A26 L2 B30 1 72 A26 L2 B31 1 73 A26 L2 B32 1 74 A26 L2 B33 1 75 A26 L2 B34 1 76 A26 L2 B51 1 77 A26 L2 B52 1 78 A26 L2 B53 1 79 A26 L2 B54 1 80 A26 L2 B55 1 81 A26 L2 B56 1 82 A26 L2 B59 1 83 A26 L2 B60 1 84 A26 L2 B61 1 85 A26 L2 B62 1 86 A26 L2 B63 1 87 A26 L2 B64 1 88 A26 L2 B65 1 89 A26 L2 B66 1 90 A26 L2 B92 1 91 A29 L0 B18 1 92 A29 L0 B19 1 93 A29 L0 B20 1 94 A29 L0 B21 1 95 A29 L0 B22 1 96 A29 L0 B23 1 97 A29 L0 B24 1 98 A29 L0 B27 1 99 A29 L0 B28 1 100 A29 L0 B29 1 101 A29 L0 B30 1 102 A29 L0 B31 1 103 A29 L0 B32 1 104 A29 L0 B33 1 105 A29 L0 B34 1 106 A29 L0 B51 1 107 A29 L0 B52 1 108 A29 L0 B53 1 109 A29 L0 B54 1 110 A29 L0 B55 1 111 A29 L0 B56 1 112 A29 L0 B59 1 113 A29 L0 B60 1 114 A29 L0 B61 1 115 A29 L0 B62 1 116 A29 L0 B63 1 117 A29 L0 B64 1 118 A29 L0 B65 1 119 A29 L0 B66 1 120 A29 L0 B92 1 121 A29 L1 B18 1 122 A29 L1 B19 1 123 A29 L1 B20 1 124 A29 L1 B21 1 125 A29 L1 B22 1 126 A29 L1 B23 1 127 A29 L1 B24 1 128 A29 L1 B27 1 129 A29 L1 B28 1 130 A29 L1 B29 1 131 A29 L1 B30 1 132 A29 L1 B31 1 133 A29 L1 B32 1 134 A29 L1 B33 1 135 A29 L1 B34 1 136 A29 L1 B51 1 137 A29 L1 B52 1 138 A29 L1 B53 1 139 A29 L1 B54 1 140 A29 L1 B55 1 141 A29 L1 B56 1 142 A29 L1 B59 1 143 A29 L1 B60 1 144 A29 L1 B61 1 145 A29 L1 B62 1 146 A29 L1 B63 1 147 A29 L1 B64 1 148 A29 L1 B65 1 149 A29 L1 B66 1 150 A29 L1 B92 1 151 A29 L2 B18 1 152 A29 L2 B19 1 153 A29 L2 B20 1 154 A29 L2 B21 1 155 A29 L2 B22 1 156 A29 L2 B23 1 157 A29 L2 B24 1 158 A29 L2 B27 1 159 A29 L2 B28 1 160 A29 L2 B29 1 161 A29 L2 B30 1 162 A29 L2 B31 1 163 A29 L2 B32 1 164 A29 L2 B33 1 165 A29 L2 B34 1 166 A29 L2 B51 1 167 A29 L2 B52 1 168 A29 L2 B53 1 169 A29 L2 B54 1 170 A29 L2 B55 1 171 A29 L2 B56 1 172 A29 L2 B59 1 173 A29 L2 B60 1 174 A29 L2 B61 1 175 A29 L2 B62 1 176 A29 L2 B63 1 177 A29 L2 B64 1 178 A29 L2 B65 1 179 A29 L2 B66 1 180 A29 L2 B92 1 181 A30 L0 B18 1 182 A30 L0 B19 1 183 A30 L0 B20 1 184 A30 L0 B21 1 185 A30 L0 B22 1 186 A30 L0 B23 1 187 A30 L0 B24 1 188 A30 L0 B27 1 189 A30 L0 B28 1 190 A30 L0 B29 1 191 A30 L0 B30 1 192 A30 L0 B31 1 193 A30 L0 B32 1 194 A30 L0 B33 1 195 A30 L0 B34 1 196 A30 L0 B51 1 197 A30 L0 B52 1 198 A30 L0 B53 1 199 A30 L0 B54 1 200 A30 L0 B55 1 201 A30 L0 B56 1 202 A30 L0 B59 1 203 A30 L0 B60 1 204 A30 L0 B61 1 205 A30 L0 B62 1 206 A30 L0 B63 1 207 A30 L0 B64 1 208 A30 L0 B65 1 209 A30 L0 B66 1 210 A30 L0 B92 1 211 A30 L1 B18 1 212 A30 L1 B19 1 213 A30 L1 B20 1 214 A30 L1 B21 1 215 A30 L1 B22 1 216 A30 L1 B23 1 217 A30 L1 B24 1 218 A30 L1 B27 1 219 A30 L1 B28 1 220 A30 L1 B29 1 221 A30 L1 B30 1 222 A30 L1 B31 1 223 A30 L1 B32 1 224 A30 L1 B33 1 225 A30 L1 B34 1 226 A30 L1 B51 1 227 A30 L1 B52 1 228 A30 L1 B53 1 229 A30 L1 B54 1 230 A30 L1 B55 1 231 A30 L1 B56 1 232 A30 L1 B59 1 233 A30 L1 B60 1 234 A30 L1 B61 1 235 A30 L1 B62 1 236 A30 L1 B63 1 237 A30 L1 B64 1 238 A30 L1 B65 1 239 A30 L1 B66 1 240 A30 L1 B92 1 241 A30 L2 B18 1 242 A30 L2 B19 1 243 A30 L2 B20 1 244 A30 L2 B21 1 245 A30 L2 B22 1 246 A30 L2 B23 1 247 A30 L2 B24 1 248 A30 L2 B27 1 249 A30 L2 B28 1 250 A30 L2 B29 1 251 A30 L2 B30 1 252 A30 L2 B31 1 253 A30 L2 B32 1 254 A30 L2 B33 1 255 A30 L2 B34 1 256 A30 L2 B51 1 257 A30 L2 B52 1 258 A30 L2 B53 1 259 A30 L2 B54 1 260 A30 L2 B55 1 261 A30 L2 B56 1 262 A30 L2 B59 1 263 A30 L2 B60 1 264 A30 L2 B61 1 265 A30 L2 B62 1 266 A30 L2 B63 1 267 A30 L2 B64 1 268 A30 L2 B65 1 269 A30 L2 B66 1 270 A30 L2 B92 1

16. An electroluminescent device comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having Formula 1:
AL-B).sub.n Formula 1 wherein n is 1, 2, 3 or 4; when n is greater than or equal to 2, each group of L and B can be the same or different; A has the structure represented by Formula 2: ##STR00247## wherein ring X and Y each independently represents a substituted or unsubstituted aryl or heteroaryl group having 5 to 50 ring atoms; wherein at least one of X and Y is a fused ring system; wherein R.sub.1 and R.sub.2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof: wherein R.sub.1 and R.sub.2 can be optionally joined to form a ring; wherein L is a single bond, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; wherein B is a substituted or unsubstituted electron-deficient heteroaryl group having 2 to 60 carbon atoms.

17. The electroluminescent device of claim 16, wherein the organic layer is an electron transporting layer.

18. The electroluminescent device of claim 17, wherein the electron transporting layer also comprises at least one material; preferably, wherein the electron transporting layer also comprises at least one metal complex; preferably, wherein the metal complex comprises a ligand L.sub.q represented by Formula 64: ##STR00248## wherein Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, Y.sub.5 and Y.sub.6 are each independently selected from CR.sub.Y or N; wherein each of R.sub.Y is independently selected from hydrogen, deuterium, alkyl, alkoxy, amino, silyl, cyano, halogen, aryl and heteroaryl; wherein Z is N, O, S or Se; preferably, wherein the metal complex is 8-hydroxyquinoline-lithium, 8-hydroxyquinoline-sodium, 8-hydroxyquinoline-potassium (Kq), bis(8-hydroxyquinoline)-beryllium (Beq.sub.2), Bis(8-hydroxyquinoline)-magnesium (Mgq.sub.2), bis(8-hydroxyquinoline)-calcium (Caq.sub.2), tris(8-hydroxyquinoline)-boron (Bq.sub.3), tris(8-hydroxyquinoline)-Aluminum, or tris(8-hydroxyquinoline)-gallium.

19. The electroluminescent device of claim 16, wherein the electroluminescent device is incorporated into a device group consisting of a consumer product, an electronic component module, an organic light emitting device and a lighting panel.

20. A compound formulation comprising the compound of claim 1.

Description

4 BRIEF DESCRIPTION OF THE DRAWINGS

[0026] FIG. 1 schematically shows an organic light emitting device that can incorporate the compound or compound formulation disclosed herein.

[0027] FIG. 2 schematically shows another organic light emitting device that can incorporate the compound or compound formulation disclosed herein.

[0028] FIG. 3 shows the structural Formula 1 of the compound disclosed herein.

5 DETAILED DESCRIPTION

[0029] OLEDs can be fabricated on various types of substrates such as glass, plastic, and metal foil. FIG. 1 schematically shows the organic light emitting device 100 without limitation. The figures are not necessarily drawn to scale. Some of the layers in the figures can also be omitted as needed. Device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, an emissive layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. Device 100 may be fabricated by depositing the layers described in order. The properties and functions of these various layers, as well as example materials, are described in more detail in U.S. Pat. No. 7,279,704 at cols. 6-10, the contents of which are incorporated by reference herein in its entirety.

[0030] More examples for each of these layers are available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference herein in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F.sub.4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference herein in its entirety. Examples of host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al., which is incorporated by reference herein in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference herein in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference herein in their entireties, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, electrically-conductive, sputter-deposited ITO layer. The theory and use of blocking layers is described in more detail in U.S. Pat. No. 6,097,147 and U.S. Patent Application Publication No. 2003/0230980, which are incorporated by reference herein in their entireties. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference herein in its entirety. A description of protective layers may be found in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference herein in its entirety.

[0031] The layered structure described above is provided by way of non-limiting example. Functional OLEDs may be achieved by combining the various layers described in different ways, or layers may be omitted entirely. It may also include other layers not specifically described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimum performance. Any functional layer may include several sublayers. For example, the emissive layer may have two layers of different emitting materials to achieve desired emission spectrum.

[0032] In one embodiment, an OLED may be described as having an organic layer disposed between a cathode and an anode. This organic layer may comprise a single layer or multiple layers.

[0033] An OLED can be encapsulated by a barrier layer. FIG. 2 schematically shows the organic light emitting device 200 without limitation. FIG. 2 differs from FIG. 1 in that the organic light emitting device include a barrier layer 102, which is above the cathode 190, to protect it from harmful species from the environment such as moisture and oxygen. Any material that can provide the barrier function can be used as the barrier layer such as glass and organic-inorganic hybrid layers. The barrier layer should be placed directly or indirectly outside of the OLED device. Multilayer thin film encapsulation was described in U.S. Pat. No. 7,968,146, which is herein incorporated by reference in its entirety.

[0034] Devices fabricated in accordance with embodiments of the present disclosure can be incorporated into a wide variety of consumer products that have one or more of the electronic component modules (or units) incorporated therein. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablets, phablets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicles displays, and vehicle tail lights.

[0035] The materials and structures described herein may be used in other organic electronic devices listed above.

[0036] As used herein, top means furthest away from the substrate, while bottom means closest to the substrate. Where a first layer is described as disposed over a second layer, the first layer is disposed further away from substrate. There may be other layers between the first and second layer, unless it is specified that the first layer is in contact with the second layer. For example, a cathode may be described as disposed over an anode, even though there are various organic layers in between.

[0037] As used herein, solution processable means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.

[0038] A ligand may be referred to as photoactive when it is believed that the ligand directly contributes to the photoactive properties of an emissive material. A ligand may be referred to as ancillary when it is believed that the ligand does not contribute to the photoactive properties of an emissive material, although an ancillary ligand may alter the properties of a photoactive ligand.

[0039] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistics limit through delayed fluorescence. As used herein, there are two types of delayed fluorescence, i.e. P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated from triplet-triplet annihilation (TTA).

[0040] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but rather on the transition between the triplet states and the singlet excited states. Compounds that are capable of generating E-type delayed fluorescence are required to have very small singlet-triplet gaps to convert between energy states. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as thermally activated delayed fluorescence (TADF). A distinctive feature of TADF is that the delayed component increases as temperature rises. If the reverse intersystem crossing rate is fast enough to minimize the non-radiative decay from the triplet state, the fraction of back populated singlet excited states can potentially reach 75%. The total singlet fraction can be 100%, far exceeding 25% of the spin statistics limit for electrically generated excitons.

[0041] E-type delayed fluorescence characteristics can be found in an exciplex system or in a single compound. Without being bound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (E.sub.S-T). Organic, non-metal containing, donor-acceptor luminescent materials may be able to achieve this. The emission in these materials is often characterized as a donor-acceptor charge-transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds often results in small E.sub.S-T. These states may involve CT states. Often, donor-acceptor luminescent materials are constructed by connecting an electron donor moiety such as amino- or carbazole-derivatives and an electron acceptor moiety such as N-containing six-membered aromatic rings.

Definition of Terms of Substituents

[0042] Halogen or halideas used herein includes fluorine, chlorine, bromine, and iodine.

[0043] Alkylcontemplates both straight and branched chain alkyl groups. Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, and 3-methylpentyl group. Additionally, the alkyl group may be optionally substituted. The carbons in the alkyl chain can be replaced by other hetero atoms. Of the above, preferred are methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, and neopentyl group.

[0044] Cycloalkylas used herein contemplates cyclic alkyl groups. Preferred cycloalkyl groups are those containing 4 to 10 ring carbon atoms and includes cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcylcohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. Additionally, the cycloalkyl group may be optionally substituted. The carbons in the ring can be replaced by other hetero atoms.

[0045] Alkenylas used herein contemplates both straight and branched chain alkene groups. Preferred alkenyl groups are those containing 2 to 15 carbon atoms. Examples of the alkenyl group include vinyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butandienyl group, 1-methylvinyl group, styryl group, 2,2-diphenylvinyl group, 1,2-diphenylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 2-phenylallyl group, 3-phenylallyl group, 3,3-diphenylallyl group, 1,2-dimethylallyl group, 1-phenyl1-butenyl group, and 3-phenyl-1-butenyl group. Additionally, the alkenyl group may be optionally substituted.

[0046] Alkynylas used herein contemplates both straight and branched chain alkyne groups. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. Additionally, the alkynyl group may be optionally substituted.

[0047] Aryl or aromatic groupas used herein includes noncondensed and condensed systems. Preferred aryl groups are those containing six to sixty carbon atoms, preferably six to twenty carbon atoms, more preferably six to twelve carbon atoms. Examples of the aryl group include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Additionally, the aryl group may be optionally substituted. Examples of the non-condensed aryl group include phenyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group, p-(2-phenylpropyl)phenyl group, 4-methylbiphenylyl group, 4-t-butyl p-terphenyl-4-yl group, o-cumenyl group, m-cumenyl group, p-cumenyl group, 2,3-xylyl group, 3,4-xylyl group, 2,5-xylyl group, mesityl group, and m-quaterphenyl group.

[0048] Heterocyclic group or heterocycleas used herein includes aromatic and non-aromatic cyclic groups. Hetero-aromatic also means heteroaryl. Preferred non-aromatic heterocyclic groups are those containing 3 to 7 ring atoms which include at least one hetero atom such as nitrogen, oxygen, and sulfur. The heterocyclic group can also be an aromatic heterocyclic group having at least one heteroatom selected from nitrogen atom, oxygen atom, sulfur atom, and selenium atom.

[0049] Heteroarylas used herein includes noncondensed and condensed hetero-aromatic groups that may include from one to five heteroatoms. Preferred heteroaryl groups are those containing three to thirty carbon atoms, preferably three to twenty carbon atoms, more preferably three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazinc, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine, and aza-analogs thereof. Additionally, the heteroaryl group may be optionally substituted.

[0050] Alkoxyit is represented by O-Alkyl. Examples and preferred examples thereof are the same as those described above. Examples of the alkoxy group having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, and hexyloxy group. The alkoxy group having 3 or more carbon atoms may be linear, cyclic or branched.

[0051] Aryloxyit is represented by O-Aryl or O-heteroaryl. Examples and preferred examples thereof are the same as those described above. Examples of the aryloxy group having 6 to 40 carbon atoms include phenoxy group and biphenyloxy group.

[0052] Arylalkylas used herein contemplates an alkyl group that has an aryl substituent. Additionally, the arylalkyl group may be optionally substituted. Examples of the arylalkyl group include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, alpha.-naphthylmethyl group, 1-alpha.-naphthylethyl group, 2-alpha-naphthylethyl group, 1-alpha-naphthylisopropyl group, 2-alpha-naphthylisopropyl group, beta-naphthylmethyl group, l-beta-naphthylethyl group, 2-beta-naphthylethyl group, 1-beta-naphthylisopropyl group, 2-beta-naphthylisopropyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, and 1-chloro-2-phenylisopropyl group. Of the above, preferred are benzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, and 2-phenylisopropyl group.

[0053] The term aza in azadibenzofuran, aza-dibenzothiophene, etc. means that one or more of the CH groups in the respective aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylene encompasses dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline and other analogues with two or more nitrogens in the ring system. One of ordinary skill in the art can readily envision other nitrogen analogs of the aza-derivatives described above, and all such analogs are intended to be encompassed by the terms as set forth herein.

[0054] The alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, heterocyclic group, aryl, and heteroaryl may be unsubstituted or may be substituted with one or more substituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, arylalkyl, alkoxy, aryloxy, amino, cyclic amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, an acyl group, a carbonyl group, a carboxylic acid group, an ether group, an ester group, a nitrile group, an isonitrile group, a thiolalkyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0055] It is to be understood that when a molecular fragment is described as being a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g. phenyl, phenylene, naphthyl, dibenzofuryl) or as if it were the whole molecule (e.g. benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attached fragment are considered to be equivalent.

[0056] In the compounds mentioned in this disclosure, the hydrogen atoms can be partially or fully replaced by deuterium. Other atoms such as carbon and nitrogen, can also be replaced by their other stable isotopes. The replacement by other stable isotopes in the compounds may be preferred due to its enhancements of device efficiency and stability.

[0057] In the compounds mentioned in this disclosure, multiple substitutions refer to a range that includes a double substitution, up to the maximum available substitutions.

[0058] In the compounds mentioned in this disclosure, the expression that adjacent substituents can be optionally joined to form a ring is intended to be taken to mean that two radicals are linked to each other by a chemical bond. This is illustrated by the following scheme:

##STR00002##

[0059] Furthermore, the expression that adjacent substituents can be optionally joined to form a ring is also intended to be taken to mean that in the case where one of the two radicals represents hydrogen, the second radical is bonded at a position to which the hydrogen atom was bonded, with formation of a ring. This is illustrated by the following scheme:

##STR00003##

[0060] According to an embodiment of the present disclosure, a compound having Formula 1 is disclosed:

AL-B).sub.n Formula 1 [0061] wherein n is 1, 2, 3 or 4; when n2, each group of L and B can be the same or different;

[0062] A is the structure represented by Formula 2:

##STR00004## [0063] wherein ring X and Y each independently represents a substituted or unsubstituted aryl or heteroaryl group having 5 to 50 ring atoms; [0064] wherein at least one of X and Y is a fused ring system; [0065] wherein R.sub.1 and R.sub.2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; [0066] wherein R.sub.1 and R.sub.2 can be optionally joined to form a ring; [0067] wherein L is a single bond, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; [0068] wherein B is a substituted or unsubstituted electron-deficient heteroaryl group having 2 to 60 carbon atoms.

[0069] According to some embodiments of the present disclosure, wherein ring X and Y are each independently selected from a substituted or unsubstituted aryl or heteroaryl group having 5 to 40 ring atoms, or wherein ring X and Y are each independently selected from a substituted or unsubstituted aryl or heteroaryl group having 5 to 30 ring atoms, or wherein ring X and Y are each independently selected from a substituted or unsubstituted aryl or heteroaryl group having 5 to 20 ring atoms; [0070] wherein each L is independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms; or each L is independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms; or each L is independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms; or each L is independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms; [0071] wherein each B is independently selected from a substituted or unsubstituted electron-deficient heteroaryl group having 2 to 50 carbon atoms; or each B is independently selected from a substituted or unsubstituted electron-deficient heteroaryl group having 2 to 40 carbon atoms; or each B is independently selected from a substituted or unsubstituted electron-deficient heteroaryl group having 2 to 30 carbon atoms; or each B is independently selected from a substituted or unsubstituted electron-deficient heteroaryl group having 2 to 20 carbon atoms.

[0072] According to an embodiment of the present disclosure, wherein at least one of X and Y in Formula 2 is a fused ring system, wherein the fused ring system is formed by fusing at least two aryl and/or heteroaryl rings together to form a fused ring system containing at least 10 carbon atoms, or a fused ring system containing at least 10 carbon atoms and nitrogen atoms in total.

[0073] According to an embodiment of the present disclosure, wherein at least one of X and Y in Formula 2 is a fused ring system, wherein the fused ring system is formed by fusing at least three aryl and/or heteroaryl rings, to form a fused ring system containing at least 14 carbon atoms, or a fused ring system containing at least 14 carbon atoms and nitrogen atoms in total.

[0074] According to an embodiment of the present disclosure, wherein structure A is selected from the group consisting of Formula 3 to Formula 33:

##STR00005## ##STR00006## ##STR00007## ##STR00008## ##STR00009## ##STR00010## ##STR00011## [0075] wherein T.sub.1 to T.sub.22 are each independently selected from CR.sub.T, C or N; [0076] wherein each of the R.sub.T is independently selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; [0077] adjacent substituents can be optionally joined to form a ring. Adjacent substituents can be optionally joined to form a ring.

[0078] In this embodiment, adjacent substituents can be optionally joined to form a ring, both including the case where has a connection between the adjacent substituents R.sub.T in T.sub.1 to T.sub.22 to form a ring, and the case where adjacent substituents are all not connected to form a ring. This will be clearly understood by those skilled in the art.

[0079] According to an embodiment of the present disclosure, R.sub.1 and R.sub.2 in Formula 2 are not joined to form a ring. In a more specific embodiment, in the structure represented by the Formula 3 to the Formula 33, T.sub.5 and T.sub.6 are not joined to form a ring.

[0080] According to an embodiment of the present disclosure, R.sub.1 and R.sub.2 in Formula 2 are joined to form a ring.

[0081] In some embodiments of the present disclosure, since the disclosed compounds are designed as electron transporting materials, there is a very big difference from the compounds designed as luminescent materials. For example, the compounds of the present disclosure do not require any special design to make E(S1T1) of the compounds less than a certain value, for example 0.20 eV, and E(S1T1) of the compounds of the present disclosure may be greater than a certain value, for example 0.20 eV, 0.30 eV, 0.50 eV or a greater value. For another example, it is not necessary to select for comprising of an electron-rich group in the compounds of the present disclosure. For example, the substituents R.sub.1 and R.sub.2, which do not need to be selected to comprise an electron-rich group, can optionally comprise either an electrically neutral group or an electron deficient group.

[0082] According to an embodiment of the present disclosure, wherein the structure L is selected from the group consisting of a single bond and Formula 34 to Formula 58:

##STR00012## ##STR00013## ##STR00014## [0083] wherein R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each independently represent a mono-substitution, multiple substitutions or non-substitution; when they represent multiple substitutions, adjacent substituents can be optionally joined to form a ring; [0084] wherein R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each independently selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0085] In this embodiment, adjacent substituents can be optionally joined to form a ring, including both the case where has a connection between the adjacent substituents to form a ring, and the case where adjacent substituents are not joined to form a ring. This will be clearly understood by those skilled in the art.

[0086] According to an embodiment of the present disclosure, wherein the structure B is selected from the group consisting of Formula 59 to Formula 63:

##STR00015## [0087] wherein X.sub.1 to X.sub.6 are each independently selected from CR.sub.x, C, O, S, N or NR.sub.x; [0088] wherein at least one of X.sub.1 to X.sub.i is N, wherein X.sub.i corresponds to one with the largest sequence number among X.sub.1 to X.sub.6 existing in Formula 59 to Formula 63. For example, as for Formula 59, the X.sub.i corresponds to X.sub.3 which is the largest sequence number among the X.sub.1 to X.sub.6 existing in Formula 59. That is, at least one of X.sub.1 to X.sub.3 in the Formula 59 is N. [0089] wherein each of R.sub.7 is independently represent a mono-substitution, multiple substitutions or non-substitution; when they represent multiple substitutions, adjacent substituents can be optionally joined to form a ring; [0090] wherein R.sub.7, R.sub.x, and R.sub.x are each independently selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0091] In this embodiment, adjacent substituents can be optionally joined to form a ring, including both the case where has a connection between the adjacent substituents to form a ring, and the case where adjacent substituents are not joined to form a ring. This will be clearly understood by those skilled in the art.

[0092] According to an embodiment of the present disclosure, wherein structure B is selected from the group consisting of Formula 59 to Formula 63, wherein at least two of X.sub.1 to X.sub.i is N, wherein X.sub.i corresponds to the one with the largest sequence number among X.sub.1 to X.sub.6 existing in Formula 59 to Formula 63.

[0093] According to an embodiment of the present disclosure, wherein structure B is selected from the group consisting of Formula 59 to Formula 63, wherein at least three of X.sub.1 to X.sub.i is N, wherein X.sub.i corresponds to the one with the largest sequence number among X.sub.1 to X.sub.6 existing in Formula 59 to Formula 63.

[0094] According to an embodiment of the present disclosure, wherein the structure B is selected from the group consisting of B.sub.1 to B.sub.105:

##STR00016## ##STR00017## ##STR00018## ##STR00019## ##STR00020## ##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037##

[0095] According to an embodiment of the present disclosure, wherein the structure A is selected from the group consisting of A.sub.1 to A.sub.298. The A.sub.1 to A.sub.298 are referred to claim 10.

[0096] According to an embodiment of the present disclosure, wherein the structure L is selected from the group consisting of a single bond L.sub.0 and L.sub.1 to L.sub.58:

##STR00038## ##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044##

[0097] According to an embodiment of the present disclosure, wherein the compound has a structure of Formula 1, wherein the A is selected from the group consisting of A.sub.1-A.sub.298, wherein B is each independently selected from the group consisting of B.sub.1-B.sub.105, wherein L is each independently selected from the group consisting of L.sub.0-L.sub.58, the specific structure of A.sub.1-A.sub.298, B.sub.1-B.sub.105, and L.sub.0-L.sub.58 is shown in the foregoing embodiment.

[0098] According to an embodiment of the present disclosure, wherein the compound is selected from the group consisting of Compound 1 to Compound 270; the specific structure of the Compound 1 to Compound 270 is shown in claim 16.

[0099] According to an embodiment of the present disclosure, an electroluminescent device is disclosed, which comprises: [0100] an anode, [0101] a cathode, [0102] and an organic layer disposed between the anode and the cathode, wherein the organic layer comprising a compound having Formula 1:

AL-B).sub.n Formula 1 [0103] wherein n is 1, 2, 3 or 4; when n2, each group of L and B can be the same or different; [0104] A is the structure represented by Formula 2:

##STR00045## [0105] wherein ring X and Y each independently represents a substituted or unsubstituted aryl or heteroaryl group having 5 to 50 ring atoms; [0106] wherein at least one of X and Y is a fused ring system; [0107] wherein R.sub.1 and R.sub.2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; [0108] wherein R.sub.1 and R.sub.2 can be optionally joined to form a ring; [0109] wherein L is a single bond, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; [0110] wherein B is a substituted or unsubstituted electron-deficient heteroaryl group having 2 to 60 carbon atoms.

[0111] According to an embodiment of the present disclosure, wherein the organic layer is an electron transporting layer.

[0112] According to an embodiment of the present disclosure, wherein the organic layer is an electron transporting layer, the electron transporting layer further comprises at least one material.

[0113] According to an embodiment of the present disclosure, wherein the organic layer is an electron transporting layer, the electron transporting layer also comprises at least one metal complex.

[0114] According to an embodiment of the present disclosure, wherein the metal complex comprises a ligand L.sub.q represented by Formula 64:

##STR00046## [0115] wherein Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4, Y.sub.5 and Y.sub.6 are each independently selected from CR.sub.Y or N; wherein each R.sub.Y is independently selected from hydrogen, deuterium, alkyl, alkoxy, amino, silyl, cyano, halogen, aryl and heteroaryl; [0116] wherein Z is NH, O, S or Se.

[0117] According to an embodiment of the present disclosure, wherein the metal complex is 8-hydroxyquinoline-lithium (Liq), 8-hydroxyquinoline-sodium (Naq), 8-hydroxyquinoline-potassium (Kq), bis(8-hydroxyquinoline)-beryllium (Beq.sub.2), Bis(8-hydroxyquinoline)-magnesium (Mgq.sub.2), bis(8-hydroxyquinoline)-calcium (Caq.sub.2), tris(8-hydroxyquinoline)-boron (Bq.sub.3), tris(8-hydroxyquinoline)-aluminum (Alq.sub.3), or tris(8-hydroxyquinoline)-gallium (Gaq.sub.3).

[0118] According to an embodiment of the present disclosure, wherein the electroluminescent device is incorporated into a device group consisting of a consumer product, an electronic component module, an organic light emitting device and a lighting panel.

[0119] According to an embodiment of the present disclosure, a compound formulation comprising a compound having Formula 1 is also disclosed. The specific structure of Formula 1 is as shown in any of the foregoing embodiments.

[0120] Combination with Other Materials

[0121] The materials described in the present disclosure for a particular layer in an organic light emitting device can be used in combination with various other materials present in the device. The combinations of these materials are described in more detail in U.S. Pat. App. No. 20160359122 at paragraphs 0132-0161, which is incorporated by reference herein in its entirety. The materials described or referred to the disclosure are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.

[0122] The materials described herein as useful for a particular layer in an organic light emitting device may be used in combination with a variety of other materials present in the device. For example, materials disclosed herein may be used in combination with a wide variety of emitters, hosts, transport layers, blocking layers, injection layers, electrodes and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Pat. App. No. 20150349273, which is incorporated by reference herein in its entirety. The materials described or referred to the disclosure are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.

[0123] In the embodiments of material synthesis, all reactions were performed under nitrogen protection unless otherwise stated. All reaction solvents were anhydrous and used as received from commercial sources. Synthetic products were structurally confirmed and tested for properties using one or more conventional equipment in the art (including, but not limited to, nuclear magnetic resonance instrument produced by BRUKER, liquid chromatograph produced by SHIMADZU, liquid chromatograph-mass spectrometry produced by SHIMADZU, gas chromatograph-mass spectrometry produced by SIIIMADZU, differential Scanning calorimeters produced by SHIMADZU, fluorescence spectrophotometer produced by SHANGHAI LENGGUANG TECH., electrochemical workstation produced by WUHAN CORRTEST, and sublimation apparatus produced by ANHUI BEQ, etc.) by methods well known to the persons skilled in the art. In the embodiments of the device, the characteristics of the device were also tested using conventional equipment in the art (including, but not limited to, evaporator produced by ANGSTROM ENGINEERING, optical testing system produced by SUZHOU FATAR, life testing system produced by SUZHOU FATAR, and ellipsometer produced by BEIJING ELLITOP, etc.) by methods well known to the persons skilled in the art. As the persons skilled in the art are aware of the above-mentioned equipment use, test methods and other related contents, the inherent data of the sample can be obtained with certainty and without influence, so the above related contents are not further described in this patent.

SYNTHESIS EXAMPLES

[0124] The method for preparing the compounds of the present disclosure is not limited. The following compounds are exemplified as a typical but non-limiting example, and the synthesis route and preparation method are as follows:

Synthesis Example 1: Synthesis of Compound A.SUB.26.L.SUB.0.B.SUB.52 .(Compound 17)

Step 1: Synthesis of [Intermediate 1-a]

[0125] ##STR00047##

[0126] 2-Bromo-4-chloro-1-iodobenzene (60.0 g, 189.05 mmol) was added to a 2000 mL three-neck round bottom flask, then 800.0 mL of anhydrous tetrahydrofuran was added to dissolve, and stirred at room temperature under nitrogen atmosphere. Triethylamine (30.0 mL, 198.2 mmol), cuprous iodide (1.05 g, 5.51 mmol), and bistriphenylphosphine palladium dichloride (4.0 g, 5.70 mmol) were added successively, and kept stirring for 20 min. Trimethylethynyl silicon (23.0 mL, 200 mmol) was added slowly and allowed to react at room temperature for 3 hours. After the reaction completed, the reaction was quenched with water and extracted with ethyl acetate. The organic phase was isolated by column chromatography to give a yellow oil [Intermediate 1-a] (50.0 g, 173.82 mmol, 90.0% yield).

Step 2: Synthesis of [Intermediate 1-b]

[0127] ##STR00048##

[0128] [Intermediate 1-a] (50.0 g, 173.82 mmol), phenylboronic acid (25.5 g, 209.12 mmol), tetrakistriphenylphosphine palladium (6.0 g, 5.2 mmol), potassium carbonate (48.0 g, 398.20 mmol) were added to a 2000 mL three-neck round bottom flask, then 600 mL of tetrahydrofuran and 300 mL of water were added. The reaction flask was warmed to reflux at 85 C. and stirred under nitrogen atmosphere for 12 hours. After the reaction completed, the reaction was cooled to room temperature and extracted with ethyl acetate, the organic phase was dried and concentrated, and then isolated via column chromatography to give a yellow oil [Intermediate 1-b] (40.5 g, 140.50 mmol, 81.0% yield).

Step 3: Synthesis of [Intermediate 1-c]

[0129] ##STR00049##

[0130] [Intermediate 1-b] (26.7 g, 94.5 mmol), potassium carbonate (46.6 g, 337.90 mmol) were added to a 1000 mL three-neck round bottom flask, then 400 mL of methanol was added and kept stirring for 4 hours at room temperature. After the reaction completed, the solid was filtered through celite, the liquid was concentrated and isolated via column chromatography to obtain a pale yellow solid [Intermediate 1-c] (29.0 g, 186.36 mmol, 96.8% yield).

Step 4: Synthesis of [Intermediate 1-d]

[0131] ##STR00050##

[0132] o-Bromoiodobenzene (26.7 g, 94.5 mmol) was added to a 1000 mL three-neck round bottom flask, then 400.0 mL of anhydrous tetrahydrofuran was added to dissolve, and stirred at room temperature under nitrogen atmosphere. Triethylamine (16.5 mL, 169.0 mmol), cuprous iodide (0.55 g, 2.89 mmol), and bistriphenylphosphine palladium dichloride (2.1 g, 3.0 mmol) were added successively, and stirred for 20 min. [Intermediate 1-c] was added slowly (21.0 mL, 98.74 mmol, dissolved in 50 mL of tetrahydrofuran), and reacted at room temperature for 3 hours. After the reaction completed, the reaction was quenched with water and extracted with ethyl acetate, and the organic phase was separated. The organic phase was isolated via column chromatography to obtain a white solid [Intermediate 1-d] (35 g, 87.0 mmol, 90.0% yield).

Step 5: Synthesis of [Intermediate 1-e]

[0133] ##STR00051##

[0134] [Intermediate 1-d] (35 g, 87.0 mmol) was added to a 2000 mL three-neck round bottom flask, then dichloromethane (850.0 mL) was added to dissolve and stirred under nitrogen atmosphere. The reaction flask was cooled to 60 C., and then iodine monochloride (104.0 mL, 104.00 mmol, 1.0 M dichloromethane solution) was slowly added dropwise to the reaction mixture and maintained at 60 C. for 1 hour. After the reaction completed, the reaction was quenched by the addition of saturated aqueous Na.sub.2SO.sub.3, warmed to room temperature and stirred until that the purple color of the solution disappeared. Then dichloromethane was added to extract, the organic phase was dried over MgSO.sub.4, and the organic phase was filtered and concentrated to afford a solid. The obtained solid was added to a 1000 mL round bottom flask, then 500 mL of n-hexane was added and the mixture was warmed to reflux and stirred for 4 hours. After filtration a white solid [Intermediate 1-e] (41.8 g, 78.3 mmol, 91.0% yield) was collected.

Step 6: Synthesis of [Intermediate 1-f]

[0135] ##STR00052##

[0136] [Intermediate 1-e] (35 g, 70 mmol) and 200 mL of anhydrous tetrahydrofuran were placed in a 1000 mL three-neck round bottom flask and stirred at 78 C. under nitrogen atmosphere. After that about 70 mL of n-butyllithium (2.5 M n-hexane solution) was slowly added dropwise at 78 C. for 2 hours, dichlorodiphenylsilane (22.2 mL, 105.0 mmol, dissolved in 50 mL of tetrahydrofuran) was added and the temperature of reaction flack was raised to room temperature and stirred for 3 hours. After the reaction completed, 200 mL of water was added and the organic phase was extracted and separated. The organic phase was isolated via column chromatography to give a white solid [Intermediate 1-f] (17.5 g, 37.4 mmol, 52.5% yield).

Step 7: Synthesis of [Intermediate 1-g]

[0137] ##STR00053##

[0138] [Intermediate 1-f] (17.5 g, 37.4 mmol), bis(pinacolate)diboron (14.25 g, 56.1 mmol), palladium acetate (419.8 mg, 1.87 mmol), 2-dicyclohexylphosphino-2,6-dimethoxybiphenyl (1.53 g, 3.74 mmol), potassium acetate (11.1 g, 112.2 mmol) were added to a 250 mL three-neck round bottom flask, followed by the addition of 120 mL of 1,4-dioxane. The reaction flask was heated to reflux at 110 C. and stirred under nitrogen atmosphere for 10 hours. After the reaction completed, the reaction mixture was cooled to room temperature and extracted with methylene chloride. The organic phase was dried and concentrated, then isolated via column chromatography to give white solid [Intermediate 1-g](13.5 g, 24.10 mmol, 64.4% yield).

Step 8: Synthesis of A.SUB.26.L.SUB.0.B.SUB.52

[0139] ##STR00054##

[0140] [Intermediate 1-g] (5.05 g, 9.0 mmol), 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine (3.1 g, 9.0 mmol), tetrakistriphenylphosphine palladium (520 mg, 0.45 mmol), potassium carbonate (3.75 g, 27.0 mmol) were added to a 250 mL three-neck round bottom flask, followed by the addition of 60 mL of tetrahydrofuran and 20 mL of water. The reaction flask was warmed to reflux at 85 C. and stirred under nitrogen atmosphere for 12 hours. After the reaction completed, the reaction mixture was cooled to room temperature and extracted with methylene chloride. The organic phase was dried and concentrated, and then isolated by column chromatography to give a yellow solid compound A.sub.26L.sub.0B.sub.52 (5.6 g, 7.55 mmol, 84.5%). The product was confirmed as the target product, with a molecular weight of 742.

Example 2: Synthesis of Compound A.SUB.30.L.SUB.0.B.SUB.52 .(Compound 197)

Step 1: Synthesis of [Intermediate 2-a]

[0141] ##STR00055##

[0142] In the step 1 of Synthesis Example 1, o-iodobiphenyl was used instead of 2-bromo-4-chloro-1-iodobenzene, and [Intermediate 2-a] (28.5 g, 38% yield) was obtained by the same procedure.

Step 2: Synthesis of [Intermediate 2-b]

[0143] ##STR00056##

[0144] In the step 3 of Synthesis Example 1, [Intermediate 2-a] was used instead of [Intermediate 1-b], and [Intermediate 2-b] (19.56 g, 93.6% yield) was obtained by the same procedure.

Step 3: Synthesis of [Intermediate 2-c]

[0145] ##STR00057##

[0146] In the step 4 of Synthesis Example 1, [Intermediate 2-b] was used instead of [Intermediate 1-c], and 2-bromo-4-chloro-1-iodobenzene was used in place of o-bromoiodobenzene and [Intermediate 2-c] (31.3 g, 79.2% yield) was obtained by the same procedure.

Step 4: Synthesis of [Intermediate 2-d]

[0147] ##STR00058##

[0148] In the step 5 of Synthesis Example 1, [Intermediate 2-c] was used instead of [Intermediate 1-d], and [Intermediate 2-d] (36.7 g, 85.7% yield) was obtained by the same procedure.

Step 5: Synthesis of [Intermediate 2-e]

[0149] ##STR00059##

[0150] In the step 6 of Synthesis Example 1, [Intermediate 2-d] was used instead of [Intermediate 1-e], and [Intermediate 2-e] (15 g, 63.0% yield) was obtained by the same procedure.

Step 6: Synthesis of [Intermediate 2-f]

[0151] ##STR00060##

[0152] In the step 7 of Synthesis Example 1, [Intermediate 2-e] was used instead of [Intermediate 1-f], and [Intermediate 2-f] (5.55 g, 56.2% yield) was obtained by the same procedure.

Step 7: Synthesis of Compound A.SUB.30.L.SUB.0.B.SUB.52

[0153] ##STR00061##

[0154] In the step 8 of Synthesis Example 1, [Intermediate 2-f] was used instead of [Intermediate 1-g], and compound A.sub.30L.sub.0B.sub.52 (4.2 g, 84.3% yield) was obtained in the same manner. The product was confirmed as the target product, with a molecular weight of 742.

Example 3: Synthesis of Compound A.SUB.30.L.SUB.2.B.SUB.51 .(Compound 256)

Step 1: Synthesis of Compound A.SUB.30.L.SUB.2.B.SUB.51

[0155] ##STR00062##

[0156] In the step 8 of Synthesis Example 1, [Intermediate 2-f] was used instead of [Intermediate 1-g], and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine, and compound A.sub.30L.sub.2B.sub.51 (3.6 g, 60.7% yield) was obtained in the same manner.

Example 4: Synthesis of Compound A.SUB.30.L.SUB.0.B.SUB.53 .(Compound 198)

Step 1: Synthesis of Compound A.SUB.30.L.SUB.0.B.SUB.53

[0157] ##STR00063##

[0158] In the step 8 of Synthesis Example 1, [Intermediate 2-f] was used instead of [Intermediate 1-g], and 2-([1,1-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine, and compound A.sub.30L.sub.0B.sub.53 (3.8 g, 85.3% yield) was obtained in the same manner.

Example 5: Synthesis of Compound A.SUB.29.L.SUB.0.B.SUB.52 .(Compound 107)

Step 1: Synthesis of [Intermediate 5-c]

[0159] ##STR00064##

[0160] To a 1000 mL three-neck round bottom flask was added 2-bromo-5-chloroiodobenzene (33.7 g, 106.1 mmol), and then 425.0 mL of anhydrous tetrahydrofuran was added to dissolve, and was stirred at room temperature under nitrogen atmosphere. Triethylamine (30 mL, 212.2 mmol), cuprous iodide (0.58 g, 3.0 mmol), bistriphenylphosphine palladium dichloride (2.1 g, 3.0 mmol) were added successively, and stirred for 30 min. [Intermediate 2-b] (18.0 mL, 101.0 mmol, dissolved in 75 mL of THF) was added slowly, and reacted for 10 hours at room temperature. After the reaction completed, the reaction was quenched with water and extracted with ethyl acetate, and the organic phase was separated. The organic phase was isolated via column chromatography to obtain a white solid [Intermediate 5-c] (30 g, 81.6 mmol, 80.8% yield).

Step 2: Synthesis of [Intermediate 5-d]

[0161] ##STR00065##

[0162] [Intermediate 5-c] (27.5 g, 74.8 mmol) was added to a 1000 mL three-neck round bottom flask, then dichloromethane (650.0 mL) was added to dissolve and stirred under nitrogen atmosphere. The reaction flask was cooled to 60 C., and then iodine monochloride (90.0 mL, 90.00 mmol, 1.0 M dichloromethane solution) was slowly added dropwise to the reaction mixture and the reaction was maintained at 60 C. for 1 hour. After the reaction completed, the reaction was quenched by the addition of saturated aqueous Na.sub.2SO.sub.3, warmed to room temperature and stirred until that the purple color of the solution disappeared. Then dichloromethane was added to extract, the organic phase was dried over MgSO.sub.4, and the organic phase was filtered and concentrated to afford a solid. The obtained solid was added to a 1000 mL round bottom flask, then 500 ml, of n-hexane was added and the mixture was warmed to reflux and stirred for 8 hours. After filtration a white solid [Intermediate 5-d] (23.0 g, 46.8 mmol, 62.5% yield) was collected.

Step 3: Synthesis of [Intermediate 5-e]

[0163] ##STR00066##

[0164] [Intermediate 5-d] (22.8 g, 46.3 mmol), 150 mL of anhydrous tetrahydrofuran were placed in a 500 mL three-neck round bottom flask and stirred at 78 C. under nitrogen atmosphere. After that about 46 mL of n-butyllithium (2.5 M n-hexane solution) was slowly added dropwise at 78 C., after the low temperature was kept for 2 hours, dichlorodiphenylsilane (14.6 mL, 69.5 mmol) was added and the temperature of reaction flack was raised to room temperature and stirred for 18 hours. After the reaction completed, 200 mL of water was added and the organic phase was extracted with dichloromethane and separated. The organic phase was isolated via column chromatography to give a white solid [Intermediate 5-e] (10.8 g, 23.0 mmol, 49.8% yield).

Step 4: Synthesis of [Intermediate 5-f]

[0165] ##STR00067##

[0166] [Intermediate 5-e] (10.8 g, 23.0 mmol), bis(pinacolate)diboron (8.5 g, 34.6 mmol), palladium acetate (252 mg, 1.15 mmol), 2-dicyclohexylphosphino-2,6-dimethoxybiphenyl (920 mg, 2.3 mmol), potassium acetate (6.5 g, 69.0 mmol) were added to a 250 mL three-neck round bottom flask, followed by the addition of 80 mL of 1,4-dioxane. The reaction flask was heated to reflux at 120 C. and stirred under nitrogen atmosphere for 15 hours. After the reaction completed, the reaction mixture was cooled to room temperature and extracted with methylene chloride. The organic phase was dried and concentrated, then isolated via column chromatography to give white solid [Intermediate 5-f](7.6 g, 13.5 mmol, 58.8% yield).

Step 5: Synthesis of Compound A.SUB.29.L.SUB.0.B.SUB.52

[0167] ##STR00068##

[0168] [Intermediate 5-f] (4.0 g, 7.1 mmol), 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine (2.5 g, 7.1 mmol), tetrakistriphenylphosphine palladium (412 mg, 0.36 mmol), potassium carbonate (3.0 g, 21.4 mmol) were added to a 250 mL three-neck round bottom flask, followed by the addition of 60 ml, of tetrahydrofuran and 20 mL of water. The reaction flask was warmed to reflux at 85 C. and stirred under nitrogen atmosphere for 15 hours. After the reaction completed, the reaction system was cooled to room temperature and extracted with methylene chloride. The organic phase was dried and concentrated, and then isolated by column chromatography to give a yellow solid compound A.sub.29L.sub.0B.sub.52 (4.3 g, 5.8 mmol, 81.2%).

Example 6: Synthesis of Compound A.SUB.29.L.SUB.0.B.SUB.53 .(Compound 108)

Step 1: Synthesis of Compound A.SUB.29.L.SUB.0.B.SUB.53

[0169] ##STR00069##

[0170] In the step 5 of Synthesis Example 5, 2-([1,1-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine, and compound A.sub.29L.sub.0B.sub.53 (3.7 g, 78.0% yield) was obtained in the same manner.

[0171] The persons skilled in the art should know that the above preparation method is only an illustrative example, and the persons skilled in the art can obtain the structure of other compounds of the present disclosure by modifying the above preparation method.

DEVICE EXAMPLE

Example 1 and Comparative Example 1

[0172] A glass substrate with 80 nm thick indium-tin-oxide (ITO) anode was first cleaned and then treated with oxygen plasma and UV ozone. After the treatments, the substrate was dried in a glovebox to remove moisture. The substrate was then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were deposited in sequence by thermal vacuum deposition on the ITO anode at a rate of 0.2-2 /s under a vacuum degree of around 10.sup.8 torr. Compound HI was used as the hole injection layer (HIL, 100 ). Compound HT was used as the hole transporting layer (HTL, 400 ). Compound EB was used as the electron blocking layer (EBL, 50 ). Then the Compound RD1 was doped in the host Compound HOST (Compound HOST:Compound RD1=97:3, 400 ) as the emitting layer (EML). On the emitting layer, Compound HB was deposited as hole blocking layer (HBL, 50 ). The Compound A.sub.30L.sub.0B.sub.52 of the present disclosure or the comparative Compound ET1 was then doped with 8-hydroxyquinoline-lithium (Liq) as an electron transporting layer (ETL, 350 ). Finally, 10 -thick 8-hydroxyquinoline-lithium (Liq) was deposited as the electron injection layer and 1200 of Al was deposited as the cathode. The device was then transferred back to the glovebox and encapsulated with a glass lid and a moisture getter to complete the device.

[0173] The detailed electron transporting layer structure and thicknesses are shown in the table below. In the layers in which more than one material was used, they were obtained by doping different compounds in the weight ratios described therein.

TABLE-US-00001 TABLE 1 Device structure of device examples Device ID ETL Example 1 Liq: Compound A.sub.30L.sub.0B.sub.52 (60:40) (350 ) Comparative Liq: Compound ET1 (60:40) (350 ) Example 1

[0174] Structures of the materials used in the devices are shown as below:

##STR00070## ##STR00071##

[0175] Sublimation temperature of Compound A.sub.30L.sub.0B.sub.52 and Compound ET1, the chromaticity coordinate (CIE), max and half-width (FWHM) of Example 1 and Comparative Example 1 at 1000 nits, and the results of lifetimes tested with constant current from an initial brightness of 7500 nits are shown in Table 2, respectively.

TABLE-US-00002 TABLE 2 Device data Sub T .sub.max FWHM LT97 Device ID ( C.) CIE (x, y) (nm) (nm) (h) Example 1 301 (0.661, 0.338) 619 61.2 352 Comparative 249 (0.661, 0.338) 619 61.4 268 Example 1

Example 2 and Comparative Example 2

[0176] According to the above example, only the emitting layer (EML) and the electron transporting layer (ETL) were changed: the compound RD2 was doped in the host Compound HOST (Compound HOST:Compound RD2=97:3, 400 ) as the emitting layer (EML). The Compound A.sub.30L.sub.0B.sub.52 of the present disclosure or the comparative Compound ET2 was doped with 8-hydroxyquinoline-lithium (Liq) as an electron transporting layer (ETL).

[0177] The detailed structure and thickness of the electron transporting layer are shown in the table below. In the layers in which more than one material was used, they were obtained by doping different compounds in the weight ratios described therein.

TABLE-US-00003 TABLE 3 Device structure of device examples Device ID ETL Example 2 Liq: Compound A.sub.30L.sub.0B.sub.52 (60:40) (350 ) Comparative Liq: Compound ET2 (60:40) (350 ) Example 2

[0178] Structure of the materials used in the devices are shown as below:

##STR00072##

[0179] Sublimation temperature of Compound A.sub.30L.sub.0B.sub.52 and Compound ET2, The current efficiency (CE), voltage, chromaticity coordinate (CIE), max and half-width (FWHM) of Example 2 and Comparative Example 2 at 1000 nits, and the results of lifetimes tested with constant current from an initial brightness of 7500 nits are shown in Table 4, respectively.

TABLE-US-00004 TABLE 4 Device data Device Sub T CE/ Voltage .sub.max FWHM LT97 ID ( C.) (cd/A) (V) CIE (x,y) (nm) (nm) (h) Example 301 22.33 4.33 (0.684,0.316) 625 49.0 484.6 2 Com- 298 22.41 4.02 (0.683,0.316) 625 49.3 328.8 parative Example 2

[0180] Discussion:

[0181] As the results shown in Table 2 and Table 4, it can be confirmed that the compounds represented by Formula 1 of the present disclosure can be used for an electron transporting material layer of an organic light-emitting device, and exhibits excellent characteristics in terms of lifetime of the device.

Example 3

[0182] First, a glass substrate which has 80 nm-thick indium-tin-oxide (ITO) anode was cleaned, and then treated with oxygen plasma and UV ozone. Then the cleaned substrate was dried in a glovebox to remove moisture. The substrate was then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were deposited in sequence by thermal vacuum deposition on the ITO anode at a rate of 0.2-2 /s under a vacuum degree of around 10.sup.8 torr. Compound HI was used as the hole injection layer (HIL, 100 ). Compound HT was used as the hole transporting layer (HTL, 1200 ). Compound EB1 was used as the electron blocking layer (EBL, 50 ). Then Compound BH and Compound BD (weight ratio of 96:4) codeposited as the emitting layer (EML, 250 ). On the emitting layer, Compound HB1 was deposited as hole blocking layer (HBL, 50 ). Then Compound A.sub.30L.sub.0B.sub.52 of the present disclosure was doped in 8-hydroxyquinoline-lithium (Liq) (weight ratio of 40:60) as an electron transporting layer (ETL, 300 ). Finally, 10 -thick 8-hydroxyquinoline-lithium (Liq) was deposited as the electron injection layer (EIL) and 1200 -thick Al was deposited as the cathode. The device was then transferred back to the glovebox and encapsulated with a glass lid and a moisture getter to complete the device.

Example 4

[0183] Example 4 is fabricated in the same manner as Example 3, except that Compound A.sub.30L.sub.2B.sub.51 was used instead of Compound A.sub.30L.sub.0B.sub.52 in the ETL.

Example 5

[0184] Example 5 is fabricated in the same manner as Example 3, except that Compound A.sub.30L.sub.0B.sub.53 was used instead of Compound A.sub.30L.sub.0B.sub.52 in the ETL.

Example 6

[0185] Example 6 is fabricated in the same manner as Example 3, except that Compound A.sub.29L.sub.0B.sub.52 was used instead of Compound A.sub.30L.sub.0B.sub.52 in the ETL.

Example 7

[0186] Example 7 is fabricated in the same manner as Example 3, except that Compound A.sub.29L.sub.0B.sub.53 was used instead of Compound A.sub.30L.sub.0B.sub.52 in the ETL.

Comparative Example 3

[0187] Comparative Example 3 is fabricated in the same manner as Example 3, except that Compound ET2 was used instead of Compound A.sub.30L.sub.0B.sub.52 in the ETL.

[0188] The detailed structure and thickness of the electron transporting layer are shown in the table below. In the layers in which more than one material was used, they were obtained by doping different compounds in the weight ratios described therein.

TABLE-US-00005 TABLE 5 Device Structure of Device Examples and Comparative Example Device ID ETL Example 3 Compound A.sub.30L.sub.0B.sub.52: Liq (40:60, 300 ) Example 4 Compound A.sub.30L.sub.2B.sub.51: Liq (40:60, 300 ) Example 5 Compound A.sub.30L.sub.0B.sub.53: Liq (40:60, 300 ) Example 6 Compound A.sub.29L.sub.0B.sub.52: Liq (40:60, 300 ) Example 7 Compound A.sub.29L.sub.0B.sub.53: Liq (40:60, 300 ) Comparative Compound ET2: Liq (40:60, 300 ) Example 3

[0189] The structure of the new materials used in the devices were as shown below:

##STR00073## ##STR00074## ##STR00075##

[0190] CIE coordinates, external quantum efficiency (EQE) under the brightness of 1000 cd/m.sup.2, and the lifetime (LT95) under a current density of 15 mA/cm.sup.2 of Example 3-7 and Comparative Example 3 were all recorded and shown in Table 6.

TABLE-US-00006 TABLE 6 Device Data EQE Device ID CIE (%) LT95 (h) Example 3 (0.139, 0.092) 7.35 326 Example 4 (0.139, 0.092) 7.77 219 Example 5 (0.139, 0.093) 7.41 324 Example 6 (0.139, 0.092) 7.77 286 Example 7 (0.139, 0.092) 7.64 212 Comparative (0.139, 0.085) 6.68 186 Example 3

[0191] Discussion:

[0192] From the table above, the differences of the device structure among the examples of the present disclosure and the comparative example lie in the differences between the electron transporting materials. The Compound ET2 used in the comparative example is a common electron transporting material in the industry. Obviously, both in efficiency and lifetime of Example 3-7 are better than Comparative Example 3. The efficiency can be improved by 10%-16%, and there is a 14%-75% improvement in lifetime. The efficiency and lifetime of blue light in OLED display screen is the weakest link, therefore it is very important to achieve an improvement in the performance of the material of the present disclosure.

[0193] It is understood that the various embodiments described herein are by way of example only, and are not intended to limit the scope of the disclosure. The present disclosure as claimed may therefore include variations from the particular examples and preferred embodiments described herein, as will be apparent to one of skill in the art. Many of the materials and structures described herein may be substituted with other materials and structures without deviating from the spirit of the present disclosure. It is understood that various theories as to why the disclosure works are not intended to be limiting.